Ugly duckling

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 didn’t 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 it’s 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 didn’t 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 wasn’t 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 didn’t 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 don’t 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 other’s 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 it’s 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 it’s 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 didn’t. 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 it’s 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 don’t 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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