My First

12 May

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, Artsy Gal, 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.

Artsy Gal 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.

Artsy Gal 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.  Artsy Gal met Artist Loser.  They flirted.  He invited her back to his house.  We all went.

Twenty minutes after arriving at Artist Loser’s house, Artsy Gal was in his bedroom.  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?

Artsy Gal 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.

19 Responses to “My First”

  1. Amadeo May 12, 2008 at 12:45 pm #

    Awww…I’m all verklempt.

    And I know nip when I see it…your cartoon avatar is a saucy wench.

    Damn it! There’s no nipple! -CS

  2. teri May 12, 2008 at 12:55 pm #

    I’m actually surprised that you have mutual friends, to this day. Weird!

    Oh yeah, and you’re a fluzzy! Does that make you feel better?

    The best was that my first day at this job (11 years ago) the very first person that I met knew him from high school. Small world. -CS

  3. Holy Crappers May 12, 2008 at 2:18 pm #

    What a sweet story.

    To be 17 again……ahhhhhhh

    I especially loved the jacket on jacket idea. You were bringing sexy back and you didn’t even realize it 🙂

    Peace 🙂

    I’m totally going to bring the 2 jacket thing back in style…even if it was never in style. -CS

  4. Del-v May 12, 2008 at 3:06 pm #

    If he had a “Taz” tattoo like 99% of people who willingly wear WVU sweatshirts in public you might not have been so impressed.

    Come on now. As a college kid you knew that WVU was cool-that was THE party school to go to. -CS

  5. cinnkitty May 12, 2008 at 3:27 pm #

    Awww… CS.. I’m disappointed that you even bothered to get his last name.. ha..ha..ha..

    What a lovely, charming, romantic story that I hope you NEVER relate to any of your children/nieces/female cousins, etc… It wouldn’t due to contribute to the delinquency of a minor. 🙂

    I actually tell the kids that story everytime I babysit. My nephew loves the part with the bicycle. -CS

  6. Red May 12, 2008 at 3:41 pm #

    You’re not a whore, babe. You aren’t in it for the money.

    This story would never have happened to me, but if it did, I would totally remember the date, too.

    Did you end up going to prom?

    You don’t know. I might be doing it for drugs and money. Or at least for booze.

    Nope, never made it to prom. -CS

  7. thenextfish May 12, 2008 at 3:54 pm #

    What a brilliant story; so did you walk across the stage at graduation thinking ‘thank god I’m not a virgin’?

    I’ll guess the suede jacket was an attempt to hide the ugliness of the linen blazer.

    Pretty much. I accepted my diploma, thanked my lucky stars that I had given it away before heading off to college, and then sauntered back to my seat in my very fashionable white dress.

    I’ll have you know that the linen blazer was quite lovely. It was from the Gap-which was still cool back then. -CS

  8. Jenna May 12, 2008 at 4:01 pm #

    I’m quite impressed by your powers of recollection. It takes me a minute to remember when mine was and while I remember his first name and some of the important details, his last name and the specifics (like what he was wearing…are you kidding?!) are long since gone. Good on you.

    Really? I thought all girls remembered the important details from their first time. -CS

  9. Philly May 12, 2008 at 4:10 pm #

    This would be a great Lifetime Movie !!

    You don’t think it’s too racy. -CS

  10. Beth May 12, 2008 at 5:07 pm #

    Yours is a better story than mine. My First Peen had me get on top and do all the hard work because he had a problem with PE. And, yep, he E’ed the moment I got him in.

    Never went out with him again.

    Please tell me that you were his first Vagena Rowlands? Otherwise, his behavior was unacceptable and it totally shouldn’t count (as per Georgia’s 4 Pumps rule). -CS

  11. Foxy Luv May 12, 2008 at 6:26 pm #

    ‘My First Peen’ – its like some sort of perverted doll for tweener girls. With a cheesy theme song like the My Buddy doll had. And the add ends with the little Tweener girl giving her ‘My First Peen’ doll a kiss as they snuggle in her frilly pink canopy bed and saying, ‘I love you, my First Peen!’.

    So sick! Wait…does any one have the number for the Hasbro people?

    Hey, when you call Hasbro, make sure you tell them about the accessories that come with the doll. GED and conversion van are sold separately. -CS

  12. the princess May 12, 2008 at 6:28 pm #

    i also remember what I wore the night i got my first peen. funny. 17, so young, so easily melted.

    whore! hehe

    It is funny the things that we would fall for back then. What’s not so funny are the things that we may fall for now… -CS

  13. Sunshine May 12, 2008 at 8:56 pm #

    WVU — > party school, way back in the hills of Good Old West Virginnie… I think all the guys there drank and pimped out their peen for the ladies.
    To be 17 again… what I would do differently? You took all of us back to our “first” peen… I was in a park near a vets grove and in the back of a station wagon… classy, I know. He didn’t know it was my first and yet was surprised to hear that a couple weeks later. What kind of moves can one possibly make in the back of the station wagon. ( to make things more laughable, I was on top! )

    My dear, Sunshine, on your first encounter you managed to do something that I have avoided at all costs: doing it in a car. Way to go! -CS

  14. romi41 May 12, 2008 at 9:20 pm #

    What a lovely tale of your introductory peen!!! 🙂

    And call it a one-night-stand if you want, but I’d still fall for that romantic moon-talk today (and I’m only, umm..10 years removed from age 17 😉 )

    You know? I’d probably totally fall for it too. 🙂 -CS

  15. Bob Dobalina May 12, 2008 at 11:29 pm #

    I love hearing about people’s firsts and this story is exactly why. You perfectly captured it and it was funny as hell.

    I think I’ll do mine and call it a tribute to you. That sounds so much klassier than ‘blatant effing theft’. Mine ends with me whispering seductively into the girl’s ear:

    “if we don’t stop RIGHT NOW I will be sick all over you… baby”

    Wow, Bobby D (which is what I’m totally going to call you from here on out), you really know how to romance a woman. I can’t wait to read all about your first time! -CS

  16. Max Candor May 13, 2008 at 12:12 pm #

    Fantastic story. It is great to hear the perspective from the other side.

    I’m dying to hear one from the male’s perspective.

    Here’s what I think My First Peen would say:

    I met this girl. We went to her condo and we did it. I can’t remember her name.

    Or you know what? It was so long ago that maybe he doesn’t even remember it! -CS

  17. pistols at dawn May 13, 2008 at 8:41 pm #

    Your friend sounds hot. Still have her number?

    You know what? I do. But she’s a lesbian now. -CS

  18. Newmie May 15, 2008 at 9:09 am #

    Sadly, my first peen wound up being a groomsmen in my wedding. Probably should have seen that as a sign to not get married.

    He was uncircumcised to boot. SCARY!

    I win.

    I’ve never seen one of those up close. I wouldn’t have the slightest idea what to do with it. -CS

  19. Ginormous Boobs May 15, 2008 at 11:48 am #

    Bobby D is still romancing the ladies that way. He whispered that tired line in my ear the other night!

    Know what’s funny? He emailed that to me just this morning. -CS

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