I was 9, she was 22 and a model

I was 19. It was with my first serious boyfriend. He was not a virgin, and it took me weeks of yammering to convince him I was ready. I think he was uneasy about deflowering someone. The sex was over in about 3.2 seconds and wasn't anything to write home about. Luckily, it got a lot better.

 

My first time was when I was 28. For some reason I never saw it as something really important. That combined with the fact that I was intimidated at the thought of talking to a girl, made me progress slowly into normal adult hood. The first time as you would imagine, was nerve racking and quick.

 

Mine was relatively normal, I suppose, minus the fact that I was a bit old. I was 22. It hadn't happened before that because I tend to get hung up on girls that don't like be back and don't often treat me very well. I dunno why; I'm fucked in the head. Anyway, It was Halloween my senior year of college. My group of friends all decided to dress like various members of the Peanuts gang. We had a Snoopy, Linus, Pigpin, Peppermint Patty, Charlie Brown, Lucy, and I was the Great Pumpkin. It was a fucking awesome costume and totally deserving of getting laid. Anyway, we met another friend of mine out that night, and she was dressed like a cougar (the MILF type) in leopard print slutty clothes. Anyway, we took a lot of shots, ended up making out at the bar, and then the group headed back to my place for a late-night. She and I went back to my room where we proceeded to get down to it, even though halfway through my friend opened the door so that everyone could cheer.

Regardless, it was a pretty normal experience minus the costumes. This girl turned into a sort of FWB-type thing for the next few months which was nice until I left college.

 

I waited until last year at the ripe 'ol age of 21 and it was my gf's first time as well. It was not fun nor easy turning girls down prior to that fateful night but I am glad I made the decision to do it when we were ready. It was entirely worth the wait, we had an incredible time (and still do), and I have zero regrets.

 

I'm 22 and lost my virginity a few weeks ago.
I was always pretty shy with girls and over the last 1-2 years it slowly started to become better.
It was with a friend of mine, she's 28 and I knew her for over 2 years. She came over one evening to hang out and brought a half full bottle of liquor with her, which we then proceeded to drink over the course of the evening.
We were both drunk and I didn't see that one coming at all, it had never been that way before with her, but she suddenly started kissing me and then we had sex.
After all it wasn't worth it since there was a huge aftermath and, to put it in her words, she acted like an idiot towards me.

 

We were both 17, and had been going steady for a couple of months. Since we didn't live close to each other, or have anywhere to go, we had to wait until I had my drivers licence. Then, we hightailed it to the Sundale Motel in Southport (being the classiest place I could afford on my wage) and got to it. And it went extremely poorly.

She cried and it hurt so much for her we gave up without even getting it all the way in. There was some blood, and I have no idea how we didn't get it on anything other than ourselves.

We then spent an awkward afternoon not talking about what had not happened.

This scenario repeated itself for several weeks until she told me to go park the car one night, get in the back and "just fucking do it." We got there, but it wasn't exactly magic for either of us.

 

I was 17 and it was the first week of college. She was my age and had a tramp stamp. I was not expecting it at all. It just happened. I didn't feel nervous... intellectually. But my body was tingling all over (like ants...) so I couldn't really feel any of the pleasurable stuff.

I dropped her off at the subway station and made my way back to my room. Once I turned on the lights, I realize that not only did I lose my virginity but I also earned my red wings. So THAT's what that smell was.

 

I was 21 and had been so terrified of men by my super strict dad that I could barely talk to guys until I went away to college. And even then, I was totally awkward. I managed to get a boyfriend in college but had enough sense not to bang him (although I totally regret this now) full well knowing that I would become beyond a stage five clinger. I told myself I was saving myself for marriage and that's how I got through the rough spots while honing my bj skills.

So when I went to work for my parents after college in their restaurant, I was really miserable. When I met The Devil (I never refer to him by name) he was a waiter in our restaurant, nothing to look at (kind of like Richard Belzer from SVU), coke-head, arrogant, was 32 and separated from his 19 year old wife, living with his sister, and my dad absolutely hated him. And for some reason he made the hairs on the back of my neck stand up just by walking into the room. One night we were both closing, had a drink at the bar, locked the doors and banged in a booth in my parents' restaurant...the one where my dad always met with vendors and salesmen. Hmmm... Daddy issues much?

I'm glad I did it with him even though the mind games that ensued shortly after are almost unbearable to reflect upon. He knew what he was doing and I was old enough to know what I was supposed to do. Believe it or not, it was pretty good sex. I just remember that feeling when he first was inside me--that initial pain with the push and then how awesome it felt to feel myself stretch all around him. I just closed my eyes and enjoyed every new sensation. Fucking awesome.

 

I had just turned 19. We had been "together" for a month, two weeks of which was spent on Christmas break, the other two of which had progressed from me being the first boy she'd ever kissed to third base. We were fooling around yet again in her dorm room, and she was sort of grinding her pussy against my dick on top of me. At this point, a sort of "just the tip" thing occurred and I made a half-hearted joke about it. Next thing I knew, she had slid down on top of me, letting out a sigh. I am positive her pussy has never been just quite as wet, or slid down quite as easily, as it did that night. I pulled out and put on a condom and we fucked; I was so nervous about the condom breaking that I pulled out of her to come inside the condom.

She lay very quietly for about 15 minutes, with her trying not to freak out and me trying not to freak out about her being so quiet. Then she rolled over and said "let's do it again". And we did.

 

I... don't know. I remember the time I tried to lose it. I was 18, and we'd been dating for 6 months or so, and were each other's firsts for pretty much everything. She decided she was ready, we romantically squished up on my single bed while my parents were out, and... I literally couldn't get it in. We weren't totally retarded - we knew about foreplay and lube, and had had plenty of both. Still, I couldn't even get a finger all the way in she was so tight. After repeated failed attempts, we gave up and cuddled, both mildly bemused and slightly traumatized.

I think we successfully managed it a couple of weeks later, but to this day, I can't remember the experience. I remember my first kiss vividly, down to the chair I was sitting on at the time, but I can't remember losing my own virginity. How weird is that?

In totally unrelated news, I had a ludicrous pot habit back then.

Edit for repressed memories: Oh, and the first time I ever got a handjob from the girl mentioned above, I freaked out immediately after I came, and was generally weird. Ladies.

 

I was 15, she was 16. We had no idea what the fuck we were doing and it was awkward as hell.

 

I was 15, about to turn 16 in a month, and she was 15 also. We had been talking/hooking up/whatever you did at that age for a few weeks and I had thought she was a virgin also. One night we are at a party and we are both kind of drunk. We go outside and are hooking up against a car with people walking by and she tries to take my pant, I said no because at that age I still had some morals and didn't want her to lose her virginity drunk against a car in one of our friends front yards and in full view of numerous people. Later that night we're talking on the phone and she asks me why I wouldn't and I tell her my reason. She responds with "Oh yeah I lied I had sex with my last boyfriend." About a week later we had sex, it was uneventful and I barely remember anything about it, except that she just laid there.

Kind of regret not going for it the first night, this post would have been a lot better.

 

Well, mine is fucking weird.

I was 12.
She was a 17-year-old sitter.

First off, it wasn't just me she was watching, there was a 5 and 6-year-old there that my parents didn't trust me to watch.
I was a pretty irresponsible kid.

The younger kids were long asleep... it just happened.



The weird part? Her mom was my teacher at that time.
It was definitely too early for me and all, but I don't think it screwed me up or anything... unless you count being a massive man-whore and never holding down a steady relationship for any more than 8 months, but that's fun.

It's just still incredibly awkward when I go home to see my parents now that I'm 27 and she's walking around the neighborhood with her mom, so they naturally stop to chat. I'm pretty sure neither of us ever told a soul about it to anyone specifically.

 

We were both 16, with her being a few months older than I. She was one of the sluttier girls in school and wasn't a virgin. We started hanging out and she seemed overly anxious to take my virginity. Problem was, we made an effort, I shot my wad way too soon and then she made fun of me which made me self-conscious and not want to try again. This happened more than once. The first time, I was sitting on a couch and she was grinding her pelvis onto my cock and I JIZZED. IN. MY. PANTS. I tried to pretend like I just had a chill, but it was pretty obvious. It took a week or two before I worked up the guts to try again (we didn't talk about it, I would just stop her when things got hot because I would get scared of blowing too early again; made it all so much worse). When we tried again, we managed to get her mouth around it and I blew my load again. Repeat as before. Third time I made it to her entrance, got the head in, and immediately fell on top of her as I blew my load again. I guess this sort of counts as the first time, but it took another attempt before anything resembling what people recognize as sex actually happened.

Not weird, but definitely embarrassing. She certainly didn't make it any easier. She had nice tits though, so no hard feelings.

 

In response to the Neg rep....

I've posted 50 times in almost two years. Why would I post out of nowhere and lie about something as awkward and worthless as when I lost my virginity?

I could say I fucked a nun and a burro in some fucked up threesome for the first, and it still wouldnt matter one fucking ounce to me or anyone here.

 

Dude, do you have any more details on this? A junior/senior in high school fucking a 6th/7th grader is messed up. Were you kind of hitting on her? Did she rape you? Did you have sex with her again?

 

Actually, it's more common than you think. I know quite a few of my friends who lost their virginity in this manner. While it looks terrible that she was in 11th grade and he was in 7th, it's really just, what? four years? That's not really that much of an age difference (yes, maturity, but whatever.)

Maybe he was hot. Maybe she had power issues. Maybe she wanted to be bad and have some dangerous sex--you know the kind that is taboo and she might get caught. Maybe she saw "Adventures in Babysitting" too many times and thinks Elizabeth Shue should've fucked that kid. Maybe she was high or bored. Who cares?

If her mom banged him, THEN it'd be a problem.

 

Only five years? There is a BOATLOAD of maturity that goes on between early junior high and late high school. If it was a 14 year old fucking a 9 year old, would that be ok because it was only five years?

Also, If we flipped this and it was a 17 year old guy that fucked a 12 year old girl he was babysitting, would you have the same cavalier attitude about it? A fucking 17 year old should have the maturity to know you don't have sex with a 12 year old, I don't care how common it is, that is fucked up.