He was also seriously hung (8.5 easily), so it was quite an introduction to anal sex. At the next practice, the coach acted like nothing happened and that I was no one special. This was in the early 80's at a large upper-middle-class suburban high school.18 or 19, in college. I was dating an older guy (among others) who was well hung and was patiently warming me up to anal without pressuring me.A graduate student was the culprit; he was about 5, I think. Then one night I went out with someone else, got a little drunk and ended up bottoming for him. Both of us ended up with shit on our dicks, pubes and ass.Before that I was just doing oral stuff here and there with the closet cases in my high school. He didn't much like it either but we did it to shake things up every and then, but it always ended with us flipping back to what we like best.15.I lost my ass cherry to Doug during a sleepover at his house. It had been like that whether I liked it or not.19.We hit it off and I stayed when everyone else left.Later on in bed I turned over and presented my hole to him.My favorite position was sitting on it, riding up and down. And part of the reason was that I had no idea how the entire ass/clean, ass/shit thing went. A few weeks after meeting him, I practically threw myself at him after a game of (dorky, I know) drunken Truth or Dare. The cream didn't work for me, but kept him fucking me all night to the tunes of Bette Midler, who I knew nothing about. He put on a condom and entered me slowly, patiently and I loved it. Usually I just stood in the corner watching the people and the videos and left before closing time. I picked up a stranger at a bar (I had fake ID) and we went to his car. I just wanted to finally do it, and I bottomed a lot for a few years after that. It definitely hurt but didn't last long because I was so tight. I'm not with him anymore but I'll always remember that first time.
Several boyfriends later, I discovered the pleasures of bottoming. I knew then that I would be fucked for the rest of my life and so far I do. And I went home with this muscular older guy - in his early 40's, I think. I think it was because of him and of course, that experience. In my twenties it got to the stage where I never even bothered to turn round in an orgy to see who was thrusting in there. No talk, no gay shit, get on your belly, spread your cheeks he always said and yes he greased my asshole.13. When I was 19 I ran into him when I was home from college. In the small town I lived in, AIDS was a rumour from the US, so we didn't use condoms and it did feel different. FYI, watching Hello Dolly in the family den when you're 15 is way gayer than being anally penetrated. So it was the late 70's, and now I'm thinking that being 15 and getting fucked by a 13 yo now, woudl be absolutely apalling. lol And yes I still love to bottom, and no haven't even seen him for probably 20-25 years, and he still hadn't lost any of that farm boy sexiness. Before I knew it, I was on my knees and his dick was in me.
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A quiet guy, to be sure -- but hung like Man O'War. He had a short little dick and no finesse, so the experience was all jibbity-jabbity, jibbity-jabbity. The older guy I was seeing later showed me that bottoming could be a pleasure, but I've never really taken to it, and rarely do it.19. I was "closeted" (asexual virgin) and knew of only 2 gay guys on campus. Only later did I learn why he had a single dorm room--mental issues including uncontrollable rage. The next time we did it we washed up first and used condoms I stole from my dad.
Hurt like hell (he liked it lube-less, and I was so green I didn't realize that lube would have been a valid request -- I wanted to pleaaaase him), but got to where it felt incredible. ", my friend was plowing me up against the sink.36. One was my roommate and another was a guy that my roommate met through the campus's very, very small LGBT support group. Blazing hot and country bumpkin-style sweet and friendly. Which turned out to also be wild and unforgettable, but not in a good way.14. I was 19 in my date's dorm room with his room mate on the other side, separated by a few tall bookshelves, which is why I didn't scream from the initial pain. The guy lubed me up with some sort of strawberry flavored de-sensitizing cream and probably some coke (he'd been rimming me, which sort of shocked me with disgust but felt pretty good). we have a long talk about safe sex and all but the next thing I know he's got me TOTALLY relaxed and manages to open me up. I was out barhopping in DC, and ended up at the Frat House.
I came out at 30 and let my second boyfriend fuck me. It was pleasurable, but guys I dated wouldn't let me fuck them because they thought my dick was too big. Katie bar the door, he still loves it.18 - with one of my fellow freshmen (who then became my fraternity brother). I had been introduced to him at dinner in the dinning hall after complaining to a friend I'd known since grade school that I was gay and bored, so he said "hey! After a while it felt OK, but mostly I liked the intimacy of a warm body on me. His was a postal worker, and I could tell he had a great body. I did not have lube/rubbers, but did locate some butter in my boss's fridge (very Last Tango in Paris). It was Jim, the HS jock, dream boat, minister's son. The next night I took him to mans country in Chicago. I was on a vacation with his family on a cruiseship. I was 15 and I was camping out with a friend from school.