What It's Like To Lose Your Virginity To A Woman On Her Period

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If you're to believe everything American Pie told you then, yes, losing your virginity is a rite of passage in high school. Like many of the young men of my generation, the mid-2000's were a sexual awakening of sorts (thanks, Internet porn.)

Thanks to Google, we became adept at sourcing literally anything. Any guy in his mid-to-late twenties will bashfully admit that we all began to imagine losing our virginities in grand fashion. Teacher on the desk? Check. The MILF next door? Absolutely. My Friend's hot mom? Jackpot.

Porn, unfortunately, did a bang-up job of absolutely warping our sexual expectations. We all felt entitled to a statuesque blonde with silicone everything.

I was one of those kids … until, of course, I lost my virginity to, well, an overweight woman.

Now, now ... pipe down "fat shaming" activists. It was hilarious, fun, and disgusting for reasons completely unrelated to weight. 

I'll set the scene: Fall 2005, our Junior Varsity Homecoming Game. (We won!) I was the starting middle linebacker and had a really huge game. High fives from my bros, hugs from my parents, cheers from the girls in the stands, the works. One of my buddies threw the weekly post game party at his home. We saddled up with 30-racks of Keystone, beer pong balls, bottles of jack, beer-bongs, bags of weed and backwards baseball caps and traipsed to Funville, USA. 

Don’t laugh, but we would play the National Anthem before every binge-drinking party. Why? Well, why not? During the national anthem is when she caught my eye … I wondered how hot she might be if she didn’t have two chins. I wouldn't have to wait long to find out.

We did Jack Daniels in the beer-bong that night. Between games of flip cup and Kings, I struck up a conversation with "Amy" (the lady who de-flowered me). If I'm being honest, I have no idea what we discussed. I was probably cross-eyed and that’s okay.

After a bit of chit-chat, Amy continuously (and forcefully) grabbed my unmentionables until enough blood was pumped into the region to constitute what you might call a wooden battleship.

One thing I would not have issues with on this particular evening would be performance. This, along with my whip-smart technical knowledge of all things porn, was ammunition enough to open fire. We escaped into the nearest bathroom.

I should mention, there wasn't any mood lighting in this bathroom. It was a lights-on or lights-off kind of situation. The adrenaline rush was enough to sober me up a little – and for this, I was thankful. I wanted to have enough vision to apply what I learned from porn. She started to perform fellatio … and, yes, the rumors are true. Larger girls are better. 

I stammered drunkenly "Ok, wanna have sex?"

With one eye open, she happily replies "Sure."

What happened next was tough.

With the removal of her shirt, my porno fantasies were shattered. There was nothing statuesque here. I honestly could not tell where her stomach began and her breasts ended. It all just kind of, well, mushed together.

Similar to climbing Mount Everest, this was the type of thing that you had to finish when you got to a certain point. It was only right to finish the job. So, I stuck it in. Less than two minutes later, I pulled out.

I felt like I should be a gentleman and, you know, finish her off. So I got to applying what porno taught me best … oral sex. About twelve to fifteen seconds into my oral assault, I caught a glimpse of my hand and nearly broke my own neck.

Covered in blood.

I shot up and drunkenly glared into the mirror.

I resembled more a Lion feasting on a gazelle than a pimply former virgin.

Gazing up at me, Amy chuckled.

"Silly! I ha-" She hiccuped. "- I have my period!"

Was I mortified?  No ... terrified. Confused. I was on a roller coaster on emotions that only seemed to have staggering plummets and pitfalls.

In this moment, I had resigned myself to the bleak fact that losing my virginity was a definitive failure. But there's silver lining (there always is, kids.) Truth be told, Amy and I spent the next hour or so in the bathroom laughing, making out, and instituting dozens of inside jokes that we still crack to this day.

Through the whole process, Amy was free-spirited and willing. Also, despite what social dogma dictates ... she didn't look that bad naked. It reminds me of that famous lamentation about "pot bellies" from Pulp Fiction, where Bruce Willis has just returned to the motel where he and his wife are camping out.

Indeed, it's a shame that we seldom find what's pleasing to the eye and pleasing to the touch to be one in the same.

This girl was luxurious. There really is nothing quite like the embrace of a lady who has the equipment to really wrap herself around you and totally engulf you. Warm, inviting, and pretty hilarious. The stereotype about larger ladies having great personalities? It's true — and they should embrace it. I can only imagine in horror if I had the hottest girl in school in that same oops-I-came-too-fast situation; I probably would have been a laughingstock by the following Tuesday. 

I'm fortunate to have learned early on that our stigmas about physical attraction are moot. I was (and continue to be) wildly attracted to Amy, despite the incident that capped the occasion. 

She wasn't the last heavier girl I've had the pleasure of bedding. Sometimes, heavier girls bang you.

If you learn nothing else from me, know this. Promiscuous sex is awesome because of variety. If she's got dumps like a truck, get in there and operate.