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

by Wickens, Shawn

  That’s what we had to do. We joked that maybe I was too big for her.

  ***

  With this ring, I thee wed, and with it, I bestow upon thee all the treasures of my mind, heart, and hands.

  - Traditional Wedding Vows

  ***

  Chapter 16

  "I NEVER DID IT!"

  Along the same lines as the waited-until-marriage stories, it was similarly difficult to find those who were still waiting. I can recall being a virgin and while I never had a real huge problem with it, it was something I didn't like to admit to friends. As a secret, I could live with it. It was when others found out that I felt ashamed. So I can empathize with Darren, whom I met on his 22nd birthday while he was wrestling with his own choice to abstain.

  In one instance I spoke to a college student who, not for a lack of trying, had yet to lose it because of his aversion to physical contact. At the end of the interview when I realized my faulty tape recorder only recorded a small portion of the interview, I asked if he wouldn't mind recording it again and as relief washed over his face, he politely declined and rushed away. I’m sure there were others I asked along the way who also declined to comment out of embarrassment.

  Later, while road tripping through Western Texas (perhaps geographic factors were at play or perhaps it was merely coincidence), in one evening I met three gentlemen, all in their 40s who declined doing interviews because they said they were still virgins and were too embarrassed to talk about it. I pressed each one of them, "Really? That’s a story that I'd really be interested in hearing." Each reaffirmed their virgin status but again refused.

  Unlike other major life milestones, getting a driver's license, graduation, becoming of legal drinking age, losing your "v-card" can seem beyond your control... at times unattainable. So, for all those virgins out there, you are not alone.

  SOMEONE’S WATCHING OVER

  Hailey, 24

  It was a promise I made to my grandmother. Well it was a combination of things. It was a promise I made to my grandmother when she was dying. And I just kind of said it and didn’t mean to but I never had a boyfriend before my current boyfriend where I really wanted to. Like, with all my other boyfriends, I felt really dirty. Previous boyfriends would touch me and I seriously would be sick for a week. Before Liam nobody even went "south of the border."

  My family’s Catholic but it was never like a Catholic guilt thing. It’s just a whole slew of things. I had a hard time when my father died when I was 11. I had a hard time with the "He’s always watching" thoughts that family would feed me to make me feel better. But it probably ended up messing with my head more than it helped. I made the promise to my grandmother when I was 19, only a couple years ago. My grandmother just said, "I want you to stay… until you’re married." It was something I agreed to in passing.

  But actually there’s a whole other reason now. Liam and I broke up last October. And before we broke up, I was actually going to do it… because, I loved him. But then we broke up because he cheated on me.

  There was an incident, three incidents, one girl. Anyways it’s an even bigger deal for me now. Now it’s… I just want to be sure. So often I’m like, "Uh, I could just do it." But I have such a bad sense of guilt that, once again, not Catholic, it’s just I have a really overdeveloped sense of guilt.

  So yeah, that’s it. It’s a combination of things. It’s my father, it was my grandmother, it was my family in general. We never really talked about it, but like… my sisters are all… they’ve all done it. And I’m pretty sure my cousin has too and she’s like 20.

  The strange part about it is that nobody believes me. My family all thought I was doing it with Liam the whole time. It’s not that I don’t want to. Liam thinks I have a lot of issues; pregnancy is another issue. I’m terrified of getting pregnant – terrified. I’m kind of on a path with my career now and I don’t want to screw it up by having a baby out of wedlock. I’d be kicked out of my family. So it’s a whole slew of different things, least of which is the fact that I don’t want to do it.

  Sometimes I think I’ll regret not doing it. Right after my boyfriend cheated on me I thought if I would’ve just done it he wouldn’t have had to go elsewhere. That’s crossed my mind a couple times. Plus I’ve always wanted to be the good girl.

  Sometimes he tries to convince me. He wouldn’t be human if he didn’t. He wouldn’t be a man if he didn’t. But it’s not even that I need convincing. I want to do it. And sometimes it’s the hardest thing I do to not have sex with him. There were times like right after we broke up, I was like, "Huh! I should have done it." But in the same vein if I would have done it I would have felt so guilty. There’s times where, I swear to God, I think, "What the fuck am I doing? Why don’t I just do this?" That happens a lot. He’s just a real sport for putting up with it.

  TIME TO GRADUATE

  Darren, 23

  I’m in film school, in my last year. And I’m still a virgin. I’ve had chances. There were a couple of experiences back in high school where I could have gone through with it. But I haven’t. I don’t know if it’s that I haven’t felt ready. I think it was more like I was too scared to actually go through with it. Then in one of the situations we didn’t have any kind of protection so that’s why it didn’t happen that time. But I think the main reason is because I really haven’t found anyone that I really want to take that step with.

  Twice I almost had sex with girls who I knew had gotten around and I didn’t want to be just another guy on someone’s list. I wasn’t like setting out to make a statement or anything. Nothing prideful or me being up on my horse saying I’m better than anybody or anything like that. It just never seemed right.

  It’s kind of weird being that today is my 23rd birthday, but it’s something I always think about. It makes me feel younger than everyone else in a weird kind of way. I feel more inexperienced to the world.

  My older brothers are always telling me that I just need to get it over with and it doesn’t really matter who I have my first time with. But I don’t really feel that it’s something that anyone should just get rid of. I’m aware that by dedicating myself to finding someone special that I’m just pushing it farther and farther away. And I don’t know that I feel bad that I’m pushing it farther away. A part of me can’t help but feel a little frustrated, but I don’t know if that’s my own feelings or if it’s society dictating those feelings on me. I can’t say that yet for sure and I’d like to say it doesn’t really affect me, that I don’t feel different, but of course I do. It just seems that 23 is kind of an old age to be a virgin these days.

  I’ve talked about this with only a very few girls. There’s currently this one girl that I’ve some interest in. She’s 18 so she’s feels significantly younger than I am but she’s already been with five guys. I want to feel like I’m more mature and older than her, but in that one regard she’s totally got the upper hand. It’s intimidating, it’s definitely intimidating. Ideally I’d like to find someone who is a virgin too but at this point I’m not about to limit myself.

  My brothers think I’m being girl-like for doing it this way, but that’s the way it has to be. I guess I just have to wait it out because I’ve already gotten myself into this trend of not settling for just any girl, so I think I’m going to have to stick with that. I may be 30 when it finally happens. Who knows?

  FOR REAL THIS TIME

  Marius, 28

  My wife, my soul mate, had been with five guys before me. We’ve been together five years and I kid you not, I just popped her cherry three weeks ago. It wasn’t in the normal spot. It was up high on the top wall. I fucking nailed it and it said, "Boom," the hymen split. That hymen is fucking smashed.

  DID I OR DIDN’T I

  Karen, 18

  I’m still a virgin, still flying the ‘V’. I told myself that I wanted to wait for somebody I really cared about or at least liked. Technically I guess I did lose my virginity because, well, I knew this guy named Kai, and he was real
ly cool and I thought he was really hot and he said he wanted to fuck me. I was like, "Oh, whatever." I was 17 at the time and he didn't know it.

  Anyway he wanted to fuck me and I got really drunk one night and I was like, "Fine let's do it." I went over to his apartment and the two of us are naked. He did penetrate and then he stopped and was like, "I can’t do it," because I had told him my morals about how I wanted someone I cared about or loved or whatever. Like I don't care about premarital sex; that's not a big deal. I just wanted somebody that I cared about, but I was drunk and I was like, "I need to lose this shit eventually, right? Let’s go for it." So he was in, and he was out, and then, "I can't do it, I can't do it." And I was like, "Fuck you dude, that's fucking lame. Don't tease me!" So I started sucking him off. That got him excited again and he was getting all manly like, "Oh my god, I totally want to fuck you." And I was like, "Then fuck me!" You know, shit dude. Don't fucking play me. He goes in again and then he was like, "I can't do it, I can't do it." And he pulls out again. All because of something I once said about wanting it to be about love and something intimate.

  I only knew the guy for a short period and I think he got freaked out because he figured I would get really attached or whatever. And I'm so fucking sick of guys saying they're afraid I'm going to get attached. Get the fuck over it. All right, I do have a tendency to get attached, but once I realize where we are, you know, it's different. As soon as somebody tells me they just want to be my friend and let's just mess around then I'll be like, "OK." So I guess technically I'm not a virgin, but I don't count it and I’m sure sex feels a lot different than some guy just poking his dick inside. I need to stop telling people that I have these fucking morals and just fuck somebody.

  I'm not going to just fuck any bum that comes along. But I've been waiting for so long for love and it doesn't even exist anymore. I talk to people who say they don’t date so they can be with whoever they want. Nobody really cares about love anymore. I always had these optimistic ideals about how sex could be about love and intimacy and it just doesn't really exist anymore. Like, barely.

  Chapter 17

  "THE OTHER SIDE: TAKING VIRGINITY"

  After a whole year into the interview collection process I realized I should also be asking people if, subsequent to their own first time, they have taken anyone else's virginity. And the revelation came to me after a man in New York had said his first time was boring but when he "popped some other girl’s cherry," that was all the more memorable.

  When I began asking this follow-up question, a common response from both men and women was, "I wish." It's a common human need, wanting to be remembered. And it takes a special person to be remembered as the best but far less effort to be remembered as the first; one that just has to show up, albeit before everyone else, to be that coveted "his first" or "her first."

  I don't know what's at the root of this drive to be the person to usher someone into their new sexual life. Some of it is well-intentioned, wanting to provide a good experience. Some of it is out of selfishness, a way to assert dominance or power over another person. And perhaps in some cases, it’s wanting to relive that first experience as a way to erase one’s own lackluster loss of virginity or, as expressed in Madonna's first #1 hit single, "Like a virgin, touched for the very first time," to relive that exciting first moment.

  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 t
o 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...