7 of the Most Awkward Sex Moments I've Experienced

american-pie-the-pie-sex-full-disclosure-awkward-eric-barry Of course we know that sex can be a beautiful expression of love, accompanied by exploding fireworks, blooming flowers, and Paula Cole songs. But every so often the needle on that Paula Cole record jumps, and before you know it you're listening to an awkward, confusing, and at times frightening carol being led by Beyonce's board feed.

Below are some of my own less than flattering sexual encounters. Suffice it to say this is not a comprehensive list, and I assure you there will be future ones.

7. Falling Asleep

Look ladies, good sex is a lot of work, okay? I know a disappointing number of women who think that their contribution to good sex is laying there and "letting it happen to them". The fact of the matter is the best sex happens when both parties put in equal amounts of effort.

And when one partner is overtaxed, sometimes that partner is going to have to take a rest, you know, inside their other partner.

So maybe I was a little too drunk and passed out. But whatever energy she conserved from her lackluster sexual performance was certainly made up for when she had to bench press my slumbering self off her, and I'm sure it gave her a compelling reason to make sure she kept her partner's interest next time.

So really, I feel like the whole thing was a pretty romantic gesture on my part.

6. Fake Phone Number

There's the old stereotype of the guy who sleeps with a woman, and then after the fact loses interest in staying in touch with her. That's almost never the case with me. Once we've shared bodily fluids, I feel like sharing a cup of coffee is a nice way to say "Hey, we can be normal about this" even if we don't intend to continue the romantic aspect of our relationship.

After a night of (what I thought was) really great sex with a girl I had met at a bar, we decided to stay in bed and cuddle. We talked about each other's families, she shared with me how she was feeling directionless in life, and we both agreed we'd like to see each other again. After kissing at the my doorway, I asked for phone number. She recited it to me as meticulously as I took it down.

When I went to text her about what a great time I had, I received an error message back that the number was in fact invalid. If someone has a horrible time, I understand not wanting to see that person again, but I think there are more honest and mature ways to go about doing that. Ways that would hopefully prevent that situation from happening again.

5. Crying & Screaming


I cry every time I watch the Mama's Family intro. So I guess sex isn't the most outlandish emotional trigger someone could have. But there is a moment when it's happening when the thought runs through your head, "Am I doing something evil right now?"

To be fair, the first time it happened I was warned prior to coitus. "When I come, I start to hyperventilate, and I start to tear up, and then I just start sobbing. I think it has to do with when my little brother died." Man, I made that girl un-repress her memories all night. We actually ended up dating for a few months, which is when I learned that in addition to crying, she liked to scream bloody murder every time we had sex. I love a woman who likes to get vocal, but I had to put cottonballs in my ears, in part to block the noise, and in part to soak up the blood. Like, literally to the point of causing my eardrums to hurt. But it did make for some of the more fun times I've had to talk to the cops.

4. This is Awkward

Being vocal in bed doesn't come easily to me, but every now and then I like to play Morgan Freeman and narrate the gory details.

So using the word "fuck" in the context of well... you know, hardly seems worthy of registering a blip on the kink radar. Which is why I was confused when one time after a couple of mid-intercourse "fuck yeahs", the girl stopped me to ask if I was okay.

"Yes?" I responded. "Why?" "Well you keep saying fuck. I thought you were angry."

Any chance of that being played off as a cute misunderstanding disappeared when seconds after we had finished she declared "Well that's the most awkward sex I've ever had."

3. I Hate Men

While we weren't technically having sex, having an Irish lesbian named "Six" tell you that you're the first man she's been attracted to as she straddles on top of you, just before she begins to choke you while shouting "I hate men!" is certainly a much more hands-on approach to Gender Studies than I ever received at Berkeley.

This actually took place while I was performing at the 2005 Edinburgh Fringe Festival. Six and I decided to stage our encounter, using raw meat puppets as representations of our vulnerability, set to the African rumba beat from a Casio keyboard. Our performance took home the coveted Fringe First.

2. Rape

It still feels weird for me to say I was raped, but maybe that's part of the everlasting awkwardness of the whole thing. "WHY'S THIS WHOLE RAPE THING GOTTA BE ALL COMPLICATED??"

1. Getting Stiffed as an Escort by a Kid with Cerebral Palsy

There are few times I truly ever felt shame, or dirty about being an escort. In fact, just one time.

That time is when a fellow UC Berkeley student named Alex solicited my services via Craigslist. Alex mentioned in his reply to my ad that he had cerebral palsy, so I wasn't entirely sure what to expect from our appointment, but I figured a nice palsy HJ would at least keep things exciting.

I was a bit caught off guard when I arrived at Alex's home. It was quite large - three stories, which was about two too many for a kid with CP. As it turned out, the home I arrived at was in fact the home of his mother. I don't know who that mother thought I was ("Your son and I on the fencing team together"), but she directed me down to Alex's room as if she'd seen this dozens of times. The "World's Coolest Mom" mug she was drinking from suddenly took on a whole new layer.

When I entered Alex's room, he was laying on bed, watching some shitty movie I can't remember.When he asked if I'd prefer a different movie, I said yes, at which point he put on an even worse one.

There was a solid 15 minutes there when I thought, 'Great. This kid just wants companionship. There won't be any sex involved. Poor guy. He just needed a friend."

Then I heard his garbled words, each utterance a struggle to get out. "So you wanna suck it?"


And this was the first time I learned what smegma was.

Thankfully I had plenty of flavored condoms on me, and Alex was a quick shot. But he wasn't going to let me get out of there without servicing me in return.

I know a lot of able-bodied disabled people. People who type long, grammatically flawless PhD dissertations using nothing more than a cranial halo mechanism. People who feed themselves with their feet.

Alex was not an able-bodied disabled person, and watching him struggle to do his best while failing miserably at avoiding the contact of his teeth only added more shame and complication to the situation. 'I can't turn this guy down, right? That would just be smearing my able-bodied privilege right in his face, along with my penis, right?' Dammit, Berkeley.

After that garbage disposal of a blowjob, I couldn't get out of there fast enough. All that was left was the payment. The few hundred dollars that I desperately needed, that would make this whole situation seem worth it, somehow, in the aftermath.

But then Alex told me he didn't have any money. He told me he thought that this whole engagement had occurred for free. He told me that maybe he could pay me next time. But there was no feasible way I would ever let there be a next time. Ashamed, infuriated, confused, and hurt, I left.

The next I saw Alex he was at (the now closed) Blake's on Telegraph. It doesn't take long to recognize someone, especially when they're in a mechanical wheelchair and they nearly chewed your dick off. I wanted to avoid him at all costs, but I couldn't help but notice when after a few seconds of staring at me, he began laughing - cackling even, head titled back maniacally with his eyes locked on me, like some kind of bad supervillian stereotype. He knew what he had done, he had remembered, and he loved it.

So now I blog for therapy. http://youtu.be/r4W0t_fWJoE?t=40s

------- Have your own tales of awkward sex? Leave us a voicemail at (415) 779-6855 and we'll play it on the podcast.