How to Lose Your Virginity ...And How Not To (23 page)

Chapter 14
"IF I HAD THE CHANCE 2 DO IT ALL AGAIN…
I WOULDN'T CHANGE A STROKE…"

These have a sense of nostalgia. The stories grouped in this chapter are here not so much for what they are but more for the look in people’s eyes as they relived their past. As was indicated to me by Mark, who has the first story in this chapter, "I hadn’t thought about that in years." The chapter title comes from Prince’s "Raspberry Beret" and the line that precedes it in the song is, "They say the first time ain't the greatest… But…" for these individuals their first was a declaration, a realization, a discovery that sex is good, sex can be fun.

THE UNDISCOVERED COUNTRY
Mark, 41
I was 16. My folks let me go on this trip with this friend of mine, which was unique for them, but they let it happen. I think my friend was 18 or 19 at the time. He had a Jeep CJ-5 and we cruised around Vermont, New Hampshire. and upstate New York. We were driving back from some wilderness in Vermont, coming into New York, heading to a campground we had seen on the map. It was maybe 11, 12 o’clock at night and there were these two girls hitchhiking on the side of the road. My friend and I just look at each other. So we pick up these girls, the one was tall and skinny the other shorter and stocky. We took them to our primitive campsite which had a bunch of these three-sided buildings that you just threw down your bedroll in. And we wound up having sex with the two girls, one tall and skinny and the other short and stocky.
The trip was a phenomenal trip. Earlier we were camped out on some lake and I caught some trout, gutted ‘em and cooked ‘em right there and had dinner on the side of the lake. It was such a cathartic trip for a 16-year-old, being out in the wilderness.
This was 1976… 1977, or something like that. And here were these girls on the side of the road. I can’t even remember their names, and all they wanted to do was have sex. They were just waiting for someone to drive down the road, pick them up and have sex with them.
It happened pretty much right away, all of us in this tent thing. There was this uncomfortable switch-over moment and it was raw and strange and it wasn’t like prom night. The second girl was more fun. She had a sexy attitude, I do remember that. That first time it was like, oh here’s this with the first girl then here’s that with the second girl. I probably can’t do the emotion of the situation justice stating everything so matter of factly, it was actually kind of cool. But then we dropped ‘em off at some trailer park and that was that.
Years later I thought back on it, and you know, you have sex with two chicks and you don’t know who they are or anything about them, several states away. You don’t really think of it when you’re 21, or 25, or 29 but when you get to be like 35 you’re like, "I don’t have any kids, but I wonder if I do."

***

I had been masturbating from a young age. And I’m a very sexual person. So it wasn’t a surprise to me that it wasn’t painful at all. It was just amazing… it was really good. I actually orgasmed, which I guess a lot of girls don’t, but I did. And James and I were elated. It just made you want to high five afterwards. You’re like, "sweet." You know? We’re not virgins anymore. Afterwards we just laid there, grinning like idiots. And from then on it was sex all the time.
Rochelle, 24
Lyndhurst, Ohio

***

I LOST MY VIRGINITY TO DONNY SO-AND-SO
Michelle, 35
It was with my best friend at the time. We weren’t dating or anything, he and I were just really good friends. We were out drinking one night, whooping it up as you’re prone to at 19. A girlfriend was driving, designated driver or whatever. We stopped to get cigarettes. Donny knew that I loved strawberries and he walks out with this huge strawberry ice cream cone. He got in the backseat and he kinda like wriggled his eyes at me, so I crawled over the backseat too.
We’re sharing an ice cream cone, our friend is driving, and we started making out. I had never kissed him before. The weird part was we had actually got a hotel room the night before because I was too drunk to drive. We slept in the same bed but nothing happened.
So we’re making out, we’re licking strawberry ice cream. My friend says, "Um, I’m kinda feeling awkward." She was mad because a mutual friend of ours had a crush on him. I tell her to take us to my car. My Chevette was parked facing the beach out where they dock boats in our home town. It starts raining and a Living Colour song was playing on the radio. They were on tour, opening up for the Rolling Stones and had just done an in-store appearance at the Camelot record store I worked at. So I was really into that band at the time.
We finished the ice cream. "Where are we gonna go?" He directed me to a secluded spot and we had sex in my Chevette. July 30th of my 19th year. I always remember the day, I still always kind of celebrate it in a way. Then it happened every day for about the next three weeks. In my car, outside in the park, on the tennis courts.
He drank a lot. He was a troubled guy, a very troubled soul. I think that was part of the attraction ‘cause my dad, he’s a very troubled guy.
Donny moved but I stayed close to his family.
Two years later I was at a party playing "chandeliers" with this girl; it’s a drinking game kind of like quarters. We were drunk at this party playing Chandeliers and this girl flippantly says, "Yeah, well I lost my virginity to Donny so-and-so." And I was like, "Oh my god, me too." She lost hers at 16, I lost mine at 19. We bonded over the fact that we lost our virginity to the same guy and we’re still best friends to this day. She’s pregnant and I’m her birthing coach because her husband can’t handle it.

***

We both decided we were in love and it was the right thing to do. I wanted it to be special so we got some candles and rose petals. We were in my childhood bedroom and we made love. The whole act from start to finish took probably about 45 minutes to get it right. If one of us messed up, we just took time to figure it out and continue.
Connie, 22
Lakewood, OH

***

CRUSHING ROCKS
Paul, 43
I was working as a clerk in some office. I asked a coworker out and on the third date she took me down to a quarry on the south shore, 25 miles outside of Boston. She took me there with the intent of having sex with her. I had waited so fucking long. I was in college, that was a long time waiting. I knew before we even went up there that that was the night. It was just a question of where.
We were on the seaside, sitting on a blanket on a big, flat rock. We got a little high, we had some music, like a boom box or whatever. It was a good time. I don't know how much time went by but all of a sudden the tide came in and the rock path we walked out on was gone. We splashed back to shore and where do we go? We climbed on top of a crusher, this big machine that crushes rocks. That's where we did our business. Sweet and lovely.
Awkward? No. Amazing? Yes. I remember having pussy in my face for the first time and then screwing the pussy right after that. What a moment. It was beautiful, it was more than I could have even hoped for. The girl was beautiful, but it was the desire of both of us to do what we did that made it sweet... smooth... ecstasy. Everything about my first time was superb.
RIGHT WHERE I NEEDED TO BE
Rick, 48
It was in Wolfman Jack’s basement out in Long Island. At the time I was interning for Wolfman here in New York City. I was helping him and his family one weekend move to California. A number of family members came to help and one of them, his wife’s sister, ended up in my bed, in the basement.
It was better than I ever imagined it. It was more relaxed. I performed better than I ever imagined I would have for my first time. It just felt very natural like… this is what men and women are supposed to be doing.
I wouldn’t have traded that first experience for anything. She was very sweet, a real southern belle… and for that moment, you know, it really made me feel special and loved and important. She asked me afterwards if it was my first time and I told her, "Yeah." I think she took it as a badge of honor.
She was estranged from her husband at the time and I was prime prey. She was probably in her mid-20s. I was a young, skinny, long-haired, 18-year-old Jewish kid who happened to be helping out Wolfman. Wolfman found out, but there was no repercussions from it. I think he probably would have welcomed me into the family if that ever came to pass. But I never spoke to her again; it was kind of just a one-time thing.
You know when you hear about most people’s first experiences they’re usually quite awkward… and I felt like… man, this is right where I need to be.
IT FEELS LIKE THE FIRST TIME
Emily, 21
What I consider as my loss of virginity is the first time I slept with a woman. It was her first time as well, although we’d both previously had sex with a lot of guys.
I picked her up at a mutual friend’s party and then we went to a friend’s house who I played softball with. I was a sophomore in college and I had only known that I liked girls for about a month, maybe two. I saw Julie at this party and I thought, "Damn, that girl is hot." I wanted her and the opportunity presented itself.
So yeah, we went back and crashed at my softball friend’s place; it was two o’clock in the morning and everybody kind of crashed out. I hadn’t been drinking that much, but I started drinking more when we all got there. Julie was pretty drunk and sitting on the counter. I stood over by her and she was leaning over me saying, "What do you want to do?" She got closer and was like, "Can I kiss you?" I was like, "Of course. You’re fucking gorgeous." So we kissed and then she goes, "I want to cuddle with you tonight."
With girls it’s sometimes like that, pretty innocent. You’ll talk and spend the night. We went up to a bedroom but this was different, she was a superfreak. Between the door and the bed she had all my clothes off.
There we are, naked in my friend’s roommate’s bedroom. First time I ever went down on a girl. You know basically we’re just fucking because we’re both drunk. My guy friend, Lou, pokes his head in thinking his room is empty and I’m like, "Lou, get out." He was all, "Emily?" because he thought I was in there with another guy. He was like, "I gotta go to work tomorrow." Then Julie told him to leave and he goes, "Julie? Oh, shit. Sorry." He went downstairs and Julie and I had sex for like the next two hours. I did let it slip that it was my first female experience and she hesitated for a second and said, "I’m drunk. I feel bad." I was just like, "Shut up, we’re having fun. I’m drunk, too." Next morning we woke up and Julie walks out of Lou’s bedroom and this girl I played softball with and Julie had known for years said to her, "Looks like you got some ass last night." Julie laughed about it and two minutes later I walked out of the room and everyone was like, "Aw, shit." I busted us out in front of the five or six people there but everyone kind of knew I was leaning towards women. That’s how I erased the red ‘V’ for women, the one that mattered.
Next morning was a little funny. We hung out all day. We went to breakfast and watched a movie with a bunch of people. She was getting ready to leave around five o’clock that night and she was like, "I guess I should probably take your number." "Yeah I guess so." That was it, and we’ve been together about a year.

***

I still love that woman… that was ah… 16 years ago… she was the love of my life and she still is. I didn’t marry her I married someone else. And that’s ok.
Bryan, 35
New York, NY

***

WHAT DOES A KID FROM JERSEY SHOW A WOMAN FROM BOSTON?
Max R, 36
MAX R: I was in high school. I guess she was like 22, 23.
SW: How did you meet this college-aged girl?
MR: I went to a music school, a summer session for high school kids and she saw me. She was pretty aggressive. We hung out a little bit. I think I was too busy. I think the fact that I didn’t like girls at all, that I just liked playing music had a big effect on her. So she kept pursuing me to the point where she had to get pretty aggressive or I wouldn’t even notice her. And then… I didn’t have sex with her when I first met her but she came down and visited me… where I was living.
SW: How far?
MR: I was living in New Jersey and the school was in Boston.
SW: Berklee School of Music?
MR: Yeah, Berklee, of course. So we headed down and one time she came down and visited me from Boston. The bad thing and the most awkward part about it really was that my mom was in the next room. That kept on weighing on my brain a little bit.
SW: She obviously knew some college chick from Boston was there.
MR: Yeah. And that was weird too. Because she had no problem. I’m like, "Mom can Brenda come and visit?" And she’s like, "Yeah." And I’m like, "Really? OK." But my mom is super-liberal and really inattentive as a parent… in terms of like supervision. So she slept over for a long weekend.
SW: Your mom cooked her dinner and stuff?
MR: Yeah, she was totally like, treating her great… even though Brenda was there to devirginize me. My mom was oblivious to that. So was I.
SW: You and your mother are oblivious people.
MR: Yes. Living in a little cloud. I was stoned but my mom wasn’t. So, I don’t know what her excuse was. And so there was one day when I stayed home from school, ‘cause I was in high school still. We started having sex and I was so scared. I’m like shaking and I lied to her and told her that I did do it once before because I knew it was going to be a bumbling mess and I wanted to at least tell her that I wasn’t experienced but I had done it.
I remember sort of just not knowing what to do and I’m like, "Whoa. I’m gonna put a condom on now." And I’m like, "When do you do that?" When is the right time to be just like, "Pardon me for a moment while I do this thing with this piece of rubber."
SW: Had you seen them get put on like bananas or anything? Sex ed. class?
MR: No, I had never had that experience.
SW: Had you taken the time preemptively to read the directions?
MR: I may have practiced putting one on but I don’t remember. And it didn’t matter because I wasn’t even… I couldn’t stop shaking really. It was so much expectation here of my manhood being on the line.
So… we did it and I’m sure it was horrible because she was questioning me afterwards like, "You said you did it once with that girl once before?"
SW: She was asking you names, details.
MR: Right, so then I threw in that I was drunk the first time. Therefore I was even less responsible for what happened. But I remember as I’m fucking her I was thinking I should have been, at the time, in Earth Science class. That’s all I could think about, I’m like, "Earth Science or doing this real cool girl."
SW: What did you miss?
MR: A test. And then I remember after she went home I called my friend and I’m like, "Dude, remember during Earth Science when you were in Earth Science and I wasn’t there?" He was like, "Yeah." I was like, "I was getting a blowjob. And I was thinking of you sitting in Earth Science." And he was like, "Dude, that’s awesome." But it was a pretty horrible experience. It wasn’t the greatest. It was good and bad, you know. It was a mixture of lots of emotions. My mom in proximity wasn’t good. That was bad. The whole mom and sex thing was bad.
SW: She was a stay-at-home mom?
MR: No, she was just home that day. Maybe she was trying to keep me from having sex with this girl. I don’t know. I think that was it. The rest was… Brenda still liked me afterwards and really wanted to continue but… I felt I kind of didn’t really like her that much. She was also so into me that I was like, "Oh, no challenge here." I learned that one early on.
SW: Did you end up going to that school?
MR: No. I had no intention of going there, it was just for the summer. It was too stuffy and weird. And also there was another girl there that was doing the same thing to me. And I was like, "These girls here are crazy. I don’t want to go up there." And then after that I really didn’t have a girlfriend for a couple years ‘cause I just, I was so into music. Girls were such a distraction.
SW: And were girls at the music school you went to crazy as well?
MR: Um… there were like no girls in the school I went to.
SW: Anything else?
MR: I’d like to say in closing that I look back on it fondly. I think it was really fun and I’m glad that she took the time to make me have sex with her. I’d like to thank her.
SW: Just that once.
MR: Yeah ‘cause she came down another time; no we did it another time she came down but she totally went schizo that time. And then we ended it. I sent her packing.
SW: What does a high school guy from Jersey show a college girl from Boston?
MR: Charm, man.
SW: I mean around the town.
MR: Oh. I showed her 7-11. The woods you know where we would stash the beers. The Old Milwaukees under the log. And… oh, and my dad ran a theatre. It was like a cultural theatre. It had jazz and classical and dance and all that shit. So I took her to some of the performances there. And then that was really it, ‘cause I couldn’t drive. She came over and like… couldn’t go anywhere ‘cause she took the bus down. And it never occurred to me to let her drive my mom’s car.
SW: Mom probably would have let her, too.
MR: She would have. She was letting her do everything else.
MANLY DEEDS, WOMANLY WORDS… MARYLAND!
Monica, 25
I had known my boyfriend for like a million years, since high school. We started dating again in my early 20s. We went to the beach on Assateague Island in Maryland one weekend and camped out with a bunch of our friends.
We were both virgins and we were fooling around out on the beach on a blanket. It was three or four in the morning, there was a full moon. There's wild horses out on Assateague Island so the only other living thing on the beach besides us were random ponies walking by.
We didn't plan to do it. It just came to the point where I was like, "I want it." It just kind of happened. Maybe the environment helped, the beach, him, the wild ponies…
UN-CHAPERONED FIELD TRIP
Crystal, 30
I’m from Gainesville, Georgia. Little town an hour northeast of Atlanta. I was 18 and it was with my first boyfriend and while we dated for two years we waited that whole first year. He was very patient.
Dylan had gone off to The Citadel in Charleston, South Carolina. The Citadel is a strange military school. And it was strenuous and rough and has all these crazy initiation things like people beating you up with the flat side of swords. They had this rule where you had to obey officers above you no matter what they said and officers would send the younger guys to places they weren’t allowed to be in and then other people would be there, waiting to administer corporal punishment. It was just crazy, like he was off at war or something. He could only talk on the phone like five minutes once a week so we wrote these letters back and forth the whole time he was gone. And then I decided, OK, I would. So I wrote him a letter and said I was ready, which I’m sure turned into a bragging point him being at an all-guy’s school.
My economics teacher lived in my neighborhood and I had known him my whole life. He knew that Dylan was away, so he offered, "If you ever want to visit Charleston, let me know. I have a condo in Kiawah." I was like, "OK, I’ll go this weekend," and he gave me the keys. Economics was my last class of the day so he let me out early and I drove down to Charleston with Dylan’s best friend and his girlfriend. My parents were OK with it because we had been together for so long. I’m sure they already assumed we were doing it.
We picked Dylan up from school and he looked so different – starved and all muscle, real manly. We went to the condo and I started to chicken out. We had been dating a whole year and I wouldn’t do hardly anything but kiss. He couldn’t stay out of school overnight so we had to take him back. But we got back to his school late and he would’ve gotten in trouble. They would’ve kept him the whole weekend and not let him out again. It was very dramatic. I was crying.
So he said, "I’m not going back," and he went AWOL for the weekend and came back with us to Kiawah where we had sex in my teacher’s condo. We had the beach, each other. It was very idyllic. At that age, you don’t really think of the significance of things like having sex in your economics teacher’s vacation house. I thought it was really funny. But I was terrified thinking about how severe his punishment would be. He got beat up a bit and was given extra duties.
Dylan and I stayed together for another 6 or 7 months. He wanted to get married, I didn’t. I went to college and that was it. Years later I told my mom about it.
Related to the loss of virginity, my dad once said, this was probably the closest he ever came in breeching the subject with me, that you can see a difference in people from before and after. Apparently you start to carry yourself very differently afterwards. That’s gotta be rough for a dad to see that in his daughter.
TRANSMISSIONS FROM THE SATELLITE HEART
Bruno, 27
I was in a high school rock band. And we were going to do like the "Monsters of Rock" in our high school. Like a "Battle of the Bands." I was the singer and we covered the Flaming Lips song "She Don't Use Jelly." That was like our big closer. We were kind of a cover band. We had a couple originals but that was our big one. And directly due to us doing that song, a week later this super-cool chick, Sara, she was already doing drugs and everything, she had sex with me. This was a girl who was way beyond me and my friends. Normally she wouldn't even talk to us. But I sang this Flaming Lips song and she liked the Flaming Lips. But we were at this party at my friend Rick’s house and she decided that she was going to have sex with me that night. She was also on ecstasy. She came over to me, took action, basically took control of the situation and dragged me into the swimming pool. We were having sex in the pool with everyone up in the balcony above us watching us. I was like, "Yeah, Sara Donahue!" I was all psyched about it because here was a girl who would never talk to me. Just recently I actually met Wayne Coyne, lead singer for the Flaming Lips, in LA. He was at the premiere of their movie Christmas on Mars. I talked to him and I told him that story. I said, "It was because of you I lost my virginity with this really hot chick." He gave me a pat on the back and he was like, "Nice, man. Glad to be a part of it."
SAVIOR OF THE UNIVERSE
Niles, 40
I grew up in Sydney, Australia. There was this boy at my school. I liked him and wanted to try sex but he was like, "No. You’re just going to make me say "yes" and then you’re going to make fun of me at school," because I was a jock and he was the gay boy at school who everyone picked on.
We both liked music. That was our connection. So we used to go on friend dates to see like Cheap Trick, or The Knack or whomever. Then I’d drag him to punk clubs to see The Ramones. He used to cry because that the punk shows were so loud. He was more of a disco boy.
One night we went and saw the movie Flash Gordon. Kind of a homoerotic movie. I thought it was horrible but I could see it was working on him. In the movie, Flash Gordon was the quarterback for an American football team and I played rugby which, I guess, got him excited. I can credit that movie and the music of Queen with getting me laid at 14. Rather young but I was pushy and he was cute, so it had to happen. We went back to his place and had sex in the shower. We dated for a long time after that.
THE WAY TO A MAN’S HEART
Sandra, 29
I lived with my mom and my step dad in a country town called Rock Bank. It’s a suburb of Melbourne, Australia of about 1,000 people.
Brent was going to university and boarding with the family next door and my mom really wanted me to date him. She found out he was sick and like the good Italian woman she is, made a bowl of soup for me to take to him.
I went next door with the soup and I asked for an encyclopedia starting with S. I made that up on the spot because borrowing the book gave me an excuse to go back there later and return it. I was just, "Hi, this is some soup and I need encyclopedia S. Yeah, because I’m looking up sea lions for a project and… and I know that you’ve got encyclopedias and I don’t have any." He would take my virginity six months later.
My mother always told me, "If you’re gonna have sex I’d rather you have it under my roof. I don’t want you having it in the gutter somewhere, or in a hotel room, or in a car." If I was going to have it she wanted me to be in a safe place, somewhere where I felt comfortable. That place ended up being my bedroom one night at about one o’clock in the morning.
It bloody hurt. I obviously had masturbated before but I had never actually put anything that big up that section of my body, and fingers can only do so much. But once you get started, you can't stop. Once I got past the whole first experience, I wasn’t just having sex, I was making love.
Then we were having sex all over: my house, the neighbor’s house. Mom finally caught on. One morning getting ready for school I had just gotten out of the shower and she says to me, "Your boobs have gotten really big." I was like, "Oh, have they? I hadn’t even noticed." She said, "No? They’ve gotten bigger in the last few months. They only get bigger when they’re fondled too much." And I was like, "Oh…" She looked at me and asked, "Have you been having sex?" And I said, "Yes." "Well… as long as you’re doing it safely. Just promise you won’t do it in my bed." I never broke that covenant and I had already gone on the contraceptive pill so it was safe.
I ended up marrying the man with whom I had my first sexual experience. We’re divorced now, but we were together for 11 years. I never appreciated anyone else, so over time, you have no one to compare it to. The whole love part of what we had turned into more of a love between siblings than a husband and wife. But I still remember the first time fondly.