How to Lose Your Virginity ...And How Not To (18 page)

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This guy I knew, Jeremy, broke up with his girlfriend who was like the biggest slut in town because he found out she went "skiing," if you can visualize a girl doing that motion. And by skiing I mean Janelle jerked off two guys at the same time. I moved in and started hanging out with her.
Kevin, 26
Seacrest Beach, NJ

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FAIR GAME
Roland, 31
It was with a girl in the very far suburbs and the further you get out of St. Louis, Missouri, the more trailers and farms you get. And I’m with a girl from way, way outside of St. Louis – farm and trailer park country. Her name was Caroline Arkey and I wouldn’t mind finding her again and believe me, I’ve been looking.
We watched Scream 2 and we’re making out and the girl says to me, "Do you want to have sex?" I said, "No… I don’t know." She’s like, "Well I have to tell you something." "Well what is it honey?" "I have to tell you, I’m already pregnant." That was what convinced me because I couldn’t get this girl more pregnant. She’s already gonna have somebody else’s kid. It’s a free go!
She was about two months along, I guess. Barely showing but enough so that her breasts had swelled so nicely. We had sex and about 12 minutes later I packed up to leave.
So the point is, first time, lost my virginity to a pregnant girl when I was 17. Wonderful experience, she was 15, her kid now is maybe 10. Didn’t use a condom. She was already pregnant, right? So what’s the worst that could happen? Little did I know like about STDs. But I’ve given blood since then and they never called. They never called so I’m good, right?
BREAKING AND ENTERING
Yosef, 30
I met this girl at my 15th birthday party I was having at a friend’s place. I was about to take her home but when you’re 15 and you live with your parents and four brothers you can’t just take a girl home for sex. I decided to take her to my school in Tel Aviv, Israel. I told her that my father was the sports teacher and that I had keys for the gym. Had her wait by the front door and I snuck around the back, hopped a few fences, broke a window, then opened the front door for her from the inside.
That’s where I had my first sex, in the gym, in the middle of the night on those real big high jump mats – the huge ones you had to climb up to get on. I didn’t know a whole lot about sex but it was fun. It was comfortable to have sex sunk deep down in that huge mattress.
That girl, I never called her and I feel bad about it now, but I just left her there in the school. She was from a different state so I don’t know if she knew how to get home. I didn’t even care. I just left her. Then when I got home I thought, "Geez, what about that girl?" Since then I’ve learned to take better care of girls.
The next morning I told all my friends like, "Yeah, I got laid on my 15th birthday in the fucking school with a fucking hot girl." They didn’t believe me so I showed them the broken window.
MY DRUG BUDDY
Chip, 22
I met this girl from the neighborhood. We always got high together behind my shed. I just thought we were weed smoking buddies. I had no clue this chick liked me. I'm walking her home one night in the rain and I was like, "I'll walk you half way," such was our routine. We get to the halfway point and she's like, "I got to tell you something." "What's up? You want to smoke again?" She's like, "I like you. I want to date you." She wasn't that good looking so I ain't fuckin' dating her.
She just starts kissing me. She kind of like bum-rushed me. I think she liked me a lot because she was pretty aggressive. And it felt kind of good when she kissed me. I wasn’t like blown away by it, but holy shit, I pretty much got a fucking boner from just kissing her. So I figured, "I got a boner, I might as well screw her." We're kissing in the rain and shit. There were these woods in our neighborhood, right down the street from our halfway point. We go by the woods, and I don't know, I think she had a condom; she had to have. Maybe she planned it; I never asked. But what I do know is that we ended up fucking in the woods for two minutes. I fucking two-pump chumped her. That was about it. I had a good time so I walked her all the way home that night.
We fucked for awhile and then she wanted the relationship but I told her, "Look. I'm not doing it. I don’t want to date you but we can have sex and get high behind my shed."
SECRET HANDSHAKES
Ray, 26
I dated this girl for three months which, to this day I think is still my record. Veronica and I got close but she would never sleep with me. All my friends were getting laid. Finally I just got tired of it. I called up this other girl who Veronica went to school with, a known slut, and asked her out to a movie.
I pick her up, we're driving to the theater and she asks, "Why'd you call me?" You know so, I tried my best line, "Because I really like you." And she's like, "Yeah, bullshit. Do you still want to go to this movie?" I said, "Well what are some other options?" She said, "I don't know. What else is there to do?" So I took her over to my buddy Kurt’s place.
Kurt had this playhouse we'd play in as kids. But it was a big playhouse. It had bunk beds and all that B.S. Three of my buddies lost their virginity there. We called it the "Stabbin' Cabin". It had no lights so all of us had Indiglo watches to work the combination lock on the outside door. And it was all coordinated, you get inside and the lights wouldn't work so you had to sleep together. There was a stash of condoms and when you were done you'd just throw them in the fireplace. Every Saturday morning we'd get together and burn up the used ones.
This all got back to my ex-girlfriend, it being with a girl she knew, so she showed up at my house in tears, absolute tears but I was away at basketball camp. My old man had a talk with me when I got back. But yeah, that was the Stabbin' Cabin.
HIJACKED
Dave, 23
It’s the start of my first year at college and I’m anticipating meeting a chick at some keg party or somewhere, who will take my virginity. That’s how I thought it would go down but it didn’t quite happen that way.
A couple seniors on my hockey team came over to my room and said, "Hey you want to go and blow lines all night?" I said, "Yeah. I’ll blow lines with you guys." I figure, "Hell, why not," so I go and blow lines with them. They say cocaine is supposed to limit your sex drive but it didn’t stand in my way that night.
After a ton of partying it's 6:30 in the morning and we're riding around in this one guy's Ford Explorer. We’re going crazy, going stupid and we see this girl walking back from some apartment. So we’re like, "Yo. What’s up? Want to get into our car?" She gets in. I figure we’re gonna go get breakfast.
These guys start saying shit like, "We’re gonna take you out to the woods and rape the shit out of you. We’re gonna fucking tie you to a tree." She understandably gets freaked out. I try calming her down, telling her that they’re just joking. Meanwhile we turn off the street down some farm road. The whole time the driver is going on and on about how they’re going to chop off her legs and all this weird shit. We were all coked up.
She’s like, "What the fuck’s going on?" I say, "Don’t worry, honey. Everything’s gonna be OK. These guys aren’t that bad." Meanwhile she’s getting more and more frightened and they turn off into a farm.
They slam on the brakes, corn stalks seven to eight feet tall on either side of us. She jumps out balling her eyes out. I go chasing after her, I’m like, "Listen. They’re lying. It’s no big deal." Somehow I get her back into the car. We go to the breakfast place. It’s all over with, but she’s still shaken up.
After breakfast, she and I went back to my dorm room. She’s still whacked out, asking me, "What were those guys thinking? I was so afraid for my life." I massaged her shoulders to calm her down. Howard Stern came on the radio, he had a stripper on or something funny like that. She loosens up, starts laughing a little bit. We got to talking and then things happened. There we were.
It had a crazy beginning but it ended on a good note.

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We’re lying in bed and then he was like, "Here’s a picture of my kid." It was just a bad situation.
Mary, 22
Bronx, New York

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TWO CAN PLAY THAT GAME
Kip, 23
I was 14, never met the girl before in my life. I talked on the phone with her for about two days, talked bullshit, whatever. My friend was trying to hook me up with her. It was kind of arranged which was the fucked-up part, and kind of made it uncomfortable.
End up going over to my friend’s house and he and I both lost our virginities on the same night. Different girls, different rooms, but same night. He was raised by his grandfather so he had his run of the place. I'm chilling up in his grandfather's attic, met her, and lost my virginity to her that night. Probably the worst sex I've ever had. It was basically on a bare floor surrounded by spray-painted walls - tags me and my buddy put up there. My boy left two cigarettes up in the attic for him and I when we were done. He went downstairs, lost his virginity, came back up and we smoked. I never spoke to the girl again. Gave her a hug when she left his house. I fucking gave her a hug then sent her on her way.
The girl I slept with ended up going to school with us later on. She switched high schools and I ended up finding out that she had fucked half the people in my school. Then when I was like 18, 19, I found out she was doing low-class porn. So, interesting story, but not the best.
Honestly I wouldn't want to lose my virginity any other way except for a one-night stand. Otherwise you know how that goes, you get attached... blah, blah, blah... fuck that. I gave her a hug, peace, chucked the deuce up, "Later." Never talked to or saw her again until she transferred high schools. I don't think she cared either. She was probably into taking virginities. She was like on a warpath, taking virginities from what I later heard about her.
But here's the actual reason it went down the way it did, because my girlfriend at the time who was the same age as me, she went and cheated on me with some other guy and I come to find out that she lied about it and said that he raped her. Come to find out he didn't fucking rape her. She liked him, went to a fucking party with him and lost her virginity. He was like four years older than her.
I went and confronted the guy. I had a knife on me. I was going with the intent of hurting the guy. Instead he sat me down to talk with me and told me what really happened. Then one of my close friends told me that she walked in on them, which verified it so I was like, "Oh. All right, well fuck that. I'm going to get back at this bitch." My buddy, the one who set us up with the girls, he was with me the night my girlfriend told me she was raped. So he decided to find girls we could have sex with so I could get revenge on my girlfriend.
We were actually still going out at the time and then as soon as I got it done I called her up and told her how I lost my virginity and she was so pissed off at me, which is sad because she cheated on me and lost her virginity to someone else first… but, oh man, talk about pissed off. That's how I broke up with her. Then she still tried to get back together with me. After all of that she still tried to get back together with me.
TELLING IT LIKE IT IS
Ramona, 28
It was with a sucker M.C. What led to it was my naïveté and my stupidity. But then again, it didn’t come to anything because his dick was so small that I don’t think that he did really anything.
When he was doing it, he was saying, "Whose pussy is it? Whose pussy is it?" And I was saying, "It’s mine, it’s mine." So he’s a jerk… and he has a small dick.
I knew he was a loser, but to be quite honest I was tired of being a virgin and I wanted to just experience it. And on the real to real… I wasn’t feeling him, and I guess he wasn’t feeling me so that’s why, overall, it wasn’t good. Maybe if I would have been in love, and he would have been in love with me, it would’ve been another thing. But all it was was me being in a hurry to not be a virgin anymore and him being in a hurry to get in between my legs.
I waited almost two years before having another sexual experience because I did not enjoy the first one and I was like, "If that’s the hype, I can do without." I really started enjoying it when I was 24, so it’s like I could have waited until then.
Seriously, you’ve heard it before but I suggest you wait. Wait until you really feel something for that one person. Not just like, "Ooh, he’s cute or I like his style or he dances real good or he’s funny." No, no, no, no, no. I mean just feel that person in the true sense of it. And then you’ll be able to enjoy your first experience. But if not, then it’s a waste of your time and to be quite frank, pussy gets wrinkled, you know what I’m saying? Your parts get old. So if you don’t keep yourself for the one person you want to share all your first experiences with then you’re just gonna waste your body. It’s like anything else. You wear shoes too much they get used – worn out. If you use your pussy too much, girlfriend, it’s not gonna stay tight. And they don’t like loose.