I was 17 when I lost my virginity. Sure he didn’t drive a conversion van and he was a high school graduate as opposed to just having his GED, but it was still a klassy time.
It was a Saturday night in May and my girlfriend, Only Dates Losers with Major Problems, and I were down at the beach. Her family had a condo on 98th Street and she and I had gone down for the weekend. Back then, our idea of a good time was driving around, staring at cute boys and maybe shouting at them while we drove by. God we were so freaking cool.
I could tell you exactly what I was wearing that night: blue jeans, black flats, maroon tank top, black linen blazer, and a brown suede jacket. Look, I was 17 and it was the early 90’s and the outfit made sense at the time. Lord only knows what possessed me to wear the suede jacket in May and over the linen jacket. Stupidity is my guess. Oh, and I had white Victoria’s Secret panties and my brand new graduation bra on. It was my graduation bra because I was going to be wearing it under my graduation dress 2 weeks later. The bra had a cute little button in the front. I loved it.
We were cruising in my SAAB 900 when we saw these cute boys-one of which was wearing a WVU sweatshirt and pushing a bicycle. Little did I know that this would be the young man that would be the first to use his peen on me. Yes, I had seen a peen prior to that, I had actually held it in my hand, but we didn’t do it.
Only Dates Losers with Major Problems and I immediately drove around the block and caught up with them. Witness my mad flirting skills:
- CS: Hey, you!
- My First Peen: Hey yourself.
- CS: Where are you guys off to? Need a ride?
- My First Peen: [Stares down at his bicycle then at me] I think we’re set for the ride, but we’re going to a party. You should totally come with us. It’s at 611 7th and St. Louis.
- CS: Cool.
- My First Peen: Yeah. Cool.
So Only Dates Losers with Major Problems and I drove the 3 blocks and met them there. There we were standing around at the party feeling so awesome that we were hanging out with college boys while we were still in high school. They offered us beer, we passed because we were stupid and thought we were too cool to drink. If only I had known that I would spend half my college life in a drunken stupor… I flirted with My First Peen. He spilled my beer on my suede jacket. Only Dates Losers with Major Problems met Artist Loser. They flirted. He invited her back to his house. We all went.
Twenty minutes after arriving at Artist Loser’s house, ODLwMP was in his bedroom, on her knees with his dick in her mouth. The girl worked fast. There I was in the living room twiddling my thumbs trying to figure out how I was going to extricate myself from the situation. Suddenly, My First Peen announced that he was leaving. I took this as my queue and offered to drive him back to his hotel (even though it was 4 blocks away and he had his bike). Sensing that there would be boobies in his immediate future he agreed.
We ended up in his hotel room. We were talking about my upcoming prom. I used my mad skills to tell him how boys never asked me out, and I didn’t have a date to prom, and how shy I was, and woe is me I’m so pathetic. He fell for it. Somehow we got on the topic of tattoos and he showed me the tattoo of the moon that he had on his right thigh. Next thing I know he was laying on top of me and we were making out. It was at this exact moment when his drunk friend bursts through the door and ruined everything. Super. Great. Drunk roommate passed out, we continued making out. Suddenly, something came over me (no pun intended) and I whispered, “Do you want to come back to the condo?” He lifted his head, staring at me like I’d just told him that he had a winning lottery ticket and him saying, “Uh, yeah!” He dragged me out of the room like it was on fire and we might die if we didn’t escape.
The drive took about 15 minutes and I remember thinking, “What the hell am I doing?” This was out of character for me. I was a virgin. I’d only hooked up with one other guy before. But graduation was just a few weeks away and I was not going to be graduating a virgin. Hells to the no. I had to get rid of it, and My First Peen was cute, and charming, and if he wanted it, he could have it. He said lame cheesy things to me, and I melted.
We arrived at the condo and he told me he wanted to show me something (I’m not talking about his peen). We went out on the balcony and the sky was starting to get light. There was a quarter moon and one star left in the sky-I remember the exact position of the moon and star and the color of the sky. He pointed out at the moon, and said that this was the exact reason he had gotten his tattoo. If I heard someone say that today it would cause me to roll my eyes. At 17, this was the most romantic thing that I’d ever heard.
We made out on the balcony.
Then I dragged him into the guest bedroom, and that’s where the magic happened. I’ll omit the details because I totally know you don’t want to hear all of that. I will tell you that I didn’t mention to him that I was a virgin, though I’m pretty sure he figured it out the second he heard the sharp intake of breath. I was completely unprepared for the pain. Thankfully, that first time only lasted about 10 minutes. When we did it again later, it didn’t hurt. I do, however, remember being bored and looking at my fingernails. Can you feel the magic?
ODLwMP came home about 8:30. I heard her come into the condo and went running into the living room to tell her all about it. There was a naked sleeping stranger in her great grandmother’s bed (because I’m klassy and that’s how I roll) and we were on the balcony spitting out the details of our boundless whoring.
My First Peen finally rolled out of bed at 11:00 and we all got ready to leave. On the way to drop him off we finally learned My First Peen’s last name. I dropped him back off at Artist Loser’s house and we said our goodbyes. We shook hands and said, (I will never ever forget this extremely meaningul exchange) “Nice meeting you.” My girlfriend and I would later retell the story saying that we’d actually said, “Nice mating with you.” I saw him again later that summer. We ended up becoming friends. The crazy thing is we now have mutual friends. I hear about him from time to time.
And that, my dears, is the story of my very first time. A one night stand with a complete stranger. A whore from the very beginning.
Click here because today is the 17th anniversary of me losing my virginity.
