7 of the Most Awkward Sex Moments I’ve Experienced

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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

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This has much less to do with this article than it does the fact I found this awesome picture of myself I actually sent out to my friends after me and my last girlfriend broke up.

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.

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About Eric Barry

Eric Barry is a Chicago comedian, writer, and creator of Full Disclosure, voted "Best Sex-Positive" podcast by the Chicago Reader. He holds a B.A. in Theater & Performance Studies from UC Berkeley, and his work has been featured on Huffington Post, Cosmo, SF Chronicle, and more. He is currently working on developing a pilot based off his time in the sex work industry.

Comments

  1. That picture is epically epic in a hilarious way. Haha BURN on the wrong number. I can’t imagine a girl doing that – are you sure you copied it down right?? Or maybe you really were just that bad. 😉

    • Haha – I’m POSITIVE I copied it down right. I think she just wanted to avoid the confrontation of telling me she was just looking for a one-night stand.

      And I suspect I’ll be creating many more similar pictures throughout my romantic career.

  2. Sometimes a woman just “lays” because she is in a very physically, awkward position.

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