Males and Females

Dunno how I missed it, but congratulations on trading v for v, Schmidt. Since everyone else is swapping stories, I was 18 when I lost mine, didn't use a condom, didn't pull out, and didn't get her pregnant.

Man mine was terrible at first and then amazing at the end. Was 19. We had hooked up the night before but I was too wasted to get it up. The next day we hooked up again at her house (she still lived with her mom) but I was so nervous because of the night before and feeling the pressure of still being a virgin that I couldn't get it up again. Her gay male friend was also drunk passed out on the couch. I couldn't get it up even when she went down on me. At that moment I thought I was gonna die a virgin.

Finally I just rubbed my cock on her clit and finally got it up. We banged with a condom and it was bad and lasted like three minutes before I came. Didn't feel very good for either of us and she was pissed. A half hour later we banged again but my cock wouldn't stay up. Finally she was like "fuck it" and took off the condom. Then it was amazing. We banged til 6 AM and I made her come from head for the first time in her life.

Turns out her friend woke up from his drunken slumber in the middle of the night and heard us banging all night. The girl lived in the hills so I had to get a ride to downtown Oakland from her mom. To do that I had to pretend to be the gay guy's boyfriend to get a ride with her mom. However, the guy was fucking pissed at me, so he was being super rude and sullen. Awkward car ride, to say the least.
 
Yeah, I lasted like 2 minutes of my first time. I was insecure as fuck, and thought my girlfriend was out of my league. In fact, the whole time I was in that relationship, I came within a few minutes. I slept with her a few years after we broke up just to prove myself and put that part of me in the past.

I usually can't get it up for the half hour or so following an orgasm, and since my girl has a pretty strong libido, I've learned that I need to keep myself in check and make sure she climaxes before me.

Period sex is aight. Just gotta breath through your mouth if you go down on her.
 
Loss of virginity stories, yay.

I was 19, and we were both each others' first everything. We hadn't done anything outside of making out at that point, but we both got really drunk and somehow ended up naked in my bed. Didn't have any condoms, so we waited until the next day. Amazingly, it went incredibly smooth, she climaxed numerous times from different things, and it lasted a good hour or so. Came inside of her during a really intense mutual climax, then she started crying about how great she felt about everything we had going.

Still one of the best nights ever.
 
Loss of virginity stories, yay.

I was 19, and we were both each others' first everything. We hadn't done anything outside of making out at that point, but we both got really drunk and somehow ended up naked in my bed. Didn't have any condoms, so we waited until the next day. Amazingly, it went incredibly smooth, she climaxed numerous times from different things, and it lasted a good hour or so. Came inside of her during a really intense mutual climax, then she started crying about how great she felt about everything we had going.

Still one of the best nights ever.
... I ain't gonna lie I got a boner reading that
 
Lucky you.

I was 18. It was the summer before I started college. I was in Buffalo, NY at my cousin's parents' beach house on Lake Erie, and my cousin threw a party since his parents were out of town. Copious amounts of Jack Daniels were in supply. A round of beer pong was in order, a game which I had never played before. Well, it turns out I am naturally gifted at this game, and played on a team with my cousin opposite the person to whom I would eventually lose my v-card. After a round she invited me over to her team, and I continued to dominate. Impressed by this she invited me to another round of whiskey shots and eventually started making out with me.

She had a sister, and another guy there had earlier instructed me that the sister in question was off limits. However, the guy was not present and the sister insisted I make out with her, even though I was already on the couch with the other girl, getting to 3rd base with her. So I ended up making out with two girls at once, two sisters.

Sadly, the sister I ended up taking to bed was the less attractive (fatter) of the two. But I was so drunk at the time my only priority was to get laid while I was still in high school (the American Pie mindset was in me at the time), so off I went. She had a condom for me to wear, though I didn't climax. We banged in a couple positions, then she started giving me fellatio before passing out.

I walked home to my grandmother's house and woke up the next morning feeling like a million bucks. I told my uncle later that day and he high-fived me while my cousin looked on enviously.
 
If not cumming still counts, after dodging emails and calls from the gay guy I mentioned previously, I met up with him at our usual restaurant/bar with the intent of recording an admission, and he told me that not only was there heavy petting but that he actually gave me head until I pulled out and said no, so technically I guess I lost it at 23.
 
Lost my virginity very awkwardly at the age of fifteen.

Went to a friends house specifically chosen because he lived close to my girlfriend at the time. Her parents weren't at home, never knew why and never asked. We sat on her bed for a while watching tv and I don't even know really, we didn't kiss or anything, we just came to a sudden consensus that it was time to lose our virginity. Pulled her pants and underwear off then awkwardly and apparently painfully rammed my dick in her. There was a bit of blood and she was obviously uncomfortable but I was fifteen and didn't have a single fuck to spare. I flailed around fucking her for maybe two or three minutes... no concept of subtlety or being gentle yet learned. I came inside her and we just kind of looked at each other before she staggered off to the bathroom to clean herself up.

We really didn't talk about it afterward and didn't date much longer. Didn't have sex again until I was seventeen.

The second time was almost as odd as the first. It was in a mall bathroom during school. Our schools basketball team had made the state playoffs and they actually took us to the game. Next to the charleston arena is a big mall and they let us go there before the game. I had been spending a lot of time with a slutty, tall blonde from the dance line. I talked her into letting me fuck her in the bathroom in a stall. She was actually the same height as me so she kind of bent over and held the wall and we made it work. Again, I came inside a girl with no form of protection. Dumb kid was me.

Didn't feel the slimy wet happiness of a vagina again until after graduation but at that point it became much easier, it seemed.
 
I remember when I lost my virginity my girlfriend used a red condom. I didn't know it was red until after I came and pulled out and looked down at my dick thinking I had mutilated her pussy. We banged for a good 45 minutes or so. She was super loud too. It was hot.