sex diaries

This Week’s Sex Diary: The Record-Store Worker Questioning Non-Monogamy

Photo-Illustration: Marylu Herrera

In this week’s story, an aspiring music journalist gets fingered while watching The Sopranos and wonders if they’re getting too attached to their lover: 25, single, Chicago.

DAY ONE

6 a.m. Wake up to Jordan’s alarm. I show them how to work my shower then lie in bed face down while they get ready for their shift.

7 a.m. Drive Jordan to their café for work. I always end up doing this for people I’m seeing, even though I prefer not to get out of bed before 10 a.m. when it’s just me. On the way home, I stop at the McDonald’s drive-through for breakfast.

10 a.m. I look at the old sex tape my ex sent me yesterday after I asked him for it. I recently started thinking about making an OnlyFans, so I wanted to collect footage. It feels kind of weird to look at the video now. We broke up in 2021 after dating for two years. It was mutual; we both kind of accepted that the relationship ran its course.

“We look so straight,” I text him. “It’s true,” he says. “We look 40 percent gayer now.”

12 p.m. I get to the record store for my shift a little later than usual and open up the shop.

5 p.m. I text Jordan during a lull at work to ask how their shift at the café was.

“I’m drunk in bed, that’s how it was,” they respond.

We talk back and forth a bit, and I recommend a record. They don’t ask me many questions. Sometimes I wish they’d express more interest in the things I send them. It’s not like we’re in a relationship, but I want them to be infatuated with me.

7:30 p.m. I close up the store and head home. Today was slow, and I’ve spent a lot of my shifts alone lately.

The owner stopped working one-on-one with me a couple of months ago. I noticed not long after that he’d blocked me from the store’s Instagram, his only account. I suspect it has to do with us flirting when I started working there. I’d tried my best to repress my attraction to him, and I knew he had a girlfriend, so I never thought things were super dire. I’m mostly mad that my boss never talked to me about the situation and that he’s still hiding from me like a coward long after I’ve gotten over my crush on him. I guess that’s what I get for working for a 29-year-old.

8:30 p.m. I’m watching Bob’s Burgers with my roommate when Jordan texts me. They’re sad because their other crush rejected them. They invite me over to cuddle, but I say I’m too tired and counteroffer to hang out tomorrow. Even though I’ve told Jordan I’m nonmonogamous, I have mixed feelings about our conversation. I’m glad they’re confiding in me, but I also worry that I’m a second choice to someone else.

DAY TWO

6:15 a.m. I guess my body is adapting to Jordan’s schedule.

9:30 a.m. I forget to bring my already late rent check to the landlord’s office and leave for the chiropractor. I’ve befriended some of her staff, especially the nonbinary massage therapist; today we have a nice chat about their boyfriend’s bizarre food preferences.

3:30 p.m. I spend a few hours working on projects — when I’m not at the shop, I freelance as a music writer and photographer, but I cover all things arts and culture, often with a focus on gender and sexuality. I also co-run the photo booth for a seasonal music festival in Chicago. When I wrap up work, I hit up Jordan, but they’re about to take a nap.

5 p.m. Jordan says they want the night to themself. I’m disappointed, even though I’ve spent much of the day questioning whether I’m getting too close to them. I pop open a beer and put on an episode of Bob’s Burgers, promising myself I’ll work some more on my music newsletter afterward.

10:30 p.m. Early bedtime.

DAY THREE

7:30 a.m. Wake up to a string of texts from Jordan that end with, “I kinda wanna have you over.”

After a while, I respond to tell them I went to sleep at like 11 again. Then I make dinner plans with my friend Soph for tonight. We’re going to make stir-fry.

10 a.m. Chiropractor again. My neck and shoulders are super flared up, and I don’t know why. On the way there, I sext with Jordan. They send me videos of their dick, and I tell them I want their cum inside me. After I park in the garage, I make a video where I’m stroking myself lightly through my cargo pants. Fuck, now I’m horny.

11 a.m. My body still feels iffy after the chiropractor. I head to one of my regular cafés to eat a bagel and work with my friend Sarah. Her fiancé’s dad is visiting and decides to join us. I get along really well with him, and I’d be lying if I said I don’t have a bit of a crush on him. He’s got a couple of weird tattoos, and we get into a fascinating conversation about mental health and music.

4 p.m. I do yoga. My neck and shoulders feel normal for like five minutes before returning to a dull ache. As I’m about to hop in the shower, I see a text from Soph canceling our dinner plans. My mind immediately turns to booty-calling Jordan, and I feel guilty for having that reaction rather than feeling disappointed.

7 p.m. I make myself finish my newsletter before hitting Jordan up. They offer to come over in an hour, so I cook dinner.

8 p.m. I pick Jordan up and bring them back to my apartment. We watch The Sopranos, and halfway through the second episode they start fingering me. I turn to face them, but they nudge my head back toward the TV. “Keep watching,” they instruct me.

Eventually, we pause the show. As they’re fucking me from behind, I ask if they like to be called “Daddy.” They cum immediately.

We fall asleep spooning in bed, watching King of the Hill.

DAY FOUR

6:15 a.m. I wake up and drive Jordan to work again. I don’t know why we keep hanging out the nights before they have to get up early.

12 p.m. Keith, who I know through mutual friends, DMs me on Instagram to compliment my newsletter and asks if I’m coming to a party he’s working that night. Keith and I have a will-we-or-won’t-we dynamic, mostly because I’m 25 and he’s 42. I tell him yes and text the organizer to get on the guest list.

9:30 p.m. While I’m getting ready for the party, Jordan texts that they’re having a weird night. We chat for a bit, and they invite me to hit them up later if I feel like it.

10:30 p.m. The party is in a random part of the city, at an event space near a bunch of upscale restaurants close to downtown. The interior is huge, with visuals from Keith’s video company dancing across brick walls. I wander around the mostly vacant upper floor before finding him and his two co-workers stationed before some computers in a corner like the man behind the curtain in The Wizard of Oz.

Keith gives me a big hug. We talk for a bit, and my friend Claire comes over with the event organizer. I chat with her, and we head downstairs to dance.

11:30 p.m. Ana shows up with a whole entourage. We started hanging out this past fall, but she’s blown me off the last two times I tried making plans with her. Still, she’s so fun, and we dance as I get to know some of her friends.

12:30 a.m. I cash in on Jordan’s booty-call offer and meet them at a neighborhood dive bar I’ve wanted to try for years. I’m drunk from overpriced drinks, and they order shots to catch up with me. We go back to their place, where they make me watch gamer YouTube before we hook up and go to sleep.

DAY FIVE

8 a.m. I wake up to Jordan’s alarm with an excruciating hangover. They let me stay at their apartment when they leave for work. I fall back asleep, and I keep having dreams where I can’t tell if I’m awake or not — visions of their roommates roaming around the apartment, having people over, Jordan coming back from work unexpectedly.

11 a.m. I wake up later than I have in weeks, still feeling like death.

4:45 p.m. After some food and a nap, I take the train back to my apartment. From there, I drive to the suburbs to visit my friend who’s recovering from foot surgery. She’s there with family friends — a rabbi, his wife, and their 25-year-old tattoo-artist son. Very sitcom.

8 p.m. Back at home, I watch The Holdovers, which my roommate suggested. I cry at the end and go to bed at 11 feeling more exhausted than I have in a long time.

DAY SIX

12 p.m. I slept for 11 hours.

1 p.m. I meet Soph for tea to catch up before they head out of town to play some shows. We talk about some stuff with Jordan, which is still bothering me. “I’m not sure I see them becoming a serious partner,” I find myself saying. “The sex is so good, though.”

That’s the good thing about non-monogamy, Soph reminds me. I can keep things casual with Jordan and find someone else to better fulfill my emotional needs. I resolve to slow things down.

3 p.m. I pick up an extra shift at work, and while I’m there I confirm some plans with Jordan … I’m going to take promotional photos of them in exchange for some vintage, queer fetish magazines they have.

8:30 p.m. After work and dinner at home, I walk over to 7-Eleven for some overpriced ice cream while texting Jordan. They say they’re craving fries with goopy cheese, and I send them a picture of several Tostito’s containers of the stuff. They seem to hint that they want me to deliver it to them but stop short of actually asking me.

I resist the urge to ask if that’s a request, and respond with a simple “lol.”

11 p.m. Jordan and I end up sexting each other. Slowing things down doesn’t include virtual intimacy, right? Plus, isn’t it the emotional side of things I’m worried about?

I use a big dildo (from my ex; Jordan doesn’t know that) with a bullet vibrator and cum really hard. I get part of it on video. I’m pretty pleased with some of the footage; I look hot.

DAY SEVEN

6:15 a.m. I wake up before sunrise and lie awake until my alarm goes off at 8:30. I definitely have a cold, but I test negative for COVID.

10 a.m. I struggle a bit to find my chiropractor’s new office and overexplain my KN95 to virtually the entire staff.

3 p.m. I pick up yet another last-minute shift at the record store despite my cold. I’m in no position to turn up extra income. I treat myself to Potbelly before heading over.

8:30 p.m. While eating dinner and binge-watching Bob’s Burgers with my roommate, I text with Jordan, who tells me they’re selling an old jacket to a guy they know in New York. “He bottoms for me, and we’ve been quietly in love for four years,” they say. Jealousy balls up in my chest despite everything. Despite my claim that I want to keep things casual with Jordan. Despite my non-monogamy.

10:15 p.m. A while later, Jordan texts me to ask how Potbelly was. Maybe they’re worth it.

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The Record Store Worker Questioning Non-Monogamy