sex diaries

The Media Associate With a Thing for Aggressive Older Men

Photo-Illustration: James Gallagher

This week, a single man trying to work through his intimacy issues: gay, single, Harlem, 30.


7 a.m. I wake up early.

9 a.m. There is a message from R. The “relationship” with this man (he is a gray-haired man in his 50s, which is apparently my emotional jam) exists entirely inside my head. We went on a date once, when I lived in his city a couple years ago; we hooked up once last year when he came to New York; and now we have a semi-regular, slow-moving exchange.

12 p.m. It’s been a useless day; I haven’t accomplished much. Suddenly it becomes very important to get specific groceries from a store in Queens.

5 p.m. Home. There’s nothing wrong with starting to drink by yourself at 5, is there? I send a message to R., open-ended enough that he will at least have to reply.

10 p.m. Drunk enough to go to bed. I am pretty sure I did not exchange actual, out-loud words with anyone today. Having lived here two years, I am beginning to worry that this is just what life is going to be like — entirely silent weekends. But if you are going to be isolated, New York is not a bad place for it.


6 a.m. Wake up to a message from my high-school friend D. It’s a silly meme, but D. lives far away, so things like this are important to me — low-key, regular communication that makes me feel like we are still part of each other’s lives.

8.30 a.m. Start the week off right: therapy! My doctor keeps trying to convince me I’m into D., who is straight, and I find the idea ludicrous, although I did briefly have a crush on him in high school. This feels like a detail Dr. K would run too wild with, so I just say that I love D. too much to ever want to sleep with him. This reopens our usual discussion about why in my head and bed those things are entirely separate.

11 a.m. P is online — another man in his 50s. We’ve hooked up a handful of times over the past few months — he comes over, I blow him, he smacks me around — but lately he is a hard man to trap; I don’t know if he’s playing hard to get or if he’s just busy. I want him more than he wants me, and both of us probably enjoy the power trip.

He’s near my apartment and wants to meet on his lunch break because he’s mad about something. Yes, I will totally bail on work for this. My job may be the only source of meaning in my life — I work as an associate at an international nonprofit media company— but practically speaking, most of the team that I deal with is not even in this time zone, so half of them are asleep anyway …

12 p.m. The doorman calls up to say P. is here — this is the only way I know his name, and for all I know it’s fake. As soon as the door closes, he puts his hand on my neck and pushes me down on all fours, and makes me crawl to the couch while he kicks me. If this is what P. is like on a bad day, I’m here for it.

12.40 p.m. Today P. wants to ejaculate on the floor. Unfortunately, I know exactly how clean my floor is, and as much as I hate saying no to him, I’d rather not. Eventually we compromise and I get a bowl from the kitchen. Soap will get semen off ceramic, right?

1 p.m. Bye, P. I wash my face and check my work email.

6 p.m. Scrolling through Meetup groups, signing up for things I know I will never actually do.


10 a.m. Stuff at the office has piled up, but the overload works for me; I like being busy. No reply from R.

4 p.m. It never rains but it pours: Grindr tells me that the Spanking Man — another guy in his 50s — is nearby, and I send him a message. He texts me, asking why I messaged him on “one of those apps.” I say I broke my phone, but the truth is that I deleted his number a few months ago, after I asked him point-blank to go on a date with me and he waffled. We settle on hanging out tomorrow after work.

7 p.m. Yoga. I have tried several places to find the least annoying one, and at least the music here is good, though.

9 p.m. At home, I take a shower, order dinner, message D., who has dates for his next work trip to New York. I put them on my calendar and am happy there’s something to look forward to. It feels a lot like having a big brother come visit.


6 a.m. R. has texted, asking for a new picture of me. Hmm. I told him I was growing my hair out; is it a good sign that he wants to see what it looks like? Does it actually look terrible? Oh God.

2 p.m. I come across a Scruff profile that is appealing — older guy, aggressive, visiting, not looking for, ahem, butt stuff. I haven’t had anal sex in years, and my last experience with it was unpleasant. This hard limit has been an issue for a lot of guys, including R., who hinted the time we hooked up that in a “relationship” he’d need that. “In a relationship,” I hinted back, maybe I’d consider it.

The Scruff man and I exchange pictures, at which point he says, “Oh, sorry — too old for me.” I sort of knew from his profile he’d say that, but can also be a bit of a glutton for punishment.

7.15 p.m. At the Spanking Man’s apartment, which is extremely nice — immense, penthouse, beautifully furnished. We start making out and he asks if I’m ready for “discipline.”

7.30 p.m. The Spanking Man wants to try out his new cane. He gets behind me, close enough that I can hold on to his dick while he lays into me. “One day I’m going to spank you till I come,” he threatens. We shall see. I don’t even try to be quiet or stoic; it feels good to yelp, and he has an accurate sense for when I can’t take anymore.

8 p.m. I ask him to switch to the paddle. It’s a different sort of pain — less sharp but longer lasting, and I want to be able to still feel something tomorrow.

8.40 p.m. We are cuddling, this time with his head on my chest. I suddenly say I’m hungry and need to go. It takes me about two minutes to get ready and get out of his apartment, and he seems a little taken aback, which I am sadistic enough to appreciate.


9 a.m. Dr. K. insists that we meet twice a week. We are still talking about D. I wish we wouldn’t; it’s probably the best relationship I have, and I don’t want to dissect it to death or make it something strange.

11 a.m. R. says he’s coming to the city for a work thing and he’d love to see me, “but it’ll be really busy.” I don’t know why I’ve picked this man as the one to combine my sex-and-affection boxes.

6 p.m. Sitting on the subway was not a good idea — everything still stings — but an open seat on a rush-hour train is not something to be passed up. I will wince all the way home.

8 p.m. The Spanking Man wants to know how the day went and whether my therapist asked about him. How does he know my therapy schedule?! It irritates me that he somehow gets so much information out of me without revealing anything about himself, and I should really be better about withholding.


7 a.m. Wake up early and call my mom. She used to be very obsessed with the idea of me finding a “partner,” though lately her new thing is trying to convince me I should have a child, which makes me wonder what exactly I did to make her give up in such a bizarre way.

5 p.m. My co-workers are going out for drinks. There is a nice, quiet bar near our office; it’s not fancy, but the bartenders know us. Which is a nice feeling; I think the only other place I feel like a “regular” in the city is at the hair salon.

10 p.m. A. texts, asking if he can come over. A. is not in his 50s. He is, as Dr. K. would say, “age appropriate”; we met on Grindr when I first moved to New York, and have been hooking up since. I say no, because it’s late and I’m already semi-drunk, but he reminds me that he is being transferred for work next month and won’t get to “enjoy my services” anymore. I cave. Good dick does not grow on trees. And certainly not good dick that gets along with you.

10.20 p.m. A. is sweaty from riding his bike over and I would be lying if I said that did not work for me. Hooking up with him, though, is objectively pretty strange. It’s completely calm, neither exorcism nor fake affection, just extreme focus — I told him once that blowing him made the world very small; he was offended, but all I meant was that it made other things go away — distractions, anxieties; the world shrinks to the size of a dick, and even if the dick is big, it’s still all things considered pretty small. I think once I offered this explanation he was just confused.

11 p.m. Still at it. It always takes a long time to get A. off; I’m sure this would go faster if we didn’t chit-chat (he’s a lawyer, and is trying to explain LSAT logic games to me). Is this what relationships are like?

11.20 p.m. A. asks why I won’t let him fuck me as a going-away present. My ass is definitely not gift-level, but maybe I should let him, since it doesn’t seem like waiting for R. is sensible. On the other hand, A. is fairly impressively endowed — big enough that the thought of it going where no one has gone for years causes some trepidation. Although one does sometimes like to run before one walks.

11.50 p.m. A. starts breathing more shallowly, his balls tighten up, and he gets a tiny bit more aggressive, putting his hands on my head to get me at the speed he wants. It takes him a few more minutes, then he’s done, at last.


8 a.m. The combination of too much wine and 80 minutes of fellatio means my throat feels awful. This is a lesson I should have learned by now. Also to hydrate better.

11 a.m. Sitting at the laundromat when A. texts, wanting to know if he can come over. I just washed the sheets! But he’s “finishing up at the gym,” and I can’t resist.

12 p.m. A. arrives. He doesn’t take off his clothes, just stands by the door and pulls his shorts down a bit. I kneel, ask how his workout went, and get going.

12.40 p.m. He comes in my mouth again and says he will miss me. I point out that we are both rather easily replaceable — everyone’s got body parts, the world is full of etc. “We get each other,” he says, and it makes me kind of sad. As he helps me up it seems for a second like he’s about to try to kiss me, so I turn away. Maybe it is good that he is leaving; I’m not entirely sure where this would go, and if there’s one thing I hate, it’s uncertainty.

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The Media Associate With a Thing for Aggressive Older Men