How to Lose Your Virginity ...And How Not To

How to Lose Your Virginity
(...and how not to)
© 2010 Kindle Edition (updated 2/12/12)
by Shawn Wickens
For questions or comments
- contact the author through
www.LossofVirginityBook.com
A portion of the proceeds of this book benefit RAINN (Rape and Incest National Network).

INTRODUCTION
1.
YOU’LL NEVER BELIEVE WHAT HAPPENED TO ME
2.
HOW DO YOU PUT THESE THINGS ON?
3.
PENIS IS THE PROPER WORD. VULVA IS THE PROPER WORD
4.
IT'S NOT THAT BAD. IF IT WAS, EVERYONE WOULDN'T BE DOING IT
5.
WHAT’S GOING ON IN THERE?
6.
TONIGHT IS THE NIGHT YOU MAKE ME A WOMAN / MAN
7.
JUST FELL INTO IT
8.
I HAVE TWO RUBBERS. WEAR THEM BOTH, IT WILL DESENSITIZE YOU
9.
WE DROP KICKED OUR CHERRIES
10.
IT WAS A TRAIN WRECK
11.
MEN CAN BE SUCH PIGS
12.
NO MEANS NO
13.
THAT’S ME IN THE SPOTLIGHT, LOSING MY RELIGION
14.
IF I HAD THE CHANCE 2 DO IT ALL AGAIN
I WOULDN'T CHANGE A STROKE…
15.
GOING TO THE CHAPEL AND WE’RE GOING TO GET MARRIED
16.
I NEVER DID IT!
17.
THE OTHER SIDE: TAKING VIRGINITY
18.
I DID IT MY WAY
CONCLUSION
HISTORY OF THIS PROJECT
SPECIAL THANKS

INTRODUCTION
Interviews were conducted during several road trips across North America in the following cities:

I spoke to over 1,000 strangers. These are a few of their stories.

Chapter 1
"YOU’LL NEVER BELIEVE WHAT HAPPENED TO ME."

When I met Vivian, I was speaking to a group of ladies out in the Warehouse District of Cleveland, Ohio for a bachelorette party. The bride-to-be was visibly shocked when she heard one of her bridesmaids tell of her evening of sex with a married man.
The title for "MY PARENTS PROBABLY WOULDN’T EVEN BELIEVE ME IF I TOLD THEM WHERE I WAS" was inspired by an actual quote from Zoe, an 18-year-old I met in Nashville. She was hanging out at a coffee house on a Saturday night because, as she put it, her wild times were behind her.
After I spoke with Shigeru I found myself asking him if it really happened. He assured me it had, he seemed very genuine, and his story was even verified by his then-girlfriend who had heard it before. So, it’s so crazy, it must be true! Right?
Teachers, threesomes, porn stars... it really happens.

WE WERE ONLY FRESHMEN
Barry, 28
This began when I was 14 years old, the summer going into my freshman year in Catholic high school. I had had my first kiss only three weeks earlier. It was also the same time I started drinking and partying. Kind of young for that kind of stuff but I’m from Iowa where 14 is about the average. It’s Fourth of July weekend and I’m at this party flirting with a real cute girl, same age as me, who’s already dating a senior: Dolph.
She was a big fan of blackberry brandy but couldn’t hold it, couldn’t handle herself. Everyone knew she was the type of girl who got drunk and liked to mess around. She was drunk, I was drunk, and we snuck into the guy’s room who was throwing the party.
Her boyfriend, the senior, happened to be a middle linebacker for our varsity football team. I was already warned. I was warned when I was flirting with her. Her boyfriend was one of those guys who would go up to people and say, "Head or gut?" And if you said gut, he’d punch you in the head. If you said head, you know, vice-versa. So I knew what I was getting myself into. Nevertheless, I’m 14, and this is about to be the first time I ever showed my penis to a woman. I was really insecure about it because I was a 150-lb drunk pothead. You know, how could I physically compete against a 270-lb middle linebacker. But we had beautiful sex, listening to "The End" by The Doors and we were both big Doors fans. She said it was great.
The linebacker found out, everybody found out. So once school starts, big ol’ Dolph sees me on the bridge and I just about shit my pants. He throws down his books, holds up a fist and asks me, "Head or gut?" I was like, "Dude. I’m really sorry. I didn’t know. I didn’t know." He spit chewing tobacco all over my books. That was the worst of it. The way I looked at it, this 270-lb senior got hosed by a freshman. He was a football player, I was a nobody and I had a great time humping on his girlfriend.
It turned out that my best friend all through high school, who I hadn’t met at that point, he was the guy whose bed I lost my virginity in. And he and the girl I lost my virginity to ended up getting married three years ago. That took place when I was 14, I’m 26 now and I was the best man at their wedding. I'm not sure if Nate knows and he's like a brother to me. I’m sure she hasn’t mentioned it to him. But the fact that it was in his bedroom, I’m now his best friend, and was the best man at their wedding, I think makes it a good story. Everyone I tell seems to like it… except for Nate, who I’ve never told.

***

You'd be amazed what two naked people can do in a movie theater. It was a long movie. It was a hell of an experience doing it during and not really watching, As Good as It Gets. I own two copies of it on DVD for memory’s sake. One is still wrapped in the plastic for posterity.
Jake, 24
Ocala, Florida

***

DÉJÀ VU
Maddie, 21
I was with my boyfriend at a party at one of our friends’ houses. We were doing this camping thing-a-majing, there was a bonfire and everyone had blankets on the ground, We were making out and he climbed on top of me and said, "Can I?" and you know, I was drunk. We decided to have sex right then and there.
I thought it was gonna be a big deal, but afterwards I was like, "That’s it?" I mean it is a big deal when you’re young, you don’t even know the emotional effects it has on you. I think sex put a strain on the relationship that, as kids, we weren’t ready for.
So I went home with one of my friends, she was actually at the party with me. I told her that I slept with my boyfriend and she was like, "Well have you ever slept with a girl?" And I said, "No." So she slept over and we slept with each other.
It was a better experience with her. It was more sensual, more erotic I guess. Maybe more crazy and daring. Maybe that’s what made it better.
But my brother found out and told everybody. That was harsh. My parents found out and that wasn’t good either. Now they’re more supportive about my sexuality. My mom still has issues but my dad is happy as long as I’m happy.
About a year ago, I get home from my college and my parents tell me that they’re moving and they bought a house. They tell me the address and it turns out to be the house where I lost my virginity with the guy in the backyard. That’s the house they’re in now. My dad laughed but my mom just rolled her eyes. She wishes I was still with guys.
SO… WHAT BRINGS YOU HERE?
Jimmy, 43
I was living in London, lived there from when I was 10 to 19. I lost mine to a Scottish junkie in a squat in World’s End, this section of London. Iggy Pop's album, The Idiot was playing… the song "Tiny Girls." I was dealing at the time, so I guess you could say she was a customer of mine.
This girl, she had just broken up with her boyfriend. She was pissed off and wanted to screw somebody to get back at her boyfriend and I was happy to step up. It was just fate, "Yeah, why not." I was 14 so she was, well... an older woman. She was like 18.
The thing that was weird about it was the next morning I went down to the kitchen to get some stale corn flakes and this other girl I went to school with was there. She had lost her virginity the same night to a male junkie in the same freaking squat. We were both too cool to acknowledge anything that happened so we just sat down and looked at each other and ate breakfast. I ended up dating her. Yeah, so it was very bizarre and pleasant.
Then two weeks later they tore down the squat. So all I have left is the album – Iggy Pop.
PB & J
Mario, 30
I discovered sex when a fellow male classmate and I had sex on my parents’ kitchen table. We were 14, we were there, it happened, and we needed lube. We could be so lucky to have butter or olive oil. All I could find was crunchy peanut butter. It served its purpose. When we were done I cleaned the kitchen table with a mop. I was real paranoid about it because I had to sit at the kitchen table and have breakfast with my family the next morning. They suspected nothing but could probably tell I was a little bit happier than usual.

***

I broke into the storeroom where the cameras were monitored and stole the videotape so I got myself losing my virginity on tape. I know how long it was, the exact date, the exact time… everything.
Calvin, 22
Carmel, IN

***

HAPPY BIRTHDAY… MR. PRESIDENT
Seth, 24
To tell you the truth I don’t really remember her name. I want to say it was Raquel or Rochelle, something like that. When I turned 16 my dad decided that I was getting to that age where I was old enough to meet girls and stuff so for my birthday party he gets me a chick who pops out of this huge ass birthday cake. It was totally unexpected. I just thought he had this huge birthday cake decoration. Everyone thought that, and then a woman jumps out of it.
It was a PG affair, she wasn’t topless but later on I got to see them anyway. It was a pretty big bash, family and friends were there. My stepmom flipped out because this girl was like an escort. She was pretty hot, I got to talking to her and she was sitting on my lap pretty much the entire party. It was pretty fun, you know having an attractive lady show me all that attention who, granted was getting paid to be there – jump out of the cake and surprise me, but one thing led to another.
She asked me, "Do you want to come to my place later?" I was like, "Hell yeah!" I was 16-years-old, I had a sexual libido from hell. You know at that age when it kicks in all you need is a hole with a heartbeat, let alone a sexy escort.
After the party I told my folks I was going over my friend Tony’s to hang out and chill with some buddies. I got in her car, went to her place and she pretty much told me what to do. Showed me what it’s like to have sex and stuff. Then I rode home on my skateboard.
LIFE IMITATES PORNO
Shigeru N, 25
SHIGERU N: I used to deliver newspapers. In Japan. This was an area that had a real tight community, a bunch of tall buildings and whatnot. So one day... I delivered newspapers and at the same time I collected for the bill.
SHAWN WICKENS: How old were you?
SN: I was... I think I was 14, if not 15. Around that age. At this one apartment that I delivered newspapers to, the owner was a porn star. She asked me to come in and we talked and she asked me a bunch of shit about my sexual experience and I told her I had none. She asked if I was interested or not, and of course her being gorgeous and an older woman.
SW: Was she a porn star that you were familiar with?
SN: No, not really. But later that day I told some people at work that and they were familiar with her. They recognized that she was living in this particular apartment building. But she basically seduced me and led me to the loss-of-virginity experience.
SW: Did you continue going there for awhile?
SN: No, no, no. Actually that's a funny thing because I was so scared. At the same time people made fun of me, that was the talk of the company, the talk of the town. And I don't really like the attention so I stopped going. I asked my boss if I could change my route to a different place. And... so that never happened again but supposedly she had called a couple times asking for me. So... that's it. It was weird.
SW: Are you aware of her doing that with anybody else?
SN: You know what, I asked her if she had done this before or not, and she said, "No." But she had this smile that made me think she possibly had.
SW: Afterwards did you see any of her movies?
SN: Yes I did. Yes I did. And she looked nothing like she did when I had seen her personally. Like the level of intensity was completely different. When I was with her she was very teacher-like instead of being really... a slob. I saw her on video once. And that's it, and I never went back.
I remember that it wasn't that good. I was excited and I was as hard as I could get. But I actually... the whole experience wasn't as exciting as I wanted it to be. I asked her... if mine was big or not. Decent size? And she said, "Yes." That boosted my confidence in a way.
SW: Did you remember to collect money?
SN: Yes I did collect money. Yes I did. She was very nice.
MY PARENTS PROBABLY WOULDN’T EVEN BELIEVE ME IF I TOLD THEM WHERE I WAS
Zoe, 18
I was 13, at an Applebee’s with a friend. Our waiter was this guy Troy and I asked him to take me back to the freezer, stick a chicken nugget in my mouth, put my legs behind my head, and fuck me. And he did it. I don't know how I came up with that. I was a little messed up on drugs, high on ecstasy and weed. I used to be a little crazy but I’ve grown up since then. My friend just sat in the booth by herself cracking up about it. It is pretty funny if you think about it. I can’t remember how long it lasted, but I was late for curfew that night.
I’ve settled down since then.
BACK OF THE BUS
Caitlin, 39
It was with my school bus driver. His name was Frank. He was hot. I had been flirting with him probably since I was about 13-years-old. He never knew I was a virgin but I played it off like I was a little slut.
So he came over my parents’ house. Our house people were gone and he brought a friend over. I thought the friend was going to sit downstairs but he was really attractive and I have a thing for black men so we all ended up going upstairs to my mother’s room.
I didn’t look my age back then. I could get into bars. I looked older so I think it made me act a little older. Frank was maybe about 24.
We stayed up in that room for hours. It was the perfect setting for a first fuck. It was the first time I had ever given head. The best thing was that I’d never thought about receiving oral sex, but it happened and I loved it. First time I had ever had sex and I ended up fucking two men at the same time. It was probably the hottest sexual experience I’d ever had. We started and it went on and on and on. The housekeeper came in the next morning. I guess she straightened up after we left and she never said anything about it to my mother.