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.