Cindy

Cindy is a friend of a friend of mine who heard about this idea from our mutual friend and indicated interest. We had met once and she was pretty cute, so I was excited by her signing up. We spoke over gchat, but hadn't really ever spoken in real life.

We set up a meeting at her place. I came by right after work. She answered the door in sweatclothes and glasses. Her hair was up and she wasn't wearing makeup. Honestly, the look was a little attractive, but she didn't look as cute as she did when we had first met.

Like with Susan, there was a little bit of awkward chit-chat. Her roommate was home, too, which was weird. So we talked about our mutual friend and about the project. She began mocking it, which made me think she wasn't going to go through with it. Luckily, I had my standby ready. Or I did as of lunchtime.

However, as it got to about 8 and we had been talking for almost 40 minutes, I asked her if she was ready. She said "sure" and, I'll admit, I got excited. Over the course of our talk, I was able to pay closer attention to Cindy, and she definitely had something about her I wouldn't have minded having sex with.

She walked over to the door and shut it. Then she began immediately taking her clothes off. I found this odd, as I had expected her to kiss me and then clothes to come off organically, in the moment. I guess not, but then again, Susan did the same thing yesterday. This feels a little dirty, like it's prostitution or work or something.

I do the same and we begin kissing. Her kisses are tight and reluctant, like she doesn't want me getting the wrong idea, which is strange since we're naked. I try touching her and, again, she seems reluctant. I'm confused.

Eventually, after a few minutes of awkward pecks on the lips, she gets up and gets a condom. We're mostly silent during the sex, which was largely mechanical. It took awhile as I was more confused than in the mood. Eventually, I found a groove and finished. Luckily by then, Cindy had her eyes closed and a smile on her face. I presume she was imagining someone else. She was breathing deeply.

I headed off to the bathroom and then quickly got dressed. I thanked her and left. I had to keep reminding myself on the way home that we had had sex because, honestly, it just felt weird and out of place.