sex diaries

The 24-Year-Old in a Hotel Room With Her Married Co-Worker

Photo-Illustration: James Gallagher

This week, a single woman making plans to mix business with pleasure: 24, donor relations, bisexual, New Jersey.


5:30 a.m. My alarm goes off. I immediately hit the snooze button. I usually build in some time to my morning for this, mostly in case I want to masturbate before work. But I’m way too tired for that this morning, so I roll over in bed.

6:15 a.m. My eyes are finally open. I quickly check my email to see if any work crises happened since last night. I work in donor relations for a university, so any time a displeasing article is published or a crime occurs on campus, we have to do major damage-control to make sure our donors don’t freak out — especially the multi-million-dollar ones. No crazy emails, thank god.

I can hear my mom talking to the dog in the hallway outside my room. I live with my mom and my grandma too. We’re a pretty close-knit bunch and basically function as roommates, so it works for me. At the moment, I’m saving up to buy a condo of my own.

7:30 a.m. Dressed and ready to head out the door. I make sure I grab the Tupperware containers I packed for lunch today. They’re mostly for my work husband, T. He works in our department; technically, I’m senior to him (I approve his vacation time).

T is a former Big 10 college football player, married with two kids. The moment I met T in my second job interview, I thought he was hot. He’s tall, with dark curly hair and a great smile. You’d never guess he was a day over 35, even though he’s actually almost 44.

T and I barely talked when I first arrived. It wasn’t until I’d worked here for about six weeks that we had a real conversation and realized we had the same sense of humor and, more importantly, the same insatiable sex drive. After that, things heated up pretty quickly. He asked to see nudes, which turned into phone sex when his wife went out of town for work, which turned into hooking up in his car or a random stairwell on campus. Now we’re sort of inseparable — he calls me regularly just to check in, even if we spend the day together at work. He sends me music and articles and makes coffee for me sometimes.

9 a.m. My best friend from high school checks in to see if we’re still on for tonight. Today’s my happy-hour day. I confirm our taco date for this evening.

12 p.m. I get a text from L, the girl I just started seeing. She’s the first girl I’ve ever actually dated — though I’ve hooked up with girls before — and I think it’s going well so far. She asks if I want to go with her and her friends to a drag-kings show. I tell her I can’t make it because I’m supposed to put up my Christmas tree with my mom, but that I want us to go on another date soon.

While I like hooking up with girls, for me personally there’s nothing like sex with a guy. I definitely lean that way much more. Plus, at the moment, I’m focusing on my career and getting promoted. I’m not really out searching for a serious relationship, partly due to that, and partly because I like having options and not being tied down to just one person. I’m not opposed to getting into a relationship with the right person, though. We’ll see what happens with L.

2 p.m. I’m settling into my afternoon slump when T asks me to go for a walk with him. We do this often. We do a lap around the quad and I show him the nudes I took last night. He suggests we try hooking up in his car tonight if the parking lot is empty enough. I tell him yes, and he feels me up as we take the elevator back up to our office.

My sex drive has been like this since I started having sex, which was when I was 19. It played a role in my only long-term relationship (three years with the guy I lost my virginity to), because we would go a while without doing it, and that became an issue for me. It was actually part of the reason I broke up with him.

5 p.m. I purposely leave five minutes after T and meet him at his car. He’s always afraid we’re going to get caught, so we try to not to leave the office together. He fingers me until I come, which doesn’t take very long since I didn’t masturbate last night or this morning. I go down on him after I orgasm. I love going down on him because he appreciates it so much.

He doesn’t discuss his wife and kids with me, but he’s told me he hasn’t had sex in over a year, which baffles me. I like that he doesn’t speak badly about her. I certainly don’t want him to leave her — I think of our relationship as a fun little dalliance with no strings attached. On top of our sexual chemistry, we are legitimately friends and enjoy spending time together. I’m pretty sure that if/when things end between us, it’ll just be because one of us gets a new job and we go our separate ways. I’d be fine with that.

6:30 p.m. I meet my friend at the restaurant and make it in time for happy-hour margaritas. She complains to me about her boyfriend of two years — he’s pressuring her into marriage, doesn’t have a job, and can’t keep an erection. It’s times like this when I’m relieved to be single.

10:30 p.m In bed. I use my vibrator and come hard thinking about T.

Even though we hook up regularly, I don’t really worry T’s wife will find out since he’s so incredibly unassuming. He’s the type of guy who seems like he would never do something like this. The fact that he’s married isn’t ideal, but I’m not sure if I feel bad about what we’re doing since apparently sex isn’t a priority (or even an afterthought) for his wife. Sometimes I wonder if she would even actually care if she did find out. The first time I went down on him, he said he couldn’t even remember the last time it had happened.

One thing is that T and I have never had sex, though we talk about doing it a lot (like when we discuss our fantasies or when we have phone sex). I don’t think it’s out of the question, I just think he’s still getting used to the situation. He has mentioned that he does feel bad about what we do sometimes.


6:30 a.m. I hit snooze too many times. I want to masturbate before work but there’s no time.

12 p.m. Slow day at the office. T and I eat more leftovers for lunch.

1 p.m. T asks me to go for a walk. The main reason we do this is so we can get away from the office and speak freely. I tell him that I’m going to a concert on Tuesday night and considering getting a hotel close by so I don’t have to worry about driving. I live about 30 minutes from where I work and the downtown area, which is where the concert is. I let T know that he’s welcome to stop by the hotel if he can. We discuss a possible morning tryst next week, and I confirm a hotel within walking distance.

5 p.m. The rest of the afternoon at work is quiet. I leave the office and call T on the walk to my car. He left about 15 minutes before me. We discuss my dating life and a few guys who have been texting me but I’ve been rejecting. It’s nice to get his input sometimes, even though I’m not sure how he would feel if I ever started dating someone seriously.

6 p.m. I meet my mom at an Italian restaurant for dinner. We order mozzarella sticks and talk about our jobs and life in general. She’s one of my best friends, and it’s nice to hang out with her. Even though we live together, we don’t always get to talk and catch up — I really like to get dinner with her at least once a week.

10:30 p.m. I’m exhausted from this week, so I get in bed and masturbate. I have two amazing vibrators that always get the job done.


8:30 a.m. Time to wake up. Even though it’s Saturday, I have a busy day ahead of me.

10 a.m. I head to my medical spa for a follow-up appointment from a fat-freezing treatment I got a couple months ago. I’m very into small enhancement procedures. I make an appointment for another round of treatment at the end of the month.

12 p.m. My monthly pedicure appointment. I’ve been going to the same technician for almost three years, and we vent to each other about everything. I tell her about what’s going on with T, and she tells me about her recent hookup with her ex.

9:30 p.m. Sit on my couch for a while, then catch up on more work while watching movies.

12 a.m. Bed. Masturbate thinking about T again.


12 p.m. I love Sundays because I can sleep in. No one at the house is home, so I hang out in bed and use my vibrators.

1 p.m. Make my French press coffee, throw in some laundry, wash my makeup brushes, go to the grocery store, and grab a quick bite to eat with my mom. Sundays are the day I spend getting ready for the week ahead, and this week is shaping up to be crazy busy.

3 p.m. Text throughout the day with L. She’s super sweet, and I really need to see her again.

5 p.m. Do some meal prep for the week. Turkey, roasted potatoes, grilled asparagus, stuffing and gravy — all of which I’m sure I’ll share with T.

9:30 p.m. Get into bed early. Read some Sylvia Plath before I masturbate and fall asleep. I can’t wait to see T in the morning. I always miss him by the time Sunday night rolls around.


8:30 a.m. Arrive at work. T looks amazing.

1 p.m. I’m swamped at work preparing for a committee meeting this weekend. L texts me throughout the day — about nothing substantial, really.

4:45 p.m. I decide to head out when T is leaving because the weather is shitty. He insists on waiting for me to walk out, and he feels me up in the elevator before we part ways.

6 p.m. Target run. I pick up condoms, just in case.

7 p.m. Monthly HydraFacial. They’re expensive at almost $200 a pop, but they are so worth it. I don’t mind splurging on this sort of thing.

11 p.m. Bedtime.


5:15 a.m. My alarm goes off. I set it earlier than normal today because I need to finish getting my overnight bag together.

9:30 a.m. T and I have a plan for tomorrow. The morning after the concert, he’s going to come to the hotel I booked around 8:30 a.m. I’m going to tell our boss that I have a quick morning meeting before I come in (which is true, except it’s actually not until 9:30 a.m.).

I’m glad I packed lingerie, my vibrators, and condoms — even though I’m not sure if we’ll actually have sex.

5 p.m. Check into the hotel, unpack, and quickly get ready.

6:30 p.m. Meet my friend for tacos (third time eating tacos this week) and drinks before the show.

9 p.m. Arrive just in time for the concert. I can’t help but feel a little old compared to all the Gen-Z kids sitting in our section.

10:45 p.m. My friend heads out early because he has a long drive. I order an Uber but the app says the driver is over 20 minutes away, so I walk over to the taco joint for a quick drink while I wait. As I sip my tequila, I get a call from E, a guy who I’ve occasionally slept with for the last two years. A few months ago, we talked about how we were both going to the same concert, but that’s all, though we didn’t coordinate any plans or think we were going to see each other at all. But now he’s separated from the group of people he came with and wondering what I’m up to.

We’re both buzzed and it’s been a while since we’ve had sex, so I agree to let him come back to the hotel with me.

12 a.m. We make out in bed and I use my vibrator to get myself going. He’s not the best at foreplay (the sex is usually just okay). His dick is also really big — like so big that it’s almost uncomfortable. I’m on top until I come, and then he takes me from behind until he finishes. After it’s done, I don’t want to cuddle and I secretly hope he leaves right away, but he falls asleep too.


5:15 a.m. I wake up because E is fidgeting. I don’t sleep well with other people, which is why I rarely ever spend the night after sex.

6:15 a.m. E leaves. I have a headache and I’m exhausted, but I roll out of bed and force myself to shower and start getting ready for T’s arrival.

8:15 a.m. T calls me and says he’s on his way. I tell him the room number and throw on a sexy black slip.

8:30 a.m. T knocks at the door. I let him in and we have a hot make out session. He’s a really good kisser. He continues down my body and goes down on me until I come. Twice. The whole thing feels way better than the sex last night. I go down on him and he finishes in minutes.

10 a.m. Arrive at the office. T and I act like nothing happened. We’re good at it by this point.

2 p.m. Exhaustion hits. The lack of sleep and my multiple orgasms are finally catching up to me.

6 p.m. Meet my mom for pizza. I’m in need of a good meal and a gossip session with her. Still, I don’t tell my mom everything. She knows about most people in my life, but not all the dirty details.

8 p.m. Texting with L. She apologizes for being MIA lately. She’s getting her Ph.D. in psychology and she’s in the thick of finals. I tell her it’s totally fine and that I’ll take her out to celebrate when she finishes up with her work.

10 p.m. Get in bed. As exhausted as I am, I can’t stop thinking about how good my hookup with T was this morning, so I use my vibrator and finish quickly before I fall into a deep, deep sleep.

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The 24-Year-Old in a Hotel Room With Her Married Co-Worker