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

by Wickens, Shawn

  I met my husband at this very bar. I had met him on my birthday and like three months after that we decided that we were going to buy a house together. All of my friends and family were very much opposed to it because they had never met him and they thought I was making a rash decision. I was making a rash decision absolutely but I was thinking with my heart and so I went with it. I have no regrets. None. And it’s all worked out very well.

  First came the anal sex, then the house. But yeah, when I met him I had never been fucked or fucked. Never had sex with a woman, never had any interest in having sex with a woman.

  He is actually three years younger than me and he’s had a lot of experiences. He studied acting in New York and he slept with everyone under the sun. I thought I was a whore until I met him. Luckily neither of us were unfortunate enough to contract any diseases. But he was very much more experienced than me and he totally eased me into it. He eased me into anal sex with one finger at a time and he even made me a mix CD with songs pertinent to us back then and he titled it "One Finger at a Time." I had never had anyone else put his dick inside me and I've never put my dick inside of anyone else and I have to say that I am very, very, very happy and not looking to stray.

  Having someone who knew what to do certainly helped with the physical aspect of it. He was very understanding and very patient. I can't emphasize that enough – very patient. Because... when you put things in your butt... it hurts. Eventually you grow to get used to that sort of thing but it takes lots of work.

  He was living at a repertory theatre and that was the first time I had sex was in his bed that he was renting backstage and it was amazing. The fireworks were there.

  THE VELVET REVOLUTION

  Lienhart, 38

  I'm from the Czech Republic and this happened back in 1989. At that time there was this huge change that began to happen that resulted in the ultimate removal of the Communist Party as the only source of power, the holder of power. The whole event started as a wave of public disagreement that was sparked by the university students.

  I was a senior studying biology at Purkyne University in Brno which is a central city in Moravia in the eastern part of the Czech Republic, or what used to be the central part of Czechoslovakia. I was about to finish my undergraduate degree when all of the students went on strike, occupational strike. Suddenly we went from simply studying at this institution of learning to being in charge and we were doing political activism. It was an exciting time to be there. And it just so happened that one of my closest friends had brought his girlfriend into our midst and she became a member of our core group, about a dozen people or so and myself who helped to organize protests and marches and walkouts. She and I had kind of struck this relationship, an interest in each other. We had this sudden outpouring of emotion and closeness and you have to realize that to go out and put your entire life and prospects on the line for the future – it was a pretty heavy deal. And to find somebody who's going to just sort of carry you through that to the next state for our country, or even the next morning was an incredible thing in its own right. This girl, Věra was the one I have given my virginity.

  Really it was just a fling for her although I had wished and wanted it to be more than that. I still think back on losing my virginity in what essentially had been a lecture hall for organic chemistry. It was during the occupational strike at a time when me and my friends were helping to decide the future of our country. No matter how cynical you might be looking at that era or even the current state of the world, looking back at that specific moment, it was a grand thing.

  The truth is, is that she and my friend got together later again. And later still she left him and went back to a man who had been her high school sweetheart and the last thing I knew before I left the country and moved to America was that she got married to that man and had a child. I last saw my friend the summer before last. He's gone on with his life; we're still good friends.

  To put it in his words, and I will never really be certain whether he knew what really happened at that time with me and Věra, but later on when we were reminiscing, he said very simply and succinctly, "The revolution taught Europe how to handle women." And that may not have really been the whole truth but it certainly took away some of our naïveté, individually and as a society. I don't think it made me less of a romantic but I think it made me, at the cost of some pain, a wiser man. And if that's not an achievement then nothing is.

  POETRY IN MOTION

  Julius, 41

  When did I lose my virginity? It happened so fast. Mmm... trying to think back through my sex life. It started I guess... before my puberty. So then... yeah, the official one would have been this lovely girl. Her father was the headmaster at the local school. We were both in the same school... and... oh, it was wonderful. We took the whole day off... you know, little kiddie stories. We just were off playing in the fields of Ireland. Got off school for the summer and spent the whole summer making love. But school didn’t end, I guess. She taught me how to make love.

  We... we... we gaffed off school… got in her car, and then got out of the city and into the country... and I was shaking like an idiot. She was like the leader... beautiful, voluptuous girl. And... I couldn't get out of her breasts. She went down on me... it was all over. It was very embarrassing. And then... after another while... awkwardly I mounted her... and I... slipped into her. It was warm... gorgeous... ah, it's coming all back now. And it was over like that, snap.

  I'm thinking... trying to get into the mood of that time... it was all very slutty... there was no love involved at all. Just pure lust, testosterone and hormones and… I woke up in a puddle of confusion. I saw her naked body… and the head of my penis was ripped to pieces. And the faces that people make when they make love... it's like a donkey - the most ugly faces in the world.

  We were done and we drove out of the country, into the city. I think we had a bite to eat and had a swim. And then... we couldn't keep our hands off each other for the whole summer. It wasn't like, "Hey you wanna go out somewhere and do something?" it was, "Let's go and fuck. Let's go and fuck." We were fucking on top of wardrobes, in supermarkets, everywhere... experimenting all over the place. And the more risqué the better.

  And of course we thought it was forever. But... she basically fucked my brains out for the summer. Then she moved on, and I… masturbated for the winter.

  She was going to be a concert pianist, and I was going to be a world famous artist. Then she became a music teacher and I became an underground, dropout artist in the Chelsea Hotel. Heh... what a time.

  Chapter 7

  "JUST FELL INTO IT"

  It’s a common feeling to get swept up in the moment during the first time, even more so when your mind is racing, "I can’t believe this is happening." Some people plan for the moment and stress to make everything perfect. Others just luck into it. Some first times are engineered, others are serendipitous.

  A few more same sex-stories appear in this chapter as opposed to other chapters. When you grow up heterosexual and you’re dating, even if you’re just around members of the opposite sex, the possibility of sex, no matter how slight, is right in front of you. But when your sexuality is a secret, the opportunities are hidden and make for more spontaneous or accidental experiences.

  REMEMBER THAT FRIEND OF YOURS?

  Craig, 25

  I was a late bloomer. It was my second year at Penn State when I finally became very dissatisfied with how college was going for me at that point. I was involved with a few girls but never got up the mustard, the "minimals," as they say, to finally carry it out.

  We had a party at my apartment and a bunch of friends were there. My younger brother went to Penn State too and he brought along one of his friends, Janet. They were in the same year. Everyone is hanging out. It’s the various college ways and means of partying, especially at Penn State. Various drugs and stuff involved. Mostly alcohol and pot but very large quantities of the two.

  After the party s
tarted to wind down I went to the living room and started watching American Beauty. I was changing from mathematics to a film studies major so this serious movie was just one of those movies in college I was inspired by. Janet, my brother’s friend, wanted to watch the movie with me so it was just the two of us.

  It’s the end of the night, as I said, and time is winding down. All of my roommates are passed out in their rooms. She’s sitting there on the couch next to me and I figured something was going to happen. Her head went down in my lap and there was nothing holding us back at that point. I mean, it was obvious. It’s three in the morning and the room was pitch black except for the television. I guess she was just looking for affection. From what my brother later told me she wasn’t much enjoying her experience at college. She wasn’t finding her place and I think she was just looking for someone who seemed confident with their surroundings.

  She came close and cuddled. I thought, "Let’s just do this, get it out of the way." So we started kissing.

  I don’t believe it was her first time. I think for her it was just a college hook-up. Maybe she was under the impression I was a seasoned veteran and I didn’t tell her anything that would make her think any different. We started going at it on the couch and it was a terrible couch. A college piece-of-trash couch. No sort of comfort involved whatsoever. It was hard to move around. Finally I sat back and let her get on top of me and because of the alcohol and drugs I was having trouble physically responding.

  We’re going at it and finally I’m building up, I’m building up and I say to her, "Oh, I’m about to cum." She’s out of it as well and since we were going for so long and we were so messed up, she must’ve heard, "I can’t." She gets up and starts apologizing, "Oh, I’m sorry. I’m sorry." I was sitting there dumbfounded by the situation. I was thinking, "No. Don’t. Stop," but at that point it was already ruined. So I just separated from her, let her sleep on the couch and I took the floor.

  The next morning everyone woke up and just saw us on separate places, you know, my roommate was hooking up with his girl in our bedroom and she felt bad that I got relocated and got stuck sleeping on the floor. Little did she know that I was having sex with her friend in the living room.

  I’d see the girl I slept with on the street here and there, waking around campus and such. My brother, Chris, would talk to me about, "Yeah, I saw her the other day." And I’d be like, "How did that go?" I’ve still never had the brass to tell him I had sex with his good friend.

  THE ACCIDENTAL JOHN

  Marcus, 33

  There was this girl who lived in my neighborhood in Makersfield, Northern England, and for a pound she would take you to her room and let you look at her with her clothes off. I was 13. She was 15 or 16.

  I lied to my dad and told him I needed to get a book for school so he gave me a fiver. And everyone in the neighborhood was going over this girl’s family’s house. The parents were out, her younger brother was downstairs and she was upstairs in the bedroom.

  So it was an investment really. And it was worth it, haven’t done anything like that again. Everyone else was just looking, but the five-pound note got a little bit more. She saw that and it was full-on sex. Kept my Doc Martens on and that was that. Everybody else kind of knew something was going on ‘cause I was in there a little longer than everyone else.

  My dad asked me about the book as I was supposed to give him the receipt, which I told him I lost as was par for the course.

  I CALL SHOTGUN

  Curtis, 49

  It was with an acquaintance, a friend of my nephew’s. She and I weren’t boyfriend and girlfriend, she was just someone I knew. We had gone out to a concert one night. We were young and we were out partying.

  My nephew and I are very close in age. He’s actually six months older than I am. My older sister was pregnant and then I came along – an accident.

  So we’re out drinking and we’re in my nephew’s Trans Am, which was an easy car to pick up girls in. We went to a lot of concerts back in the day. My first concert was, I think, Vinegar Joe with Mahogany Rush, but I don’t think this happened after that show. We had a long drive at the end of the night all the way back Mobile, Alabama. We had a good time and then we partied and drank the whole ride back to Lucedale, Mississippi. We were riding around drinking just like always and we just decided to stop at a creek bank. I could sense what was going on, it was obvious but I was scared about it.

  I don’t remember whose idea it was, maybe it was a mutual decision but somebody said, "Hey, let’s go skinny dipping." Soon enough we were butt naked on a creek side in Mississippi basically half in and half out of the water, like an amphibian experience. Not quite as romantic as From Here to Eternity.

  Who slept with who was as much determined by who you were sitting next to in the car as much as anything else. It was very indiscriminate. She was a fairly aggressive young lady and we came together more as an act of nature than anything else.

  It was wild the way it happened. And it was my first time and I was anxious and it was kind of anti-climactic, but sort of not. It was more just weird for how detached it was. Had we not been partying and drinking it probably never would have happened.

  AWAKENING

  Damon, 26

  When I was 18 or 19 I was in the military at Fort Knox, Kentucky. One of the other recruits came over to my bunk and called me by my last name, "Wake up. I gotta talk to you." It was about three o'clock in the morning and we only got maybe four hours of sleep anyway, so I was like, "Yo, take your ass to bed." He said, "OK," only I didn't hear him walk away. He didn't move. I turned over and he's like, "All right." I'm like, "All right, what?" And he goes, "All right I'll suck your dick."

  I was on the top bunk. I pulled my dick out and he started working it. I changed my mind and tried to pull away but he didn't let me. He sucked my dick and it was the best suck I ever had. There were 50 people in our bay and they had to have known what was going on, but it was weird, nobody said anything.

  I was the greatest, straightest man before that happened. I had nothing to do with homosexuals, so when it happened it was, I don't know, dynamic... different. After that I was hooked.

  MERRY XXXMAS

  Randi, 23

  I was 16 and a half and it was the day after Christmas. I was with my best friend Bella and we decided to go next door to Heather’s apartment, who I’ve known since I was two. It was me, my best friend Bella, Heather, and her boyfriend Daniel. We were totally alone drinking vodka. It was the first time I had ever consumed alcohol.

  I can’t remember what game we were playing, one of those games you act out stuff like "truth or dare", but Heather said something like, "Hey, how about we have a threesome," and I was like, "OK." And it quickly turned into a threesome with me, Daniel, and Heather. Bella sat in the back corner and watched. It was very surreal.

  We took off our clothes, and I fingered Heather for a bit. We all fooled around for probably about an hour and a half with Bella just watching the whole time. Then it was mainly Bella and Heather watching me have sex with Heather’s boyfriend. But it seemed everyone was having a good time.

  The next day Bella asked if I felt different. I was like, "Not really. I just feel like I got something out of the way." But it was very awkward for me because I had known Heather for so long. Still every time I see her it’s in the back of my mind, "Wow, OK. I had sex with your boyfriend while you watched." Very weird.

  I ran into the boyfriend two years after it happened. He put his arm around me and was like, "Hey, Randi. How you doing?" I was just like, "I’m great. Go away."

  THERESE’S BIG ADVENTURE

  Therese, 36

  It was my sophomore year, so that would’ve been ’84. I had just turned 15 and my friend Kimberly and I went to go see Pee-Wee’s Big Adventure. I was a huge Pee- Wee fan so I had to go see this movie. So we went and we loved it… well I loved it. We came back to my house around 10 o’clock, 11 o’clock at night and got a call that a bunch of our friends we
re at a party up the street.

  Kimberly and I walked the quarter of a mile, half mile down to this kid’s house for the party. We get there and everyone was like really, really drunk. As soon as we arrived my friend Job pulled me aside and started explaining to me that out of all our group of friends there were only two virgins left – me and Heath, who had been my best friend in grade school. Heath and I were the only two left so Job was like, "Look. Therese. It’s kind of retarded at this point. You should probably just do it." Before then I had never really felt embarrassed by the fact that I had waited.

  Here’s the back-story on why I was the last girl in my group of friends to lose her virginity… or why they did it first. We had this other friend who was an only child, really, really brilliant – she’s like a Ph.D. in biology now. Growing up she was really wild and really, really slutty.

  The previous summer she picked up some dude at this resort hotel near where we lived. It used to be like an old Playboy club so they had a pool and everything and it was real swanky. Her dad used to take her there to go swimming. As I heard it, she was walking around the arcade one day and this dude, like this townie kid, threw her just a little bit of attention… she wasn’t particularly pretty… he threw her just a little bit of attention and he took her into the stairwell and fucked the hell out of her.

  Subsequently she fucked all his friends, I’m talking within the first month that they knew each other. Then the friends of his that she didn’t fuck, she pimped out all of our other friends to fuck the guy’s other friends.