The Gay Corporate Strategist Wondering If He Has Daddy Issues

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Gay Corporate Strategist Wondering If He Has Daddy Issues: Male, 26, Financial District, gay, single.

DAY ONE

7:30 a.m.: Wake up hungover at my parents’ house with a raging hard-on, thinking about my super-hot Crush. We hooked up a few months ago after meeting through a mutual friend (with whom I’ve also hooked up) and have been casually seeing each other since. He’s adorable, fun, interesting, and knows it. However, his crowd includes some potentially not-so-nice Gays With Reputations, and for no specific reason, I can’t shake the feeling that I don’t need to be involved in this, whatever it is. That said, as usual, I should probably just relax.

7:46 a.m.: Need to get rid of this boner so I can go work out. Throw in an old VHS of straight, hard-core eighties porn, which I generally love, but get distracted and nut in under a minute thinking about Crush and I having sex, then me coming on his face while he asks for it. This remains pure fantasy, as I’ve read too many HIV statistics to get it on with a guy I’m told rages every single night of the week. Ideally I could establish some mutual ground rules and start banging him, but he seems like a conflicted type and may be too progressive to go for my expectations. We’ll see.
4:45 p.m.: On a commuter flight back to New York, I lock eyes with the fugly flight attendant in an effort to secure the whole can of Mr. & Mrs. Ts Bloody Mary Mix. Never fails.
5:12 p.m.: Awkward: FFA just offered to buy me a drink. Politely decline, but he continues to chat me up … and just pulled out his layover schedule!? Seriously? Crosses my mind that it must especially suck to be an undesirable gay in such a superficial pond. Wonder if that thought makes me empathetic or just a dick.

DAY TWO

9 a.m.: Wake up, run, gym. The handle of bourbon that I single-handedly decimated while at home has my six-pack two-men-down, and I want it defined again. Unhealthily, have Crush in mind.
11:15 a.m.: Horny, relaxed from workout, open up Xtube and jack off. Amateur boyfriend porn is seriously hot, and I love watching guys who are really into each other go at it. You can’t replicate chemistry.
11:36 a.m.: Log on to online profile I created after recently dumping WASP, my ex and only significant relationship to date. Multiple new messages from uglies/GUDs (geographic undesirables); log off without reading them.
10:45 p.m.: Drunk with some straight friends. A bit jealous that the quality meet markets are actually useful to them; gay bars can be so gross.

DAY THREE

1:17 a.m.: Drunk text from Crush; gist is he wishes I were with him and misses me. The specific context is aggressive given our vague status, and it’s obviously a mix of sincerity/loneliness/in-character platitudes. Regardless, it’s nice and I like him, so I’m pretty stoked.
7:34 a.m.: Log on to dating website. A ton of new messages, and some guys look kind of hot/normal-ish? Am I still drunk? Resolve to respond to a few and go on first online date.
12:20 p.m.: Gchat with friend regarding mutual acquaintance H. Discuss the fact that a week or so ago a separate mutual friend got drunk and spilled that H’s father is in the Forbes 500. We decide that the ranking is not totally insignificant, and I’m allowed a slight increase in excitement about our future date, but no more than 5 percent. If there’s a second date, I must remove it from the equation.
4:10 p.m.: After a day of accomplishing nothing, pop an Adderall and head to the gym.
4:52 p.m.: Some saggy 50-plus queen stares me down, sashays over, and puts twelve-pound hexagonal weights in the 40-pound round slot directly in front of me. Mmmm, hot.
5:55 p.m.: Spot Gym Crush, head to the mat to finish early/creep from afar. I have potentially weird taste in men. He’s older, fair, thinning hair … and exactly my type. Most importantly, he is the only guy in a takes-itself-too-seriously gym who’s always smiling and laughs with his trainer.
6:04 p.m.: Wonder if I have daddy issues.
6:17 p.m.: In the locker room, hot-dad type checks me out.
6:18 p.m.: Hot Dad apologies for something and I notice his worked-out, freckled biceps. Go on.
6:20 p.m.: While chatting, he starts playing with his chub. Really? Pass.
11:05 p.m.: In bed alone, again. Wonder if I have any more Xanax.

DAY FOUR

5:30 a.m.: Wake up horny after five distinct sex dreams, one of which involved Crush as the last-minute fourth in a threesome of his friends, another of which cast WASP enthusiastically doing yard work.
6:35 a.m.: Walk past the New York Sports Club that’s notorious for sketchy steam-room activities, get kind of horny, regret not jacking off earlier. Wonder if I should try the gym sex thing. (Whack! My therapist smacking me, saying “Don’t let others define your homosexuality.”)
6:45 p.m.: This has to be the gayest yoga class on the East Coast. Unbelievable — only two guys are clean-cut enough for me. Consider reassessing standards.
8:32 p.m.: At dinner with Best NYC GF. She asks me how my love life is going. Yoga-high, I don’t want to talk about it and purposefully speak in generalizations. She mentions a guy I forgot she’s been trying to set me up with, St. Bernard’s Boy. Tell her, “Why not? Set it up.” Too mellowed out to think.

DAY FIVE

5:25 a.m.: Oddly euphoric and in the mood to go to work early. Still haven’t met my goal of actually responding to guys online. Going out later; guess if I’m horny I can just get drunk and hook up the old-fashioned way.
8:53 a.m.: Totally surprising, gut-wrenching e-mail from WASP.
12:30 p.m.: Chatting with S. Simultaneously express vague frustration about being single, bewilderment that we both consistently get feedback that we’re intimidating. But who knows: We also both get “extremely personable and gracious” when we’re definitely super-awkward.
5:30 p.m.: Work drinks = gratuitous acceleration, guaranteed bad call.
9:15 p.m.: Text from someone listed in my phone only as Australia. I’ve made more than one bad choice in this lifetime, and if it were fun, I’d probably remember. Delete.
11:01 p.m.: Message that apparently Collegiate is in town. We used to hook up and were into each other, but at the time neither of us liked giving head, and we regularly invited a third over to get the job(s) done. The best was this undergrad who, once he’d serviced us, would jerk off solo in the bathroom. It was weird. He’s a great guy, but I tell him I’m away on business.

DAY SIX

4:55 a.m.: In bed, my head and penis both throbbing. Vaguely remember convincing straight friends to go someplace mixed. Sometimes their meh attitude towards the gay thing strikes me as self-centered; I’ve thrown more (and better) vagina at them than they know how to handle.
4:56 a.m.: Definitely alone. Pleased with the vast improvement in my brown-out decision-making.
5:16 a.m.: Can’t sleep, decide to jack off. I haven’t come in days.
12:45 p.m.: Solo brunch. Tall, blond, extremely good-looking thirties suit keeps checking me out. Big G for sure. He’s a familiar face; get his name from the maître d’.
8 p.m.: UES dinner with St. Bernard’s Boy. He’s cute but kind of bland. Recall funny conversation about how personality has been almost completely bred out of the better Mayflower types; choose to interpret his dullness as the sign of a good background.
9:30 p.m.: On the fence about hooking up. This was a legit date, and I’ll reflect poorly on Best NYC GF if I’m not into following up post fooling around. Suggest we go downtown for drinks.
11:34 p.m.: In my apartment for a “nightcap,” the world’s most ridiculous word. It’s pronounced “hook-up.”
12:04 a.m.: Did he mention playing sports? The kid is ripped. Wish I had been paying attention to the conversation at dinner.
12:10 a.m.: Think it was a racquet sport. Wonder if I could beat him.
12:45 a.m.: He’s surprisingly aggressive, and keeps pinning me down, ripping my shirt a bit. I’m super into it, and once we’re undressed, I fight back just so he’ll pin me down again.
12:48 a.m.: Get an accidental elbow to the mouth. Awkward. I think it’s hot though. Fight back harder. More awkward?
1:05 a.m.: Keep pushing his head down my stomach, he keeps coming up for air. I go down on him for a bit to highlight the unsubtle hint, resurface.
1:45 a.m.: He leaves. I miss trusting sexual partners, when you can relax and go wild. In the right context I get into really dirty talk, aggression/submission … basically the high-risk stuff I don’t admit I like.

DAY SEVEN

8 a.m.: Tired, hungover, head to West Side Highway to sweat it out. Mid-run, I see Crazy, a guy I was not into and once threw in a cab when he went in for the after-dinner kiss; he proceeded to get hammered and freak out via text. He glares at me; I run faster, glare back, punk.
8:50 a.m.: Think I got jizz on my unsent thank-you notes last night. Klassy.
8:56 p.m.: Birthday dinner, flirting with D-1 athlete/banker. Its almost impossible, as his halitosis could fumigate one of those houses on Hoarders. I need a drink. What a waste.
9:25 p.m.: Peripheral Published Probable Gay gets my number. He has that beautifully clear, taut, Jewish–Mediterranean skin. I normally don’t go for dark and swarthy, but I bet he looks gorgeous naked. Consider the dirty things I want to do to him.
11 p.m.: Friend’s former colleague/my former hook-up, MS, arrives. Always forget NELAC (Northeast liberal arts college) gays are the hottest in the city: smart, self-confident, outdoorsy. Wonder if the college generalization thing is still relevant.
11:35 p.m.: Chatting with MS. Yes, it’s still relevant.