How to Lose Your Virginity ...and how not to (Real Stories about the First Time)

by Wickens, Shawn

  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 break-up 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?

  It all seemed ironed over but then the next week her parents told her she couldn't stay at their house any longer. I have an apartment above my restaurant so I said, "Lindsey, why don't you stay at my apartment? You can stay there." The next weekend after that, I was over at my own place and she came over because again, her parents kicked her out. So I said, "Come up." I really didn't think anything of it. We watched Young Guns, but really didn't watch that much of it whatsoever. We didn't do anything, we were just talking to each other and she's telling me everything about what's going on in her life with school and all of her friends. I just listened to everything she had to say and the movie went by real fast.

  I was 35, almost 36. She was 20. At that point in time I just thought of her as a really great friend. Another week goes by and she's at her parents’ house and everything sounds fine and then the next weekend she says they're not going to let her stay. During that time there was an oven explosion in my restaurant and so the whole side of my face was burned and my ex-wife couldn't even care less, made no effort to do anything for me... and I could have died.

  So I was in the hospital, got morphine and everything. Lindsey and I hung out so another week goes by and once again she can't stay at her parents’ place so I let her stay at the apartment. The only thing is, I'm going to be there too since I was laid up from the accident. So we're sleeping together, it's a king-sized bed, plenty of room. She asked me for a massage, which I’m actually in school for massage so the request itself was nothing out of line. I give her a massage and again I had no intention of anything and went to sleep. Then in the middle of the night she woke up and she told me that she always had a crush on me and she wanted to know if I found her attractive and, "Yeah, you're beautiful." We kissed for a while.

  It felt a little weird being on the opposite side of the age thing. I told her there was a big difference in experience. And her at 20 I figured she could have only been with a couple of people at that point and whether I should have only been with a couple people well... I'd been with a lot of people. She told me that she’d only slept with one person. I was like, "OK. I understand that, but there's a difference between a high school-aged boy or a college-aged boy and a man who's slept with as many women as I have."

  So we didn't do anything, we kissed, we held each other. I told her that I love being with her. We had a great time. The next weekend was my birthday. I turned 36 and she came up to Portland, Maine, with me and we spent the night together. And that was the first time I made love to her and it was obvious to me that the one guy she'd been with really didn't know what he was doing. Later I found out that she really had never slept with anybody. She had gone down on guys, they'd gone down on her but nothing else ever happened.

  And we made love for hours and it was enjoyable for her. It was enjoyable for me. I had a wonderful time making love to her. And she is an incredible lover, but the thing is, it took a long time building up to the point where almost a month from the first time we really admitted to having a sexual attraction for one another to the point where we had sex for the first time. I mean we had done a lot more, we had kissed and touched each other, played with each other. There was a lot of intimacy that led up to it which, for me I think, it was like I can give you something as opposed to, you know a 12 or 13-year-old girl having sex with a 13-year-old kid and neither of them knowing what the hell to do. But for my first I had a woman show me exactly what was supposed to happen. So I knew how to show this young woman.

  We’re still together, but the hardest part now is that I kind of want her to experience other possibilities. That’s a difficult position for me to be in. I was the first guy that she ever was with and, oral sex, whatever anyone wants to say, I mean, Bill Clinton was right in that aspect that it's really not sex. It's sex but it's not sex. And for someone like myself who's been around and seen what the whole world of sex has to offer... I can give her me but I can't give what everyone else gave me. It's hard.

  ***

  I would never again want to take someone else's virginity…

  I felt very terrible about it. It wasn't a good experience for her and I just wanted it to end. It wasn't sexually turning me on because it was hurting someone that I felt for.

  Randall, 22

  Houston, TX

  ***

  Chapter 18

  "I DID IT MY WAY"

  Though most of my road trips for this book were solo trips, they felt more purposeful than any other vacation I’ve taken because I had a specific purpose for traveling instead of sightseeing. And I feel an analogy can be drawn between my positive travel experiences with some people’s good first times – if you set out to lose it, just get it over with, that’s most likely exactly what it will feel like. But when approached as, "I’ve given it some thought, this is who I am, and this is how it will best work for me," "I’m finally going to discover the mystery that is sex," "Here it is, the beautiful act that inspires some people to compose songs, write sonnets, paint or sculpt the human form," "I will need training wheels at first but I’m still going to enjoy it," the experience ultimately benefits. Journeys with intent illicit better results than just going through the motions. How you see it is what you’ll get out of it. And while we may not have as much control over when it happens as we may like, we do have control over our attitudes towards it. That not only applies to the first time, but every time.

  One aspect of these interviews I didn't expect to find was individuals who knew what they wanted, knew how they wanted it to go down, made a choice and went after it. In these instances, I've found those who defined the parameters of losing their virginity had more positive experiences. Confidence breeds success. Knowledge is power.

  ON MY TERMS

  Rebecca, 38

  We met these guys dragging in Douglass, Kansas, which was where the closest drag strip to Wichita was at the time. I just woke up that day knowing that I was going to do it and it was simply a matter of finding a stranger. Virginity to me was a power thing. I didn’t want any of the guys I knew to have that much power over me so a girlfriend and I picked up a couple of guys to have sex with, which nowadays is stupid.

  We were all driving around, flirting, hanging out of the cars and we ended up out in the country, right in the middle of an oilfield, right next to the pumps. As those oil pumps were moving, so was I. He was a complete stranger, it was happening there and then because it was my choice. My way, my time. My friend had already lost hers at like 14 or 15.

  I never gave in to peer pressure or anything like that, and sex at the time wasn’t a big issue to me. I was 18; I was going away to college. It was more of a control thing. Other things were happening at that time that were beyond my control. My parents were getting divorced and their separation was a loss of control, a loss of what I knew. Losing my virginity in this manner was purely a way of controlling what I could – the how, the when, the what and the where… with some guy whose name I do in fact still remember. So it was a very conscious, non- emotional choice. The love thing wasn’t important to me. I was watching my parents fall apart so love wasn’t the issue. It was control.

  There was a lot happening then. I was going away to college and a lot of my friends were staying in a small town, getting married. I didn’t want that. I left town and went to college and did it all my way.

  ELECTORAL VOTES: 286 TO 251

  Lana, 18

  I met him at a protest march for peace around a year before I ever started dating him. Then afterwards there was a show put on by the local S.P.A.R. organization, Skinheads and Punks Against Racism, at this American Legion hall right outside Philadelphia. Eve
ryone went to the show after the rally.

  I’m not really sure when I decided he was the one because he was tall and very muscular; me – I like lean guys like around 130 lbs. But he’s really an awesome guy and had a lot of respectable views on the world and actually followed through with being active on achieving goals and stuff. So I was attracted to the fact that he was ambitious and going to school for what he wanted to do. And punks aren’t usually the most ambitious types, but he was a nursing major at Drexel which I thought was productive. We dated for about a month and then came Election Day for the 2004 Presidential Race.

  I wanted to have something beautiful to look back and remember other then Bush getting reelected – one good memory before everything just went completely downhill. It went down in a Drexel dorm room. I didn’t go into it thinking it was going to be amazing or anything. I just wanted it to become a good memory. Aside from it being in a Drexel dorm room, ‘cause what’s grosser than having sex in a dorm room, it didn’t really change the relationship any. I had waited awhile and we had known each other for so long. Then later that day, of course we found out that Bush was reelected. But I still have that nice memory, which is awesome and exactly what I wanted.

  It was pretty weird because the whole thing was planned and most people don’t plan out that type of thing. He was actually really unsure about whether or not he wanted to be my first because it wasn’t his first. I told him I was ready and that I wanted to do it on Election Day because we were going to hang out that day anyway and it was just to have one day together as crazy youth before the election. After we finished he asked me if I was OK, then we cuddled and fell asleep.