How to Lose Your Virginity ...And How Not To (27 page)

IN MORE WAYS THAN ONE
Holly, 38
After college I lived in San Diego for a summer and I met a younger guy who, like me, was a redhead. A very artistic and interesting guy. I don’t know how we met but he was just a really sweet guy and so we started dating.
Everybody thought we were brother and sister because we both had red hair. Somehow I learned the fact he was a virgin so one day we just ended up on his father’s boat as it was docked, in the little cabin down below. It was nice because the boat was moving and it was just a really romantic and nice. It was special for him, I’m sure, and I hope that the subsequent times he was on that boat that he thought back on that first time.
He was definitely better than my first time, the guy I did it with my freshman year of college. This San Diego guy just had a lot more sexual energy about him. He was a redhead, after all. And I think the fact that I was older… added some excitement for him.
It wasn’t like a big love affair or anything. He didn’t fall in love with me after that. Being that he was younger, I thought maybe he would. But he lived in San Diego and I was living in Chicago at the time. I gave him my car when I left, a piece of shit 1979, white Mazda RX-7. I think he got just a few hundred dollars for it from his brother who bought it from him. I said he should use the money to come visit me. I guess that entitled us to one more romp. He had never been out of San Diego his entire life so not only did I devirginize, him but I allowed for him to leave his home turf and visit me in Chicago. I got to devirginize him in more ways than one.
NO PRESSURE
Justin, 23
I just recently went through a breakup and I feel shitty talking about it, but I took her virginity. It was a very serious relationship. We had been friends for a long time and I even felt worse than the time I lost my virginity with someone since there’s no way it could have been mutual. I had more experience so at that point it was really just all about her.
She had vaguely entertained the notion of waiting until she got married. I absolutely didn’t pressure it, but there was the unavoidable larger arc of it where, obviously I’m interested in sex so invariably that alone is pressure. I offered slowing down and staying friends because if it’s not going to be a sexual relationship, ‘cause really that’s what separates a real relationship from a friendship, then it would have been best to just stay friends. But we ended up deciding and she decided that that’s what she wanted. So six months into the relationship I took her virginity. And that feeling of taking something, that irreversible taking… it was 10 times worse than when I lost mine. I was interested in sex and there’s no way that that wasn’t pressure on her.
Afterwards we were together for about a year before we mutually broke it off. I tried to get back together with her but she refused. During the breakup she even brought up the fact that I took her virginity. I had never felt so guilty.
THE SLOW SEDUCTION
Cliff L, 39
CLIFF L: Let me tell you about Veronica. When I was in college I met a beautiful girl named Veronica. She was the prototypical petite chick – 110 lbs., cute, innocent... came in from a little town. And the way that I met her is that I used to work at the little campus radio station at U of L and when women would walk by our window, I'd be obnoxious and wave them into the radio station. I waved Veronica in and when I saw this girl, I really liked her. She had this sort of an innocence, but sort of an energy. You know how sometimes you can look at a woman and can feel that she has a passion but... it's not been realized.
SHAWN WICKENS: Sure.
CL: Yeah, they're absolutely wonderful. They're sort of the librarian types, the academic types. But you can tell that they're just out of control if they get the right stimulus. Well, the way I first met this woman is that I invited her to come in and I told her that we were going to do the balance test. The balance test consisted of her sitting on my knee, and balancing. I had just met this woman seconds before and I balanced her on my knee.
SW: This was on air?
CL: On air. And one of the things I noticed very quickly was that when she balanced on my knee she spread her thighs. It turns out that she had horses growing up. So this was familiar to her. And I knew that I had something special. The thing though was that this girl was just so innocent that I couldn't bring myself to just take advantage of her. And I wasn't really sure that she was the right girl. So what I did basically was I teased this girl sexually for about six months, to make her beg. One evening in particular... I had her in her dorm room and had her stand up next to her bed and I had the silk scarf and she was wearing a little teddy and I rubbed a silk scarf back and forth between her legs and told her to beg for me to please, please, please. And she was just so passionate.
She was one of those girls that just... you know, touching them anywhere, her belly or her thigh, wherever... I got her crying, begging me please to take her. And instead I only put my finger inside her and made her cum, cum, cum again.
Long story, short. All of the other guys really, really wanted this girl. She was the girl that they just had to have, but I couldn't bring myself to take her because she was just too innocent. So I teased her for a long time and at the end I told her we couldn't date because I met a girl who was more sophisticated. I ran into her a year later. Beautiful, and still a virgin.
SW: And still innocent.
CL: I'm in the projection booth at the Red Barn Theater on campus. I was running the film. She came up and I hadn't seen her in a long time. We talked, it was really great. She was wearing a little miniskirt and she came out of nowhere, real strong. She sat on my knee, the same way she had at the radio station. So... we're in the projection booth, it's a year later. I had rejected this girl in relationships because I thought she's just not really emotionally mature enough. And she comes in and she has come for a purpose. She's wearing a little miniskirt...
SW: And she knew that you worked there.
CL: Yeah, yeah. We had spent some time there before. We had made out there. I had teased her there many a time. One of her favorite things was to stand when the theater was darkened... I would stand her looking out over the theater while the lights were out and I would finger her in the dark with the crowd down below.
So she came in and she was wearing a miniskirt and she wasn't wearing anything underneath it. And I hadn't seen this girl in awhile. So she came with a purpose. She came to make me take her. And I felt really, really, really guilty about it because, you know, but... she wanted it so badly she begged for me to please do it.
As she sat there in the chair, I fingered her. And it was so good she just reacted so much. Every tiny little touch of my finger meant so much to her. I took her to my home and we made love for about five hours. You know how when you first, that first tenuous... and there was this amazing sensation when I finally let my penis go inside her she like, gave up everything to me. And somehow when she gave up everything to me I lost all respect for her, and for who she was.
SW: Her innocence was gone.
CL: It made her seem less to me. And she was so sincerely, so sincerely in love with me, but only for the sexuality and the power that it brought to her. It broke my heart. We continued a relationship for a couple of months after that, lots of hot sex that, you know, took it to a higher and higher level, but there was no place for it to go emotionally except the sexuality. And it absolutely broke my heart the day that I had to tell her I didn't want to see her anymore because it was only about the sex.
SW: Right.
CL: And wherever she is today, someday I'll see her again, I'd like her to know that I really, really, really did care about her. And I was only trying to protect her.
SW: Did she, sort of when you told her, did she understand?
CL: No she didn't. She sent me letters and she... started… actually she went kind of nuts. She started exhibiting all sorts of really odd behavior – writing strange notes to herself and leaving them as though I had left them. Went completely off the end. Now... one thing that all really shallow men know is that there's nothing hotter than a psycho chick.
SW: Than a what?
CL: A psycho chick. Only truly shallow men can admit this, and I am one – I must be for this story. And the fact that she loved me so much and I didn't love her, it gave me a kind of a power over her that I hated myself for feeling. But I loved the power. In the end, the way that I finally solved it was I invited another girl over and created a situation where the three of us had sex. And it was very clear that she was just another girl being used. I used her horribly sexually. Held her face down and physically used her face and then used the other girl in the same way. And that was how she knew that it really didn't mean anything to me.
SW: Yeah.
CL: I feel so horribly to this day. This is fifteen years ago and I still can barely forgive myself.
SW: I appreciate you sharing your story.
CL: It's nice to let that one go.
CHECK THAT OFF THE LIST
Katey, 23
I was at an Ohio University Halloween party my freshman year and I met this guy dressed up as Fozzie Bear. I didn’t feel like dressing up that year; I was a librarian, I carried a book around.
Steven was very cute, a little outdoorsy guy – kind of emo, kind of indie-rock. I make out with him that night. I don’t see him again for eight months, run into him again and we make out again. No big deal.
Three years pass and it’s three days before my graduation. I had a list of things to do before graduation: sex in the art building, sex in the library, sex on the 50-yard line, and also to take someone’s virginity. I ran into Steven again after all these years and my boyfriend is conveniently out of town so I proceed to take Steven home. He was a 23-year-old virgin. He was saving it for somebody he loved. And I’m just that hot, I convinced him not to wait any longer. I think I might have given him a blowjob, which is really funny ‘cause I never give people blowjobs. I had to teach him how to put a condom on. Someone had to, the boy didn’t know. It was very entertaining to me.
Every time he was about to cum he thought he had to pee, not understanding what it felt like to cum from sex. In the morning we woke up around 8 o’clock and he’s like, "Oh, I’m so glad I lost it to you. You’re so amazing." I was like, "Can I say something without it being rude? You need to leave because my boyfriend is coming back to town today." I kick Steven out and I broke up with my boyfriend 12 hours later. During the breakup I told him I slept with somebody because I was mad at him because I found out he had decided he was going to move to California.
But the guy was 23 and waiting and I totally turned him. I call that one my ace of spades V-card.
ANATOMY LESSON
Simon, 31
I was in the seventh grade and I took this girl’s virginity. She was the most popular girl in the school and she was in my garage. I wasn’t a virgin, she was. I had her in my garage and I promised her it wouldn’t hurt. I told her it would be all good. She never had anything up inside of her, but she was the most popular girl in school, so you know I felt I had to tap that.
But I put it in her ass. I had her bent over the workbench and I put it in her ass. She’s like, "Oh, it hurts. It hurts." I was like, "It’s supposed to feel that way." So I was fucking her in her ass for about 10 or 15 minutes. I was fucking her real hard and I cummed up inside her. She was like, "Ughhh…" She put on her pants and went home.
The funniest thing is I took her virginity twice in one week. A week later she comes over and says she wants to fuck again. I took her to my bed, I’m fucking her in her pussy and she said, "It’s in my ass! It’s in my ass! Take it out!" I said, "It’s supposed to feel that way."
She thought it was in her pussy when it was in her ass, and then she thought it was in her ass when it was in her pussy. I got her all mixed up.
THE FIRST ONE’S FREE THEN THEY COME BACK FOR MORE
Guillermo, 33
In college, I was a junior and this girl was a freshman and I could tell that she liked me but I would never have sex with her, get intimate with her because I felt like since she was a virgin I would hate to be the one to spoil it for her. I guess her hanging around and me being horny one night led to me making a move on her. We were the party guys on campus so a lot of underclassmen looked up to us ‘cause we always had a party going on. And I happened to leave my door open all the time. And I remember, I came out my shower with a towel on and she happened to be sitting in the room, which was nothing un-normal. It was like that all the time, people just hanging out in the party room. And now that I think about it I probably did her wrong. As I think about it I remember I called four or five other girls to come over to visit me while she was there. I think I lost the towel after the third phone call. And no one else could come over and I kind of looked at her like, "You’re here and I'm here... if you won't scream I won't holler." And she didn't leave so I figured it was the right opportunity. Long story short I ended up hurting her heart. And she ended up becoming one of the biggest freaks on campus. So do I get props for that? Do I get a high five? I would think about five or six other guys on campus owe me a high five for that one there. I made her. That's sad I talk like that. And my dad’s a minister. That is so sad. But it’s kind of like the dope dealer thing. If they didn’t buy the dope from me they would've bought it from somebody else, I guess... don't make it right though.
THE STUDENT BECOMES THE TEACHER
Emil, 36
She worked for me in my restaurant in Maine. We always got along together. She's a beautiful young woman. I was with an older woman for my first time so it's ironic the way this all turned out.
Her and I would always tease each other, play games, and one day it was like, "Why don't you just run away with me..." joking like that. A couple months go by and we continue playing that game, flirting with each other. She has an incredible smile. Then on her birthday, the 12th of July, her parents didn't even say "happy birthday" to her. That upset me. I thought OK I have to do something for her because I really like her, she's a great employee. A friend of mine is a jeweler so I had him make these beautiful earrings for her. No expectations whatsoever except for, she should just be given a gift. You know, how could your parents forget you on your birthday?