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.