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By ChristopherDB (edited)
It was around 10:30 on a Saturday night when I left my shabby Rowhouse in the valley. It was a lower-income working class part of town, considered by many to be the wrong side of the tracks. I had moved there from a nicer suburb in order to save money and pay off some bills.
Walking around the corner, I could see my destination only a few blocks away. The valley had an amazing number of little neighbourhood bars. There must have been ten of them in a five block radius of my house. That night I was heading to Redman’s.
All the other bars seemed to be full of old drunks. I’d heard that Redman’s was the valley’s version of a dance club and had a reputation as being an easy place to pick up chicks. Now I’d met some real babes at the upscale clubs downtown by the river, and had my share of one night stands. If I could find some decent pussy literally around the corner, life would be pretty sweet.
There was a short line of people at the door, but none of that downtown attitude, making some people wait and so on. The doorman looked like some old biker, and he was only interested in checking ID’s and collecting a small cover charge.
The place was packed, but then again, it was a small club. I was able to get a beer pretty quickly, from a stunning redheaded barmaid that was wearing some tight black leather shorts with some black fishnet pantyhose.
All of the stools at the bar were taken so I started to slowly walk around, checking out the place and the crowd. Although it was a younger crowd, I hated to admit it, but it looked like the barmaid might have been the hottest lady in the room.
I was working on either my third or fourth beer and not having any luck striking up conversations with women. Suddenly it hit me that despite being a dance club, the place still had the feel of a neighbourhood bar. It might be an easy place to score once people know who you are, but I was a new face in the crowd and might have to stop at a few more times before I had any success. Figuring I would just finish up my brew and then walk home, some girl waved me over to her table.
There were three women and two guys crammed into this circular booth by the dance floor. Judging by the pile of beer bottles on their table, they had been partying for a while. The young lady that had called me over was a cute but rather chunky brunette. She had an amazing set of tits that barely fit into her white tank top.
After she introduced herself as Lisa and made introductions all around, I quickly figured out that the others were two couples, and Lisa was the fifth wheel tonight. One of the other ladies, who was older and a bit heavier, wearing some gaudy shiny gold dress, said that I looked familiar.
I casually mentioned that I’ve played bass with a few local bands around town and she might have seen me jamming at some other bar. Though I was between bands right now, I told them I had just started renting a house with my old guitar player, a few blocks away. I’ll admit it was a shameless ploy to establish some credibility as a local.
Somehow they made room for me at their table. We drank some beers, had some laughs, and later on I was out on the floor dancing with Lisa. She was looking really fine with those super-sized tits, and wearing this short plaid skirt like a naughty schoolgirl. I’ll admit to having a fetish for boots and Lisa happened to be wearing these sexy black leather knee-high boots, which had heels that might have been about four inches high. That really topped off her slutty sex appeal for me.
After a slow dance I told her that I still had some unpacking to do at home, but I had put my bed together, and suggested that she come over for a little while. Lisa gave me a devious smile, and then a kiss with a deep probing tongue, and said we would go to her place instead.
There were no long goodbyes with the other couples. In no time at all we were making our way down the narrow sidewalks, with Lisa’s high-heeled boots clicking loudly in the darkness.
“I like your fuck-me boots,” I told her. “They are really sexy.” She laughed, and asked me if I wanted her to keep them on during sex.
“Hell yeah,” was all I could think of to say.
Lisa’s place was only a few blocks away, some big old house that had been divided up into a bunch of apartments. As she led the way up to the second floor, I couldn’t help but reach a hand up under her skirt to grab a handful of her plump ass.
“Now wait just a little longer,” she said, playfully slapping my hand away. I did as I was told, but I was really aroused now. I’d had a handful of bare ass. She was wearing a thong, or who knows, maybe no panties at all. Fuckin’ hot.
When we walked into one of the apartments at the top of the stairs, I was really surprised to see some dude sitting in one corner of the tiny living room, hunched over a computer. He was kind of heavy-set, wearing grey sweat pants, with his thinning hair pulled back in a stumpy ponytail.
Lisa didn’t even bother introducing him and as she led me to her bedroom I laughed to myself that this loser had been sitting at home all night, probably surfing for porn and spanking his monkey, while his hot roommate was out partying, and now he’d have to listen to me fucking her.
Her bedroom was tiny and cluttered. She took a long time lighting a bunch of candles on top of the dresser and nightstand. At last we sat down on the edge of the bed and started making out.
Now I really wanted to spill her big boobs out of her top and get my hands up under her slutty skirt, but I restrained myself. Deep passionate kisses, periodically nibbling on her ear lobes, and kissing her neck. I wanted to get her really steamed up, and it worked.
By the time I had just begun to lightly caress her tits through the thin fabric of her tank top, it seemed she could take no more, and she boldly thrust her hand down the front of my jeans and grabbed hold of my cock.
Suddenly she broke off our kiss and in the candlelight I could see she had a sour look on her face.
“Drop your pants,” Lisa said, sitting back on the bed with a sigh.
I stood up and unzipped my jeans, dropping them and my boxer shorts around my knees. My cock was rock solid and I moved closer to the bed so she could suck on it.
“I’m sorry,” she said, staring at my erection. “For me, I just need something bigger.” The tone of her voice was apologetic, but with a hint of laughter. I couldn’t believe it.
Now I’ll admit my penis is smaller than average (Bronze Member of The Small Dick Club). However, that had never been a problem with former girlfriends, band groupies, or conquests I had picked up at any downtown clubs. At least none had ever said so.
Otherwise, I’m a pretty big guy so maybe she was expecting some giant piece of meat down there. It was clear that she was disappointed and I wasn’t going to get laid unless I did something fast, so I offered to go down on her and said that I knew I could satisfy her.
“Well, okay,” she said with a secretive smile. “But I’m going to put your skills to the test.”
I wasn’t sure what she meant by that as she stood up and dropped her little short skirt to the floor. Then she turned around and told me to kiss her ass.
Horny as I was, I didn’t hesitate and got on my knees. The pale skin of her plump bottom was beautifully framed by her white thong panties. I kissed her soft, warm butt cheeks with the same passion that I hopped to apply to her ample breasts in just a short while.
Then Lisa stepped out of her skirt, spread her feet about shoulder width apart and told me to lick the crack of her ass.
Although I didn’t find that appealing, I did as I was told, lightly tracing my tongue up her backside, not probing in deeply enough to rub against the narrow thong clenched between her butt cheeks.
That’s when she spread her legs wider, reached back and hooked her thong off to one side, then grabbed me by the hair and pushed my nose and mouth into the crack of her buttocks. So I deeply licked the crack of her ass, slowly and lovingly, though avoiding her asshole.
This seemed to piss her off because she bent over further, grabbed a handful of my hair once again and forced my head into position.
“Come on,” she said mockingly. “Show me those amazing skills you said you have.”
Lisa knew I was under her control at this point, and I gave her puckered anus a tentative lick with my tongue. I had expected it to taste bad, but there wasn’t any real flavour or bad smell. Maybe she had taken a bath before going out tonight. So I just started licking her asshole with as much enthusiasm as I could, hoping she would drop her thong and let me lick her pussy, then eventually let me fuck her. Degrading as the situation was, I still had a stiff erection and was aroused as I could be.
Lisa started breathing deeply and I thought she might even cum. I knew the asshole could be an erogenous zone and I was clearly turning her on. Then she stood up and turned around, and forced my nose against the crotch of her panties. They were damp and fragrant with the scent of her arousal.
She kept asking me if I wanted to lick her pussy, and if I wanted to lick it really bad, and each time I said yes, my voice muffled between her legs. Lisa said I would get that chance soon enough, and then to my surprise, she just walked out of the room.
I overheard some conversation in the next room and next thing I knew she was coming back into the bedroom, leading that dude from the living room by the hand.
Lisa knelt in front of him and pulled down his sweatpants and tighty-whities. Even in the dim lighting I could see that this guy’s limp cock was way longer and thicker than my hard-on.
She gently wrapped one hand around the base of his penis and then took it into her mouth. Lisa began to suck him slowly, taking in as much as she could, and looking like she was savouring every inch. It’s rare to find a chick that really loves to suck cock, but Lisa seemed to be one of them.
The dude got hard in no time and he was hung like a freaking porn star. The dudes cock looked ten-inches long, and as thick as her wrist. Looking down at my four-and-three quarter-inch dick I began to feel deflated and humiliated. I had never really considered myself small before, until this night.
Lisa never took him completely out of her mouth, though many times she would slowly withdraw to the point where only the tip of his penis was held tightly in her lips. All the while she lightly stroked the base of his cock or fondled his balls.
She flipped her hair back a few times, probably so as not to block my view, but otherwise the two of them ignored me. The guy started breathing heavier and he pulled off his glasses. He set them on the dresser while Lisa started taking his massive cock deeper into her mouth.
The way things were going, I was pretty sure he was going to cum in her mouth any second, but then she stopped sucking him, tossed her thong panties in my general direction, and pulled him down on the bed.
Right from the start he rammed that big cock of his all the way in, and Lisa let out a deep gasp. He then started to fuck her with thrusts that were long and slow, yet heavy, pounding her big ass deep into the mattress each time. Lisa was gasping and moaning loudly. She sounded like she was in pain, yet enjoying every minute of being stuffed with that oversized penis.
Now I’ve watched my share of porn, but seeing two people fucking in person, the scent of sex mingled in the air with all those candles, it was the most intense thing I’d ever experienced. I couldn’t help but start jerking off.
Lisa glanced over and saw me playing with myself. She told me to cut it out or I wouldn’t get any sloppy seconds. So I stopped, my erection straining for relief.
Then Lisa started kissing this dude passionately, and put her legs high up in the air so he could thrust himself in even further. Of course she hadn’t bothered to take off those sexy boots, their spike heels then pointed at the ceiling. Damn, she was going to keep those on for me. It was going to be some hot sloppy seconds.
Then the guy started to fuck her faster, slamming in balls deep with every stroke. The bed springs were squeaking and groaning in protest, almost to the point of drowning out Lisa’s moaning. At one point the headboard of the bed started to knock against the wall and I was pretty sure every neighbour in the building was awake now listening to this bitch getting fucked.
Then the dude let out several loud grunts, evidently cumming deep inside her, and he slowed his pace, panting and seemingly out of breath. Lisa was breathing heavily, but paused to give him one last deep kiss. Then this guy just got off the bed, pulled up his sweatpants, put on his glasses and left the room without saying a word.
Lisa sat on the edge of the bed with her knees pulled up to her chest and called me over. After kneeling in front of her as instructed, she told me I would now get the chance to lick her pussy.
She spread her legs and I could see her snatch was still gaping from being fucked by that monster cock, and it was wet with her juices as well as the guy’s cum, which was starting to ooze out.
Before I could back away, she had grabbed my hair and forced my mouth into her cream pie, ordering me to lick her clean. I licked hesitantly, and fortunately the taste of her pussy mostly outweighed any flavour of that dude’s cum.
I thought a few licks were all she would want, but she didn’t let go and kept my face buried in her crotch. Lisa eased her legs down to the floor on either side of me, then big gobs of cum began to run out of her pussy and into my mouth. As I tried to back away, she tightened her grip on my hair and painfully forced my head between her legs to the point where it was tough to breathe. It seemed there was nothing I could do but keep licking her clean, and I was at it for what seemed like a long time. I probably licked every drop of cum out of her before she finally released me.
“Now let’s see how much cum we can get out of your stubby dinkus,” she said, spitting several times into one hand and then reaching down to jerk roughly on my penis, which was still hard as could be.
“You like my sexy boots, don’t you?” She asked.
I answered yes through my clenched teeth as she painfully yanked on my cock.
“I’ll let you cum on my sexy boots,” she said. “You’d like that, wouldn’t you?” She asked, laughing.
Lisa started to say something else insulting about the size of my cock when I came in several long spurts, shooting on one of her black leather boots.
I was relieved when she released my penis from her firm grip, but as I watched my cum run down the shaft of her, but she told me that I would have to lick it up. Though I tried to protest, she told me that it was time for me to taste my own cum and raised her boot up towards my face.
I suppose it was better to taste my own cum, but licking it off of her boot while she mocked me for cumming so fast was perhaps the most degrading part of the night. Once I was done, she had me lick the entire boot, even the sole, and the other whole boot as well.
Lisa then rushed me out of her apartment like a bum and as I started to walk home slowly on the dark streets, I pulled her thong panties from one pocket of my jeans. I had slipped them in there is a souvenir as I had gotten up off her bedroom floor. Giving the musky thong a deep sniff, I considered tossing it into some bushes, but then put it back in my pocket and regretted not getting to see her tits.
That night had really torn me apart. It had been completely degrading, some skanky bitch telling me my penis was too small, having to worship her asshole, and then watch her get fucked by some other dude. Not to mention having to lick her clean and then lick my own cum off her boots.
On the other hand, that night I had never been more aroused in my life, and Lisa’s rough hand job had climaxed in one of my most intense orgasms ever. I thought about that experience often and held her thong panties tightly to my nose while I masturbated my stubby dinkus, as she had called it.
I returned to Redman’s a few more weekends after that and got no respect from anyone. Any woman I approached seemed to take a quick look at my crotch and put an end to my attempt at conversation. Even though I never saw Lisa in there to spread any gossip, the valley seemed to have the rumour mill of a small town.
It seems that she left the area shortly after that one night I went to her place. Driving by the old house I saw a FOR RENT sign in one of the upstairs windows where Lisa’s apartment was. Curtains open with a dark and empty room beyond.
I stayed home most weekends practicing the bass guitar. I didn’t want the humiliation of facing the women at Redman’s, but to be honest, I was also afraid to pick up any ladies in the downtown clubs. Afraid to be told once again that I didn’t measure up.
I would stay in the valley for another eight months or so, taking advantage of the low rent and paying off bills as planned. At one point I took a night class that led to a promotion and good pay raise at my day job, and all that practicing on the bass landed me a gig with one of the best wedding bands in town.
When I moved out of the valley to a nice apartment in a northern suburb, things started really looking up. I had dared to fuck some drunken bridesmaid in a back room during a wedding reception, and she was on my cock with enthusiasm the moment I dropped my pants. I was back in the game.