My First Encounter With An Uncircumcised Penis Could Not Have Gone Worse


The only uncircumcised penis I had ever seen in my 20 some years of life was in the anatomy lab on a dead, 87-year-old cadaver. Until I met fuckin’ Oscar.

Our tale of romance was as modern as it got those days. We exchanged a few niceties at a mutual friend’s party, I made a mental note that his Redskins hat was kind of hot but made his ears look a little disproportionate, and that the Persian chick following him around was probably his clingy, extremely under-his-league, weirdo girlfriend. As much as my drunken mind wanted to take him straight up to the bedroom and show him what I learned from my Catholic high school, I decided not to be the token raging skank and simply black the heck out on honey whiskey on my own. I didn’t even catch the hottie’s name.

Fast forward three-ish days to me lying in bed, ‘Flix on in the background streaming “The Office,” mindlessly swiping right to every 8 or above to grace my little iPhone screen. I had totally forgotten because I had blacked out the guy’s name, his face, and just about the entire interaction with the guy, because Oscar was apparently my star-crossed lover, we matched.

Oscar: Hey, I know you

Me: Oh god

Oscar: I met you the other night at Dave’s, right? You were the one drinking the Pinot straight from the bottle while trying to impersonate Shakira.

Me: A lot of women do that. It probably wasn’t me.

Oscar: No it was you! How could I forget the most beautiful face I’ve ever seen? And those eyes… goooooodayum. You’re the prettiest, coolest, smartest, funniest girl I have ever met!

Me: Oh! That was definitely me!

Maybe I’m exaggerating that last part, but that was basically the gist of the conversation. We exchanged numbers, chatted for a bit, and kept things pretty short until he invited me over to a party he was hosting. As I’m sure you already know where this is going, I solo pregamed his party, drank all of his whiskey upon arrival, slept with him once the party had ended, regretted the whole damn thing in the morning, but not until after the morning sex. Fill in your own blanks.

Oscar and I continued to see each other on a pretty regular basis. In other words, I texted him every time I was heavily drinking because yes I wanted the company, but mostly because he had a California king Tempur-Pedic, the Cadillac of beds, while my mattress was more akin to the 1995 Volvo Station Wagon with wooden paneling your parents bought you in high school. Sex with Oscar was nothing more than me spreading like a starfish on his bed while he angrily bounced around and grumbled trying to make his dick work. I wouldn’t call it love, but we were definitely getting there.

So one dark, wintery day when I got back to my apartment after a long day, I realized that it was really fucking cold when my nipples chiseled through my industrial-strength Victoria’s Secret bra. I couldn’t afford to turn the heat on (#PGP), so I did the next logical thing I could think of: text Oscar and trick him into inviting me over. I figured we have a little wine, turn on a movie so we didn’t have to verbally interact with each other, and then heat things up a little bit. When he sent the fabulous “why don’t you just come over to my place?” text, I gave myself a little

…And went on my way to the worst sexual experience of my life.

The evening went exactly as planned. We got a little buzzed, but by no means drunk. Hanging out mostly sober was a huge turning point in our relationship, if you could even call it that. The man had quenched my thirst, fed me spaghetti, and gave me the warmth I couldn’t afford, the least I could do was give him a good old blowie, right? Mid movie, I put my glass down, fiddled my way around his brown, leather belt, and gave him the playful “I’m about to rock your muthafuggin’ world” look while my face hovered ever so much above his zipper. I even threw in a couple of fake moans of excitement. Because of his generosity, I wasn’t going to die of hypothermia in my sleep. So I wanted to give the guy a show, you know?

I unbuckled his buckle like every other buckle I had ever seen. I unzipped his zipper like every other zipper I had ever seen. As he began to help me find the fold by shimmying out of the J. Crew boxers I’ve seen on various men across the good ole US of A, he laid his head back against his pillow and said something extremely foul that I have blocked out of my mind to this day. Up it sprung, into the air just millimeters from my face, a terrifying Jack-In-The-Box wearing a hooded sweatshirt. My first uncircumcised penis in all its wrinkly glory was just staring at me, like a turtle head coming out of its shell for the first time in its life.

So as you may have ventured from the title of this column, I screamed. Or maybe shrieked? I definitely wailed. It was a routine blowjob with a guy I had already sex’d up a dozen times before, where the hell did this curveball come from?! How did I not know this before now? OH MY GOD I JUST SCREAMED WHEN I SAW HIS PENIS.

Luckily, your girl is a quick thinker. In order to not embarrass the guy completely and lose out spending the night, I kept the scream going but turned that bad boy into a scream of sexual delight. Or at least, I attempted to. It came out a little something like this.

Oscar immediately shot up (his head, thank god) (like his HEAD head, thank double god), looked down at me, and asked what was wrong. I was dumbfounded. At a loss for words. Completely uncomfortable. I was so mortified my face had practically gone numb. So what did I come up with in response before getting kicked out? The worst god damn response in the world, I suppose.

“No no everything fine it’s just that, um…I’m not Jewish, either?”

Needless to say, Oscar and I are no more. Sometimes I run into him at Starbucks and get a little dizzy knowing his anteater of a peener is asleep in its flaccid cocoon. Try looking someone in the eye with that knowledge running through your brain.

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Topanga is a contributing writer for Post Grad Problems. Lover of red wine, mediocre gossip, and Corey's whipped ass.

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