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

by Wickens, Shawn

  I guess I was in the mood to do something drastic because it happened Christmas Eve and after Christmas Eve dinner ended I went over to my best friend’s house who lived two doors away. Trey and my friend and this other guy were over there and there was no denying that sex was in the air. Of course we ending up smoking pot and drinking some beer but then someone put on Rod Stewart’s song "Tonight’s the Night," so the mood was engineered by these two guys.

  We went into this other room and he and I had made out before, but I had never gone all the way. I didn’t really know what "all the way" was. So while we had kissed before, we had never really gotten that physical. That night I felt moved in that direction; compelled to do it since the clothes had come off and my friend was doing it in the next room.

  It was a very unsatisfying experience. I was so shocked. I thought for sure that this man, who was 20, would know what to do. I think he was drunk and nervous, in that order, but he couldn’t keep hard like Kyle MacLachlan in Sex and the City – he could raise his sails but he couldn’t get it into the harbor.

  I was menstruating and as a 14-year-old you’re kind of new to menstruating and as far as sex goes, I didn’t really know that I could move around. I never heard from him again. I asked my best girlfriend, "Why is he gone, what happened?" She said that Trey had told her that he didn’t want to fuck a log. Of course he was fucking a log, I was 14, I was menstruating, I was lying to my parents so I could have sex with my older boyfriend in a basement. I was just so freaked out about everything I really didn’t know what to do.

  I was so thoroughly disappointed and shocked by his unpleasant and callous treatment and it did two things to me. It made me want to become the best lover ever and I’ve made quite a bit of progress on that score. And it also made me lose about a hundred points of respect for all men. There was such a lack of compassion and sensitivity and instruction even, on his part. I mean you gotta know that if you’re doing a virgin you’re going to need to tell her a thing or two.

  I saw him a few years later when I was 17. I was just about to graduate from high school and I had gotten an early decision at a few universities, had done very well. I had my driver’s license and really had my act together. He walked over with a big smile and tried to start some small-talk conversation. I looked at him dead in the eye and was very curt and didn’t let him off the hook because if you deflower a virgin you really have a bit of an obligation to ease her into that new life, because her life is never going to be the same again. He didn’t do that and I look at it as a betrayal to the art of sex, which really can be quite beautiful and expressive and to do that to me, a sweet, nice looking, smart girl from a good family… it was just really pathetic on his part. I only credit the years and years of counseling that I’ve been able to endure that allows me to not hold it against every man I’ve ever been with.

  IT’S A SIN TO KILL A MOCKINGBIRD

  Alexandra C, 31

  ALEXANDRA C: It happened on a snow day. A snow day when I was in the eighth grade. I was 13.

  SHAWN WICKENS: Where are you from?

  AC: Originally I'm from Michigan. And I had moved down here to Nashville and it was with a boy from my math class. And um...

  SW: How did the day begin?

  AC: I found out it was a snow day because I'm an insomniac and I was up all night watching it snow. And when I realized I didn't have to go to school the next day the first thing on my mind was, "Well, I get to be alone with this boy," because he lived down the street. And he skated over.

  SW: You called him?

  AC: Of course. And I guess we both kind of knew what everything was going to lead up to and it did. And it wasn't fantastic, and it wasn't mind-blowing and it wasn't what I had expected it to be at all. It was just this thing that happened and it felt strangely adult.

  SW: Did you guys discuss, did you have an adult conversation?

  AC: We had a conversation in the only way that we knew how, I think, which was... I think I was kind of crying afterward and I said that I felt funny about it. I felt bad in my stomach after I had it.

  My best friend was older and she had had sex with someone and I think she lied and said it was great and wonderful and then when I went ahead and did it, I realized the gravity of what had happened. Being the only girl in my class who had that kind of knowledge when kids were still making out and feeling over the shirt… I had had intercourse and that was extraordinarily disturbing to me on many levels.

  SW: Did anybody find out?

  AC: That's... silly you should say that because my group of friends had perceived me to be the girl that you went to to find out about things because I was experienced and that wasn't necessarily the case. I mean the whole thing turned me into a serial monogamist. I didn't want to necessarily do this thing all the time with everyone I met. And I was terrified of it. And that's what people never understood.

  SW: Did he make subsequent advances that you had to deny?

  AC: The crux of our relationship became purely sexual, as much as sexuality between two extraordinarily young people can be. But yeah, sure and... we both did and we both, it was any time, any place, in a field, at school. Whatever. It just became the reason for being.

  SW: That’s probably all you understood relationships to be.

  AC: I stayed up the entire night before reading To Kill a Mockingbird. All in one sitting. And... I think that's had more of a profound effect on me than the sex. Would I have waited if I could do it over? Probably. I think it's served only to turn me bitter and to expect much more out of people than they are able or willing to give.

  SW: Had he read the book as well?

  AC: No, he was not smart. He was cute, but he wasn't smart.

  SW: No literary conversations then?

  AC: No. No, God... Jesus. no. For most of the time when I was in junior high and later in high school I only had sex with people I could dominate. It's true. Because that's what I perceived the act to be about. There wasn't love involved, there was me telling boys or making boys do what I wanted them to do. And then in the end, they got off. I didn't, but it certainly made me happy to manipulate people.

  I didn't get off my first time but he did and that's… I guess, in the end, that's what was important to me – that the guy got off. And I felt better for making that happen for someone. Sick, co-dependent, passive-aggressive. Whatever you want to call it, that's how it was.

  SW: Well if you couldn't get off you were the cause of... you made somebody else feel good.

  AC: Exactly. I was the catalyst for someone else's good feeling. And that was enough. It wasn't until I was married until I thought that I had something close to meaningful sex.

  ***

  I went downstairs and the girl who was dating my brother asked me, "Did you just have sex with Billy?" I was like, "Yeah." And she said, "Ohmigod. You look exactly like you did before you two went upstairs." My hair was the same, there was no makeup taken off my face – nothing was different. And my brother was so mad because I had sex on his bed and with his best friend.

  Marisa, 22

  Pottsville, PA

  ***

  RACE RELATIONS

  Will, 27

  My assistant manager at the United Artists theater I worked at was all into me and I didn't want him at all, we were just friends. Brandon was black and, not that there is anything wrong with that, but it ultimately becomes important to the story.

  Anyways, I was driving him home one night after work and he was talking real dirty. He was well hung and I could totally see it in his pants. I had lied to him before, because I didn't want to sound like a virgin and had said that I had sex before when I was in high school, even though I had not. I really lost it that night when I was 20 years old.

  So he was under the impression I had sex before and he was telling me, "I've never had sex. I wanna have a first time. You're my friend, let me have sex with you." I was like, "I don't wanna have sex with you. I hate you."

  I'm driving around and we'r
e near my house, which is off this road with all these brand-new housing developments. There were all these paved roads with nothing on them so finally after all his constant nagging I was like, "Fine. Is that all you fucking want?" I was pissed and annoyed so I turned off the road and we stopped at a dark, little cul-de-sac. I turn off the car and I was like, "Fine. Take out your fucking dick." He takes it out and it's huge, I'm like, "Good fucking Lord." It’s so huge, I didn’t know what to do with it.

  We start with making out but when Brandon makes out he wraps his lips completely around your mouth and he's like inhaling your face. So by the time I’m done making out with him my whole face was like dripping with saliva. Already I was mortified. Then I realize I have to go down on him. I’ve already gone this far and it’s what he’s expecting. I go down there and it’s so big I swear to God after a minute and a half my jaw was aching. I was hurting and I couldn't go too far down ‘cause I started choking. He's not finishing and I'm doing it forever. It’s not phasing him at all and I need to breathe so we stop.

  I decided let's just go in the backseat and give each other a rest. We go back there and you know he wants me to do it some more to him, so I'm like, "Oh, fucking hell." I start doing it some more and finally I'm just like, "You know why don't you go ahead and just try to do it to me." And I had never had a blow job so I had no idea what to expect. This was my first time for everything and I have to pretend I’m a seasoned veteran.

  He puts his mouth on my penis and I swear to God five seconds later I'm coming. So he's like, "Do you always come this fast?" I'm like. "No, um... I was just really excited." I'm all embarrassed and it's like, "Oh shit. Now I've gotta make him come." So I'm working, working, working. Finally after forever he's like, "I don't know why I can't come." So he wants to like rub it on me. I'm like, "All right do whatever you gotta do." I'm laying there, and he's rubbing his penis all over my stomach.

  We were doing it forever and I got hard again so I actually came again. He's still rubbing and finally he comes and I'm like, "Thank God." I used his shirt to clean everything up. I took him home and I just remember I was so horrified. I told him, "Don't tell anybody we did this," because we had all the same work friends. I was so embarrassed.

  I got home and, here's where the black part comes in. You know some black people have to keep their body lotioned up because their skin gets ashy. He always used this like cocoa butter crap on his body. So I get home, I get into bed and I'm reeking like cocoa butter and I'm feeling sticky all over because he was sweating and it dripped off on me. At this time I still lived with my parents. I didn't want to like take a shower at two in the morning and wake everybody up so I had to sleep all night smelling like cocoa butter. Oh, it was fucking horrible.

  I had to wash my sheets. I lied and told my mother that I took a shower and put my wet towel on my bed and so my sheets got all wet. I ended up moving out of my parents’ house a week later.

  Then what happened afterwards is that Brandon was such a big mouth and he told my friend Mary Jane and I had to basically lie and tell him in front of Mary Jane, "Don't fucking lie," because it was horrible for me. I just didn’t want anyone to know. He got really mad and offended by that, obviously, so we stopped talking.

  THE ULTIMATUM

  Steve, 28

  New Year’s Eve and my girl’s parents were out of town. I’m not sure if there was a no-boys rule or anything but she threw a party with me, her, her friend, and my friend. I wasn’t really into drinking then but I started boozing and smoking pot and that made her angry. But it was New Year’s. What else do you do but get smashed? I grabbed a bottle of something out of her dad’s liquor stash, lifted the bottle and took a drink and she was like, "No… don’t. I’ll give it up," and she handed me a condom. I was 15, she was 13 and her way to get me to not smoke or drink was to have sex with me.

  My friend was already off in another room doing it with my girlfriend’s friend. I gave my girlfriend head for 30 minutes but I’m not sure if she came or not. After I gave her head we had sex for about, maybe 15 minutes.

  We did it, the act is done. I come out of the room and my buddy is finishing up and his girl is sitting there digging inside herself because the condom fell off inside of her and she already had a tampon inside her too. After they worked that out, my buddy and I left. It didn’t keep me off drugs, I started doing stuff right after that.

  She was a sweet girl. I don’t regret it but we were really young, I guess. It’s led me down a weird path because now I’m pretty much open to sleeping with a lot of different people.

  I ran into her about a year ago and she didn’t recognize me. That really hurt my feelings because this was the girl I lost my virginity to. I waved at her and she didn’t even know who I was. It made me feel kind of bad because it was like a role reversal of things. Like guys are supposed to be the hard-asses.

  THIS OTHER TIME, AT JOB CORPS...

  Ruby, 24

  I was 19 when I lost my virginity and I really wished I hadn't done it because I lost my virginity to a boy, who will remain nameless and I only did it because at the time I thought I didn't really need my virginity anymore. I was in Job Corps in Kentucky. It was a closed campus so you couldn't go anywhere off the campus grounds.

  I lost it my second or third week there on Valentine's Day, right after the Valentine's Day dance. I had just broken up with a boyfriend specifically so I could go out with this other boy. Relationships at Job Corps are really, really messed up because you're with a person not quite 24 hours straight but you’re with them a lot. The only time you're not interacting with them is during classes, unless you have classes together, and when you’re sleeping. Pretty much the rest of the time you're with them constantly, so relationships can degenerate really, really quickly. I guess I was just horny and I was in the mood and I ended up losing it outside, behind a cafeteria. I was really embarrassed afterwards and I dumped that dude a couple days later.

  But yeah, I lost my virginity in Job Corps like I’m sure several people have. And it was on Valentine’s Day, you can't get any cheesier than that. He was a good ol' boy, country as all heck. Me being a country girl, he reminded me a lot about home. Job Corps was the first time I'd ever really been away from home so I’m sure there was a little bit of homesickness wrapped up in there.

  Previous to this I lived a sheltered life when it came to guys. I knew what sex was and I knew it would happen some day. It wasn’t the ideal time but I didn’t force myself into the situation. It was just that I decided why not and I grabbed the first warm body that came my way.

  He had great eyes and an endearing way that he held himself, this goofy, fun kind of a personality. His demeanor was more what I was focusing on that prevented me from seeing his teeth. Now when I look at a picture of him he's got such terrible teeth that stand out, the absolute worst teeth I've seen on a human being. And you can’t see his personality in a picture, all you can see is his teeth. Nowadays I'm looking for better teeth.

  My advice: If you haven't lost your virginity yet, and I'm not saying this for religious reasons or for social reasons, but if you haven't lost your virginity yet... wait. Wait, and I’m not saying wait until you're married but wait until you know it's going to be something special that you can remember. My memory is behind a cafeteria with my dress hitched up and my underwear around my ankles. You can't get any lamer than that when you’re five feet away from a dumpster. Wait until there's a bed and candles and incense and it doesn't have to be true love, but there should be something between you and him that you'll remember forever.

  If I could redo it, I would've waited and done it with this other guy who later on in the program became my best friend. George and I met the very first day I got to Job Corps. It was his first day also. He became a very, very good and trusted friend of mine and we left at the same time and we kept in touch and we remained friends all the way up until he was killed. He died in a car accident when a drunk driver hit him. I wish that I had lost it with George instead
. I’m sure he knows. I still get little twinges and tickles from him that let me know he’s around.

  HAVE YOU SEEN MY BROKEN HEART?

  Melissa, 23

  I was 17. I had just graduated high school. He was 23. We met through friends that I worked with. I was pretty experienced. I had just never had sex, but I was ready. I didn’t love him or anything, I just thought it was time. So we fooled around for a couple of months and we finally did it on his living room floor. I still had my tennis shoes on.

  It wasn’t really a good experience because, as a girl, you build it up and you think your first time is supposed to be with someone you love. I wasn’t even in a relationship with him. It was just a physical thing. I was scared and a little ashamed. Afterwards I went home and drank a bottle of cheap vodka and passed out.

  The next morning I woke up and felt ashamed and felt like a different person. It was early and he called and I thought, "Oh, he cares. He’s checking on me." Then he said, "Have you seen my wallet?" I thought, "This is not how this conversation is supposed to go."

  I didn’t tell anybody I lost my virginity for a week. I was so ashamed I couldn’t even tell my best friend whom I normally went to for everything. The first person I went to was a male friend of mine and I was all upset because I didn’t love the guy I had sex with. My friend said, "You know Melissa," and this made me feel better, "one day you will have sex with someone you love, and then your first time will really be irrelevant."