How to Lose Your Virginity ...And How Not To (11 page)

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I said flat out, "I think you should show me your penis." It was bold because I was so young. He said, "There’s about a zero percent chance of that happening." We’ve since talked about how funny it was that it went from a zero percent chance to eventually going all the way.
Kathryn, 24
Crystal Lake, IL

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KNOCK, KNOCK. WHO’S THERE?
George, 22
It was totally a one night stand, like hardcore. This guy Johnny who was friends with my older sister would always come over to our house and bring over girls he met from the bar. My sister didn't even live at the house anymore but he still used our house as a crash pad. So he brings this lady over but she's totally not interested in him at all. I was sleeping on the couch and woke me up when they came over. And she was just all about me. She laid down next to me on the couch and he left. We made out for a second and then she started, you know, she went down my pants, got on and whatnot. It's funny, I've told this story a million times but I can't explain why it happened. It lasted maybe five seconds. She was 34. I was 14. About a 20-year difference.
Johnny totally hooked me up, inadvertently. I let them in and she was hot but he could see that she wanted me so he gave it the go ahead. You know, he wasn't a virgin - he was like a 30-year-old man. If he was 16 he wouldn't have been as generous.
She actually told me it was the best sex she ever had. I didn't really believe it. I mean, I still don't. A young guy like that? Maybe she was letting me down gently or maybe she was endowing me with confidence.
I wish I could say it was special and everything. It happened so fast I didn't really have time to enjoy it. Pretty much right when she opened the door it was obvious that because of how young I was that she wanted to do me. If I had been an older guy, I don't think it would have happened. She just wanted to rob the cradle - that's my take on it.
FEMALE EXPLORATION
Natasha, 34
A couple of years ago I lost my virginity to a woman. And she is the only woman I've ever had in my life. Her name was Andi.
I was vacationing in Miami and I had just got divorced. One of my best friends was trying to hook me up with guys and I was not really into it. We decided to sail from Miami to the Bahamas. We were a group of 10 people on a beautiful boat. He later told me that he paid this woman a couple of thousand dollars to do me, but I didn't know that. She ended up falling in love with me.
We were all on the boat and we were doing ecstasy and coke and weed and champagne and the yacht was beautiful, the ocean, everything and the next thing I know I have this really beautiful, sexy Pocahontas-looking woman, Andi, going after me. She was my first woman experience and it lasted three days and it was fantastic. I have never had a girl since then and I don't think ever will. I'm not really into girls, I'm really hetero. But I have to say that that experience was fantastic. It was the first time I had a dildo used on me. It was different because I’m not one to masturbate. I'm very active, I'm too busy with my work and music to do stuff like that. But that experience was great as well... both experiences, the first man and the first woman were both fantastic.
SURPRISE
Jason, 40
I was the guy in school, when asked, "Do you masturbate?" didn’t raise his hand. I didn’t even know it was an option. I wasn’t as frustrated as I would be years later, after I realized what I had been missing.
I lost my virginity at 19. It’s about the right age to lose your virginity, I guess. We were having a party at Ted’s house. I was going to community college and we invited a lot of women over. This party was going along and then late in the night, Ted and this woman disappeared into one of the back bedrooms. Someone was looking for him so I went around knocking on the back bedroom doors. I walked into this one room, my friend wasn’t around but there she was this strange woman in a teddy. Ted and I looked very similar to each other. She looked at me and said, "Fuck me." So I did.
It was on Ted’s sister’s bed and the sheets were very, very, very soiled. So he had to explain to his sister what happened in there. My buddy was also upset because I had locked the door and I think at one point he was trying to get back in.
She was so drunk she didn’t care who it was. I mean, she came to a party wearing a teddy underneath her clothes. But I did do the right thing and gave her a ride home. But yeah, it was with a stranger I walked in on at a party. Didn’t even know her name. I think it’s one of the reasons I’ve turned out to be less of a romantic.
THIS ONE TIME, AT JOB CORPS...
Ruby, 24
I'm bisexual. And I've always known that I'm bisexual. And I really don't have a preference between girls and boys. I love them both. So I lost my virginity to a boy at Job Corps on Valentine's Day. I lost my virginity to a girl that same year in Job Corps.
I didn't know it was going to happen. I was supposed to go home for the weekend with a different friend but she never showed up. And this other friend of mine from Job Corps was leaving. I was like, "What the hell. I've got the weekend pass. I’ll go too." I had sex with the woman who came to pick up that other friend. I left with them and I started giving her a massage while she was driving the car. She had somebody switch and they drove, and she sat in the backseat with me and we just started making out and it just got heavier and heavier.
Eventually when we got to her house we went all the way. Her husband watched so that was pretty neat. She said I did a really good job. They were nudists anyway so we just stripped down and stayed naked for most of the weekend.
INCOGNITO
Clay, 44
I was invited to a Halloween party by a friend. It was a gay Halloween party and I didn’t really know anyone there. I was 22 and not out of the closet yet. I came from a strict family and my mother told us kids that if we had sex before we got married, our arms would fall off. Very old school. It was years before I could come out to my siblings. Because of my background, I held on to my virginity for quite awhile.
The whole party was basically naked. I was dressed as a Banshee, one of those Irish folk monsters that screams all the time. I was wearing basically a loincloth, my eyes were blacked out and I had hair glued all over my body. I looked really scary, but I was basically naked too. I got real drunk on these shots called Jellybeans, which were seven different liquors all layered together. I blacked out and the next thing I remember was coming to in the middle of a ménage a trois, and I had somebody at both ends. I wouldn’t assume I was forced into it because I was having a good time. Two boyfriends decided to get me involved in something. They coaxed me into a bedroom and I was so drunk I didn’t know what was going on until I came to. The one guy’s costume was just a towel and shaving cream on his face. I can’t recall what the other guy was wearing. It was mayhem. It was great. I was having fun and then I blacked out again.
The next morning I was shaved head to toe. It went from being a threesome to a gag. I had absolutely no hair left on my body. I guess they wanted to see how much of my hair was real and how much was glued on. It was a sleazy way to lose it but I thought it was funny. I saw the guys again a few times but they were in a committed relationship. I was just a fling for the night.

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She grabbed my hand and took me to the other side of the basketball court, to the women’s locker room. She said, "I hear you’re a virgin. Virgins aren’t allowed to start on the defensive squad." Then we fucked in the women’s locker room.
Tim, 28
Piedmont, Oklahoma

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ON THE DOWN LOW
James, 44
My sister and I went to the same high school. She was two years ahead of me and we both went on to the University of Pittsburgh. I’d say about 78% of her graduating class went to the University of Pittsburgh and about 50% of my graduating class went there as well. Her boyfriend from high school also went there, so they had been there for two years prior to me.
I had always felt some strange sort of, not so much sexual attraction, but I would always catch long stares from my sister’s boyfriend. I would turn and he would be in on me, just staring.
When I got to college I lived in a co-ed dorm – every other floor was boy, girl, boy, girl. They housed everyone in chronological order. Our last name started with a "D" and so did my sister’s boyfriend’s. So my room was on the same floor as Simon’s room.
Once in awhile I’d hang out in his dorm room and at one point there was a real nice girl, Sherry, in his room who I thought he had something going on with. The three of us were drinking and stuff and Simon got out this book called, Total Massage. We’re flipping through it, we ate some mushrooms you know, we’re feeling all cozy, "Let’s try these massages." So everybody’s clothes came off and we’re all trying these massages on each other, these sexual massages.
So it was my sister’s boyfriend, the girl, and myself. Nothing really sexually happened for the three of us, but before we knew it, it was like 7 o’clock in the morning. She jumped up, "I have class," and ran out of the room. I close the door behind her and all we have on is our underwear and I turn around and Simon is raging a full-on hard-on, like a baby’s arm. This guy played football for the Pitt Panthers. He was a quarterback, like a buck eighty-five, 6’8" – beautiful, a body made of granite. It startled me. I was trying to ignore it but he was very, very definite about what he was feeling. My skinny, track-runner legs were shaking in my shoes. I was like, "What?" And he’s dead staring at me. He tells me, "I want to fuck you." And I’m like, "Well that’s not going to happen. Hey, I don’t do that. You’re scaring me." Meanwhile, you know, I was really turned on for the first time in my life, like really turned on. There was this naked man, a male’s body, looking at me with raging hormones and beautiful muscle tone. There’s this Adonis in front of me and I’m thinking, "Well here’s my chance to actually have sex with another man." Completely negating the fact that he’s my sister’s boyfriend. I think to myself, "Who the hell will know?" I said, "OK. We can have sex but you’re not fucking me with that… that, that thing. That weapon."
He picked me up with one arm, muscles all over the place and he throws me on the mattress. He jumps on top of me, he’s grinding his body and he blows his whole load all over me. Meanwhile I was just getting started. "Oh that was good," he moans. And I’m like, "That was it?" He was like, "What?" as he’s wiping the cum off his dick. I said, "Is that it?! If that’s it I don’t want to be gay!" and I ran out of his room.
The next day I walked out of my dorm and it felt like the whole entire world knew what happened. I saw my sister and she had this look on her face, this, "I know what you did last night" look. I was like, "Bonnie, are you, uh… ready to go to class?" She was like very kind of persnickety, "Are you? Ready to go?" I was like, "What’s the matter?" "Oh, nothing. How did you sleep?" I’m like, "Oh, shit. She knows," like an intuitive thing.
I ran into the guy out at the bars a few years after we graduated. It was different. I was more mature and I understood better who I was. "What are you doing tonight?" I asked him. "I want to fuck you," he whispered in my ear. We went to his place and at that point it was five years after our first encounter. We had some really hot, hot, hot sex. I mean like deep, hot sex. He fucked me. He really fucked me. And I’m not one for getting fucked, it was just because we had that history and it was the mental turn-on that worked me up to the point to let him. It was really hot and I knew after that one time it would never happen again. He was just fucking me like he just had to do it, and he did it.
I never spoke a word about any of me and Simon with my sister. She had once mentioned to me, "You know what? I think Simon was gay all those years." I just said, "Oh, yeah? Wow. What makes you think that? I wasn’t hanging out with him… that much." And I left it at that.

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After we realized that we had done it… it was almost like she dropped a quarter. She dealt with it like it was change that dropped out of her pocket. Made me feel like an asshole and OK with it at the same time.
Vincent, 25
Burlington, VT

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