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Jeff_got_sodomised

I first bottomed when I was 18 years old. It was my idea to bottom for the first time because he didn't know I was a virgin. When chatting online he said that he didn't like virgins and then belatedly asked whether I was one. The guys was hot and I was a desperate teen, so I lied. When we actually met up he was quite rough. Not going to lie, it hurt, but looking back it was a super hot experience.


FillUpMyFatAss

Okay, I know it's old and tired, but your username checks out!


TheBlissOfFullness

Bottomed at 12 or 13, first time, and we both wanted it


Brian_Kinney

A similar post happened [less than 24 hours ago](https://www.reddit.com/r/TopsAndBottoms/comments/13m4urd/when_did_you_start/) (but it was deleted). You might be interested in the answers.


AkolouthosSpurius

15 It was with a guy 2 years my senior from my school. I was fully out so everybody knew I was gay anyways, and I had my teenage glow-up in the summer before that year so I guess I suddenly appeared on people’s radar ☠️ He pursued me after school when I stayed for extracurriculars when he could catch me alone. It escalated from just talking to touching to kissing to full on hands everywhere making out with clothes on. Eventually he invited me back to his place. I knew where it was going, and I wanted it to go there so I prepared for it and all. But he initiated it. So I guess it was both of our idea?


[deleted]

Never, but I live in hope.


eatingthesandhere91

26 and it was his idea to top, after three dates in a month. It just kind of happened. After that though, we quickly drifted mostly because communication simply wasn’t there. I haven’t topped yet though.


gptop

22. Drink, high, and horny. Answered an a post on CL. Was supposed to be a blow and go but I ended up fucking his tight ass


TypicalViking

Topped at 17 in the school locker room by a (first timer?) power bottom. I think it was both of our first times because it went really awkward. I sat on one of those long locker room benches while he reminded me the if the door closes you can get out but you need a key to get back in, and proceeded to remove the door stop he’d left there earlier. We got undressed and he had me lie back on the bench so he could suck me. I think he scraped once or twice. Then he got up and tried to straight up sit on my dick with spit as lube. The problem was he didn’t quite get it very wet, and I hadn’t gotten into eating ass yet. I was hard as hell and was about 90% sure my dick was going to bend in half. I asked him if he had any lube and I think he said he had a condom in his bag and he went to retrieve that. In the mean time I decided to go piss. This was an unfortunate decision which I realized the the moment the door “clicked” closed, locking us out. When he came back I was embarrassed and he seemed bugged but, we legit ended up in the handicap stall. I’m not sure if he had preloosened himself or something because he made no signs that he was in pain (I’m long enough and acceptably girthy where usually can be a bit uncomfortable which is why I’ve taken to eating ass, but I digress). Unfortunately I did not last very long, even with the condom on it was just so exciting and I came in a matter of seconds. I remember telling him “maybe it feels better from this side” and he’s like “I don’t know….” Hahaha. Back then I wasn’t really out and so we didn’t really do anything more again. We were watching porn together at school and got caught and that pretty much ended his attempts to woo me.


OatmealThick97

The year was 2017 I was doing my daily routine of walking my dog and noticed a new cold stones ice cream shop! I tied my dog to a stop sign and went in to order a mint chocolate chip when I came across the cutest man! He was 6'8 bronze skinned and was packing! One thing led to another and I was getting my back blown out behind the cold stones near a dumpster. When I was finally able to limp my way back to the front I realized my dog was gone! He managed to run across the road, But I caught him!! I never got my mint chocolate chip 😫 3/10


Sloclone100

I had fooled around with a friend from school but my mom's boyfriend knew I was bi-curious and after a camping trip, took me home and fucked me. I loved it. Then I suckedhis cock and when he came it shot straight up in the air like a fountain. I didn't even get to taste it. This went on for 5 years. It really made me a great bottom.


[deleted]

[удалено]


Brian_Kinney

> My fist love Fisting on your first time? Impressive! 🤣


Responsible-Way5056

I bottomed and, at the same time, had sex for the first time at this age of 19 years-old in the night, after midnight, on Monday 20, 2023. In the lowest subterranean floor of a modern apartment building in a maybe late-1940s middle class neighborhood in Lima, Peru. The top who fucked me was a thin and bit kinda athletic person in his 20s (not conventionally attractive) who was working in that apartment building. He literally fucked me in his working hours. Making out with him and sucking his dick was not so bad at all (except when he started to fuck my mouth for a longer time without thinking that I was choking). The disappointing part comes when he fucked my ass (he fucked me in doggy position). The first time he penetrated me, it hurt me a lot: He wasn't being considerate and smooth enough. Then I told him I was virgin, that it was the first time and that I was feeling pain. So he put his dick out of my ass, started to penetrate me again more smoothly, I felt a bit less of pain and then he started to fuck me. He was enjoying my ass a lot and even he licked my back once, but I didn't enjoy a fuck about the experience. However, I didn't repudiate the experience either. I was just fucking bored just feeling a disappointing piece of meat rubbing in my anus. Nothing more. I didn't moaned a fuck either. What a disappointing experience that lasted a few minutes. I don't even feel sorry for him, because after we fucked, I asked him how did it feel for him and I even told him that I didn't feel pleasure, but he was more concerned about quietly guiding me to the exit. After going out of the building, while I was going to home and even after I got to the place where I'm living in (here in Lima, Peru), I felt dirty and ripped off. Even the second and the last time I was fucked (May 13, 2023, afternoon, Lima's downtown) wasn't pleasurable either. At least the 46 years-old thin (a thin man... again) top who fucked me was more gentle and comprehensive. We hooked up while the mother of the top who fucked me was sick and lying on her bed. At the beginning he didn't want to fuck me because his sick mom came to his house so his son can take care of her and the liar didn't tell me that on time. However, I wanted to piss, so I asked the guy if he could let me to use his bathroom and he let me with the condition that I should walk and talk quietly. While I was pissing, he was behind me watching me piss. So, after pissing, I felt horned up because I just wanted to, at least, try sex again hoping that this time could be pleasurable. And then he horned up too... Some minutes later, after foreplay, he was fucking me, but it wasn't really pleasurable either, I felt pain again the first time he penetrated me and he came in less than a minute. So fucking frustrating. At least, we said goodbye to each other in a mannered way and not like that disappointing and not-so-polite doorman from the first time. If you wanna know more details, check this link out where I explain more about the story of my sexual history. I removed some details of the story due to very personal reasons, but I promise it will be interesting: https://www.reddit.com/r/AskGayMen/comments/13kvmbj/why_didnt_i_feel_pleasure_while_i_was_bottoming/?utm_source=share&utm_medium=android_app&utm_name=androidcss&utm_term=1&utm_content=share_button Thank you for reading. Have a very good afternoon everybody. Greetings from Lima, Peru.


Jamo3306

I had some intimate contact with other boys from 13 forward. I didn't complete anything recognizable as sex until I was 17-18 and already essentially on my own. I don't think, I bottomed until I was 20. A VERY patient, somewhat older man (26 or so) who I remember as Rene. I flaked out on him and always felt bad I didn't give the relationship a chance.


ATLguyATL

My first time bottoming was in college. I was probably 19. He was an older guy, and it was one time hook up in a bathroom. We met outdoors on a bench on campus and just started talking. It was his idea to go to the bathroom (it was a private one in an older classroom building with a door you could lock; he clearly had done this before). It was his idea to top me. I thought we were going to trade BJs (which we did before the fucking came up). It hurt a lot. Not a good first experience but not truly awful either. I'm glad it didn't sour me totally. Funny, I can't remember the first time I topped someone. It was likely a couple of years later, the first year after college. I didn't do anymore anal in college. I definitely remember topping and bottoming that year. I just can't remember the actual first time anymore. Weird. I remember that year -- first year out of college -- topping AND bottoming at the same time in a threeway. That was hot and weird. I loved it but was only able to accomplish that a couple of more times as the guy in the middle taking and giving dick. I love the idea but found I'm much better at one or the other. I was about 15 for my first oral experiences -- first giving, then receiving with a different guy a year later.


dorkyfoxx926

* i lives in religious-homophobic country so ive been closeted and im too scared to find a boyfriend and had been virgin till i 30 years old * i guess after graduate and have a job, lives alone, i feel free to do what i want, without suspicion of my relatives * i met this guy who 5 years younger than me through gay-mobile game discord server, we got close pretty fast since we lives in same country and he closeted too. then we start to flirt each other, send dirty words, send body pics * we finally have courage to meet irl, it was him that asked me if we want to meet at hotel. i was so innocent that i didnt know it meant he asked to have sex with me at the hotel. turn out he's virgin too, he asked if i want to try to be bottom or top. from seeing bunch of gayporn i always got turned on imagining myself got fucked. turn out it wasnt that easy with the preparation. it was hurt at first but it got really good after my ass loosedned up. we're both got tired pretty fast but it was really worth it


CuteGuyInCali

I was about 24 or 25. AMAZING! I had experience anally masturbating so I knew I could take it. Cock is a lot softer and hards (at the sametime) than anything else I inserted during my "training phase" and to top it off the man the cock was attached to was such an amazing experience. Sensory overload!


H_the_odd_one

2017 November. Age 50. After two false starts with CL ads I had been I Kik for almost a year, I invited a local guy over and I sucked my first dick. I was nervous as hell but all that went away the second we were naked. He lasted all of 60 seconds 😂 after that I went on a boy crazy binge. Bottoming then topping.


LowWorldliness2604

Kik works?


[deleted]

First time bottoming 14. I tried topping at 15 but it didn't work. My dick was/is too small and I couldn't get hard anyway


crm314_closet

Bottomed at 19. We both grew up in a very conservative town, which meant we had to wait till midnight and do it in the dark. We met via Craigslist. I was a virgin, and somehow knew that I might be able to find a likeminded person using the internet. It didn’t take long for me to find him. I drove halfway across town to his house. It was a large house and his family slept upstairs, so as long as we didn’t turn the lights on and tried to be quiet, we could probably get away with it. I shook all over as I drove to his house. I’d never met the guy before but as soon as he opened the door and put his hand on the small of my back, I calmed down. He was only a year older than me, but seemed far more composed, or experienced. I had said I’d bottom online, but he didn’t rush me to that. Instead we must of spend an hour kissing, taking our clothes off, and slowly grinding our bodies together on his couch. I’d never had sex before so I had no idea what to expect. It was magical the way my body came alive as he lay atop me on his couch. Our cocks were both hard, grinding against each others bushes. That’s when he got off the couch and started sucking my cock. I had to cover my mouth so as not to make noise. I didn’t let him finish me before I got down on the floor and started sucking him off. I had never had sex before, but I knew I wanted him to cum in my mouth. He did, and I swallowed every drop. He sucked me to completion, which might have been a mistake, since my body was convulsing when he started putting his cock into me. It hurt! I didn’t realize it would hurt so bad. But he was slow and listened to me when I gasped in pain. I didn’t want him to stop though, so after letting the pain subside I told him to continue. It still hurt but after his shaft was in me it started to change. It wouldn’t stop hurting, but with the hurt came a deep satisfaction. He didn’t last too long before coming again. That was a blessing since it still hurt to have him inside me. I remember him twitching and spasming, his lips were shaking as he kissed me. He moaned a final time into my mouth. I suddenly became rock hard and somewhat swooned. For my first time, I had no idea just how amazing it would feel to have such a passionate connection, and how intoxicating it would be to have someone come to completion with me. He felt my hard cock and asked if I wanted to try entering him. Yes yes yes - I thought. He rolled over, but I barely made it past his sphincter before I came again. His cheeks were so warm and taught. His hole wasn’t stretched out either so it was insanely tight. I slumped against his massive back as I rode my first orgasm inside of someone. He was so so warm. I pulled out, and we cleaned up. We both didn’t know anything about preparing for gay sex, but we at least had condoms and he had a few towels. We were silent, we didn’t want to wake his family up. It was dark, we didn’t want anyone to notice a light on. But we cleaned ourselves, dressed, and found each other in the dark. We kissed again and I left, my body aching with pain and unbelievable ecstasy. We would meet 5 or 6 more times before his parent discovered us. He was sent away to live with family elsewhere. My own family never found out, but I never sought anyone else until I eventually moved away. I wish I could find him. It was my idea and I offered to bottom, but he wanted all of me… and I want all of him.