I confess I let an older guy fuck me when I was 16.
When I was around 15, I started going on chat rooms and chatting with older guys. I was not and still do not consider myself gay, but when I get really horny I get in this depraved sense of mind. I'd get horny doing something I think is otherwise disgusting. Anyway, nothing got me hornier than knowing these older guys wanted to use my ass. I loved chatting with married guys because I knew they were paranoid about keeping it a secret like me. I had a lot of depraved convos with older guys about fucking my ass and making me their slutboi. I'd cum, always feel mega jackoff remorse, close the chat, and usually block them.
At some point I built up the courage to have phone sex with some guys. I would get older guys to give me their number and call it with *67 so they couldn't call me back. Pretty much whenever I was home alone I'd hit the chatrooms and find guys to phonefuck me. I was usually pretty shy on the phone, but I loved when a guy was really verbal and would call me names, faggot, etc, while we were moaning over the phone. We'd cum together moaning in extacy and hang up right after. Despite my post cum remorse, I would always go back. At times, when my family was asleep, I'd take my phone and a jizz napkin in the shed behind the house in the middle of the night to get off like this. I get both disgusted and horny thinking about moaning "fuck me harder daddy!" to some old guy states away, in middle of the night, in my filthy shed.
So now to the fucking: One day, I start chatting with an 50 something year old married guy and I don't quite exactly remember why, but we ended up jacking off together from time to time on messenger. He lived a few counties away from me, but in the same state. I don't think we ever phonefucked, but at one point he definitely convinced me to get a webcam, and I would cam for him. We had many horny conversations about him fucking me in front of his wife, etc. I'd always cum on cam for him and feel that remorse, I never showed him my face though.
We started having conversations about how we should meet and fuck, and it was always just jerkoff fodder. We were both to paranoid to actually do it. One weekend when the family was gone for the day we had a pretty long edging session early. We both were in an extremely horny state of mind I guess, because we decided to go for it. We stopped jerking off, our balls full with cum, to save for our depraved encounter. We worked out a plan were I would take a bus to a point where he would meet me and we'd walk to a motel nearby.
The moment I walked out of my house my heart was beating like crazy, but I felt hornier than I ever have. I'd never even taken the bus before, but my horniness made me so willing to do anything. When I go off the bus I saw the him wearing the clothes he described. He wasn't ugly, buy he was certainly a man in his fifties, a bit overweight and stocky. When I walked up to him, we were both very nervous and just said things like "are you ready for this" and "I cant wait." I started getting so horny as we walked, I started getting so horny though, and started thoughing his cock through his pants. Probably not the best idea since he was 50 something and I was young, but I was horny.
When we got in the motel room, my heart was pounding and my cock was throbbing. We took off our clothes and I lay on the bed naked. Keep in mind I was a complete virgin, only had a few fingers in my ass when I cammed for him, but was horny for cock. I had my first foreplay with this guy as we humped each other for a good 30 min. My cock was leaking at this point rubbing all over this hairy guy. We 69ed until I about burst and then gave him head while my cock softened a bit. I started pushing his cock on my tight asshole and we knew it was time.
He lubed up my ass with his fingers and slowly stretched me out a bit. It hurt and almost made me cum at the same time. He worked my ass with his fingers for a bit, until I told him to try to get inside me. He worked on a condom and dumped some more lube on his cock. I lay missionary while he started working his cock inside me. It was uncomfortable at first, but wasn't long before my cock was rock hard as his saggy balls slapped my ass. We started talking dirty. We didn't even know eachothers names. He moan "you like my cock boy!" and I responded, "fuck me daddy!"
He told me he loved me and I responded I love him too. I vividly remember this and making out while he fucked me. I confess my first kiss was this horny old man I met on messenger. He asked if he could take the condom off and I said fine. I didn't really understand how dumb that was at the time, but he was married I didn't think he had a std since he told me I was his first male fuck.
When he slid in me bareback, it felt so good. We kissed as he fucked me a few more minutes and then I told him I was gonna cum. A few strokes of my cock and I blew all over my chest and face with his cock still sliding in and out of me. Needless to say, I felt immediate disgust and discomfort. My cock got soft and I got quite but he just started pounding away harder. I'm not sure he fucked me harder because he saw I was uncomfortable and in pain and was trying to finish to get it over with for me or because the pain on my face made him hornier, but he pumped until he moaned "I'm gonna breed you boy!" Then stuck his tongue down my mouth while he pumped his seed deep inside me. He collapsed on top of me, his heart beating through me.
After a min or so he slid his beating semi out of my hole and just started cleaning himself up and getting dressed. I followed and there were few words after and we didn't look at eachother. We pretty much just dressed and I walked alone to the bus stop feeling dirty.
I blocked him when I got home and we never talked again.
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