By the time I was 14, I knew my way around a boy. Kissing, groping, dry humping…hello, Jordan Catalano in the rain, motivation enough for a girl to find her way around a pant bulge or two.

You know, everything except that whole all the way sort of thing.

It wasn’t for lack of trying, in fact, I clearly remember planning to maybe do it with my 8th grade boyfriend on my birthday, only for him to dump me on my front lawn the night of my party for a girl who lived in Georgia that was technically his 3rd cousin. In hind sight there were signs, but at the time, it was a devastating blow to my self esteem. He’d been my first long term boyfriend. He wrote me poems about death, but in a really romantic sort of way. He was also a gigantic pot head.

Sure, the joint rolling skills would come in handy down the line, but I had learned to tolerate Metallica for this kid, now what was I going to do with all these skull t-shirts?

As I collapsed on my knees onto the cold grass, tears and heavy black eyeliner stinging pooling in my eyes, I felt the stupid metal wrapper of the condom I’d stolen from the drug store in my pocket, and decided right then and there, I was definitely not going to try to have sex with anyone ever again, especially people who would rather be making out with their relatives.

That’s how babies get born with two different colored eyes and their asshole on their forehead.

Heaven forbid they teach that in health class.

Lucky for my still-intact virginity, I was able to transfer from the stoner group to the much more pastel friendly semi-popular crowd, and aligned myself with the teachings of the bible. More specifically, Beverly Hills 90210. I would apprentice under the guidance of a one, Donna Martin.

Like Donna Martin, I was self conscious about my nose, had two different sized boobs, and, feeling like I had nothing else of value to cling to, decided that saving myself would be my best option.

High School was much different than Junior High. In Junior High, you could get almost anyone to go steady with you, as it often had a shelf life of only two to three weeks, and puberty had left all our genitalia collectively weird and unfinished looking, so expectations as a whole, were low.

But to get a boyfriend in High School, you were either the pretty girl, the pretty girl’s somewhat attractive from far away friend, the little sister of a really popular girl, or the girl who’s parents always had alcohol in their fridge. I was the latter. My parents always had beer, and since they were often otherwise occupied running our flailing family video rental store, it was routine for friends to crash at my house for the weekend and reach our two beer tolerances while watching Tommy Boy.

When my best friend started dating a wrestler from a high school two towns over, keeping in line with our blood pact to have a double June wedding and walk down the aisle to Always by Bon Jovi in matching dresses, she fixed me up with her boyfriend’s cousin, Kent, who aside from his state recognized wrestling prowess, was also rumored to only have one testicle after an unfortunate corn harvesting accident in his youth.

I went into this with low expectations. My parents were out for the evening, so we invited the boys over for beer and a game of quarters. From the second I answered the door, I was smitten.

Kent looked like Maxwell Caulfield somewhere between Grease 2 and Empire Records, and he smelled like car exhaust and Calvin Kline’s Obsession. He was beautiful in a way only Greek statues and gay men were. Balls, schmalls. Who needs testicles when you looked like intercourse in Men’s Express jeans?

The evening was going swimmingly. We laughed, we drank, we quoted Adam Sandler, and when the other two ducked out for a “walk,” we quickly found ourselves collapsed onto my pink canopy bed and french kissing to Live’s Throwing Copper on repeat in the CD player on my nightstand.

As he unbuttoned my jeans, I was thankful I had decided last minute to forgo my standard Catholic white cotton briefs and borrow cute satin underwear from my atheist friend Andrea.

Fungal infections. Health class. Take notes.

But then, Kent started to unbutton his pants, and I began to get a bit nervous. Not only was I scared to death to reach down there to find uno ball, I had absolutely no intention of having intercourse with him.

Listen, Kent…I’m sorry, but I don’t want to have sex with you right now. I’m still a virgin, and I’m sorta doing this thing where I am waiting.

It was exactly like every episode of Degrassi, ever. I closed my eyes, thankful that the room was dark and he couldn’t see the fear in my face. This guy was way hotter than me and here I was, declining the only one balled bone being thrown at me.

Brittany, it’s fine sweetie, seriously.

Hold the phone, I don’t care how many balls this guy had, he was getting a hand job.

We kissed again, he was super good at it, and as my hand made it’s way down his chest, towards his hips, in one fell swoop he flipped me onto my stomach, pulled my underwear down and smacked me on the ass.

Ok fine, he was a spanker. I had totally seen this sort of the thing in the porn movies we snuck from behind the red curtain of our video store. Adults spanked each other all the time, and often had sex with pizza guys and plumbers.

He leaned over and kissed my lower back. This was getting weird, right? I needed to consult my friend, but God knows where she was, I didn’t have a cell phone, and Steve Jobs hadn’t even invented texting yet.

As I begin to run through the scenarios in my head that would result in us just chilling on my bed and playing Guess Who, only the best 90’s game ever, I felt it.

A firm poke to what I would later learn was my taint, followed by sharp, excruciating pain. My eyes watered and a guttural groan of shock and distress poured from my lips.

What was that!?

Well, you said you didn’t want to have sex, and I figured this didn’t count-

What is wrong with you, girls don’t have sex in their butts!

I was fresh out of Catholic school, and while my mother was a staunch liberal and my dad was agoraphobic, I was still very much under the naive impression that the only people to have anal sex where homosexuals and druids. And at the time, I was neither.

I jumped up, covering my ass with my teddy bear and my vagina with my hand as I backed out of the room, down the hall, and into our half bath.

Never mind that it would be days before I could comfortably sit in a chair again, I may have just had unprotected semi-butt sex with a charming homosexual/pagan boy in my bedroom, how does that even happen?

Thankfully, by the time I rejoined Kent in the living room, my friend had returned, and the boys had to head home. I walked him to the door, he kissed my hand and was all, can I take you out next week, and I was all, yeah for sure, but in my head I was like, you are the craziest motherfucker ever.

As my friend and I laid on my bare mattress that night, I confessed to her what had happened.

What the fu-

I know, right?

We spent the rest of the night in silence.

My ass hurt so bad, how did Pedro from Real World even do this?

Wait, are my butt and my vagina connected? Oh my God, can you get pregnant from anal sex?

Was there even enough sperm in one testicle to make a whole baby?

My period came three days later. I dodged Kent’s calls for an entire week.

I never dated a boy with one testicle again, and it’s why my backside is guarded by a trio of goblins from Gringott’s.

(Don’t feed them, they look like pets, but they’re working.)

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