My Sexual Encounter With Murphy’s Law

Roughly two weeks ago, I probably had some of the most awkward sex imaginable; nonetheless, it was quite laughable. It went a little like this:

We were making out, as horney worked up young adults do before they really ‘get it on’, and right before we began to have sex, he pulled out a condom and his little member. Except, it wasn’t little. . .it was humongous! Well, maybe that’s a little bit of an exaggeration, let’s just say, it was bigger than average. This wasn’t the only thing that caught me off guard, he was also uncircumcised, which was new to me.

Now for the awkward part. I was trying to explain to him, like a noob, that I’ve never been with an uncircumsized penis, but he kept saying he didn’t know what I meant. Oh! I forgot to mention, his first language isn’t English, which, now that I think about it, is probably why he didn’t understand what I was saying. When I realized my point would never get across, I decided to give up and pretend like I knew what I was doing. When he handed me the condom, however, I froze. 

Uhhhh, do you put it on the same way as usual?!

I had no idea, so I told him to do it. Of course, he said he didn’t know how to and that the girls usually do it for him. I was a bit baffled. I mean, if you are a male with a penis; you should know how to wrap your own willy! Sighing, I grabbed the condom and tried my best to put it on him. I just couldn’t do it, and not because I’m incompetent, but because he was just too darn big! This is when I confronted him about getting bigger sized condoms.

By now, the heated mood began to die down, but we both still wanted to have sex, thus, we devised a plan: he was to hold one side of the condom and I the other as we both attempt to pull it open whole easeing it onto his penis. This is a pretty risky plan, considering one of our fingers could slip, ultimately snapping the elastic band at the base of the condom closed onto his very sensitive male organ. After about five tries and three condoms, we succeeded. At this point, however, we were no longer worked up, but it took so much effort to get the damn condom on that we decided to have sex anyway, which was an obstacle in itself considering how big he was compared to me.

Overall, it was one of the more interesting sex situations I have experience, and I have a few things to take away from it (this goes for guys and girls): 

1. If you are going to carry condoms, make sure you have both regular and large; if you are a guy, know your size!
2. Know how to properly put a condom on . . .
3. Read up on how to deal with uncircumcised penises

Also, here’s a someecard that perfectly depicts this situation:

Toodles! 

MW

• awkward
• sex