How to Lose Your Virginity ...and how not to (Real Stories about the First Time)

by Wickens, Shawn

  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.

  ***

  She had the nicest tits, the greatest tits in the world. I still have naked pictures of her.

  Stu, 28

  Burlington, VT

  ***

  HER SON WOULD HAVE BEEN 16 THAT YEAR

  Jack D, 40

  SHAWN WICKENS: How did you know her?

  JACK D: She was a neighbor and she lived across the street, a hippie from Long Beach, California. I was 15 and she was 42. You are going to love this one. This will be a highlight, will I get a centerfold on this?

  SW: Maybe.

  JD: It's gonna be a phat one.

  SW: Did she have kids or anything?

  JD: She had two children. She was born in 1938. And... one of her children went down with her husband in a Cessna in 1975. So she lost her husband and an 11- year-old child in a plane crash, which left her daughter who was born in '57. So obviously they bonded and melded and tried to lick their wounds and got through it. But she was a very cool hippie chick. And my teacher, so to speak.

  SW: How did it end up happening?

  JD: She was a hippie chick, a hippie freak. Nice lady. Bong hits. Extremely intelligent... I was a naïve 15-year-old, a hippie kid. I grew up here in North Beach. I was a renegade and we just hung out and stuff but she was a free-minded person and stuff.

  SW: You had hung out for awhile before this actually happened?

  JD: Oh, of course, yeah, months. She was my neighbor, she lived across the street and it had to be a dead secret you understand. I didn't know it was going to go in that direction, but when the day finally came it was one of the most wonderful days in my life. And let me add that I was a geek boy as a kid so I had never even been with a girl before.

  So, nice way to break the ice with a lovely 42-year-old hippie chick. I never made out with a girl so you know in grade school you're either one that gets it or one that doesn't. And if you are not, you don't really care because you know you're a geek anyway and it's irrelevant to you. And so there were no big dances, no nothing, you know? You just... eventually everybody's going to lose their virginity. It's got to happen between 10 and 17 (laughs)… those two ages. So I was 15. A very naïve 15, sexually... obviously because I'd never kissed a woman.

  SW: What happened that day?

  JD: The day... for your specifics... we turned the lights down and pulled out the bong and did a bong hit and she put on Pink Floyd and it was just like, you know the usual.

  SW: In the basement or in the living room?

  JD: No. In the living room. Right there in her house, you know. I mean... we'd known each other for three months. So this whole thing built up over three months to the culmination of the... you know… "thing." We were just smoking and I believe I approached her and I just went and got closer and it was wonderful because... I just got closer and started doing a massage. That was my thing. ‘Cause I didn't know what to do... having not done anything before. Facial contact and just sort of this innocent, not knowing what to do and the vibe was there and she was there to accept it and... she took it from there. Not aggressively, by the way. Very, very tenderly and lovely and it was wonderful.

  When one doesn't really know what one is doing one sort of lays back and lets the ol' master... I had no idea what I was doing. Needless to say... if you can relax on your back and let her do her thing... "Oh. Oh my god." Dark room and Pink Floyd is playing in the background and... it was wonderful. And again it turned into a whole summer of... very private... encounters.

  SW: Was her daughter around?

  JD: Her daughter was 23 years old, born in '57. I was 15, I was born in, you know... '64. I had met the daughter, but no. She had no clue and again this was... a very... it was nothing anybody could discuss. It was a very private thing between the two of us, but it was an older lady... stealing a boy's virginity.

  SW: Did it continue between you two after that day?

  JD: Very much so. It was a summer romance, May 27th I believe. You'll always remember your day if it was a good one. And that was 1979 and it went through the summer. This was a very hectic summer as a 15-year-old. The punk rock scene was going on here in San Francisco and I was running around like a wild child. I was a latchkey kid so... doing lots of drugs, very careless... very immature. Very, you know, not bad but just having a good time and obviously the age gap between us... the woman you know she was very much like a mother, very maternal.

  It came to a point, I guess I realized after about a month into it I was very self-conscious when I was around her outside, around the neighborhood, for obvious reasons, ‘cause it was an older adult. The whole situation, it had to be something that was very...

  SW: Secretive; hush, hush.

  JD: Well, sure, think about it… Anyway it went on through the summer and I guess as things advanced... I was having trouble dealing with it. So that was that and I guess it ended around October or so... what I did was I just basically... stopped...

  SW: Stopped going by?

  JD: She would keep calling and calling. I couldn't deal with this. And at the time my mother's drunk boyfriend was at home... like Jack Kerouac, dysfunctional family... he was dying of cancer. I was a freshman in high school and he was literally dying of cancer in my house, I mean chemotherapy and all that stuff so I was obviously going through what I understand now to be a lot of different traumas.

  And obviously with the age difference... I couldn't take it, and I was a renegade. I was running around doing a lots of other things so...you know the combination of all those things when you're 15. But sexually that's the best parachute drop out of a bomber I ever could ever hope for. She was a love, and we were friends for years. And she passed away from cancer just a few years ago. Very quickly. It was really sad to me because I'll always love her, very much. Just, I mean... a mother... a very, very caring person. That was e
xtremely sensitive in a maternal sense to what we were doing. It wasn't a rape. So it was wonderful. And I'm glad you asked.

  CHEERLEADER FANTASY

  Whitney, 23

  It was with my high school boyfriend, Brett. He and I had waited to have sex for forever and when we finally did it, we did it in my house on the living room sofa with my parents asleep upstairs. What I think was beautiful or poignant about it was that it was right after a football game and I was a cheerleader. So it was that wonderful, classic scene of a cheerleader with her skirt up, welcoming her boyfriend. The parents are upstairs sleeping with the door open, completely oblivious to their daughter getting deflowered.

  My first time was really quite enjoyable in every way. It didn’t hurt, I think because I had waited and I felt really strongly about the person. And what a fantasy for a lot of guys to have the cheerleader outfit. My parents weren’t woken up by the sex or by his yelling "I love you" up to my bedroom from his car in the driveway.

  ***

  It just so happened that the hills around here in town, they were on fire. And my whole room was like ablaze orange. And we had been talking about it for a couple weeks, seemed like the right time. It was beautiful because the whole world was on fire at that moment.

  Dion, 30

  Sparks, Nevada

  ***

  CENTER STAGE

  Alan, 48

  I grew up in show business. I was a child actor. By the time I was a teenager I had already been doing shows on Broadway.

  I hadn't lost it yet and frankly I don't like that word, "lost." No, I didn’t lose something, I gained something. So I grew up around sensuality, sexuality. I was a very driven kid through my circumstances of having a career and performing so I wasn’t about going out and getting it on.

  When I was turning 17 I took a job in Nashville as a backup singer for all these famous country singers at the new Opry House, people like Linda Ronstadt, Merle Haggard, or whoever was there. I was doing really well and I was having a really good time. As you probably know you always have your backstage entrance for the talent so every time I would go in, there'd be a huge limo there. A girl, this young singer, would get out of the limo and immediately get rushed away. I think this was four or five months before my 17th birthday. She was coming up on 16. And we were always supposed to stay away from this particular limo, even though we were talent also. I'm going in this private entrance and this limo pulls up everyday and I see this figure, this very young but attractive figure, get ushered inside. She’s in sunglasses, incognito that kind of crap. But I already dealt with that on Broadway. It was nothing new to me. It happened that I started singing backup for this particular artist, this young girl, who I won’t name.

  I was singing backup for her, me and five other guys, but her and I had this attraction. Then it was a passive courtship. We were forbidden any interpersonal contact with her but we were on the same stage every day. I'm doing my thing, she's doing her thing. She was shrouded around by people so there was no way to even say, "Hello." She was rushed in with men in black and did her thing and then she's rushed off by bodyguards. Believe me, her people hovered. I'd just go to the backlot get in my car and go home. But something started to happen on stage where, as a backup singer, I started to pick up more than I was supposed to do. I started to feel her vibe. The way she would move.

  A lot of people got cut because they wouldn't be in sync with her. But I could keep up. On stage, in rehearsals, and sometimes during actual performances, she started seeing that I could pick up the vibe and she would go off in these kind of improvised vocalizations. She would throw some body movement or a sensual rhythm my way. The other guys would be going, "What? Huh? What’s going on?" So we started to get close on stage when the bodyguards weren’t around. It was our only opportunity to connect.

  But it was very, very sensual. And when you’re performing with someone you have to kind of get into the person that you're backing up. You have to really get into their head, get in their body and really understand what's going on. So that was all developing and then we would sneak times to talk. We took more time on stage to check in with one another. We’d steal off to this empty sound stage to converse every chance we’d get. We established that as the way we could communicate behind all the producers’ backs, her bodyguards, everyone watching her.

  We had been rehearsing for three months and performances had been on their feet for one month when we all found out we were going to tape a television special with, oh, I don’t know, like Sandy Duncan and Dennis Weaver and whoever.

  We’re at the after-party, I had something to drink, things are pretty relaxed. My agent isn't watching me and her people aren't watching her. I went to the men's room and I was going to the bathroom in the urinal. I heard somebody enter and the lights went out. I think, "OK what is really going on here? Who’s in here with me?" This is show business, it could be anyone. I’m standing in front of a urinal and this person started fondling me. Then I smelled a familiar scent, it was her. We knew a back way to our soundstage.

  This was my first time and she was younger than me and she guided me, she had a lot of chutzpah. We made love and that was my first time and we arranged it with the bodyguards, my agent, my producer that we could spend time together.

  After I lost my virginity, or after we gained that from one another rather, it was difficult to hide our emotions. But it was less difficult than wanting to be together and not being able to. We had our secrets and we had our fun. We had our people who kept them for us, the one bodyguard who would slip her through to my place. It was very sweet, very fun, and very titillating.

  SLEEPAWAY CAMP

  Eileen, 21

  This happened in Arlington, Virginia. I was 17 and I entered a summer program called Governor’s School for the Arts. It was a month-long program paid for by the state where we took a lot of classes and went to lectures. I was there for visual arts studies and this guy I met was there for humanities.

  The first time I ever met Tommy he was sitting on a couch and I was laying sort of underneath him on the floor with one of my friends. She and I were goofing off, being giddy girls and I accidentally licked his leg. I was pantomiming like I was going to lick his leg, but I overshot it and actually did lick his leg.

  My friend was making fun of me: "Oooh… you guys are smitten. Oh." And I was like, "No. It was just a mistake." I still hadn’t seen the guy at that point but then I sat up and we looked at each other and shook hands and shared a "Hey, that was a little weird." After I noticed him I did get really sort of interested in him. In the long run it turned out to be an effective way to meet someone.

  That was halfway through the program so there were two weeks left. We dated for awhile long distance, this was in July, and then I went to visit him in mid- August and stayed at his parents’ house for a week. We were very awkward around each other. We hadn’t seen each other for about a month and we were trying to catch up, but when we kissed it felt strange because his parents were always around and they were very, very strict. We could never schedule any makeout time or anything.

  Towards the end of my stay a bunch of us from the program were having a bit of a reunion and went to see Rocky Horror Picture Show, all dressed up and everything. I didn’t know any of the characters or anything because it just so happens I was also a Rocky Horror "virgin", so my costume was pretty generic, lots of black and fishnet.

  After the movie we all headed back to another guy we all knew from the program, Jamie, to his house where all of us were staying for the night. We were all drinking or smoking or sort of lounging around. I had to leave the next morning and my dad was picking me up at eight in the morning to go spend a month in New England with my grandmother.

  So me and Tommy were hanging out on the porch swing, our last night together. Everyone else went inside to get stoned in Jamie’s room, which had a window overlooking the porch. Tommy and I were on the porch swing making out and slowly we start losing clothes. People were laughing
at us through the window and at one point he threw my bra at them.

  He asked me, "You’re on the pill right?" which was responsible of him. I think that was his way of opening up a discussion on sex. He could tell something was wrong and I did have a really bad headache and he says, "Well… you know what’s good for relieving headaches don’t you? The female orgasm." I just started laughing and we started kissing and more clothes came off and that’s when I thought, "Oh, he wants to have sex with me. We’re gonna have sex. Am I ready? Do I wanna do this?" I had chances before to sleep with other guys and I always thought I was ready, but none of the previous guys were ready because they were immature assholes. Tommy was different and while we were there on that porch swing I thought back to earlier that day when we left his house. He had picked up some book I was reading and he was like, "Do you want to take this with you?" I thought that was thoughtful how he would notice and mention a thing like that so I thought, "A guy who would do that, yeah I’ll have sex with him." There was lots of fumbling until we actually got it. It was pretty early in the morning and while we were having sex I could see the next door neighbors come home and walk up their steps. I forgot about the headache, but only because the pain went elsewhere, so his method didn’t completely work. Oh, and there was a full moon outside. Afterwards we were laying there being kind of quiet and then I was like, "That was my first time." Then he said, "Mine too." I burst out laughing, I didn’t know we had both just lost our virginity together. We sat out there for a long time and just talked, it was really nice.