Read How to Lose Your Virginity ...And How Not To for Free Online

balls… that was the big thing, tickling the balls, man. That made my ears wiggle.

FATHERLY ADVICE
Leif, 22

The first time was with a hippie chick. She was quite a hippie so naturally she was… natural down there. Quite a forest scene down there. I wasn’t ready to go down on her, couldn’t handle the oral thing so I figure we’ll get into some regular penetration. I put the rubber on, started going at it and five, maybe ten minutes into it, the condom kind of got wrapped up in some of her hairs there and sort of got whipped right off. I had heard that it’s possible for condoms to slip off inside and that’s what I figured had happened, but when I looked down and saw the actual entanglement situation, I was a little disturbed. It broke the mood for awhile. We hung out for a bit, smoked some weed, then got back into it after about a half hour or so.
It finished well for me but I did have to do some mouth work on her after the fact to make sure she was satisfied. My father once gave me some advice that I’ve always tried to follow. He and I were in the garage sharing a cigarette and drinking some whiskey and he just randomly said, "You should never enter a woman unless she’s had at least two orgasms." He’s a smart man, works in home health care so he’s got a mind for knowing what people need and getting it taken care of.
It’s easy for a man to get off whereas women, there’s more work involved. If you’re going to get off, you might as well put in the work beforehand. So I made sure by the end of the night she at least had two.

THE INSTRUCTION MANUAL
Mark, 21

I was eighteen and my girlfriend at the time and I were at my dad’s house in Cape Cod, Massachusetts. She had done it before, which felt weird. I was really kind of nervous, like a stage fright sort of feeling. It wasn’t like a losing-an-erection type of nervous but it was a definite intense anxiety. But she was extremely patient with me. Before, during, and after the act there was feedback and instructions. She was a feminist organization leader at Penn State and coincidentally a very good sex coach.
One of the things she told me was that a lot of guys will tend to just thrust downward: up and down, up and down. That doesn’t really stimulate the clitoris. The way she described it was, for guys it feels good when they’re pushing down, but for girls it feels good when the guy is pushing up. She got me moving in that motion and she was right. It’s made all the difference in my experiences with her and every girl I’ve been with after her. I’m not bragging but girls tend to like that better than the "Wham, bam, thank you ma’am" type of thrusts.
Losing my virginity was a little bit of a bigger thing than I thought it would be. It’s an important physical kind of rite of passage of sorts. And you want to do it well, you want to do it right.
We did it that first time and it was fun, but it’s a difficult thing to separate the anxiety of the whole situation out of it. The next time we did it, and I know this sounds counter-intuitive since guys are horny all the time, but honestly I was still nervous about having sex. But with her help I acclimated to it and she was a good coach.

LIKE A WALK IN THE PARK
Ann Marie, 31

I was 13 and I lost my virginity at a carnival, like a little street fair in my neighborhood, to a boy that was actually a… OK, he was a carnie. And I lost my virginity in a broken, unused tilt-a-whirl car inside the back of a semi truck. For some reason I just thought that was the biggest, greatest idea because you know, you’re in middle school and everybody’s talking about boy-girl stuff. And I was just, "Well what’s the big deal? I’ll just go do it." And so I found the quickest, easiest route and it was a little carnie kid who was 16, just hittin’ his puberty and I think he may have lost his virginity that day too because it sucked. Not that it ever got better for me ‘cause I’m not about the guys. I can’t