How to Lose Your Virginity ...And How Not To (2 page)

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We did all the things every couple does at prom... went to the dance, had some drinks and stuff. And then we decided, you know, already lost the virginity the night before… we might as well just have anal on prom night to still make it a special night.
I think she was the one who brought it up and since we had messed it up kind of the night before; she felt like she deserved to give something else up the next night. It was good.
Jay, 21
Tacoma, WA

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TAKING WORK HOME WITH YOU
Dylan, 36
I truly, truly lost my virginity at the age of 12. I used to cut grass for spending money and I cut my sixth-grade math teacher's grass. I happened to go in for some lemonade and she's sitting in a T-shirt and panties grading papers. We get into a conversation and she asks me about some of the students. The teacher kind of looks like Diana Ross, very beautiful. She started to ask about which kids had a crush on her, who had a crush on other students, that sort of talk. Then she asked me if I ever French kissed, and if I knew what that was. I said, "No." So she showed me how to French kiss. Then she asked me if I ever had any sex with a woman. Again I told her, "No." So she showed me that too. Wound up having sex with my sixth-grade math teacher right there on her living room floor.
She didn’t have to tell me not to tell anybody. It was just the one time but she showed me more things than I thought possible. It was like I was thrown into a whole new category. The girls my age may have thought I was immature but that gave me a little reference point that I wasn’t as immature as they thought.
I got my normal $15 fee, some lemonade, and a little extra credit. And it turned me into the person that I am today: a womanizer, a love for the older women.
MULTIPLE FELONIES
Roger, 27
This involves a stolen vehicle, the Internet, and her mom sleeping on the couch next to us. It started out with me stealing a credit card and getting a fake AOL account. I then met this girl over the Internet who lived a few miles away. We were talking online for about a week on some AOL chat room. One night she dared me to come out and see her, bet me I wouldn’t do it. I was like, "I guarantee you. I’ll even bet you 50 bucks that I’ll be there in half an hour.
This was before I had a car, didn’t even have a license yet. So I stole the neighbor’s car, found a key under the visor, worst place to leave one. I show up at her doorstop and the look on her face was, "Holy shit I actually owe this guy 50 bucks." I meet her mom. We hang out for a couple hours watching TV waiting for her mom to fall asleep. But she fell asleep on the couch so we did it on the floor with her mom asleep right there.
She gave me the worst blowjob of my life and she did actually give me the 50 dollars, babysitting money or something. Turns out, years later I became good friends with her older brother and I found out that at the time the girl was only 13.
I did get caught for the stolen vehicle and the stolen credit card. I was facing 15 years in federal prison for bank fraud but somehow I avoided punishment. I have no idea why but I guess they dropped everything.
TWO GENERATIONS
Simon, 31
All the kids used to ask me, you know because we used to have to shower together, "Why you already got hair on your balls?" and, "Why’s your dick so big?" First time I ever had sex was with my friend’s mom. My friend’s sister blew me and told her mom I had a big dick. So the mom took me in the closet and pulled my pants down. I put my feet up against the door and fucked the shit out of my best friend’s mom.
I have no idea how old the mom was but this was the summer between sixth and seventh grade and I was grown enough to bust a nut.
Then I did the sister too.
NEWSPAPER CLIPPINGS
George, 22
I had a party at my house back when I was in high school. I'm sitting on the couch, having a good time and then all of a sudden this girl was all on my piece. She was a friend of a friend from a different school, next town over. And then some kid came and sat in between us, and my buddy was like, "Hey man, you're cock-blocking." He said, "Oh. Sorry. My bad." I think the kid was wasted. Then, later on that night she was just on my shit again. Next thing I knew... she ripped all my clothes off and we had crazy sex all night. I never called her after, she never called me, never talked to her ever again.
A few months later I was leaving on a trip for Spain for seven months. The day I left the morning newspaper said: "Girl Dies Mysterious Death". It was her, the girl from my party. They were speculating it was like a drug overdose, but the actual cause was a mystery. So… the girl I lost my virginity with died like the day before I left for Spain. It really creeped me out. It was really weird that I never saw her again or could never see her again. She was a nice girl but it was just, all right, took my virginity one night, thanks a lot. And then she was dead and I took a plane across the world and kind of started a new chapter of my life. It was a weird fate type of feeling. It creeped me out but it was interesting taking a plane and then showing up somewhere else and it gave me a story to tell when I got there.
But… I don't know, it's also sort of interesting that the person who I lost my virginity to is no longer with us. I can never talk to her about that, can never relate to her about that. You know, so it's just mine, it’s only my experience now. No one else can share in it.
Maybe I wonder if I had called her the next day would she be alive. Sure I’ve thought that, you never know what would have been different. But it was a mysterious death. They never really said. I think she was 17 or 18. Yup. She was hot.
THE DIAGNOSIS
Tammy I, 47
SHAWN WICKENS: So tell me about who it was with...
TAMMY I: I was 22 years old. I was told that I had leukemia and I had just come out of a nunnery and I was a virgin.
SHAWN WICKENS: And you found that you had leukemia so then you left the nunnery?
TI: No, no, no. When I was high school age I went through a nunnery. I eventually chose not to do that anymore, realized it wasn’t for me and left. I was originally from Minnesota but moved to Texas, got a job, and was put in the hospital for exhaustion and when they ran the tests they said that I had leukemia. So while they're in the process of running other tests I'm thinking to myself, "I am not going to die a virgin. Got to figure this out." So I went out and lived a very precarious life for two months but in the process I found a boyfriend, he was living in Houston and I called him up. I was in East Texas. And I said, "You have to come tonight."
SW: How had you met him?
TI: I met him through work. We were both supervisors for an oil company. So he comes over to the house, I drank a huge gallon of wine, not even the good stuff. We were in the throes of passion and he says to me, "Do you have a condom?" And I was like "What would I have a condom for? I'm a virgin." And he says, "Well... what can we use?" He went out into the kitchen and he comes back with a bread bag, which the crumbs were kind of interesting as far as texture goes. And so that is my virgin story… I lost my virginity with a bread bag.
SW: And I guess it worked.
TI: He was 35, I was 22. I was over it. About a month and a half later they told me I did not have leukemia. I only had mono. The doctor told me the properties were the same. I've found out since then that that is not true.
SW: After you found that out were you upset that you were driven to lose your virginity under false pretenses?
TI: No. No. I had a fellow he used to come into my stores all the time, a black truck driver, a short little guy out of Carthage, Texas. Everyone called him Black Magic and he would tell me that I needed the package. Coming out of a nunnery I had no idea what the package was. When I finally got the package it was a revelation for me. Kind of a Catholic revelation story.
I figured out, after the fact that it actually made me live every day for what it's worth. I have no regrets on anything I've ever done, ever said... anything. The sex probably, quite honestly was the best thing that came out of that whole mess.
HOME SCHOOLED
Marius P, 28
MARIUS P: How did I lose my virginity? My mother.
SHAWN WICKENS: Really?
MP: I'm not kidding.
SW: How old were you?
MP: I was eight.
SW: Did you like, know what was going on?
MP: See what happened was... my father sucked so bad in bed that she wasn't about to have her offspring suck in bed.
SW: That's the explanation she gave you?
MP: That was her explanation. Fucked up or not... she taught me how to eat pussy. I'm not kidding you.
SW: How did it happen? Were you just like in bed and...
MP: She’s fucked up. She's got major problems in the head. These days they would consider that child abuse. I consider it child abuse. But now, as an adult, I think it’s the best goddamn thing she ever taught me. So what can you do?
SW: How did she start it?
MP: I recall her coming home drunk... then she put my hand on the fucking table and played fucking chicken with a knife. That's how it got started. Crazy fucked-up shit. It's a fucked-up way but... you know, what can you say? Shit happens.

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I was losing terribly at Monopoly, very badly. This other girl had Park Place, but I had Boardwalk. So I offered her oral sex for Park Place and two grand in Monopoly money. We went into the bathroom. That's how it began.
Brody, 21
New York, New York

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THE UNIVERSE WORKS IN MYSTERIOUS WAYS
Taryn, 24
I was 13 and mad at my parents so I ran away from home. I can’t even remember what the fight was about. It was really just an excuse to go to my room early so I could sneak out my window and catch a train to meet a guy from a different state.
He was a drug dealer from Florida that I met through friends of friends. He was into the rave scene, listened to the Dead Kennedys and The Chemical Brothers and sold crystal meth, ecstasy, and ketamine. At the time I did nothing harder than weed.
He had a very complicated family situation and he was in Connecticut for the weekend visiting his parents and step parents or something. So my girlfriend and I took the Metro North train from Grand Central up to somewhere in Connecticut. He picked us up and drove us somewhere, all I remember was it was by the water; a one-bedroom studio, a very temporary kind of setup. I’m a gentlewoman and my man was a gentleman so we let his friend and my friend take the bed. The drug dealer and I took the closet.
It was a closet with those sliding doors, so we laid down on the carpet and slid the door shut. Like I said, I was 13 and I had never really done it before. I’m a small person and was even smaller years ago. He was at least five years older and over six feet tall, so he was a weight to bear.
We discussed it briefly beforehand. It was consensual, it was safe. There was a lot of pain and suffering but I got through it with rug burns and it was a beautiful experience. He asked if it hurt. I said, "Yes," and he said, "OK. That’s probably normal." I was shocked at how sweet he actually was about it, given my stereotype of drug dealers at the time.
Then this whole weird episode turned unfortunate because my parents managed to track me down to tell me my Great Aunt Gerda had died. She was an amazing woman who moved to the Lower East Side after escaping from Nazi Germany. She settled down with a jeweler, became a jeweler herself. Anyway that’s who died the night I lost it. Talk about feeling responsible for something in the cosmic sense. You know, being a self-centered person at the time, I thought I had something to do with it. So I came home.
I was expecting to never hear from the guy again, but he started persistently calling me. The guy got so attached so I swore never to give my number out on a one-night stand again. I never ran away from home again either. I suppose that was less of a conscious decision and more of a lack of need. I got my space from my parents anyway because after that incident they sent me off to boarding school.
GIRLS GONE WILD
Frank, 23
We used to party over at my buddy’s place. His parents were straight off the boat from Poland; both PhDs, both very intelligent people. One was a raging alcoholic, the other barely spoke a word of English. The dad would be 16 drinks deep by the time we’d get to the place. He used to drive drunk into town and pick up steak filets and beer for us. Go back to the house and we’d have raging barbecue keggers.
The parents were successful business people. They had a hot tub, which was perfect for us. I guess the parents just didn’t give a fuck what we did. The mom would walk around topless in just her underwear. The dad built his own stereo systems and we used to chill out with him and listen to music. I actually got into the Rolling Stones because of him.
This was in high school about the time people started hooking up with each other and everything. Two girls and I, we were hanging out in the hot tub. We were all friends and I had fooled around with one of them before. They were best friends and pretty drunk and we were all in our underwear. They started making out first, then we all started making out. Well, I asked them to make out. You know this was in high school so you could be very up front with girls if it was in a comfortable situation. I had one of the girls wrap her legs around the other girl’s torso. The other one’s making out with her, feeling the tits. I start banging her.
We’re going at it, I’m doing the one girl and I hear the voice of my good friend, Larry. I look over and I see Larry and with some other guys like peaking in, watching us. And Larry is looking very intently to see if my shit is in there or if we’re just dry humping. Larry’s like, "Oh yeah. Yeah, yeah. It’s in there guys." He starts clapping then they all start clapping. I’m doing the one girl then it was like, "OK, here we go," the other girl hops on. I’ve been tested since but this was all unprotected sex. We were pretty drunk. We finished up and then the second girl got out of the tub crying because apparently she liked me for real. So I think she was sitting there watching me with the first girl, getting very jealous and that’s why she was willing to hop on.
I had hooked up with another girl in the hot tub the week before. But that was like four of us in the hot tub, girls and guys. As far as I knew, that time with me and the two girls was the first hot tub sex, unless the mother and father probably had done it.
The whole thing lasted maybe 15, 20 minutes until the one girl got fed up and couldn’t handle being in her own head and went in the shower and freaked out. In retrospect I feel very bad about the whole situation because she was very upset. She wasn’t very attractive. Her friend, the first one, was extremely attractive. When the second girl got out and ran into the shower I told the first girl, you know, let’s go in there to try to talk it all out.
The one girl gave excellent blowjobs. That was the one who wasn’t very attractive. That’s how they always get you, you know what I mean? The real hot ones, they’re the ones who just don’t know how to do it. The sex itself was under water, it wasn’t very pleasurable. It basically turned into, "Look guys! I’m having sex!" The shower was a little bit better because we kissed a little bit more but what was just because we were all wasted.
Later on that night I was sitting with the guy’s dad who owned the place, feeling proud of myself and he played some AC/DC and this song called "Rasputin" by Boney M. It’s a good song. I’ll never forget that. The downside is that I was feeling proud of myself for doing a very horrible thing. I’ve grown up since then.
It was basically a disaster but at the same time I did lose my virginity to two girls in a hot tub. If they were in front of me right now and asked if I wanted to do it again, I would. But… I’ve forgiven myself and I’ve accepted absolution and I think I’m all right.