sex diaries

The 25-Year-Old Hooking Up With 6 Guys in 7 Days

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New York’s Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. This week, a single man with a plethora of lovers: gay, 25, book publishing, Bushwick.


10 a.m. I woke up hung-over and texted Jude to confirm the drunk plans we made last night at the bar. He’s still down to hang out and watch RuPaul’s Drag Race. I fall back asleep.

11 a.m. Freshly showered, I build my outfit around a jockstrap. You never know — Jude and I sometimes have group sex together, using Grindr and Scruff to find guys to play around with.

Noon I show up at Jude’s; he’s unshowered and wearing nothing but sweatpants. Hot.

12:30 p.m. We’re watching RPDR and cuddling. J and I tend to assume semi-platonic roles when we’re alone together. I put a frozen pizza in the oven, his arms around my waist.

1 p.m. I’m laying across his lap and feel a boner. We look at each other and start vigorously making out to the sounds of drag queens lip-syncing.

1:15 p.m. What is HAPPENING? We never fuck alone — it’s too intimate, and Jude works with a guy I dated seriously in college. He smells sort of bad, but in the good way.

1:30 p.m. “Wait, wait, wait, wait,” he says, lifting himself off me. “I don’t know about this.” He goes to the bathroom.

1:32 p.m. “Fuck it,” he says as he comes out of the bathroom, climbing back on top.

1:40 p.m. The smoke alarm screams. The pizza! We run to the kitchen in our underwear to find a sad, charred hunk of bread where a cheese pie used to be.

1:50 p.m. We’re sitting in bed discussing our options. Jude wonders if the Great Pizza Incident of 2016 might be a sign that we shouldn’t fuck. I tell him that if he’s not 100 percent on it then it’s a complete no-go. (Guys, consent is crucial!)

2 p.m. We’re back on the couch, cuddling and watching Broad City. Both riled up from the Great We-Almost-Had-Sex-Just-the-Two-of-Us Incident of 2016, we start chatting with guys on sex apps, trying to find someone to come over and blow both of us.

3 p.m. I get a Grindr message: A waiter at the Chinese place across the street is on his lunch and looking for some fun. After getting the okay from Jude, he comes. And so do we.

3:45 p.m. Back on the couch cackling at Abbi and Ilana’s misadventures. We decide I’m the Ilana to his Abbi, and vice versa.

7 p.m. I get a text from Danny: “Wanna sleep over tonight? ;)” I do. Danny is a friend of mine who used to be my editor at a magazine I worked at ages ago. We fuck occasionally — just the two of us.

7:45 p.m. I say good-bye to J and hop on a train to the West Village. In a coincidental twist, Danny also used to work with Jude and the aforementioned college ex. Sometimes I think about the three of them spending 40 hours a week within five feet of each other and wish I could’ve been a fly on the wall. I’m glad that’s no longer the case, though: If Danny and I ever ended up in a relationship, I wouldn’t want him in such close proximity to my ex (for his own sake, at least).

8:30 p.m. Danny and I are sexting, and I arrive super horny. He’s in the middle of cleaning his studio, but it’s game over from the moment he opens the door: I’m blowing him almost immediately.

9:30 p.m. We order dinner. I’m starving, since my lunch was set on fire earlier while I was making questionable decisions. Should have had that waiter bring over food. We cuddle in bed, smoking weed and watching nature documentaries.


11 a.m. We stir awake, groping each other half-asleep until it turns into a full-blown hookup session.

Noon Hand in hand, Danny and I spend the day wandering around downtown, sipping coffee and exploring, popping into stores that pique our interest, and generally being a cute couple.

3 p.m. Ugh, it’s so nice. Dan’s great. Smart, funny as hell, charming, driven … if I wasn’t categorically opposed to being in a relationship right now, I would probably pursue something more with him.

5 p.m. We part ways and I go to the gym — but I go back to Danny’s place after and sleep over again.


9:30 a.m. At the office uptown, I have my first cup of coffee of the day. The combination of a good workout and sex the night before has me riding high. A co-worker can tell: “And what did youuuu do this weekend?”

Noon I get a Facebook chat from this cute guy Mike I met at a Friendsgiving party in November. “Long time no talk!” I already know where this is going. “At the office,” I message. “Here’s my number though, text me.”

3 p.m. I get out of a meeting where several of my copy concepts for an upcoming ad campaign were shot down. I have a text from Mike waiting for me. “Have you ever seen Practical Magic?” I tell him I haven’t, and he’s incredulous.

7 p.m. I arrive home, where I immediately get into bed. It’s been a long day. New text from Mike: “What are you doing tonight? Want to watch Practical Magic?” I evaluate where I am physically, mentally, and spiritually, and decide to go for it because I’m young or whatever. I respond: “… and chill?” He says, “Be over in an hour,” and I freak out.

7:05 p.m. Still freaking out because I have 55 minutes to shower, clean my room, pick out a cute outfit, and douche before he comes over. I don’t know if I have to douche, but we didn’t discuss sexual proclivities in detail, so I don’t know if he is expecting to top or bottom. Still, better to be safe than sorry.

8 p.m. I complete my checklist with time to spare (and smoke a bowl). The movie was halfway through before hands started creeping, exploring the boundaries of familiarity that we had yet to establish as two relative strangers. Before I know it, pants are off and poppers are on the menu.

8 p.m. As soon as things start getting hot and heavy, Mike pulls away. “Question … ” he begins. I am ready with data. “When’s the last time you were tested? I’m negative as of a couple days ago, and I’m on PrEP.” I let him know that I’m also negative as of last week, and while I’m not on PrEP, I haven’t had unprotected sex with anyone since. We decide to forgo condoms. I make a mental note to ask my doctor if PrEP is right for me.

9 p.m. Topping without a condom is the best feeling in the entire world besides having your ass eaten and dick sucked at the same time.

10 p.m. It was one of those really laid-back, silly sexual situations where two people have amazing chemistry and are comfortable doing things like giving each other raspberries and tickling or collapsing into one another and randomly breathing a simultaneous deep sigh of satisfaction. After I fucked him, he returned the favor. We alternated between casually hanging out and having sex on and off for two hours, and while I’ve now only seen half of Practical Magic, I’ve climaxed to its climax.


6 a.m. Mike’s alarm goes off. I groggily check my phone as he climbs out of bed, naked. The time is …

6:09 a.m. I show him my phone. “Look at the time!” I said to him with a giggle, grabbing his package.

9 a.m. I get off the train at the office to a text from Mike. “Had a really great time last night!” So did I. The thought hits me that I kinda wanna spend time with him just hanging out, and I get nervous. I always get nervous when I start wanting to do clothed activities with boys. My last relationship didn’t end well, and the thought of going through all of that again is enough to make me want to be a perpetual bachelor.

1 p.m. At the office knee-deep in work. My phone buzzed. “Still on for tonight?” DJ texts. Shit. I had totally forgotten. I quickly gauge a variety of factors, including whether I have accidentally double-booked my evening since I forgot our plans (I have not), if I feel sexy (6.8/10), and if I feel like having company over (I sleep better with others, anyway). “Sure,” I respond; I feel like an asshole having already canceled on him twice before.

7 p.m. I get home, quickly made myself presentable, and get cleaned up a little. He comes over and we’re naked before asking each other how our respective days were.

8 p.m. The first time DJ and I had sex, it was a shitty situation, if you know what I mean. I wrote it off as a fluke. I’m not perturbed by that sort of thing; I understand that if you’re putting a dick in an ass, poop is a possibility. The second time it happened, I had A Talk with him about the wonders of douching. It has since been largely a nonissue.

9 p.m. DJ also hogs the water in the shower and doesn’t make efficient use of the entire tub length, washing himself and pushing up against me as I’m under the stream. I found myself getting short with him: “There is so much room for you to lather up right behind you.”

10 p.m. I let him stay over. He’s lucky he’s so hot.


9:30 a.m. I get a Gchat from my roommate: “We need to talk.” Uh-oh.

10 a.m. “Who the fuck did you bring home last night?” Since DJ went from douching in the bathroom right to my bed, I didn’t see that he had left behind a huge fucking mess … but my roommate did. I apologize profusely. I don’t think he’s going to be coming over again any time soon. But I’m not opposed to going to his place.

12:30 p.m. I’m on Instagram and see a sexy shirtless pic of Malcolm on Instagram. We met on Scruff and fucked a couple of times last fall. The plot thickened when we ran into each other at a friend’s birthday party and I found out they used to be an item. It’s a small world, but a sex-positive one — our mutual friend was totally cool with it, and encouraged our relations.

1 p.m. I can’t stop thinking about Malcolm’s hairy chest. I text him: “Hot Instagram. Long time no talk.”

3 p.m. No response. I shrug it off; maybe even though his ex/my friend is cool with us fucking, he’s not, and that’s okay.

4 p.m. “Hey! Thanks, looking good yourself. How ya been? Haven’t seen you since Yom Kippur.” The fact that he remembers the last time we boned makes me feel warm.

5 p.m. We make plans for him to come over soon. “What about tonight?” He asks. Even though I’m horny, I hesitate, thinking about the fact that I’ve had guys over the past two nights. But then realize I’m slut-shaming myself. “Sure!”

8:30 p.m. He comes over and before we know it we’re in bed in our underwear, smoking and just talking. “Do you mind if we don’t hook up tonight? It just hit me how tired I am.” I don’t mind at all; he’s really fun to just be with.

9 p.m. It’s lovely sometimes to just cuddle with someone and watch TV without sexual expectations.

11 p.m. We had been asleep for an hour when I wake up to his mouth around my dick. I guess the friction between us cuddling naked inspired him. I get hard instantly, and we go at it like animals in the middle of the night.


7:30 a.m. I leave Malcolm in my bed because he doesn’t have to be at work until later. I’ll allow guys to stay at my apartment after I’ve left depending on familiarity and trust.

12 p.m. I’m texting with Mike. We’re having such a good conversation that’s been lasting for days, ever since he Facebook-chatted me. We make plans to hang out on Saturday afternoon and “go to the park or whatever,” and I wonder if it’s a date.

6:30 p.m. At happy hour with Jude, talking about the weeks we’ve had. He tells me about the guys he’s been sleeping with. I briefly outline my week’s sexcapades, but can’t stop talking about Mike. “Do you, like, like him?” Jude asks. “I have no clue what that feels like anymore,” I respond, “so … I don’t know?” He laughs. “Well, what about Danny? I thought you two had something special. Oh my God, TBT to when me, him, and you-know-who worked together. Have you still not told him about the fact that we have our fun sometimes?” I haven’t; I don’t think it’s relevant, and wonder if that attitude makes me a monster.

7 p.m. Maybe I’m rude for juggling these guys and an idiot for trying to manage the different levels of intimacy that come with each. Maybe I’m brilliant. After all, I went from being a serial monogamous dater to being a one-night-stand aficionado — and have now somehow found myself striking a balance. I’m involved with a great group of dudes who I have great sex and conversation with, who fulfill me in ways both physical and emotional, without the weight of monogamy or expectations. And that’s probably what I need right now.


9 a.m. I wake up for work in a great mood despite being a bit hung-over from happy hour.

12 p.m. So many group texts with people asking each other what the plan is for going out tonight. I’m a bit tired but commit to my favorite bar on the Lower East Side with my best friends.

5 p.m. I leave the office and head downtown. I walk into the bar and my group of closest friends is at our usual table, already two whiskey-gingers deep. They all spot me and scream. It’s gonna be one of those nights.

9 p.m. While I’m bar-hopping I’m texting with Danny, and make plans to sleep over at his apartment this weekend after the gym, like I did last week. “I miss you,” he says. I’m so drunk I forget to answer.

11 p.m. Three bars later and the group of gay guys I’m with are heading to a sex club for a little late-night action. I join them more out of obligation than an immediate desire for anonymous play. I end up not participating: It’s too hot, and I’m exhausted. I sip a beer on the sidelines, watching guys blow each other on the dance floor and thinking about the dudes I’ve fucked this week whose names I actually know.

1 a.m. I’m in bed, setting an alarm to wake up the next day to hang out with Mike. I see Danny’s “I miss you” text, but it’s too late to respond.

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The 25-Year-Old Hooking Up With 6 Guys in 7 Days