sex diaries

The Barista Fantasizing About Sex With Her Boss

Photo-Illustration: James Gallagher

This week, a woman getting butterflies in her stomach at work while trying not to text her ex on their birthday: 27, single, Boston.


10 a.m. I am working as a barista at a bustling coffee shop. It’s the end of my two-week training session.

4:15 p.m. I sigh with relief as I leave the store, knowing I won’t have to return for another two days. It’s draining; the managers don’t seem to understand that I don’t know where things are. There’s this one manager, B, who really seems to have it out for me. She’s flat-out rude and doesn’t talk to me unless absolutely necessary. She’s also very hot. Bright dyed hair, arm tattoos, and generally pretty masc. My gay kryptonite. She’s also incredibly mean and impatient. Again, kryptonite.

6 p.m. When I get home, I immediately draw a bath and dump an obscene amount of salt in it. I’m 27, which puts me at the older end of our staff, and I can feel this job in my knees, back, and hips. I took this job because they help pay for college. Money is largely what kept me from going almost ten years ago. That, and I got a job right out of high school that paid and kept me busy for two years. I always said that I wanted to go to school for psychology. All these years later, I’m actually doing it.

8 p.m. I’m tired already and start getting ready for bed. I’ve been really, really enjoying sleep lately. Perhaps because “falling asleep” entails about an hour of uninterrupted fantasizing about my ex, M. After ending a five-year-long, straight-passing relationship last year, I quickly got into my first queer relationship with M. M is a sweet, goofy, hot, trans masc, nonbinary Prince Charming I met on Bumble. We had a wonderful, whirlwind romance for six or so months. After years of wondering what queer sex might be like, I finally knew (and loved it). Ultimately, our struggles revealed themselves. When we got together, they said they were nonmonogamous; this seemed fine at first, until one day they told me they didn’t see me as a domestic partner and wanted to sleep with other people. We parted ways and haven’t spoken since, my choice. It feels healthier that way.


7 a.m. It’s my Saturday! And of course I can’t sleep in, so I get up and make some coffee. My best friends, C and A, are gonna go downtown and walk around with lattes, my favorite pastime.

12 p.m. It’s a beautiful day. A and I smoke a joint and embarrass C by dancing around a fountain and singing songs from The Sound of Music. We point at buildings and say, “Oh, look at that,” and get cannolis that fall apart in your hands while you eat them.

6 p.m. We’re sitting by the river as the sun begins to set, and for some reason a photo of M comes to mind; they are holding onto fence posts and throwing their head back, the sunset shining on their face. It’s a really sweet photo. I miss them.

10:30 p.m. I’m trying to masturbate to M but it gets complicated. I like to fantasize about realistic situations and play them out in great detail, like a steamy scene from a movie, and edge myself ’til the end of it. But in my fantasy, I’m trying to create a realistic, unproblematic, and exciting context in which we’d fuck again. That’s hard. Oh, and their birthday is this week, so naturally I’m obsessing over whether or not to text them.


4:15 a.m. I wake up with a stomachache. Turns out chronic anxiety can pervade sleep. I have to open the store with B this morning. The idea of a whole hour one-on-one with someone who won’t speak to me makes me want to hurl.

4:58 a.m. I’m at the corner across from the store and B is out front. She stands leaning against a wall, one foot crossed over the other, and I take note of how my body responds to this. Being anxious and turned on at the same time is such an interesting experience.

5:30 a.m. What could I have possibly done to this woman, other than take too long to get sleeves, that could make her hate me this much? She says nothing. Every time I have to ask her where something is or how to do something — which is often — I’m met with the driest, most annoyed tone. I know I shouldn’t care whether she likes me or not and that it’s out of my control, anyway. But I do.

1:30 p.m. “Hey — you know how to make cappuccinos?” B strides up and asks me.

I shake my head no and she gestures me over to the espresso machine. “You take the pitcher, and slowly bring it down until you hear that sound like tearing paper — hear that?” The espresso machine makes a sound just like tearing paper, and I nod. I like watching her hands holding the pitcher. She has delicate, little tattoos on her thumbs around her wrists. “Wanna try?” she asks, and I snap back.

I take the pitcher and fill it, then submerge the steaming wand and pull too quickly.

“Slower, more like this —” Her hands occupy the empty spaces on the pitcher I am holding as she slowly guides us down, and I can’t help but think of Ghost and how I’d like to guide her hands down and wow this is some serious lesbian porn. “Try one more time.” I try one more time, and mess it up again. She laughs a little and says, “Yeah, almost.”

She’s a jerk, but my heart’s beating out of my chest as she walks away.

2:30 p.m. B has left for the day. I ask some co-workers about how to swap shifts with someone. I hope I can make it work — I’m supposed to work on a film set out of town that weekend. B is in charge of the schedule, but I want to have it all figured out before I run it by her.

7 p.m. Both of my best friends are busy and I don’t have enough brainpower left to focus on anything, so I smoke weed and scroll through Pinterest.


4:15 a.m. Another opening.

5:05 a.m. It’s M’s birthday. I didn’t remember upon waking, but when I signed in, I saw the date and it was like an actual slap across the face. Crap. Not this day.

6:30 a.m. There’s a steady flow of customers and I’m glad. I don’t want to talk to anyone today. I don’t have the energy; all of it is being fed to the running pros-and-cons list in my head. Do I text M or not? I was the one who ended contact and said I’d reach out if I was ready. I want them to know that I care, but then I might be opening a door I’m not ready to go through, and I wouldn’t want to disrupt their birthday.

11:30 a.m. I’m joking around with a co-worker and say something about “folks our age,” only to find out that he is a solid five years younger than me. B overhears and asks, “Wait, how old are you?”

“27,” I say, knowing this will shock her and reveling in how good it feels. “How old are you?”

“24,” she says. Everything clicks and I understand. She’s younger than I thought. She’s just immature! That’s easy.

2:30 p.m. B leaves for the day, and it’s like I can feel the dopamine draining from my brain. I feel myself begin to crash. This is exactly why I have started referring to my love life as an addiction. The highs and the crashes.

8:30 p.m. A reasonable hour to go to bed.


9 a.m. A later morning. B is not here. I am both relieved and kind of bummed. We have a new kid and suddenly I don’t feel like the most newbie newbie anymore.

11:30 a.m. This day is going by so slowly, I want to claw my eyes out. A woman made me remake her drink because it didn’t “look like last time.”

4 p.m. Finally out — free! I’m on my way to meet my besties and our friend, E, at a beer garden with live music.

9:30 p.m. Trying to mast again. The fantasy: M and I are at their new apartment, the one they were just moving into when we split up. I get there and immediately want to rip their clothes off, but they want to talk first. We sit down and talk: I wish I hadn’t been so proud, I wish they had been more sensitive.

But before I go down this rabbit hole, something comes to mind: B. I imagine us at work, when our hands fleetingly touch and we pause. There’s tension. She storms away to the back. Then, I follow in search of syrup or something. We almost bump into each other, and instead of scurrying away awkwardly, she grabs my collar. We step farther back out of sight and she has me pressed against the wall. We look at each other, knew it. Our lips hover centimeters apart, then I gently lick hers and she sighs into my mouth. Her fingertips glide over the bare skin of my stomach and I am already very close. It is the hardest I’ve cum in a long time.


7:12 a.m. I decide to sit in a local coffee shop before work and try to write a little. I find a sunlit table by the window and I’m in writer heaven.

I’m in a flow when the door opens and I look up and B is walking in. What is she doing here?! Did she see me?! Just don’t look up again, she won’t notice. I’m getting back into a flow when I’m interrupted. There she is, pulling out a chair and sitting across from me.

We sit there and talk for half an hour or so. Co-workers, old jobs, school, partners. She does this arching-eyebrow thing that makes me wet. Afterward, she offers to drive me to work. I briefly imagine giving her road head and laugh at the thought. I’ve never thought about giving a man road head.

12 p.m. My shift is short today! I strut out and decide to get a joint from a nearby dispensary and smoke it on my way to the thrift store. It’s been a long week … year.

3:45 p.m. I keep thinking that I need to text B about swapping my shifts before she sends out the schedule for next week, but she usually does it two days from now, so I think I still have time. I text the person covering for me to confirm.

4 p.m. Crap. B just sent out the schedule, with a note that says, “I will not be changing this.” I’m confused and annoyed, so I text her.

8:45 p.m. She finally says that my plan won’t work and asks me to figure out something else. At first I launch into full anger. She’s just being stubborn. Then it really hits me. She’s stressed. I feel both compassion and annoyance. I wonder if I’d be this understanding if I weren’t attracted to her.

10:15 p.m. I’m somehow too tired to mast and too wired to sleep tonight. I ask Google to play ocean sounds, hoping that will help.


11 a.m. Luckily, I have another very short shift today. I sneak a text to B with an alternate plan.

3 p.m. Bestie A meets me at work. We walk a few blocks and she sparks up a joint. She’s my smoking buddy.

5:30 p.m. We’re walking by the river. A asks how my heart is. I tell her how I’ve been missing M, but that I know my relationship with myself is my top priority right now. A has listened to me talk about M with patience and curiosity for months now. She tells me that she’ll completely support me if I decide to reach out, then gently offers the idea that maybe M was a part of my story that is meant to help me grow and move forward.

It’s like she read my mind. This compassion I have for B reminds me of the compassion M had for me. It feels so bittersweet to embrace this idea. Our relationship served its purpose.

9 p.m. B texts back approving my plan. Phew. All good.

10:20 p.m. I draw a tarot card before bed. Six of Cups; one of its meanings is to take what we can from the past, but not live in it.

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The Barista Fantasizing About Sex With Her Boss