He definitely wasn’t a virgin, in his mouth or his backside, but he convinced me to try m2m sex, I liked it
I was 32, married had a variety of sex partners in my past all female. I never found myself attracted to other guys, I loved women, their bodies, their tits, pussy and loved their butts as often as one would let me. My wife let me have all three holes, she was great, inventive and pliable to anything I asked as well. Then I went to pick up a gay friend from work and saw John. John was totally undressed as my friend was getting dressed. He moved like a dancer or model, not walking but gliding around. His body was hairless except for an inch wide landing strip above his cock and the brown, longish hair on his head which hung down to his shoulders. His lips were pink without any makeup, his body thin indeed feminine, his face, like a beautiful woman. “Pay no attention to John, he likes to be naked whenever he can, especially in front of someone who is new to him” said my friend. Then dressed he said to go and we left. I saw John on three other occasions with my friend, and was left alone with him for over an hour once. It was then that he was wearing a silk robe, as soon as my friend left John turned on shemale porn took off the robe and sat right next to me on the couch. “I like you, you’re quiet, nice” he said. I said thanks and asked him about his age. He told me he was 14, I knew this already as my friend briefed me on his history.
John was fucked by an uncle starting at 11. The uncle died and his drunken mom let him wander around, have people over, come and go as he pleased. She pretty much did the same. Mostly bringing men over to get fucked while drunk. John would go out and find older men to fuck him or him blow them too. Watching the porn, the shot was what looked like a very young crossdresser taking his first cock in his ass to a bit of pain. “You like what you see?” he asked. “I don’t know, looks like he’s in some pain” I said. He responded that it only lasted a few minutes, then got better, and after getting fucked 5 or 6 times you get used to it. He said he really liked it, liked it a lot. He loved sperm and sucking sperm out of older mens cocks, especially big cocks, and especially married mens big cocks. He asked if he could see mine, since he was so exposed. I didn’t want to. He moved up and sat on my lap, I could smell womens perfume on him. “It’s my moms” he said. “Do you go naked with your mom at home too?” I asked. He did much of the time, even taking on some of her lovers after they were done with her and she passed out. He told me the story of fucking at 11 and by 12 had blown 7 guys and fucked by two, his uncle and one of his uncles friends.
Moving his perfect little ass on my crotch I was getting hard. He wanted me to fuck him and I told him that wouldn’t happen in someone elses place, we had to find another place, then he offered to blow me there. I still wouldn’t. He was begging me, he said he really could like me and he knew he could satisfy me just give him a chance. He asked if I’d ever done anything with another guy and I said I had not especially no one his young age. He bluntly asked me if I thought he was attractive, standing up and exhibiting his body for me. I told him the truth, I found him attractive the only guy I’ve ever found that way. In addition I was hard and showed him the tent in my pants. He wanted it and I refused. Then he stood in front of me and started jacking his cock, he took my hand and pushed two of my fingers into his ass. “Do it , Do it while I take care of myself”. I finger fucked him and he jacked off. When he was ready he moved to my face telling me it was about to happen. I have no idea what was going on in my mind but I opened my mouth and let him stick it in. I sucked on him the last few minutes and then took all his 14 year old cum in my mouth. I swallowed immediately. He leaned in and kissed me on my lips, his beautiful face was too much. I stood up and agreed to meet him at a motel the next day, and told him NOT to fuck or suck anyone else till then. He said he had to suck or let my friend fuck him when he returned but that would be all.
The next day, he showed up, stripped immediately and then told me to strip. Both of us naked, we had the afternoon to ourselves. He sucked me off, I sucked him again, and then he laid down on him stomach parting his perfect buns for my entrance. His hole though well fucked, looked normal, not extended or anything. It felt like heaven. It was so tight, yet obvious that I could fuck as hard as i wanted. He was fucking back into me as I was pushing in and out of him. I blasted a full load deep inside him. That afternoon he sucked me twice, I fucked him twice and I sucked him that one time. I dropped him off at his house and the next evening went by to pick him up. He told me that I could stay there with him. His mom was being fucked by two guys and we went into his room and on his double bed, I fucked him missionary. When I pulled out he immediately took my cock in his mouth to clean me off. The two other men left, one glancing into his room to see him cleaning my cock. He got up and took me to the hallway, we stopped at his moms room. She was laid out on her bed naked, cum oozing out of her hairy pussy. “You can fuck her if you want, I don’t mind” He said. “If you don’t want her used pussy, you can fuck her ass, see if I’m better” he added. I couldn’t believe it but I was getting hard again. He knelt down and sucked me hard and pulled me into her room. He rolled her over, put some lotion on her ass, and told me to do it. I got on top of her and buttfucked his mom. I came after about 30 minutes all she did was mumble during it. Then he sucked me clean again, and I got dressed and left. Before leaving I kissed him, like I do my wife and told him, she’s good, she’s hot but he’s better. ‘Keep coming by and you can fuck us both, 5 holes, no waiting” and I left.
It’s been a month now, I’ve fucked him over 20 times, I’ve blown him 5 times and I’ve fucked him mom in her pussy and her ass and left my cum in her mouth too. He likes seeing her used, especially by men who have had him first. Then this weekend I did something else I’d never done. He was hard as I buttfucked him mom, and I took him on top of me, and lying next to his mom on her bed, I let him fuck me in my ass, a virgin ass. He was slow, gentle, and used a ton of lube. I know I shouldn’t cheat, but he is so feminine, he even wears his moms undies for me a lot of the time, and I fuck him mom. It’s indecent, it nasty, its the dirtiest thing I’ve ever done, and now I let a 14 year old fuck me too.
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