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Photo-Illustration: Marylu Herrera
This week, a guy visits a fling who likes to rub his belly while feeding him grilled cheese: 33, single, Brooklyn.
DAY ONE
7:30 a.m. I wake up earlier than I’d like on a weekend, but I have my first session with a personal trainer at my gym at 9. After I get out of bed, change quickly, and then walk my dog around the block.
9 a.m. Arrive promptly for my training session. It’s tough, but my trainer is motivating. I’m trying to focus on being as healthy as possible right now. I’m two years out of a long-term relationship and have been enjoying being single so far; I’m just trying to focus on good friends and good sex. My ex and I were together for eight years. We broke up because he basically decided he didn’t want to be with me anymore. It was a fairly clean break because, while I was devastated, I’m very much of the school of thought that if you don’t want to be with me, I don’t want to be with you. Anyway, I can tell I’m going to be very sore the next day.
11 a.m. I go into the stream room afterward hoping to find some fun, but no luck. I walk back to my place, walk the dog again, and then eat leftovers for lunch while pondering what I want to do the rest of the day.
1 p.m. I get a message on Grindr from F, a guy in my neighborhood who I’ve been hooking up with for over a year now. He says, “Shower and come over, I want to suck your dick.” He’s in an open relationship so there’s no questions about dating; it’s purely for sex.
1:45 p.m. After I shower, I head over to F’s place. He always lets me come over because I have my dog right now — I share custody with my ex — and he can be annoying when I have someone at my place for a hookup. I get to F’s apartment and we get straight to business. The only trouble with us is that I’m a pretty steadfast bottom and very orally inclined, while he’s fairly versatile but has been wanting to bottom or just be submissive lately, so we’ve been settling on trading blowjobs, but this time it was just him blowing me. Could be worse.
9:45 p.m. I get a new match on a dating app. G is very attractive and has a cool job, but lives in L.A., so it likely won’t go anywhere, but we end up messaging for quite a while on the app, basic topics, nothing groundbreaking. We trade numbers so we can text.
DAY TWO
8 a.m. I wake up early again because I agreed to another training session, but this time a little later. Because I have a little bit of extra time after fulfilling my dog duties and before having to leave, I jerk off.
11:45 a.m. G texts asking how the gym was. I sort of forgot everything about him already, so I have to look at his profile on the app again and skim our conversation there to refresh my memory. We end up texting for a while and get into what we like sexually. It turns out we like the same things, i.e., both wanting to bottom.
3:45 p.m. I text A, another guy I met on Grindr from my neighborhood who’s in an open relationship and is easily the hottest man I’ve ever been with and has the biggest dick (my jaw is sore for days after we hook up). There’s one catch, though — he fetishizes my body. I have a belly, love handles and man boobs. I’ve pretty much always been like this my whole life, except for a few years in college when I capitalized on my youthful metabolism and worked out twice a day. That was short-lived, and I’ve basically accepted I’ll always have a dad bod with a bit more to love. A is obsessed with my torso and loves to grab it and touch it. Okay, whatever. But now it’s growing into him wanting to feed me my favorite meals after we hook up. Like, I’ll sit between his legs, my back to his chest, and he rubs my belly while I eat grilled cheese or something. It’s wildly weird, but also like, not a bad deal for me? He’s praising something about me that I hate and feeding me at the same time! Talk about a mindfuck.
5:15 p.m. Texting goes on for a while, mostly dirty and telling each other what we’re going to do to each other the next time he comes over. He can never host because of his relationship, which is fine but just requires him not coming over for weeks at a time while I have my cockblock of a dog with me. I do really love the dog.
7:30 p.m. I scroll through the apps trying to find a hookup who can host but come up short. I spend more time than I’d like to admit on Grindr, Scruff, Sniffies, and The Blowers.
DAY THREE
7:05 a.m. Wake up to fulfill my dog-dad duties and then head into the office to start the week. I work in communications at a big global company. It’s a fairly new position and has been great so far. I spent far too many years at a job I hated, but this one feels really nice.
12:15 p.m. Slowly getting through the day of several Zoom calls. I’m in the office four days a week, but my entire team sits in London, so my workdays can be quiet in terms of actual in-person human interaction.
2 p.m. I see that J, who I’ve been messaging on Scruff for a few months, is really close to me on the grid — which means his geographical location is close. I message him noting his close proximity and mention my work address (it’s a big building with lots of companies, so it’s vague at best). We then discover we work for the same company, just in a totally different department and in an adjacent building. How … awkward. He says he is in an open relationship (apparently that’s my type), and we actually have really witty banter with the occasional sexy undertone. It also turns out he’s on my floor, in a meeting, and we make plans for him to come by my office when he’s finished.
3:15 p.m. J swings by my office and we chat for about 20 minutes. I have two walls of glass in my office. It feels like being in a fishbowl, so there’s no funny business to be had. He definitely does not disappoint looks-wise, and the chat is just as good in person as it was on the app. I thought I caught him once or twice making sexy eyes at me, you know the kind of direct eye contact that lingers for just a beat too long? Feeling cautiously optimistic that he’s still into me after seeing and meeting me in IRL.
6:30 p.m. At home and relaxing on the sofa. I see something on Instagram that J and I talked about earlier, so I take the plunge and DM it to him — we don’t even follow each other. I am feeling bold!
9:30 p.m. I didn’t scroll on the apps as much tonight. I think because I was riding the high of the IRL chat with J.
DAY FOUR
7:30 a.m. Arrive at the gym bright and early, and it is already packed with the hottest men. The corporate types who wear suits and such. I should come at this time more often.
11:15 a.m. Work is slow, so I have time to catch up on news and personal things like pay a few bills, look for a new dermatologist, things that fill the day until I can head out around 4. It’s early, but because my team is in London, they more or less sign off around 2, so I stay a little later to save face with the other people I sit near in the office.
4:30 p.m. Leave the office for the day. It’s swampy outside, and my walk to the subway is not short. I hate being hot and sweaty; it’s the worst feeling to me. I joke and say that I’m grumpy May through September, but there is definitely some truth to it.
7 p.m. The heat finally breaks, so I change and take the dog for a long walk around the neighborhood. I truly wish there was more eye candy around here, but alas it’s an area with a lot of families, and straight dads are just not my thing.
9:30 p.m. Because the dog is going to this other dad in a few days, I text A asking if he’s free soon to come over and send him a picture of my bare torso. He replies right away and says “maybe” and asks about the following week. That’s a bummer, but patience is a virtue.
DAY FIVE
7:15 a.m. Wake up and realize I don’t have any morning wood and vaguely remember I didn’t have any the day before. Fairly weird for me, and most guys, I think? But I’ve sort of noticed my sex drive, or at least my desire to jerk off, has dulled a bit since doing the harder workouts. I thought it would be the opposite?
8:30 a.m. Get to the gym to do some cardio. It’s the same sexy crowd. The locker room is filled with half-dressed men in suits. Be still my heart — and my dick.
1 p.m. At work and scrolling through the apps in between meetings and calls. The guy who’s usually free for a blowjob close by hasn’t been on for a day. I think about sending him a sexy message on WhatsApp but decide I should show some professional decorum.
4:15 p.m. Leave the office to head home. I desperately need to do laundry because I’m running out of fresh gym clothes. I sweat — a lot — when working out.
7 p.m. I binge-watch some YouTube videos. I’m newly obsessed with these “Out & About” episodes on BarStool Sports. I think it’s the only gay content it has, and the two hosts are hilariously problematic.
DAY SIX
6:30 a.m. Wake up bright and early because today is the day that I give the dog to his other dad for a few weeks. That really means my hunting season begins.
8:30 a.m. Have an awkward exchange with the ex. We planned to meet outside his building, and it is very obvious that he’s just coming up … from the night. He’s rolling in on a Citi Bike no less. There’s no explanation of where he’s coming from, but it’s not my business anyway.
3:30 p.m. Work has been very productive and is just now starting to slow, so I text F to see if he has plans tonight and would like to come over later — and tell him I have a four-day load for him. I’m not usually so top-y, but he can bring it out in me. Maybe I’m still discovering what I am and am not. Who knows.
5:30 p.m. F comes over and it’s great. I come (and he doesn’t) and we chat about poppers and how he’s trying to wean off them. I enjoy poppers but don’t need them or crave them all too much. They’re like a special little treat to me.
9:15 p.m. I’m cozied up on the sofa, alone, and sexting with A. He says he’ll come over tomorrow. Yes! It’ll be after his shift at the local food co-op. How crunchy.
DAY SEVEN
8 a.m. Head into the city for another training session. By the end, I feel like throwing up, but I’m happy I pushed through.
10:15 a.m. Home for my one work call of the day. While my company doesn’t officially have Summer Fridays, they are always very quiet and don’t require much attention.
Noon My housekeeper arrives to help reset the apartment after the dog leaves. He sheds a lot and I can only vacuum so many times a day before I lose interest.
4:15 p.m. After walking around the neighborhood for a bit and reading on my roof, I return to a beautifully clean apartment. I relish in the feeling and will enjoy it for the next few weeks before all hell breaks loose again with the dog.
8:15 p.m. A finally arrives after a few delays finding a Citi Bike port. He is handsomer than ever, and has a lot more chest hair than I remembered. He says he trims it often.
8:45 p.m. Our hookup is the best. He’s so passionate and dominant and pushes me to my limits in a respectfully sexy way. I was mildly nervous he would be musky after the co-op, but he smelled delightful as ever, so much so I sucked on his toes and sniffed his pits, which are two things I only do with him. I think I push my limits with him because he’s complimentary of my body and that’s my subconscious way of thanking him? Something I should perhaps touch on in therapy. That’s next week’s problem.
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