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

by Wickens, Shawn

  ***

  I'm glad it wasn't an American Pie-esque exchange of, "I love you" for having sex. I somehow managed to say, "I love you" a few weeks after having sex. I wouldn't have minded saying, "I love you" earlier; it was just very important to me that those two events not happen at the same time, because I felt like it would have been some sort of bizarre prostitution of exchanging one thing for the other.

  Drew, 21

  Metuchen, NJ

  ***

  THE MOVE

  Roy, 44

  I was away on holiday with my brother and his friends in Mallorca on a two-week package tour. On the second night there I left a disco with this English girl. I literally just ended up with her. She pulled me into a field, pulled my trousers down and gave me a blowjob. Then she pulled me on top and I rid’ her.

  The one thing I remember is she tickled my balls, which was unbelievable... the balls. That was just something else, you never would have expected that.

  She was English, I’m Irish. She was 17 and I was 15. I went back home to my girlfriend after that and I was a different man. I was ready for sex. We never traded numbers or nothing, it was just all about the riding. It was excellent. I’m actually embarrassed that I don’t know her name. But she was short with blonde hair. She wasn’t great looking but she was all right looking. She was nice and funny and nice to talk to. And she tickled my balls… that was the big thing, tickling the balls, man. That made my ears wiggle.

  FATHERLY ADVICE

  Leif, 22

  The first time was with a hippie chick. She was quite a hippie so naturally she was… natural down there. Quite a forest scene down there. I wasn’t ready to go down on her, couldn’t handle the oral thing so I figure we’ll get into some regular penetration. I put the rubber on, started going at it and five, maybe ten minutes into it, the condom kind of got wrapped up in some of her hairs there and sort of got whipped right off. I had heard that it’s possible for condoms to slip off inside and that’s what I figured had happened, but when I looked down and saw the actual entanglement situation, I was a little disturbed. It broke the mood for awhile. We hung out for a bit, smoked some weed, then got back into it after about a half hour or so.

  It finished well for me but I did have to do some mouth work on her after the fact to make sure she was satisfied. My father once gave me some advice that I’ve always tried to follow. He and I were in the garage sharing a cigarette and drinking some whiskey and he just randomly said, "You should never enter a woman unless she’s had at least two orgasms." He’s a smart man, works in home health care so he’s got a mind for knowing what people need and getting it taken care of.

  It’s easy for a man to get off whereas women, there’s more work involved. If you’re going to get off, you might as well put in the work beforehand. So I made sure by the end of the night she at least had two.

  THE INSTRUCTION MANUAL

  Mark, 21

  I was eighteen and my girlfriend at the time and I were at my dad’s house in Cape Cod, Massachusetts. She had done it before, which felt weird. I was really kind of nervous, like a stage fright sort of feeling. It wasn’t like a losing-an-erection type of nervous but it was a definite intense anxiety. But she was extremely patient with me. Before, during, and after the act there was feedback and instructions. She was a feminist organization leader at Penn State and coincidentally a very good sex coach.

  One of the things she told me was that a lot of guys will tend to just thrust downward: up and down, up and down. That doesn’t really stimulate the clitoris. The way she described it was, for guys it feels good when they’re pushing down, but for girls it feels good when the guy is pushing up. She got me moving in that motion and she was right. It’s made all the difference in my experiences with her and every girl I’ve been with after her. I’m not bragging but girls tend to like that better than the "Wham, bam, thank you ma’am" type of thrusts.

  Losing my virginity was a little bit of a bigger thing than I thought it would be. It’s an important physical kind of rite of passage of sorts. And you want to do it well, you want to do it right.

  We did it that first time and it was fun, but it’s a difficult thing to separate the anxiety of the whole situation out of it. The next time we did it, and I know this sounds counter-intuitive since guys are horny all the time, but honestly I was still nervous about having sex. But with her help I acclimated to it and she was a good coach.

  LIKE A WALK IN THE PARK

  Ann Marie, 31

  I was 13 and I lost my virginity at a carnival, like a little street fair in my neighborhood, to a boy that was actually a… OK, he was a carnie. And I lost my virginity in a broken, unused tilt-a-whirl car inside the back of a semi truck. For some reason I just thought that was the biggest, greatest idea because you know, you’re in middle school and everybody’s talking about boy-girl stuff. And I was just, "Well what’s the big deal? I’ll just go do it." And so I found the quickest, easiest route and it was a little carnie kid who was 16, just hittin’ his puberty and I think he may have lost his virginity that day too because it sucked. Not that it ever got better for me ‘cause I’m not about the guys. I can’t remember exactly the name of the festival or where it was located. To be honest, being 31 now, I try to block it out sometimes.

  The kid was working on the tilt-a-whirl ride. The whole thing was his idea. He was like, "Well, you know my boss isn’t here. I got a place for us to go." I don’t have a clue who he had running the tilt-a-whirl cars when he wasn’t there. Those people must have been on that tilt-a-whirl ride for like a good 10 minutes, not even ‘cause it was like maybe a five-minute walk to the semi truck and then it took 30 seconds long and then we walked back. The walk was pretty much the whole duration of the time we were gone. I mean it was like barely touching one another. He wasn’t even a one-minute man. That’s how I lost mine and I promised myself that I wouldn’t do it again ‘cause it was just horrible. I tried with a few other boys and then I met the first woman that I slept with and then it dawned on me, "Yeah, I’m not supposed to be having sex with boys ever. I’m supposed to be a boy."

  So a couple years later I met the first woman I slept with. I was in a park and she was rollerblading and she ended up falling near me and I helped her get up.

  She kept saying that her ankle was hurt and I was like, "OK, it’ll be all right. I’ll help you to your car. Maybe you should go to the hospital." I could care less, to be honest. I just wanted to leave with this pretty girl. I was like, "Sweet. She’s got a convertible and she’s pretty. I’ll sit in the car with her." Well we didn’t end up at the hospital. We ended up at her place. There wasn’t anything about her that said lesbian, specifically. There’s just that thing inside you that says, "This is one I could hit on." In the car I was kind of like playing around with her neck and telling her, "Oh, it’s going to be OK. We’ll get to the hospital." Then I was like, "Oh, I bet you have your own place." She was about 12 years older than me. I was like, "I bet it’s cool having your own place." She’s like, "Well, yeah." And I was like, "Maybe I should see it sometime." "Well, we could go there now." I was like, "Sweet. I’m ready."

  In all honesty I barely ever count the first time on the tilt-a-whirl as the actual time because it did absolutely nothing for my sexual development whatsoever. It was just something that closeted me more. But as far as with the woman that I slept with, I just remember feeling a big sigh of relief.

  It was clumsy, but it was good. I was like, "I think I know how to take off pantyhose." I ripped them off. I was good at that." I mean, I can’t get the crap on but I can get the shit off.

  And it dawned on me that guys weren’t really what I was wanting. It was one of those things where, your first time you hope that you feel like you’re on cloud nine, and it should be totally exhilarating and that’s what my first time with a woman was like.

  She gave me a ride home, at which point my dad asked me, "Who was that?" I was like, "I don’t know." "Then how did you get in her car?"
"I… I don’t know, Dad. I don’t. I have no clue." And I hid in my bedroom for the next few days. I was a little creeped out afterward. When I was growing up you generally didn’t really talk about stuff like that when I was growing up. So I didn’t really exactly know how to define what happened so I went into hiding, kept a little to myself until eventually I decided, "That was good. I want to do it again." I was a little monster from that moment on and hitting on girls at the mall and taking girls home. Then I went to college and that was a free-for-all.

  REFLECTIONS

  Tiffany, 29

  I explain first time sex as a pain you can take. And you do it over and over and over again until you’re good at it. My boyfriend was 19 and he had a very big cock.

  It happened in his bedroom on his waterbed. At 16 I was truly too immature to have sex. When I went home I looked in the mirror and I thought, "Do I look different? Are people going to notice? Are people gonna think I look cool? Am I a woman? Is this normal?"

  I called him up crying because of course I started to bleed. We talked and he was sweet about it.

  ALL-NATURAL LUBRICANT

  Kristen, 30

  I was not necessarily conned into it but... I was. I was 18 and I wanted to make sure I turned 18 before I did it. I had had earlier opportunities but I wanted to wait until I was a little older. I was saving it for a graduation gift to myself.

  I had been dating Rob for awhile, through most of high school. I was like, "Well I want to move to the next step." We go to the beach: Wildwood, New Jersey. We were sharing this beach house with two other couples and a single guy. There was a room with two double beds and there was another room with a single bed and pull-out couch.

  Rob wanted to do it while we were at the beach house, and I thought, "After all these weeks, he finally wants to get down and busy and I'm on my period." He told me, "You really should do it now because it will hurt less." He was saying if you’ve never done it before, it will hurt the least if you do it when you have your period because, "Your period, it’s like lubrication." He gave me this whole story. I was like, "Yeah but it’s gonna be messy."

  He sounded real convincing and he said the hotel staff would clean it up. I was duped from the beginning. I thought it was the right thing to do, the right time to do it. Maybe not right then when I was on my period, but Rob convinced me otherwise.

  We were sharing this room with other people so we were trying to do it quick and not get caught. We were doing it and the bed broke and fell to the floor. The sheets were a wreck.

  Everyone else eventually walked in and the bed is half on the floor, the sheets are off and wadded up in a ball in the corner. My girlfriend was like, "Ohmigod, you finally had sex?" And I’m like, "Yeah." And I told her about the whole period thing and she’s like, "What are you dumb?" And I was like, "Yeah." She’s like, "You never have sex on your period." I was like, "Rob said it wouldn’t hurt as bad and it would be more slippery. He said it would feel better." That’s what the dude said. He also said that the senses would be heightened.

  Boys will tell you anything to get you in bed. At least it was safe sex.

  A SAD STORY ABOUT SOMETHING THAT MEANT NOTHING

  Mary, 22

  I was in a juvenile program for kids on drugs and stuff. I wasn’t on drugs. For whatever reason my mom was fine with her other kids, she just didn’t want me. She worked for the state of Oregon and, through connections, managed to get me in.

  I came home for Mother’s Day weekend and my mom went off on me on how she didn’t want me there and how she wished I would have really made her Mother’s Day special by not coming home at all. She said she wished she’d never had me, just went off. I didn’t have anywhere to go. It was a small town, I was depressed and I had to get away. My older sister’s friend Tim lived nearby. I just needed somewhere to go, someone to talk to. I was 15 and he was 19.

  I walked over to his house and he acted comforting, he talked to me and calmed me down. We were sitting on his bed and I was crying and everything. He just totally pulled my strings and took advantage of the situation. It happened very quickly. I’m pretty sure I heard him say he was a virgin too but I can’t be sure if he really was or if that was just part of his story to get his pants off.

  Afterwards he walked me outside and told me, "You know we’re not together, right? This meant nothing." I said, "Yeah, I know," and I walked home by myself. It wasn’t exactly rape. I didn’t want to do it but, then again, I never said yes. And I wasn’t expecting us to be together or fall in love just because we had sex. I wasn’t one of those girls but for him to say that so bluntly just sucked.

  My sister was my best friend and she saw I was balling. I had gone over to Tim’s to escape but all it did was make the depression even worse so I told her what happened. She said she wouldn’t tell anybody but she was pissed because she liked him. After I went back to the juvenile home she told everybody.

  My mom found out about a year later. I was back home, again on Mother’s Day and again she was bitching me out for something and offhandedly stated, "At least all my kids are still virgins." I shouted, "Fuck you. I’m not a virgin." I told her what happened and how it happened on the last Mother’s Day and how it was her fault, "There’s your fucking Mother’s Day gift, you stupid bitch." She called me a whore. I shouldn’t have gone there but she set me off with those things she said about her darling kids being virgins. We don’t go at it like that anymore but we’re still not close.

  I wished I would have done it some other way. I wanted to stay a virgin until I was married and get married in a Mormon temple. It killed me that I would miss out on that. I started drinking and since I already did it once, I lost my self- respect and became a hoochie mama there for awhile. It ruined me for a good year or two but I’ve matured since then and realized that some people just suck.

  The way I lost my virginity affected my sex life for years and years after that. I strongly believe that, especially for women, sex is definitely more mental and emotional. If you have a bad experience, you really can’t enjoy sex. It took a whole five years after my first time until I was able to have any pleasure from sex whatsoever.

  I was dating this guy, we were sexually active for 10 months and I only got off once that whole 10 months. They say good sex makes up only 20% of a relationship but bad sex takes up 70% of it and that’s one of the main reasons I broke up with the guy. It’s like my first time ruined me and I was emotionally scarred from it. I just stopped having sex altogether until finally I fell in love and then boom – sex was awesome.

  If I ever have a daughter, she’s going to be the first to know that it needs to be something special or he should at least be important to you or it can scar you. You live and learn and every experience gives you more strength. And you never know, if I hadn’t gone through that experience I might not be where I am now, so I wouldn’t necessarily change it if I could… but I might.

  UNCLE KNOWS BEST

  Corey, 34

  I was cruising down the back roads of Michigan on my Honda Spree. I’m minding my own business then I see this girl in a Bon Jovi, stone-washed jean jacket with the fringe, walking along the side of the road. I was 15, this probably would have been in 1988.

  I whip up next to her like I’m on a Harley or something instead of my little scooter, and I say, "Hey. What’s going on?" She’s like, "Going to the store to get some smokes." So I’m like, "Sweet. Want a ride?" like hop on my fucking tiny Honda Spree. It was the first time I rode with someone else on that scooter and it could barely take off. It was bogged down so I had to run along side it to get it moving.

  Finally I get the thing going fast enough so we won’t tip over. We’re going down maybe a mile and she starts feeling my stomach. Then she reaches around and grabs my package, I’m like, "Whoa." "Pull over," she says. In Michigan there’s a lot of like two-tracks where you can just peel off into the woods. We find someplace secluded and start kissing.

  We lay down in the dirty, sticky pine needles
. I get on top of her and she takes just one of her legs out of her Palmettos, not even Guess jeans, but like the cheap Palmettos. At this point in my life I had not even jacked off. This was it, this was the very first. We’re doing it and it was the weirdest thing, my leg cramped up and my body seized and all this stuff came out of my penis and got all over the place. It felt really good but I was alarmed by it.

  We got dressed and I drove her to the gas station and I didn’t even get her name. She got cigarettes and I filled my tank and I peeled off. I was still freaking out about the orgasm. AIDS was still mysterious and scary to me and I didn’t know if stuff coming out meant something was wrong. I didn’t know. So I went home and I couldn’t tell my dad so I called the only person I knew I could talk to about this: my mom’s brother, Uncle Lenny.

  Uncle Lenny is totally super cool. I’m 34 and he’s 75 now and he still gets all the chicks. Really laid back and he’s kind of connected to the Detroit underground. I knew he was the guy who could give me some insight into what went down. I told him the situation and said, "I don’t know what happened. This like pus stuff came out of my penis." He was like, "You never jacked off before?" I said, "No." He was like, "Get into the tub. Draw a hot bath. Burp the worm for a few minutes and tell me if that stuff comes out again."

  I followed his instructions, got in the tub, jacked off; it felt good and I was like, "Oh, awesome." For some reason it all made sense to me.