Memorable for the Wrong Reasons

by Small Penis


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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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By ChristopherDB

A tale of voyeurism, masturbation, fetishes, female domination, orgasm denial, and small penis humiliation.

Something woke me in the night. A noise perhaps. I lay still, looking up at the bottom of the empty bunk above me, and then I heard something. A gasping sound, coming from the bedroom next door.

It was a rental chalet in the Smoky Mountains. My tiny room with its bunk beds shared a bathroom with the bedroom where Cheryl and Tim were staying. Curious, I quietly got out of my bunk and took a few steps to the bathroom door, which was slightly open.

I was able to push it open without a sound, and see that the door to their room was also ajar. The bathroom had no window and was perfectly dark, so I slipped inside and took a cautious gaze into the adjoining bedroom.

We were high on the side of a mountain with no need to close the blinds, so the bright full moon bathed their room in a soft glow. Both of them were naked. Tim was laying on the king sized bed, a four poster made of heavy timbers, while Cheryl sat on top of him, gently rocking back and forth on his cock.

One of her hands was planted on his broad chest while she traced her fingertips of the other lightly across his lips. He gently kissed and nibbled her fingers, letting out another stifled gasp as Cheryl briefly picked up the pace, but then settled back into her slow teasing rocking motion.

I was not afraid of being seen as they were too involved with each other, and the cool tile bathroom floor was solid under foot with no risk of making a tattletale squeak. My penis was erect within seconds, and I began to stroke it slowly and teasingly, as if Cheryl were riding me instead of Tim.

She was my ex-girlfriend. While she had gotten on top sometimes when we had sex, she never seemed to enjoy it. Made it out to be too much work. Usually after a few minutes she would claim she was tired, lie down, and have me finish the job. Tonight though, she seemed enthusiastic in the way she gently rode Tim’s penis, periodically bouncing a few long strokes just to frustrate him.

I thought I heard him call her a teasing minx and he firmly rolled her off of him, and then got up on his knees to enter her. The size of his cock was amazing. Tim and I had been good friends for years and there had been times, such as a gym locker room, where I had gotten a quick look at his penis. I think all guys are curious to how they measure up against their peers, and I knew Tim had me beat, but tonight, for the first time I saw his cock fully erect. It had to be at least ten inches long, glistening with Cheryl’s sweet pussy juices in moonlight.

She lay back on the bed, her long blonde hair spilling over the pillows. The nipples on her small firm breasts were swollen from arousal, and she spread her legs widely. He gently slid all the way in.

He fucked her with long purposeful strokes, and I could hear them both breathing heavily. I sensed that he would have fucked her harder, gotten the bed springs creaking and her moaning loudly, had they not thought I was sleeping in the next room.

I was now stroking my cock, an erection might have been half the length of his, and trying to match his rhythm. I could feel myself on the verge of cumming but I wanted to hold back. Tim might have me beat in penis size but I wanted to at least match him in staying power.

It was agonizing, and my knees started trembling as I jerked off in the dark bathroom, watching them through the partially open doorway. Tim, now fucking Cheryl as hard as he dared, the bed springs gave an occasional squeak. Then he let out several muted grunts and began to slow his pace.

He had cum, and I let myself have a long awaited release, suddenly realizing I was in trouble. I quickly swooped my free hand in and cupped it over the head of my penis to catch the next burst of cum, but the initial blast had flown who knows where in the dark bathroom.

In a panicked glance I saw Cheryl getting out of bed. When we were together she had always run to the bathroom after sex and it was likely a habit she couldn’t break. I slipped back into my room and pulled my bathroom door closed as quietly as I could, cum slick on both of my hands.

As I heard her soft footsteps approaching the bathroom I had some hope. If she didn’t turn on the light, she might not notice anything was out of place. I could wait until they fell asleep, which wouldn’t be long after a hot fuck like that, and slip into the bathroom to clean up my mess.

“Ewww!” I heard her squeal echo in the tiled bathroom. I saw the light come on through the gap under the door. “Chris! You fucking pervert!” she shouted at the closed door, and I head the privacy lock click on the other side.

Then I heard Tim enter the bathroom and ask her what was wrong. It seems she had stepped in my cum. I was busted.

“Dude! What the fuck?” I heard him yell. Then I heard him stomp back into their bedroom. My first thought was that he was going to kick my ass, and I suppose I couldn’t blame him.

I quickly picked the T-shirt I had worn yesterday up off the floor and wiped my hands and penis with it. Then I pulled on a pair of shorts and gym shoes. Tim might come in through the adjoining bathroom, or the main bedroom door that led out to a loft space that overlooked the living room. If he was going to bust in and try to kick my ass, I was at least going be clothed and ready to fight.

We had fought a few times in the past as friends sometimes do. Usually just wrestling but a few punches had been thrown. Those had been brief skirmishes, and I’d say they’d always ended in a draw. However, there was no telling if he’d been holding back those times on account of our friendship.

He was a bit taller and heavier than I. Over the last few years since we had graduated from college he had been hitting the gym on a regular basis and was certainly in better form than I. My adrenaline was flowing and though I was not looking forward to a fight, if it came down to that I knew I couldn’t hold back.

However, after Tim and Cheryl quietly argued for a while in the adjoining bedroom, I heard them both use the toilet, and then the bathroom light went off. All was quiet and it seemed they had gone to bed.

Just to play it safe, I locked the bedroom door and lay down on top of the covers without getting undressed. I couldn’t fall asleep for several hours, and even then it was a restless sleep with a lot of tossing and turning.

I woke to hear the sound of someone showering in the adjoining bathroom. Then there was some conversation between the couple that I couldn’t make out. Soon afterwards I heard them go down the stairs and out the front door. I heard Tim’s SUV start, and it sounded as if they drove off.

Moments later I stepped out of my bedroom onto the narrow loft. Standing at the railing and looking out over the living room below, the large comfortable sofas in front of the massive stone fireplace and big screen TV, I could see the parking area outside through a window. My car was there of course but Tim’s SUV was gone.

I glanced in through the open door of their bedroom at the top of the stairs. The bed unmade, some of Tim’s clothes on the floor. It looked like any other morning in there. Walking down the large open stairway to the living room, I went to the kitchen and started looking around for a pad of paper and pen.

My plan was to write a brief note of apology, then pack up my stuff and drive home. I had heard Cheryl saying all week that she wanted to have a pancake breakfast at some place that she used to go to when she was a kid. That was probably where they were headed now and it would be perhaps two hours before they returned.

There was another bedroom off the living room and I peeked in the doorway. The place was trashed. Man, this had been one messed up vacation. Renee and John had stayed in that room.

Renee was one of Cheryl’s friends. She and her boyfriend John, had originally come on this trip, but a few nights ago they got into a fight. Not just arguing, but it was physical. We had all gone to bed when we heard the commotion downstairs.

Scotty, a friend of mine since high school, had been sharing the small room upstairs with me. He and I were the first to burst into the downstairs bedroom. John had Renee pinned against a wall, but it looked like she had busted him in the mouth at least once. Tim arrived in the doorway less than a minute later.

I don’t even know why those two had been fighting, but the three of us said we weren’t going to put up with any of that bullshit, and they were going to have to pack up and leave the next morning, which they did. No one had been in their room since then.

The mattress was askew on the bed, a chair was knocked over, and there were empty beer bottles everywhere, some of them even broken.

Glancing at the kitchen, I saw it didn’t look much better. Dishes, pots and pans, had been provided with the chalet and we had cooked a few meals in during the week, but no one had bothered to load the dishwasher so they were just heaped in the sink and on the counter.

I realized that if I took off now, Cheryl and Tim would be stuck cleaning the place all day. If they didn’t, Tim would get a steep bill for the cleaning, since he was the one that had arranged the rental.

So I rinsed off as many plates, glasses, and utensils that I could fit in the dishwasher, and started the machine. Then I made a pass through the living room and kitchen area, picking up all the empty beer bottles, cans, and other garbage I could find, and put them in the trash can. It then occurred to me there was another mess that I should clean up, upstairs.

The door to the bathroom from my room was still locked from the other side. I felt like an intruder, walking through Cheryl and Tim’s room to get in the bathroom. There was a faint outline where something had splattered on the floor tiles, been stepped in, and been left to dry. It was easy enough to clean up.

I checked the backside of the door and found what might have been where a small drop of cum had landed and run down, not quite making it to the floor. Again, that was easy to clean up.

My hand on the door to my room, I decided it might be best not to go out that way leaving it unlocked. Walking back through Cheryl and Tim’s bedroom, I saw a huge pile of boxes and bags in one corner. She had certainly been doing a lot of shopping in town. Most likely Tim was picking up the tab, because that’s just the way she is. A large box caught my eye.

I could tell from the label it was a pair of cowgirl boots. Now I was in enough trouble already, but I have a fetish for women’s boots, so I had to check them out. There was time, right?

It was a pair from the Miranda Lambert collection. Heels maybe three inches high and lots of elaborate stitching on the shaft, but most amazing and might I say almost mesmerizing, was that the leather had a bright silver metallic finish. Perfect for a country music star to wear on stage, but I had no idea where Cheryl planned to wear these. She probably just thought they were cute and had Tim buy them for her. I realized then that my penis was starting to get hard and I had to adjust my shorts.

This was one sexy pair of boots, and I took one out of the box. If Cheryl had owned a pair like this when we’d been together I would have asked her to wear them when we had sex. She was the only girl I had confessed all my fetishes and fantasies to, and she had been kind enough to indulge me in some of them, though it was clear that such things did nothing to heighten the excitement for her.

The aroma of the new silver leather was intoxicating, and I ran my tongue slowly from the pointed toe up to the top of the shaft, trying to savor all the ridges of stitching as I went. Then I pulled down my shorts, releasing my almost fully erect penis.

I slipped the open shaft of the boot over my cock and clamped it shut, like a tight silver leather vagina. I tried to get just the right tension, so my cock could slide inside the boot shaft without chafing, but the new leather was too firm, and I wasn’t completely hard.

Guilt was probably to blame. I’d been caught watching Cheryl and Tim fucking, and now here I was attempting to jerk off in one of her boots. They could be back any moment, but I thought the boots were so hot, and knew I would never get another chance to masturbate with them.

Quickly thinking of the best solution to my problem, I soon found myself on my knees on the loft. Through the railing I could see the parking area outside the window below. One boot was upright on the floor in front of me and I bent over to place my nose just inside the shaft. Inhaling the powerful scent of the new leather, I frantically stroked my cock, which I had lightly coated with lotion. The other boot lay over on its side on the floor beneath me, ready to be splattered with cum.

I had a towel nearby for a fast cleanup. All of the tissue packaging for the boots was laid out by the box in the adjacent bedroom, just in case I saw Cheryl and Tim pull up and the boots had to be put away quickly.

Despite having a great plan and being highly aroused, I couldn’t stay completely hard. I would get nice and firm, jerk myself and smell the boot, only to panic if I heard a car on the road outside and then my erection was gone. I was so frustrated. I had to cum on these boots or I would never get another chance.

After what seemed like a long time I finally got hard enough and felt that familiar tightening in my scrotum, and had an orgasm. Looking down there was only a small amount of cum on the side of the boot shaft, while the rest, a relatively small load, clung to my fingers.

I didn’t even allow myself to savor the moment but quickly set about cleaning the one boot, and then packing them both away as I had remembered finding them. Overall, that once in a lifetime experience of masturbating with those hot silver boots had been unsatisfying.

Cheryl and Tim didn’t pull into the parking area until some hours later. The dishwasher was cycling through its final load. Renee and John’s bedroom had been put back in order, and the floor swept. I was mopping the kitchen floor when they walked in the door.

Tim held the door open for Cheryl, who was carrying several large shopping bags. She barely glanced at me and headed up the stairs to their room.

“Listen man,” I told him. “I’m sorry about last night. My bag is already packed. If you two want, I’ll drive home right now.”

At first he didn’t say anything, and just stood on the other side of the kitchen island, arms folded across his chest. Then I saw him glancing around at the clean kitchen, and he stole a glance into the adjacent bedroom.

“I’m surprised you didn’t leave already,” he said, and looked over his shoulder at the living room, which looked as good as it did five days ago when we got here. “I appreciate you cleaning the place up. I wasn’t looking forward to doing all that.”

“I still need to hit the downstairs,” I said, referring to the finished walk-out basement.

“I’d just assume put this behind us,” he said. “But I’ve got to talk to Cheryl and see what she wants to do.”

The basement was smaller than the other floors. There was one room with a pool table, and a small bathroom that also had a stacked washer and dryer in it. We had all stayed up late the first night, drinking beer and playing pool.

It was just one of those six foot tables, and John had bitched endlessly about how lousy it was and how shitty the cue sticks were, and how much better his game would be on a good table. I think he just sucked at pool, because Scotty, one of the best players I know, got better as the night went on and he learned the table’s quirks.

I certainly didn’t miss John, though Renee had been a tasty treat to look at. Long dark hair and full breasts that she proudly displayed in low cut sundresses.

Yesterday morning Scotty had gotten a call from back home. There was some family emergency and he had to leave. We had ridden together and though I offered to leave early and take him home, he had me take him to a rental car agency. Scotty was shaken about something but didn’t want to talk about it. Trying to maintain his composure, he told me to check out the campgrounds as we had planned to do on the last day. I hoped things were going okay for him now.

Cleaning the downstairs was easy and really just a matter of tossing all the beer bottles and cans in the trash. There was a well-worn brush for the pool table, and I took the time to make the felt look nice.

A sliding glass door opened to a small patio area with a fire pit and hot tub off to one side, and I stood out there when I was finished. Looking down at some charred stubs in the fire pit, I remembered we had all talked about getting a fire going out here but it never happened. Perhaps we were too lazy and the gas logs in the living room fireplace were too convenient.

The view was pretty good. Obviously the mountains were great. I was undecided about the town of Gatlinburg, visible below in the distance. At one time it was just a sleepy town with a few motels for tourists, outside the Great Smoky Mountain National Park. Now it was filled with restaurants, tacky souvenir shops, and any other tourist trap you could think off. The nearby town of Pigeon Forge was perhaps even worse, though there were plenty of outlet malls where Cheryl could blow Tim’s money.

Scotty and I had been interested in the National Park. We had spent the days hiking the trails, including a section of the Appalachian Trail that passed through the park. Back when we had been in Scouts we had always talked about hiking that from start to finish. We had also been planning to check some of the primitive campgrounds in the park and see which one we liked best and would stay at on a return trip. It was a shame I might get kicked out of the chalet before that would happen, but then again that was my own fault.

Suddenly my mood brightened. I realized that if I got kicked out, I didn’t have to drive straight home. I could make a drive through the campgrounds first before leaving the area. Complete the mission. Yeah, that would be all right. I heard the sliding glass door roll open behind me and I turned around to face Tim.

“Chris, you can stay the last night, so long as you sleep in the room that Renee and John used. You need to take off and find something to do this afternoon though,” he told me. “Cheryl is still really pissed and this is the best deal I could work out.”

I told him that was okay, since I had planned to check the campgrounds in the National Park. He simply nodded. Before he went back inside, he told me that he was taking Cheryl to some nice restaurant in town tonight. Some place she had seen and was saving for a romantic dinner on the last night.

“If you come back here around six or so, we’ll probably be gone. We might stay out for a while too. She wants to ride that big Ferris wheel over in Pigeon Forge.” I just nodded as I knew the wheel he was talking about. It was impossible to miss as you drove through town on the main strip.

“The place is looking pretty clean,” he continued. “When you get up in the morning, just take off. You can grab a Mc breakfast of some kind on your way out of town and we’ll take care of any dishes we dirty before we leave.”

A short time later I was riding the brakes as my car wound down Ski Mountain Road into Gatlinburg, and then made a right turn towards the entrance to the National Park. It was a large park and I knew that visiting the major campgrounds would take all afternoon. It was when I got near Cades Cove that something clicked in my mind, and it had nothing to do with hiking and camping.

Cheryl and I had been together for a little over two years, and I’d like to think that things were okay most of the time, but I work in sales and my pay is based on commissions. Money was good most times, but the dollar amount on my paychecks fluctuated. I could deal with that, but it always bothered her.

I also covered a large territory and was out of town overnight quite a bit. After we broke up, or should I say she dumped me, she started dating my buddy Tim almost right away. He worked in engineering so he made good money, possibly better than me, and it was a steady paycheck.

Knowing Cheryl’s shopping habits, always wanting to go to nice restaurants and so on, I could see that she was nothing but a gold digging bitch, and left me for someone with a bigger wallet. While that made sense, they had gotten together so quickly, and I had been out of town a lot. Maybe she’d been having an affair. I wouldn’t think that Tim would do that to a friend, but she was pretty hot and I’d never known him to turn down a piece of ass.

I had to pull off to the side of the road because I was so upset. There was a sign for a trail that simply read, Quiet Walkway. I got out of my car and started to walk the path back into the woods to clear my head.

All I could think about was that a friend of mine might have been fucking my girlfriend when I’d been out of town. Fucking her with a cock that was about twice as long as mine. Damn! Even if penis size wasn’t really important to her, after experiencing something that huge she probably barely felt me inside her.

The trail was just a loop less than a mile long, and by the time I was back at my car I realized there was no proof Cheryl had an affair with Tim when we were together. I was better off not having that high maintenance bitch in my life. Furthermore, I was glad I had cum on her new cowgirl boots. Sure, I had cleaned up the mess so she would never know, but there was satisfaction knowing how pissed she’d be if she found out.

After my car had struggled back up Ski Mountain Road to the chalet, I saw the parking area was empty. They had gone to dinner, just as Tim said they would. I was hungry as well.

There was plenty of food in the fridge, some of which had been abandoned by Scotty, Renee, and John, when they departed early. I put a potato in the microwave, corn on the cob in a pot on the stove, and a steak on the gas grill that was on the deck outside the living room. I’d also picked up a twelve pack of beer on my way back and had put a few of those away by the time I was done eating.

Thinking it was best to move my things into the room downstairs before Cheryl and Tim got back, I went upstairs. My duffel bag, which I had packed earlier this morning, was sitting on the floor outside the door to what had been my room. That door was closed, and when I checked I found they had clicked the privacy lock, and exited through the connecting bathroom.

My electric razor and toothbrush, which I had left in the bathroom, were sitting on top of the duffel bag. The message was clear, I was out. I was about to head back down the stairs, but I had to take one last look in my former bedroom, simply because I was thorough and always made one final sweep before leaving a hotel, or in this case a chalet.

The small room with the bunk beds felt like a lonely place. Probably used by kids most of the time. No one that slept in here got laid. Sex was for the adults in the next room.

I hadn’t forgotten anything in that room but in the bathroom I noticed that a bottle of my shampoo was still on the edge of the tub. Best to abandon that. If I packed it up and Cheryl and Tim somehow missed it tomorrow morning, they would know I had passed through their room and likely get mad.

On my way out of the adjoining bedroom, I noticed that they also had their bags packed. The stack of Cheryl’s shopping conquests had been somewhat reorganized, and there was even a pile of pamphlets for local attractions to one side, which who knows, she might put in a scrapbook.

The thought came to my mind that it would be nice to smell some of her dirty panties. Earlier in the week her dirty clothes had been scattered all over the floor on her side of the bed. Everything was packed now though, and I wasn’t about to go pawing through her suitcase.

There was however a pair of her shoes, just under the bed on her side. A pair of black leather flats. I’m more a fan of high heels, but those flats were cut low on the sides and showed off her sexy feet pretty well, including a hint of toe cleavage. About as sexy as a pair of flats can get. Cheryl had worn those just about every day of the week. I knew they would smell strongly of her sweaty bare feet, and I was right.

Kneeling beside the big four poster bed, I clutched one of Cheryl’s flats in my hands. The black leather was soft and had many scuff marks. Holding it up to my nose and breathing in deeply, the smell of old leather soaked with the sweat from her sexy foot was almost overpowering.

I gave the insole a long, slow lick, and tasted the salt from Cheryl’s dried sweat. I licked the inside of her shoe repeatedly, only pausing occasionally to savor the aroma some more, until the flavor of her sweat was gone.

Picking the other shoe off the floor, I intended to give it the same treatment, but first I unzipped my jeans and released my cock, which was rock solid erect. Deeply inhaling and tasting the second shoe, I slipped the first one over the tip of my penis, jamming the tip into the toe box and rubbing it in the confines of the soft leather.

Sweating and shuddering with arousal, before long I erupted. I groaned loudly as I felt myself spewing one hot burst of cum after another into her shoe. Breathing heavily, I set one shoe down so I could steady myself against the edge of the bed.

Slowly I withdrew my now softening penis from Cheryl’s flat. The tip was glistening with cum, and a long thin drip clung to the insole as I pulled out. I had masturbated with women’s shoes before, but this time had been the most intense experience ever.

The thought crossed my mind to leave my cum in the toe of her shoe, and take off before she got out of bed in the morning. Who knows what shoes Cheryl was wearing tonight, but it was unlikely that she would change into these when she got back from her dinner with Tim.

I could imagine her reaction, slipping her bare foot into her shoe, her toes oozing into a puddle of cold and drying cum. In a sense I would get the last laugh, but I wouldn’t be there to enjoy the moment so I cleaned up my mess instead. There was plenty of time and after giving her flats one last inspection and setting them exactly where I remembered them, I went down to the kitchen to grab a fresh beer from the fridge.

Later I was soaking in the hot tub on the patio outside the lower level. I hadn’t packed a swimsuit so I’d just got in naked. Darkness was falling and the view of the forest under the stars was amazing, despite the lights of the town below.

Although I wasn’t into all the tourist crap down in Gatlinburg and Pigeon Forge, I could see it being a nice place to bring a girlfriend. We wouldn’t come with a big group of people though. Just the two of us in one of the smaller rental chalets. Some chick that liked to hike in the National Park by day, then go into town for a romantic dinner at night.

There was a chaise lounge near the hot tub. The back rest was reclined nearly flat. On a romantic vacation I could imagine just spending a day at the chalet, with my lady sunbathing on a lounge like that one.

I envisioned a young woman with large breasts and curvy hips. Long flowing brunette hair. Wearing a string bikini made with a gold lame’ fabric that gleamed in the sun. She would also be wearing some strappy wooden sandals with high heels, just because she knew they turned me on. I would rub the suntan lotion on her body, slowly, and seductively.

With the surrounding trees and our chalet being on the steep mountainside, there would be total privacy. I would get on my knees beside her, clench the bikini string above one of her hips between my teeth, and slowly pull to release the knot.

Then I would peel back the shiny gold triangle of her bikini bottoms to reveal her dark patch of neatly trimmed pubic hair. I may have even trimmed that for her earlier on our vacation. She would willingly spread her legs, hooking one spike heeled foot around my shoulders.

When I went down on her, she would already be moist and fragrant with arousal, and I would gently lick her until she came, her sweaty oiled body shuddering with pleasure in the sunlight.

As I fantasized, I adjusted my position so that one of the hot tub’s jets swirled the warm water around my crotch, as I lightly stroked my erection with my fingertips.

I envisioned another scene with the same girl, on the same private patio, on a warm rainy afternoon. I would be lying naked on the chaise lounge, the foam padding wet and cool on my skin.

My woman would be wearing a shiny black vinyl rain jacket, and nothing else but a pair of glossy black rain boots. The front of her jacket would be unsnapped to expose her wonderful breasts. She would be straddling me, aggressively riding my hard cock.

The rain would be pelting on our bodies and making a popping sound on her vinyl jacket. My hands would encircle her waist, wet with rain, and reach down to squeeze her sexy ass as she brought me nearer to orgasm.

I suddenly stood up and moved to the side of the hot tub. A burst of cum arced into the darkened shrubbery beside the patio, followed by a second shot. I leaned over the side of the hot tub and slowly milked the rest of my cum out of my softening erection, breathing heavily and completely satisfied.

It was some hours later when Cheryl and Tim got back to the chalet. I had been watching the satellite TV system and had dozed off. She was wearing a nice blue mini dress that showed off her body. It would have looked killer with a pair of stiletto heels, but she wore these unflattering sandals with low blocky heels. It was no surprise that she was carrying a few shopping bags.

“Stop drooling, pervert,” was all she said as they both headed straight upstairs.

My first thought was to go to bed. Having drank a few beers this evening, not to mention having masturbated several times as well, sleep should come easily. However, I felt well rested at the moment, so I decided to stay up a while longer.

I’d thought that Cheryl and Tim would have turned in soon, but I heard them upstairs talking, with her bursting into occasional fits of laughter. I was taken by surprise when I heard their bedroom door open and Cheryl call down to me.

“Hey, Chris. You freaking pervert! You want to come up and watch us?”

I turned around and looked up at the loft. She was wearing some white lingerie, leaning over the railing to show off her modest cleavage. One foot was thrust partially out through the spindles of the railing. She was wearing the silver cowgirl boots, and rocking that one foot slowly and seductively.

“Come on,” I said. “I know you’re bullshitting me.”

“No, man. It’s true,” I heard Tim call from the open bedroom door.

“We’ll let you watch,” she said. “But only on my terms.”

Of course, there had to be a catch. I was pretty sure they were joking, but she looked so fucking hot. I couldn’t help but ask what the terms were.

“First, you need to strip buck-ass naked. I’ll explain the rest once you get up here. You’ve got one minute before I’m locking the door and you lose your chance,” she called over her shoulder as she walked back into their bedroom.

Now I may be a pervert, but I’m not that gullible. I knew they were setting me up for something. Maybe just slam the door in my face and laugh, just as I got to the top of the stairs.

It also occurred to me that maybe somehow she found out I had masturbated with her shoes and those new boots she was wearing. I could get up to their room naked, where Tim was lying in wait to kick my ass.

Time was running out and my curiosity got the better of me. I’m sure I looked like a fool, quickly pulling off my clothes and running naked up the stairs. I stopped in the open doorway to their bedroom.

Tim was lying back on the bed, wearing only his boxer shorts. Cheryl was standing near the foot of the bed, one hand on her hip, the other brandishing one of her black leather flats.

“You’re a naughty boy!” she said. A wave of panic washed over my body. She had somehow figured out that I had cum in her shoe. “Naughty boys get spanked,” she continued. “If you want to watch, I’m going to give you a spanking first.” She slapped the smooth leather sole of her shoe in palm of her other hand for emphasis.

She was wearing a bustier made of gleaming white satin, trimmed with soft white lace. It had garter straps that hung loosely from her waist as she wasn’t wearing stockings. The matching panties were probably a thong. It was an odd look combined with the silver cowgirl boots, but she was hot enough to pull it off.

“When you watch us, you won’t be allowed to play with yourself,” she further explained the terms. “You’re going to be cuffed to that chair.”

With her shoe, she pointed at a wooden chair near the corner of the room where her shopping bags and stuff were stacked. A pair of handcuffs was lying on the seat. Cheap handcuffs, the kind that might have been bought at a souvenir shop in town, with fake pink fur on the bracelets.

“When we’re finished,” she continued. “I’m not going to let you run downstairs to do your wanking or yanking. You’re going to stay in that chair for a while until you cool off. Understand?”

I cast a quick glance at Tim, who was still relaxing on the bed, as if to ask him if this was for real.

“Dude, it’s whatever she wants,” was all he said. Then Cheryl told me I had ten seconds to make up my mind and started counting them down.

This was crazy. Something that would only happen in some bullshit erotic story that someone with nothing better to do would make up and post on the internet. Yet, there I stood, naked, and starting to get hard, my ex-girlfriend looking so fucking hot all dressed up for a romp in the sack.

“Okay,” was all I said, the word almost croaking in my dry mouth.

When we had been together, I had told Cheryl of a dominatrix fantasy of mine. I had wanted to buy her some thigh high boots and a leather outfit, but she thought that was stupid. She was however willing to spank me with a ping pong paddle on a few occasions.

While that had been some hot foreplay, she never swatted me as hard as I would have liked. I suppose she loved me at the time and didn’t want to hurt me. Therefore, I wasn’t afraid of her spanking me with her shoe, and willingly bent over and grabbed the foot rail of the bed as I was told.

Her boot heels clomped on the wooden floor as she walked around behind me, and placed a hand on one of my shoulders as if to hold me in place.

The thin leather sole of her shoe slapped loudly on my bare ass, and hurt much more than I expected. The swats landed firmly on one of my butt cheeks and then the other, alternating in the predictable way she had spanked me with the paddle.

“You’re a bad little boy,” she scolded, as she swatted my ass even harder. She was taking the dominatrix role that I had always wanted. Perhaps not the same boots or paddle I had fantasized about, but sexy boots none the less, and the spanking hurt just right. Her confidence in the role excited me as well, and my penis was swollen with arousal. However, the spanking was lasting longer than expected, and tears were welling up in my eyes.

“I’ve had enough,” I told her. Cheryl immediately stopped spanking me.

“Come on, you wimp. I know you like to be spanked,” Cheryl said, and pulled me upright. “Look at that little boner of yours!” she squealed. “See, I told you he liked to be spanked,” she said to Tim.

I hesitantly looked up at Tim, still lounging on the bed in front of me. He had a grin on his face and a large tent pole in his boxers, clearly aroused at watching his girlfriend spank my ass.

“You’ll have enough, when I say you’ve had enough,” Cheryl told me in a stern tone, waving her shoe in my face. She told me that if I didn’t let her spank me some more, I couldn’t watch them make love, and she would cuff me to a chair downstairs. “I don’t want you listening outside the door or playing with that little weenie of yours.”

Tim was laughing at me as Cheryl taunted me some more. Again she gave me ten seconds to decide if I would take more spanking, and immediately started the countdown.

Although it seemed she was none the wiser, the punishment was fitting the crime. Spanking me with her shoe that I had gotten off in earlier that evening, not to mention wearing the boots I had masturbated with earlier in the day.

There was no telling how much longer she planned on spanking me, but hoping that taking this short break would somehow make it easier to endure, I bent over submissively and held onto the foot rail of the bed once more.

Cheryl wasted no time and started spanking my ass once again. There was nothing playful or teasing about it. I was being punished. Even though I started to grunt and then yelp at every swat of her shoe, I told myself that I deserved it. After all I had spied on them, looked through their bedroom and masturbated with a pair of her boots and shoes.

For all I knew they would kick me out of their bedroom after the spanking. The promise of getting to watch them fuck having been a lie, and that would be my punishment and I would have to accept it. I gripped the rail with white knuckles, flinching as every swat of her shoe landed squarely on my ass.

“I think he’s had enough, babe,” I finally heard Tim say. The spanking stopped. If not for him she might have gone all night.

Cheryl grabbed me by one of my ears and led me towards the chair in the corner. I cooperated, not daring to resist her. She sat me down hard, the bare wooden seat painful on my sore ass. She fumbled behind me with the handcuffs, and I realized Cheryl had looped the chain through a rung on the back of the chair. I was not only cuffed with my hands behind my back, but also secured to the chair.

“Stop crying, little boy,” Cheryl told me as the last of my tears from the spanking rolled down my cheeks. “Now watch and maybe you’ll learn something.”

She strutted over to the bed in an exaggerated runway walk, hips swiveling, sexy ass provocatively displayed by her thong panties, loose garter straps swaying. Cheryl leaned over and started kissing Tim, their tongues intertwining.

Cheryl took Tim by the hand and led him around to the foot of the bed, and they were only about five feet away from my chair. She wrapped her arms tightly around him. Tim was over a foot taller than her, and he leaned down to kiss her passionately. Cheryl kicked one leg back like you see on old movies, her silver cowgirl boot dangling in the air.

As they made out, she reached down to fondle the large package in Tim’s boxers. He’d been hard for some time now and was no doubt ready to fuck her. Cheryl reached one hand in his shorts and pulled out his cock.

Then she knelt in front of him and slowly pulled his boxer shorts down around his ankles, keeping her mouth just inches from the end of his penis. Seeing his hard cock in the bright lighting of the bedroom, it looked even larger than it had last night. It had to be at least ten inches long and certainly thicker than mine. Standing firm and pointing up at a forty-five degree angle.

“You see that?” Cheryl asked, turning to face me. “That’s a real man’s penis.” Cheryl playfully eased in and lightly kissed the tip of his cock. Her lips were shiny with lip gloss, and she wrapped them around the head of his penis, cheeks going concave as she gave him a few teasing suckles.

Tim gasped lightly, placed his hand behind her head, and tried to force himself into her mouth, but Cheryl wasn’t done taunting me. Turning to face me once again, lightly stroking his cock, she asked,

“How long is Tim’s penis? It must be twice as long as yours. Come on, look at yours and then look at his,” she laughed.

So I looked down at my cock. It was still hard, with pre cum oozing from the tip. The spanking, painful as it had been, had still been incredibly arousing. Now that she was starting to suck and fondle his massive erection, I was even more turned on.

I looked back at Tim’s cock. It was halfway down Cheryl’s throat. She never cared to suck me, but seemed content to give Tim a blowjob. He tousled her long blonde hair, and she periodically flipped it back, probably so it wouldn’t block my view. Her other hand was either stroking the base of his cock or playing with his balls. Tim was moaning and breathing heavily. He would cum any minute now, and Cheryl knew it.

She leaned her head back and looked up at him, lightly stroking his cock, glistening with her saliva.

“I’m going to let you cum in my mouth,” she told him softly. She sucked him a few more moments then turned to me.

“How many times did I let you cum in my mouth?” she demanded to know, but the question what rhetorical. “Oh, that’s right. Never!” She laughed and sucked Tim some more. “It’s so much different with a big penis like this,” she said to me. “You’ll get hard again, won’t you, and make love to me?” she asked, looking up at Tim lovingly and taking him into her mouth once more.

“Yeah, babe,” he said, panting. I suspected he wanted her to just shut up and suck his cock. He placed both hands on the back of her head, but it didn’t look like she would stop to give me any more trash talk. Giving him a blowjob with real enthusiasm now, I saw one of her hands reach up behind his balls, apparently slipping a finger or two into his asshole, something I had always wanted to experience and never have.

That sent Tim over the edge and he grunted loudly, cumming into Cheryl’s mouth. He had a handful of her hair, possibly to make sure she took it all, but there was no need for that as she kept sucking and fondling him until his moaning subsided and his breathing slowed to its normal pace.

Cheryl then turned to face me, gave me a pouting expression and stuck out her tongue. A little bit of cum had run down her chin and she playfully wiped it off with one finger and seductively licked it clean.

She stood up and they kissed passionately for a long time. Then Tim scooped her up in his arms and placed her on the bed. He started to remove her panties, but when he had them down to her knees he stopped and began to pull off one of her boots.

“No,” Cheryl said, pulling her cowgirl boot back on. “He has a boot fetish,” she said with a tone of distain, pointing at me. I’m sure these boots are driving him wild so I’m going to keep them on to make him suffer even more.”

Tim said that was weird and continued to take off her panties.

“You like my boots, don’t you?” she asked me.

“Yeah,” was all I could think of to say.

“If I had these when we were together I’m sure you’d want me to wear them in bed. Too late,” she taunted. “I’ll be wearing them for Tim though, any time he likes. Just remember that.”

I doubted she would wear those boots during sex again, as Tim could seem to care less one way or the other. Without making eye contact with me he tossed her panties towards me in a loose underhand throw. They landed with a whisper of satin and lace just in front of my chair, and it would have been possible for me to touch them with my bare feet. I knew they would be warm from Cheryl’s body, and musky from her arousal, though I wouldn’t be able to enjoy the scent.

Tim spread her legs. Unfortunately Cheryl was lying on the bed so that I was facing her side, and couldn’t see her pussy, which I envisioned would be shaved as she often did, her lips swollen and moist. As Tim went down on her, she turned to me and said.

“He does this so much better than you. Oh… That’s so… good,” she moaned.

She hooked one of her legs around his body, and slowly traced the heel of her boot around on his back. Cheryl gently rubbed his head, which for some stupid reason he kept shaved even though he could grow a full head of hair. She cooed and moaned in a blatant display of overacting, though I had no doubt she was enjoying the experience.

I knew from the years that we were together, that it would take her some time to reach orgasm, and my mind started to wander as I felt a slight itch above my left eyebrow and briefly struggled with the cuffs.

Momentarily I glanced down at the pile of gifts he had presumably bought her, and took a better look at the brochures. Like Las Vegas, it was easy to get married in Gatlinburg, and it seemed as though she had collected pamphlets from all of the many wedding chapels. Not only had I lost my girlfriend to an old friend, it looks as though he planned to marry her.

My cock was still hard, oozing pre cum, some of which had dripped onto the seat of the chair. Watching the couple, I was surprised that Cheryl hadn’t positioned herself at a better angle, and spread her legs widely like a porn star, so I could watch Tim pleasuring her.

She planted the heels of her boots into the mattress on either side of him, and tilted her pelvis up towards his face, breathing heavily. There was no more fake moaning. I knew from experience that Cheryl would soon have an orgasm, and one in record time.

Maybe Tim really was better at going down on a woman, but I suspect she had started to get aroused when she spanked me. Cheryl really seemed to enjoy humiliating me, and I knew it wasn’t over yet.

Her muscles tightened. She gave several long deep sighs, shuddering each time. A long series of multiple orgasms. Tim stayed between her legs, and seemed to be giving a few final, long slow licks, until all of her tremors were gone.

I expected her to tell me something like, that’s how it’s done. Instead, Cheryl got up slowly, catching her breath. Without words she guided Tim and had him lie down on the bed. She gave his cock a few light strokes, though it was firmly erect once more.

Cheryl climbed on top of him and her back was to me now. She leaned down to kiss Tim and tilted her ass slightly in the air, probably so I could see her pussy, slick and shiny with her juices and his saliva. It would have ample lubrication to receive his enormous penis.

Her asshole was also gleaming with the juices that had run down between her legs. A puckered shiny flower. When we were together, I used to lick her asshole while fingering her pussy, as regular foreplay during her period. That had never failed to bring her to a powerful orgasm. One of my perversions that she never did complain about. I doubted that Tim would ever thrill her in that way.

As they were kissing, I could see that he was pulling down the top of her bustier to expose her small firm breasts. She slid forward on top of Tim, and though I couldn’t see, I assumed he was kissing them passionately.

Cheryl twitched her ass a little bit, most likely to tease me, and then eased backwards, the head of his penis barely entering her. To my surprise, she stopped, adjusted her position on top of him, and then slowly took him about halfway in. Her pussy looked as though it was being stretched to its limit. She began to ride him slowly, exhaling loudly and taking him in a little more with each stroke.

Tim relaxed and let her do all the work for now, though he lightly caressed her sexy ass with one hand and I assume the other was cupping one of her breasts. Once she had taken him all the way in, Cheryl looked at me over her shoulder, tossing her head to flip her blonde hair out of her eyes.

“This feels so good,” she said with a tone of satisfaction. “The first time he made love to me with his man sized penis, I knew that you and I were finished.”

Damn it! That means she had fucked Tim while we had still been together!

“Don’t look so upset. I wouldn’t want you to cry,” she laughed. “You were snowed in on a business trip up in Cleveland, so your good friend came over to comfort me in a way that you never could.”

“Hey, babe,” I heard Tim mumble and he pulled Cheryl down to kiss her, or maybe also to shut her up. After that they both seemed oblivious to me. I had thought he was my friend, but assuming what Cheryl said was true, he had sunk low enough to steal my girl while I was out of town.

I still remember that night I was in Cleveland, with I-71 closed due to a blizzard, so I had to stay another night at a budget priced motel in the Brookpark area. As I recalled I had stayed up late looking through my extensive collection of porn photos that I had saved onto a flash drive. Lying on the bed with my laptop beside me, I had played with myself for what might have been hours.

As she continued her slow ride on his massive cock, all I could do was sit there, fuming with rage, my own cock swollen and aching for relief that it wouldn’t get any time soon. My scrotum had tightened up against my body to the point that my balls felt as though they were being squeezed. Not to mention that my ass was still sore from the spanking.

I tried to spread my legs, ease back in the chair a little, anything to get more comfortable. Cheryl’s little black leather flat, which was lying on the floor near the foot of the bed, had stung my behind more than I’d expected. Looking more closely, there were a few drops of liquid on the floor near her shoe. Drips of saliva, cum, or both, left over from when Cheryl lovingly sucked Tim’s cock. She had never given me a blowjob like that, and always finished me off with her hand. For all I knew, he was cumming in her mouth every night.

She was taking her time now, slowly yet purposefully riding his massive penis. I was really surprised that she could take it all the way in. At that moment I realized something. He wasn’t wearing a condom. Cheryl was on the pill when we had been together, but she always insisted on double redundancy birth control. Not only did Tim get to cum in her mouth, but in her pussy as well.

I was at the point where I couldn’t take watching anymore. If I’d been watching a porn video clip, I would have fast forwarded to the cum shot. However, I was stuck in this uncomfortable chair, my penis painfully erect and swollen, oozing pre cum into what was now a growing pool on the seat of the chair.

Trying to let my mind wander proved to be useless. Cheryl had picked up her pace, the unused garter straps of her lingerie swinging and flapping against her sexy ass, rapid breathing almost a whistling sound.

Tim was periodically making these grunting sounds, though he didn’t seem to be anywhere near orgasm. I had cum twice in one night before, with an older lady I’d picked up at a bar some years before I met Cheryl. Sex the second time around had lasted a long time, and I had savored it.

Cheryl squealed in what might have been a second orgasm. It looked as though she might have been fingering herself like you see porn stars do. Then she slowed down, and gently rolled off of Tim so he could be on top.

Her face and chest were flushed, glowing with sweat and sexual satisfaction. As she spread her legs for Tim, I caught a glimpse of her pussy, wet and gaping from impaling herself on his huge penis. She laughed at me as he got into position. I suppose I was a pitiful sight.

Tim was all business, fucking her hard right from the start. I could hear Cheryl gasp lightly after every stroke as he slammed in balls deep every time. Her legs were up in the air to better accommodate him, silver boots gleaming in the bedroom light.

He was lucky to be fucking a hot girl like her, all dressed up in her lingerie and sexy boots, though it seemed he could care less about the extra frills.

The bed springs were giving occasional squeaks now as Tim plowed heavily into Cheryl, pushing her deep into the mattress with each powerful stroke. I heard a catch in his breathing, and then he threw back his head and grunted loudly several times. There was no doubt that his orgasm had been intense and satisfying.

Cheryl lowered her legs and planted her boot heels in the mattress while Tim fucked her slowly and gently. They kissed deeply and she wrapped her arms around him as he emptied every last drop of cum deep inside her.

When at last he withdrew his softening erection, Cheryl wasted no time jumping out of bed and running to the bathroom. I expected Tim to make some smartass remark to me, but he just clicked off the light on his side of the bed, lay down and pulled the covers over himself, apparently ready to go to sleep.

I heard the toilet flush behind the closed bathroom door and Cheryl came out moments later, wearing only a plain cotton robe. She walked over to me.

“I see you enjoyed watching. I’m sure you want to play with that little thing of yours,” she said in a condescending tone, looking down her nose at my swollen erection, quivering above a pool of drippings. “You need to cool off first, and then I’ll release you. Goodnight,” Cheryl said and then she slapped my face much harder than I thought was necessary.

She walked over to her side of the bed, switched off her light, and shed her robe before snuggling up next to Tim.

“I love you,” she told him.

“I love you too,” he replied.

It wasn’t long before I heard Tim snoring loudly. No doubt it would be easy to drift off into a deep and restful sleep after a hot romp like that, and I realized that if Cheryl fell fast asleep, I might end up cuffed to the chair all night.

Perhaps my erection was starting to soften in the darkness, because I realized I had to use the bathroom, thanks to the beers I had drank earlier that evening. It added to my frustration because I was certain that Cheryl had fallen asleep. I could hear her breathing now, deep and slow in between Tim’s loud snores.

I thought that if I tried to wake them up, verbally, or by clearing my throat, or maybe squeaking the chair legs on the floor, that would piss her off and I would have to stay cuffed even longer. Unsure of what to do, I tried to adjust my position to get as comfortable as possible, though that proved to be impossible.

At one time I’d considered buying a pair of cuffs like the ones that were restraining me, and I knew they had little safety latches so the wearer could easily escape if the situation got out of hand. Making my escape at this point seemed like the best idea and I doubted they would care at this point. However, with the linking chain on the cuffs passed through a rung on the back of the chair, I had no slack to work with, and while I fumbled around quite a bit I couldn’t find any release lever.

Who knows how long I sat there uncomfortably in the dark. I knew that a few times I started to nod off to sleep, only to wake up. At last I saw Cheryl move under the covers. I thought she was just rolling over, but she got out of bed and pulled on her robe. Of course she had misplaced the key and ended up turning on a light, waking Tim who rolled over and mumbled loudly. There were no parting words or swat on the ass and I just scurried out the bedroom door, which was closed swiftly behind me and locked.

Making my way down the stairs, I realized I hadn’t even bothered to turn off the TV. I shut it off and picked up my clothes which were scattered on the floor. After taking a long piss, I decided to masturbate before going to sleep. My penis was somewhat achy, feeling almost clogged from that long period of arousal without having an orgasm. I wasn’t horny, but felt it was best to masturbate and release that tension. Maintenance, if you will.

Taking my small tube of lotion, I sat on the toilet to jerk off. It took a surprisingly long time to get hard, and even then I never got solidly erect. Though I tried to envision past hot sexual encounters, and favorite scenes from porn videos, thoughts of my humiliating experience not long ago upstairs kept creeping into my mind, withering my cock in my hand.

I kept at it though, having to apply more lotion at times, and a little spit. It was work, I hate to say. At last I came, and the initial burst was somewhat painful. I stayed on the toilet, slowly stroking myself until I had squeezed out every drop of cum. It was the most unsatisfying time I had ever had masturbating.

I did not sleep well afterwards, and when the alarm went off it was still dark outside. Cheryl and Tim would not be up for several hours, but I left soon after I got out of bed. Didn’t even bother to shower or shave, just made my treacherous drive down the winding mountain road into town, where I picked up a large coffee to go on my way to the interstate. That had been one strange vacation, certainly a memorable one, but mostly for the wrong reasons.

During my drive home I called Scotty and learned that his hasty departure was because a favorite uncle, a really old guy, had been rushed to the hospital and it didn’t look like he was going to survive much longer. In the end though, the man made a full recovery.

We hung out with other friends as usual, at the usual places, though Tim never came around. Over time I learned that he and Cheryl had become engaged, but months later they split up.

One version of the story that I heard was that he broke things off after he caught her not using her birth control, trying to get knocked up so as to get a wedding date set. Another source said that she left Tim for another man who was a doctor or had some other high paying job in the medical field. I suspected the second story was true. Leaving for a man with a larger paycheck and the other guy might also have a foot long penis. I felt some sense of satisfaction when I heard that news.

My new girlfriend is a cute little chunky brunette, who has no problems with my taste for fetishes and other kinky stuff. She has her own twisted interests, such as having sex in public places, and there have been other times when she put a vibrator in my ass while giving me a blowjob, resulting in orgasms so explosive I nearly passed out. All stories for another time, perhaps.

The End.

 

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