Ten years ago, I had sex for the first time. 

After all this time, I still remain completely clueless on how to please a woman.

My partner was a gorgeous (out of my league, which isn’t hard) sixteen year old and I was head over heels in love.  Like murder suicide kind of in love.

Probably the last sixteen year-old I’m ever going to have sex with.

Probably.

My parents would let her sleep in my room, in my bed, almost every single night and not say a thing.

I thought they were naive, or stupid, but they just figured it was the best I ever was going to get, and they were right.

Her and I were catholic, so we had an incredible amount of guilt about having sex, so for the first six months we’d pretend to be sleeping and just dry-hump for hours.  Probably so we could maintain plausible deny-ability.

Now, dry-humping is fine for a girl, but prolonged rubbing, over clothes in the pelvic region is hell on Earth for a guy.  If you ever wonder why a guy’s penis has a crazy amount of curve towards his torso, he’s spent most of his youth dry-humping adolescent girls in terror.

I got a girlfriend and suddenly orgasm WAY LESS.

And I was the idiot, because it took me three months before I started wearing sweatpants, I was wearing JEANS the entire time.

The sound of denim rubbing up next to each other still cause me to scream in terror.

To this day, I have a zipper scar on my scrotum that says DKNY.

Luckily, it’s over the part of your balls that looks like it’s been sewn together with a needle and thread.  What’s with that?

God needed a needle and thread to keep your testicles inside your body?  It’s so weird.

Everyone else has that, right?  It wasn’t some sort of accident my parents never told me about?

So after six months of dryhumping, we finally decide to have sex.  But under one condition.

She still wanted to be a virgin for God…

so we had to have sex in her ass.

…

Which was fine for me, I was just glad that the catholic faith had such an amazing loophole (and what a hole).

God doesn’t see anal sex.

…

Which means Jerry Sandusky is going straight to heaven.

The logic of the situation had almost exploded my mind, but I really wanted to lose my virginity so I wasn’t about to start arguing with her.

I was experimenting with lubrication for years already by myself and I had nothing in my room that would facilitate her request.

So at 3am in the morning, I tip-toed to the kitchen looking for a lubricant to dissolve my v-card.  Having no time to lose, I was completely nude, and with a bouncing erection that was stealing most of the blood originally allotted for my brain.

Opening the fridge, I saw a container of cake frosting.

Cake frosting would’ve worked perfectly, but the only flavor my parents had bought was chocolate.

Visually speaking, having anal sex with chocolate frosting..

Not what I was going for (at least for the first time.)

At this point, I was almost ready to just pass out out of sexual frustration, when I remembered.

We had a big can of olive oil underneath my sink.

So I grab a cereal bowl, because I wasn’t just going to poor the olive oil into her anal cavity like she’s a Mazda Miata.  I had a deep love and respect for her, I wanted it to be as beautiful a moment as possible, and me on both of my knees, pouring copious amounts of olive oil into her anus would not be characterized as a “beautiful moment.”

I reach under my sink, and I get a message from god:

“Extra Virgin” Olive Oil.

How right they were.

As I turned back to my room to finally lose my virginity.

My mother was standing at the doorway, she had seen the whole thing.

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