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

by Wickens, Shawn

  She ended up telling her dad about it and she told me her dad cried about it. I don’t know if it was a guilt trip thing but she tried to lay it all on me about how upset he was and how he cried.

  RECONCILIATION: FACE TO FACE

  Marie, 25

  My senior year of high school, I was 18 so I was legal per se. I was a volunteer with the EMS in my hometown in New Jersey, answering 911 calls, that sort of thing.

  There was a party for the "New Squad", all the high school kids who volunteered with the ambulance corps. I got drunk, got completely annihilated and was there after everybody left ‘cause I couldn’t drive home.

  It’s just me and the host, this guy I worked with who was in his 30s. He starts giving me more drinks, and more drinks. He does the cheesy backrub thing. Next thing I know we’re in his bed having sex. I was watching the clock the whole time. For a whole hour I was watching the clock. Finally at four in the morning I said, "I have school tomorrow and I have to get home before my parents notice I’m gone."

  I get home and take a shower and I broke down. I couldn’t believe I did such the cliché, have-sex-when-I’m-drunk, idiotic first time. It’s so After School Special, but everyone does that. I told my best friend who said I should have a three- day grace period. "For three days you can vent and bitch and cry and moan. But after those three days if you’re still upset, you gotta go see a professional." I’m like, "Fine." Three days later I was still so upset. I’m Catholic so I went to confession.

  I was very big into the church. I had been an altar server, I was a Eucharistic minister, I was there every Sunday. I went to the rectory, pounded on the door totally bawling and found this priest I had known all my life and was like, "I need to talk to you."

  We sat down in his office, I’m on the couch and he’s sitting in a recliner. Totally nonchalant, I’m wearing jeans, a t-shirt, and flip-flops. I tell him what happened and he was like, "Were you safe about it?" I said, "Yeah, we used a condom." He said, "OK. That’s good." Which I thought was weird because the Catholic Church totally does not advocate condoms. Then the priest asked if the guy called the next day. "Um… well, no." "Oh, what a douche bag." I was like, "What? What did you say?" He said, "The guy should call the next day. I’m really sorry, Marie." Then he told me it was good I admitted it, that it wasn’t the end of the world, and that it’ll make me stronger. He sent me on my way without a penance. The whole thing was odd but sort of euphoric. I felt cleansed.

  The guy did end up calling me a day later. I lied and told him everything was OK. We had been friends, but it was never the same between us. We never really talked again and sometime later he moved out West and got married.

  I got over it and was like, "All right, whatever. Guys suck." Soon after that I decided I was gay and that ended that. Later I found out from most of my girlfriends that their first times were horrifying too, and pretty much everyone cried afterwards.

  One of the other volunteers ended up asking me what happened after everyone left the party. She was like, "We knew something was going to happen. That’s why we all left." Gee, thanks.

  THE HOLY GRAIL

  Dorothy, 39

  I waited until I was 29. I waited because of religious beliefs and I was clinging to that. I was really struggling with whether I believed it or not and this was the last thing that I was clinging to as proof that I still believed.

  After I started falling away from my religious beliefs, it was getting kind of embarrassing and I was at the point were I couldn’t admit it to people I was dating because it was just weird. The person who was the one, I told him I was a virgin and he said it didn’t matter. It didn’t matter whether I did or didn’t. That sort of gave me permission to be fine with it.

  We had been dating for three months when it actually happened and it was kind of an accident. He asked me if I wanted to, and I said, "Yes," meaning in the future or at a later date. And he’s like, "Ok, let me go get a condom." I was just like, "OK. All right. It’s gonna be now," and I decided to go along with it.

  It was a fairly different situation with most people because it was so weighted for me. It had become such a big thing in my mind because I felt so much older than average. But maybe I wasn’t hurt in the way that other people have been who jump into something that’s purely physical. In retrospect I might have done it differently. But I think that people take the step whenever they’re ready. You can’t really second guess yourself as to where you are… because that’s where you are.

  BASIC TRAINING

  Jonas, 28

  I’d held off for a lot of years, had a couple of chances but because of my Mormon upbringing I always backed off at the point of penetration. It didn’t occur until I got into the military. I was studying Russian at the Defense Language Institute and after being there for six months, a hot chick finally transferred into our unit.

  Everybody else got really sort of aggressive on her and for whatever reason I just held off and played hard to get. Because of that and maybe she could smell my virginity and innocence, she singled me out. I thought I was in control, but I later realized she was playing me the entire time. She was very experienced. After our second date, that was it. We were in the midst of the usual makeout session I was conditioned to, traditionally involved in, where everything stopped before it went too far. But she was a little more active and engaged and because she was a pro she drew me out of the reasons I had resisted women before.

  It didn’t last long, we’re talking 17 seconds. At first I felt shock that I actually went through with it. I got up, pulled away and was like, "Oh, God. You don’t understand. I’m Mormon." I told her that I had been holding off until marriage because otherwise it’s an unforgivable sin.

  Not more than a minute after it happened I left her on the bunk bed and I went in the bathroom to sit on the toilet with my head in my hands. She was actually quite sweet about it. She pulled me back into bed and basically ended up nurturing me. She laid me down and stroked my head and spent the next half hour telling me it was perfectly natural, completely normal, completely acceptable, and that everything was all right. I didn’t believe it then, but the next morning when I woke up I started to recall her comfort and the way she sort of placated me, and I ended up coming through it pretty guilt-free.

  A certain part of me, for many years after that, resented her because I allowed myself to go against my faith and my religion and my ethics. But she definitely opened my eyes and both delicately and gently introduced me to a new world and did it with such finesse that the next time I was with a woman, I was in love and prepared for that intimate moment. The guilt didn’t hold me back from the next relationship and it was really rewarding because of that first woman. I never even realized it until speaking about it now, but goddamn for years I hated that girl, and goddamn I’m really thankful for her.

  ***

  We drove up to the gate and it was closed. We were locked in on the grounds of the seminary and we both thought that it was a sign from God telling us we did something wrong and we could never leave.

  Amber, 38

  Warwick Neck, RI

  ***

  MISSIONARY

  Peter, 23

  When I was still in college I went on a summer missionary trip to Kenya. I was working with two priests and a handful of other students from my school, which I'm not going to name, in a little village outside of Nairobi. Every day we would bring in kids from the secondary school. I helped with the choir because I was involved with the theater in high school and college. This one choir girl, I’ll call her Mary, had a great voice. She was 16. I was 19 at the time and we started hanging out outside of the church. I met her family and stuff like that. We would just hang out, go for long walks; we just had a good time together.

  One night we were in her room just practicing choir, nothing out of the ordinary but that's when it happened. We hadn't even kissed before then, but she kissed me and we started making out and then it went further and further. She hadn't had sex be
fore either.

  I did have a condom on me because I had been brought up in a public school environment with condoms ingrained in my head. So I had them with me not because I intended on having sex but because you never know. When I knew I was going to her house that night I brought one with me.

  There were three other students with me on this trip, two girls and one gay guy. I didn't really feel comfortable with any of them keeping my confidence so I didn’t tell anyone and I especially had to keep it secret from the priests. They would not have approved of the relationship, let alone me having condoms on the trip.

  Mary told her brother and he was surprisingly OK with it. So as far as I knew he was the only other person who found out about it until I got back to the States. And I still haven't told many people. I told my best friends, I told my brothers and sister. It's not like the best story to tell. But that’s what we did.

  We had sex a few more times and continued to, I guess, like date. But in that environment it wasn't really dating. We couldn’t go out on dates; it was more her coming for choir practice and then me walking her home. She came into my room a couple times which we were definitely not allowed to do. There was a strict "no guest" rule in our rooms, guys or girls. So those were the risky times but when I was over her house her parents trusted me 100%. The door was closed and it was no problem.

  I think her brother was expecting a longer-term relationship. Her brother was expecting for me to take care of her and I kind of avoided that, made it as little of an issue as I could. But Mary knew I was going home so I think her expectations were low for that sort of thing. Obviously her parents didn't know about it otherwise I'm sure that would've been a huge thing. I mean, they were a family from the Catholic parish in their village so it would have been bad.

  But Mary was a great girl. I've never talked to her or written her since even though we exchanged addresses. She hasn't contacted me either. It was nice for what it was. She was happy with it. I was happy with it. At no point did I feel like I was violating her.

  CATCH-22

  Don, 41

  I was 21, kind of older for losing your virginity. I was in college at Texas A&M, big football school. This girl picked me up at a bar and unbeknownst to me she was dating a football player.

  Went back to her place and we were enjoying ourselves. That night was the best of both worlds, it was the greatest and the worst experience of my life. We ended up in her room having sex and everything and I was all nervous and all of a sudden a bunch of people come over to her place so there’s this huge party going on downstairs. Everybody’s drinking and doing shots, and then her football player boyfriend shows up.

  He was coming to her door which snapped me back to reality after such a blissful moment. I was grabbing for my clothes, wanting to hightail it out of there because the guy was bigger than I was. And in my immaturity, I wanted to prove to my friends that I’d gotten laid so in one fell swoop I grabbed her panties, left my clothes, jumped out her window and ran naked all the way back to my dorm room.

  I didn’t get caught. It was a clean getaway, I just had a bruised ego. We finished, I thought I was a stud and then seconds later I was just another guy running for his life, naked. I don’t think the boyfriend ever found out about it. I’m not sure because that was the one and only time I ever saw or talked to that girl. So it wasn't like a loving or emotional thing it was more just like an animalistic act.

  I proudly displayed the panties for my friends when I got back, but then I immediately called my younger sister to tell her I lost my virginity and that I was going to hell. I just needed to talk to somebody who understood that I kind of felt fucked up. After the initial thrill of it, I became so guilt ridden. I was raised Catholic, that’s why I waited so long. On the one hand I didn’t really care about it, but on the other hand I was like, "Oh my God, I’ve committed a mortal sin. That’s been 20 years ago now and I’m doing all right.

  BAPTISED IN THE RIVER

  Fran, 28

  I was in the Ogeechee River, in Georgia. My family had a river house so we would go there in the summertime and spend the night and have parties and stuff like that, although we weren’t supposed to be there, boys and girls together… we all were.

  My boyfriend and I, we were playing around, and I was on his hips in the water. He got aroused and we were already in the vicinity. It was kind of like, "I’ll just put it in a little bit." And then a little bit more became a little bit more. And a little bit more. It happened right in the river when I was 14. He was 15. We were each other’s firsts. I got little upset because I thought I was going to burn in hell. And then I kind of thought, "Well, we already kinda did it, we might as well have sex again." And I only felt guilty for about a week so we did it again, full on, on the top bunk of the river house.

  And just a little twist on the story, he also had an artificial leg. He lost it to bone cancer. That made for interesting sex.

  THE VOW OF CHASTITY

  Oscar, 34

  I had notions of becoming a priest or joining one of the Catholic orders so I held off and I stayed a virgin up until I was 25. I was in a discernment program and I was doing weekly stints at a seminary in Baltimore. I had met and spoken with archbishops about taking my vows so I was very close to going through with it. And the average age of men entering the seminary is like 28, 28 to 32. It's a lot older these days so 25 was around the prime age.

  Ultimately I decided that the priesthood was not for me and that I had no intentions of getting married so I decided I should enjoy my youth while I still had some. Luckily I hooked up with this girl who was an old grade school buddy; we used to ride the bus together. Lani knew all my history, knew my past, knew there were no skeletons in the closet. We weren't in love so that was good. She was a nurse so she explained everything to me in detail, what was going to happen, all the potential risks.

  She was doing a nursing stint in Memphis and I was at her apartment visiting for a weekend. I sat her down and I was like, "Lani, would you be willing to share my virginity with me?" She said yes and that she would be honored.

  Before the deed, I was getting ready for bed and brushing my teeth, looking in the mirror and thinking, "Oh my god, this is ridiculous. I'm 25 and I'm having this goddamn moment." But it went really smooth and great and this is gonna sound silly, but at the end of it she started to cry. I was like, "Why are you crying?" And she said, "I thought you said you were a virgin." I'm like, "I am a virgin!" She was like, "Then how did you learn to have sex so good?" I was like, "I'm a natural? I don't know."

  But she was crying because she thought I lied about being a virgin to get her into bed. We talked again and I reassured her that she was my first. It set a good tone of honesty and me being down-to-earth about sex with later partners. I feel happy that I've kind of continued that throughout my sexual history. Maybe waiting a long time for reasons other than you can't get laid makes you be able to appreciate it a little bit more when the time finally comes.

  It was funny because like I said we weren't in love but after having sex I thought I was in love with her. And she said, "Nah... that's just the sex." So I went back home and after a little while I slept with another girl and I called up Lani and I told her, "Yeah, you were right it was... it was the sex."

  ***

  As we’re getting into things the alarm clock radio in the hotel room goes off and it’s really, really loud music, "Jesus loves you, yes he does." It’s about one or two in the morning, we’re doing it, and this Christian Gospel radio station is blaring Jesus music at us. It was traumatic. It’s playing on the other side of the room and you don’t want to stop right away, but then you didn’t want to hear that reminder that you’re sinning either.

  Margot, 24

  Cleveland, OH

  ***

  CULTURE SHOCK

  Rushdy, 29

  I was in high school… this was in Egypt. And we should be studying for our last year in school as it was a very hard year. Suad was maybe five or six ye
ars older than us. She used to be married and then she came back home to stay with her family. We found out later that she was divorced. It’s not as bad as it used to be but it’s still unusual to be divorced.

  We knew her from a long time earlier. Three years earlier we used to know guys who would sleep with her but not break her virginity at all. I don't know if some people understand how you can sleep with a woman and not touch her... just like just outside the bodies, without the whole connection – clothes on.. She had to be scared to lose her virginity because when she got married if the husband find out that she had lost her virginity it's a big problem. She would be divorced the next day and then she would get killed from her family the day after that. So it's kind of complicated.

  Actually she pushed us to do it because she used to be married and she used to have sex, but then she was divorced and could have it no more. It was safer to be partners with her because she had already had sex so it wasn't like people would look at her differently. Suad had been divorced I believe because she could not have kids. I believe that's what the secret is but I'm not sure.

  This was in an eight-floor apartment building and she lived on the seventh floor and my friend lived on the sixth floor so we know her as like a neighbor. She used to babysit for him.

  So I was excited about it. She came this day downstairs and always what I hear from stories is that everyone wants to go first. I said I'm going first. This woman and I actually went in my friend’s parents’ bedroom, and I started kissing her. My friend was waiting outside with all respect. No interrupting or anything. Then I wasn't planning to do it, but she was very horny I guess. And she just grabbed my penis and I was scared and the first feeling, actually it was incredible. Like very warm and very, "Oh my god," and, "Oh!" I have to be honest, I was still scared but I was probably the second person to do that for her after her husband. So I wasn't scared about any disease or anything like that. Then I’ll be honest, I didn't want to finish but I couldn’t help it! Then my friend started up with her.