it hurt like hell, but I remember thinking over and over again "Holy shit! I'm finally actually doing IT!"
A huge, black stud took me into a video booth in an arcade and I went down on him. Nice, thick. Half way through he lifted me up spun me around and plunged it full bore into me. It hurt, i started passing out and screamed "GET IT OUT OF ME".
Not exactly a bookstore fantasy.
He withdrew, and exited quickly.
I sat on the curb, in front of the Glory Hole Bar and it took me two hours to recover from the ass-ault.
Two years later, when I was 17, I met a man who said he knew how to do it right.
He was correct.
I used my allowance money to see the original "Doctor Dolittle".
Hated it. Still do. Hurt like a bastard!
Didn't hurt. Felt great. He went nice and slow, very passionate. He's got a small dick so that maybe helped.
I had already been playing with my vibrator dildo so I was good to go.
The first guy that fucked me was so small that I really didn't feel anything, and I thought, oh well that was ok. The next guy however really showed me that it just isn't my thing.
First guy was this hot black guy I met at the gym. I was 17, he was probably 40. Had a huge cock. We went to some motel and he asked me what I wanted. I was shy and young and just sort of hemmed and hawed. Then he said, "you tell me what you want, boy" in this nasty growl. I said for him to fuck me.
We tried for like an hour, but I just couldn't take him. Didn't try anal again for years.
I was 13. It was my older brother before he went off to college. He was really gentle with me. We fucked all
of that summer. He ended marrying three times, lives in Texas now with some girl. We don't really talk much.
18, the night I graduated from high school. Met up with him at an adult book store. I was drunk. It was awful and hurt like hell.
The first time I got fucked was my first sexual experience of any kind. I got picked up by a hot guy at the campus fraternity bar when I was 20. He took me to a hotel, where we split the $18 room. We were both clueless, as he didn't have much more experience than I did. We didn't have any lube, nor did I even know what lube was. So after I went down on him, he just used my spit and his precum to shove himself into me. Hurt like hell but got better after a minute. I didn't even jack off - just let him fuck away. He came after a bit. I never got off, and it hurt, but it was still...interesting... and i knew I'd eventually grow to love it. And over 25 years later, I still do.
His cock wasn't huge, wasn't small - about 6 u.s. inches I think - and I had lots of lube and we played with toys first, and I had done that myself. He was a good top and let me run that part.
Wasn't hard to figure out after an equal size toy I'd be open enough for him but tight enough for us both to enjoy it. The toys were pressure, not real pain, unless you're hypersensitive to that kind of thing.
He was a great kisser, tasted great, smoked pot and was funny as hell. He had to leave school for the pot use - real loss.
Went home from a bar with a guy. I later discovered he was a total bottom, but it was my first time with a guy so he rose to the occasion. He wasn't very big, so it didn't hurt as much as it could have. And he didn't pump- he just went in and stayed there for a while til he came into the condom. Kind of a letdown (for both of us?). I bled a little.
I had an Enya cassette playing in the background. True story.
Bleeding? Something must've gone very wrong.
The weekend before finals when I was 17 and a senior. He was a 27-year old hot Italian guy. Took his time, was gentle and slow to begin with and eventually picked up speed. It was amazing. We started at 11 in the morning, had sex all day, went to the kitchen and made some dinner, then back in the sack for more fucking till 11 that night.
Clean your pussy, Cheryl! Maybe you'll get lucky.
I was 26 years old. Until that time I'd been exclusively top.
Until I met this one guy. Cute guy, small frame, mixed Mexican and European. And one of the biggest cocks I've ever seen.
He figured out how to make me WANT to get fucked. We took turns btw, he'd fuck me, I'd fuck him. It was fun.
I lost my cherry to my best friend when I was 14. We flip-flopped and did each other. It wasn't painful, but we missed the "clean your ass" instructions. We didn't use condoms and it was a real mess. Luckily we were able to shower after.
R20 Girl, didn't you know? Lube costs as much as a diamond encrusted Jaguar!
Wow, some of you guys are really fragile. I took to getting fucked like a fish to water. I was 15 my first time and walked around with a hole full of cum all summer.
What can we say, r27...?
You and we both know what you are.
11-12 best friend on a camping trip... hurt like hell... felt so amazing...
I was 18. I had been communicating by phone with an older guy (probably late 50s) who ran a Gay Information phone line out of his home. We arranged for me to come to his house in DC. He knew that I wanted to lose my cherry and was more than ready to oblige my urge.
When I entered the home, he started rubbing my crotch through my pants. I asked to use the bathroom, and when I came out I was wearing just a jockstrap. He asked if I wanted to go upstairs to his bedroom and I climed the stairs in front of him and wiggled my bare ass seductively. Upon entering his bedroom we both got completely naked and I laid down on my back on the bed. Knowing I had a virgin hole he went right for it with his tongue. I brought my knees up to my chest as he expertly rimmed me. After a short while, I was ready to suck my first cock. We 69ed for a bit, and then I lubed up and impaled myself slowly on his 7 hard inches cowgirl-style bareback. I rode him for a bit that way, and then I asked if he wanted to do me doggie style.
We started doing it doggie and I moaned loudly at one point and he asked "Are you cumming?" and I said "No it just feels good." When I finally did start to cum hands-free I told him and he pulled out and swallowed my load. It was an awesome introduction and did not hurt at all. I visited a couple of times in the years following that initial encounter. mmmm....memories.
I was only 13 while at my neighbor's house. She, Mary pushed me onto her parents bed an climbed on top of me. She was completely nude and I had an errection. She put my penis inside her(p) and kept rocking back and forth. I was afraid to get her pregnant so I pulled out, just in time. She then sucked the cum out of my hard penis. She immediately went to the bathroom and spit it out. Later that day I explained to her that swallowing my cum won't hurt her, and it would make me happier. The next time we went (all the way) she did dwallow!!! She told me it was a Lil salty but enjoyed making me cum. She then felt like a real woman!!!
I've never taken a dick up my ass and only have contempt for men who do.
R33, grease fire. Grease fire, R33. You two were made for each other.
That's because you're a pussy r33.
I was at a bar and a man offered me a drink. But he drugged me. He then took me too his house where there were 2 big black males in his bed. One was fucking me, one was riding my dick, and the other I was giving a blowjob to. I woke up with one black male on top of me. So then I moved him onto the bed then I fucked him. The the other 2 came in the room and started fucking me. So yeah I liked it.
I was 18 and met a guy on an aol gay chat room in my city the same age. He fucked me and it hurt like hell, he wasn't big or anything really. I was driving home and my nose started bleeding like a stuck pig. I had to pull over in an abandoned gas station parking lot til it stopped, which by that time my shirt was soaked w/blood. I still wonder what the passerby's thought of me standing there outside my car covered in blood.
I was a anal virgin until 64, then I met my present bf and he turned my ass out.
Unfortunately everytime I try to get close to his 24yr latino bubble butt, he loses it.
What with latinos thinking they are fem if they bottom.
R36, I think you put "then I woke up" in the wrong place. It should have been at the END of your post, shouldn't it?
i was 35 and super nervous so washed down a valium with vodka beforehand. i was so fucked up when he entered me that i giggled, and then he complained that for a virgin ass, i was pretty loose. of course i was- every muscle in my body was so relaxed that i was almost unconscious.
i've only done it a few times since, a couple of times where i hated it and once, maybe twice, when it was pretty fucking awesome.
i've come to determine that i have to be pretty into the guy, both emotionally and physically to enjoy bottoming. i could never do it with a random trick.
Under the pier. Bonfire party on the beach with friends from school... "Let's go for a walk" "Ok". Under the pier we stopped to smoke a joint. We would blow smoke into each others' mouths... and that turned into a kiss, then kissing... eventually we were fucking using suntan lotion for lube. It was great. We turned into fuck-buddies, fucking anywhere and everywhere, and that lasted for a couple of years.
High school, guy, very messy, freaked me out
Told this before here, but always nice to remember. I traveled to Copenhagen for few stays for holiday. I was 18. Went to a sauna, the only one I guess. Almost empty, it was day, but there was this attractive, hot guy and he fucked me. He was gentle, used a condom etc. I had a good first time.
He was ENORMOUS. I figured, "Hey, if I'm going to be gay, I might as well start at the top."
I was 19, he was 42. Didn't hurt felt great. Last time a Mexican with a 5 and a half inch dick fucked me. Perfect prostate orgasm for me. About Latinos not bottoming, I regularly fuck a 28 year out guapo Honduran guy and he loves it, BTW my dick is 7".
And so does everyone else on data lounge R46, that is has a 7 inch dick.
It hurt the first time, but now just feels uncomfortable. Took awhile to learn to relax and let things loosen up. I don't really get any pleasure out of it. Psychologically, it makes me feel good because my boyfriend likes it.
I was at a park and drunk and a big black man offered me to go to his house and I entered his house he told me to go to his room to rest but then he told me to turn around and take my clothes off then he started to butt fuck me then he made me put my dick in his ass then I gave him a blowjob. I woke up with cum all over me and I was freaked out then he came and gave me 4 beers to drink. Then he was fucking me for a long time and them i fucked him. I left after he went to take a shower. We fucked every Friday and Saturday.
That's the second first time you've had r36/r49.
First time was not great. Layed on my stomach in my first bf's dorm room while being fucked. He lubed me with some sort of desensitizing cream. Kind of hurt, felt like I needed to take a dump, but was nice to feel the intimacy of another warm dude on top of me. But never wanted to do it again. Perhaps it was all his Bette Midler posters, her voice on the record player, and the fact that his straight roomate was trying to sleep in a room separated by a few bookcases. Nevertheless, as I walked around campus the next day, I could still feel his cock inside me and I felt ten feet tall, knowing that no one knew I'd been plowed and cuddled all night by another dude. Didn't know what a Bette Midler queen meant at the time; he had a cock and that's all that mattered.
Second time was with the second boyfriend, who was much more experienced with the homosex. he had me on my back and lifted my legs onto his shoulders. It seemed uncomfortable but was really nice. I was rock hard. Had been insecure about being gay, let alone bottoming... until he came inside me while jacking me off with hand lotion and moaning like a baby. I got off by him getting off in me. Too bad he was a fucked-up ex-Mormon.
Third time was the charm. Was 19 or 20 and was literally picked up by a 40-something, tall, handsome leather dude after the bartender 86'd me for having fake ID. This was at the original Midnight Sun on Castro St.
Couldn't remember where I parked, so he rode me around on his bike, keeping my hand on his hard crotch. We couldn't find my car. I didn't know what a futon was, but the bottle of baby oil and his amazing, worshiping kindness made me feel safe with this total stranger. Also don't remember which drugs(s) we might have been on. Quaaludes? I straddled him and he moved my ass up and down over his cock. I came hands-free. We fucked the entire weekend. I was such a young, nerdy, needy, clueless, twink with a bubble butt.
My car had been towed, so he rode me back to my shitty college town on Monday morning while we were still coming off shrooms... so that I could get to my Chemistry mid-term (which I passed, but barely). He escorted me into the lecture hall, my ass so sore from being fucked, and then riding on a motorcycle while hallucinating about carbon compounds for an hour. He must have looked like a Village Person, and I was a happy puppy with a perky ass. It must have been so obvious to my Chem prof. and the tense lab TA's, all of whom were so "concerned" that I was spending my weekends in SF.
I came out to myself that weekend, and to some key people, but remained mostly in the closet. This was 1980. Really liked getting fucked by the right guy.
I was at a bar and when I was walking out I was all drunk and a man told me to go inside his van and then as I walked in he told me to take my clothes off then he started giving me a blowjob then made me bend then a other man came in and started to fuck me but for some reason I liked it and I started to give them blow jobs and fucking them.
R53 - another one using the drunk excuse.
It was after a party a High School teacher had. I had graduated the year before. I don't remember much. Only that the FIRST time we didn't use lube, and I bleed. The next few times we fucked on the beach, and I wound up with lube, blood and sand in my butt.
Boyfriend and it was painful, the worst part was that I'm tall, and he was short, and tried to fuck me doggie style, my back gave out trying to endure it.
I love bottoming now though, but the right position makes a difference
was by a tranny i was seeing and did it because i loved her.. she had a little dick so it didnt feel like anything ,but i felt like her bitch, the second time was a black guy who had a nice 7 inch cock,he fucked me really goodand made me like it..