Italian shemale has her ass fucked deeply

Italian shemale has her ass fucked deeply
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Most of that summer passed without me seeing Barbara again. I tried to keep myself from trying to meet up with her again, but every 2 or 3 days I could not resist visiting our "shack" hoping to meet her. Nearly a month went by with no contact with her and then at last there was a note left for me on the shelf where she gave herself to me.

It read, "I love you, they won't let me leave, I saw you twice from the window, I love you, Barbara". I was comforted to know that the reasons I never saw her were beyond her control, and that she still kept watch to see me through her window.

"It's just as well" I thought, "I was going to have to stop seeing her any how". But Barbara was always on my mind. At the restaurant where I worked some during the summer, a hot and cute waitress, two years older than me, was flirting with me.

One day when no one was looking she grabbed my ass, whispered nasty stuff to me, and stuck her tongue in my ear. But at night when I went to jerk off it was Barbara that occupied my mind. Late that summer, with a few days left before school started, I was at the shack when I heard noises. I looked out through a crack in the wall and spotted Barbara just as she was crossing the creek towards me.

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A few minutes later she knocked and came in. She rushed to me and kissed me, I rubbed her all over as I held her and then started removing her shirt. She stepped back. "No, I can't, they've just gone to the store and I saw you was here, I love you… I think about you all the time…please just hold me", she said.

I held her, she sobbed. I asked her why she was always crying when we met. She said, "cause I ain't never sure if it's the last time I'll see you". She cried harder as she went on, "they's talking bout moving from here, they'll be gone Friday, I'm gonna act sick and stay home, can you come to the house at dark Friday?, …don't come up if you see the truck… I love you, I got to go!" She went ambling back to her house as fast as her crippled body could go, and I was left horny, anxious, and sad.

I told my parents I would be camping Friday night, I packed my stuff and hid it all in my shack, then snuck close to Barbara's house and awaited her parents departure. As soon as I heard her daddy's old pickup drive off, I made my way to the porch and beat on her door. She opened the door and let me in. She locked doors and kept looking outside to be sure no one was around. I was all over her and she was trying to slow me down.

Two teenagers turned loose and on their own, we were giggling and kissing as I relentlessly tried to undress her. Once we were naked, I asked her if she would try sucking my dick. She agreed to try it. She sat on her bed while I stood over her and held my prick to her face. It was a lovely, disgusting sight.


She glared at the head of my dick with her bulging eye, and then, with saliva drooling from her lip, she opened her mouth wide, and put it over my cock until I felt it hit the back of her mouth. Then she closed her lips on it and sucked like she was sucking on a straw. The crooked teeth in her deformed mouth lightly scraped my sensitive young pole, as her inexperienced mouth learned to love her dream boy's hard flesh.

It was a heavenly sensation. I stood there perfectly still watching the fascinating sight as precum began oozing from my cock and into her deformed mouth. Tears welled up in her gruesome eyes as she stared into my sparse pubic hair and tried to move her head back and forth.

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Too soon she backed her head off of me whispering, "hard for me to breathe". Now that I had felt that, I wanted to try the other things that I had heard about. My older brother had told me about "69" and I tried to explain it to her. For some reason, she did not want to do that, so I moved on by convincing her that since she had got to taste me, she should at least let me kiss her pussy.

I had to just hold her, kiss her, and play with her tits for a while before she was turned on enough to spread her legs for me. When she did, I got between her legs and held her bony legs apart and started licking her pussy.


I didn't know what I was doing, I just licked her all over and jabbed my tongue in and out of her salty tasting gash. It took her a while before she got over the fear of my face in her crotch, but gradually, she began to moan and lift her bony hips up into my face and spread her legs wider. As her little stick-like legs moved apart, her cunt changed shape.

I watched in amazement as her hairy outer lips parted wide and exposed little flaps that outlined her tiny hole, and near the top of these flaps, a pink fleshy button arose. I licked all around her newly exposed flesh and when I licked over this button, Barbara nearly screamed.

I wasn't sure why she did that until by moving her hips, she pressed that part of her back to my lips and groaned loudly.

"This is so neat", I thought as I learned that sucking on this button gave me complete control over her. I saw my opportunity and I began shifting my body around on the bed as I kept her bony frame writhing in pleasure with my mouth.

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At last I was straddling her face and I could feel her breath on my balls. I felt her tiny hand grab my cock and then the warm, wet, sensation of her lips taking me in her mouth.

My hands went under her bony ass as I squeezed her sex into my face. I could feel my cock sliding deeper, and over her tongue. We were both lost in a new world, discovering new tastes and sensations that seemed so nasty yet so intimate. For me, the sweet, mild, urine flavor of her intimate parts, the view of her moist, tight, opening, and the thoughts of her bulging eye staring at my asshole had me nearing my release. Soon, Barbara too was rocking her tiny hips up and down rapidly, and breathing hard through her nose, I could feel her frantic breaths blow across my nuts and I sensed her orgasm.

She let out a gurgling moan as I moaned into her pussy while my young cock began spewing a weeks worth of cum into her deformed mouth. Her bony hips jumped off of the bed, pressing hard into my face.

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Our bodies thrashed and lunged into each other as we both breathlessly endured the exquisite pleasure of our first orally-induced orgasms. I could hardly move. I felt Barbara's head move to the side as she loudly coughed and swallowed a mouthful of cum.

We lay there in the near darkness of her bedroom and talked. Now that my urgent business of getting off was done, I was ready to listen to her. She whispered and sobbed.

Her family was leaving. I cried right along with her as she told me she could not live without me and how her young heart was breaking. Part of me was relieved that our relationship would end without me having to do it, yet more of me was devastated that I would be losing the source of my teenage thrills. I felt a sense of ownership, I had claimed the territory where no one else had dared to go. I had accepted her and given us both what we needed most. I was the only one who would ever deserve to feel her tight pussy hugging my cock, I was the one who tore my way through her virginity and she was mine!

We clung to each other with our tears mixing, our bodies responded to each other's closeness and I mounted her. There was no pain for her this time, her virgin pussy had held me twice now, she was in her soft bed, she was extremely wet, and she knew I loved her. At last she could relax and enjoy each moment of her dream boy and his rigid cock sliding into her love.

We knew that her pussy was made for my cock, and vice-versa. Still wonderfully tight, Barbara's pussy accepted my soft swollen head and urged it deeper inside her until we could get no closer.

With true love and emotion, I fucked into my little monster. I sucked on her hard little nipples that stuck out from her heaving chest. I stared into her gruesome eyes and felt love pouring out of her as she ground her little hips up and into me, giving me everything her body could offer.

We were now able to keep our young bodies fucking each other properly, each slowly drawing near climax then backing off to prolong our bliss. After 20 minutes or so of the most meaningful fucking either of us would ever be likely to do, we felt ourselves losing control.

She looked up at me and through panting breaths asked, "are you ready!?" As I nodded to her my balls were already churning. We watched the grimace on each other's faces as our love expressed itself through our organs. I felt like my dick expanded to twice it's size as it ejected all the seed it could muster into the grip of Barbara's tiny convulsing pussy.

Our bodies spasmed, jerked, and ground into each other relentlessly until, after squeezing every ounce of pleasure from our union, I collapsed onto her. Her parents were not likely to return until after midnight, we had another four or five hours together. Half of this time I spent either holding and consoling her, or giving her the lecture about how "you enjoyed life before we got together, and there is no reason you won't enjoy life afterwards".

The other half of the evening we spent fucking ourselves sore and silly until my orgasms were just mere exercises in pleasurable muscle contractions. At about 11:30, she opened her bedroom door and a window so that we could hear her daddy's truck coming down their gravel driveway, We knew we would have 2 or 3 minutes for me to escape once we heard them start down the long, steep driveway. I mounted her one last time. Our repeated orgasms had numbed our organs making it easy to prolong our coupling, our bodies spent, we were fucking on pure emotion.

It was more like a good-bye hug than a fuck. We took turns crying and whispering to each other as my sore pecker probed into her raw cunt.

For an hour and 15 minutes we fucked gingerly, never really coming close to cumming. Then we heard the gravel popping under her father's truck tires. Barbara burst into tears, spread herself wide, pulled me into her and begged me to prove my love to her one last time.

With my emotions running high, I achieved my climax in a matter of seconds. My groin painfully tensed up, trying in vain to find more semen to inject into her. My hideous, yet beautiful lover climaxed as well, heaving her sore saddle off of the mattress and into my groin.

Our organs knotted together painfully as her well fucked tube sucked at the meager offerings dripping out of me. "I'll always love you", was the last words I heard from her as I got up and threw on my clothes and stepped out her window onto a small back porch.

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I turned and we kissed each other until we heard the slam of truck doors. I told her I would never forget her, and then I slipped down the steep steps that led down to their back yard. It was the last I saw of Barbara for a very long time. 14 years passed, I had normal relationships like most young men, one or two serious but most not. Fucking Barbara's virgin pussy was a far distant memory, often remembered, but sometimes I wondered if it ever really happened.

I had moved a few hours from the town where I grew up.

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I had started boxing a few years back, I was pretty good. I would travel around to neighboring states fighting for money in amateur fight contests. It was late January, and I was competing in a contest held in a fairly large city several hours from my home. During a semi-final bout, while seated on a stool awaiting the bell to start the last round, I felt someone staring at me.

It's amazing how that works. Several thousand people were there and somehow I could feel a certain someone's eyes on me. I stood and began warming up as my eyes surveyed the crowd. There she was! There was no mistaking her unique appearance. She was seated in a wheel chair, with her head tilted to the side, her bulging eyes beaming up at me. The bell rang, another round, the fight ended, and as I walked back to the locker room to prepare for the championship fight, I glanced her way again just to be sure it was not my imagination.

It was Barbara, she was in poor shape, she was bent, frail, and tiny. Who knows what hell that girl had been through since that summer long ago?

I went through the last fight on autopilot, my mind blank. I won a decision. Crowd cheers, people gather. I am handed a trophy and a few hundred dollars. My mind numb from the fighting and spinning with thoughts of her. All I could think about was Barbara, my first lover, who was watching me now just as she had watched me from her window as a young teen. I descend the ringside steps on wobbly legs, take a left just behind the ringside seats, and my heart races as if I am still in the ring, I stumble down the wide aisle as an occasional fan slaps me on the back.

Now I am in front of her wheel chair and I stop, we look at each other. Moments pass as my mind sees her gazing at me in the shack from long ago. Her monstrous face now with that same amazed look that she had when she first beheld my naked body.

I step towards her, lean down, and kiss her deformed lips one last time, her hand raises to mine and I hold it for a second, then leave my cash winnings in her palm. I smile at her, turn, and walk away to a rising chorus of cheers as the onlookers vocally praise my act of charity towards the poor crippled woman.

No one there will ever know why the strange fighter from far away, would do such a thing, and then walk away with tears in his eyes.