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

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How to Lose Your Virginity ...and how not to (Real Stories about the First Time) Page 3

by Wickens, Shawn

Kumamoto, Japan

  ***

  PHANTOM SHOPPER

  Patrick, 25

  This was in Hillsboro, New Jersey. We were in marching band together. She was in the color guard and I played trumpet. She was a year older than me and I was a freshman. It was that classic "I loved her at first sight" kind of thing – my first real infatuation.

  We eventually started dating and by the end of my sophomore year I was anxious to lose mine. She was kind of hesitant about it since she lost hers a couple years before.

  But I kept working on her and around the time I thought something was close to happening, and this is the best part of the story: I was with my younger brother who was in eighth grade and we were driving down the main route in town. I pulled into the local pharmacy and I was like, "Little brother, you got to do me a favor. I need you to go in there and buy me condoms." I wasn’t about to do it myself – I had a little brother here to do it for me.

  He actually had no problem with it. You know, little brother – big brother kind of thing, a good little brother deed. So he goes in, and I waited in the car the whole time. He comes out and says, "Pat, you’re not going to believe what just happened." I was like, "What did you get ‘em?" He said, "Oh, I got ‘em. And I turned around and my religion teacher was in line right behind me." She didn’t say anything, just gave him the look. He wasn’t mad about it, I think in a way he appreciated the experience – buying condoms for his older brother and getting caught by his religious studies teacher.

  Then later that week I went over to her house, condoms in hand, and she said, "Yeah, tonight’s the night," so of course I was a nervous wreck. I didn’t tell her the story about my brother, she probably would have made me wait a few more months as punishment. Like I said I was nervous because she already lost her virginity. I was fumbling for awhile and it was your basic American Pie kind of thing. We were just making out for awhile and then she was absolutely silent for the rest of our sexual experience. She really wasn’t into it. A very "laid there" type of girl.

  She comforted me a bit because I honestly lasted like 60 seconds. I was like, "I’m sorry. Was it OK?" She was like, "It’s OK, Pat. It was all right." I think my brother eventually asked me if the condoms were the right kind. I said, "I guess. I don’t know." So having my little brother buy the condoms was the best part of the whole story. It opened him up pretty early to the idea of buying condoms.

  BY THE BOOK

  Nora, 30

  I was a senior in high school and I was about to graduate when I met this older guy through a friend who was dating a friend of his. He was 23 years old. We hooked up and just drank, nothing intellectual, just a party scene. I had been a real advocate of using condoms and I was the one who always told my friends, "Don't get sick." At 15, 16 years old I was abstaining but all the while passing out condoms to my sexually active friends.

  My mother was a child psychologist so from an early age she told me pretty much everything that could go wrong with sex. Not so much go wrong with it but all of the ramifications of being unsafe about it. The one thing she didn't warn me about was older guys. But I kind of had my mind made up that I wanted to get it over with. All my friends had lost their virginity and I just wanted to get it done. It wasn't something that was supposed to be romantic. It was like driving for the first time when you get your license. At some point you have sex.

  So I guess I had known this guy for a week and we did it. I told him it was my first time and I insisted that he wore a condom, which he was not happy about. It wasn't fun at all, it was painful. He was unrelenting about how un-sexual I was. But it being my first time, I didn’t know how to be sexual. I didn't have an orgasm but at least it was "mission accomplished".

  He was enormous. He was huge and it hurt like hell and it wasn't fun. And everything you hear about big dicks being great, nope. They're not. They’re hell.

  I don't regret it not being like an intimate moment. I was glad that I did use a condom because a lot of my friends were pregnant, like three out of five of my friends were pregnant by 17. I had tried giving safe sex advice to all my friends but some of them just didn't understand the importance or had the concept of being careful.

  ***

  Like six in the morning and I was sleeping and my parents unlocked my door and snuck in. At first I thought it was a dream, but I woke up to my parents rapping about anti-sex or like safe sex and the importance of using condoms. My mom and dad were wearing backwards hats, my dad had his arms crossed like Run DMC and was beatboxing. My mom had this crib sheet she was rapping off of. It was something ridiculous like, "We love you son. Don’t be dumb. If you have sex, use a condom."

  Kevin, 22

  Atlantic City, NJ

  ***

  THE PRESENT

  Bud, 27

  I still have this leather wallet that I’ve had for about 10 years now. I got it when I was 17. This would have been the semester before I graduated from high school – so I guess like the fall semester of my senior year.

  I had a girlfriend and we hadn’t had sex but we’d been dating for awhile. I wanted to have sex really bad and she was hesitant. Then as sort of an early graduation present she gave me a wallet and it was weird to get a wallet as a graduation present. I was thinking well that’s nice. Then she told me, "But there’s more to it. Look inside." I opened the wallet and she had put a condom inside it, which was her way of saying that we could have sex.

  It was funny, it wasn’t very sexy but more just comic and funny because we were both, "Oh, I don’t really know what to do." Neither of us were more of the "expert" than the other, which was good. I just remember it as being funny and like it’s the only time you were allowed to laugh that much while having sex and it be OK. After that you’re supposed to get more sophisticated. You know, you’re not really allowed to laugh that much, especially when you’re having sex with someone new for the first time. For some unspoken reason it has to be deadly serious or it has to somehow be really passionate. But for the very first time it was OK to laugh because there was no expectation that anybody would really know what they were doing. That made it better, I think. It made it more relaxed.

  I can remember, with that girl, later on having sex seven times in one night. Nothing like that has ever happened to me after that. And I think the reason is that you were able to be funny and have fun when you’re new to it. There was nothing really riding on it so it was more like both people were able to see it as something cute or fun.

  SCAVENGER HUNT

  Aaron, 27

  I went to an all-boys boarding school in Virginia and I met a girl my senior year who went to an all-girls boarding school about two hours south of me. We continued to date after I started college, still having not slept together. So I was in college, and I would go and visit her some weekends and it happened that her roommate's family lived in the town where this boarding school was. When I would go to visit her, her roommate's family let me stay with them. We had been talking about, you know, sleeping together, and etcetera and there was one particular night where her roommate's family signed her off of campus and we went back to her roommate's house and the family was away. We were left alone in the house.

  We sort of agreed, "OK, well... we’ll make love tonight if we can find a condom in the house." So the two of us scoured the entire place and it took about two hours. We went through everything, the mom's underwear drawer, the whole nine yards and we're not finding one. After about two hours of searching we were in her roommate's younger brother's room and we find a suitcase under his bed filled with about five or six porn videos, a bunch of dirty magazines, and a full box of condoms. That was when I lost my virginity, my freshman year of college when we basically stole a condom.

  We were there for the night by ourselves so it was actually really beautiful. It was great.

  ***

  We were so nervous about throwing away the condom in her dad's garbage that we went out about a half a mile from her house into the woods, dug a hole a
nd buried the condom. We buried it like a foot deep, like we were burying a body in The Sopranos or something.

  Art, 27

  Washington D.C.

  ***

  60, 59, 58, 57, 56…

  Melanie, 24

  I was a late bloomer, 21 years old. Doug and I were members of the same co-ed, community service fraternity. After our friendship transitioned rather smoothly into a relationship, we found out that both of us were still virgins.

  Eight months into us dating we had that ridiculous talk… "Um, I guess we’re going to have sex sometime." But I was all, "I’m not ready!" And he’s like, "Neither am I!" He was a year older than me and when he graduated he moved to an apartment and I’d leave school to visit him on weekends.

  The first time it almost happened he had guests and we thought, "Oh, we can’t do it because Linda and Don are on the other side of the door. Oh no." He also said he didn’t have any condoms and I told him, "Yeah, you’re not having any sex without any condoms." When I got back to school I went to the health center where they handed out the free ones and I pretended to be an R.A. saying I needed condoms for my entire floor. I scored a box of 60.

  That next weekend we finally did it and we counted backwards from 60. So the first condom was 60 and then the next time it was like, "Better get number 59." That morning after, he took me out for a breakfast at McDonald’s because I really liked McDonald’s breakfasts. He probably thought I was such a cheap date.

  I still have some of those first box of condoms. We broke up before he and I could count all the way down to condom number one. But that’s when it happened. At the time we were in a loving and committed relationship and it was a really good experience.

  Chapter 3

  "PENIS IS THE PROPER WORD… VULVA IS THE PROPER WORD."

  The above quote is taken from a sexual educational video – a free rental that my mother forced me to watch when I was 12. I unwillingly sat through the VHS puberty lesson and a folk singer appeared on the screen, sitting in a playground and strumming a miniature guitar while singing a song about the proper names for the male and female anatomy. I, in turn, took that song back to school where it became an in-joke amongst my friends: penis is the proper word - vulva is the proper word.

  In sexual education there was the tendency to laugh at the situation, vocabulary words, etc. But when presented with the real thing in the bedroom, fear and apprehension is a far more common response than laughter. As much as you can try to prepare with book smarts, there is no substitute for hands-on experience.

  This next collection of stories represents a heightened sense of awareness about the workings of the opposite sex, or sex in general, as a result of the first time. Lessons learned about who they were, what they liked, what they didn’t like, what to do, and what not to do.

  STUDYING A "BROAD"

  George, 24

  I was going to school in London. I was dating a girl, my first girlfriend, who wouldn't sleep with me. She was back in the States. We broke up over the phone and that same night I met a girl from Denmark.

  Europeans do things differently; they’re more open about sex. Her being from Denmark and me being from the U.S., we knew that we weren't going to be in the same place for very long. We had sex three times and then she left the country. That was it. I still keep in contact with her, email every so often.

  It was interesting because I kind of assumed that the way I would lose it is that a girl would finally say, "Let's have sex." I learned that's not the way things happen. I initiated and she said, "Sure." That's how I've been doing it ever since. Guys have to initiate.

  THE GAME

  Anthony, 23

  All right. The time when I lost my virginity was Dec. 24th, 1998. I was a spring chicken. A fresh boy straight out of the coop. And it was a black piece of pussy that just had my name on it. She was smokin’.

  I was the ever-present wingman for one of my friends going out with her. So I was the personality, he was the physicality. And finally I just talked the bitch into it. She dropped him and then went for me. You got to trick a girl. The way to get pussy is to trick a bitch. Trick a bitch! Basically I’ve been tricking girls ever since I got my first piece of ass and I will remain tricking girls until I find a woman who is right for me. I will tell them what I have to tell them to get them in the sack.

  You can be a fat, nothing, white kid who really has no business getting any butt, or you can get a lot of ass if you act like the number one stud. And you always do this, that’s how you should always think and act. So when a girl comes up to you and wants to have sex with you don’t look surprised, even though she could be hot and you’re a slob. You just go with it and that’s how you trick it.

  So a little, chubby white boy like myself didn’t know what I was in for. She came by and we made passionate love under the Christmas tree until my mother came home. My mother walked in the house and found us both half naked so it of course broke up the proceedings. But that is the story of how I, a little white boy with jungle fever, lost my virginity.

  Look,the fact of the matter is, if you really want to get what you want, you gotta trick them. Trick them into thinking you’re sweet and nice. Because if you tell them the truth, she ain’t gonna want your ass. You’re really not that ill, just remember that. If you’re not tricking her, then you’re gettin’ tricked.

  ***

  Losing your virginity is the worst for girls. For guys it's like heaven.

  Lisa, 30

  Austin, TX

  ***

  RANDOM BOYS

  Vanessa, 25

  A couple days after my 13th birthday, I was at the mall with my best friend. This guy came up to me and said, "You’re cute. What’s your number?" Being that I was young and insecure, something as simple as a guy asking for my number made me feel cool, I gave it to him. He was older, maybe 20. I told him I was 17. Whether or not he believed me, he was like, "Come over to my house."

  My friend and I got into his car and she and I pretty much knew what was going to happen once we got there. I started to prepare myself for the inevitable because I knew once I got to his house it would be too late to back down.

  I never said I didn’t want to do it, so it happened up in his bed. My friend and one of his friends did it in another room. That’s how we knew it was kind of a set-up, because some other guy was already there waiting for us. Getting us girls there was a plan and it felt like a plan. That sucks when it’s your first experience.

  I was a 13-year-old insecure little girl who felt fat and ugly. He was the first guy who ever asked for my phone number so when he first came up to me I felt pretty special. After it happened, I didn’t feel special at all. These guys wouldn’t even go out of their way to drop us off. We had to take the bus. The whole bus ride home my friend and I talked about it, about how neither of us liked it, neither of us thought it felt good. It wasn’t the right way. It wasn’t right at all. It wasn’t right until four years later when I dated my first serious boyfriend.

  I learned a lot from that experience though. It was my first introduction into the male mind and I learned to forever avoid going over random boys’ houses.

  ***

  I gave her a call three weeks later. I wasn't in San Francisco anymore, but I was willing to go back to meet her. I don't think she appreciated that very much so I've learned that one of the hardest things for a guy is knowing when to call back afterwards if you want to hook up again. I can say that three weeks is definitely too long.

  Gary, 26

  Brissie, Australia

  ***

  THE HETEROSEXUAL LITMUS TEST

  Betsy, 19

  I like guys and girls but I was trying to decide which I liked more. I was kind of more into girls but I came from a real Mormon family. They kind of know I’m gay now but it’s unspoken. It’s not admitted. So I was going to give it one last shot to see if I could settle down with a guy before I dated girls full-time and cause a family upheaval. Basically I had sex with
a guy to find out how straight or not I was, and it helped me figure out that I wasn’t.

  I met this guy at a random party. I was kind of into him, kind of not, and we started dating casually. One night we go to this concert and he has some ecstasy so we eat a bunch of X. We spend all night rolling together. Next morning we woke up and I thought, "OK. What the fuck? Let’s see how this works." I tried and I didn’t get off. We dated for another four weeks and I just never got into it.

  Matt always wanted to have sex in the morning. It was hard to go through because I could see him and all his manliness and it bothered me. I couldn’t turn off the lights and pretend he was a girl. He ended up dumping me and I was upset for about two days and then felt relieved because I was free to date women.

  I did like Matt; I cared about him as a person. He was awesome and we had a lot in common. He was a pianist and I play the piano too. I fell in love with the boy on an emotional and intellectual level. Physically… the sex was not as enjoyable as it should be.

  The whole complex of losing your virginity after growing up in a Mormon household is built up a lot. Mormons actually call premarital sex the worst sin second to murder. So in the hierarchy of sin, you can murder someone and then the next worst thing you can do after that is have sex outside of marriage. So yeah, it’s a huge deal. After I lost it, it didn’t seem like a big deal at all. It helped me figure out what sex is really about. Like sex can’t be about the relationship or about getting them to like you. Sex has to be about how you feel about them. And it appears I can only feel that way about other girls.

 

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