Losing My Anal Virginity free porn video

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This is a true story of how I lost my anal virginity to a random stranger from Craigslist. Posted anonymously elsewhere.

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I cheated on an ex gf with some guy I found on Craigslist. I had always considered myself straight (despite the cross dressing and panty obsession), yet had been growing more curious as I got older.

A few years ago (in my early 20s), I was flat sitting for friends while they were away, and I was on the Craigslist casual encounters section (more out of interest than looking for anything, I was alone and bored). I saw an ad about a Netflix and maybe chill ad from a bi guy a similar age who sounded sane and fun, so ended up just messaging to see what happened. I didn’t expect a reply, let alone arranging a meet.

After meeting him outside at a neutral location, we walked back to the place I was looking after and headed into the into the room I was staying in. We started watching a show to relax. It got to a hot sex scene in the first episode and we both got hard. He took his cock out and started stroking it, it was the first cock I’d seen hard in person.

After a the scene was over, he suggested we find some porn to watch, so I let him choose, and he picked two twink guys fucking. He suggested I start wanking as well, so I very nervously got my dick out and started stroking it. I was immediately aware that I was bigger (a different ex had told me I was “huge” but I hadn’t believed her that I was particularly well endowed until then) but he was a decent size and I kept glancing at it. He noticed and said I could stroke him if I wanted. I tentatively wrapped my hand around his dick and began stroking him, a very weird sensation when you’ve only held your own before. After a little while I got into it, and he reached under my arm and started stroking me in return.

I noticed he’d started leaking a bit of precum, which is when he asked for a blowjob. I was so turned on at this point I couldn’t say no, no matter how nervous I was. I lowered my mouth to his dick and tried to suck him as well as I could. I was nervous but aroused at the thought of it. I licked up and down his shaft, kissing and licking his balls, running my tongue around the head, and taking it as deep in my mouth as I could (I was untrained, so it didn’t go deep).

I must have done ok though as he told me to get on all fours, he was going to fuck me. I did as I was told while he put a condom on. My phone rang and I saw it was my then gf, for some reason that only turned me on more.

I moaned like a slut as he fucked my virgin ass, all while watching a twink getting similar treatment in the porn video. He broke me in hard, slamming his cock into me so hard the headboard was whacking the wall. I didn’t care, it felt so good and the sound and feel of his balls slapping into mine as he made me his bitch for the evening drove me wild. When he finally pulled out, I was ashamed to have cheated, but horny af still and amazed that I’d gone through with so much.
That’s how I found out I liked a cock in my ass and that I definitely wasn’t completely straight. Since breaking up with my ex, I’ve been on a sexual awakening which I might detail later if you guys enjoyed hearing about this memorable evening.

Thanks for reading x

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20.10.2021
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January, 1984, Chicago, Illinois “OK, now that we’ve made love, talk to me more about Becky,” I said to Anala. “What I was trying to tell you was that denying your feelings, and refusing to address the issue with the girls closest to you, is not healthy. Is there anyone else that you are literally afraid of being with? And forget your mom for the moment.” “Nobody that I can think of, excluding my mom. I’m not sure that I’m afraid, but I’ll concede that for the sake of the...

A WellLived Life Book 9 AnalaChapter 36 Corrections

May, 1984, Chicago, Illinois Bethany and I said our goodbyes and I walked her out to her car. We kissed before she got into her car, and after she drove off, and I went back inside. My housemates were filtering out, along with my friends, and the house would soon be empty. I let Kara and Jackie know that I was going to pick up Anala. They disappeared together, and I headed out to my car to drive to Bridgeport. Other than a brief greeting, and a question about her final project, Anala and I...

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