Tuesday, January 6, 2009

Laura

Laura came to New York from New Hampshire just for this. She's clearly had a crush on me for awhile, since I met her while visiting friends at Dartmouth. Still, she's not my type. Other friends of mine think she's totally cute, but she's bookish in a way that doesn't do it for me.

But I put her on my list of people to email and she said yes.

I find it weird that once this experiment was set up, I was so much more willing to sleep with people I normally would not have. It just seems so relaxed, more about curiousity and less about raw sexual attraction and compatibility.

We went out for mexican food, then went back to my place. We were still acting friendly, though Laura is usually a little flirty with me. This time she wasn't really. So after some talking, I said, "Well, let's get to this."

She said to me, "Okay, but you have to start it."

I kissed her, she kissed back, timidly at first but gradually harder. Kissing continued for awhile until I took off her shirt. She kept kissing, no more clothes were removed. Eventually I removed the rest of her clothes until she was naked, but I was still fully clothed. So I began pleasuring her, which is the first time this has really come up. The past few days have all involved just straight up sex. Eventually, she pulled me up and went for my belt. The sex that took place then ended rather quickly, and she held on to my tightly.

"How was it?" she asked.
I told her it was good, but I felt a little embarassed that it had ended so quickly.

Both she and Katy were lesser-endowed women, which made Susan seem so much more busty by comparison.

I got dressed and poured us glasses of water. She spent the night, but nothing more romantic took place even though we shared a bed. We hugged goodbye and I headed to the office as if the whole thing didn't just happen.

Sunday, January 4, 2009

Katy

I got a call from Susan this morning asking if she could help out at all with my girl today. I asked her what she meant, and she said like videotaping or cleaning up. I liked the idea of having an assistant, so I said yes.

Katy is a girl I had been with a few times a little over a year ago before she took a job in Texas. She has a normal frame, not skinny but not fat, and dresses very conservatively. She's back in New York and we just never got around to meeting up. She came over after work, but Susan wasn't there yet.

I told her we should wait for Susan as I got us some beer. Katy was curious if I wanted a threesome, which I didn't really want. I guess it wouldn't violate my rules, but I was so early in the year that I didn't want to overwhelm myself. A few minutes later, I realized I had been offered a threesome, which is rare/cool.

On one hand, this experiment has made women okay with having sex, maybe because they're not afraid I'll get the wrong idea or have to deal with emotional consequences. Or maybe they figure if other women are doing it with me, it's not that bad.

Susan showed up and was very much about getting down to business. She ended up being like a movie director. "Start kissing" "Take off her bra" etc. I was surprised by the degree to which Katy complied with all of this, but she seemed amused.

I was a little embarassed to be doing this in front of Susan, but I guess this was all stuff Susan's seen before. Katy was better at this than she had been originally, less shy and, well, less drunk. As it was going on, I definitely looked up at Susan a few times, which I'm sure Katy noticed. Susan was laughing, though not quite out loud. It was like I was her kid and she was watching me at the pageant. Right after it was over, she clapped.

It was okay and I was too relaxed afterwards to get mad at Susan, who sat on my chair as I held Katy in my arms for a few minutes afterwards. Then Katy and I got dressed, Katy left (we kissed goodbye!) and then Susan and I talked about how it went. She said it was hot, which it was a little, even if it wasn't acrobatic or anything (it was just girl on top for awhile).

Anyway, Susan talked about the girl I have scheduled for tomorrow (Laura), complained that she couldn't make it tomorrow, and then left. We hugged.

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.

Friday, January 2, 2009

Susan

Susan is a friend of mine from college. She has a heavier build than girls I normally go for, but she's fun and adventurous and we're good friends. I wouldn't really pursue her romantically, but I'll admit I did kind of look forward to this.

Despite more buxom build, she's very energetic, so I expected this to be very passionate. We've also been friends a long time, so maybe that would make her more eager to be herself during the act. Still, since we've never been sexual before with each other, I expected a little bit of shyness.

We met up for dinner at my place. Part of me was afraid. If she didn't show up (flaked, or felt sick or something) then maybe this whole thing would just fall apart and my life would go back to normal. But the buzzer went off, I opened the door and there she was. This was happening.

We ordered Chinese. We talked about how weird this was going to be. When the food came, I just said, "Let's do this first." Mostly I was embarassed about sex on a stomach full of Chinese food plus it would be kind of cool to eat Chinese food right after sex.

So right after saying that she just laughed and I patted the spot on the couch next to me. I touched her face, which felt weird since I'm not intensely attracted to her sexually. But we had agreed on doing this, and there was something exciting about doing this and knowing there wouldn't really be negative consequences.

Since she let me touch her face, I went in for the kiss. She kissed surprisingly well. Not long thereafter, she pushed herself away and pulled off her clothes. My first thought was that her body wasn't perfect, but her skin was very soft. Not long after we had started, we both kind of looked at ourselves like "Well, this is weird." It did feel pretty great, though. She did a great job.

I started on top, then she took over, then we tried a "going-from-behind" situation. After it ended, we lay in each other's arms for a minute. Then I suggested Chinese food and we had a great naked meal.

By the end of the meal, though we were naked, I felt as if the sex hadn't even happened. Though I did have this interesting relaxed feeling.

I'm curious to see how this affects our friendship, since it was more fun than I had expected. Still, once clothes went back on, we were more or less back to normal. Not even a kiss goodnight, and definitely not staying the night.

Thursday, January 1, 2009

Christine

So today was the last time I was intimate with my girlfriend, Christine. We both new that at some point we'd have to part ways, and this year experiment of mine provided a timeline for that. I'm grateful to her for being a part of this.

Our encounter wasn't really out of the ordinary. It was this morning, after waking up after celebrating New Years together. I'd estimate it was about 15 minutes or so, nothing fancy. We kissed for awhile afterwards and I was genuinely sad that this would be the last time.

We had dinner with my family and after I walked her to the subway, we hugged tightly and she wished me luck.

Wednesday, December 31, 2008

New Years Eve: We're Go For Launch!

Hey everyone! Happy Almost 2009!

So we're all set. I have 15 women lined up. What I've done is assigned 10 of them a day and the other 5 are "backup people" in case someone is unavailable or something. This was complicated to arrange with schedules and menstruation cycles. But I'm excited. Some of these people I've never slept with before, some I have and am curious to see how they are again with the passage of time. The first one, however, will be bittersweet as I will explain tomorrow.

I've decided not to do anything sexual today, as I figure I will soon need the rest.

Monday, December 29, 2008

Predictions

1) Sex will become monotonous

So I've had a few relationships before and I know that over time, sex can become monotonous. It loses the urgency it has when it's rare. However, that sex has been with the same person over and over. So there's a chance the novelty of each new person will make it interesting. Still, I foresee it getting boring.

2) Performances will increase in duration

I figure it will just take more to excite me

3) I'll become sad that I'm unable to have a relationship or an actual date for a year

And that's assuming anyone ever wants to date me again! But, alas, this is science.

4) I'll become much, much more relaxed