My anal virginity story

First, a little bit about me. This story happened when I was 21. I was living in Saudi Arabia, which actually has a thriving underground LGBT community. I’m a bi vers guy so making a decision sexually was never much hassle for me. I was kinda scrawny at the time, 5’11 with a pornstache and a mop top. An anal virgin, I had sexual encounters before this but they didn’t extend past bjs.

I downloaded tinder out of pure boredom and horniness. I quickly got familiar with how it worked and its greedy capitalistic structure. Therefore, I only swiped right on people who I deemed were more “in my league”. I’d never waste a right swipe on a 8/9 when I was a 6 on a good day.

That is until I came across this one profile. He surpassed my original red-zone of profiles and was easily a personal 10. Tall-ish (6’1), well trimmed beard, muscles that actually looked natural. Cute face to wrap it all up. I decided to bite the bullet and swipe right for fun. “It’s one wasted swipe, what’s the harm?”. I then see “What a Match!” pop up on my screen.

He made the first move and messaged me first within like 5 minutes of the match. We went to Snapchat and he invited me over to his place “to hang out” that night. I agreed but he mentioned one last thing, “I’m a top btw”. Fine by me, at least I know there’s gonna be some action 😈.

I was quivering and thirsty the bus ride there. I always wanted to have sex but it never played out like I wanted it to. Walking up to his apartment door, I could feel my heart in my throat. He looked just as nice irl as he did in his pictures, albeit some aspect ratio differences from the human eye that a phone camera can’t capture. He was wearing a soccer jersey, I think on purpose to accentuate his fit body.

He led me to his bedroom but before stepping in, he informed me that no outdoor clothes were allowed in. We stripped and he wasted no pinning me against the threshold of the door and kissing me. Soft kisses, but passionate. I felt his dick rock up against me and I stroked it for him. It was a nice 5-6 inches and not too thick. I was about about as big as him. He didn’t have much hair on his body save for some on his arm and chest, and a nicely groomed pubic area.

He sucked me in his bed, and he sucked well for a top. The bj lasted longer than I expected and I thought that he wasn’t gonna fuck me in the first place and leave it to soft play. I told him to take a break cause I was close to cumming and wanted to suck him off too. He didn’t heed my request and continued going until I effectively shot cannons into his mouth. “So much for a top” I thought. He didn’t swallow, instead coming up to kiss me with my cum in his mouth. Porn had me thinking it would feel better than it actually did.

I went to wash my face after that and expected to find him getting dressed or something. Instead I find his bedroom empty and his voice telling me to come to the living room. There I see him on the towel covered couch with a box of condoms and lube on the table. I had never had such quick turn around for my horniness in my life.

We made out, the taste of my cum still in his mouth. He told me to lay on my stomach on my elbows and knees. I’ve gotten eaten out and fingered before but he seemed to be a pro at it. His beard made it a bit ticklish though I can’t lie. I didn’t like the fingering all that much cause he seemed to just jam it in there without making much effort yo massage the prostate. At least I bideted my bowels beforehand.

The feeling of the cold lube mixed with his warm cock was otherworldly at first. As I mentioned earlier, I was an anal virgin. I didn’t quite know how painful this was gonna get, the deodorant I used to “loosen up” my hole was nowhere near as painful as his dick. I instinctively pushed his body back and yelped. I calmed down and said I was ready to start again. This time he put his body weight on mine and went in much slower. I yelped again and be put his hand on my mouth. This was problematic in hindsight but still felt so hot as it was happening.

As I got used to the pain, he stayed thrusting me softly. And I moaned and grunted in pleasure with each push. I was rock hard again and could see my precum leaking on to his couch. For reference to gague my horniness, I almost never precum. We switched positions every now and then. But the only one i remember is him managing to stand on the couch with his legs and fuck me with my ass in the air. That one particularly makes me brick everytime I think about it.

We fucked for a good 20 minutes before I asked him if he was close. He sighed and said in a confessional tone that he probably wasn’t even close. I didn’t know what to say and just watched him continue to fuck me. Then he stopped and came to my face as asked if he could take his condom off.

I said no at first but he was insistent. He said that he hadn’t been with other guys before (as if that’ll change anything) and I very stupidly let him fuck me raw. I didn’t feel anything different but it apparently made a world of difference for him.

He didn’t last longer than 5 minutes before I felt him quickly pull out and tell me to turn around and jerk myself off. I quite literally came in 15 seconds. It appears that the sight of me cumming set him off and he came all over my chest, with a bit reaching my mouth and face.

After washing up and getting changed, he told me to get back on the bed with him “to chat” but we ended up just making out for a while. I left his place with a hickey, an STD scare (which came out negative 🙏), fucked up hair, and no virginity.

No regrets (actually quite a few).