WARNING: This post contains material of a frank and sexual nature. Reader discretion is advised.

So…I feel very conflicted. I had a sexual misadventure Monday night that was (true to form) completely unfortunate and obscenely hilarious. Even as it was happening I found myself thinking, “Wow…this is so blog-worthy.” But I just can’t bring myself to chronicle the tale. A lot of the one-liners my dude said to me were priceless, yet raunchy enough to make Andy Dick blush. But I’m pretty open about talking about my sex life, and I am sure as shit always up for asking about your sex life, so it’s only fair that I share. So I’m giving you the PG-13, edited for TV version of the story instead of the full X-rated straight to a porn store near you version. If you are related to me, work with me, or just find the idea of me having sex disturbing, allow me to nutshell it: Sex. Went bad. Left. I only date weirdos. Fin. If you’re feeling more adventurous, read on. But you have been warned.

So I went on a round of successful dates with a 22-year-old hipster musician who lives around my neighborhood. We’ll call him…Blake. Overall I feel very “meh” about him. STATS! Pros: Sarcastic, really likes me, always has a compliment and most importantly, the best hook-up I’ve ever had. Cons: When he talks, I have elaborate fantasies about duct tapping his mouth shut, cokehead, likes tranny porn and is incredibly impressed with himself. I decided a few weeks ago that the cons outweighed the pros and cut off all contact. But you have to understand that I’m a gay frat boy trapped in the body of a 22-year-old woman. I can’t waste a good hookup, but I don’t want “emotions” or “feelings” to get involved. So I decided to entertain Blake’s request to hang out, but strictly on a hook-up only basis. One more sit-down with him and I fear I’d shove a salad fork in his eye.

Monday night we decided to make a sexin’ date, so I headed over to his place for the first time. In the straight-up ghetto. But one must make sacrifices for a decent hookup, so on I bravely went. I got to his place and headed down to his “apartment” in the basement, which he turned into his personal music studio. I was forced to get the full tour of his studio (including a long-winded explanation about the difference between Japanese symbols and American-made symbols…) while his friend burned some of his porn from him. Thanks asshole. Can’t you use X-tube like a normal person? After porny friend left, it was time to hop on the good foot and do the bad thing.

HILARIOUS THINGS HAVE BEEN EDITED AT THIS POINT BECAUSE THEY MAKE ME FEEL DIRTY WHICH IS SAYING SOMETHING. Let’s skip foreplay and cut directly to sex. I brought a condom with me because the thought of breeding with the world’s most boring cokehead is enough to become celibate and get thee to a nunnery. However, Blake insisted he had is own special condom he was going to use. Whatever, get to it, thought I. Two thrusts in and the flag went from full glory to folded neatly and put back on the shelf. Not happy. Blake insisted that this had NEVER happened to him before and it was definitely NOT me. Could I give him a little head to get things going again? Why not, we all need a helping hand (or mouth as it were) every now and then. Plus I had never given a blowjob to a dude wearing a condom before and frankly, I was curious. I actually didn’t really care at this point because I don’t really mind giving head and his condom totally tasted like English Breakfast tea. So now I wanted sex and a scone.

Back in position we went and things were going fine. Suddenly, Blake starts screaming and falls to the floor in pain. He starts hitting his now yet again flaccid dick over and over again and then ran to the bathroom. A few seconds later he came out looking embarrassed and in pain. Blake explained that he sometimes has a problem with premature ejaculation (STEEEEEEERICK ONE!) and wanted to impress me, so he bought Durex extended pleasure condoms lined with Benzocaine. Benzocaine. Benzocaine is a local anesthetic and fish tranquilizer. Why in the sweet name of Jesus would you want to put that on your penis? So the poor kid can’t feel his dick at all and then proceeds to have an allergic reaction to the Benzocaine causing him to lose it. I’m sure that was very scary, but I could NOT stop laughing. There I was, in the basement of a house in the ghetto wrapped in a sheet laughing my ass off while my date was in the bathroom screaming and running his dick under the faucet. This is my life.

Five minutes later he came out and apologized for his current inability to perform. He proposed that he explain all of his studio machinery to me while he waited for the feeling to come back to his nether regions. I explained that I think I should hit the old dusty trail. “Wait! I’ve got some killer pot!”…Damn him…I can’t resist that! So there I sat high as a kite as he manically raced around his studio explaining the mechanics of his amps and microphones and how his computer worked in conjunction with each cord and blah blah blah... Now, I don’t mean to be heartless but…DO YOU KNOW HOW MUCH OF MY LIFE IS SPENT BEING BORED ASSHOLE? I spend 8 hours a day, 5 days a week sitting in a cubicle trying not to fall asleep and thinking of new ways I can entertain myself without getting fired. I never thought I could be more bored then I am at work, but congratulations Blake, you proved me wrong (STEEEEEEERICK TWO!)

At least the situation really couldn’t have gotten worse. Oh wait, yes it could. Suddenly we heard a door slam upstairs. “Oh shit…get your clothes on! Get dressed! My dads home!!!” Um. What? That’s right kiddies! His basement apartment was in the home of his drunken and abusive father’s house. How lovely! Blake raced around the room picking up condom wrappers and spraying air freshener to hide the pot smell like a fucking 16 year old. It was at this point that I couldn’t find my pants. Why? Because Blake had hidden them under his bed. Why? I don’t fucking know, why did he think it was a good idea to put a fish tranquilizer on his dick? I got my pants on, grabbed my bag and was thinking of how I was going to gracefully leave when he said, “Well, I guess the odds of us having sex are out tonight. Why don’t we just sit and talk about more?” STEEEEEEERICK THREE! I’M OUT!

Sha la la!


Anonymous said...

"I spend 8 hours a day, 5 days a week sitting in a cubicle trying not to fall asleep and thinking of new ways I can entertain myself without getting fired."
*can't breathe from the laughter*

They can't even fire me at my job, so all the challenge is taken away. And I've gradually whittled it to like...4.5 days by skimming hours off the days my boss isn't in.

That's right, making less than minimum wage has slowly but surely worn my work ethic (what little I had) down to a tiny almost invisible nub.

Anonymous said...

I know right? I just wish something glamorous/dangerous and lucritive would happen to me like Tom Cruise in "The Firm"

That movie made me excited for corporate America in a really twisted way.


tdot said...

I fully sympathize. I've had a guy legitimately try to convince me to use notebook paper as a makeshift condom. Not going into details, sex didn't happen.

C said...

New reader, but felt I had to share my experience with benzocaine lined condoms.

This was actually my first time, and they guy, clearly nervous about popping a cherry, used the roofied condoms to ensure that I enjoyed myself for as long and frequently as possible.

As is with most guys of normal dick capacity, two thrusts in he went soft. we were both embarassed, so I decided to peel off the condom and go down on him. I started off awkwardly, as any first timer would, but my thoughts went from "Is this how I do it?" to "OH MAH GAWD I CAN'T FEEL MY MOUTH!"

So here we are, he can't feel his manhood and is freaking out about that, I'm opening and closing my mouth like a terrified guppie, wondering if I'm allergic to dick, and feeling terrible that I can't even get a guy hard when I'm naked and he's in my mouth.

He made it up to me, but my first time was one for the record books.

Anonymous said...

I had an experience with a 31-year-old guy who invited me to his "apartment" for "dinner."

Dinner = Easy Mac, dessert of gummy bears.

Apartment = Awkward dorm-style room where he shared a bathroom (located outside the apartment) with four rent-paying strangers and had no kitchen. Complete with a floor-to-ceiling cat climbing post and two cats. Wall decorations included the cover inserts from video game cases.

Mayyyybe this guy had unrivaled sexual prowess, but can't say I stuck around to find out.

Anonymous said...

Mal ehrlich, wie viele Dates haben Sie ueber das Jahr verteilt, wenn Sie ohne Netz nach dem richtigen Partner fischen? Zwei, vielleicht drei? Im Internet haben Sie einfach die größte Auswahl suchender Singles - und damit große Chancen auf viele spannende Dates, von denen eines bestimmt mehr als viel versprechend ist.

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