How to Lose Your Virginity ...And How Not To (3 page)

Chapter 2
"HOW DO YOU PUT THESE THINGS ON?"

My memory on learning how to properly use a condom is hazy. I would like to say that I received my first lesson in high school health class. But I think the first time I witnessed a condom "used" was when a sex ed teacher demonstrated putting one on a banana in some movie, or it may have even been in an episode of Beverly Hills 90210. I can’t remember exactly.
I can, however, say with some degree of confidence that my generation witnessed, grew up during, the condom explosion. Because of HIV/AIDS, the increase in teenage pregnancy, it made conversations about condoms imperative. I can recall when SPIN Magazine included a free condom in one of its issues, causing headlines and stirring up debate. I remember the first time I saw a commercial for Trojan condoms on MTV and people called it scandalous.
Nowadays free condoms are available on most college campuses and many high schools. The importance of protected sex has become so ingrained in our collective consciousness, even some bars leave them out. Condoms are part of the process, the experience, it’s even part of the foreplay.
Here now are a few more reminders of the physically safe way to approach intercourse, in which condoms played an important role in the stories themselves.

THE ESCAPE CLAUSE
Derek, 30
I’m from Winston-Salem, North Carolina, maybe a four or five-hour drive from Myrtle Beach, South Carolina. It was a trip we’d make maybe on a quarterly basis. My friend Bob’s parents owned a beach house there so a bunch of us 17-year-olds went to Myrtle Beach, which I guess would be an appropriate setting for some people to lose their virginity. Really it’s just a very cheesy place.
There was me, Bob, Nate, Ed, and Terry. On the first night of a weekend trip we were hanging out on the beach smoking some dope and we met these girls who were about our age. Our buddy Terry was two years older than us and knew someone who could get us beer, or one of the girls was able to get us beers. Whoever got it, we took a bunch of beers to this girl’s place where there wasn’t any parental supervision.
I connected with this one girl and I was definitely nervous because I could see where the progression was going. I was still a virgin because I had just broken up with a girlfriend of two years who wanted to wait until marriage.
Everyone was playing a drinking game, which loosened me up a bit. I don’t remember exactly what took us from that level to the next, but she said to me, "Let’s go check out my room." We went to her room and started to hook up total high school style. I wanted to try to have sex but I didn’t know if it was a possibility so I excused myself. I went up to Terry and asked him, "Do you have any condoms?" I go back to the room and we’re finally making progress.
It gets to the point where we’re naked and I think, "All right. It’s all or nothing at this point." I put on the condom, make the move, and honest to God I lasted maybe nine seconds.
I don’t know how I kept it together but I said, "Aw, shit. Hold on one second." She was just getting into it and she was like, "What? What?" Not knowing what to do, I stalled and blurted out, "I think the rubber broke." I went back out to the living room and asked Terry, "Do you have another condom? He was like, "Why?" I was like, "Just give me another condom if you have one," thinking I could buy enough time to work myself back up. I got another condom and went back to the room but I had lost it. It so wasn’t going to happen. The girl just looked at me and asked, "Do you want to go out and play the rest of the drinking game?" It was the greatest thing she could have said to me. I didn’t know how to segue out of there but she did it for me and let me off the hook.

***

Some Japanese condoms are a little bit smaller and a lot of guys in Japan will sort of brag secondhand about the size of their penis by saying they have to order their condoms over the Internet. But you can find international condoms in any convenience store.
Stan, 26
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 and 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.