How to Lose Your Virginity ...And How Not To (12 page)

Chapter 8
"I HAVE TWO RUBBERS; WEAR THEM BOTH, IT WILL DESENSITIZE YOU."

At the end of American Pie when Jason Biggs’ character, Jim, is on the verge of making good on his pact to lose his virginity by prom night, his date tells him to wear two condoms because she is aware of his history of finishing early – an embarrassing fact of which most of his classmates are aware.
In spite of the less than ideal lead-in, Jim seems to perform without much trouble. And even if it’s awkward, embarrassing, or humorous, that’s at least better to look back on than a horrible first time.
More often than not, these were the stories that were openly told in the presence of others with the speaker sometimes gathering people around saying, "You’ve got to hear this one." Occasionally they would even open with, "I love telling this story."
There’s a "better them than me" element to the stories in this section. Ridiculous or embarrassing as they were, at least it made these entries memorable, unique and most everyone was able to laugh about them now.

ANOTHER NOTCH ON THE BEDPOST
Chris, 22
I grew up in a really small town, graduating class of 70 people. Real small farm town, very church-oriented, Christian-oriented so I had a very sheltered life growing up. My parents wouldn’t let me have girls over without keeping the door completely wide open.
I graduated from high school a virgin and I got a summer job working for the highway department and worked with a girl who was home for summer from college. She had her own apartment in a town nearby and while my parents thought I was going to work, I would call In sick and we’d hang at her place. We hung out for about a week, then one night we were partying and I didn’t really get drunk at the time but she got drunk and pulled me into her bedroom. We started making out and I didn’t really want to do anything, I was so scared ‘cause I was still a virgin. She just grabbed me and stuck me inside of her. So she just kind of broke me. That was it.
The next night I go over to her apartment, walk up the stairs and when I open the door she’s got about six drunk friends with her and when they see me they all start chanting, "21, 21, 21!" I hung out long enough to find out that she had just broke up with her longtime college boyfriend of two years, moved home, and I was the 21st guy she had been with in a month. I was pretty embarrassed.
The next night I met number 19 or 20, ‘cause he came by to see her. It made me feel kind of bad when I saw one of the guys she slept with right before me because he looked like a cracked out drug addict. It definitely brought sex in a whole new light for me. At that age I was still a young kid who never drank, never partied, never did anything. I had this ideal about sex, especially being brought up in the church. That ideal was snapped away from me. Made me realize that sex wasn’t that big of a deal.
I pretty much stopped talking to her a week after that so I never found out what her final number was. But I do know that about a year after that she got engaged to a guy and got married after dating him for only six or seven months. After having one guy for so long then breaking up, she went crazy and then got serious with a guy again. I happened to meet her during the crazy part.

***

She had obviously lost her virginity before because while we were having sex she said I was better than any Italian she ever had.
Thomas, 38
Amarillo, Texas

***

I WANT TO BE INSIDE OF YOU, STAT
Alan, 37
It was with my high school sweetheart. We started dating when I was 15 and I was totally guilt-ridden about sex. All we would do was make out, but we’d make out for hours and hours and I’m still trying to find a girl who can kiss as well as she can.
We’re making out and she slid her hand down my pants. Suddenly I’m thinking, "Wait a minute, it’s OK?" It opened up the flood gates and I was constantly pestering her. We fooled around like that all the time leading up to the moment I actually lost my virginity, which was in my grandmother’s house.
My grandmother was away visiting my aunt and we lied to my girlfriend’s parents and said we were going to see The Last Dragon. It’s like this Motown martial arts movie starring Vanity. I’ve never seen it, but to this day it still means something to me.
We have to go through the basement to get inside my grandmother’s house. We go inside and we go to one of the spare rooms. So I got this condom, I’m at least that prepared, and my grandmother was a nurse so I find this lubricant for surgical instruments. I’m thinking, "That’s safe. You can put that inside."
So we’re using that for lube and I’m trying to be gentle ‘cause I want to be invited back, you know. And she’s like, "It’s burning! It’s burning!" Apparently the surgical cream was not a good sex lube. So we stop and we start again. I actually did eventually get inside of her but I thought it was rude to do any thrusting so I kind of just laid on top of her. She didn’t move either, it was just one person laying on top of another person for about an hour
Afterwards we were sitting there waiting for a moment and we're both trying to say something significant. She’s like, "So, do you feel different." I’m like, "No." We ended up going out for six years.
…IN YOUR MOUTH, NOT IN YOUR HAND
Gabriel, 28
Me and my high school girl were laying in my bed eating M&M’s. We ended up doing the business. Afterwards we’re laying around chillin’. I get up to move and I see this big fuckin’ brown stain on the sheets. Then I saw the look on her face and I think, "Aw, fuck man. I know I wiped!" I look closer and I see some green bits in there and I’m like, "What the fuck?" So I get down there and I smell it, "Wait, that ain’t shit." I taste it – it’s chocolate. I notice the M&M’s bag. They had rolled out of the bag and our body heat must have melted them in my sheets. So I said, "Look baby. This is M&M’s." You know, I’m all clean and cool. Once I proved it was chocolate we were all happy again.
DO YOU HAVE ANYTHING TO DECLARE?
Bill W, 27
SHAWN WICKENS: Alright, so tell me about where it happened.
BILL W: So I was in London... with my buddy Mike here. We were there on vacation, whatever. And we got in tight... we became friendly with a couple of the bartenders at our hotel. One of them, her name was Andrea; we were hanging out with them. One night we went back with them to their place and Andrea had the adjoining room. And... I lost my virginity, and then about four weeks later I found that I had crabs.
SW: You didn’t see her again after you found out you had crabs?
BW: I had come back to the states by then. We were only In London for about a week. So this was a couple weeks later.
SW: Oh. You came back with the European crabs.
BW: Yes, exactly so...
SW: So was that a story that came out immediately amongst all of your friends?
BW: Pretty much. It's been spread around. My fiancé knows about it.
SW: Had that deterred you from hooking up with random chicks?
BW: Absolutely. No more... that was my first and last one-night stand. That’s it.
MIKE: You missed the whole part of the story. He's not good at telling stories.
BW: OK. As a postscript, in order to get it taken care of. I had to ask my mother for health insurance, so I wound up having to tell her about the whole tale of woe, which her first response was, "You fucking idiot."
SW: Did you try getting rid of them on your own before going to her?
BW: I went to one of those first-med places and they gave me some prescription and it didn't work that well. So I ended up having to go to an actual dermatologist to get it taken care of. After a week they were gone. I think my friends probably would tell the story better.
M: Then he told the rest of us. We were getting stoned one night, I didn't realize he had gotten crabs. I had went with him to London. And we were in a park... a playground of our old elementary school. Me and about seven other friends, and we were a little high, maybe a little drunk, and he said, "Oh yeah, by the way everybody. I got crabs." Yeah, everyone knows.
GLAD THAT’S OUT OF THE WAY
Gina, 23
My boyfriend and I had a history of embarrassing physical encounters. The first time we kissed or anything was after the prom our freshman year of high school. We all slept over at a friend’s house, five couples with blankets and everything all over the floor. We were making out and he was on top of me and then he just suddenly stopped and rolled off of me like he was going to go to sleep. I thought it meant I was a bad kisser because he just completely ignored me. He went to the bathroom, came back, and went to sleep without saying anything. A couple weeks later, I found out from the baseball team that he had jizzed his pants from making out and was embarrassed to tell me about it. He wasn’t too embarrassed to tell his baseball team though, so they gave him the nickname Quick Draw McGraw.
We were finally ready to have sex in the tenth grade. We were in the back of his pickup truck, and of course it was painful. Then he went down on me and said I was really wet. He comes up and had blood all over his face. I didn’t want to say anything, it was that bad. He saw himself in the rearview mirror and he was pretty cool about it. I mean we lost our virginity at the same time so it was something we went through together. After that the hymen was broke, no more blood to worry about.
OOPS. MY BAD
T.J., 26
She was 16, I was 16, and after four months of going out she consented and we decided to have sex.
She had to have a hip operation after a car accident when she was younger and she threw her hip out the first time we were doing it. There was a lot of screaming from her end which cut everything off. That didn't steer me away from sex though. There's certain human instincts that override that kind of initial trauma.

***

What I remember most about it was that outside her window was a famous house by Frank Lloyd Wright called the Robie House. I can remember after having sex laying on the bed and looking out the window at the Robie House and feeling, "Wow. That really is an amazing piece of architecture."
Edward, 28
Chicago, IL

***

HOW ROMANTIC
Scott, 24
The loss of virginity took place in the Lower East Side in New York City, in the St. Mark's Hotel, during high school, eight or nine years ago. What’s interesting about the St. Mark's Hotel is that they have an hourly rate. Normally I think it’s about $45 an hour, but for two hours it was $75, so we opted for the two hours.
I had met my girlfriend through a mutual friend in high school – Bronx Science. She was one of my close friend’s ex-girlfriends, oddly enough. He introduced me to her at his party and that’s where we met.
We dated for about a year and a half and she felt like she was too young at that point and of course I supported that decision. She was about 14 and I was very young too, just a couple months older than her. So there was a whole courting period for a year and a half and she refused to lose her virginity before she was 16. When I got to be 16, my friends were all bragging about getting it and they were 15. I had been with the same girl since I was 15 so my hormones were raging.
Weeks after she turned 16, I started pestering her again and again, "You know you’re 16 now. You don’t want to be a hypocrite." That went on for a couple of weeks. Eventually it was our actual anniversary, our year and a half anniversary ‘cause we were at that age when you celebrate six-month anniversaries, which is not really an anniversary, I know, but everything aligned perfectly.
I took her to the St. Mark’s Hotel; I think it was a Thursday. At the time I worked at Credit Suisse First Boston doing fax running jobs. A fax would come in, I would take the fax and drop it off to a banker. It was like nine bucks an hour so I put about 10 hours of pay into the afternoon.
When we walked inside the hotel I was shocked that they gave us the room because we didn’t have any ID. We hadn’t even bothered getting fakes. We just said that we needed two hours and the guy led us in and he turned on the television, this old 13" television with the rotary dials, turned it on to hardcore porno, walked out and closed the door behind him. It was a very surreal way to start out.
The room, I’d say, was about 10 x 8. The bathroom was outside in the hallway. It was just like totally rundown. The window blinds were the kind where you could still kind of see outside so we were trying to close those as much as possible. Even though the St. Mark's Hotel doesn’t look out onto the street, we were very much interested in feeling as protected as possible.
There were no blankets, no sheets on the bed. There was a bed spread and nothing else. That really bugged her so I had to go out and demand sheets, which was an odd thing to go through. And she refused to have the TV left on.
At the end of the night we lost track of time. Of course it wasn’t two hours of blissful losing of virginity. It was mostly like an hour and a half of awkwardness leading up to it. Then doing it was 30 more minutes of awkwardness. But we totally lost track of time and the management started banging on the door at the end of the two hours. We started freaking out because for whatever reason we assumed we could get arrested for doing what we were doing. There was no reasoning behind it. But it was like a bunch of kids trying to hide their drugs, like we were just running around trying to get dressed while this guy was constantly banging and we were like, "OK. We’re coming. We’re coming." But he didn’t stop; nonstop banging. So that was a wonderful way to usher in a new level of maturity.
HOME RUN ON THE THIRD SWING
Christian, 24
I went to a party with my friends who were a little bit older than me. They were going into their freshman year and I was going into my seventh grade year. We went to a party and we were playing "spin the bottle," which turned into "seven minutes in heaven."
My first spin landed on a girl. We kissed. I spun it a second time and it landed on her again so we had to make out. Then on my third turn it happened again and everyone was like, "You guys gotta do something. You gotta go in the closet," because it landed on her three times in a row. It was just the luck of the draw, and there were like eight people down in that basement.
My buddies were calling me scared and making fun of me, so I had to go through with it. We ended up having sex in the closet. It was dark in there. I was just going along with it. So we had sex for pretty much like 45 seconds and then I came out smiling like, "Yeah." And my buddies were asking, "So what did you guys do?" I’m all smiling, "Yeah, it was great." She came out adjusting her clothes and she says, "He was a ‘less than a minute-man’." It was a really bad situation because everyone made fun of me. But either way, I would have lost. They would have made fun of me if I didn’t go in there. Then when I did go in there, I still got made fun of.
Then she found out I was still only in the sixth grade, going into seventh, and then everyone made fun of her so I got her back in a way.
So… it could have been better but I still had a great time.
PUBERTY… IT’S HARD
Aaron, 37
It was with my high school sweetheart and I know that’s such a chemically charged saying but that’s what she was, my sweetheart. I’m from Modesto, California, and it was about 108 degrees one summer day, but we had decided that was the day. Her parents were gone; we planned on meeting at her place. This was discussed over the phone and through her bedroom window the night before. You know, real classy.
Physically there was some strange stuff going on like, "No, no, no, no, yes." Then "Pop!" it was over. We both walked back to my house in a daze.
I have kind of a pigeon chest that I’m really kind of shy about so I kept on this white T-shirt when we did it. I didn’t notice until it was too late but that white shirt had a big arrow of blood that went from my crotch up to my shoulders. Real fine lines of blood like almost in a perfect ‘V’ pointed down right at my crotch. We didn’t know it was there until we walked into to my house my mom went, "Oh my god! What the hell happened to you?!"
I probably told her I fell off my bike. We were in such shock that I was covered in evidence.
ZAPPED!
Vance M, 23
VANCE M: It was with this girl... Cameron. I don't remember how I knew her. She lived about 30 minutes away, in a different town, from where I grew up in Columbus, Ohio. I think I met her at like a swimming pool when I was 13 or something like that. The only other time I ever hung out with her was when I went over to her mom's house once and it was the first time I ever watched Cheech and Chong's Up in Smoke.
SHAWN WICKENS: That's a life-changing movie.
VM: Yeah. But I didn't smoke pot. Then it was near the end of eighth grade. And... it was in the summer and she actually invited me to some party out on some land, in her town, which was a few towns over. I went out there and I remember we walked off into the woods a little bit. We were kissing and then it started inevitably leading towards that. And... I remember we had started having sex and about five seconds into it and I just decided I didn't want to. And I just got this bad panic and anxiety and I thought, "What the fuck am I doing? I don't even... I don't know this girl." It was just like this overwhelming thing of a girl asking me to have sex and I was like, "I guess I say yes."
Friend: Was she older?
VM: I wish. No. I think she was my age. I think the reason I said yes was because I just didn't know. Like what else do you say when a girl asks you to have sex? But, five seconds into it I made up some excuse like, "Oh I think... the condom is hurting me. This condom's too small. I think it's cutting off my circulation," or something like that. But I made up some really bad excuse and said, "I'm gonna... I'm gonna go." And then like I started walking off and she got up to follow me and then I heard her scream. She had walked right into an electric fence.
SW: Wow... how did you avoid it?
VM: I don't remember. I think I was somehow... I was lucky enough to avoid it. At that point God stepped in and kept her away from me. And I remember I just like, I heard it and I asked, "Are you all right?" She was like, "I think so." And then I just kept walking... I was freaked out. I wanted to get out of there.
SW: You were freaked out about who you were having sex with or you were freaked out about the sex?
VM: I think it was a bit of both. The idea of it was something I was more fixated on then the actual act. And once I was in the moment it was, "I don't want this." This was always something that has been dangled over your head, especially as a male. Growing up, it’s something you are meant to pursue always and it's like the ultimate goal of any interaction with a female. And it was a good lesson because I finally realized this was not the definite end of the road that I wanted to pursue. This is just something that's there. And I think I just had that realization and went about backing out of it in a very bad way. We never spoke again. And that was pretty much it.
SW: And how did you get home?
VM: My stepfather came and picked me up later on in the evening.
SW: You didn't see her at her place?
VM: It wasn't at her place it was at some friend's house. It was kind of out in the country and... I remember I actually ran off with one of her friends and like me and her buddy were hiding in the woods and like I could hear the girl wandering around and asking for me and I was like, "I don't want to talk to her. This is going to be too weird."
SW: You were like hiding in bushes or something?
VM: Yeah. Well it was kind of in the forest a little bit. We were hiding behind trees and stuff… That's all I got.
CLOSE CALL
Marky, 26
All my family was over for Christmas Eve. After dinner my girlfriend and I snuck up to my room and had sex. And luckily we were finished and had our clothes on when my mom came in looking for us. We were sitting on my couch, my mom sat down on the bed and the funniest part of the story was when, at one point, she leaned back and put her hand on the wet spot on the sheets my girlfriend had made, that had soaked through the comforter.
My girlfriend and I both saw it. I don't know how my mom couldn't have known. Or maybe she chose to be cool about it. I never asked her.