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  • — Gay Stories —
    Transsexual Female / 22

    I always knew I was not well endowed as a young boy. My erect penis was about as big as my thumb. It was hard enough to find girls interested in a 5ft. 9in. 130lb guy who didn't play sports. I did date girls, and quite frankly got tired of being laughed at or pitied because of my penis size. I only succeeded in getting three girls either naked or who would let me pull down my pants with them. One just laughed and jacked me off "to see if it shoots", the other two didn't say anything but I could tell from their lack of comments and almost refusal to look at me they weren't happy. Soon the laughing girl spread word around the school and neighborhood and the other girls verified the story. I had no sexual outlet, and even jacking off was difficult for me.

    After a while another boy started hanging around me. He was a full on jock, muscular, tall, fit, and though I wasn't attracted to other guys he was a good looking kid. We hung out a bit and once in his car at the river he got me to take off my pants to go skinny dipping, and he said he heard I was small and it didn't matter, but he wanted to see. I guess I "modeled" for him and soon he took off his shorts and underwear and I saw an 8 incher hanging down between his legs. He opened the back door to his car and grabbed me, putting me face down on the backseat with my legs hanging over the outside, my feet on the ground. He fucked me. He didn't ask, didn't do anything to indicate that he was going to r**e me, but he started fucking me and didn't stop till he shot his load inside me.

    He pulled out, I was crying and he asked why. I told him why, that he r**ed me and how could he want to fuck another guy? He said I wasn't a guy with something that small, and he couldn't do that to girls, as they'd call the police, and he wanted to fuck someone and cum inside someone and that he'd now do that with me. I told him I didn't want him to fuck me in the first place much less do it some more. All he said was "you'll get used to it". After all the talking and crying about a half hour had elapsed and he started stroking his cock again. This time I knew, I just laid down on the backseat, further inside so anyone passing by couldn't see my r**e. He got on me and pumped away again, this time taking almost half an hour before he shot off inside me. "That felt good" he said, then threw me my clothes and told me to get in the front seat. I had to poop very badly and went behind a tree, he followed me and watched as I shit his cum and some poop out of me. I noticed some blood on the ground. He took me to a gas station bathroom, gave me some change and told me to go into the girls room and get a kotex out of the machine so I didn't bleed in my underwear. Like a fool I did it. He gave my ass a nice squeeze when I got out of his car at my house, pushing on that kotex.

    I got fucked a couple times a day by him, then started realizing that it was better to be in contact with someone sexually, to feel someones skin next to mine, to make someone feel good sexually, even if it wasn't a girl. I started letting boys and men fuck me. Most were me lying on my stomach for a quick pump, or bent over for an even quicker pump, I gave lots of blowjobs to completion to young teens up through old men. Not that I liked homosexual sex, I would have preferred being with girls, but I knew that wouldn't happen and I didn't want the embarrassment anymore. Sometimes the boys or especially older, married men would jack me or even blow me. I started finding guys who would make love to me, not just fuck me. For many I was lying on my back with my legs wrapped around them, face to face, kissing and hugging as I pleasured them. I was 19 and living on my own, fully realizing that I was openly gay. I found Martin. He was older, married, and gave me an expensive car, an apartment, and asked that I start living as a girl. I dressed completely for him, even started hormones, and on our outings to the islands, was quite passable in a tiny bikini. Martin and I eventually split, though I still let him fuck me occasionally.

    I date a few men, live totally as a trans woman and I still think what it would be like to have a normal size cock, if I'd have found my way to my femme side or not.

    #40366 — Comments (0) — Jun 1, 2018 at 10:53 AM — That's Juicy! (6) Remove This.

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