Ugly Duckling
- 4 years ago
- 49
- 0
Introduction: homely teen gives her tight virgin cunt to her dream boy Her name was Barbara, she lived not too far away from us across the railroad tracks in a shack of a home that her poor family rented. Barbara was an outcast, she attended school with us but no one spoke to her much. She had some deformities that made her walk with a hobble and her face was almost gruesome. One side of her face was misaligned and her left eye was enlarged, the left side of her jaw protruded down and to the left making her lower lip always hang partly open.
I must say that for a bunch of middle school aged kids, we did well, I never remember anyone making fun of Barbara or giving her a hard time. But still, she was outcast. The teacher rarely called upon her in class because she knew that it was embarrassing for Barbara to speak. She could talk, but it was a slurry and drooling speech that seemed to agonize her as she spoke. At recess, or in the lunchroom, she sat nearby but alone. Many times I caught Barbara staring at me during class, she would smile at me but never spoke.
Between her house and mine was a large lot full of railroad maintenance materials, big piles of gravel, crossties, sand, culverts, scrap metal, and all sorts of other stuff. This junkyard was a favorite playground of mine. I was often hanging out there, sometimes just playing, sometimes hunting rabbits with my dog and a pellet gun. I never knew that Barbara often watched me from a dark window in her house across the creek.
When I started high school, we saw no more of Barbara, nobody really missed her, I guess I may have wondered what became of her but I figured she was sent to some special ed. facility or something. By the next summer, after my freshman year, I was becoming a horny young man, and my trips to the junkyard playground often became masturbation sessions. Sometimes I would crawl up into a large culvert and curl up there to beat my meat, but my favorite spot was a tiny shack that was in the edge of the woods, it may have been an old ticket booth or something, it was tiny, about six foot by six foot with a shelf along one wall. The shack was all grown over with vines and brambles and I felt safe in there knowing that no one would dare pick their way through the briars and snakes to gain access to the old shack. It was my fuck shack, I arranged the junk on the inside so that I could have room to sit and face the shelf, the shelf was about waist high, a good place to spread out a girlie picture, with plenty of room beneath it for me to stroke my young dick. Before long, I had a collection of photos of beautiful women, some clipped from magazines, some were catalogs showing pretty women in bras and panties, and I often had some kind of lube, hand lotion borrowed from my mother and carried there in a plastic bag. I kept all my stuff carefully stowed on a board overhead in the rafters of the tiny shack.
One day I discovered that my stash appeared to be disturbed, the clippings were out of order from the way I had left them, this gave me reason to look over the premises, and I could detect that someone else had indeed visited the shack. I resolved to figure out who had discovered my fuck shack, I would not feel safe jerking off in there until I did.
I spent a couple of days just watching the area from a distance while riding my bike but saw nothing. On my next trip to the shack, I got a funny feeling as I approached it, something just didnt seem right. I backed away and hid among a pile of old machinery. I sat there for twenty minutes or so when I saw movement at the door of the shack. A small figure slowly emerged from the building, carefully closed the door, and began picking its way through the vegetation. It was Barbara! I watched her as she hobbled her way across the creek and up the bank towards her house.
I entered the shed just a minute or so after she had left, I carefully observed the site trying to discover what she was doing there. Sure enough, she had looked through my stash again and I could detect a new musky odor in the small building. What was odd was the lust that overcame me as I smelled her presence and thought of how this girl with a real live pussy had just left this very spot. I jerked off and shot my cum onto the shelf as I had done so many times before, only this time, I didnt need to look at pictures, my thoughts were on ugly Barbara and her body. After shooting off, I pressed my dick onto the shelf and with my pocket knife, scribed around it so that on her next visit, she would see the outline of my dick carved into the wood.
Two days later, as I revisited my shack, I approached it halfway hoping that she would be in there, the thought scared me and turned me on at the same time. She wasnt there, but I soon found that she had discovered my self portrait. There was a little pencil lying atop my carved dick, with this pencil, she had drawn around the outline of her legs, crotch, and butt as she had sat upon the shelf. My dick throbbed as I looked at the outline of her buttocks and her spread legs. She had been sitting so that the tip of my carved dick pointed straight to her crotch! And as I looked closely I saw a dark curly hair lying on the shelf, it had to be her pubic hair! Soon I was shooting sperm into her drawn features. I was shocked at how captivated I had become by this gruesome girl. Before leaving I scribbled Tuesday night 7 oclock on a small plank and leaned it on the shelf.
To be honest, I was getting scared. I was wanting to meet her and see where this would lead, but I had always been afraid of girls. I didnt have much hair on my pubes and my dick was smaller than most guys that I had seen so I was somewhat afraid of letting a real girl see me naked. But this was Barbara! Who could she tell? And who would believe her anyway?
I was at my shack at ¼, till seven, I was trembling with fear and excitement. Would she show up? Would I gross-out at the last minute when I saw her up close? I heard noises in the bushes outside, then a soft knock on the door. I opened the door and looked at her. She had maintained her gruesome features and she had not grown much since we had been in school together but her breasts had swollen considerably. We stared at each other for a moment, and then she slid in through the door beside me as I carefully looked over the area to see if anyone else was around. I closed the door and faced her. She just looked up at me with her pitiful deformed face. She was very short, she stood maybe 4 ft. 8 inches tall, petite, with scraggly long black hair. She just watched silently as I removed my t-shirt, she looked at me for a minute before she began lifting her t-shirt up to her shoulders. I dont know what I was expecting, maybe some kind of deformed and chapped teats hanging there, but it was not, she had beautiful tits, I reached out and grabbed my first ever handful of real-girl breasts. I bent over and licked them, the points of her breasts tightened and began protruding from her dark nipples.
She let out a soft moan and stepped towards me and pulled us together so that her breasts mashed into my bare stomach. I leaned forward and kissed her on top of the head. Her head sprang up and she pulled me down to her and kissed me with her deformed lips, it was her first kiss. I dropped my jeans to the floor as she stood there watching, then she did likewise. We stared at each others crotches, both hesitant to reveal our entire naked selves to each other. Then she turned around with her back to me and started peeling off her threadbare panties. She then climbed on the shelf and sat there watching me with her legs closed tightly together.
I shucked my briefs and my stiff cock sprang free, the penetrating stare from her enlarged eye bounced back and forth between my dick and my face. I slid by her and sat in my place directly in front of her, staring at her crotch and fondling her tits. Her whole body was so warm! My hands dropped to the smooth skin of her thighs as I gently urged them apart. She allowed me to spread them, I was not expecting to see such a mass of curly dark hair, I ran my fingers through it and across her warm crevice. She was breathing heavily. I stood and moved forward so that she could see and handle my dick. The touch of her exploring hands sent jolts of electricity throughout my body as she stroked and rubbed my cock and balls. While she fondled her first cock, I started exploring her breasts with my mouth. She gasped with excitement and leaned forward into me. The next time I ran my fingers through her pubes, something was different, the crevice I had felt earlier was now a moist slit, and as I ran my fingers through it, Barbara panted and squeezed my dick.
I knew ugly Barbara would let me fuck her now. I wanted to do it just right, so I began positioning her with her asscheeks right on the edge of the shelf, I then spread her legs and had her place her feet up the stack of boards behind me. We both held onto my cock as I rubbed it around her crotch. I was a bit unsure about where her hole was so I began probing with my fingers around her moist flesh. I could not find any opening! Finally, once while she rocked her hips up, my finger penetrated a tight little hole near the bottom of her smooth gash. As I inserted my finger to the first knuckle, I thought to myself, there is no way that even my little dick could squeeze inside there.
I stepped back and aimed my prick at her dark patch of hair and started rubbing my soft swollen cockhead up against her slit, her smooth skin was so warm! I wanted to push inside her and feel the heat of her insides, but her tiny opening was much harder for my dick to find than it had been for my finger. When I pushed forward my cock slid either up and into her nest of pubic hair, or down and between her taught butt cheeks. I leaned her back against the wall and spread her legs further apart, when I did this, it changed the shape of her opening slightly, now there was a slightly protruding mound of flesh at the bottom of her slit that helped to hold my trembling dick in place as I tried to push it into her. I eased forward and was rewarded by the disappearance of half of my swollen knob onto her tiny orfice, but that was it, as I tried to push further, she squealed and pulled her hips back away from me to ease her pain. It dawned on me that I needed lubrication, I had jacked myself off enough to know the wonders a little slobber can do.
I backed off of her and rubbed spit over the length of my cock. I finally spoke to her, come back here Barbara, as I spread my shirt over the wooden shelf for her to sit on and once again pulled her hips to the edge of the shelf. The fact that I had actually spoke to her and made her a seat from my t-shirt seemed to put her back at ease. I aimed into her opening and slid just a little easier into her shallow embrace. I pressed forward but my cock gained no more ground, I probed from different angles and tried to spread her opening with my fingers but nothing worked. I was thinking this must not be the right hole and was just about to give up when Barbara rolled her hips up at the same time as I probed forward and my rock hard little pecker slid a full inch and a half into her. She started to scream and tried to pull back but I held on to her ass, leaned forward, and kissed her lips. She screamed into my mouth as I rocked into her further still, my entire being was focused on the incredible feelings my cock was experiencing in the only virgin cunt I would ever fuck. I was nearly half of the way inside her when my thighs hit the bench, preventing me from going deeper. Now I withdrew, I needed to re-adjust and I knew also that I was just about to come and I wanted to hold back until I had felt myself all the way inside her.
After adjusting our position, my throbbing dick feverishly probed its way back into her tiny slit, I paused and looked up at her face and nearly stopped altogether, she was curled forward with her head as close to her crotch as she could get it, she was drooling from her open lip and her head was twisted so that her swollen eye watched the fascinating scene of my stiff prick forcing its way into her tiny cunt. It was repulsive. But as my gaze dropped to her drooping tits and her hairy gash, and my cock felt the squeeze of her warm pussy, she once again became beautiful. Her arms wrapped around my neck and she braced herself tightly as I forced my way back inside her. Again I closed my eyes and kissed her mouth to muffle her screams and pressed forward. This pathetic and monstrous little girl, after a lifetime of shame and neglect, had her dream boy totally consumed with desire for her. She struggled to keep her place on the bench with her legs spread wide as I pushed into her. I was expecting to hit some kind of wall in her tight pussy, but I didnt. It was more like a super tight sleeve that seemed to stretch around my dick in a series of popping spasms. My soft cockhead steered its way up her tight tunnel, my stiff shaft followed it and forced apart the tissue that had remained undisturbed inside her for sixteen years. I was overcome with feelings that this girl was doing everything in her power so that I could enjoy this ultimate pleasure.
We panted excitedly into each others mouths when we realized that I was now inside her completely. It was a shock to us both that her tiny tube now tightly held the entire length of my swollen dick inside it. I had heard that you were supposed to go in and out of a girls pussy, but there was no way I was going to back out even a fraction of an inch from that wonderfully warm and tight embrace. Even though I was bottomed out inside her, I just kept shoving deeper and deeper, trying to feel the warmth a thousandth of an inch deeper inside her virgin cunt. With each shove forward, Barbara squealed through her deformed mouth. The warmth of her clutching organ was wonderful beyond description. My sensitive young prick could feel her insides throb with her every heartbeat.
After 30 seconds or so of pressing into her, the super snug grip her cunt had on me seemed to grow warmer and even tighter as my cock began to swell in preparation for ejaculation. I was overwhelmed knowing that she was struggling to give me her most sacred possession, and in a few short seconds it was my turn to moan into her mouth as my orgasm shook me to the core. I dont know if it was her pussy or my cock that was doing it, but as I began to release my seed, I could feel her velvety smooth cunt walls milking my throbbing shaft. She was trembling and gasping for breath in rhythm with my pulsating cock that throbbed with each wad of thick sperm that I deposited inside her. I could feel her opening grow slick with my sperm as I involuntarily shook back and forth and probed even deeper into her tight tunnel.
Ugly Barbara and I clung to each other tightly, I had to hold onto her just to keep from collapsing. There was total silence around the shack, except for our rapid breathing and the buzz of flies that were being attracted to the smells of our sex. Slowly, I felt my cock softening inside her and her tight hole began forcing me out. This was another incredible sensation that I had not expected, it was like I could feel every detail in the walls of her pussy as her organ was shitting my cock out of her. We both watched as my purple cockhead popped free from her, followed by globs of milky cum mixed with blood from her abused hole.
Barbara was sobbing and tears flowed from her deformed and swollen eyes as she slid off of the shelf. I did not know what to do, so I just stood there and held her. I could not believe that I had just fucked her, Barbara! The monster! She was scary looking, she was repulsive, but still I could not suppress a sublime feeling of love for her after she had provided me with this most precious gift.
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If there was one thing Eric and Clara had in common it was their ability to play with fire without getting burned. In every other possible regard they differed, positioned firmly on opposing sides of their social circle and often enough on opposite sides of the room. It was a gap love could not bridge, and neither of them fell victim to any illusion in that regard.But the bridge they had found was much more powerful, dangerous even in that they shared their love for destructive relationships....
Tom loved it when he visited England, not just because of the beautiful countryside and the familiar customs he had left behind 16 years ago but because he absolutely loved English women .. Some people found that odd, Latino and Asian women were usually what tickled a man’s fancy but for Tom, it was mostly about the accent. It turned him on a LOT. The last time he had managed to wrangle a trip to England had been three years ago and that was only for a long weekend for a cousins wedding. He...
TALK TO ME by Throne Sitting at his desk, Robin Manchester reviewed the impressive number of accounts on the screen of his computer. He never had trouble getting new ones and holding onto old ones. The company he worked for had just begun representing a concern that did licensing for sports teams. Some people thought Robin was not the best person to deal with those products. He was small and slender, not a fan of the major leagues. It was also significant that his voice was soft...
Hi, readers of Indian Sex Stories dot net. It’s been a while I had posted any stories about me like 1 year. But I was reading all the stories. Many of you will agree to this, some of us like to read such a sex story rather than seeing porn videos while sleeping on the bed at night. So coming to the sex story, myself Anjuman of Odisha. I am 5’9” not very much good looking but I am pretty good to impress a girl. It’s a quite long sex story, everybody knows how much time it needs to take a girl to...
Hello guys, I am trying my best to describe my journey as a shy teenage guy to committed lover guy moved abroad(US) to pursue masters to naughty working guy. This might be boring for few people, for some it might look like reflection of their life. I will try to be concise in this piece so I can best efforts to make it interesting for ISS readers. Nevertheless, I will write all my experiences and publish on this medium which has forced my hands into my shorts at night for most of the last 8...
Once we finished eating, Sharon and Dave cleaned up. Sharon said, “Dave and I are going walking. There’s a pool and I want to locate it for this afternoon.” Misty pulled me out of the bench seat so I followed her out. We walked following Sharon and Dave down the roadway. We found the pool easily. It looked inviting. I touched the water and found it cool but not uncomfortably so and said so. We continued to walk circumnavigating the entire park. It was a good walk and Misty and I held hands...
Cock on the TrainI took a train to work all the time, every day. I loved riding the train. It was inexpensive, not nearly as bad as driving to work and fighting traffic and the wear and what have you on your nerves, the car, and all that.I also discovered a few things about the people who took the train. I also discovered the best way to flash people on the train.I had to drive to work on weekends, but, I got up every Monday and Tuesday, my days off, just to ride the train around to town and...
After a wide range of experiences as a gigolo, I developed a preference for a certain type of client: elegant, sophisticated women aged around forty five years old, with bodies anywhere between size ten to fourteen and not overweight. They were often a long way from home on business. Almost without exception these women would be very good communicators, uninhibited and able to articulate their sexual preferences. And if they enjoyed what I had to offer and recommended me to others that was an...
Passion In James County XIX: Family Affairs Chapter thirty-eight Mary, totally nude, sat at her dressing table, combing and blow-drying her hair after her delightful shower with Matt. Her young lover, also nude, was wandering around the bedroom behind her. He paused in front of her open lingerie drawer. ‘The stuff in this drawer is really neat!’ he commented. He reached in and touched the dainty under things. ‘You have some really sexy stuff.’ Mary felt herself blushing. ‘I…I bought those...
I was having this conference that was running for 4 days and I was soexcited about it cause I just arranged to crash on one of my old mates'couch.One of the dudes back in collage. I remember we were a huge group of guysbut now as life goes on , it took us here and there and everybody goes withtheir own life, living in different citites and states.His name is Josh. Josh is a tall blue eyed guy, long blond curly hair witha body of a swimmer. We both now are 28 years of age. He had a hairlesschest...
This is another fantasy with a gay slant involving a man and a shemale. It is written for those that appreciate such things, please leave a thumbs up if you like it and feel free to comment. If you want to give it a thumbs down would you be so kind as to tell me in a comment why you didn’t like it?“This will be very hard to explain,” I thought as I felt the tip a cock against my lips and I opened my mouth sucking that small cock head into my mouth. I had never sucked a cock before and at times...
Julia fairly stumbled into her family room, grabbing onto whatever she could to maintain her balance. She had fallen asleep in another room at the tail end of the New Year's Eve party she and her husband had thrown that night. She passed her husband on her way to the family room. Even in her severely inebriated state, she could tell that he was in even worse shape than she was. Julia saw her son sitting on the couch and she moved in his direction. But she couldn't quite make it without...
I was up and at it early again Saturday morning with rather pleasant thoughts from the night before. Mom hustled me to grandpa’s shop and I went to it. Grandpa had clearly made more progress on the pit cart, with some metal cabinet doors now in place, along with a thin steel plate top. Work benches were getting cleared off and this was starting to look like a proper race shop again. Grandpa was out to help about an hour after I arrived. He ambled into the shop with a big thermos of coffee...
Batista entered Angel's room and she was lying face down on the bed sobbing. He sat down next to her and placed his hand lightly on the back of her head, running his fingers gently through her hair, "Shhh," he soothed softly. "Why did you bring me back?" She turned around and he pulled her up into his arms. Batista kissed the top of her head and held her for awhile, "C'mon, let's get you cleaned up," he said after awhile and led Angel into the bathroom and began to fill the tub...
Als ik mijn seksleven bekijk, dan wordt ik met regelmaat seksueel bevredigd door mijn seksvriendinnen. Ik ben goed geschapen, de lengte en omvang zijn bij volledige erectie meer dan gemiddeld. Ik hou ervan goede seks aan mijn meisjes te geven. Ik ben na jaren hardcore seks tot de conclusie gekomen dat zelfs de grootste frigide vrouw door een grote stijve pik om te vormen is tot een geile teef. Ik heb inmiddels een roedel teefjes om me heen verzameld en als een echte man pas ik vrij goed op hen....
The sun was shining brightly this particular morning in the mining town of Fort Cibu. Warstomp yawned as he came to life from his nightly slumber. He was a large, sturdy, brusque, charcoal-colored, ork. Warstomp was a corporal in the Peace Protection Corps of the Provisional Army of the Tarki Masni Territories. He worked at the mine keeping order, ensuring no unauthorized personnel got through, and identifying and exterminating potential threats to the safety of the workers and the quarry...
by Micaela Reynolds as told to BrettJ © 2009 * I am very happy to say that I live my life the way I want, with the love and desire of my family surrounding me. I can have sex whenever I like, there’s always a willing partner. If Debra isn’t around, I can avail myself of Paul or Chris, if I want a female, my adorable Sharon or her hot-as-a-pistol stepsister will sate my urges. Not many people have this kind of luck. Lately, I’m even back on speaking terms with my family, although they’d all...
My fiancé Aidan and I have this friend, his name is Jake and I have a pretty bad crush on him. He's just moved over here from another country and he's staying with us for a while until he gets on his feet. He's been here three to four weeks now and each day my urge to have him is growing stronger by the day. I make my mind up and decide that tonight will be the night. I'm having a long hot shower and a shave, in all of the right places. I finish up, straighten my hair and put a little make-up...
Wife LoversOn the cheerleader front, after all the fun Katherine, Alan, and Kim had in the storage closet, and Kim's generous offer for them to use her house, neither Katherine nor Alan brought up the idea of counter-blackmailing Kim again. In fact, if anyone was in the driver's seat now in terms of setting rules and an agenda, it was Alan first, Katherine second, and Kim last. The fact that Kim was much younger made it hard for her to stay in control. She could easily have blackmailed both Alan and...
Paul and I had completed the job we were sent to do in minimum time. We got up early Saturday morning, checked out of the hotel and were on the road by seven o'clock. The day was going to be sunny and cool, perfect for traveling the hours long trip home. The miles rolled by without my noticing. I was thankful that Paul had volunteered to drive because my mind was in turmoil debating how to handle the situation. Should I tell her. Should I not. Paul must have known what was going on in my...
Asian spinner Vina Sky gets pounded hard by Mick Blue. Vina is the definition of Young & Glamorous, with her sexy little body tightly wrapped in black lace lingerie and matching high heels, she’s sure to turn anyone on. She teases you seductively as she makes her way up the stairs, removing her bra and thong in the process, then makes her way to the couch where she finds Mick waiting for her. Mick picks her up as he kisses Vina, then lays her down on the couch and spreads her legs wide so...
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