Stamped: January 26th, 2007 | Toggle Similar
Tagged: dates of yore, dating hijinks, hot sex, iPod, music.

My sexual history is a sordid affair. I’ve had my fair share of good/bad/mediocre experiences. Some of them have even transcended from physical acts to sentimental triggers. Don’t worry my therapist knows all about it.

One thing you should know about me is that I love music. I have a tendency to create playlists in my mind when I’m dating someone that usually end up on my iPod. You should see my iPod, you wouldn’t be able to find the music until you knew which guy it was listed under. So I decided it was high time I narrowed that shit down to one playlist, I think I’m gonna call it my “Sexual Soundtrack”, or “My greatest mistakes set to music.”

Track 1

My first boy-on-girl experience happened in the 5th grade. I blame it on peer pressure, all my friends had been kissed except for me. My poor virgin lips needed to be popped. So I set my sights on a boy named Julio. His was so cute. He didn’t speak a word of English so I got out my Spanish-English dictionary and wrote him a love letter which I translated word-for-word. Unfortunately I found out later that it was completely indecipherable, what did I know about conjugations and all that crap. I told my friends the plan, which had my letter been legible, Julio would’ve also known about. I was going to meet him on the schoolyard for our first kiss. My friends gathered and I cornered Julio near the ballbox. He was taken completely by surprise as I planted one on him. It was, in hindsight, the stiffest kiss I had ever had…and not stiff in the good way.

Track 2

It wasn’t until I was 16 that I would lock lips again. His name was Bleu, you know like bleu cheese, and he was my best friend’s boyfriend. It wasn’t the right thing to do but my 16 year-old body was raging with desire, naughty legs akimbo desire, desire that somehow warped my brain into believing “Oh, Kristy will understand…she knows I’m a virgin and she’ll probably be happy for me.” Thank god her and I are still best friends and can laugh about it today. So Bleu, he was so hot. I lived in Hollywood and he lived in Monrovia and we would take the 1 ½ hour bus ride every other day just to see each other. I would sneak him into my bedroom late at night and in the morning he’d hide in my closet until my mom left for work. One morning I had to leave before my mom cause I had to be at school early so I told him to wait there until he heard nothing. I came home from school that day to find him still there, in the closet. Apparently my mom had left the radio on, on NPR, so it was talk shows all day. He couldn’t decipher what it was and was too afraid to leave. The irony of this story is that we broke up shortly after when I found out he liked boys.

Track 3

Apparently this wouldn’t be my first experience with boys who like boys who like girls who like boys or however that goes. I met Travis when I lived in Berkeley. Cute messy hair, tall and lanky. He was a friend of a friend and we met at one of those legendary Coop Parties in Berkeley. Both stoned out of our minds we went up to his room and started to fool around. We tore at each other until neither of us had a shred of clothes on and I hopped on top of him. But then he stopped me. I was puzzled, “What going on here.” He looked at me and asked if I wouldn’t mind putting my boots back on. I thought it was odd at the time but said to myself, “Hey whatever works” and I said to him, “Ok, as long you smack my ass while I ride you, cowboy.” I did, he did. A few weeks later I found out through a friend of a friend that he was now gay and dating that friend of a friend. To this day I can’t bring myself to watch Brokeback Mountain.

Track 4

After living in Berkeley I moved to San Francisco and despite popular opinion there were plenty of straight men. Suffice it to say my San Francisco years were by far the most sexual years of my life. It was a veritable free for all. And I was a hot little number. Skinny, blonde AND I rode a motorcycle (a little Honda 250, total chick bike, but hey).

Around that time I met Francesco. A nice Italian boy from Calabria. He was always very sweet and polite and gentle. Until he got me into bed. Then everything would change. He would flip me around, spank me, contort me, bite me, scratch me. It was so damn hot. One night we were going at it, he had me on my hands and knees and he was smacking my ass. I must’ve lost my balance because as he gave me a hard thrust I fell head first into the wall. I swear I was seeing crazy colored spots everywhere. But that didn’t deter him, he simply pulled me back up and before I knew it I was coming.

Track 5

I would be remiss if I didn’t mention Angelo. I knew he was trouble when I first met him, something told me to stay away from him. But I was 22 and apparently at that age instinct and common sense are secondary to a gorgeous Puerto Rican pursuing you. We went on a real date, dinner, drinks, then finally back to his place. I was putty in his hands. He kissed me passionately and then pulled back. He said, “There’s something I have to tell you before this goes any further.” Uh oh, right? So he says, “I have…well, how can I put this…I have a very large penis.” I think at that point all I heard were bells going off. But he continued, “I’ve even had girls call me from their gynecologist’s office to scream at me, so I just want to warn you.” I was confident, I thought “Come on how BIG could it be?” Oh my, I don’t think I could walk straight for a good week afterwards.

Track 6

Then there’s the other end of the spectrum. Poor poor Peter. We met through friends and went out on 4 mind-blowingly wonderful dates. He was perfect, we had so much in common. Even our taste in music. So on our 5th date he cooked me dinner, a great bottle of wine, we watched a Woody Allen movie and then he enticed me into the bedroom. Soft slow kissing and my clothes started disappearing from my body. Then he closed the blinds, climbed back in bed and started to undress. There was a sliver of light that peeked through the shutters and I caught a glimpse. I nearly gasped. I saw balls…and what’s that? Oh, a nub. Dammit, dammit, dammit. I tried, I swear. But when he couldn’t even maintain an erection I gave up and we "cuddled". It was then that he decided to tell me that he was on anti-depressants and his marriage broke up because his ex-wife wasn’t sexually satisfied. Duh.

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