sex diaries

The Casually Dating Nonprofit Worker in Love With His Hookup Buddy

Once a week, Daily Intel looks behind doors left slightly ajar. This week: The Casually Dating Nonprofit Worker in Love With His Hookup Buddy: male, 25, financial district, single, gay

8:47 a.m.: Make eye contact with a cute guy who is checking me out as he steps off the 4 train … full head turn ensues. This is going to be a great day.
9:01 a.m.: My hot boss grunts his hello when I walk past his office. He is an ass, but I am usually too busy staring at his amazing body to let it bug me. He spends three hours at the gym every day and it is worth every minute!

3:45 p.m.: Get a text from my Old Man to set up dinner later this week. He is a mid-40s finance executive. We’ve been seeing each other for about three months, after being introduced by a friend of his who I also hooked up with.
3:47 p.m.: Old Man tells me he misses me, which would be great if he were fifteen years younger. We got in a stupid fight last week and I have been ignoring him because I am mature like that. My attitude toward this whole thing is that I will continue as long as it benefits me. We make plans for dinner later in the week.
11:15 p.m.: Out for drinks and get a text from my regular Hookup Buddy for tonight. We have been hooking up regularly since the summer. Great except I have started to fall for him. Hard. My last relationship ended after college, when I dated a great guy who I managed to systematically, and completely unintentionally, wreak emotional havoc on. He no longer answers my phone calls.
11:29 p.m.: Naked.
11:34 p.m.: I usually only top but lately have been enjoying switching things up a bit. His dick is big but I’ve always liked a challenge.
11:45 p.m.: He finishes and I get on top. Best. Night. Ever.
3 a.m.: Wake up and jerk each other off. Finish and fall back asleep thinking that I really wish we could make this something real. The only problem is that we really know nothing about each other, but have probably the best sexual chemistry I have ever experienced. I haven’t had the balls to bring this up either.

8:15 a.m.: Walking down Wall Street in my wrinkly clothes. I feel like I smell like sex.
3:45 p.m.: In a meeting, discussing strategy for our upcoming round of prospect visits. Manage to get myself assigned to the West Coast. I have managed to take my ability to talk to anyone and turn it into a profitable career.
7 p.m.: Go to the gym and catch myself staring at all the hot banker types.
11:45 p.m.: Get a text from a recent hookup. We met on Craigslist but ended up texting and genuinely enjoying each other’s company. I am fairly new to the city and don’t have many gay friends, so I really like hanging out with him. However, it is ridiculously cold and he lives way uptown, plus his penis is small, so I pass. Briefly consider jerking off but end up falling asleep.

8:01 a.m.: Fight with roommate over length of shower. I do the math for him: 4 people + 1 shower = Problems.
8:05 a.m.: Roommate comes into my room to apologize wearing only boxer briefs. Anger quickly subsides. The outfit was probably intentional.
7 p.m.: On treadmill next to hot guy who has the body of “the Situation” but a much hotter face. Switch treadmills. It’s hard to run with a boner.
10:45 p.m.: Aimlessly peruse Craigslist. Everyone either has a fake picture or is a crack addict. I have no idea why I think a meaningful relationship may come out of a Craigslist e-mail, but I have not been able to shake that thought lately
11:15 p.m.: Flirty text from my Old Man about dinner tomorrow night.
11:20 p.m.: How did people live before picture messaging? So hot.

7:30 p.m.: Dinner with Old Man. He tries to hold my hand on the way to dinner. No dice.
10:45 p.m.: In bed making out with Old Man. Notice missed call from my dad, who is only five years older than my date. I laugh to myself as I think about what my parents would think if they could see me now. Even I wonder what the hell I am doing, but I enjoy his company. Okay, I just enjoy feeling special. Why is that so wrong
11:45 p.m.: Old Man asks where I see our relationship going. Ugh.
Midnight: Fall asleep cuddling. This is really what I want, just not with Old Man.

4:55 p.m.: Start preparations for my birthday party tonight. I am turning 25 this week, which somehow seems extremely depressing.
10:45 p.m.: Fifth broken wine glass tells me this is going to be a fantastic night.
12:50 a.m.: Flirt with roommate’s gay friend at my party. He is nice, smart, and cute.
1:45 a.m.: Drunkenly hug new friend good-bye, promise to keep in touch. He is taking my sloppy roommate home. Wish it was me.
3:30 a.m.: In a cab with my girlfriends to after-party. Cab driver plays a Spanish techno version of “Happy Birthday.” How could this night get any better?
4:45 a.m.: Call Ex-Boyfriend and tell him that I love him. Pretty sure behavior like this is why he no longer answers my phone calls.

11:45 a.m. Wake up to find chicken nuggets and fries in my bed. Try to remember when I went to McDonald’s. Twenty-five years old, but still a hot mess. I don’t know exactly what I thought 25 would be like. By most measures I’m doing pretty well: great job that I love, great friends, but sometimes I can’t help but feel it would be a lot more fun if I had someone to share it with.
2:45 p.m. Text from the gay dude I met last night. He hopes I enjoyed my birthday. Spend far too long trying to come up with witty response.
10 p.m.Call Hookup Buddy that I love. Make plans for tomorrow night. I’m just excited to hang out with him.

7:45 a.m.: Serious morning wood. Casual stroking turns into watching porn. Nothing like a little in the morning. My life would be less complete without amateur porn.
7:55 a.m.: Jerking off in the morning really clears my head.
9:45 a.m.: My boss looks extra hot today. He comes up behind me and rubs my shoulders. Good thing I wore briefs instead of boxers today or else everyone within 100 yards would notice my raging hard-on.
11:45 a.m.: Run home on my lunch break. I love Wall Street during the day. These guys are all so aggressive and hot. Imagine them pushing me down on a bed and getting naked. Masturbate again. Wash my hands and head back to work.
9:45 p.m.: Hookup Buddy calls and tells me to bring condoms.
9:47 p.m.: Roommate gives me a pep talk and tries to convince me to tell my Hookup Buddy how I feel. I would really like to go on a date and see what happens. I feel like that would seem awfully random given our history, but I don’t want to deprive myself of the amazing sex.
10:05 p.m.: At Hookup Buddy’s house. Make out for five solid minutes before coming up for air. He pulls my hair a little while we are kissing and I have to hold on to him to keep standing.
10:45 p.m.: We start to 69 and get really into it. Poppers always spice things up a little. We finish together in one big, sloppy mess and fall asleep cuddling.

TOTALS: One act of mutual oral sex with non-reciprocated love; two acts of intercourse with two partners; one drunken call to ex-boyfriend declaring love for him; one rejected hookup offer.

The Casually Dating Nonprofit Worker in Love With His Hookup Buddy