Would You Keep a Sex Diary for a Week? Wow, is 'The Sex Diaries' Juicy

The Outdoorsy Guy Feeling the 7-Month Itch

31, Portland, Oregon


11:38 a.m.: I am at work and haven’t been thinking about relationships or sex today. Only about data.

11:41 a.m.: Yikes. Thinking about the fantastic little clip of lesbian porn I watched on the Internet last night. It reminded me how much I like to give cunnilingus, and at the same time, I’m reminded of how I don’t really like to do that with Alyssa.

12:12 p.m.: Just got a random Gchat from Lauren, an older coworker I dated briefly. She is crazy, but I loved going down on her.

3:46 p.m.: Just got back from a walk with Lauren. Our dating ended because she just wasn’t that into it. I can’t say exactly why, but it had to do with her having different priorities.

4:00 p.m.: Not excited about hanging out with Alyssa tonight. This feeling is furthered when she says that all she wants to do tonight is hang out with me. We have been dating for seven months, and she moved from another state to be with me.

6:11 p.m.: Still at work, an hour later than I need to be, working and listening to music. Friday night. Lamesville.

11:00 p.m.: Had a frustrating evening with Alyssa and her roommates, hanging out and eating dinner. Alyssa and I watched a silly movie and are now going to bed. Friendly, not intimate.


12:18 p.m.: Just got home from Alyssa’s house. Talked a little about how I wish I felt more free and open in our relationship. She didn’t say much. Most mornings she has sex on her mind, and doesn’t really listen to me. (Ha.) I was sort of in the mood, so we had sex and it was fun. Mellow breakfast. Alyssa is great most of the time.

4:22 p.m.: I think of myself as being bad at relationships, like there is something I don’t get. My primary issue now is my desire to have multiple casual partners, as opposed to one committed, closed relationship. Why? Because I am not fulfilled sexually in the relationship I’m in.

6:13 p.m.: Alyssa is very patient and forgiving, and has never broken up with a boy. She is a peacekeeper. Were it not for me, I imagine this relationship could last forever. It seems like I need to get over some hurdle if I am to avoid tearing this relationship down.

9:42 p.m.: On the topic of sex and other women, tonight I am pleasantly annoyed by all the uninteresting girls out with us, and content and glad to have Alyssa.

9:45 p.m.: I have an inability to date or stay in a relationship with women who are not smart, or those who cannot at least act intelligent and articulate most of the time. This is a fantastic juxtaposition to my vanity and desire for attractive women. These two things make me very picky. And an asshole.

12:30 a.m.: Fun night. Got a little drunk with friends, including Alyssa, and went to a reggae show. Broke into new territory with her. We smoked pot together. She never smokes and doesn’t like it when I do. But we talked about it and she demonstrated an amazing ability to push her boundaries. We had some good talks, were silly.

1:00 a.m.: Fun late-night bike ride home and some pretty great sex before bed.


9:15 a.m.: Woke up enjoying Alyssa’s warm body and snuggles.

12:21 p.m.: She just went home. This relationship is so unique. Alyssa is so unique. It’s certainly new territory, and I forget how special our bond is. Sometimes I feel like our relationship right now is not necessarily what I want, but it might be exactly what I need. I’m never quite sure what I need.

12:30 p.m.: I should say that I am happy that I am “in a relationship,” as opposed to being “not in a relationship.” However, I would prefer my status to be: in a relationship.*

[footnote]*My relationship is very free and open and fun and loose.

It seems like there’s no asterisk option. If after the next several years I still haven’t learned how to relax and accept an intimate relationship for what it is, I imagine I will be a curmudgeonly old bastard, all alone.

1:02 p.m.: Brief thoughts pertaining to sex with strangers: Never tried because it has always seemed wrong. Immoral. But I am growing more and more keen on the idea of going to Craigslist’s Casual Encounters and meeting up with a complete stranger and acting out some sexual fantasy. I still feel like that kind of thing is not within the realm of healthy, normal people. And then there is the issue of going behind my girlfriend’s back.

10:44 p.m.: Spent the evening with roommates. Two short conversations with Alyssa on the phone, of no significance. Just checking in, talking about plans. No pressure to sleep together tonight. Feels nice.

10:47 p.m.: I’m on the Internet and I will probably look at a little bit of porn. Or maybe I’ll be good and just pick up a book and read til I fall asleep.


9:51 a.m.: Reflecting on my relationship with Lauren, then recalling several years back with Gillian. I have a fondness for these relationships that is odd, and I think what they have in common is that: 1) I liked who I was in the relationship, and 2) I didn’t see the relationship really going anywhere, and neither did they necessarily. When there is pressure to “make this work,” I seem to fall apart, I get grumpy, I don’t really like myself as much.

11:06 a.m.: Work. I feel like I have been wandering aimlessly, doing very little in my life, not going anywhere. I realize that most people probably feel this way, like they should be doing something differently.

12:00 a.m.: Alyssa is sleeping over, and there is zero intimacy. She got a little upset and almost left because she wanted to have sex, and I was tired and not in the mood. I don’t know what it is, but I am an incredibly sensual person who thinks about sex all the time, yet when it comes to having sex with my partner, I’m just not that excited.


10:26 a.m.: I really like a skinny waist, with round breasts in my face. Alyssa is boxy, narrow hips, thick torso, broad shoulders.

11:17 a.m.: It’s gotta be fairly common for people to just want to bone down, right? Maybe that new girl with that big ol’ booty in my office is one of those.

11:19 a.m.: I hold honesty as the highest virtue. And yet today I am considering going behind Alyssa’s back. Why can’t I be honest with her? This is the very first relationship where an affair is even remotely possible. In all previous relationships, my faithfulness was never even close to being an issue.

4:58 p.m.: Just got back from lunch with older ex-girlfriend, Gillian. We often meet up for coffee and chat. We have become pretty good friends since our breakup two years ago. Alyssa does not like that we are still friends.

5:22 p.m.: I will always love Gillian. That relationship was a landmark. It was the only time I’ve really had my heart broken, like crushed. It’s the only relationship where I was all-in, from the beginning. It was what I thought I always wanted, dream girl stuff. I value growth, and there was tons in that relationship.

6:58 p.m.: Alyssa wants me to come over to her house and give her a kiss. That doesn’t really float my boat. I wish it could be a quick passionate fuck.

9:00 p.m.: Lied to Alyssa when she asked, “Oh, did you go out with your coworkers?” Even though we just got a bite to eat, and it was purely catching up, I know that she wouldn’t approve. I never outright lie like that, but this is the second time now, both having to do with an ex. I hate this.

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