My greatest regret is not being a slut in my youth (Gay)

I was such a horny boy when I was young. When I was alone in my room the dirty thoughts that crossed my teenage mind were so intense that my masturbation took new forms. I'd crawl around on all fours with a hairbrush handle up my ass and my skinny prick leaking on the blue carpet. I'd tie my ankles to a desk chair, put clamps on my nipples, and tape a wadded up sock in my mouth to simulate captivity. I'd put a pillow case on my head and choke myself with a belt until I was dizzy. I'd shoot my cum in my own mouth or slurp it off my hands or smear it on my face while imagining being surrounded my men jerking their cocks.

In the chat rooms I'd pretend to be or roleplay as anything that would allow me to feed my dirty fantasies. I created an entire female persona so I could consistently fool straight men into britalizing me online. In the gay chat rooms I'd be a neighbor boy, a homeless boy, a prostitute, or even a man's nephew or son in roleplay if it helped me to vividly imagine hard, fat cocks using me.

I even joined a gay meet-up website for doms and subs, pets and masters, etc. I'd post pictures in my profile of my boyish, naked body with a jockstrap crotch covering my face to protect my identity. I'd revel in the attention of the top men who wanted to use my ass. The more depraved their profiles, the more bondage gear they owned, the more testimonials from satisfied total bottoms like myself they had, the harder my prick throbbed and the more thickly the drool flowed from my mouth.

The closest I came was a man in Pittsburgh who wanted me for a long weekend as his pet dog. He called me "Pup" and promised nice, soft mitts for my hands and feet, a heavy leather dog mask with a thick ball gag for my mouth, a tail plug to anchor deep in my ass, and a cage for my little prick. God, how bad I wanted him to own my stupid teenage ass, to show me what it was like to beg to kiss his feet and slurp his cum from a dog bowl. He was going to call my cell and we would get to know each other a bit more. I was sitting there bare ass naked with my phone in my hand...but when he called me and said "Hello" I freaked out and hung up and blocked his number. I apologized via e-mail and he forgave me and said he would be around if I changed my mind.

Its more than a decade later now. I just turned 30 and my boyish body is quite a bit hairier and thicker. I still masturbate to the same fantasies of submission but I could have had more than fantasies when I was young and fresh. Who would want to own my ass now compared to the horny boy I was? I'll always regret not being a cute young boy whore when I had the chance.


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  • What a hot story. I used to do similar stuff too . I was 14 or so and had a pair of nunchucks on my wall, when nobody was home , i'd stick one in my ass which hurt at first,then i did it often to get used to it, i'd lay face down on my bed and pretend i was getting my ass plowed and move it in and out, when i was getting close, I'd flip over on my back on the floor,put my legs over my head and i could just barely get the tip of my cock in my mouth and id jerk and cum in my mouth.. it was awesome . Mostly id just jerkoff and cum in my own mouth daily,always trying to get more and more in my mouth,I made it as far as the entire head.

  • I was quite the cute little boy slut starting when I was in grade school and caught the eye of a teenage boy. There I was meeting with a 15 year old boy when I was only 9 in a grove of trees shorts around one ankle and tighty-whitie underpants yanked down in the back. His slender forever hard boy cock never seemed to go soft when my tight pert little ass was facing up. My wide eyed innocent fresh faced looks, short frayed cut-off jeans sporting white cotton underpants seemed to beckon any horny teenage boy and an occasional man friend of theirs.
    When I turned eleven I got my first speedo and was I cute! My tiny boyish package was attractive to all those with "small eyes." I got banged by a group of interracial boys down on the lakefront. One of the cute half and half black and Puerto Rican boys seduced me the week before and bragged to his friends about the hot white kid that he was fucking that had a dynamite ass. I spent most of the summer putting out for him and his gang of friends who also occasionally pimped me out to a visiting business men from a nearby hotel.

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