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 ba
ck 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.
Beforehand, I told him that, "OK I've never done this before." He said, "No worries. I'll just take it as far as you want it to go and I'll stop when you want to stop." He was really good that way. Then of course the issue of contraception and birth control came up and we did it responsibly.
Afterwards it felt really cool. Almost like I had passed a threshold and I was now a woman.
I was in a state of euphoria. I felt high. I was high on life. Nothing felt harsh. Everything had this beautiful hue, like looking through rose-colored glasses. The world was good.
I know a lot of girls have had bad first experiences but I had a good guy and I was ready for it. A lot of bad first experiences probably happened because the girls weren’t ready or the guy just wants to get laid and they're not considerate. I don't know; I had a good one.
My parents were split up and I was staying with my mom. I was visiting her for the summer. My father had a slight issue with it when he found out because the guy was 21 and I was 15 and he said, "No way in hell." And I said, "Well, it's already a done deal so... meet him and deal with it because you can't turn it back and fix it. So deal with it as a parent from that point on." He met the guy and didn't like him. But it all went well I guess you could say.
I had a great experience and it was because I was ready and I had a great guy who gave me a good time. And that's what you should wait for.
***
He eventually sort of became of the mindset that we were having some sort of relationship. Two weeks after it began he was like, "Oh, I ran into my ex-lover and I’m moving to San Francisco." I was like, "Dude, this meant nothing. You were practice."
Isaac, 41
Chicago, IL
***
LAURA’S STORY
Laura, 37
The first person to take my virginity, and I say the first person to take it because I choose to think of the first person as being the person that I loved and cared for. However, the first person to take my physical virginity was a nasty and horrible situation. I still look back and think that was really strong of me not to consider the horrible experience to be my loss of virginity.
At 15 I was pretty brutally raped. I was cut, beat up, everything. The choice was taken away from me. It wasn’t until I was almost 19 that I chose to think I really lost my virginity, by my decision, with a person who was smart and attractive and I very much loved and who I dated for almost a year before we had sex.
He and I used to park, that was the big thing for us, and we would maul each other, do oral sex. The first act of intercourse happened on one of the cold, winter nights we were parked at a golf course, ironic because neither of us played golf. We had been talking about sex for months. I thought my own reticence to have sex was odd or unnatural but I learned that he, having not gone through anything violent, was just as reticent as I was. I feel he would have been equally hesitant had I not gone through something nasty, so that made it special. He didn’t treat me like some mental patient. He knew about the rape and we both agreed wholeheartedly that that shouldn’t mean anything. He was a virgin for real so the first time was really important for the both of us.
It was classic. This was in the dead of winter up in "Siber-acuse," upstate New York. We were in a dumb car with this stupid stick shift and as the moment approached we took a time-out and talked about it and we asked each other, "Is this OK?" We loved each other and it was tender and emotionally wonderful, while physically it was a little awkward and scary and frankly not very satisfying. As a woman it hurt. I think for a lot of teenage boys, sex is just masturbating into a woman. They don’t understand that women have different equipment down there that needs to be serviced a little differently. It was cold out; I’m sure that made things difficult for him.
After the fact, I jumped out of the car to pee and I saw blood in the snow, which was a little confusing since physically I wasn’t a virgin. But on an emotional level there was a relief like, "Wow. We finally did it." It wasn’t kismet or anything but it was an important milestone in our relationship and it felt that our relationship had transgressed into something bigger.
Immediately after though, it was awkward and silly and stupid. It was a silent car ride home. Even the next morning when we called each other, we were really awkward toward each other and we had never been awkward with one another. And the truth of the matter was the reason we even had sex was because we were so comfortable with one another. The first time was so bad and fumbling that it turned into an inside joke between us. The first time is never good but it always gets better.
I think it’s important to note that this is a person I did not go on to marry. There was no fairytale ending, but he remains a friend to this day. We still talk and send the occasional email.
My first time was sort of a dual experience. There was the person who I loved very much, and there was that person I didn’t even know, that evil, nasty piece of work who put me in the emergency room and almost killed me. But I refuse to allow the bad rape situation as the defining moment.
***
I’m glad I waited. I’m now a big proponent of doing things when they feel right for you.
Rose, 35
Milwaukee, WI
***
CONCLUSION
If you picked up this book as a virgin looking for definitive steps as the best way to lose it
, hopefully you were guided in the right direction. Ultimately, you yourself know the best way to lose it for you. As interviewer and editor, here is what I learned: First, women like to talk about sex, just as much if not more so than men. So, if on the cusp of your first time and you have a partner picked out, you’re both probably nervous. Thus, talking about it is a smart move. For one thing, it’s good to be on the same page about how each of you feels regarding the possibility of sex, what you want out of it. You might even find that it’s something your partner enjoys talking about. It’s important to be truthful with yourself and the other person about what you expect. If you are looking for love then it will most likely work best if your partner feels the same way. If you are just looking to get the first time over with than a partner who has the same attitude would most likely produce the best results. I have found through many of these stories that a shared outcome, an equality of desire, so to speak, makes for positive memories. One person wanting love while the other just wanting a lay leads to hurt feelings. Honesty is the best policy, and that holds true in the bedroom. Granted, sometimes you will find yourself in a situation where a partner has been less than honest about their intentions in the bedroom (or even beyond), but perhaps they were unsure of what they wanted. There exist plenty of examples within these pages of first times that did not go as planned, felt wrong, or lacked the magic they were hoping for. We can’t always choose where life takes us, but we can choose how we handle life , how we respond to these situations. It is possible to grow from a less than desirable first time into a sexually capable individual. If it was bad once, it does not have to be bad the rest of your life. Even some of the interviewees with traumatic loss of virginity stories, after time and support from loved ones, have grown from the past into a healthy present and future. So how do you lose your virginity? It probably can be easily summed by quoting the Golden Rule, Aretha Franklin, and any number of Beatles songs... Honesty, R-E-S-P-E-C-T, Love.
How to Lose Your Virginity ...and how not to (Real Stories about the First Time) Page 28