How to Lose Your Virginity ...And How Not To (4 page)

***

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.

***

I'm glad it wasn't an American Pie-esque exchange of, "I love you" for having sex. I somehow managed to say, "I love you" a few weeks after having sex. I wouldn't have minded saying, "I love you" earlier; it was just very important to me that those two events not happen at the same time, because I felt like it would have been some sort of bizarre prostitution of exchanging one thing for the other.
Drew, 21
Metuchen, NJ

***

THE MOVE
Roy, 44
I was away on holiday with my brother and his friends in Mallorca on a two-week package tour. On the second night there I left a disco with this English girl. I literally just ended up with her. She pulled me into a field, pulled my trousers down and gave me a blowjob. Then she pulled me on top and I rid’ her.
The one thing I remember is she tickled my balls, which was unbelievable... the balls. That was just something else, you never would have expected that.
She was English, I’m Irish. She was 17 and I was 15. I went back home to my girlfriend after that and I was a different man. I was ready for sex. We never traded numbers or nothing, it was just all about the riding. It was excellent. I’m actually embarrassed that I don’t know her name. But she was short with blonde hair. She wasn’t great looking but she was all right looking. She was nice and funny and nice to talk to. And she tickled my balls… that was the big thing, tickling the balls, man. That made my ears wiggle.
FATHERLY ADVICE
Leif, 22
The first time was with a hippie chick. She was quite a hippie so naturally she was… natural down there. Quite a forest scene down there. I wasn’t ready to go down on her, couldn’t handle the oral thing so I figure we’ll get into some regular penetration. I put the rubber on, started going at it and five, maybe ten minutes into it, the condom kind of got wrapped up in some of her hairs there and sort of got whipped right off. I had heard that it’s possible for condoms to slip off inside and that’s what I figured had happened, but when I looked down and saw the actual entanglement situation, I was a little disturbed. It broke the mood for awhile. We hung out for a bit, smoked some weed, then got back into it after about a half hour or so.
It finished well for me but I did have to do some mouth work on her after the fact to make sure she was satisfied. My father once gave me some advice that I’ve always tried to follow. He and I were in the garage sharing a cigarette and drinking some whiskey and he just randomly said, "You should never enter a woman unless she’s had at least two orgasms." He’s a smart man, works in home health care so he’s got a mind for knowing what people need and getting it taken care of.
It’s easy for a man to get off whereas women, there’s more work involved. If you’re going to get off, you might as well put in the work beforehand. So I made sure by the end of the night she at least had two.
THE INSTRUCTION MANUAL
Mark, 21
I was eighteen and my girlfriend at the time and I were at my dad’s house in Cape Cod, Massachusetts. She had done it before, which felt weird. I was really kind of nervous, like a stage fright sort of feeling. It wasn’t like a losing-an-erection type of nervous but it was a definite intense anxiety. But she was extremely patient with me. Before, during, and after the act there was feedback and instructions. She was a feminist organization leader at Penn State and coincidentally a very good sex coach.
One of the things she told me was that a lot of guys will tend to just thrust downward: up and down, up and down. That doesn’t really stimulate the clitoris. The way she described it was, for guys it feels good when they’re pushing down, but for girls it feels good when the guy is pushing up. She got me moving in that motion and she was right. It’s made all the difference in my experiences with her and every girl I’ve been with after her. I’m not bragging but girls tend to like that better than the "Wham, bam, thank you ma’am" type of thrusts.
Losing my virginity was a little bit of a bigger thing than I thought it would be. It’s an important physical kind of rite of passage of sorts. And you want to do it well, you want to do it right.
We did it that first time and it was fun, but it’s a difficult thing to separate the anxiety of the whole situation out of it. The next time we did it, and I know this sounds counter-intuitive since guys are horny all the time, but honestly I was still nervous about having sex. But with her help I acclimated to it and she was a good coach.
LIKE A WALK IN THE PARK
Ann Marie, 31
I was 13 and I lost my virginity at a carnival, like a little street fair in my neighborhood, to a boy that was actually a… OK, he was a carnie. And I lost my virginity in a broken, unused tilt-a-whirl car inside the back of a semi truck. For some reason I just thought that was the biggest, greatest idea because you know, you’re in middle school and everybody’s talking about boy-girl stuff. And I was just, "Well what’s the big deal? I’ll just go do it." And so I found the quickest, easiest route and it was a little carnie kid who was 16, just hittin’ his puberty and I think he may have lost his virginity that day too because it sucked. Not that it ever got better for me ‘cause I’m not about the guys. I can’t remember exactly the name of the festival or where it was located. To be honest, being 31 now, I try to block it out sometimes.
The kid was working on the tilt-a-whirl ride. The whole thing was his idea. He was like, "Well, you know my boss isn’t here. I got a place for us to go." I don’t have a clue who he had running the tilt-a-whirl cars when he wasn’t there. Those people must have been on that tilt-a-whirl ride for like a good 10 minutes, not even ‘cause it was like maybe a five-minute walk to the semi truck and then it took 30 seconds long and then we walked back. The walk was pretty much the whole duration of the time we were gone. I mean it was like barely touching one another. He wasn’t even a one-minute man. That’s how I lost mine and I promised myself that I wouldn’t do it again ‘cause it was just horrible. I tried with a few other boys and then I met the first woman that I slept with and then it dawned on me, "Yeah, I’m not supposed to be having sex with boys ever. I’m supposed to be a boy."
So a couple years later I met the first woman I slept with. I was in a park and she was rollerblading and she ended up falling near me and I helped her get up.
She kept saying that her ankle was hurt and I was like, "OK, it’ll be all right. I’ll help you to your car. Maybe you should go to the hospital." I could care less, to be honest. I just wanted to leave with this pretty girl. I was like, "Sweet. She’s got a convertible and she’s pretty. I’ll sit in the car with her." Well we didn’t end up at the hospital. We ended up at her place. There wasn’t anything about her that said lesbian, specifically. There’s just that thing inside you that says, "This is one I could hit on." In the car I was kind of like playing around with her neck and telling her, "Oh, it’s going to be OK. We’ll get to the hospital." Then I was like, "Oh, I bet you have your own place." She was about 12 years older than me. I was like, "I bet it’s cool having your own place." She’s like, "Well, yeah." And I was like, "Maybe I should see it sometime." "Well, we could go there now." I was like, "Sweet. I’m ready."
In all honesty I barely ever count the first time on the tilt-a-whirl as the actual time because it did absolutely nothing for my sexual development whatsoever. It was just something that closeted me more. But as far as with the woman that I slept with, I just remember feeling a big sigh of relief.
It was clumsy, but it was good. I was like, "I think I know how to take off pantyhose." I ripped them off. I was good at that." I mean, I can’t get the crap on but I can get the shit off.
And it dawned on me that guys weren’t really what I was wanting. It was one of those things where, your first time you hope that you feel like you’re on cloud nine, and it should be totally exhilarating and that’s what my first time with a woman was like.
She gave me a ride home, at which point my dad asked me, "Who was that?" I was like, "I don’t know." "Then how did you get in her car?" "I… I don’t know, Dad. I don’t. I have no clue." And I hid in my bedroom for the next few days. I was a little creeped out afterward. When I was growing up you generally didn’t really talk about stuff like that when I was growing up. So I didn’t really exactly know how to define what happened so I went into hiding, kept a little to myself until eventually I decided, "That was good. I want to do it again." I was a little monster from that moment on and hitting on girls at the mall and taking girls home. Then I went to college and that was a free-for-all.
REFLECTIONS
Tiffany, 29
I explain first time sex as a pain you can take. And you do it over and over and over again until you’re good at it. My boyfriend was 19 and he had a very big cock.
It happened in his bedroom on his waterbed. At 16 I was truly too immature to have sex. When I went home I looked in the mirror and I thought, "Do I look different? Are people going to notice? Are people gonna think I look cool? Am I a woman? Is this normal?"
I called him up crying because of course I started to bleed. We talked and he was sweet about it.
ALL-NATURAL LUBRICANT
Kristen, 30
I was not necessarily conned into it but... I was. I was 18 and I wanted to make sure I turned 18 before I did it. I had had earlier opportunities but I wanted to wait until I was a little older. I was saving it for a graduation gift to myself.
I had been dating Rob for awhile, through most of high school. I was like, "Well I want to move to the next step." We go to the beach: Wildwood, New Jersey. We were sharing this beach house with two other couples and a single guy. There was a room with two double beds and there was another room with a single bed and pull-out couch.
Rob wanted to do it while we were at the beach house, and I thought, "After all these weeks, he finally wants to get down and busy and I'm on my period." He told me, "You really should do it now because it will hurt less." He was saying if you’ve never done it before, it will hurt the least if you do it when you have your period because, "Your period, it’s like lubrication." He gave me this whole story. I was like, "Yeah but it’s gonna be messy."
He sounded real convincing and he said the hotel staff would clean it up. I was duped from the beginning. I thought it was the right thing to do, the right time to do it. Maybe not right then when I was on my period, but Rob convinced me otherwise.
We were sharing this room with other people so we were trying to do it quick and not get caught. We were doing it and the bed broke and fell to the floor. The sheets were a wreck.
Everyone else eventually walked in and the bed is half on the floor, the sheets are off and wadded up in a ball in the corner. My girlfriend was like, "Ohmigod, you finally had sex?" And I’m like, "Yeah." And I told her about the whole period thing and she’s like, "What are you dumb?" And I was like, "Yeah." She’s like, "You never have sex on your period." I was like, "Rob said it wouldn’t hurt as bad and it would be more slippery. He said it would feel better." That’s what the dude said. He also said that the senses would be heightened.
Boys will tell you anything to get you in bed. At least it was safe sex.
A SAD STORY ABOUT SOMETHING THAT MEANT NOTHING
Mary, 22
I was in a juvenile program for kids on drugs and stuff. I wasn’t on drugs. For whatever reason my mom was fine with her other kids, she just didn’t want me. She worked for the state of Oregon and, through connections, managed to get me in.
I came home for Mother’s Day weekend and my mom went off on me on how she didn’t want me there and how she wished I would have really made her Mother’s Day special by not coming home at all. She said she wished she’d never had me, just went off. I didn’t have anywhere to go. It was a small town, I was depressed and I had to get away. My older sister’s friend Tim lived nearby. I just needed somewhere to go, someone to talk to. I was 15 and he was 19.
I walked over to his house and he acted comforting, he talked to me and calmed me down. We were sitting on his bed and I was crying and everything. He just totally pulled my strings and took advantage of the situation. It happened very quickly. I’m pretty sure I heard him say he was a virgin too but I can’t be sure if he really was or if that was just part of his story to get his pants off.
Afterwards he walked me outside and told me, "You know we’re not together, right? This meant nothing." I said, "Yeah, I know," and I walked home by myself. It wasn’t exactly rape. I didn’t want to do it but, then again, I never said yes. And I wasn’t expecting us to be together or fall in love just because we had sex. I wasn’t one of those girls but for him to say that so bluntly just sucked.
My sister was my best friend and she saw I was balling. I had gone over to Tim’s to escape but all it did was make the depression even worse so I told her what happened. She said she wouldn’t tell anybody but she was pissed because she liked him. After I went back to the juvenile home she told everybody.
My mom found out about a year later. I was back home, again on Mother’s Day and again she was bitching me out for something and offhandedly stated, "At least all my kids are still virgins." I shouted, "Fuck you. I’m not a virgin." I told her what happened and how it happened on the last Mother’s Day and how it was her fault, "There’s your fucking Mother’s Day gift, you stupid bitch." She called me a whore. I shouldn’t have gone there but she set me off with those things she said about her darling kids being virgins. We don’t go at it like that anymore but we’re still not close.
I wished I would have done it some other way. I wanted to stay a virgin until I was married and get married in a Mormon temple. It killed me that I would miss out on that. I started drinking and since I already did it once, I lost my self-respect and became a hoochie mama there for awhile. It ruined me for a good year or two but I’ve matured since then and realized that some people just suck.
The way I lost my virginity affected my sex life for years and years after that. I strongly believe that, especially for women, sex is definitely more mental and emotional. If you have a bad experience, you really can’t enjoy sex. It took a whole five years after my first time until I was able to have any pleasure from sex whatsoever.
I was dating this guy, we were sexually active for 10 months and I only got off once that whole 10 months. They say good sex makes up only 20% of a relationship but bad sex takes up 70% of it and that’s one of the main reasons I broke up with the guy. It’s like my first time ruined me and I was emotionally scarred from it. I just stopped having sex altogether until finally I fell in love and then boom – sex was awesome.
If I ever have a daughter, she’s going to be the first to know that it needs to be something special or he should at least be important to you or it can scar you. You live and learn and every experience gives you more strength. And you never know, if I hadn’t gone through that experience I might not be where I am now, so I wouldn’t necessarily change it if I could… but I might.