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The story that follows is, for the most part, true. It is part one of a real experience that took place over several years. I have filled in or slightly modified some details, and of course changed the names.
To be honest I don’t really remember how it started. It was a craigslist post, I don’t remember if I responded to his or he responded to mine. We got in to an email exchange, both of us interested in doing something but neither in an ‘I need to get some in the next two hours’ hurry.
Jim said he was very open, said he was looking to act on his curiosity for the first time. We were both looking for a mutual blowjob type of thing. He described himself as 30, tall and average looking with a bit of a belly. I described myself as 40ish, tall and good looking preppy type, fit and hung average. Clearly not used to the rules of exchanging stats with guys, Jim had no idea that cock size is part of the required exchange. So I asked. Jim wasn’t shy, but still clearly didn’t know the game. “I’m hung about average too, don’t know if I did it right but if I measure on the top it’s about 8 inches long. I’m told it’s pretty thick.”
My jaw almost hit my keyboard. I needed to move quickly, this guy had no idea he is seriously hung, has no idea how important cock size is in the guy world.
Ok, there is one more detail. I am Skip. I described myself as hung average, but like Jim, that isn’t entirely accurate. Do a web search and you find that the ‘average’ erection is between 5.5″ and 6″. I do perform real well, get hard as steel and it points well north of horizontal. But the honest truth, measured on top on my very best day, I am shy of 4″. 3 ¾” is more precise. On the thin side, but very well shaped. The same web data tells you that 98% of guys are hung better than me. About 10% of guys are like Jim, hung with literally more than twice as much cock. And those are the only guys I care about, the really well endowed. Hung average does nothing for me. I like them big, very big. Thick is good, but most of what I crave is length, plain and simple. Seven inch minimum, the truly blessed is what we are talking about. Guys with less than 4″ don’t get the time of day from those guys, so I knew I needed to close the deal with Jim.
I made my move, Jim had already said he wanted to host so I pushed to set a time.
Jim’s next email stunned me. “Sounds great, but one more thing. I have a girlfriend. She’s cool with this, but wants to stay and watch. She’s very nice, kind of a BBW type with huge tits, and promises she will sit quietly in the corner and not interfere.”
Super hung guy has a stacked girlfriend who wants to watch…what is this Christmas? “Sure Jim, no problem. How about 3:00?”
The deal was done, an address was forwarded. Jim asked me to bring condoms for both of us, he said he preferred Magnums, “I think they’re more comfortable, I’m sure most guys do.”
Uh yeah. Lifestyle condoms makes a condom they call ‘Snugger Fit’, a marketing term that makes it so guys like me don’t have to ask for small size condoms. Regular size doesn’t really work for me.
I drove by Jim’s house about 2:45, basic ranch in the next town to me. Jim rented the basement in law apartment, enter around the back he told me. I was a little nervous, and semi-hard. Freshly showered, I could feel pre-cum in my underwear. I pulled in to a parking lot of a close by convenience store, and waited an eternity for 3:00 to come. Finally I pulled up to the front of Jim’s house, a couple of minutes early, but I couldn’t wait any longer. I made some adjustments so my trouser tent wouldn’t be obvious. There was the very slight beginnings of a wet spot on my slacks but I doubted it would be obvious. I walked around the side of house, through the gate, and found Jim waiting for me on the patio at the back door. Just as he described, about my height (6’2″) , very average looking with a thin moustache and a few extra pounds around the middle. He greeted me warmly, and invited me in .
Jim’s place was very small, all one room and very untidy. A good size TV sat in the corner, on the screen a stacked blonde was giving a guy a blowjob. In the opposite corner was a big upholstered chair containing Laura, Jim introduced me to his girlfriend with not a hint of awkwardness.
Laura eyed me with confidence and didn’t offer a hello. “How old are you?” she demanded.
A bit taken aback I blurted out, “40”.
Her eyes drifted down to my belt, her smirk made it clear that she noticed my erection, but then she actually leaned slightly forward and squinted a bit. The show of cleavage could make your knees weak. She clearly was staring at the wet spot…”Huh.” was all she said. Laura sat back and smiled. As advertised she was on the bigger side, but her bust line was enormous and at most she was 24. She glanced down at her t shirt straining to contain her bust, then slowly raised her eyes in a way that made it clear she knew the effect her bust has on men. She picked up her pack of Marlboro Lights off the side table, slowly lit one, and let out a long, sexy, purposeful exhale. “Welcome Skip.” she said with a superior smile.
Jim flopped comfortably down on his double bed and made small talk about our email exchange. He asked me if I had brought our condoms, and held out his hand for them.
I now panicked a bit, realizing I was going to hand over both of our condoms and he was going to find out that not only aren’t we both ‘magnum class’, but far from it. My size smalls would tip my hand. Having no other choice I handed over two of each size from my pocket, thankfully he barely glanced at them as he tossed them on the nightstand and I thought I was off the hook.
Jim reached for his belt. “Why don’t we get ready for some fun, you can put your clothes on the chair by the desk.” he directed.
As I started to shuffle toward the chair and fiddle with my shirt buttons Laura caught the corner of my eye. The condoms on the night stand caught her attention. She reached over and picked up one of my snugger fits. She took a long purposeful drag on her cigarette as she studied the package. She held up the package with a grin, again “Huh.” was all she said.
By now Jim had slipped off his sweat pants and was pulling off his socks. His speedo style briefs tightly clearly outlined a huge shaft. “What’s up?” he asked Laura.
“Well, Skip for starters.” as she gestured with the foil wrapper. I blushed, but couldn’t deny it. “But according to this package, Skippy here has a little one.” she said with a smirk.
I was mortified, and both Jim and Laura just stared silently. Finally Jim broke in to a broad grin. He flopped back on to the bed in his briefs and a t-shirt, his enormous flaccid cock threatened to slip out of the skimpy briefs at any moment. “Only one way to know for sure Skipper, keep on going,” he said as he gestured to the rest of my clothes. The both just sat and stared, I had no choice but to strip for them.
I was kind of deliberate as I finished taking off my shirt and fumbled with my belt. I knew I was fully hard, and to make matter worse I knew that the front of my briefs were now fairly soggy with precum.
I tried to turn my back, but Laura would have none of that. “Uh-uh.” was all she said. I figured the state of my underwear was an embarrassment I could avoid, so I hooked my waistband with the top of my slacks and slid both off at once. Unfortunately my waistband caught the head of my cock, pulling it down and causing it to snap back up cartoonishly, slapping against my abdomen. Laura was in mid-inhale, and blew out a huge cloud of smoke as she sputtered. “Yup…looks like he bought the right size!” was all she said.
Jim grinned, but seemed unfazed. “Well little buddy, should we get started.” He hooked his briefs and slid them off.
I couldn’t help it, I gasped out loud. What flopped out of his briefs was nothing short of incredible. I would later find out Jim is a shower, not a grower. His shaft is a big, thick pipe. No veins or detail, just a big heavy slab of cock that hung downward and swayed. He has similarly big heavy balls. At least 7″ long as it just hung there completely soft. But the truly world class part was the head, perfectly shaped and enormous, the size of a small fist. Even on his thick shaft it looked outsized and powerful. I could only stare in open mouth admiration and lust. My own puny unit went from hard to a next level I didn’t know existed. It surged to painfully hard and pointed absolutely due north.
Wordlessly Laura handed me a tissue and gestured, I looked down to find a long string of precum dangling off the end of my aching cock. “I think you have his attention Jimmy!” she chuckled.
It was clear that Laura was enjoying this, she was keenly aware of how everything she had said and done was embarrassing me. Without saying it though we both knew no matter how much fun she chose to have at my expense I had to play along, or at least take it. While Jim might have been naively unaware of just how extraordinary his endowment was, Laura knew very well how he stacked up. We both knew she had already done the mental calculus, and a forty something guy with 3+” was very, very lucky to be getting a shot at Jim’s 30 something gigantic cock. And we both knew she could end this whole scene at any time. We both knew all of these things, and a moment of eye contact between us created an unspoken deal. She wasn’t going to shut this down as long as I played by her rules.
Jim lay back on a stack of 4 or 5 pillows and spread his legs, and gestured that I was welcome to begin. I started to climb up on to the bed when Laura interrupted. She held out a foil package and said, “Skip, why don’t you put one of these on so you don’t drip all over everything.” The condescending inference was powerful, my lack of control and intense arousal, the contrast of my intense erection to Jim’s flaccid member, the constant stringy pre-cum. But I couldn’t say a word, so I reached for the foil wrapper.
As I went to tear it open I looked down at the package clearly marked ‘Magnum’. I could see Laura’s grin out of the corner of my eye. I had no choice but to ask her for one of the small condoms, a request I mumbled in shame.
“Oh, my mistake,” she giggled as she handed over the light blue foil and took back the deep purple Magnum wrapper. “Jim, do you want this condom now, or would you prefer Skippy suck you without a condom…you don’t mind do you Skippy?” The look on Jim’s face made it clear what his preference was, but he didn’t answer right away. “Don’t worry baby, whichever way you choose, Skippy will still wear one. Under the circumstances you shouldn’t have to if you prefer it bare…” Her tone made it clear what ‘under the circumstances’ meant. She turned to me. “If you’re not comfortable that’s fine, we don’t have to do this today.” Laura knew that with that huge cock in front of me, and in the state I was in there was no chance I was going to say no. Jim declined the condom, but they both watched as I rolled my fitted condom on.
Finally I was able to reach out and put my hand on Jim’s enormous lolling hose. The weight, the warmth and the sheer size caused a surge in my groin, I had to stop and screw my eyes shut and suck some air for a moment to keep from losing my load. While Jim had no idea, Laura let out a stifled giggle, it was clear that she knew just touching his dick almost made me cum. Having gained some control, I wrapped my hand around his flaccid shaft, my hand didn’t make it all the way around. I ran my other hand over the huge head and let out an audible moan. I slowly stroked the length of the shaft twice, then again felt the cum rising in my balls and had no choice but to let go of Jim’s cock. I fell to all fours and desperately fought to keep from cumming once again, gasping and panting. This time there was no missing what was happening.
“Looks like your getting a little too excited Skip,” Jim said with a chuckle.
Laura laughed out loud. She lit another Marlboro Light and said, “Maybe you’re more than he can handle Jimmy.” I wanted to insist it wasn’t the case, but I still was afraid to move as my hold on my orgasm was very fragile.
Eventually I was able to gain some composure, and managed to perform. I was able to work Jim’s massive cockhead in to my mouth and soon was slurping and sucking and licking. Only then did I feel him begin to grow and harden, finally after about 5 minutes I think he was truly erect. He clearly was enjoying himself, but required hard work to arouse. My jaw and back were beginning to ache, and he was showing no signs of moving toward anything more than mild arousal. I tried moving to a handjob to give my jaw a rest, but Laura quite firmly told me Jim much prefers oral. Again the mischievous grin, she knew what she was doing. After a full 25 minutes my jaw, my arms, my back and my knees were screaming. I was coated in sweat.
Jim was laying back, watching porn, and seemingly unaffected by all my hard work. A couple of times he assured Laura that I was doing a good job, but she had nothing to worry about, I wasn’t in her league. Jim was hard, but he showed no signs of progressing toward getting hot, let alone an orgasm. But for all the aches I had in so many places, perhaps my greatest source of discomfort was my throbbing hard erection and a now impressive pool of pre-cum filling my condom. I was increasingly desperate for some kind of relief.
The fact was not lost on Laura. “Look, he’s humping!” she announced with what sounded like glee. I had no idea, but apparently had started thrusting in some desperate attempt at friction.
Finally I got what I thought would be a break. Jim smiled at my humping attempts for relief. “Why don’t we swap places, let me work on your for a while,” he suggested.
I sat back on my ankles to smile and agree, only to get a whole new perspective on Jim’s cock. Now for the first time was I seeing it fully engorged as it pointed toward his chin. The shaft was now veined, and nearly as thick as my (admittedly thin) wrist. But the massive head induced awe as it was now fully plumped with arousal. Jim sat up and I was helpless to do anything but sit and stare. So now we are both in a face to face, sitting position, me naked and Jim wearing a t-shirt. But in our sitting positions our erections were now only about 6 inches apart, mine condom clad.
There was no avoiding the comparison, and Laura let out low, guttural “Wow!” My rock hard cock was dwarfed by Jim’s rigid tool …in length, in girth, the size of its head and the size of our balls. Jim’s looked like an imposing weapon next to my puny toy.
Jim directed me to prop up against the pillows as he had been, though Laura tossed me a towel to put down because I was so sweaty. Jim sprawled out next to me and reached for my cock. At first he looked a bit stumped what to do when his large hands were too big to grip me with a fist. He took his thumb and forefinger and delicately gripped my cock just below the head. Once again I had to gasp and strain to keep from cumming.
Laura commented on the amount of pre-cum that had overflowed the reservoir tip and flowed back in to the body of the condom. Jim leaned forward to examine my cock more closely, then gently ran his thumb and forefinger slowly down the shaft and back to the top. At that point I lost the battle, and arched my back and let out a low moan . Jim pulled his hand away, but it was too late, and I gasped out a stifled scream of pleasure and frustration from Jim dropping me and not stroking it out. The condom flooded.
Laura let out a long, loud laugh and blurted out, “That was so pathetic, he barely touched you.” Jim just sat back and smiled, and they both watched me try to recover and mumble some excuses.
Laura made it clear I was going to finish what I came there for, and I did. Jim sat on the end of the bed with me on my knees on the floor. He watched more porn while I worked on his unyielding erection for another 30 minutes. I tried every trick and technique I could think of, but he just rested contentedly enjoying my work but not making any progress toward finishing. I would have cum five or six times and he was just barely staying hard.
Finally Jim pushed me off of his cock and stroked himself off. Laura sent me for a warm wash cloth and had me clean Jim up. She lit another cigarette, and handed me her ashtray to empty. She smiled as she commented on how my hard on had returned, it was funny to watch it bounce while I walked.
Laura directed me to get dressed, it being clear that if I needed some attention for my erection that should be done somewhere else. She made a point of noticing my tented pants as I was ready to leave. Jim was very pleasant and thanked me for a good time, but pointedly neither of them responded when I suggested we should do this again some time.
The drive home was a blur, I don’t remember any of it but mercifully it was only 15 minutes or so. I say mercifully because my throbbing hard on was unrelenting. The image of Jim’s enormous cock, it’s overwhelming girth in my mouth had me achingly erect the entire drive. When I finally pulled in to my garage I was in bad shape, and longed for some relief. I would have run to the bathroom if my tented slacks allowed it, so I hobbled as rapidly as I could. I stood at the bathroom sink fumbling with my belt, finally working the clasp successfully and letting the pants drop to the floor. My briefs were soaked with precum to the point of translucence, the angry cock head clearly visible. I thrust my hand under the waist band and gripped my hard cock with my thumb and forefinger and stroked furiously. By the third stroke I knew relief was near, my head was already thrown back, mouth open as I gasped for breath. The fifth stroke unleashed the first powerful blast of cum in to my Jockeys, soaking my hand in the process. Surge after surge of cum followed as I let out a long, primitive moan. As the last waves of orgasm rolled over me I had to grab the sink to keep from falling, finally dropping to my knees wheezing and dizzy. My hand was still firmly buried in my underwear and a long string of cum drooled toward the floor. It was as powerful an orgasm as I could remember.
In the next hour it was followed by two more rounds of needed masturbation, neither approaching the intensity of the first, but very impressive in the powerful orgasm each yielded. I was consumed with the image of Jim’s huge member. I was drained and my balls ached from repeatedly being pushed to their limits of propulsion. I sat on my bathroom floor, hand on my tiny, wasted cock, dazed and helpless to the memories of the afternoon.
Finally I was able to regain some control, and took a long hot shower to attempt to clear my head and clean off an afternoons crust of the remnants of repeated loads of precum and cum. While the shower helped a great deal, bringing me back to feeling nearly normal again, the soaping motion created yet another erection, and I soon found myself leaning against the tile as I unleashed the fifth load of the afternoon and evening with a wailing grunt. I collapsed in to my bed after drying off, my cock chafed and raw and my balls throbbing. I was asleep almost immediately.
The nights sleep was very sound, my body and my mind wasted by the previous afternoon. But the rest brought some recovery to my exhausted privates, and they woke me in the morning with a boner that cried out for immediate attention that couldn’t wait for a bathroom trip. I gingerly gripped my still raw cock with my familiar two finger grip, in very short order sent a new load of cum skyward to splash down on my chest and neck. The volume was moderate, but the distance of the shoot exceeded anything since my teenage years, splashing on my throat.
I knew I needed to see Jim again, desperately needed to see him. I was haunted by his big cock and so badly wanted another chance to service it. But I was also confused by the arousing memory of Laura, sitting to the side pulling all the strings as she kept nudging the action for her amusement. She clearly enjoyed needling and humiliating me, enjoyed the power my obvious desperation for Jim’s cock gave her, obviously delighted in using my small cock and premature ejaculation to make it clear she considered me to be much less of a man. And I took it. I had to.
But most searing was the look of delight in her eyes as I left, plainly asking them for a chance to visit again, a request which fell completely flat, no response. My desperation only emphasized by my obvious erection which Laura had not permitted me to relieve.
I had to try. I couldn’t ask right away, that would be too pathetic, but it took all of my self control to wait two days before I found myself staring at a blank email addressed to Jim’s inbox.
‘Jim- Thanks for a great time Tuesday afternoon, I really enjoyed meeting you and Laura. Hope you enjoyed it too. I would love to get together again sometime soon, let me know when you might have some time.
I re-read my message over and over, inserted and deleted a line or two about his big cock, finally just hit send.
And then I waited. And waited some more. A few hours became a day, then two, then three. Finally on day four I found Jim’s name in my inbox.
‘Hey skip. Enjoyed meeting you too, you seem like a nice guy. Talked about it with Laura and not sure if we are a good match to meet again. I think for next time I am looking for a guy a little more like me and would like to be able to play with him a little too, looking for a guy who can handle that part a little better. Who knows, maybe we will hook up again some time down the road. J.’
I was crestfallen and disappointed, but I couldn’t give up. I had been jacking off at least twice a day to the memory of the afternoon with Jim, and have to admit that increasingly I had found myself fantasizing about Laura. About Laura and her enormous breasts, directing my humiliation from behind a smoky haze of bitchy confidence. For gods sake, she was maybe 23 and I am nearly twice her age. What she would give for my BMW…but she also holds the cards in this deal, she knows I have to kiss her ass.
I had to get back in the door, had to convince Jim to let me visit again. Somehow, some way.
‘Jim- Thanks for the reply. Hey, I understand what you are saying, and I wasn’t at my best that day. Would love to get another shot to show you that wasn’t really me. Would be more than happy to do a no reciprocation deal if you like, what guy doesn’t like just lying back and getting a blowjob? Give me another chance, trust me, you won’t regret it! Can arrange my schedule for what works for you…let me know…
The arrange my schedule part sounded so desperate when I re-read it, but I had already hit send, and I was desperate, so whatever. Once again I was destined to endure the torment of waiting, not knowing if I would get any response at all. The wait this time was even worse, days went by with no response, I considered resending just in case my email was lost out there. Finally after a full eight days Jim’s name appeared in my inbox.
Skip-I guess we could think about doing this again, it would have to be a totally different kind of thing from last time a real quick strip kneel and suck. If we have to talk about condoms forget it. After I get off you can dress and leave, I’m not going to touch yours and I don’t want to have to watch you jerk off. If your in to that confirm you can be here at 5:00, you should be done and gone in 20 minutes or so.
I couldn’t understand why he was so adamant that I couldn’t get off but knew I would agree to almost anything at that point. My email went right back saying 5:00 is fine.
I spent the afternoon with a nagging partial to full erection, so hot for my second chance with Jim’s big cock. At 4:00 I started getting ready to leave, by 4:15 I was pacing and watching the clock, troubled by my unrelenting boner. I drove to Jim’s place fully hard, leaking copious pre-cum. I parked in front of his house, and made my way through the side gate to the back door. I found the back door open, with only the screen door blocking the hallway to Jim’s room. I could hear voices down the hall as I rapped on the screen door. I heard ‘C’mon in Skip’ from down the hall, so I let myself in.
The back door enters a hallway, it turns a corner to Jim’s room. Jim’s room opened on to the hallway, the bathroom was across the hall. As I turned the corner in the hall I found the door to his room open but the entrance was blocked by a woman leaning against the doorframe chatting with Jim, and apparently chatting with Laura as well from her laugh and the trace of cigarette smoke in the air. Tall and very thin, kind of a trashy biker look to her, with a rough mid — 30’s look to her. She looked over her shoulder and gave me a puzzled once over, a clear ‘What’s wrong with this picture look’. Was she wondering what a preppy 40 something guy was doing visiting Jim and Laura? Did she know why I was there, and I didn’t fit what she expected? Was I paranoid or did her gaze linger at the almost certainly visible tent in my slacks? Whatever it was, she made no move to step aside and let me pass, but returned her attention to Jim and Laura and continued her interrupted story, leaving me to stand awkwardly and impatiently in the hall. After nearly a full day of semi-erect anticipation I was very anxious to get in the room, but had to admit that her denim covered sculpted ass had my attention. That fact not lost on her.
‘Jim, this must be your friend Skip. From the looks of things my ass has him more than ready for you.’
I was snapped out of my daze to find I had clearly been caught with radar lock on her backside, and her own fixed stare on my crotch made it clear she had noticed my condition. In fact, apparently she was taking credit for my obvious arousal. But more startling was her comment, did she know why I was there? Did she have every detail of my last visit, or know the terms that had been dictated to me to earn a return visit?
‘I have to run, let’s finish this later in the week’ the mystery woman said to Jim or Laura. She turned toward me, her straining t-shirt showing an impressive bust, likely a C cup. She still made no move to allow me to pass, instead give a rather purposeful, lingering stare at my crotch. ‘Have fun’ she said with a smirk and strode by me down the hall.
Finally I had unfettered access to Jim’s room, but could only shuffle nervously to the door. I found Jim sprawled comfortably on his bed, Laura in her customary chair, both facing the television with some kind of afternoon television program on. ‘Well, you met Dee, my landlady,’ said Jim with a smile. ‘Real piece of work she is, huh.’
‘Looks like she was right about what her ass did to Skippy’ chuckled Laura with a gesture toward my trouser tent. ‘Or did you come through the door with the little guy hard?’
‘C’mon Laura, be nice to Skip this time.’ Jim said, though his amused grin made clear he found my state to be as funny as the women had. ‘I don’t mean to rush you Skip, but we have to be somewhere so why don’t you get started putting your clothes on the chair in the corner.’
I guess I hadn’t really thought it through, but only now did it dawn on me I was going to be naked, and apparently fully erect, for this process. That detail really hadn’t registered in a scene where Jim made it clear I wasn’t getting off, but now the reality of it was upon me, and my embaressment was almost paralyzing. I froze, my mind scrambling for an out, a way to maintain some dignity in this process. But I also found my gaze drifting to the pronounced bulge in Jim’s jeans, and that bulge was clearly winning the battle. I started to reach for my belt.
‘C’mon Skip, if you don’t get going we’re going to be out of time here…and I’m sure you don’t want that to happen.’ Jim’s tone had an edge to it, it was different from the nice guy tone I knew. The tone was effective though, I raced to get my shirt unbuttoned as I kicked off my shoes and socks. The shirt dropped to the chair, but now there was no delaying the inevitable. As I unclasped my slacks I knew my cock was as hard as it had been all day, but I had no options as this stage. I turned to the chair as I slid down the pants and underwear, stacking them neatly on the chair. I was now out of time and couldn’t will myself limp, so I slowly turned to face Jim and Laura.
Laura let out a rather loud guffaw. ‘It’s even smaller than I remember it,’ she gushed. She crooked a finger at me. ‘Come here’ she demanded, pointing to a spot immediately in front of her. I glanced at Jim, but he offered no assistance, so I shuffled over. In her low upholstered chair Laura was roughly level to my hard on, but from my raised vantage point I was looking down at a canyon of cleavage. My erection jerked and leaked. Laura glanced down at her v-necked window. ‘Not a chance’ was all she said with an amused sneer. Laura slid her hand in to the side slot of the chairs cushions and produced a 6 inch ruler. ‘Push it down so it’s level to the floor Skip’ Laura directed.
My humiliation was almost unbearable. I felt so naked, so embaressed by my erect state. But all three of us knew I would do it, and I did. With my index finger I pushed my shaft down to pointing straight forward, the touch and movement causing an involuntary sharp hiss from the pleasure.
‘Geez, don’t cum on me!’ Laura blurted out.
Finally speaking for he first time since I arrived I gasped out,’I won’t, I won’t, just don’t touch it!’ I blushed crimson as I realized I had admitted to all three of us I was dangerously close to orgasm, and we hadn’t even done anything.
‘Trust me, there is no risk I will be tempted to touch that thing.’ Laura choked out as she laughed loudly. She continued to chuckle but finally brought the ruler forward and rested the end against my groin area above my throbbing shaft. She leaned forward and squinted, and a broad smile spread across her face. ‘Almost 4 inches.’ she announced in an odd tone of triumph.
Jim finally took some control of the situation. ‘Ok, ok Laura, you had your fun…leave poor Skip alone. We really need to get going. Skip, get on your knees at the end of the bed here.’ His use of the phrase ‘get on your knees’ again had that new tone, and the choice of words made it clear this was an act of submission. But it was a step closer to getting some of his monster cock, so I dropped to the hardwood floor. ‘I’m going across the hall for a minute, why don’t you wait here.’ Jim climbed off the bed and sauntered out the door.
Laura clicked her lighter and inhaled deeply on a Marlboro Light. Her long purposeful exhale, followed by a second cheek hollowing inhale did little to ease the awkwardness. Finally she leaned forward and talked through her second exhale, her intentional posture drawing my eyes to down the front of her loose hanging shrit. ‘Almost 4 inches,’ was all she said.
Jim ambled back to the room, stopping in front of Laura as he slowly undid his belt. They chatted about their imminent dinner plans. His jeans slid down, and he stepped out of them revealing a pair of blue briefs. Laura got a look of mischief, and reached out to caress his hose through his briefs. ‘We could send Skippy home and I could take care of this?’ she offered. ‘You know I can do things he can’t do.’
I couldn’t help myself, it came out in a tone that was far too desperate. ‘No, No, Please’ I begged. Laura’s explosion of laughter made it clear that my pathetic begging was her goal all along.
Even Jim chuckled as he slid over on the end of the bed in front of me. ‘Stop tormenting Skip, he has suffered enough and we really need to get this over with.’
Now I was eye level to the front of Jim’s briefs, and for the first time the clear outline of his cock in severely tested blue cotton was about a foot away. I reached for his waistband, or maybe to touch the outline of his cock, I really don’t remember which. My own cock was now essentially vertical and painfully hard. But my reach was interrupted. ‘Now Skip, show some manners. When you met Dee a few minutes ago did you just grab her ass? We all know you wanted to, but did you d o it?’ I was confused, and wanted so desperately to get ahold of his cock. Jim continued. ‘Oh wait, Skip, one more thing. I don’t want you touching your cock while you are in my place. If we catch you touching or stroking I will shut this down in a minute. Do you understand? I don’t mean to be evil, but you shoot so fast we just can’t take the risk, so that’s the way it has to be.’ I didn’t know what else to do and my knees were starting to ache, but my ragged breathing made it quite obvious what kind of condition I was in. I just nodded dumbly.
But still I was stuck in the manners dilemma, and really didn’t know what I was supposed to do. I finally lowered my head and asked. ‘Can I please touch your cock Jim’.
‘Much better, see, you do have manners.’ Jim’s insincere praise was degrading, but I was long past caring. ‘Now, lower my briefs, but no touching. Any accidental contact and we call it a day.’
At this point I was completely off balance. What I thought this session would be was a total one way blowjob. He uses me as his whore, I get access to a huge cock. I couldn’t figure out what this was turning in to, but knew I had to keep pushing forward . I reached for his waistband, pulling it out with all the delicacy and caution of an electrician handling high voltage wire. Pulled well away from his body, I slowly lowered the waistband, gradually exposing the root of his shaft and progressing cautious inch by inch down his toward the head. Jim waited to the last second to finally lift his butt and allow me to slip the briefs down his thigh, completely uncomvering his thick, heavy hose and plum sized head.
‘Oh my god’ I rasped out in wanton admiration.
Unfortunately, the reveal of his cock was more than I could handle. To my horror I felt a surge of arousal that blew right past my ability to control it, and completely untouched I shot a blast of cum straight up in the air, landing on the bed next to Jim. The first spasm was quickly followed by a second healthy shot, then a third. At first I reached for my erupting cock in some kind of ridiculous attempt to stop my orgasm, but quickly remembered I wasn’t allowed to touch myself there and managed to stop my hands an inch from contact. I stared helplessly as my cum blasted forth.
For what seemed like eternity there was only silence, and I could only look down at my cock as it softened slightly and drooled some more cum. The silence was broken by the click of Laura’s lighter, out of the corner of my eye I could see her send a long plume of smoke toward the ceiling. ‘Skip, you are out of your league here.’ Laura said with no emotion, just a plain statement of fact. She took a long second drag and left me to suffer in the silence. Finally Jim shifted, bringing my attention back to him. He reached forward with his right hand and gently pushed me back by my forehead, back so I was sitting on my heels. My now nearly limp cock just hung, still dribbling cum. It looked smaller than I have ever seen it.
Jim stood, his cock hanging and swaying in front of my face. He reached down and pulled up his blue briefs, taking time to tuck his shaft to the left. Again the outline of the straining briefs was powerful. I groaned as it was now obvious I wasn’t going to get what I had come there for. Jim finally spoke. ‘Skip, get a towel from the pile in the corner and clean up the mess you made. Then take the towel and sheet from the bed and put them on the washing machine in the hall.’ I started to get up and reach for my underwear, but Jim clarified. ‘I said clean up this mess, you can get dressed after you are done.’
My panicked glance toward the door and hallway made it obvious what I was thinking. Laura saw her opportunity. ‘Yes Skip, he does mean go down the hallway naked. And yes, there is a chance Dee will be out there, it is her washer and dryer. Don’t worry, she has seen her share of dicks, more than her share actually. Probably never one that small…’
Jim interrupted. ‘C’mon Skip, we need to get going. Get this mess cleaned up now.’
I scrambled to my feet, my aching knees slowing me. There were three or four towels, cheap ugly greyed towels, in the corner. I took one off the top of the pile and returned to the bed. There were five or six major wet spots on the top and down the side of the sheet. Jim was now busying himself getting clothes to wear out that evening, but Laura was clearly watching everything I did. Again I was struck by my situation. I am a quite successful forty something executive. Completely naked I am being supervised by this early twenties girl, being supervised with utter disdain. And we both know I have to take it.
I wiped down all the wet spots with the towel, then pulled up the corners of the sheet and removed it from the bed. It reavealed an aging, cheap mattress. Balling up the sheet with the towel, I now faced the door. Laura arched one eyebrow, and with a subtle head nod directed me out the door. In a pathetic attempt at modesty I covered myself with the sheet and opened the door. The hallway was silent, it seemed the coast was clear. I walked down the hall and around the corner, seeing the appliances I had not noticed on my way in, right next to the open door to the backyard. I crept up as close as I could to see outside, the backyard was empty. I tossed the laundry on the washer and scampered back to Jim’s room.
As I slipped back in to Jim’s room I saw the evil look on Laura’s face I had now come to recognize. Jim was now oblivious to me as he continued to search his closet, back to me. I headed for my clothes, but Laura’s voice stopped me. ‘Skip, you missed all the cum you leaked on the floor.’ I glanced over, and sure enough there was a small puddle on the floor beneath where I had been kneeling. Knowing what I had to do, I reached for another towel to clean it up. Again, Laura spoke…’Uh, uh. We aren’t here to do endless laundry for you. Go get the towel you used.’ Her tone was very stern, but it was my mess and there was nothing I could say. I opened the door again and turned down the hall.
I made my way down the hall, glanced out the backdoor, again finding the coast was clear. I pulled the soiled sheet apart searching for my towel, after an eternity of naked vulnerability I found it and raced back to the room. Laura chuckled at my naked sprint in to the room. I bent over and wiped down the puddled floor, making a couple extra swipes for good measure. When I finished I reached for my underwear.
‘What are you doing?’ Laura barked. ‘Can’t you follow simple directions! Take the towel down to the wash, then you can get dressed…and wipe the drool off the end of your dicklet too! And hurry, we are so late!’
I looked down and saw what Laura was referring to, still stinging from her demeaning tone and the dicklet comment. A long string of cum was hanging from my cock, I wiped it with the towel, beyond being self conscious. I all but sprinted out the door, rounded the corner of the hall and tossed the towel on the washer from the corner. I wheeled and made it back in to the room undetected.
By now Jim was dressed for dinner, and was slipping on his shoes. I was struck by how ordinary looking he was, kind of out of shape with a poorly grown, thin mustache. It all seemed so unfair that because he won the genetic lottery and was so blessed with that marvelous cock he could get what he wanted. But finally I was allowed to reach for my clothes with no rebuke from Laura. My briefs and pants slipped on quickly, I felt slow and clumsy buttoning my shirt. Still Laura just watched, now even Jim looked on with impatience. I slipped on my shoes, and now stood awkwardly fully dressed. Not knowing what else to do, I extended my hand to Jim and thanked him for allowing me to visit. A disinterested ‘Take care’ was his reply as he loosely shook my hand.
Laura spoke up. ‘Time for you to go Skip. Sorry you didn’t get what you came here for, but I think you probably learned something today.’ Her meaning was obvious, as obvious as her meaning as she gestured toward the door. I stepped out and down the very familiar hallway, past my laundry pile and out the door. It was only then, as I walked around the house toward my car that I fully realized Laura’s meaning, that in all of the happenings of the last 45 minutes or so I never did get any part of what I came there for. Jim had shown me his huge tool, but my pathetic ejaculation had eliminated my chances of even touching it.
I got in my car and drove off, knowing I desperately craved another chance with Jim’s big cock, much more than I had before our meeting today. Also knowing my chances were practically zero, maybe less than that.
Laura’s words rung in my ears. I was out of my league. But I had to try.
My head was swimming during the drive home from Jim’s, now for the second time I remember very little of it. Jim’s big cock, Laura’s relentless and very effective humiliating control, Dee’s trashy but very hot look. Laura’s huge breasts and sensual smoking style. Jim’s new distant, directive tone. The image of Laura putting the ruler on my cock, and my falling short of 4 inches. My pathetic, ridiculous really, failure. I re-erected very quickly in the car.
Once home I once again deteriorated in to hours of repeated masturbation which yielded powerful orgasms. All driven by the images of Jim, of Laura, of Dee floating through my relentless fantasy bank. Once again it led to a collapse in to a sound sleep with a wasted raw cock, only to wake to a hard as steel drooling erection in the morning. I tried to resist the need to stroke off, hoping to organize my thoughts about the complicated experience from the day before, but was powerless to stop my hand from relieving it.
I made coffee, and sat staring at out a window at the forest behind my home. At first I couldn’t help but focus on the image of Jim’s thick hanging shaft and the enormous bulbous head of his cock. A sight I could only enjoy for a moment before he put it back in his briefs, clearly a gesture of punishment by depriving me. A larger image was becoming clearer to me though…yesterday I was completely naked, fully erect and drooling precum, and on my knees at his direction. He was mostly dressed, totally flaccid. In that moment his power was crystal clear, a power he exercised when he pushed me back and put away what he knew I wanted so badly.
I couldn’t help but compare that image to what I saw as I was leaving. Jim in a pair of old jeans, with a t-shirt hanging over a bit of a belly. His at best average looks in his sloppy one room place. But I also saw the look of indifferent arrogance, that he knew I would be begging for a chance to return. And Laura’s final words to me. In the midst of that mess, his home that would not compare well to many undergraduate dorm rooms with a bathroom across the hall, were two very average looking people. Two very average people who were blessed with an endowment that I desperately crave. And they know it.
As humiliating as it is, Laura was right, I am out of my league.
That day I opened an email addressed to Jim. I really had no idea what to say at this point, it had all ended so badly. Their last image of me was my scurrying around naked, cleaning up the mess my premature ejaculation had made and obeying their demand that I repeatedly go to the back door completely exposed. What recovery is there from that? Somehow saying ‘Had a great time, let’s do it again sometime soon’ wasn’t going to work.
Sorry about yesterday, I really am embarrassed, nothing like that has ever happened before. I hope you weren’t late for your dinner. After the last two times I’m sure you aren’t thinking you want to see me again, but I really hope we can try this one more time. Same as last time, total one way deal, will do it how ever you want and I promise I will do much better than last time. Please consider it, willing to work hard to make it work for you.
Clearly I was openly begging at this point, but I hit send. I really had no other options. I considered including an apology to Laura as well, but really couldn’t figure out what I was apologizing to her for…this whole situation is a mass of confusion, but I only know I need to get back there.
To my surprise, I received a response from Jim within a couple of hours. Even stranger, I found two responses from Jim in my inbox, sent about 15 minutes apart. I opened the one he sent first.
Skip- At this point I can’t really see much point in meeting again. I appreciate your willingness to do whatever I want, but I think you know there are plenty of guys out there who will give no reciprocation blowjobs to guys with big ones. I’m sure you understand. Jim.
His response didn’t surprise me of course, I appreciated that he did respond rather than just delete my email. But I couldn’t imagine what was in the second email, though I suspected it might be a copy of the first email that he accidentally double sent. I clicked the second email.
Skip- Laura asked that you email her. Her email is xxxxxxxxxxx. Jim.
I stared at the email for several minutes. I really had no idea what to make of it, but suspected Laura wanted to ridicule me further, what else could it be. Oddly, I felt my cock stiffening as I clicked her email address and opened a new window.
This is Skip, I was at Jim’s place yesterday. Jim told me that you asked that I email you.
I hope you weren’t late for your dinner yesterday.
My email felt really lame, but I had nothing to say or maybe I just imagined her reading it with the same look of disdain she has always given me. I hit send. To my shock a response came back within minutes. I took a deep breath and opened it.
skip I won’t waste a lot of time here I will get to the point. I know how badly you would like to give Jim head. Based on what I have seen I’m pretty sure you haven’t had a cock as big as his before and as you would know, SIZE MATTERS. HA-HA. I am offering you a simple deal. Just like before you strip, you get on your knees and you do as you are told and just like Jim said you don’t touch your dick. If you cum this time you can’t come back, and you will wear a rubber so you aren’t dripping everywhere. When you get here you strip, then you give me $50 and two packs of marlboro lights hard pack. That’s right, you are going to pay me so you can suck jim’s cock. Don’t waste my time asking questions we both know you will pay.
I re-read the email over and over. At first I was stunned, shocked…I couldn’t tell if I was angry or insulted or…I really have no idea how I felt. But very quickly I got over it. Very quickly I understood the door was open again. I read the email again, then again. My situation started to fully sink in. I was going to pay for sex. But unlike the way just about everyone else does it (I guess), I was going to pay for the right to give another guy sex. How did this get so convoluted…I offered to give another guy a total one way blowjob, what guy doesn’t say yes to that? But very clearly that is where we are…if I want to suck Jim’s cock I will be paying for the privilege. And I suspect I will need to be grateful…
Thank you for your offer. I will admit I was a little stunned, I had no idea Jim played for pay. But it’s all in good fun so why not. Of course I’ve never paid for sex before, but why not I guess. When is Jim available?
I guess I tried to save some shred of dignity by making this sound like it was all a fun game, and after I hit send I realized how dumb the whole thing read. I felt pathetic, but was also fully hard and knew I had to do this. Had to.
Minutes later I got a response from Laura, and if I had hoped to preserve some kind of dignity she had no intention of letting that happen.
skip jim doesn’t play for pay as you put it and you aren’t paying for sex because you aren’t going to get any sex. You are going to pay to suck jim’s big prick because you have to because you have a tiny one. You are going to buy me cigarettes because I can make you do it and you are going to leave here with your tiny dicklet hard out 50 bucks having swallowed jim’s cum. And the whole time you are going to work your ass off hoping we let you come back. It must suck to have a 3 ½ inch dick. Thursday at 5 don’t forget your rubber.
I could try to describe how I felt when I read Laura’s email, but there really is no point.
Thank you, I will be there Thursday at 5 and will bring the fee, cigarettes and condom.
I wish I could say I felt degraded or humiliated, but any of those kinds of reactions were overwhelmed by the unexpected chance to return to Jim’s place and get another chance with his cock. I guess my e-mail’s brevity was an attempt to diffuse Laura’s enthusiasm for slamming me, and I was admittedly surprised by her vitriol. While my attempts at being polite and professional while being forced to agree to pay to suck Jim’s cock seem ludicrous in retrospect, at the time it made sense. Again my inbox dinged. It was from Laura.
skip put the rubber on before you arrive I don’t want to deal with wrappers after you leave. Oh and since I know you were wondering yes Dee did know why you were here. That’s pretty funny if you think about it that you were checking out her hot ass and great tits and she knew you were a little dicked cocksucker. Yeah I did tell her about your little dick.
The two days of waiting were torturous. The cycle of three times per day masturbation wasn’t optional, but only reinforced to me the hold that the whole situation at Jim’s place had on me. What was becoming clearer was it truly was the whole situation, not just the power of Jim’s big cock. The elaborate requirements and fee reinforced that I was reaching beyond my station, Laura’s abuse wasn’t the rub, it was that she knew I had to take it. And yes she was right, Jim was the biggest I had ever seen live, let alone touched. What I am sure she suspected was that she also possessed that same kind of power if she ever chose to exercise it…her enormous breasts (I would later find out they were DDD’s) were many sizes larger than the biggest I had ever seen or touched. All of my life experience had been with small breasted women despite an obsession with larger cup sizes. While I crave D cups, only once had I experienced a B cup, all of my other experience had been with A or AA cups. All of the hoops I now had to jump through, and knowing any visit included desperation to be invited to return, led to a total collapse of my dignity.
But now I stood at my bathroom sink knowing what I had to do. My car keys, five $10 bills and two packs of Marlboro Lights were sitting by the front door. On the bathroom vanity sat a single Lifestyle snugger fit condom, the foil torn open. I knew that another unintended orgasm at Jim’s place would end my chances of visiting again. My only hope was that by jerking off just before I left I would have some hope of adequate control. My hand went to my limp cock, I closed my eyes and found myself thinking of Laura’s vast cleavage as she leaned forward to place the ruler over my hard cock. I found myself imaging her taking a deep, cheek hollowing inhale of her cigarette before announcing my sub-4″ erect length. And I heard my guttural moan as I splashed a small load on the back sink wall. I wheezed, and puzzled at the growing hold her sensual smoking had on me. I cleaned up and rolled on the small condom, and pulled up my jockeys. While it was still too early I couldn’t wait any longer, and climbed in to my car…cigarettes and fee on the seat beside me.
I purposely took a longer scenic route to Jim’s house, during the drive I felt my cock come back to life and extend to a semi erect state, loosely filling the condom. The feeling of the condom ring on my shaft wasn’t helping my attempts to keep control. When I arrived a few minutes early I was fully hard again. I tried to slouch a little and hide my tent, and made my way to through the gate to the back yard.
To my horror I found Dee in the backyard watering some flowers, once again dressed in biker chic…boots, very snug and flattering jeans and super snug top accenting her bust. She held the garden hose in one hand and a cigarette in the other. She looked at me as I closed the gate and a knowing smile spread across her face. She brought her cigarette to her mouth and took a long drag, then gazed at my slacks as she let a long slow plume of smoke drift my direction. “Back so soon Skip?” Such a simple phrase, but her smirk and her tone said so much more… I stood dumbly, after all it was her house. “You better get going, you don’t want to keep them waiting.” She paused, then her gaze shifted. “Did you bring presents?”
To my horror I realized I had Laura’s cigarettes and the money for the fee in my hand. I felt myself blush a deep red, and watched her gaze shift from my now obvious erection then back to my hand. I had no idea what to do, I think I mumbled something about needing to go inside and felt her stare as I hurried to the back door. Fortunately Jim must have seen me arrive because he called out from his room that I should come in as I arrived at the back door.
I opened the door and made my way past the now familiar washer and dryer and turned the corner toward the open door to Jim’s room. I could see Laura in her chair as I neared the door, now very conscious of my erection. Laura was flipping through some womans magazine and barely glanced up as I entered. She started in on me right away. ‘Heard you ran in to Dee. Bet she loved your little boner.’
Jim was once again sprawled on his bed idly watching a topless blonde with enormous breasts bouncing on a guy. Like Laura he didn’t look my way. ‘Hey Skip’ was all he offered. Neither of them said anything, just leaving me standing there as she continued to read and Jim watched the blonde.
Finally I tried to get some kind of interaction going, I turned to Laura and held out my hand with the money and cigarettes. ‘Should I give this to you?’
She didn’t even look up. ‘What were your instructions?’, she asked with disinterested disdain.
I couldn’t figure out what that meant until I thought I remembered the instructions said strip first, but didn’t want to start undressing and get rebuked again. ‘Should I get undressed first?’
Now Jim got involved. ‘Skip, put your clothes on the chair before Laura throws you out,’ he said sternly.
‘If you aren’t wearing a rubber don’t bother stripping. Just leave the money and the smokes and go jerk off.’ Laura added, still refusing to break eye contact with her magazine.
I undid my belt and unclasped my pants at the same time I kicked off my shoes. I stepped out of the pants and loosely folded them on the chair. I tried to remove my socks, nearly losing my balance and falling before tossing them on the pile. My polo shirt went over my head and on the pile, leaving only my jockeys. I had such an intense hard on that my waistband was pulled away from my abdomen, I wondered if my last minute jerking off session was going to help at all or if I was doomed to another premature ejaculation. I slid down my briefs and once again had to turn back to Jim and Laura fully erect. Neither looked up at my stiff condom covered cock.
I picked up the money and cigarettes and once again shuffled over and offered them to Laura. Finally Laura looked up, setting her magazine on the end table. Rather than take the fee, she first examined my hard latex covered cock which was pointing at her forehead. Both of us noticed that the condom tip was full of precum, a fact that clearly amused her. ‘Hand me the money,’ she instructed. I shifted the cigarettes to the other hand and gave her the bills. She unfolded them and very deliberately counted them, then equally deliberately refolded them. She crooked a finger and slowly slipped it in to her v-neck and under the edge of one bra cup. Pulling the white satin fabric away from her massive breast, she slid the bills in to the bra and out of view. Her finger slowly ran the length of the fabric down in to her cleavage. She knew exactly what she was doing. My condom covered cock lurched upward and I let out an involuntary moan. From the bed I heard Jim’s chuckle, but Laura wasn’t done. She now held out her hand and I proffered her cigarettes. She set them next to her magazine and picked up her ashtray and held it toward me without explanation. I took it from here and scurried to a trash can across the room and emptied it, then returned it to it’s place on her side table.
Finally Jim took some initiative. ‘Skip, get on your knees at the end of the bed,’ he said as he gestured to same position as my previous visit. I moved to the end of the bed wordlessly and dropped to my knees on the hardwood floor. Jim stood and slid off the athletic shorts he was wearing, but to my surprise was not wearing underwear so his huge hose just flopped free right next to the side of my face. I gasped in surprise, well out of pure lust as well, but did not move. Jim was now wearing only a dark blue polo shirt as he sat on the end of the bed and slid over in front of me.
I heard a lighter click as Laura lit a cigarette, but didn’t divert my attention from Jim’s cock. ‘Well he didn’t blow his load yet, he’s doing much better,’ Laura mocked. She didn’t stop. ‘Do you remember your manners this time Skip?’
She was right, I had managed to control my arousal, though I was rock hard and aching to cum. My voice was thick with arousal, so I had to clear my throat, which brought a chuckle again from Jim. ‘Jim, may I please touch your cock?’
Jim let my question hang out there for several seconds before answering. ‘Not yet. Mouth only, no hands, just work on my thighs and balls. I want both of your hands on the bed so I know you aren’t touching your dick.’
It felt very degrading, I don’t know why after all I had already put up with, but I put my hands on the bed on each side of Jim. I dove in with incredible energy, licking and sucking his upper thighs, fueled by my throbbing erection and desperate need. Eventually Jim guided my head to his balls. ‘Suckle each of them one at a time, go back and forth between them,’ he directed. I worked one of his hairy plum sized testes in to my mouth and gently suckled, amazed at the mouth filling size, then switched to the next plum. I switched between them at least a half dozen times, not daring to move to his cock. Finally Jim took my head and guided it downward. ‘Now work on the spot right behind the balls.’ I did as instructed, working my tongue despite uncomfortable reach, and was grateful that it smelled of lingering soap. My tongue started to ache, my jaw was getting a little sore when Jim finally gripped my head again. I was excited to finally be getting a chance to move to his cock, but Jim again directed me to his balls. He reclined and seemed to be enjoying my work, but his cock was still completely limp.
Finally I got what I wanted to hear. ‘ok Skip, still no hands, I don’t want you cheating, keep them on the bed where I can see them. You can start on my cock now. I want a lot of attention to the ridge around the head, not just pumping up and down.’
I had to adjust my position, get up off my knees somewhat to get my mouth on his giant cockhead, and sliding it in to my mouth with a heavy but completely limp hose took several tries. I started to reach for it with one hand at one point but Laura snapped me back with a quick ‘SKIP, uh-uh’. Finally I got it in and put my tongue to work on the ridge and slit, and heard a long pleasant moan from Jim. The size in my mouth was incredible, and I began alternating sliding down the shaft and working on his head with my tongue. I could feel the head and shaft thickening, growing in my mouth. I worked to a rhythm of pumping and tongue work that finally had Jim fully extended. I desperately wish I could have pulled back for a moment to see its fully erect size, but didn’t dare. I detected the first viscous saltiness of precum, but Jim didn’t appear to be moving toward any kind of advanced arousal.
‘Ok Skip, still no hands but start working on getting further down the shaft and I better not feel any teeth! You need to get down to the base.’
I was beginning to tire, was sweat soaked and my knees were screaming for relief. I felt very frustrated by the no hands rule, it really required me to work much harder. I began trying to get further down his shaft, but found myself gagging on the monster cockhead less than half way down. I tried again and again, but couldn’t even begin to get past the gagging. Finally I had to pull off after one particularly hard try. Laura was clearly enjoying my efforts and my growing exhaustion. ‘I don’t think he is going to be able to make you cum,’ she offered as I coughed .
‘Not at this rate he isn’t,’ Jim said flatly.
‘Your cock is so big, can I please use my hands,’ I pleaded.
Laura responded without hesitation. ‘You can, but it will be your last visit. We allowed you to pay for a blowjob, not a handjob. If you aren’t up to it you can finish with a handjob, but that’s only because once a man’s dick gets hard it needs to be relieved, he shouldn’t have to endure the discomfort of an erection without release.’
Her meaning was clear, as clear as my own straining cock. I went back to work, sliding my mouth back on to Jim’s pole.
I worked hard for another twenty minutes, the last 10 minutes trying to get past the pain in my jaw, my back and my knees. Finally Jim appeared to focus, and began moving toward a more aroused state. ‘Faster’ he demanded and I bobbed up and down as fast as I could. The first cum blast surprised me as Jim had not made any kind of sound, but its volume was mouth filling and slammed in to the back of my throat. I involuntarily started to lurch backwards, but Jim held me in place as the second blast unloaded, then a third of nearly equal size. I was gulping and gagging and swallowing, drooling a great deal of it down his still half dry shaft. Finally the sixth or seventh spasm was the last, and he eased his grip. I reeled backwards as Laura laughed, cum drooling down my chin on to my chest. Jim sighed contentedly, but then sent me to the same towel pile to clean him up. I stumbled awkwardly to my knees, they cried out from the pain of kneeling so long on the hard floor.
I took a towel and went to wipe my chin but was again rebuked by Laura. ‘Those aren’t for you!’ I stood foolishly with the towel halfway to my chin dripping cum, but resignedly dropped to my aching knees once again.
I hefted Jim’s now flaccid shaft and gently began cleaning around and over it. Finally having it in my hand caused my rigid dick to jump several times, adding to the now very full bulb of precum. When he was cleaned up I just stood, not daring to use even the soiled towel for myself, but not knowing what to do.
Laura set me straight. ‘You know where the towels go when you are done,’ as she gestured to the door. I realized she was sending me back down the hall wearing only a condom, but was resigned to doing as I was told. I opened the door and made my way down the hall, but even from a distance could clearly see Dee near the door continuing her watering. Before I could even think about turning back, Dee turned and looked directly at me. At me in my fully aroused glory. She made no attempt to look away, but just stared as I stood frozen. Finally I saw no option but to take another step forward and flip the towel on the washer, then wheel and scurry back.
When I came back through the door I found everyone returned to their original positions, Laura once again engrossed in her magazine, Jim once again wearing his shorts and watching television…now some baseball highlights. They both ignored me, and neither objected when I reached for my underwear. I still had Jim’s cum on my chest, but had managed to clean my chin adequately. I dressed quickly and silently, though awkwardly around my stiff cock. When I was dressed I turned to them and stood, finally squeaking out a thank you and walked out completely ignored. Mercifully Dee had finished her watering, and was nowhere to be found. I got out the gate to my car with no further incident. I started the car and drove about 1 block down Jim’s street before I pulled over in front of a white cape style house. As soon as I rolled to a stop I reached down and furiously rubbed through my pants, quickly unleashing a massive load in to my condom. The cum load overwhelmed the condom and spilled out in to my briefs as I gasped for a breath, a dizzy sense of some relief as a stain spread across my lap and my cock finally deflated.
I successfully serviced Jim’s cock, though the path was now clearly a brutal road of deepening humiliation that Laura clearly enjoyed, and Jim was increasingly an enthusiastic participant.. It took time, suffering and significant money. I was now on the side of the road with cum drying on my chin and chest, my body aching. I could feel my shrunken cock slipping out of the condom, spilling it in to my soaked jockeys and pants.
And I knew I would soon be begging for the chance to pay to be allowed to do this again.
After the meeting with Jim and Laura described in Chapter 3 I continued to meet with them on a regular basis. A process evolved where I would email Laura and ask if I could visit, and she would set the time. Eventually we settled in to a rhythm of meeting every couple of weeks. The deal stayed the same as what Laura laid out, I paid $50 plus the two packs of cigarettes each time. They always required me to wear a condom, and other than a brief hello I had to strip immediately when I arrived. As time went on things did relax a little and they weren’t as harsh with me, we did become more friendly. As we became more friendly I occasionally would put out gentle feelers about relaxing some of their requirements.
Once when Laura wasn’t there I asked Jim if there was any way we could forgo the fee, he and I had become friendly enough that occasionally we would sit and have a beer after he was fully serviced. While I appreciated the post coital (for him) camaraderie, it was a bit awkward as Laura didn’t allow me to get dressed until I was about to leave, the moment I was dressed I had to go out the door. She said it was a respect thing, who knows what that meant. So now we are two guys relaxing with a cold beer, Jim is fully dressed and I am naked with a condom on my still hard dick. Jim would often ‘apologize’ for my condition, telling me if I needed to dress and leave so I could take care of that he would understand. But I digress. So it is just the two of us, he had just had a particularly powerful cum and knew I had really worked hard for him. I had followed the usual guideline; strip and hand over the cash and Marlboros even if Laura isn’t there. We were enjoying some good football talk. So I tried putting out there thinking about a change in the fee arrangement. Jim smiled and laughed a sincere laugh. And with no hesitation he told me that if there was no fee there is no way he let’s me visit. One of his younger, well hung friends would be there in my place. Case closed.
Another time I tried to float the idea of letting me jerk off at the end of the session. More than once both Jim and Laura had let it be known that while Jim was pretty much exclusively no reciprocation with guys, he had no issue with them taking care of themselves after he was done. Oh, and of course they let me know none of them paid any kind of fee. So, again during a relaxed moment after I had fully serviced Jim, I tried to politely ask if there was any way they could let me relieve my very uncomfortable erection. The condom would be worn and it would leave with me, and I could go across the hall if they don’t like watching other guys pulling on themselves. Laura handled it this time, no hesitation, with a flat ‘No’. Admittedly I got a tiny bit pissy, I pushed back asking why if all the other guys get to jerk off and they don’t even pay. I knew I had made a mistake, and the look on Laura’s face changed instantly. ‘Get dressed and get out, maybe a couple of months away will help you remember your place.’ I emailed Laura for weeks afterwards pleading forgiveness, only to be ignored. Finally she answered my email, but was very cold to me. To make a long story short, our next session I arrived wearing a bra and panties under my clothes, and handed over a carton of Marlboro Lights and $100. I learned my lesson. Much later Laura shared that it makes her hot to blue ball a guy, and she loved forcing me to endure that kind of frustration.
I never saw Dee again and for that I was grateful, though Jim later told me that she did come to understand first hand why I was willing to pay for the privilege of being his cocksucker. And yes, he confirmed, she did know. Eventually she was essentially doing the same thing, when Jim lost his job she offered to reduce his rent dramatically so she didn’t lose access to his huge cock, though she managed to rationalize it some other way and Jim let her have her charade. After I had serviced him, on those visits when Laura wasn’t there, he loved to tell me about her incredible tits and ass, and how she couldn’t get enough of his cock. He knew very well what he was doing to me as I couldn’t resist probing for the details, but only was adding to the misery of my achingly hard cock. He loved to make me admit I wished I had the kind of equipment that could get a hot piece of ass like Dee. For that matter he loved to make me admit I wished I had a cock like his that would make other guys drop to their knees, rather than being the one paying to get on my knees.
After about 18 months or so I got an email from Laura telling me that she and Jim broke up. She shared some details and was a little upset, and did admit she would miss his huge cock more than anything else. Now, several years later they have both long since moved on in relationships, they both have moved a couple of times. But after a period of initial hurt, Laura recovered and eventually found she couldn’t fight it anymore. Less than a year after their breakup Laura started asking Jim to have sex with her again, no strings attached. This is clearly a pattern with Jim; ex.’s drift away for a while but eventually are back asking if he will please let them have his big cock again. Now Laura is basically in the same boat as me and a couple of other guys, she emails Jim and tries to get him to find some time for her.
After their break up I didn’t see Jim for a couple of months, I had lost his email once I was moved to exclusively going through Laura to set up time to see him. I really missed seeing him, knowing I couldn’t get anything even close to being in Jim’s league.
One day I found an email in my inbox from his saying little more than Hi, how have you been? I wrote a few lines of pleasantries, but then got down to it and asked if I could come visit again, the sooner the better. Like the early days, he didn’t reply for several days, probably knowing I would be there in 10 minutes if he gave me the green light. Finally after four days or so I got a reply from him. Again he had shifted to a cooler tone, didn’t say yes, but didn’t say no. Kind of said, yeah, we did have some good times and left it at that. I was out of my mind, and skipped all the other steps and went to begging for it. I told him how badly I missed his huge cock, how badly I wanted it, the same old deal or we could make changes if he wanted. I hit send.
A couple of days later I got a reply, a couple of very long days. I was certain I would get a reply, but knew he was making me suffer. Jim needled me about how badly I wanted his cock, letting me know he hasn’t noticed any shortage of really big cocks out there. Subtle, but I got it. But then he shifted gears. He said he would be willing to go back to meeting, but the terms would need to change a little, nothing too major but he will need me to continue to do some things that other guys shouldn’t have to do. Again, subtle but loud and clear. Basic terms would be similar, the fee would go up to $60, but I didn’t have to bring cigarettes for Laura. He did instruct me to continue wearing a condom, and was very clear that the ‘no touching, no cumming rule’ was in place. In fact he specifically told me not to try to revisit being allowed to jerk off.
Then the new terms started. Jim told me I was still to strip when I arrived, but he expected me to be fully erect when I arrived at the door, that he considered this to be a sign of respect. Failure would result in me paying the fee, and being sent back out the door. On the theme of respect, effective immediately, he would prefer that I not call him Jim anymore, that Mr. Smith would be more appropriate. Again, zero tolerance, so it became Mr. Smith from that day on.
Finally, he told me he expected me to move to a role of more total submission, frankly he didn’t need another cocksucker to add to his list, he got plenty of blowjobs. Oh to have such problems. From now on he expected me to wear black panties under my clothes when I arrive, more specifically black thong panties. He was very insistent that I have them on when I arrive, not put them on when I get there, and I will strip down to the panties when I arrive. He noted the thong pouch should show off my erection nicely.
To this day, those are the basic terms, and I do still see Jim. He has steadily come to enjoy taking advantage of the power of his big cock, regularly doing little things to reinforce we both know I have to do what he tells me to do. Sometimes it is little things like telling me to get him a coffee on the way over, or even to bring him condoms (Trojan Magnum XL) to restock his supply for ‘others that he meets’. He will often keep me waiting, hard and in my panties, while he talks on the phone or does some email, even giving me little chores to do around his place if he isn’t ready for me yet. But the only detail that really matters is that he still has that big cock.
Eventually I began to email with Laura again. She was always witty and fun and very bright. Well, and she had DDD’s. One day out of the blue she suggested we get together, she would enjoy seeing me again. I had no idea what she was thinking, but jumped at the suggestion. She sent me her address, told me to be there about 10 the following day. Oh, and one more confusing detail, she ‘reminded me’ to bring her two packs of Marlboro Lights and $50, and to wear a condom.
I drove to Laura’s place the next day as we agreed; she greeted me at the door with a warm hug and invited me in. She said something like ‘this is my place’ with a big smile, but with not a hint of awkwardness pointed to a chair by the door as the place to pile my clothes. She didn’t even stop, floating off to the kitchen as she asked if I wanted coffee. Thoroughly confused, I stripped down and followed her in to the kitchen wearing only a condom, clutching her cigarettes and money. She took them as if I had offered a bottle of wine as a dinner guest, then led me to the kitchen table to sit and have coffee. We chatted like old friends, only I was naked, as we drank coffee and she had a cigarette. It wasn’t long though before the combination of her deep v-neck sweater and her sensual smoking style had my cock stiffening, a process I was helpless to stop. The more I hardened the more I was drawn to her cleavage and massive bustline and inevitably was fully erect. While drinking coffee at the kitchen table. I will skip some details, but eventually I was on my knees on the kitchen floor, masturbating my condom covered cock with strict orders to keep stroking but not to cum. My other hand held her ashtray while she smoked and listened to me plead to see her breasts.
The request was denied, as was my pleading to be allowed to ‘finish’ as she called it, as always I left her place blueballed. I have seen her many times since, I have never seen her DDD’s nor does she ever let me get off. But she does delight in telling me what her well hung lovers get from her, things that I could enjoy too if it weren’t for being short just a few inches of what she wants. But the Laura story is another whole tale I could write several chapters on.
My meetings with Jim had been going on for about 5 years. In hindsight, it is amazing to me how much he had changed over that time. Five years ago he was an average looking guy with a bit of a belly who was bi-curious, and had no idea he was seriously hung. Chalk it up to being a grower not a shower, but his full 8 inches were really only the beginning of an incredible package, it was the nearly thick as my wrist shaft and huge incredibly well shaped cock head that made him world class in the cock department. And he had no idea. Our first meeting was supposed to be two guys meeting up to swap blowjobs.
Now five years later Jim is very different. His transformation really began when he and I met, and was driven by his cleverly malicious girlfriend at the time, Laura. She fully supported his exploring his bi interests, but immediately saw an opportunity when she saw my less than 4″ cock, and the effect Jim’s monster cock had on me. Laura told me months later that her number one turn on is using men’s desperation for sex to humiliate them. Laura quickly set up a structure for my relationship with Jim that remains the basis of how he and I interact to this day. She instinctively knew that I would be willing to pay a very dear price for access to Jim’s cock, and dictated the terms. She structured a total one way deal and total submission, knowing full well small cocked guys don’t get the time of day from guys who are much younger and real well hung. So it was her idea that not only wouldn’t Jim reciprocate, but I was not allowed to cum during a session. It was her idea that I strip naked at the door, and arrive fully erect. It was her idea that I wear a condom to avoid leaking strands of pre-cum. But most of all it was her idea that I pay Jim a fee, set initially at $50 and never really varying from that, to be allowed to get Jim off.
Ironically, all of this evil intention on Laura’s part worked too well. While I am sure she smiles to this day knowing Jim has taken thousands of dollars from me over the years for the right to give him hundreds of orgasms, every time ending with me leaving his place with an achingly hard cock that badly needs relief, it ultimately backfired on her. At some point early on, a switch flipped in Jim. Somewhere deep inside his dominant nature was unleashed, to the point that Jim now freely admits he can only get hard with someone who will do anything for him out of desperation for his cock. Laura and Jim split up about a year after I met the two of them, but within six months Laura couldn’t deny how much she missed his huge cock, his ability to cum over and over, and never ending stamina. She tried luring him back to a ‘friends with benefits’ arrangement of regular fucking, only to find a cold disinterest that could only be broken down with begging and total submission. Her DDD’s that could enslave lesser men failed her for the first time, and now Jim has her groveling for his cock the same as me and many others.
So here we are, almost 5 years later. Regular meetings, at least monthly and often twice per month. On a couple of occasions I tried to quit, usually because I would get disgusted and burned out on paying him. The reasons are complex, it isn’t just that it is humiliating to have to pay another guy to get him off however he chooses, but Jim also regularly reminds me that the other guys he meets with don’t pay him. So more than once I have become disgusted and tried to give it up.
Jim had long ago set an expectation that I would visit at least monthly, making it clear that he wanted to be able to count on the money. In fact on a couple of occasions he subtly made it clear that he expected to be paid on months where schedules didn’t allow us to get together. Nothing too obvious, but when I was anxious to get together after more than a month without his schedule suddenly got problematic, problematic until I had no choice but to offer the previous months fee with the normal fee I had to pay to get his zipper to come down. So a couple of times I did try to quit. I told him each time I needed to find a way to stop; I was respectful and didn’t just disappear. Each time he was amused and condescending, immediately laying out what his expectations would be when I broke down and came back. The terms were pretty simple, I would have to pay the fee for each month I missed and should expect to be wearing panties for a long time in future sessions. Each time I would start out determined and convinced I could do it; eventually I would find myself masturbating regularly thinking about his huge hard cock, inevitably sending him an apologetic email asking to be allowed to visit him again. Once I made it 4 months. Jim thoroughly enjoyed watching me kneeling in front of him naked, my small cock hard as steel, as I counted out $200 for the months I had missed, then counted out $50 more for that day and began begging to be allowed to service him. Only later would I come to understand how seriously he took the money aspect of our business.
On two occasions I even tried to find a replacement for Jim.
Each time I found myself hunting for something that described Jim to a tee…about 10 years my junior, hung long and very thick. I described myself as fit and little younger than strictly accurate, added an inch to describe a 5″ well shaped cock and was more than willing to do a no reciprocation deal for the right guy. I met up with a couple of guys, each one had supplied picture proof of large, powerful cocks, and each one then insisted on a live meeting to check me out. While the details were a little different each time, the result was always the same. I met this one guy Steve at a local shopping mall. We sat in the back of his very private van to talk, and he quickly directed me to fold all of my clothes neatly and put them on the front passenger seat. Steve, a good looking guy in his mid-30’s, was fully dressed and it was obvious he intended to stay that way. He was looking for a ‘regular guy’, someone who was available at his whim to strip down and provide a very long, slow patient blowjob. His requirements were consistent availability, stamina, and an understanding that he doesn’t want any jerking off or stroking of my cock at his place. ‘Last thing I need is you getting too excited and having an accident, guys are useless after they cum’ was how he put it. I tried to play it cool as we talked, but my cock kept getting progressively harder and I was helpless to stop it. By the time Steve finished describing what he was looking for I was fully and embarrassingly erect.
‘So that’s 5 inches huh’ Steve asked with both clear skepticism and amusement.
I knew I was stretched out as long as it could get, and hoped the missing inch or so wasn’t obvious, but it clearly hadn’t fooled Steve. ‘Almost’ I mumbled.
‘I guess most guys with little ones lie a little, huh?’ he asked with clear disdain. He let the silence hang painfully, making it clear he expected me to admit the obvious.
‘It’s almost 4 inches’ I said in a low voice, desperately trying to find a place to look as I avoided looking at him, but didn’t want to just look down at my bobbing cock. However, I couldn’t help noticing, to my horror, a large well formed drop of pre-cum had formed at the end of my cock. Steve clearly noticed too as he chuckled.
‘Can we get to a real number, or are we going to keep playing games’ he said impatiently. By now the whole dynamic in the van had changed. I probably was trying to deny the obvious when I stripped down at his direction, but Steve was clearly in charge now.
‘3 ¾”‘ was all I could say in a low voice. The drop of pre-cum started to string downward off my cock, I was paralyzed by the humiliation of the situation.
‘Take care of that, I don’t want it on my seats’ Steve directed sternly. I scooped it up awkwardly with my fingers, but sat there awkwardly with cum streaked fingers. Steve was losing patience. ‘Let’s go, put it in your mouth’ he snapped. I did as I was told.
While the ‘interviews’ were all different, one guy actually put a ruler on my cock and had me read my measurement to him, they always wrapped up the same way and Steve was no different.
‘Ok, so let’s talk about how the money will work.’ Up until now there had been no reference to money in any email or discussion, but as one of the guys told me pretty bluntly ‘Older guys with little dicks don’t get in the game without cash. There are plenty of young guys with six packs who will give no recip blowjobs if you have a big cock, so saying you will do no recip doesn’t get you anything.’
Steve proposed that $20 an inch sounded fair, so sucking his 8″ cock would cost $160. I tried to counter propose that I pay $20 for each inch of difference between my cock and his, and proposed $80 would be a fair result.
Steve laughed at my math for starters, pointing out I don’t have a 4″ cock so my proposal is actually $100. ‘The only reason I care how big your dickie is because I know guys with 3″ cocks don’t get guys with 8″. I’m not going to let you pay for the difference because I’m never going to touch your dick.’ In every interview, sooner or later we got around to an expectation of a fee being paid.
I did pay Steve that day, it wasn’t $160, he took the $120 I had with me and when he lowered his jockeys an impressive cock was revealed. Long, medium thickness with a proportionate if only a little undersized head. In other words, he wasn’t in Jim’s league.
So, inevitably, I would return to Jim every time.
While we had developed a friendly rapport, Jim and I weren’t friends, and our roles in the relationship had become very firmly established. He was affable and pleasant, but was very clearly in charge. It was understood that I would treat him with deference and complete respect, and by now it had been several years since I had called him anything but Mr. Smith. I always paid him as the very last thing I would do when I was leaving. I was always dressed and ready to leave, with my slacks clearly tented by my hard dick, but early on he had made it clear he expected very enthusiastic and sincere thanks when I gave him his fee. That might have been the single most difficult requirement in each meeting, all I can think about is how badly I need to cum and ease my aching balls, and I am handing him cash and thanking him knowing his huge cock is hanging limp and satisfied after a couple of quality orgasms.
The rules of our meetings had changed very little over the years, and had settled in to a ritual that was understood and comfortable to both of us. While at one time he had forbidden me to email him and ask for a meeting, he had softened on this rule and generally now it was me who initiated setting up time. Usually he permitted me to meet without requiring me to wear panties, only occasionally did he re-establish this rule if I had displeased him by having to cancel a meeting or not visiting him as often as he preferred. But when his email saying we could meet included a color choice for the thong panties I had to wear, the message that he wasn’t pleased was loud and clear. But the core ritual remained the same for each meeting.
First stop was a local Walmart where I would buy the panties if required, one box of 12 Trojan Magnums, and a package of 3 Lifestyle snugger fit condoms. All of these purchases needed to appear on one receipt that I had to give to Jim with his box of Magnums to prove I bought both sets of condoms at the same time. And yes, if you are wondering, you do get an occasional odd look when you are buying two sets of different sized condoms at the same time, and I have little doubt that the clerk can guess which box is for me. In the parking lot of Walmart I would wriggle out of my pants and Jockeys, pull on the thong panties and awkwardly pull the pants back on. And yes, embarrassing as it is I do generally get hard putting the panties on.
Stop number two is a Dunkin Donuts near Jim’s home. I always go in so I can use the men’s room. Jim doesn’t allow me to use the bathroom at his house, so I take a nervous leak so my bladder is completely empty. I order Jim’s coffee…large iced coffee, light with six Splenda. Summer or winter, doesn’t matter, iced coffee it is.
Stop number three is a small shopping strip mall right around the corner from Jim’s home. I park in the far corner of the parking lot and carefully watch the clock until it is exactly 10 minutes before our meeting. Jim has always insisted on strict punctuality. At 10 minutes to I unzip my fly and begin rubbing my cock through my underwear, stroking to the full erection that Jim requires when I arrive at his door as a show of respect. Usually this isn’t difficult, though sometimes the stress of all of my chores and racing to arrive on time keeps me stubbornly limp, but somehow I always manage to get to my full 3 ¾” in time. Fully fluffed, I drive the quarter mile to Jim’s home with one finger tracing my erection to keep it fully hard.
So just like any other month, I had emailed Jim two days ago requesting a meeting. He sent back a time when he was available, and had suggested I wear black panties. I was surprised because I couldn’t think of any reason why he would be irritated with me, but I suspected he was just doing it to reinforce his power. He knows I hate having to slip in to the lingerie department and find panties that match his request, then arrive at a cashier with boxes of condoms and panties. For the same reason he often likes to tell me to pick up some things on the way, mostly because he enjoys reinforcing that I have to do it. Usually they are mundane things like a twelve pack of soda or cigarettes for one of his girlfriends who wears a DD bra. Today’s meeting had a new quirk. I had emailed the day before and asked if we could meet the next morning. Jim had instructed me to bring an additional box of 6 Trojans in standard size…so three sizes of condoms all on one receipt. I had followed his instructions, and clearly got an odd look from the Goth like 19 year old chick behind the counter as she scanned box after box of condoms and a black satin thong in size XL. I half expected her to ask if I had no idea how big my dick is. I assumed his request for regular sized condoms was so he could replenish his supply for his hung average friends, Jim has always enjoyed reminding me that I buy his condoms for the women and other guys he sees, hence the requirement of the 12 pack when he only uses one or two with me. So making me buy condoms for other guys I figured was just another way to screw with me.
Our meetings are always first thing in the morning, Jim has several extremely busty women friends who he sees regularly in the early afternoon, so he slots me in to early mornings so he can recharge after having me get him off a couple of times. This can often make the morning errands stressful, especially if he adds a few things to the list, but Walmart opens at 7 so I always get it all done. So like any of many, many meetings with him, I arrive at Jim’s precisely on time, finger working the length of my hard cock, parking out in front of his home. I knew from experience that there would be a quite noticeable wet spot in the black satin, and the thong back had worked its way in to my ass in a way that I was now quite used to. Today I had forgotten to check if I had exact change for Jim’s $50 fee, arriving with three twenty dollar bills means I will be paying him $60 because the thought he would give me $10 back is laughable. So I shuffle through my bills quickly and am relieved to find a twenty and three ten’s. I gather the Walmart bag full of condoms in three sizes, give my cock one last stroke knowing once I get out of the car it will be off-limits, and grab his coffee and make my way to his door. Hands full, I push the bell with my knuckle of my hand holding the condom bag, though more than once I have amused myself by wondering if my hard dick could make the uncommonly low doorbell button depress sufficiently to alert Jim I had arrived. Likely it could.
Jim arrived at the door in his usual attire for one of our meetings…a baggy pair of sweat pants and a faded old t shirt in stark contrast to my being dressed for work.
He is always friendly enough in a superior sort of way, offering an indifferent ‘Hey Skip’ at the door in a ritual that begins our now standard opening conversation.
‘Hello Mr. Smith, thank you for letting me visit.’ Is my stock answer. I always, even after all these times, feel a little awkward and stressed at this point, much of it probably a result of being incredibly horny and having a full erection. I hand Jim his coffee with a mumbled ‘I hope it’s the way you like it’. He would never thank me for it or show any kind of gratitude.
There is a chair to the immediate right of Jim’s entrance door, and it is well understood that I will immediately strip down, neatly folding my clothes and putting them on the chair in a precise pile, with my shoes on top of the pile. I hand Jim the bag full of condoms and hurriedly start to get undressed. Jim gets impatient if I take too long, and is very critical if I don’t fold and stack my clothes neatly enough. But today he is quite pre-occupied studying the receipt and the boxes of condoms. As usual I can hear a television in the background, Jim usually has porn on the television when I arrive, I often wonder if porn just plays 24/7 here.
Jim is still studying the receipt for the condoms. ‘These things are expensive,’ he exclaims with a low whistle. ‘Glad I don’t have to buy them.’ By now I was finishing folding my pants and putting the shoes on top of the pile, and chose to ignore the unsubtle little zinger, but he kept going. ‘You know, I have always been surprised that your size condoms and mine cost about the same amount. Wouldn’t you think mine would cost a lot more?’ Jim was only getting warmed up. ‘It does make sense the standard size costs less, there is more demand. I guess there are very few guys who are magnum size, and even fewer who need these fitted things. Look, you can tell, the box for the fitted ones is even a little dusty.’
Jim seemed to be consumed with the thought, but then snapped out it and looked down toward my pre-cum soaked panties. ‘Pull the waistband down under your balls, let’s head back.’
Head back meant toward the back bedroom, which is down the hall and through his family room. The waistband command was new, usually I just wear the panties back to the bedroom, then he has me take them off right away. But it became habit a long time ago to just do what Jim tells me to do, so I slipped the waistband under my balls as instructed and started to follow Jim to the back of the house. There is some odd and embarrassing about walking when you have a full hard on. It juts out and bounces, and makes it clear that you are aroused. It gives the other person power because there is no hiding that you want it. I couldn’t help glancing down, and to my horror saw a string of pre-cum starting downward from the end of my cock. I was in a panic. Jim gets very angry if I drip pre-cum, generally when we get to the bedroom he has me put on my condom so I don’t get pre-cum on anything, I do tend to flow pre-cum heavily. But his strictest rule is that I cannot touch my cock when I am at his place, so I didn’t dare reach down to stop the string. The only exception to the ‘no touching your cock’ rule is when I put my condom on, and Jim always watches carefully to ensure there is no excessive handling involved. So the string kept extending toward the floor and we kept walking toward the sounds of a woman delivering a blowjob emanating from the television in the next room.
I was very distracted by my leaking cock which explains why I almost ran in to Jim’s back when he unexpectedly stopped in the family room, though the near collision did solve one problem when my jutting cockhead wiped on the back of his sweatpants. Jim had no idea that he helped me out, but was quick with a snappy line….’Yeah right Skip, with that tiny cock you will always be on the receiving end of that kind of action…’
The family room in Jim’s place is, like the rest of the house, untidy and poorly furnished. Laundry and dirty dishes are part of the decoration in every corner, and piles of stuff are everywhere. The family room is dominated by one large recliner that I have always thought of as Jim’s throne, and have spent a great deal of time in front of it on my knees. A plaid sofa sits next to the recliner, and both face an old style 50 inch or so projection television. It really is appalling how bad the picture quality is once you have become accustomed to today’s high definition flat screens, or maybe it is the poor quality of the DVD that is playing, but the balloon titted blond bobbing on a huge prick still grabs your attention even with the cheesy soundtrack. So, as my head involuntarily swiveled toward the screen I was stunned by what I saw.
There, sitting on the ugly plaid sofa watching the big titted bleach blonde, was another guy. I was probably standing three feet from him, directly behind him, with my stiff cock pointing right at him at head height, and my balls presenting nicely forward courtesy of the panties tucked under my balls. In all my meetings with Jim there had never been another guy present. In fact, not since our early meetings when his girlfriend Laura used to watch, there hadn’t been anyone else in the house when we met. But there he was. Of what I could see he was an average looking guy, 30’s and an ordinary soft body type, wearing the same sweatpants and t-shirt uniform Jim was wearing. Looked like he was accustomed to long hours on plaid sofas. But I could only see so much.
Jim spoke. ‘Hey Bill, this is Skip that I told you about.’ God only knows what he told him, but since I am meeting this guy Bill in a black thong with a hard on, what is there left to tell? ‘Skip, this is Mr. Taylor.’
Bill looked up briefly at my face, but quickly locked on to my thong supported cock, hard and horizontal and beginning to form another pre-cum drop. Bill laughed loudly and spontaneously. ‘Hey Skip.’ Bill briefly looked away from my drooling cock. ‘You weren’t kidding; he really is your bitch isn’t he. You weren’t kidding about his dick either, that thing is ridiculous!’ I don’t know if I have ever felt more awkward, more naked, than I did at that moment. Meeting a fully dressed guy when you naked and erect is horrifying I was learning.
There was an awkward silence, finally Jim spoke. ‘Skip, where are your manners, can’t you say hello.’
I had no idea where to look; I was mortified by the whole scene, but couldn’t just stare at my feet because the 3.5″ object of Bill’s amusement was in the way. ‘Hello Bill.’
Jim quickly snapped the back of his left hand in to my balls, not overly hard, but I never saw it coming and it stung with that low dull ache that only a shot to the balls creates. ‘Is that how we treat friends of mine Skip? Is that how I taught you to act in my home?’
The ball strike quickly took the breath from me and doubled me over, but I managed to somehow to keep from grabbing my balls. Breaking Jim’s strictest rule against touching my cock and balls was out of the question. I straightened up, and tried again, grimacing through the ache. “I’m sorry Mr. Taylor, hello Mr. Taylor.’
‘Much better,’ Jim said. He turned to Bill. ‘I’m sorry you had to see and hear that, believe me, he will be much more respectful from now on.’
By now the scene on the television had moved on to a two fisted hand job, the blonde’s tiny hands travelling up and down an enormous oiled shaft as a long haired guy mumbled his approval, the relentless soundtrack blaring. Bill returned his focus to the screen, ignoring Jim and I.
Jim took over. ‘Skip, this is how it’s going to work. Bill here, well Mr. Taylor to you, is a buddy of mine visiting from out of town. We got talking last night while we watched some new porn, and he told me he was horny as hell and needed some, that he hasn’t had any in weeks. I can’t remember the last time I went a few days without…so I guess I understand. So I told him if he sucked me off during the movie and paid me $20 he could use you this morning. It was either that or let him tag Elise this afternoon, and that’s not going to happen.’
I audibly groaned at the mention of Elise, Jim heard it and smiled. Elise is in her late twenties, average to bordering on homely looking, at least from the pictures I have seen. But she has an insanely hot body…5’7″ or so, shoulder length coal black hair, womanly curves and a set of 36 DD’s that could make a man weep. And she can fuck for hours, at least she can and will if you have an 8″ long incredibly thick cock. And Jim loves to remind me about the last part; her bra doesn’t come off for small to average cocks.
Jim turned to Bill. ‘And nothing happens until I get the $20 loser.’
Jim returned to me. ‘So you are going to go in to the guest bedroom with Mr. Taylor and do whatever he tells you to do for the next couple of hours. Or you can leave, and never come back.’
Bill handed a $20 bill over the back of the sofa without looking away from the television. Jim took it, and returned to me.
‘So your choice. But fair warning, if you go in that bedroom Bill better come out of there saying you were fantastic, that he is completely satisfied, or you never come back here again. Do you understand me?’
I was horrified, and my mind raced, coming up with nothing.
‘I want an answer now…Bill’s dick is waiting’ Jim demanded.
‘Ok’ I mumbled but quickly caught myself. ‘Yes, Mr. Smith.’
Jim smiled an evil smile. ‘See I told you he was a slave to my cock’ he gloated to Bill. ‘But then so are you slut’. Bill gave him the finger without looking up.
Jim continued. ‘Ok, Bill, here are the ground rules. Skippy here wears a condom at all times; I don’t want him drooling all over my place. Skippy is never, ever allowed to touch his cock. And he is absolutely not allowed to cum, do not let him tell you it was an accident or some bullshit like that. After that it’s up to you, and he can pay me my $50 on the way out. After he leaves you can give me a report to see if he gets to come here again.’
I was astonished to hear that on top of getting sold to Jim’s friend as a fuck toy I had to pay him the usual $50 fee, but kept my mouth shut. Jim took a long drink of his iced coffee.
‘What will it be Skip?’
I knew, and both of them knew, that I couldn’t walk out and lose access to Jim’s cock. I suspected he didn’t mean it, he would still want the cash and let me come back, but really couldn’t take that chance.
‘I’ll do it’ I mumbled. Jim seemed to pretend he didn’t hear me, and Bill was still hypnotized by the big titted blonde. I spoke louder. ‘I’ll go in the guest room with Mr. Taylor.’
Jim refused to give me any kind of positive reinforcement. He took that box of Trojan magnums out of the bag and tossed the bag at my feet. ‘Put a condom on, then lick your pre-cum off the floor you pig.’
Even for Jim this was harsh talk, he is usually very pleasant, but he hates pre-cum. ‘Yes Mr. Smith’ was the only answer I could offer. I tore open my box of Lifestyle fitted condoms, and tore the foil of the first one, sliding it out of the packet. I knew Jim was watching closely as I fitted it on my cockhead, and rolled it down my shaft. I did it quickly and pulled my hands away quickly so he wouldn’t accuse me of giving myself some pleasure, but even at that the sensation of the ring rolling down my cock almost made me cum. My sharp intake of breath gave me away, and Jim laughed softly as I fought to hold my load. Successfully fought to hold my load, but it was a struggle. I looked on the floor and did see several wet spots, I had to assume they were pre-cum. The thought of licking them up was repulsive, Jim’s housekeeping standards were non-existent, I’m sure that floor hadn’t been washed in years. However, when I looked up to see if Jim was just kidding about the lick it up command, not only was he watching with obvious amusement, but Bill had stopped watching the television long enough to watch too, and obviously was enjoying this.
I leaned down to the floor, stifled a brief urge to retch, and licked up the first filthy wet spot. I pushed on quickly, thinking if I stopped I wouldn’t be able to start again, and licked up three more spots. I thought I was done, but Jim’s foot pointed toward one more spot, and I licked that spot too. It was horrible, but I was done, but I also realized that my submission had been well demonstrated for Bill before I went in the room, and it was made clear to him that I would do what I had to do to stay in Jim’s good graces. Of course I also knew that Bill had experienced Jim’s cock first hand, and knew well the effect it has on a man.
At this point, for the first time, Bill began to take over. He was still quite distracted by the blonde whose breasts were now bouncing cartoonishly as she rode the well hung guy hard, but was able to begin to take control.
‘Skip, pick up the condoms bag and hold it in your teeth. Crawl on your hands and knees down the hall, go in the second door on the left. Wait in the middle of the room at the end of the bed in that position until I get there. Go.’
‘Yes Mr. Taylor’ was all I said, just as I knew that yes, Mr. Smith would be the only response if Jim had given me that direction. I grabbed the bag with my teeth and crawled down the hall, turned in to the unfamiliar guest bedroom with a single twin bed and little else besides piles of stuff, and waited on my hands and knees on the hardwood floor.
The wait was lengthy, about 20 minutes, and the oak floors were making my knees ache. The bag was very uncomfortable in my teeth and I couldn’t stop some drooling on the plastic. My erection had fully subsided, and the condom weighted with pre-cum was just barely hanging on to my shrunken penis. I was keenly aware that the view to the hall was my ass with a black thong that had worked its way well in to the crack. In the distance I could hear the television sound track, and could hear Jim and Bill laughing, presumably at least some of the laughter was at my expense. I couldn’t help questioning why I was doing this, then cursing Jim for being blessed with such an incredible cock and knowing I had to get through this. Over the years I have known Jim this thought has consistently haunted me. He isn’t a particularly brilliant guy, very average looking, isn’t in great shape, he works very little, just enough to pay his rent. But he won the genetic lottery and has this monster cock. His taste runs to very large breasted women, and an occasional completely submissive man. It isn’t that he likes men per se, but that he enjoys humiliating other men with his cock. And he gets away with it, in fact has difficulty scheduling. And at less than 4″ I am on my knees on the floor, as usual.
Finally, Bill made his way in to the bedroom. He wandered in, and stood for a moment taking in my situation. ‘Move forward Skip’ he said with a tone of easy authority. I scooted forward, and heard the door close behind me. Bill moved over and sat on the end of the bed facing me, and after a long silence finally spoke. ‘Up on your knees facing me, hands behind your back, eyes down unless I tell you otherwise.’
I scrambled to my knees and assumed the position, bag of condoms still in my mouth. Bill made no move to take them, or do anything else. He just let me kneel and wonder.
‘Lean over put the condoms on the bed’ he said. I leaned and dropped them, feeling the ache in my jaw as I did.
He continued. ‘So how long have you known Jim?’
‘About 5 years’ I replied, eyes still down.
‘And how often do you see him over that time?’ Bill asked.
‘Once, sometimes twice per month.’ Still looking at the floor.
Bill continued his interrogation. ‘And how much do you pay him for a visit?’
‘$50’ I mumbled.
Bill was enjoying this. ‘So you see him 15-20 times per year, let’s call it 15, about right?’. I nodded, he continued. ‘You pay him $50 per visit, have you paid him that right from the beginning?’
‘Except for the first time, yes.’ I answered more loudly now, resigned to telling him what he wanted to know.
‘How did you start paying him?’ Bill asked.
‘It was his girlfriend Laura’s idea. She told him that a guy with a cock as small as mine can’t get a really well hung guy without paying for it. Well that and he is 10 years younger than me, so she set it up that way’.
Bill laughed. ‘That sounds like Laura, manipulative bitch. But she has a talent for working guys over I will tell you. The panties were her idea too, weren’t they?’
He was right, but I couldn’t figure how he knew that. ‘Yes, but how did you know Mr. Taylor.?
Bill laughed. ‘She loves to make guys cross dress, you would be amazed how many guys have ended up in a bra and panties hoping to get a shot at those gigantic boobs. None of them have a shot unless they are hung like a donkey. More than one guy has had to buy pictures she took of them back from her. Bitch’
I suspected Bill had been one of her victims.
‘So wait, let’s figure this out. You see Jim at least 15 times a year, times $50 a visit, that’s $750 a year. Times 5 years, that’s at least four grand. I’m guessing Jim shoots two loads per meeting…about right? ‘ He didn’t wait for my answer, he knew he was right. ‘So you have paid four grand to get Jim off about 150 times. And how many times have you cum during all this?’
I was certain Bill knew the answer, but had no choice. ‘Once. I accidentally came once during our first meeting.’
Bill was loving this. ‘And you know there are plenty of guys like me who are blowing Jim for free, right?’ I nodded, head down, he continued. ‘So why are you paying four grand, FOUR GRAND, to suck another guys cock that other guys suck for free? Tell me!’
I was stunned by the math, four thousand dollars, probably more. More than 150 loads of Jim’s cum, probably more like 200…but I had to answer. ‘Because Jim is a lot younger than me and his cock is more than twice as big as mine. But mostly because he won’t let me unless I pay him.’
‘And why do the rest of us suck him for free?’ Bill asked in the most condescending tone possible.
‘Because the rest of you have bigger cocks than I do’ I gave him the answer I knew he wanted.
‘Eyes up.’ Bill commanded. I looked up, Bill was sitting with a look of mission accomplished on his face. He had made his point, that even though he might not be in Jim’s league, he was still a superior man to me. He stood up and slid down his sweatpants, stepped out of them and kicked them aside. He stood with his blue briefs inches from my face clearly tented by an erection. Clearly all this conversation had affected him, or maybe it was just a holdover from hours of porn. Embarrassingly enough, my own cock had stiffened again from all the conversation about sucking Jim, and it pointed straight out, condom clad. Bills tent in his briefs was not particularly impressive, I had to admit I was disappointed.
Bill sat down and leaned back supported by his arms. ‘There is no getting around the size thing is there? Jim has that huge one, chicks flock to him, friends of those chicks do him behind their friends backs, his friends wives call him for some. His ex’s all call him to get fucked, even if they can’t stand him anymore. Laura was here two days ago, she didn’t think it was funny that Jim didn’t tell her I was here, but she still ended up in his bedroom for a couple of hours. It’s ridiculous. Guys line up to suck him off, and not only doesn’t he suck but he won’t let the other guy jack off. Believe me, I was hating that rule here last night after a few hours of drinking beer and watching porn and sucking him off a couple of times.’
By now my erection was like steel, and Bill clearly noticed as it pointed nearly vertical.
‘But then there are guys like you who have to pay to be Jim’s bitch. How small is that thing again?’
‘Almost 4″, about 3 ¾”‘. I was hoping the talk would end soon, Bill clearly had accomplished his goal.
‘Wow, no wonder he makes you pay for it. You know you are the only guy who pays him don’t you?’
There was something odd in the way Bill said I was the only guy that paid him, and before I even thought about it I blurted out ‘Do any of the women pay him?’
Bill looked surprised. ‘You don’t know?’
He hesitated but my look made it clear I had no idea what the answer was. ‘Yeah, a lot of them do. Most of the women who started out as friends of a friend pay him, usually because they have small boobs and he isn’t in to that. So, like C cup or less pays for it. I think they pay about the same amount as you do. Of course they all get to cum, probably like a dozen times each once he gets going. He has one rich bitch who pays him a lot, like $200, she is a skinny old chick, 50 something with no boobs. That’s why he doesn’t work, he doesn’t have to. And all the ex’s pay for it, even Laura. That’s why she started seeing you again, didn’t you know that? ‘ I shook my head. ‘Yeah, she was in grad school and had no money but Jim told her no pay no play. Jim suggested she get the money from you, so long as she didn’t let you see or touch her boobs or get off. So basically you were paying Jim to fuck Laura, and he was making sure you couldn’t get any from her.’
I was astonished. I had been paying Jim for years to be allowed to suck his cock, then had been paying Laura for a long time in hopes I would get her bra off but really only got badly cockteased, and all that money had gone to Jim too. I felt like such a fool.
‘Ok Skip, enough talk.’ Bill was ready for business. He stood up and slid off his still tented blue briefs, now showing a substantial wet spot. Eye level to me his stiff prick sprung free. It was well shaped and cut, but was rather small. It appeared to be about 5″ to 5.5” and average thickness. Call me a hypocrite or afflicted with some sort of self loathing, but small cocks do nothing for me and this was no exception. Seeing it, even in my very aroused state, I could feel my erection wilting.
But Bill really didn’t care, this wasn’t about me. ‘Start with the balls, get them good and wet, and I will tell you when you can start on the cock.’
Bill and I had been talking for almost 40 minutes, and he had left me in the bedroom waiting for about 20, so we didn’t get started for almost an hour. But once we did start, Bill was determined to get his $20 worth. The next two hours was a bit of a blur, but bottom line is Bill shot four loads in two hours. He made me take two in my mouth before he decided it was time to fuck. But after a long session slamming in to me, which honestly got boring with his small cock, he decided to make me do ass to mouth. I begged him not to make me do it, but he made it clear that if I ever wanted to see Jim’s cock again I was going to do it with enthusiasm. Eventually he returned to my ass to unload, then made me clean him again. His fourth and final load he stroked out on to my face, making me leave it there as I when he sent me out to dress and pay Jim.
Jim got more than his share of entertainment as well. He really enjoyed the remnants of the facial, but Bill also sent me out twice to get him cold drinks for him, forcing me to walk right past Jim as he sat at his computer surfing and emailing. I was too ashamed to even look at him, but heard him chuckling and commenting on how long we had been in there.
When I finally was allowed to dress and leave I was exhausted and filthy. My ass and balls ached, but for the first time in years I actually left without a throbbing erection. The length of the session and Bills tiny cock had me limp as I dressed to leave. Jim took my money, obviously pleased with what he had made me do, and suggested I email him later in the day to find out if I got a good report from Bill. Yet another hoop he could make me jump through, which is Jim’s number one joy with guys.
He said if the report was bad I wouldn’t get an email back, I knew right away that Bill would take his time replying so I could suffer a little. I was reaching for the door when Jim stopped me. ‘Aren’t you forgetting something?’
I was confused at first, the session had been so long and different from anything before, but fortunately I figured it out. ‘Thank you Mr. Smith for allowing me to visit, and thank you for letting me service Mr. Taylor.’ I don’t know if I was as enthusiastic as usual, but Jim allowed me to get by with my attempt.
I drove home with my head swimming with the new information about Jim’s ‘business’, all the women who pay for his cock. The small breasted (like C cup is small breasted!) friends of friends, the ex’s, rich women paying big money. Laura with her DDD’s having to pay, and making me give her the money for it.
And somehow, with Jim being this comfortable making people pay for it, being the only guy paying became even worse.
But mostly I thought about how I didn’t get any of his big cock, and that I needed to see him soon.
This will likely be the last installment of this story. The events I describe here may be the end of the 5 year arrangement between Jim and me, though on more than one occasion I have tried to quit seeing him and failed, so I guess we will see. We may yet see another chapter.
For those of you who have not read previous chapters, the very briefest of summaries is this…Jim is a very well endowed guy in his mid-30’s. He works a series of hourly jobs, isn’t in great shape, and likes to smoke weed rather than work. But, his cock is a full 8″, and is as thick as a can of Red Bull. Sexually he is a genetic freak of nature, he can easily cum 5-6 times in a marathon sex session, can last forever as he pounds away, and doesn’t even soften between orgasms. On top of that, he can do all of this a couple of times a day, and never get enough. Simply stated, no exaggeration, if a woman ends up in his bed she is ruined for other guys. He is sweet and caring with women. But with guys it is another story. With guys he is a hard core humiliation Dom. He is highly skilled at using his huge cock to reduce men to drooling cock slaves, then forcing them to do anything and everything he asks.
I am a very successful international executive. I fly all over the world and live what many would consider the good life. I live in a beautiful home, drive a gorgeous BMW, eat at all the best restaurants and have a wine collection that totals hundreds of bottles. Tall, thin, good looking and very fit…a former marathon runner. But…I am cursed with a very, very small cock…almost 4″, well 3 ¾” when fully hard. And I crave really big cocks, which is nearly impossible to get when you are cursed down there yourself. At this point I would suggest you read the previous chapters, but bottom line is I have been meeting Jim regularly for about 5 years, doing anything he tells me to do (including only calling him Mr. Smith) and paying him $50 for the privilege of servicing him.
It had been about three weeks since I had seen Jim last, he requires a minimum of a monthly visit or I have to pay his fee for that month anyway. The day before I had felt the familiar urgent need, and he permitted me to schedule a time. Our session had been fairly typical of sessions over the years. Jim greeted me with a warm handshake and I handed him his iced coffee and condoms in both our sizes. We chatted briefly just inside the front door as he watched me strip down and fold my clothes neatly on to a chair. My cock was about three quarters erect as I undressed; a requirement of Jim’s when I arrive as a show of respect. Jim never shows any sign of noticing my jutting cock, but I know he checks. As I followed him to his back bedroom/ computer room Jim gestured to the cleaning supplies that were stacked on the floor in his bathroom. ‘Come in and let me know when you are done’ was all he said, and since he often made me clean his bathroom when I arrived I couldn’t really pretend I didn’t get his meaning.
Jim’s bathroom is generally disgustingly dirty; I am convinced he allows it to get that way intentionally knowing I have to clean it. I am sure he doesn’t do any kind of cleaning at all between my monthly visits. So the work is hard and disgusting, and there is something deeply degrading about being naked and on your knees scrubbing floors and toilets and bathtubs. But I set to the task with an efficiency of having done it many times, the only sign that I minded was my cock shrinking to its totally flaccid state. After about 35 minutes of steady hard work I had it done to a true shine, my knees and back aching from the effort and a sheen of sweat had covered my upper body. I walked in to the back bedroom to find Jim texting and emailing, presumably with some of his collection of very busty regular FWB’s who line up to get in his bed.
‘The bathroom is ready for you to inspect Mr. Smith’ I mumbled with my eyes downcast. The shame of doing the cleaning is tolerable, but his insistence that I ask him to inspect my work has always been hard to swallow. Jim ignored me for a good three minutes as he continued to type and chuckle, finally signing off and looking up. I knew better than to repeat myself while standing and waiting, I knew he expected me to just wait.
Jim got up from his chair and brushed past me to the bathroom. I followed closely behind to hear his verdict. About half the times Jim will insist there is some small flaw in my cleaning and direct me to come get him when I have it done right. But today he took it a step further. Jim glanced around the spotless tile and porcelain, then bent over and lifted the seat of the toilet. He angled himself back to me, fumbled a bit at his belt, and then the unmistakable sound of urination in to the toilet began. After a long steady leak Jim finished, put everything away and turned to the sink to wash. Only now did he turn and speak to me. ‘Why don’t you rescrub the toilet and sink, then wash up and come in.’
I seethed at this intentional humiliation, he couldn’t even bother to flush, but said nothing and set to cleaning the splattered toilet and sink again.
When I was finally done to Mr. Smith’s satisfaction I was permitted to come in to the bedroom and begin servicing him.
The session itself was pretty standard. As always it began with foot and leg massage, all a build up to having to spend a long time stroking the area around his crotch without permission to touch the huge hose outlined by his shorts as my throbbing cock drooled in to its condom. Eventually I always earn Jim pulling it out, and after some more groveling I am allowed to suck and slurp alternating between his monster shaft and balls. Nearly every session is two loads, Jim taking my ass with the first load, then after a brief condom change I have to give him a very long jaw and back breaking blowjob to completion.
So we had finished, and Jim was lying back contented from my hard work and his repeated orgasms. As usual I was sent for a warm washcloth and thoroughly cleaned him, disposed of his condom, then went to his kitchen and brought him a cold beer. At this point Jim is always fully dressed again, enjoying his beer, and likes to sit and chat about local sports and recent huge breasted women he has bedded. I am always naked, rock hard and aching to cum, and know I cannot so much as touch my throbbing cock in Jim’s home. So while Jim likes to chat, I can barely form a coherent sentence as my aching dick is the center of my world.
But today took a completely unprecedented and shocking turn in one simple question from Jim.
‘So Skip, are you seeing anyone?’
Jim had never once asked me about women in my life, other than very high level generalities about my history with women. So while he had insisted I tell him about my history of bra sizes I have managed to get on the floor (nothing bigger than B cup) he never asked about specific women. So his question was a shock, and temporarily took my attention from my throbbing balls, but all I could manage was a stunned grunt. ‘Huh?’
‘Are you seeing anyone? Is that too tough a question in the state you’re in?’ he snickered with an eye drop to my relentlessly hard cock.
Jim couldn’t possibly have known, but I was in the midst of a wonderful nascent relationship. But Jim couldn’t possibly have known that.
‘Uh yeah, sort of. Yeah I guess’ was all I could mumble. It all felt like a personal invasion, like a line had clearly been crossed and I suddenly desperately wanted to hurriedly dress and leave.
But Jim was oblivious to my discomfort, and pressed on. ‘So tell me about her. What’s her name, how long have you been seeing her, does she have big tits?’
Danielle and I had been seeing each other for almost six months. We met through a local singles board, connecting through our shared passion for liberal world politics, and bonding through our similar high energy sense of humor and love of playful debate. She was twelve years my junior but was unabashed admitting she preferred older men. She was a young attorney and smart as a whip. I was glad I had met her online, sight unseen, because her first impression is always her striking beauty, and it was her intelligence, sense of humor and energy that had attracted me. Danielle is tall, about 5’8″ with a thin athletic figure. She is an avid runner, and very fit. Her dark eastern European features are smoky and mysterious, with big brown eyes that are always ready to laugh. She loves good wine, and to be spoiled with fine dining. I was very, very smitten.
But the question was hanging out there, and it was honestly terribly uncomfortable to talk about something that felt so private while naked with a now sagging erection. My urgent need to relieve my balls had evaporated. So I answered Jim, but honestly have no idea what I said. I babbled something about her being young and pretty and an attorney. About not seeing each other as often as we would like with busy professional lives in the past six months.
‘Sounds great Skip, but answer the question, does she have big tits?’ Jim has always been pretty one dimensional about women, and can be very, very selective, so his focus on bra size was not surprising.
I delayed and stammered, but eventually had no choice but to answer. ‘Well, uh, well, not real big, um not really. They’re about the right size I guess.’ By now I was completely limp with my shriveled cock barely able to hold on to its condom.
Jim laughed loudly. ‘What the hell is about the right size? What does that mean? How small are they, give me a cup size.’ Jim smelled blood, and was clearly enjoying himself.
I felt trapped and literally naked and saw no way to avoid the question. The truth was that Danielle had the figure that is stereotypical of women runners…long legged, lean and fit, but with very little in the bustline. And there was no dancing around it. ‘Uh, well I don’t know. About an A cup I guess.’ Normally an articulate and confident speaker, Jim had reduced me to incoherence.
But now Jim suddenly broke in to an evil grin. He clearly knew it was time to go for the jugular, and was cherishing the moment. ‘You’ve never seen them have you. Six months of dating and you have never gotten her bra off have you? ‘ Jim knew the answer, and was delighted.
Danielle and I had an intense connection from the day we first met. Our long dinners, bottles of wine and spirited debates over candlelight quickly led to touching and tenderness. But it never quite led to intimacy. Busy lives, early morning flights, buzzing blackberrys always seemed to interfere. But finally, just the weekend before our schedules suddenly seemed to have finally parted, and Danielle arrived at my condo to spend a Saturday night making dinner over a bottle of fabulous Pinot Noir. I was certain that the evening would finally end with her in my bed. Jazz played, wine and risotto satisfied. Kitchen clean up, and a second bottle of wine had us laughing, touching, and finally and leaning against the kitchen counter passionately kissing. Our midsections were pressed together, making no secret of my arousal. My hand slid up her side to toward her clothed breast, only to encounter a firmly placed elbow. Danielle’s hand slid up to my chin and gently pushed me back with her index finger.
‘I’m not ready’ was all she said. I looked puzzled, so she continued. ‘I don’t know why, but I’m not quite ready, I hope you can understand’.
What choice did I have…chivalry mandates graciousness and I complied. But I am guessing the blue balls were a major part of what had me emailing Jim with urgency two days later.
‘No’ I mumbled to Jim.
‘No what ‘ he demanded in obvious glee. ‘Have you seen her boobs or not?’
‘No, I haven’t seen her breasts’ I admitted in shame.
Jim knew there was more fun to be had. ‘And you haven’t fucked her?’
I just shook my head, I couldn’t answer.
‘Not even a hand job?’ Jim pushed on in apparent glee and I just shook my head again.
‘You are pathetic Skip, I’m telling you I could fuck this chick on a first date. You know it’s true too.’
Jim seemed quite pleased with himself and I didn’t debate his meaningless boast, so I thought I might finally be able to escape. But rather than getting permission to get dressed and go Jim let me know he was nowhere near done. ‘Skip, get me another beer, I want to hear more about this chick.’
I tried to protest. ‘Mr. Smith, can’t I just go.’ I was a little stunned I had actually said that, Jim had always demanded complete obedience, but he let me off the hook.
‘Just get me a beer and kneel on the floor, we have more talking to do.’ I scampered off to get his beer. My shrunken cock could no longer hold its condom, so I deposited it in the trash with its load of pre-cum. I brought Jim his beer, and kneeled on his hardwood floor.
Jim appeared to be in deep thought, not usually his natural state. ‘Skip, I want to meet this chick.’
I looked horrified, I sensed he was actually serious, and was speechless.
Jim pushed on. ‘Here is what I am thinking. I’m thinking the three of us are going out for drinks. You can choose the place, some place with some nice booths where we can all sit nice and cozy. Some place where she will be comfortable.’
I was in shock, he clearly wasn’t joking, though I hoped at any moment he would laugh it all off. He didn’t.
‘I want you to tell her everything before we meet. I want her to know you have been my cock bitch for the last five years. Tell her you pay me for it. Tell her EVERYTHING.’ Jim drew out the last sentence as his vision of the evening took hold.
‘Jim, you can’t make me do this. I can’t, there’s no way she will do it.’ I blurted out.
Jim’s face turned dark. ‘What did you call me?’ he snapped.
I realized my error, and correcting it reconfirmed my momentarily forgotten role. ‘I’m sorry, I’m sorry Mr. Smith. But I can’t tell her, please don’t make me do this.’
Jim got up and moved to his computer. He talked quietly as he tapped and clicked. ‘Skip, you are going to do this. You are going to figure out how to tell her everything and still get her to come for a nice evening with the two of us. And I know what you are thinking. You are thinking it’s probably worth me cutting you off so you don’t have to do this.’ Jim’s back was to me as he sat at his keyboard, and I was kneeling on my aching knees staring at the floor. And yes, that was exactly what I was thinking. But as usual Jim was several steps ahead of me. ‘You are going to do this because if you don’t the world will know what a faggot ass cocksucker you are.’ Jim rolled away from his keyboard, revealing his monitor and there on the screen was a huge, close up, crystal clear picture of my naked form. My tiny cock was rock hard, and my mouth was wrapped around the enormous head of Jim’s cock. My face was very clearly visible, front and center. Only Jim’s cock and balls were visible.. I was red from the exertion, and the size comparison of our packages was if anything exaggerated by the angle.
My jaw dropped, I couldn’t speak. But Jim continued.
‘There are a couple more where this came from, though this might be the best one. Laura took them with her camera phone one day, they came out pretty good.’ Jim laughed heartily, I couldn’t tell if he was laughing at my situation, or my reaction…I just didn’t know. Jim confessed he had never imagined using his stash of pictures for blackmail, but ‘life takes unexpected turns’ as he put it. And he was clearly enjoying it.
With nothing more to be said, we both knew I had to do what he asked, Jim’s sly smile returned. He reached down and slid down his gym shorts revealing a nearly full hard on. He had never been shy about saying how much he enjoyed power over other men, so his erection was not surprising. ‘Ok, get over here and take care of this.’ It was the first time I felt like I was being forced to submit to another man against my will.
I left Jim’s that afternoon in shock, but had already begun to piece together a plan that had a small sliver of a chance of working, of maybe somehow letting me keep my relationship with Danielle while doing as Jim demanded. It all came from a tiny window of insight to Danielle’s darker side from an evening about six weeks before.
I had asked Danielle to come to a political fundraiser with me…I kidded her that all the movers and shakers would be there and I needed serious liberal eye candy on my arm. She punched me in the arm, but clearly looked forward to a lavish night at a spare no expense event in at the estate of a local philanthropist. Not to mention a chance to meet all of the most important Democrats in the state. I picked her up that evening, and she slid in to my BMW looking sensational in a basic black cocktail dress and pair of heels that pushed her to about 5’11”. Eye candy accomplished, and she knew it. We pulled up to the front door of a lavish, but still tasteful 19th century home, and Danielle had heads swiveling as we made our way in. The home was gorgeous, the flowing wine was unaffordable, and the food was sensational. And the guest list was even more impressive. We mingled, we toured the grounds, I introduced her to people she had only read about. And of course I handed in a pledge card, so they got theirs…
I ran in to an old friend and his stunning wife Lori. Lori is a gorgeous brunette, model thin with huge breasts that are rumored to be completely real. He and I got talking in animated fashion about our golf games, some of it was actually true. The women were hitting it off almost instantly, and were sharing wine fueled giggles about other guests. At one point out of the corner of my eye I saw Lori looking around furtively, then leaning to Danielle’s ear and whispering. Danielle smiled, hesitated, and then nodded like she was thrilled to be a little naughty. The two girls scampered off together toward the open back patio doors with their glasses of wine. On the patio they moved to the stone railing where Lori greeted a friend. The friend laughed, and handed Lori a pack of Marlboro Lights and a lighter. Lori and Danielle each took one, then Lori extended the lighter and gave Danielle a light. Danielle was at an angle to me, but the plume she blew skyward confirmed she was sneaking a smoke with new found friend. Danielle had never said anything about smoking to me, but I was not concerned with a social cigarette, and In fact felt my cock twitched as I watched her inhale in her dazzling dress and heels. The whole scene was so sexy, and her practiced mannered made it clear it wasn’t her first social cigarette. Just as my buddy and I were winding down our golf talk the girls were making their way back to us. Danielle took my arm and let the group know she enjoyed her new friend. There was a very feint smell of smoke surrounding her, and again I felt a significant twitch in my briefs.
Later that evening Danielle and I snuck off to a local 18th century tavern, the casual pub was a fun destination in our dark cocktail party attire. We sat at the end of the bar in the quiet pub and traded laughs with the buxom blonde barkeep. Danielle was comfortably buzzed, and ordered a dirty martini. She laughed as she told the bartender she liked them dirty and liked them big. The bartender didn’t miss a beat. ‘We all do honey, well at least the big part.’
Danielle raised her wine glass. ‘Isn’t that the truth.’
I looked at Danielle in mock horror.
‘What’ she said in feigned indignance. ‘C’mon you know that. There are lots of ways to make a woman feel good, but there is no substitute for size. Bigger is absolutely better.’ The bartender delivered Danielle’s martini, then Danielle picked back up where she left off. ‘Everyone always says size doesn’t matter, size doesn’t matter. Then you get your hands on a big one for the first time and say…someone lied to me’
I pretended to be unaffected by Danielle’s sudden wonton praise of well hung men, but my confined cock was painfully hard. Mercifully the topic faded away, but the provocative topics had not ended. Danielle and I ended up talking about our common struggle to work during a mid-afternoon lull, and she described the strong urge to put aside whatever contract she was reading at about three and start surfing celebrity gossip sites. Innocently I asked what celebrities she most enjoyed following through the media’s eye and without a second’s hesitation she said ‘The woman I would leave any man for…Angelina Jolie.’
Danielle took a leisurely sip of her martini, as if she was oblivious to bombshell she had dropped.
So I bit. ‘So you are attracted to women?’
‘Sometimes.’ She said. ‘But I would say my first choice would be guys 90% of the time, but when I find that 10%…wow.’
I tried to keep my composure, but it was getting very difficult. ‘So you have actually been with women?’
Danielle still seemed completely unfazed. ‘Sure, but only a couple of times. I have no gaydar, so if I don’t just fall in to it, it isn’t going to happen.’
She took a long sip of her drink. ‘What about you?’
At first I had trouble processing that she had actually asked me the question, so I half sincerely sent it back. ‘What about me what?’
‘Are you in to guys at all, have you ever been with guys?’ she asked.
I still was in shock, but was even more stunned when I heard myself actually answering the question. ‘Uh, well maybe a little.’ Even I didn’t understand my answer, but I knew I had just basically said some form of yes.
But Danielle didn’t press it. ‘Huh’ was all she said.
The night had been crazy. The opulence of the party, Danielle’s stunning dress and heels, and the wild sensual confessions in the pub. I don’t really know what happened from there, somehow I took Danielle home and got home much too late for my early trip to the airport.
So I left Jim’s house already thinking back to the night and the conversations in the pub. Hoping that my half hearted confession, and her lack of reaction, meant she would think this was all no big deal. It seemed like a long shot, but possible. And, perversely, hoping that her wanton rantings about well endowed men would make her curious enough to agree to come out for drinks. But mostly I kept cursing that Jim had those pictures, and my having no choice but to practically serve Danielle up on a silver platter.
The following day I called Jim, hoping he would tell me he was just busting on me. But he was thinking no such thing. In fact he was pushing for a commitment to make it happen before the weekend, giving me only a day or two to sit down with Danielle. I pleaded with him to call it off, but in fact he made it clear what this was all about if I had any doubts.
‘Skip, we both know I am going to be fucking her before the night is over. I’m going to get in one night what you couldn’t get in six months. By the time you finish telling her about my cock she won’t be able to get on her knees fast enough. And you won’t have any chance of getting it once I am done with her.’
I tried to reason with him that she really wasn’t his type, I really don’t even know what I said, but he cut me off.
‘I know she’s not my type. I can stand those skinny flat chested types. I’m just doing to this to fuck you over.’
In about his only act of mercy he did agree that I didn’t have to tell her that I pay him for it, and while I did have to tell Danielle how well endowed Jim was, he agreed that I didn’t have to tell her how small I was. However he was adamant that I tell her that it was strictly one way, that he never reciprocated. ‘Make sure she knows you are the one that’s a fag’ as he put it. Oh, and he made sure I knew that even in front of her it was still Mr. Smith to me, Jim to her.
I texted Danielle and invited her to dinner. Things had been a little awkward since the night at my place, I felt like something changed, but she happily agreed to dinner. She called and asked if anything was wrong. Said she heard something odd in my voice. But at 7:00, right on time as usual, she arrived at my door looking great in a pair of jeans and a cotton sweater that was flattering but didn’t call attention to her small bust.
A light dinner, a little bit of wine, and I dove in and started explaining there was this guy.
‘So the two of you have had a regular thing…like for a couple of years?’ Danielle asked without seeming panicked about it.
‘Yeah pretty much.’ I shrugged, trying to pretend to be nonchalant. ‘It’s not anything like real, I mean it’s just sexual I guess.’
Danielle sipped her wine, and actually seemed intrigued. ‘So how does this work, do you two just get each other off, is this oral, anal, just hand jobs….how does it work?’
Her nonchalance had me really off balance, and her blunt questions were stunningly direct, but I knew this is where I had to follow Jim’s rules. ‘No, it’s pretty much one way, well it’s all one way.’
I thought I was clear, but not even close. ‘All one way what, like you both only do oral, I don’t get it?’
I gulped. ‘No, I mean I get him off, but he doesn’t reciprocate.’
She seemed confused. ‘So is this oral, anal, handjobs…’
‘Well not really hand jobs, well actually never a handjob.’ I could feel myself sweating.
‘So its oral and anal, you give he gets…how do you decide which one?’ she asked, still pretty unfazed by it all.
‘Well, it’s usually both; he likes to get off both ways.’ I was getting calmer as Danielle was just going with the flow on this.
‘So he gets off twice when you meet, wow, guys who can cum twice are gifted. And you what, just jerk off or something’ she asked..
I have no idea why, but before I could stop myself I actually clarified. ‘Well its always twice, but sometimes more…’ I knew I had to answer the other question. ‘No, I don’t jerk off, I just leave after he is done.’
Denielle looked confused. ‘So you don’t get off at all? What guy has sex and does cum? I don’t get it, do you just leave with a hardon?’
At this point I actually blushed. ‘He prefers I don’t jerk off at his place, that I wait until later.’
Denielle actually chuckled….but continued. ‘So I don’t get it, why would you keep hooking up with a guy who you get off two, three, four times and he never gets you off?’
Confession time. ‘Because he is really big, he ummm, he is really well hung and that’s how he prefers it.’
Danielle broke in to a big grin. ‘So you’re a size queen too huh?’ She thought for a moment. ‘So how big is big?’
‘About eight inches, about eight inches and really thick.’
Danielle let out a long low whistle, and was silent for a moment. ‘Yeah that qualifies as big. Bigger than anything I have ever seen. Big and can cum over and over…’ We just sat silently for a few minutes. ‘So you two are friends, or what ….’
‘Sort of, well I guess.’ I gulped but went for it. ‘He would like to meet you.’
I set up with Jim that we would meet two nights later at a local place, pretty casual place with some pool tables, but had the booths he had been so specific about. We agreed to meet at 8:00. I picked up Danielle at her place, and it was clear she had made an effort to look good. And she did….her jeans and a pair of sandals looked great, the whole look was casual but meant to impress. It was working. Surprisingly Danielle didn’t seem the least bit nervous, chattering away about a big project she was working on at work and asking about my trip planned for early the next week. It was a very short drive to the bar, and Danielle squeezed my arm on the way in.
Jim was already there, had claimed a booth, and was chatting with a chunky brunette with huge breasts. Jim was very casually dressed, an untucked polo shirt and jeans, he clearly didn’t feel he had to make an effort. Jim and the brunette obviously knew each other, I assumed she was one of Jim’s girls and couldn’t help but envy him getting play time with huge boobs like those. Jim glanced up, but finished his conversation with the young woman…her name was Marie, before he finally turned his attention to us as Marie left. Jim said very little, he just gave me a look that made it clear he expected me to make introductions. I quickly figured out why…having no choice I had to address him, but tried to do it casually so Danielle wouldn’t notice. ‘Mr. Smith, this is Danielle, Danielle this is Jim.’
Jim smiled and extended his hand to her. ‘You are even prettier than Skip described. So good to meet you.’ Jim then turned to me. ‘Skip, why don’t you get drinks for everyone, I already opened a tab for you.’ The inference was obvious, I’m sure Danielle caught it.
I turned to Danielle as she slid in to the booth. ‘Sauvignon Blanc for you?’ Danielle nodded. I then turned to Jim, but he didn’t say a word, and I noticed that though he said he opened a tab he didn’t have a drink. I later found out the tab he opened was to send drinks to his big titted friend and her similarly endowed companion that were sitting in another part of the bar. But Jim continued to just sit, forcing me to ask him. ‘What would you like to drink Mr. Smith?’ Danielle definitely noticed this time and gave me an odd look. Jim ordered a Sam Adams.
I made my way to the bar and waited a few minutes for a bartender to free up. I kept one eye on our booth, and Jim and Danielle were chatting and laughing quite comfortably already. By the time I brought the drinks back Danielle was telling funny stories from her sorority days, and had slid to the middle of the booth so she was sitting between Jim and me. The chatter and laughter kept up pretty easily, and Jim sent me back to the bar a couple more times over the next hour and a half. Danielle seemed to be clearly enjoying Jim’s company, though it seemed to me like she was pretty much carrying the conversation. She was always one to easily make connections with new people, but this seemed like record time even for her. Once or twice I found myself drawn in to the laughing and storytelling, but quickly caught myself and just focused on my Scotch. I didn’t want to appear sullen, but I didn’t want to make this any easier for him.
During each trip to the bar I tried to keep one eye on the two of them, but by the second round it was clear that Danielle was sending signals with some light accidental touching on the arm…no telling what signals she might be sending under the table. Danielle seemed to be enjoying the wine a bit more than I would have expected, and was very entertained by anything Jim contributed to the conversation. She had scooted over in the booth ever so slightly on several occasions to hear Jim better, and now was sitting quite close to him, and opposite me in the booth.
We had gone through three rounds of drinks and the conversation finally hit a bit of a lull. There was a brief awkward silence before Jim turned to me. ‘Skip, why don’t you go to the bar and settle the tab, then just wait there for a few minutes. I will let you know when you can come back.’
I looked at Danielle, but she didn’t respond. I found myself mumbling ‘Yes Mr. Smith’ and slid out of the booth. Danielle looked amused by my compliance to Jim’s direction. I got to the bar and signaled the bartender. She asked if wanted another round, but I told her just the check. When the bill came she told me about the round for the two girls, and combined with my Scotches the tab was a bit steep, but I paid it with a nice tip for her. Then, I just sat at the bar. I really didn’t know what to do and didn’t want to stare though I was waiting for some kind of signal. Jim and Danielle had turned in the booth to face each other a bit more and were in to a conversation. It didn’t take a genius to figure out the topic. Eventually they both nodded and smiled, then chatted a bit more and were laughing. Neither seemed concerned that I had been left hanging at the bar. I glanced at my watch, I couldn’t help thinking my watch was worth more than Jim’s car. It was about 10:15.
Finally Jim and Danielle slid out of the booth and made their way to my bar stool. Jim did all the talking with a very subtle look that made it clear he had won, and was enjoying doing this to me. ‘Danielle and I are going. You got the tab right?’ I could only nod, Danielle didn’t seem to notice the whole awkwardness of the situation and was quiet.. Jim knew I got the tab but was enjoying turning the knife in front of her.
He pushed on, if I didn’t think this could get any worse, it did. ‘I guess you drove Danielle, so you will need to come pick her up. Why don’t you come to my place about 1:00 and just wait in the car, one of us will text you when she is ready to leave. That’s ok with you, right?’ I couldn’t believe Jim was doing this to me, that he couldn’t even take her home himself and had actually thought out humiliating me by having me pick her up when he was done with her.
‘Yes Mr. Smith.’ Was all there was left to say.
Jim just stood and smiled silently for a long moment, letting me twist and suffer. ‘Ok Skip, well, see you in a few hours then…’ Jim said and he and Danielle turned and left. Watching them leave together was made me ache, I knew from experience what she was in for.
I stayed at the bar and had one more Scotch, I didn’t know what else to do. Finally I drove home, and put on the television, but I couldn’t tell you what I watched. The time crawled by, obviously all I could think about was Danielle naked at Jim’s place, just going crazy over his big cock, and him giving it to her over and over. After knowing Jim as long as I have I knew his motives for the night were only evil. Sure he wanted to get Danielle and humiliate me. But I somehow also knew he wanted to give her a night that left her incapable of being satisfied by other men…the size, the stamina, the ability to cum over and over. I knew this was all just an evil game to him.
I left my place about 12:30, a little angry that I had to pick her Danielle up, but in a way deeply curious about what kind of state she would be in coming out the door. The drive to Jim’s was only about 10 minutes, so I pulled in to his driveway a full 20 minutes early. I shut off the lights, I thought about leaving the radio on but somehow silence seemed more appropriate. The driveway was dark, the front porch light was off. There was some light coming from the front windows, but no real signs of life inside though I knew from experience the bedrooms were at the back of the house. I set my blackberry on the console and just waited.
Time passed as I stared at the house, looking for any sign they were finishing up their evening. I dared to think that maybe, just maybe, they had decided not to do anything and watched a movie or something. Seemed unlikely, but one can hope. One o’clock came and passed, and so did 1:15. Still no signs. I considered calling or texting, but really couldn’t decide which one to call or text and honestly didn’t dare. When 1:30 passed I couldn’t decide if I was angry or nervous or what I felt.
Finally after more than an hour, 1:48, my blackberry lit up and buzzed. I clicked the text folder and saw a text from Jim. I opened it, it was short, simple, and eliminated all doubts. ‘She is coming out, WELL FUCKED.’ I stared at the message, my feeling of total defeat now fully hit home. Because of that one picture on Jim’s hard drive he was able to orchestrate all of this.
The porch light came on and brought me back. I watched as the door opened and then the screen. Danielle was letting herself out. Somehow Jim not even showing her to the door confirmed my darkest thoughts…mission accomplished, he is done with her. Danielle stepped out on to the porch, and stopped. The porch was about 100 feet from the driveway and my car, but I could see her very clearly in the porch light. She stood on the porch and set her bag on the handrail. She extracted a pack of cigarettes from her bag, took out one and flicked her lighter. Even from the distance I could see her cheeks hollow deeply, then she tilted her head back and sent a large plume skyward. I am sure she wasn’t the first woman to come out that front door and badly need a smoke. She just stood for a moment staring off, oblivious to my sitting in the car, then raised her cigarette and inhaled once again to her toes. Finally she turned and took a few steps to the stairs. Danielle stopped at the top of the stairs and reached for the railing. With a firm grip she carefully began to step down, wincing as she gingerly eased herself down one step. She repeated the ritual again, wincing quite clearly, then stopped for another drag on her cigarette. Finally she felt up to tackling the two remaining stairs though the process was slow and clearly uncomfortable. Finally on the ground, she kind of shuffled slowly toward the car. At the passenger door she took one last deep inhale, crushed out her cigarette, and opened the car door. Unlike the beginning of the evening when she slid right in to the leather seats, this time Danielle used a slow process of handholds as she slowly lowered herself in to the car. When she was finally fully lowered in to her seat and the door was closed she out a long breath of relief. The lingering smell of smoke filled the car as I started the engine and backed out in silence. It was 2:03 on the car clock.
Once on the road, it didn’t take long for Danielle to speak, and her openness stunned me. In hindsight I think her total lack of any inhibition might be because she knew I had been in the same bedroom, on my knees in front of the same huge cock, but still…
‘Jim is a fucking machine’ she started. ‘He can just go and go and go, the guy can last forever, and can cum over and over with no break. He must have cum 6 times!’ She paused in silence for a moment. Then she started in a low voice just above a whisper. ‘He is superhuman, no guy can do that, 6 times with no down time.’ Again there was silence, I was just too stunned, and some combination of humiliated and embarrassed, to speak.
Danielle started up again. ‘My god, his cock is so fucking huge. I have seen ones almost as long, but it is so thick. The head on it is the size of small apple. I could just barely get it in my mouth.’ I couldn’t help it, at the mention of trying to get it in her mouth I groaned. Not that I hadn’t assumed she would suck it, but to hear her say it with such admiration and primitive lust was more than I could handle. I groaned, but my cock was stiffening uncomfortably and I didn’t dare try to adjust it.
Danielle heard the groan and turned slightly in her seat. Until now it was as if she was just talking to no one and anyone, but now she turned as if to speak to me for the first time. ‘I don’t need to tell you all of this.’ I thought for a brief moment she had felt a sudden need to show some sensitivity for my situation. But no. ‘You already know all of this better than I do.’
The drive to Danielle’s from Jim’s is about 25 minutes, it seemed liked days even at that hour on empty streets. She sat silently for a moment or two, I am sure processing all that had happened in the last couple of hours. Then turned to me and quietly delivered Jim’s final blow. ‘I think I understand your situation with Jim now, I really didn’t before. Jim told me you have a really small one. Now I get the whole one way, Mr. Smith thing.’
My defeat was total.
I dropped Danielle at her place…there was a quick goodnight kiss to her turned cheek and I watched her struggle to climb out of the car and shuffled to her door. I couldn’t bring myself to help her. As she moved slowly and gingerly to the door I glanced at my blackberry and saw I had another text from Jim. I opened it. ’34AA. They don’t do anything for me but you would have liked them.’
That was pretty much it for Danielle and me. I made a half hearted attempt to get together about two weeks later, but we both knew it was too awkward to salvage it. I also knew that my attempts to bed her that had been futile before, now combined with full disclosure about my small cock had no chance. After about three weeks we just kind of stopped texting or calling, it was a relief to stop the awkwardness.
I continued to see Jim, I hated myself for asking to see him, but I just couldn’t help it. The tone of our meetings changed, he was even more superior to me than ever as he had so thoroughly demonstrated that he is much more of a man than me. About three months after ‘The Night’ I went over to see Jim in the late afternoon. Usual session…hand over the coffee and condoms, strip and scrub the bathroom, anal and oral. I did notice once or twice that Jim was checking his watch, but didn’t think too much of it. He didn’t seem interested in our normal post session chatter, and so hen he dismissed me I dressed carefully around my usual throbbing hard cock, paid him, and let myself out. I closed the door behind me, and as I started down the stairs a familiar car pulled in the driveway. It was Danielle. She was out of her car before she noticed me, and we both just stopped in a moment of incredible awkwardness standing in Jim’s front yard. She looked incredible. In her hand was a large cup of light iced coffee, and a small bag from a local store that I am certain held a box of Trojan Magnums.
There was really no denying what either of was there for. I didn’t know that she had, or was, seeing Jim again, but I wasn’t surprised. How could I be surprised. After a moment of awkwardness, Danielle broke the ice. ‘So’ she paused and her eyes dropped and locked on the impossible to miss tent in my slacks, ‘How was it? It looks like you enjoyed yourself.’
I couldn’t respond to that, and couldn’t figure out a way to hide my hard on, so I tried the only tact left to me, I tried to change the subject. ‘How have you been?’
Danielle just decided it was time to deal with it and blew past my question. ‘Look Skip, I’m really sorry, but you can’t blame me can you. Guys like Jim just don’t exist, it’s never been anywhere near that good with anyone else, not even close…’ She glanced at her watch. ‘Look, I gotta go, we can talk sometime, but Jim doesn’t like it if I am late. I’m sorry.’ She hurried past me up the stairs to the door where Jim was waiting to let her in. She went past him in the door…he stood in the doorway and gave me a wave, another gotcha kind of wave. I could see Danielle behind him inside the house hurriedly unbuttoning her blouse, presumably to be folded and put on the chair that had held my clothes only moments before.