Dear Funny Bunny: 1st Time Anal
I'm a pretty vanilla guy, so I never really thought I'd be penning one of these letters.
I'm used to perfunctory missionary sex that does its job for both partners. If it doesn't, then sure, I'll go down on her until she's finished — I'm not a monster — but that's about as freaky as it gets.
But before you throw this letter in the trash with all the ones you reject from Altar Boys or Rudy Giuliani, understand that, like every other easy-to-mistake-for-a-Mormon guy out there, I have one weakness that guarantees poorly-thought-out sexual adventures…
Whether it's a birthday, anniversary, Christmas, Easter, Hanukkah, Kwanza, or Labor Day… I'm down for something new.
And for this particular bout of adventurousness, it was the first sexiversary for my girlfriend and I.
I'd long suspected my sexy-librarian-meets-big-titty-goth girlfriend was freakier than me — I mean, she wears a choker for fuck's sake, that's basically just a dicksucking blackbelt — but this surprised me a little.
We decided to celebrate a year of slightly formal, yet satisfying, business sex with a gift to each other: we could each add one ornament to the sexual Christmas tree — one freaky thing the other couldn't object to.
I didn't want to overplay my hand and pick a threesome — that seemed too risky.
So, I went with something tamer and stammered out that perhaps, maybe, if she was cool with it and no pressure at all, but, like, possibly, she could really ramp up the dirty talk and go for broke — say some shit that would make my grandma disown me.
"Is that it?" She asked. "I thought you'd go for a threesome. Sure, I can do that."
"Awesome. W-what did you want?" I asked sheepishly.
"I want you to fuck me in the ass deeper than Nicolas Cage hunting for treasure under the White House."
Now, neither of us had ever had anal, so I'll admit I was somewhat taken aback by this. But whatever, it seemed fun.
We start going at it and, almost immediately, she starts cursing like a Scottish sailor. She's screaming colorful profanities in sequences I'm reasonably sure are designed to wake up some long-dormant Lovecraftian monster.
I'll admit, when I asked for dirty talk, I didn't expect gems like "Alex titty-fucking Trebek's burning merkin!"
But still, it was working for me and had me drilling her like the US searching for oil in the Middle East. Only, it wasn't for her.
I know this because all of a sudden, she started yelling, "Stop, this isn't working for me!"
It turns out it wasn't dirty talk at all. It was really just the caterwauling sounds of a be-hymen being broken.
"This isn't working… it hurts too much," she sighed. "Wait here and stay hard until I get back."
She draped herself in a trench coat that made her look like a sex-crazed '90s school shooter and glided out the door to my apartment.
I was a little confused and worried she'd never want to have sex again. Still, she told me to stay hard, so I was lying in bed alone slapping my dick like a suspect in a dirty cop drama.
When she came back 20 minutes later to me screaming, "Who ordered the hit you low-down sonuvabitch?!" as I slapped my cock, she had a smile on her face.
She opened her trench coat, and so many toys fell out it looked like Inspector Gadget got hit by a claymore.
She gathered them and hopped on the bed.
Anal trainers, anal beads, anal plugs, and enough lube to drown a whale — pretty soon, we were filling the back door like it was Mary Poplins' handbag.
And everything went smoothly after that.
Sure, the dirty talk was a little tamer this time, but I didn't mind…
We were both happy.
But next time, I'm gonna ask for that threesome...