My 9 Awkward First Times

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The majority of my sexual experiences have been awkward. Not traumatic “Show-me-where-he touched-you” awkward, but like “Wow, did-that-really-just-happen?” kind of awkward.

First, a little background of my upbringing. I was raised in a moderately conservative Christian household. I attended a private Christian school and signed a “virginity pledge” when I was 13 (a lot of good that did.) I never had “the talk”. The most sex education I ever had was in the 5th grade when my teachers told us “The sperm meets the egg and a baby is made, but only if you’re married.” I left my sheltered world of chastity and innocence after I graduated 8th grade and transferred to the wild world of public high school. I was self-taught sex, and damn, I learned a lot.

1. The first time I ever touched a penis

I was 15. I was in the backseat of my mom’s Suburban as we were driving home from a day of wholesome fun at Six Flags. My “boyfriend” (a guy I liked) was in the backseat next to me. He grabbed my hand and put it in his pants. Why and how he had an erection with virtually no stimulation on my part still remains a mystery to me. It was dark. I was mortified. The song “Creep” by Radiohead was playing in the background. I squeezed this unknown vessel with question and uncertainty. It was definitely not sexy. As I worked my hand up and down this mysterious flesh pole, I was reminded of my dad’s pet snake that would use its muscles to escape my grasp when I held it too tight. I had no idea what I was doing and what this was supposed to accomplish. It didn’t feel good, at least not for me anyway. But this guy must have really enjoyed it. His snake started twitching and rhythmically spurting warm, gooey fluid onto my hand. Like I mentioned earlier, it was dark so I didn’t know what it looked like. Maybe partially melted butter or warm tapioca pudding. It also made a weird, sloppy, wet squishing sound. I guess it’s a good thing his climax coincided with the climax in the song, or else our backseat shenanigans probably would’ve been exposed. I was pretty grossed out and confused, and maybe slightly scared that I would get pregnant or something, so I promptly wiped the goop off onto the seat. Who would’ve known that this would be the first of many backseat adventures to come (pun intended).

2. My first kiss

I was in a slide with a boy named Ryan while we were playing “The Floor is Lava” at the park. I was 5-years-old.

3. The first time I masturbated

It was with a banana and some ice cubes. I had my first orgasm. Don’t ask; it’s kind of embarrassing.

4. The first time I gave a blow job

It was during The Spongebob Squarepants Movie. My mouth was full and I didn’t know what else to do, so I swallowed. It wasn’t that bad.

5. The first time I got fingered

Was on a toilet by a college guy at a party. Not my highest point, but we were drunk.

6. The first time I got eaten out

Was on the hood of a 1999 Nissan Frontier in the cul-de-sac of my parent’s house under a full moon.

7. The first time I ever 69’d

It was after a high school football game while a porno was playing in the background. We were super high. His parents came home early.

8. The first time I had sex

Uuuhh, which time? When I was in high school, my friends and I played a game called “Just the Tip”. It’s pretty self-explanatory, and as you can imagine it made determining virginity a bit more complicated. It was like trying sex without actually having sex.

9. The first time I actually had sex

It was after Senior prom when I was 17. It was intentionally cliché. It was with my boyfriend of a year and it also happened to be Mother’s Day. It didn’t hurt as bad as I thought it would. And I wasn’t drunk or stoned either.

For now, I am more than satisfied having monogamous sex with my hot ass boyfriend. Even though our first time started with a game of “Just the Tip” while the Beck song “Loser” was playing in the background.