How to Lose Your Virginity ...And How Not To (28 page)

It all seemed ironed over but then the next week her parents told her she couldn't stay at their house any longer. I have an apartment above my restaurant so I said, "Lindsey, why don't you stay at my apartment? You can stay there." The next weekend after that, I was over at my own place and she came over because again, her parents kicked her out. So I said, "Come up." I really didn't think anything of it. We watched Young Guns, but really didn't watch that much of it whatsoever. We didn't do anything, we were just talking to each other and she's telling me everything about what's going on in her life with school and all of her friends. I just listened to everything she had to say and the movie went by real fast.
I was 35, almost 36. She was 20. At that point in time I just thought of her as a really great friend. Another week goes by and she's at her parents’ house and everything sounds fine and then the next weekend she says they're not going to let her stay. During that time there was an oven explosion in my restaurant and so the whole side of my face was burned and my ex-wife couldn't even care less, made no effort to do anything for me... and I could have died.
So I was in the hospital, got morphine and everything. Lindsey and I hung out so another week goes by and once again she can't stay at her parents’ place so I let her stay at the apartment. The only thing is, I'm going to be there too since I was laid up from the accident. So we're sleeping together, it's a king-sized bed, plenty of room. She asked me for a massage, which I’m actually in school for massage so the request itself was nothing out of line. I give her a massage and again I had no intention of anything and went to sleep. Then in the middle of the night she woke up and she told me that she always had a crush on me and she wanted to know if I found her attractive and, "Yeah, you're beautiful." We kissed for a while.
It felt a little weird being on the opposite side of the age thing. I told her there was a big difference in experience. And her at 20 I figured she could have only been with a couple of people at that point and whether I should have only been with a couple people well... I'd been with a lot of people. She told me that she’d only slept with one person. I was like, "OK. I understand that, but there's a difference between a high school-aged boy or a college-aged boy and a man who's slept with as many women as I have."
So we didn't do anything, we kissed, we held each other. I told her that I love being with her. We had a great time. The next weekend was my birthday. I turned 36 and she came up to Portland, Maine, with me and we spent the night together. And that was the first time I made love to her and it was obvious to me that the one guy she'd been with really didn't know what he was doing. Later I found out that she really had never slept with anybody. She had gone down on guys, they'd gone down on her but nothing else ever happened.
And we made love for hours and it was enjoyable for her. It was enjoyable for me. I had a wonderful time making love to her. And she is an incredible lover, but the thing is, it took a long time building up to the point where almost a month from the first time we really admitted to having a sexual attraction for one another to the point where we had sex for the first time. I mean we had done a lot more, we had kissed and touched each other, played with each other. There was a lot of intimacy that led up to it which, for me I think, it was like I can give you something as opposed to, you know a 12 or 13-year-old girl having sex with a 13-year-old kid and neither of them knowing what the hell to do. But for my first I had a woman show me exactly what was supposed to happen. So I knew how to show this young woman.
We’re still together, but the hardest part now is that I kind of want her to experience other possibilities. That’s a difficult position for me to be in. I was the first guy that she ever was with and, oral sex, whatever anyone wants to say, I mean, Bill Clinton was right in that aspect that it's really not sex. It's sex but it's not sex. And for someone like myself who's been around and seen what the whole world of sex has to offer... I can give her me but I can't give what everyone else gave me. It's hard.

***

I would never again want to take someone else's virginity…
I felt very terrible about it. It wasn't a good experience for her and I just wanted it to end. It wasn't sexually turning me on because it was hurting someone that I felt for.
Randall, 22
Houston, TX

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Chapter 18
"I DID IT MY WAY"

Though most of my road trips for this book were solo trips, they felt more purposeful than any other vacation I’ve taken because I had a specific purpose for traveling instead of sightseeing. And I feel an analogy can be drawn between my positive travel experiences with some people’s good first times – if you set out to lose it, just get it over with, that’s most likely exactly what it will feel like. But when approached as, "I’ve given it some thought, this is who I am, and this is how it will best work for me," "I’m finally going to discover the mystery that is sex," "Here it is, the beautiful act that inspires some people to compose songs, write sonnets, paint or sculpt the human form," "I will need training wheels at first but I’m still going to enjoy it," the experience ultimately benefits. Journeys with intent illicit better results than just going through the motions. How you see it is what you’ll get out of it. And while we may not have as much control over when it happens as we may like, we do have control over our attitudes towards it. That not only applies to the first time, but every time.
One aspect of these interviews I didn't expect to find was individuals who knew what they wanted, knew how they wanted it to go down, made a choice and went after it. In these instances, I've found those who defined the parameters of losing their virginity had more positive experiences. Confidence breeds success. Knowledge is power.

ON MY TERMS
Rebecca, 38
We met these guys dragging in Douglass, Kansas, which was where the closest drag strip to Wichita was at the time. I just woke up that day knowing that I was going to do it and it was simply a matter of finding a stranger. Virginity to me was a power thing. I didn’t want any of the guys I knew to have that much power over me so a girlfriend and I picked up a couple of guys to have sex with, which nowadays is stupid.
We were all driving around, flirting, hanging out of the cars and we ended up out in the country, right in the middle of an oilfield, right next to the pumps. As those oil pumps were moving, so was I. He was a complete stranger, it was happening there and then because it was my choice. My way, my time. My friend had already lost hers at like 14 or 15.
I never gave in to peer pressure or anything like that, and sex at the time wasn’t a big issue to me. I was 18; I was going away to college. It was more of a control thing. Other things were happening at that time that were beyond my control. My parents were getting divorced and their separation was a loss of control, a loss of what I knew. Losing my virginity in this manner was purely a way of controlling what I could – the how, the when, the what and the where… with some guy whose name I do in fact still remember. So it was a very conscious, non-emotional choice. The love thing wasn’t important to me. I was watching my parents fall apart so love wasn’t the issue. It was control.
There was a lot happening then. I was going away to college and a lot of my friends were staying in a small town, getting married. I didn’t want that. I left town and went to college and did it all my way.
ELECTORAL VOTES: 286 TO 251
Lana, 18
I met him at a protest march for peace around a year before I ever started dating him. Then afterwards there was a show put on by the local S.P.A.R. organization, Skinheads and Punks Against Racism, at this American Legion hall right outside Philadelphia. Everyone went to the show after the rally.
I’m not really sure when I decided he was the one because he was tall and very muscular; me – I like lean guys like around 130 lbs. But he’s really an awesome guy and had a lot of respectable views on the world and actually followed through with being active on achieving goals and stuff. So I was attracted to the fact that he was ambitious and going to school for what he wanted to do. And punks aren’t usually the most ambitious types, but he was a nursing major at Drexel which I thought was productive. We dated for about a month and then came Election Day for the 2004 Presidential Race.
I wanted to have something beautiful to look back and remember other then Bush getting reelected – one good memory before everything just went completely downhill. It went down in a Drexel dorm room. I didn’t go into it thinking it was going to be amazing or anything. I just wanted it to become a good memory. Aside from it being in a Drexel dorm room, ‘cause what’s grosser than having sex in a dorm room, it didn’t really change the relationship any. I had waited awhile and we had known each other for so long. Then later that day, of course we found out that Bush was reelected. But I still have that nice memory, which is awesome and exactly what I wanted.
It was pretty weird because the whole thing was planned and most people don’t plan out that type of thing. He was actually really unsure about whether or not he wanted to be my first because it wasn’t his first. I told him I was ready and that I wanted to do it on Election Day because we were going to hang out that day anyway and it was just to have one day together as crazy youth before the election. After we finished he asked me if I was OK, then we cuddled and fell asleep.
It was horrible sex. He was a very large black man and it was my first time. I never enjoyed it with him the couple more times we did it and I was afraid I’d never enjoy sex after that. But all in all it was a pretty good experience. I didn’t go into it looking for love or for anything magical or life altering. So I guess waiting all that time and going into it with clear knowledge of what I wanted was the right way to do it.
THE COUNTERFEIT PEN PAL
Brenda, 35
I decided to lose my virginity before the legal age which, in England, is 16. On a whim my friend and I bought this youth hostelling magazine so we could flip through the personals section in the back - man desires woman type of thing. Terribly exciting reading for 16-year-old girls.
I thought, "This is the way I can go about it. This magazine is how I’m going to engineer it." And so I found this listing by a bloke in Rumford, which is not very far from where I lived.
I wrote him and we had a very long correspondence for about two or three months. His letters came and I had to quickly rip them out of the envelope and transplant alternate letters that I had written with different handwriting inside, so that my parents didn’t realize what was going on. I told mom that this pen pal Neil was really Natalie and that Natalie was in a wheelchair so she couldn’t possibly come to visit us. There was a lot of subterfuge going on. And it worked.
So I went to visit Neil or "Natalie" in Rumford who turns out to be a 35-year-old physics teacher. He didn't know I was 15. I lied. I pretended I was 18. Very, very bad of me. But for sure he knew that I was 15 before the dirty deed was done, which I thought was slutty fun.
He did this funny thing… this really bizarre thing like how teenagers play games and throw dice to take their clothes off. And I thought it was really odd for somebody his age to be into that. And so I said, "Let’s take our clothes off already. Let’s not bother with this bizarre thing." And so we went up to the bedroom and we had sex.
Funny enough I had no idea about orgasms. When I took my knickers off he started rubbing his penis up on the outside of me. I thought it was really fruity. I was very disappointed by the whole thing. I thought that the whole thing was a bit overrated, but I was pleased that it was over and done with and I felt terribly naughty – that thrilled me.
Then he kept writing to me, and I thought, "No, I don’t want this anymore," so I wrote to him that my parents had found out about him and that they were going to write to his school if it continued. I can’t believe the trauma that must have put him through. But I did what I set out to achieve and I did it in the best way I could think of.
PRACTICE MAKES PERFECT
Carrie, 30
I’d been dating a guy on and off for six months. I lived in Boston and he lived in New York so it wasn’t that serious. I was in college and I was dating other people so it didn’t really matter.
Then I moved to New York and he and I became much more. I realized, "My God, I’m a virgin. And this guy is like 12 years older than me… what the hell." I didn’t want to be inexperienced with him so I went to a party one night and I was like, "OK. Who am I gonna lose my virginity to?" It was so planned, not romantic at all. I literally went to a birthday party thinking, "Got to get this off my list."
So I met this guy and he was so very, very into me. He was really, really, really nice and very doting. We were at a bar in SoHo called Match and there was a sushi bar upstairs. We were eating and I mentioned how I really liked this flower arrangement on the bar and he paid the bartender for it.
So I slept with him. I was sober. I knew what I was doing. I don’t know how other women react to the first time, but I was weirded out with it. It did hurt, but it wasn’t excruciating.
The next morning he was totally nice but it was kind of sad. He was like, "Let’s go to brunch." And I was like, "Actually I’m meeting my boyfriend." I felt really gross about it, but whatever. At least it wasn’t with someone completely random; he did know my friends.
I always had this weird thing that I never wanted to sleep with more than 10 people in my whole life, so I don’t even count the first guy ‘cause it was such a non-event. Maybe a month later I slept with the guy I had been seeing and I was like, "Ohmigod. This is the real thing." We talked about it later on and I was like, "Did you know that I was a virgin?" And he was like, "Of course I did." He thought he took my virginity from me, but he so didn’t.
CAN’T YOU TAKE ANYTHING SERIOUSLY?
Kate, 21
I was 18. I wasn’t the girl who thought it has to be special; I just wanted to trust the guy. Bryce was like 26. I worked with him at Papa John’s and I knew I could trust him.
He was dating another girl but he told me he loved her like a sister. He broke up with her so one night we were driving around and I was like, "So…" He asked, "What do you want to do?" I’m like, "Let’s have sex." He’s like, "Really?" And I say, "OK."
We couldn’t go to my house and we couldn’t go to his because he had moved out of his ex-girlfriend’s place and was temporarily living with a friend and only had a twin-size bed. We stopped by my house and got my little sister’s Green Bay Packers blanket; some day I’ll tell her what I used it for. We take her blanket and we’re searching for a place to go and we find this court in a subdivision that’s being built. He and I go into someone’s future walk-in closet, lay down and we started going at it.
I’m kind of a jokester. There’s this part in the movie Buffy the Vampire Slayer, not the TV show, when Buffy is killing the main sidekick of the big, main vampire guy and the sidekick won’t die. Buffy is trying to kill him and he’s going, "Ughhhh, Arghhhhh, Uhhhhh," and he just wouldn’t die. When I was having sex, for some reason that's what entered my head so I'm like laying there and he's like, "This is deep penetration," you know kind of as a joke, so I was like, "Eeeeeeee, Oooooo, Ughhh," every time he went in.
So it was awkward but he was experienced and knew what he was doing and that was a good thing. We finished and we left the condom for the new homeowners or the construction guys to find.
I later on went back to see what the street was named: Homefield Court. It was in a development near a baseball stadium so all of the subdivisions had names that had to do with baseball.
A CAUSE FOR CELEBRATION
Grey, 55
I was always friends with females but I never, ever wanted to have sex with a female. I always considered myself a female. And apparently everybody else in high school did too. They were all assholes to me. Those people were all absolutely awful to me.
I was 18 at Western Kentucky University. I never had any sex with a man but I wanted to. I went into the student union men's room and there was this thing written on the stall door advertising, "If you want a blowjob, meet me here at 7:30." I thought to myself, "Well I don't really know what a blowjob is, but I'll be there." I waited and this old guy, well he was probably like 27, but in those days 27 seemed old to me. He was 27 and still a student. I think he worked and was going to school part-time. He walked into the men's room at 7:30 and back in 1968 that was about the best a gay man could get in Kentucky.
There was no real conversation except, "You want a blowjob?" "Yeah, that’s right." "OK let's go." We got in his car and drove around in the country, which it wasn't too hard to find a secluded place in Bowling Green. He blew me and I came in his mouth and I remember Dusty Springfield was singing "Son of a Preacher Man" on the radio as I was getting my load off. I'll always remember that song playing as I’m shooting my first load.
I thought that I should probably kill myself after that because I had never done anything so sinful. Now, believe me, so much water has gone under that bridge.
He didn't ask me to reciprocate or anything and I never saw him again. Although I did put my mouth on his penis. I really wasn't too sure what in the hell that was all about but he asked me to do it, so I obliged. I didn't suck it and he didn't cum in my mouth.
I 'm telling you, that was about the only way you could do it in Kentucky back then. I'm what they once called a "tearoom queen," ‘cause if you wanted gay sex you went to a public toilet. There were no gay bars.
But that happened on December 9th, 1968. Of course I remember the date because I was so eager for it. I come down to the pub all the time now on December 9th to celebrate. In fact, I come down to the pub almost every day to celebrate because I'm gay!
EXPLORATION
Cliff, 39
This is the story of a man who in the midst of a great 10-year marriage that produced four wonderful children just got the idea that he’d like to try something new.
We lived in a small college town and there was a local, gay club my wife and I used to frequent because the best dancing and the best dance music is always at the gay clubs. They did drag shows on a regular basis and the queen of the drag queens, the most beautiful girl there was a girl named Chastity. She had beautiful breasts, was very, very feminine all except for her penis and I have to admit that I used to enjoy a little bit of the male attention from her and the rest of the queens.
One night after my wife and I somewhat amicably decided to get divorced, I went down to the gay club with the intention of seeing Chastity and talking about that evening’s events. I always tipped well and she had kind of a rapport with me from previous shows my wife and I had attended. I told Chastity that I wasn’t going home that night because the marriage was over and she invited me back to her place. She invited to take care of me and she did.
She stayed feminine the whole time and she was wearing this beautiful lingerie and we made out and it was really great. She was so soft. She gave me probably the best blowjob I’ve ever had in my life. It came to the moment when she took my hand and guided it to her penis, and I call her a woman because that’s basically what she was except for that one part. It was incredibly scary, but it was erect and it was beautiful. It was a giant clitoris and it scared the hell out of me. I put a condom on her, put her penis in my mouth and sucked it like it was my wife’s breast. It made me feel pretty incredible and set me free.
WITH A SIDE OF BACON
Annie, 27
In British Columbia. Let's see, I was 15 and I was a waitress in a little diner. My boss, the owner, was the guy’s mom and he was a dishwasher.
What can I say? We had sex and then we considered ourselves boyfriend / girlfriend. It was in a mobile home, a trailer, three weeks after meeting him.
The evening was planned and in the back of my head I had already been thinking of it as a possibility. I was so ready. I was so curious, I wanted to know that part of living so when he made all the moves I just followed along, went right with it. And yeah, it was good.