How to Lose Your Virginity ...And How Not To (8 page)

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The weird thing was that while I lost my virginity, his sister was sleeping next to us in bed. It's hard to believe she could be sleeping the whole time.
Alexis, 30
Gent, Belgium

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I KNOW THAT GIRL!
Eduardo, 22
I was 17, the girl was 15 and she was a slut. My friends knew her and they were all, "She likes you." I was like, "Oh. All right." You know I was 17, the funny little bastard I was, I went up to her and was like, "Wha… uh… yeah, um… wah, wah, wah…" Somehow I got her phone number and she got mine.
My parents were gone for a long weekend and she called. She came over. I was 17 and didn’t know what to do. She was 15, but knew exactly what to do. Definitely not her first time. Definitely, definitely not her first time, which was kind of creepy yet kind of good at the same time.
It’s three o’clock in the afternoon and we’re in my room. My sister gets home from school and barges in my room like always, saw us and screamed, "That girl’s in my third period geometry class." It was no good. I got laid but my sister got a story about her older brother. Lock your doors, that’s all I’ve got to say. Lock your doors.

***

I’ve never seen a human move faster than my girlfriend – pulling everything with her – the covers, the pillows, everything to the corner of my bed and leaving me naked wearing a condom, looking at my brother who says, "Yeah man, that’s all you."
Richard, 23
Washington D.C.

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DISTURBIA
Charlie, 33
I ran on the cross-country team in high school. There was a big bunch of us who started training really early in the summer. We were running miles and miles every day so we got to be this big kind of tight-knit group. That’s how I sort of fell in love with this girl named Karen on the cross-country team.
It was one of those typical teen movie scenarios where my parents were out of town and she comes over because she knows I’m alone. That was it – we had sex. The only remarkable thing about it was that I bought these lubricated Trojan condoms. And when I put it on and it was all wet and she got pissed off at me because she thought I had cum already. I had to convince her, "No, no. That’s not cum. It’s the lube on the condom." What made it the worst teen movie scenario possible was apparently I didn’t have my blinds shut all the way. A few hours after it happened this neighbor kid from across the street called me up like, "Charlie?" And I was like, "Yeahhh? What’s up?" And he said, "Charlie? Uh…" He didn’t really say anything and I was like, "Yeah. What’s going on?" He’s like, "Uh… um… is everything OK over there?" I was like, "Yeah… everything OK over there?"
Apparently he saw the whole thing happen or who knows, maybe his parents saw it happening too. But it was the worst aftermath of losing your virginity that a guy can ever have because it got back to my parents.
It was the worst, most humiliating thing having my parents sit me down on the sofa and give me the big talk. They were pissed off that I had done it while they weren’t home. They were pissed off and freaked out because I was 17 and she was 15. But I had done what any red-blooded 17-year-old teenage boy would do while his parents are out of town which is fuck a girl.
My parents did everything they could to paint what had happened in the worst possible light. Telling me that if her parents found out they’d kill me, or saying I better pray she doesn’t miss her period. It was the worst way they could have dealt with it… ever. It was terrible.
The having the sex part, that was great. And she and I got together and did it a few times after that. But the whole aftermath with my parents was, I thought, inexcusable. And my parents are great parents, but I always sort of held that incident against them. They could’ve been a whole lot cooler about it.
WILLINGLY TRICKED INTO HER TENT
Rich, 20
I worked in a video store and my boss invited me to her graduation party. We were good friends, sort of a brother-sister kind of a thing. So I went to her party and I got really drunk, the most trashed I’d ever been at that point in my life.
My boss’s younger sister was the same age as me and she was hitting on me uncontrollably. No one was allowed to leave drunk so there were all these tents set up in the backyard. I ended up sleeping with her in a tent. It was pretty shitty. While we were in there I heard her mom say, "What? There’s a boy in there? Get the shotgun." I immediately ran out of the tent and passed out in some secluded corner of the backyard.
The next day I was back at the video store. We were closing up and all of a sudden my boss walks in and throws her huge ring of keys at me like fast pitch, as hard as she could. She screams her head off because not only was it with her sister but she also found out the sex was drunkenly unprotected.
She yelled for awhile saying that I could have gotten her sister pregnant and she doesn’t know what I could have caught because her sister was by no means a virgin. Then her mom called me and said I had to tell my parents or she was going to tell them for me.
My dad was on the front porch smoking a cigarette when I got home. So here I am, 15 and I had to tell my conservative parents: "Listen. At that graduation party, I got drunk as fuck, stoned off my ass and then had unprotected sex with my boss’ younger sister." His response was, "Well I knew this was going to happen. I just hoped that you’d use a condom. What the fuck were you thinking?" He hollered for my mother to come outside and her response was kind of like, "Oh my god! My only boy!" They grounded me for a week.
My boss and I made up. She knew I was young and drunk and she knew that her slut sister was hitting on me crazy. At first she was like, "Ohmigod, you had sex with my sister." Then she was like, "Oh my god. My sister totally duped you into having sex with her," which she kind of did… but she kind of didn’t. I mean when you’re so drunk that you can't even sit in a chair and some random hot girl is sticking her tongue in your ear, what are you gonna do? You’re gonna do whatever she tells you to do.
You know, many people would regret something like that but honestly, I don’t regret it. It’s good to get it over with. I didn't really know her and if she was bored by it, well I didn’t have to deal with that later. If she had been a girl that I really cared about, and she was like, "Huh? That’s that?" It would have felt shitty to put someone you cared about through that.

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I wake up after it's done and she whispers in my ear, "Thank you." I fucking roll over to the side, I was 14 years old, I roll over and I look over the side of my dad’s bed and there’s a condom there and I fucking started crying. All my friends busted in and saw me crying.
Gary, 22
West Park, OH

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I READ IT SO IT MUST BE TRUE
Tamara, 23
I had read in Cosmo about this study that said the average age that boys lose their virginity is 16. Average age that girls lose their virginity is 17. So I was like, "I’m 17. Time’s a wastin’." My family was about to take a trip to Florida for spring break. Being from an all-girls school there was, of course, slim pickings so I decided I was not gonna come back from Florida unless I was a woman. With that plan in mind I signed up for teen volleyball one night but it got cancelled, so I wound up wandering the beach at night in St. Petersburg, Florida.
I ran into three guys who ranged from 16, one was 17, and one was 19. The beach was pretty deserted, considering it was spring break. They were totally the first guys I saw. We started talking and they were acting like stupid guys and one of them said, "Hey, why don’t you give us head?" I said, "OK." I would have managed to bring it up even if they hadn’t.
I wound up leading them all over various parts of this beach. First we went to the sauna, I was like, "No, this isn’t right."One of the guys like kind of pinched my stomach and said, "Oh, you have rolls on your stomach." The other guys were like, "Shut… up… dude," and, "Don’t piss off the girl." Whatever, I was a woman on a mission.
We finally found this secluded place on the beach. The story I tell most people is that I met just one guy and we slept together but really I met these three guys and I went down on the first one. That took maybe 10 minutes. Then I went down on the second one, that took like almost an hour ‘cause he’d been swimming, or whatever. He tried to get me to sleep with him, but I said no ‘cause he was all vulgar and in my face about popping my cherry. Plus the third one was much cuter.
So I wound up sleeping with the third one and it was so cheesy. Like when we finished he threw the condom over the wall at his friends, then they threw it back and it hit us and I screamed.
That happened maybe halfway through the trip and I didn't hang out with them again because obviously I didn't have a cell phone or anything back then. But there was one time when the guy I slept with was walking into the hotel. I didn’t see him at first, then all of a sudden I felt this weird jolt of electricity I turned and it was him. I thought it was good sex only because I had no basis for comparison. My legs hurt the next day. I think I pulled a groin muscle. That was the only thing that hurt. I thought I got off, but that was before I really understood what getting off was. After we got back home my mom confronted me with, "Did you have sex in Florida?" And I was like, "Nooo… what are you talking about?" And she tried to like hedge around it, she’s like, "I think you did," And I was like, "That’s ridiculous." And finally she broke down and just was like, "I read your diary." She started crying. My diary was in my bag and she found it. I had been keeping it for ten years and she never read it before. She found out everything, all the explicit details.

Chapter 6
"TONIGHT IS THE NIGHT YOU MAKE ME A WOMAN / MAN"

I went to New Orleans for Mardi Gras the year after Hurricane Katrina hit. I found cheap fares to Austin, Texas, the drawback being that I had an 8-hour solo drive from the airport with Fat Tuesday awaiting me on the other side. As I drove east on I-10, pushing 75 mph in an effort to make good time, I heard on the radio, to me, an unfamiliar song "Tonight Is the Night" by Betty Wright. In it she sings, "Tonight is the night you make me a woman. You said you’d be gentle with me and I hope you will." An appropriate sentiment for the work I had set out for myself, and a reminder that despite some people’s assumptions, not all first sexual experiences are clumsy or disappointing. There are those lucky few who do have amazing, monumental, and even joyous firsts.
These stories aren’t completely devoid of clumsiness or awkwardness. Nobody gets behind the wheel of a car for the first time and automatically knows how to handle it. And, as is often the case with memories, they sometimes sweeten with age. But these entries represent the type of experience that many aspire to have, or wish they had.

SECRET RECIPE
Debra, 25
I was younger than I thought I would be when it happened, but it was with my best friend. We’re still friends, have been for over 15 years. It was in my house, in my room, so I was in a place where I felt safe. But I was still all nervous and shaky. He was above me, and he started shaking too. The bed started to move. I was like, "What’s the deal?" And he said the coolest thing, "It’s my first time. I’m nervous too." It was great because he’s a boy and boys don’t say that.
Afterwards we made brownies and I didn’t let them cook all the way. I just got excited and wanted the chocolate as soon as I could get it. They were hot and still gooey. Now, whenever I smell brownies it reminds me of the first time.
RIPE FOR THE PICKING
Alison, 26
I grew up in Canyon, Texas, which is 15 miles south of Amarillo. Summer was upon us and I was about to go into high school when I met this boy who had just moved with his father from Omaha, Nebraska. Wesley was really cute and really shy. He knew nobody in school and I befriended him. The last days of that school year we would walk home together.
We became close friends that whole summer. We would go Rollerblading during the day, and at night I would sneak and wait underneath his bedroom window and he had never snuck out before so I was a bad influence on him. I was never bad either, but he just gave me reason to be a bad girl. We would sneak out to this house being built and fool around; it was like the shell of a house. He was going into the eighth grade and you know, boys at that age are really awkward and stuff but he could tell, he knew I was making the moves on him.
Wesley had a strawberry garden in his backyard and one afternoon he picked and cleaned all these strawberries for me. We’re outside laying in the grass, I had my head on his lap and he’s feeding me these strawberries. He was wearing an unbuttoned long sleeve shirt with the sleeves rolled up and a white t-shirt underneath, real tight Levis jeans with no shoes. It was such a good… everything. He’s feeding me these strawberries and I totally kiss him. Then he led me to his room. He was really cute and I wanted to deflower him, I wanted him to deflower me. He said he’d never done this before. I said, "Me neither." It just happened and it was real nice.
I had a real shaky rapport with men up to that point. My parents were divorced so I didn’t really trust guys. So this was a very positive male experience and it gave me a reason to trust guys but he eventually moved back to Nebraska. His dad was like the Gestapo and wouldn’t let him do anything. He felt really repressed because of it so he moved back with his mom in Omaha.
The song "Omaha" by Counting Crows always made me think of him and I've always really loved that song because of that boy.
I COULD’VE BEEN A STEP DAD
Kyle, 47
New Year’s Eve. I didn’t have any plans so I went to a party with Leonard, one of my older brother’s friends. Her name was Suzanne. I’ll save her last name for myself. Can’t remember the names of the other girls that Leonard brought.
We were drinking. So she thought I was around 17, but I was really 12. I was just with older people and I looked older, big for my age. I weighed about 130 lbs. so I just looked like a skinny 17-year-old. She’d expected me to stay without having to call home and ask my mom if I could spend the night so I obliged. I remember drinking and having a good time. She was a knockout.
Suzanne and I went up to the bedroom. Leonard stayed down there with two of the girls. He got it on with both the girls downstairs. I went upstairs. Got into my thing, whatever I could do at the age of 12. Right in the middle of it all, she asks if I was gay. I had no moves, I was very innocent.
I mean, back in the '70s they didn't have all the stuff they have on TV now, or the Internet. The pornos now. They didn’t have any of that shit when I was a kid. And it’s a little scary and overwhelming seeing a naked body for the first time. My older brother used to have Playboy mags. So the first I got was just like, tit shots. That was as far as I had ever seen. So the whole thing was nerve-wracking.
I really do believe she thought I was 17 and assumed I’d had a couple experiences under my belt. Ended up almost going to Texas with her. She asked me if I knew how to drive. I said, "Sure, I know how to drive." I had already had sex with her, might as well keep the illusion going.
She had an eight or nine-month old child crying in the crib next to her bed, which I felt bad about. Even at that age I was like, "This is not right." She had her own place though so I figured, "OK, she knows what she’s doing." She asked me if I could drive her truck to Texas with her. Split the driving, go down there and start a new life. So I was like, "Yeah, sure. Sounds pretty good." Now the guy I went with, Leonard, the next morning he says, "Kyle, we need to cut out. We need to get you back to your house." I said, "You go. I’m staying here." He said, "Ok, if you want to stay here, suit yourself." About three hours after Leonard left, she told me she had to go shopping for the kid. So I was there by myself with her baby. The doorbell rang, I answered it in my underwear, and it was her older brother. He was like, "Where’s Suzanne?" I said, "She went out to buy her kid some baby food." Then he just kind of forced his way inside the door, sat on the couch, told me to go put my pants on. I was going up the stairs and that’s when my two older brothers and Leonard knocked on the door.
I’m standing in my underwear and they ask me what the hell I was doing there. I told them "This is my new home. I’m with Suzanne now." They dragged my ass out of the house, threw me in the fucking car and beat the shit out of me the whole drive home. When we got back, my mom beat the shit out of me some more.
So that’s how I lost my virginity. She was 18 or 19 and thought I was 17 and knew how to drive a truck. That was the first and the last time I saw her. Never heard what became of her.
SALUTE THE RED, WHITE, BLUE & GREEN
Sara B, 26
SARA B: I was sort of older when I lost… well… I consider it older because people lose it fairly quickly nowadays. But I was in college, I was actually planning to wait until I was married. Yeah, that didn’t happen.
SHAWN WICKENS: That’s a pretty common plan though.
SB: Eventually like two months into my sophomore year after I had put this guy off for months I was like, "Oh, OK. OK. I’ll be your girlfriend." He also hadn’t had sex with anybody so it would have been both our first times and we were both sort of, "I don’t know. Maybe we should." I talked about it with my roommate and she told me, "Oh. If you’re going to, you have to go on the pill." I said, "Really? Is that what everybody does? OK." So without telling my boyfriend I went to the gynecologist and I had never been before. And I was like, "Uh, I need a prescription for birth control pills." I had to go to this class. It was creepy.
SW: Like a school gynecologist?
SB: Yeah, yeah. And it was really funny because we had to go to this class and there were all of these girls sitting in on this birth control pill seminar. So I went on the pill and I remember I told him. He came to my dorm room and I was like, "Look what I got." And he got really freaked out. He was like, "Well I don’t even know if I want to have sex with you." And I was like, "Oh. OK." That was in October… I actually remember the actual date we had sex. It was November 28, and it was… 1998.
I’d been on the pill for like a month.
SW: You started taking them even though he freaked out?
SB: Yeah, yeah. So the whole story was… we hadn’t planned on it, but I went to his off-campus apartment, he had made me dinner. Had some wine. His roommates were gone. He made me dinner. We had some wine and… we watched Dances with Wolves and started making out and we were all romantic so he was like, "I think we should make love," I think is what he called it. I was like, "OK." So we went to his room and… we were like just about there and he was like, "Oh, fuck. I don’t have condoms so… Um. OK. Let’s go into my roommate’s room." We went to his roommate’s room, went through his closet, literally tore apart his closet looking for condoms.
SW: Were you half-dressed at this point?
SB: I was completely undressed at this point, in his roommate’s room. We finally found some and they were non-lubricated, which we were like, "Uh, OK. I guess that’s fine." Went back to his room. And we did it, you know, missionary. I think he was like in and out maybe two or three times and then it was over. And I was like, "Oh. Was that? Oh… Cool." And he was like, "Let’s have a cigarette."
SW: Were you even smokers?
SB: No. No his third roommate, the one we didn’t take the condoms from, he was a smoker. We took his cigarettes and we were like, "Yeah, that’s really sexy. Aren’t you supposed to do something really sexy after you have sex?" But then the funny thing was that the next day he made me a necklace because we had shared this really… special, you know…
SW: What was it made out of?
SB: It was beads. It was like… ohmigod. He was a very… all-American boy. So he made this red, white, and blue beaded necklace and then in the middle there was one green bead and that symbolized me because I really liked green. I might actually still have that. I don’t know.
SW: Did you wear the necklace often or no?
SB: Ohmigod, every day. I was really cheesy about it too. I was like, "OK, I’m totally gonna marry you because we were both virgins and we lost our virginity together so." It actually lasted for a year. We still randomly communicate off and on.
CONCEDING THE MATCH
Oliver, 31
I was very lucky to have a sweet, smart girl as a high school girlfriend because I didn’t deserve her. I was a horny 17-year-old and I had verbally pressured her so much to go all the way that she came up with this system that, looking back on it was quite mature for two teenagers. We decided that the day she wanted to do it, while we were fooling around she would give me two taps on the back.
One afternoon we were hooking up in my bedroom and out of the blue she tapped me twice on the back. I said, "Really?" She didn’t answer, she just tapped me again. That was that. We giggled a lot afterwards, which surprised us. I can remember telling her that maybe the first time isn’t supposed to be too serious. It’s supposed to be kind of fun and loose.