How to Lose Your Virginity ...And How Not To (16 page)

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We had sex on my boyfriend’s friend’s living room floor. And this was after I had just thrown up on him, like ten minutes before we started fooling around. We finish and he falls asleep on the couch. I look down and it’s bright red on this guy’s white carpet. I sat there trying to clean this up and eventually I passed out. His friend comes downstairs the next morning and he’s like, "What the hell is this? What the hell is this red stain on my carpet?" We told him I was drinking vodka with Kool-Aid."
Yolanda, 28
Ann Arbor, Michigan

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I CAN’T BELIEVE I’M TELLING THIS
Bryce, 40
I was 16 or 17. My upstairs neighbors were two brothers who were about four years older than me. They were both gorgeous guys and I had a crush on both of them and they knew it. They were both bisexual so they were dating women and men. One day Craig, the older brother, took me down to the basement and I gave my first blowjob. He shot a load in my mouth so I’m guessing I did OK.
Then this other time, his brother Stan asked me if I’d ever been fucked before. I told him no and he asked, "Would you like to try it?" Not one of my best experiences. I nearly bled to death but I survived it after a lot of Preparation H and ice cubes up my butthole.
One of the them is married with two beautiful kids now, but we’re all still very close.

***

I used to have just fleeting thoughts about sex in my brain but after that moment I couldn’t stop thinking about having sex. Whether it's sleeping, waking moments of my life I always have girls on the brain. Before that first time I actually had plans and thoughts of doing things and stuff. Sex: worst mistake I ever made.
Peter, 33
Westlake, OH

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BEDSIDE MANNER
Shannon, 38
I was 13 when I got my period and my mom was of the school of thought that once you get your period, you need to get a checkup from the gynecologist to make sure everything is OK. So I went to the gynecologist over at Women and Infants Hospital. He goes to look at me and because I was tiny, in those days they used those awful silver clamps, he jams the clamps in there… BAM, that’s it. Blood everywhere. I cried. I screamed. He apologized but that didn’t change the fact I was totally robbed of my virginity.
I told my mom there was blood but my mom was a very strict, Irish mom. Like you wouldn’t ever mention sex to her, never mind, you know, "Hey, the doctor just took care of me, thank you very much." But that was it and I was frightened to ever go back there. But maybe it was a good thing because maybe the first guy I slept with wasn’t worth losing a cherry over.
RIPPED INTO ADULTHOOD
Xander A., 32
XANDER A: I'm from Texas in this small town called Alvin outside of Houston. I was like a New Wave kid in the ‘80s and my sister... my sister was two years younger than me so wanting to be like her big brother she was a New Waver, too.
So she had her little friends, I won't lie… I'm not proud of it, but I would listen to hear which one of her friends was going to spend the night because then after my sister would fall asleep they would sneak out and come to my room. Now my room wasn't in the house. We lived in a big wooden house and there was a storm shelter in the backyard. So I moved down there to start doing drugs and do everything they talk about in the book Fear and Loathing in Las Vegas... so my sister’s friends would sneak out and come downstairs well... her friend Lana came down.
SHAWN WICKENS: Your sister didn't find out about it?
XA: She knew that her friends would come down but she didn't say anything, you know. But it was just kind of known. So I would always keep an ear out, "Oh. Mary is staying the night? Oh, hell yeah." Friends would ask me, "You going out Friday?" "Hell no." So... Lana came over one night and we made out and... it wasn't like today where you can just turn on the TV and know how to do anything. I didn't have HBO. I wasn't an idiot but everything I had learned was from Frederick’s of Hollywood catalogs.
Anyways... I had an 8-track player… the shed in the backyard was like a clubhouse room. So I found an 8-track player and, no lie, we were talking and laughing and listening to The Muppet Movie soundtrack, which is a fantastic soundtrack. I had no idea that one day I would lose my virginity to this soundtrack. But, this turns into a kind of tragic, painful situation for me. I knew that it hurt girls, losing their virginity. So, you know we… Muppets are going on and it started out with, "Why are there so many songs about rainbows?" So that was the sexy song. Brother now I'm playing the, "Moving right along... foot loose and fancy free." That's when I started getting it on, bro.
So anyways we are making out and we attempt and... and I'm looking for it and I had practiced so well with my erections since I was 12. If you would have left a wallet out I would have had sex with it but I think I speak on behalf of all the boys at 12 with their Fredericks of Hollywood.
We're going and I remember it hurting really bad and I thought, "But I thought this was supposed to hurt only the girls." And she goes, "What are you talking about?" No I didn't say that out loud. But, so anyways it hurts, and we kind of finished and I'd never actually been inside someone. And so anyways so... I went to pee and I remember it hurting, passionately. This is a true story, I'm not making any of this up. So I'm peeing and it hurts so bad. I looked down and I had caused a small tear in the head of my penis, no lie.
SW: What?!
XA: No lie. And it gets worse... so now I'm torn, and it hurts. Any other time when I cut myself, not that I made a habit at 15 of doing this but when I cut myself I would go to mom. Not going to mom with this, you know because, "Serves you right. You were having sex... sin! Sin."
SW: Were you from a religious family?
XA: Oh, my mother is a Pentecostal minister, bro. But anyways... so I've torn the head of my penis and what do I think to do? This is not a fucking lie. I grabbed a bottle of alcohol… rubbing alcohol. No lie. I'm 15... I am a dumb kid. And this is a 1980s 15-year-old. Not a year 2000 15-year-old, which is the equivalent of a 27-year- old. So there is still some innocence in me. Anyways so, it's like four in the morning ‘cause my moves took forever.
SW: This was on a school night?
XA: Yeah, this is on a school night.
SW: Was she there assisting you at this point?
XA: Oh no, no, no, no, no... no she was, sorry… I had gone into the house. She was still outside.
SW: Did she know about any of the tragedy that...
XA: No, I just told her I went to pee and the reason I... ‘cause normally I would have just gone in the bushes, it's Texas. So I'm peeing, and I get the bottle of alcohol... and it's like four or five in the morning and I pour some on and I swear to God, bro, I saw into the future! It fucked me up and I let out a yell like, "Arghhhhhhhhh God! Oh noooooo-ahhh..." ‘cause I mean, dude, you know head of a penis is a sensitive part. Tear, alcohol. I didn't know, you know. I wasn't going to put a Band-Aid on it. Nothing stupid like that... no, I did something smart like put alcohol on it. Severe pain. And so to end my virginity story... I got the virginity out of the way and the next day dropped acid at school for the first time, so did the acid and the virginity all in one day. That's the end of my story. Oh, and I healed nicely.
SW: Were you compelled to try acid because you were in pain?
XA: I knew I was going to try acid the day before, I didn't know I was going to lose my virginity that night because I didn't know my sister was going to have Lana spend the night. Life gives you lemons, bro, you tear the head of your dick.
SW: How was it, on the side or right on top? Like it made the hole bigger?
XA: No, no, no, no. Right on top. Oh that would've been terrible... now you're talking crazy shit. Can you imagine? Oh God I don't want to imagine.

***

There was a laundry chute in the bathroom so I snuck into the bathroom and climbed down through the laundry chute. My girlfriend walked down through the kitchen, met me in the basement and let me out of the house. I scratched my back up pretty severely, but managed to keep the escape pretty quiet.
Luke, 25
Nashville, TN

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SCHOOL’S OUT FOR SUMMER
Dimitri, 28
First of all, I’m gay. I am now anyway. But when I was 13 I was visiting relatives out in Long Island; out in Hicksville, Long Island, of all places. I was up there one summer staying with my cousin Zack who was this really hot Italian boy my age and I so had a crush on him. I justified my crush because he’s not my first cousin, so I could probably do him, but he’s not gay. Zack had a crush on this girl named Tiffany Berkley.
Tiffany had an older sister Adriane. Tiffany was a year older than us and Adriane was 16. It was the first time I met her. We went over to Zack’s middle school and outside of all those old public school buildings there’s those stairs, those cement stairs that lead down to a pit and the doors for the boiler room. That’s where we went, down in that pit. Zack’s hooking up with Tiffany and I’m stuck with this Adriane girl, the sister, who I was totally NOT into. She was actually a cute, beautiful girl but I’m a homosexual. I knew it then, whatever, I know it now.
The only thing that made me horny was the fact that 12 feet away from me, Zack was fooling around with Tiffany. Hot. He’s still unmarried so there’s hope. Anyway, Adriane and I were hooking up and she’s reaching in and then she pulls down my pants and all this nonsense. So she’s ready to go, she’s ready to go and we’re stripping and I think, "Aw, shit." We all have sex. I’m in her and she’s like, "Ehhh, I can’t feel a thing." The whole thing was gross. The whole vagina thing was just nasty to me. That sealed the deal for my homosexuality because my first memory of sex was going down into this cold cement pit leading into a boiler room. I was against the steps with this girl on top of me, her hands on the metal railings. My back was all scraped and scratched up, and she was just going to town on me. It was horrendous.
Of course Zack thought it was the hottest thing ever that I scored and he scored too. I can remember the coldness of the metal and not wanting to do it. Ugh, I’m really happy that I’m homosexual.

***

It was in a car, a Mustang, the back seat. I got pregnant but it’s gone. It… ceased to exist. I was 15.
Karen, 23
Medina, OH

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UNREQUITED SEX
Stacy, 21
He was my first real, real boyfriend. Six months into the relationship I thought I loved the kid. We wound up doing it on my bed at 5 o’clock in the morning. My mom was right next door. It fucking sucked. In the meantime I was trying to make it better so I said, "I love you," and he never said it back. I was stupid and 16. There are times when a guy wants to reciprocate and pleasure the girl and this was definitely the kind of first experience where he was just trying to get off. I thought I loved him and he didn’t love me and that hurt real bad.
The next day I had a grotesque bathroom experience at an all-day concert and spent a lot of time doubled over in an outhouse – wasn’t used to the whole cherry-breaking.
DOWNHILL
Lacey, 22
I was 17 and used to ski competitively – slalom, GS, super-8, whatever, and I met this guy at a ski race. He was in a competitive class above me and we were on the top of some mountain when he turned his head my way so I thought, "All right, sweet. I got some college guy’s attention."
He invited me to a party back at his condo and I went with a couple of my younger girlfriends and we drank… a bunch. It was probably like my first or second time getting drunk. He took me up to the attic where everyone was laying in their respective make out piles. I was really fucked up and thought I was so cool because I had a college guy. Then it became like the situation at the beginning of Kids with Tully saying to that girl, "Yeah, you’re doing great. You’re doing great. Keep on going. We’re almost there." And I was saying, "No. It hurts. Stop." ‘Cause seriously, and not to be vulgar, but it was a huge penis. I’m 22 now and I’ve seen other penises since then and I still consider his to be huge.
So it sucked, it was a terrible experience and later on at the party someone told me the guy was still dating his 25-year-old girlfriend. It was awful. I was traumatized. I didn’t have sex for like two more years after that because I just hated it. And on top of all that, he told his friends that I was a prude and that I wouldn’t even have sex with him, which I did. I did have sex with him, it felt horrible, and he lied about it.
ALL I WANTED WAS FOR SOMEONE TO BE THERE WHEN I NEEDED
Deborah O, 21
DEBORAH O: I got kicked out; my parents are divorced and I got kicked out of my mom's house and I moved in with my dad. And then a month later he started going through a divorce from his second wife.
SHAWN WICKENS: Was this in the same town?
DO: Yes. It was in the same town, everything. Well, my brother was kicked out earlier so pretty much I was cut off from everyone in my family. My dad was going insane and I wasn't on speaking terms with my mom and my brother was nowhere to be found. And my dad wouldn't let me speak with my stepmom. So I didn't have anybody. Plus I switched high schools all at the same time and... I was 16. I started hanging out with… not a bad crowd, I was just used to being a straight-A student and so I got into drugs and alcohol and skipping school and all that stuff when I met this guy named Orlando Ortiz. He was Dominican. I was young, I was 16, I was just of age, you know, legally I would say. And I really, really liked him. I thought he was beautiful.
SW: Can you remember the day you two met?
DO: Yeah, I do remember. We were at a party and I knew that he really liked me, but just initially, from the looks, from the natural vibe, but I wasn't that interested. It was more when I got to know him and the little things like the slight accent, when he would drink you could hear it a little bit more and... I liked the fact that he treated me like I was too young to be sexual. Like in some way it gave me an advantage that everyone thought I was naïve. I hung out with him and our whole group of friends every single night ‘til about 4 o'clock in the morning.
SW: You were still at your dad's at this point?
DO: Yeah. But my dad, he stayed out really late. He was really messed up emotionally, too. So finally, the fact that I had this tremendous crush on him just came out but he had feelings for one of my older friends... but she didn't like him.
SW: He shared this with you?
DO: Yeah... I mean, it was obvious. And I was so young too, and naïve... so he called me one night when he was really drunk and asked me to come pick him up to give him a ride... ugh, this is such an awful story. I really, really liked him and I picked him up and gave him a ride and then we decided to go to the beach. We were on the sand, near the ocean and we started making out and then we went to the lifeguard post and had sex on the lifeguard post and then went back to the car.
SW: Him sort of sitting down and you on top of him, I guess...
DO: No, no, no. Well it ended up we were standing and then it was just too painful so I had lay down and then he was on top.
SW: Was it just a chair or was it a large...
DO: No, it was the lifeguard post like the big structures they have on the beach. It was pitch dark, a little bit windy and the sand was uncomfortable and all that kind of stuff but... so we walked back to the car and that's when I realized how drunk he actually was. And then when we got back in the car, I remember it was a CD we listened to… Ginuwine, do you know which one I'm talking about, anyways it’s the ridiculous album with the song "So Anxious" on it*. So we made out for that whole album.
I dropped him off at his house and we made out for like a good 40 minutes. I remember the whole day afterwards wondering if he was going to call and he never did and he didn't call for a whole week. And then I saw him at one of the gatherings.
SW: At a house party?
DO: No, it was actually outside, it was a big keg party or something like that. He saw me and said, "Oh, hi," and he gave me a kiss on the cheek and then he went on to go flirt with other girls. Highly painful. And then when I talked to him about it later I said, "What's going on?" He goes, "What? I'm always nice to you. I always give you a kiss on the cheek." And I said, "Well, Orlando, you always give everybody a kiss on the cheek." And all he could do was laugh 'cause he was embarrassed because it was almost like I called him out and he had guilt about it... but not enough pride or not enough integrity as a man to even talk about it. But at the same time I knew that he wasn't mature enough to take responsibility for the fact that he was not sober and I was sober and I willingly, you know, gave my virginity away.
His friend gave me a call and asked me if I was a virgin anymore and I said, "No why?" And he goes, I was just wondering. I said, "Why would you ask me that?’ And he goes, "I was just wondering." ‘Cause they all knew that I was a virgin and then... so...
SW: Maybe he didn't remember it happening?
DO: No, I think Orlando was bragging about it. And that upset me. I realized that he may have been older than me but he was less mature and I just felt... 1) hurt, taken advantage of and 2) really, really naïve all at the same time and it changed my view on men and on relationships from then on.
SW: And plus your parents were divorced and your dad was remarried and he was getting divorced. Were you more hopeful about relationships in general before then?
DO: No. My stepmom was cheating on my father for like the whole ten years they were together. I just felt like there was betrayal everywhere I went. It wasn't that I wanted to have sex with him, I just wanted some sort of relationship. You know, some sort of love and then when I realized that that's not what sex was… it… really messed me up. I got depressed to the point that it affected my body because I no longer wanted anyone to find me attractive. So, looking back on it now I subconsciously started gaining weight and I stopped shaving my legs just because I didn't want to go through the same experience.
SW: Did he see you during this self-imposed unattractive phase?
DO: I removed myself from the crowd. I went back to my old high school... my father and I started going to therapy... I didn't speak with my stepmom anymore but my mom and I got in a relationship again and, well… on top of all that stuff happening I thought I had cancer.
SW: How did you think you had cancer?
DO: This was awful. I was under so much stress from my mom's house. I was a really good kid, I didn't deserve to get kicked out. I think she was menopausal and I was the typical emotional teenager, you know, anyway I was feeling so emotionally abused that I was bleeding rectally from the stress.
SW: I would think cancer too then.
DO: Yeah, yeah, yeah. Well, I had to get a colonoscopy... my like GI guy, my specialist told me that I needed a colonoscopy ‘cause he thought that I had cancer or something like that. And it ended up it was just stress. But I had to do all the medical appointments and everything by myself. I had emotional support. I had all the financial support I could want but all of it means shit... you know?
SW: Well there was a silver lining. You got your dad into therapy.
DO: Yeah. I was always the advocate to wait until marriage and then it was just ironic that once my dad and my stepmom who I had considered a perfect marriage, split up, that's when I lost my virginity. Now I don't believe in the institution of marriage whatsoever. My dad got remarried and now he has a baby. His new wife is manic-bipolar. I just have no fucking faith and it's awful and I think it's a product of how I was raised.
* 100% Ginuwine
A LOT OF MONEY BACK THEN
Bob, 42
Many moons ago I was 16, my girlfriend was 15, and we both decided to break our virginities together.
Maybe I had the condom on for too long, it was on the whole time during foreplay. But when I pulled it out the rubber was broken. She didn’t have a period for a while, then we went and got a test. Knocked her up – had to pay for an abortion. That cost $135 at the time. Paid for it with money I made working as a cart boy at Target.
We were both too young. I regret it, though of course by now I could be a grandpa, were my child to have made the same mistake.
Other than that it was fun.
THE AFTERMATH
Ed, 45
Junior year some of my friends and I struck up a friendship with our English teacher. She was fairly new; I think it was her first teaching experience right after college. She was a pretty cool teacher. She was newly divorced from her childhood sweetheart who was a heck of a high school athlete in his own right, and she was living in a trailer out in Lincoln. Various weekends she would invite us out to her trailer and we would drink and party with her and her new boyfriend.
This one night… during our Christmas vacation, I distinctly remember it was the Sunday night before we were to go back to school. I get home from pumping gas out on I-80 and my dad said there was a phone call for me but they didn’t leave a message. The phone rang again and it was a couple of my friends saying they were at our teacher’s trailer and they wanted me to stop over.
By the time I got there she was pretty liquored up. My friends were liquored up too but not as bad as she was. One thing led to another and we were in the hallway shooting beers, spraying each other. A few of the guys got their shirts wet and took them off and she started making out with us, going from guy to guy. Pretty soon her and one of my buddies went into her bedroom. They were in there quite a while and so we pop the door open and we could see the old white ass bouncing up and down. After he was done he came flying out and another buddy went in there. Then I was third, same thing. Went in there and it was my first time and all. As I’m going at it she’s yelling, "Nick! Nick!" the name of the first guy. After I was done the fourth guy went in. Evidently she sobered up because she cut him off.
The bad thing about it was the next day we go back to school expecting to face her but she’s not there. She didn’t show up until three days later and pretty bruised up. Turns out her boyfriend came back that night after we left, figured out what happened and beat the crap out of her.
Being from a small town and stuff, you know, loose lips go flying and people hear about stuff. To this day, here I am in my 40s and whenever I go back to Nebraska I still get people coming up to me and asking me if that’s true.