sex diaries

The Assistant Going Clubbing With Wealthy Businessmen

Photo: James Gallagher

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, an assistant who’s hiding an ingrown-hair issue from the man she’s seeing: 23, straight, marketing, Fi-Di.


6 a.m. Wake up to my the first alarm. I’m not usually up this early but I’m going to a clinic before work … thanks to a stubborn ingrown hair.

6:15 a.m. Getting ready for the day with my friend R, who’s visiting me from D.C. We’ve been best friends since high school and I’m trying to convince her to move to New York. She’s going through a tough breakup and I think a move would give her a clean break. Plus, I’m selfish and just want to have more of my close friends here.

7:15 a.m. Say good-bye to R at the subway. I miss her already.

8:03 a.m. I get to the clinic three minutes after they open and there’s already an hour wait in front of me. Moments like this remind me that I’m still not used to city life. About four months ago I moved to New York from a tiny coastal North Carolina town, where I lived for a year post-grad. New York was always the goal, though. It’s the center of the universe.

9:15 a.m. Turns out my little ingrown is now a lovely abscess and needs to be lanced. Did I mention it’s on my FUPA? Looks like I’ll be walking around the city with gauze and packing on my crotch. I get a latte on my walk to work as a reward for going under the knife before 10 a.m.

1 p.m. Playing catch-up at work after the holiday break. I’m a marketing assistant and as much as I enjoy the challenge of having a lot on my plate, it’s definitely still an adjustment from my last job. I’m just not entirely sold on the idea of a marketing career. It’s all so capitalist.

My previous job was a digital content specialist for a vacation rental company. Despite how beautiful it was to live on the beach in North Carolina, I was extremely depressed because it was so small and I felt claustrophobic. I definitely want to be in New York.

6:10 p.m. As I’m waiting for the subway, my phone buzzes. It’s a text from S asking about my plans for tomorrow night. I can’t help it — my stomach does a somersault. I met S through a friend of a friend during a night out. When we met, it was one of those eyes-locking, heads-leaned-in moments of instant attraction. He’s tall, dark, handsome, and about 19 years older than me.

6:30 p.m. I meet up with my friend L for happy hour. She’s a few years older than me and has the most hilarious advice when it comes to men. We plan to go clubbing next weekend and she assures me that we won’t be paying for drinks. I decide to respond to S, letting him know that I’m available tomorrow. He wants to meet up for drinks, which of course I agree to.

Sometimes I wonder if part of the reason I’m so into S is because he fits the vision I had for my life in New York. Dressing up, going to clubs I can’t afford, and being the chill, hot girl. He’s already shown me a side of the city that I wouldn’t have seen otherwise.

9 p.m. Home and changing the bandage on my abscess. I forgot that I didn’t eat dinner and almost pass out at the sight of the blood and puss. I eat some crackers to get my blood sugar up and call my mom to tell her about my medical issues. My mom is one of my closest confidantes, but I do have to be a different version of myself when I talk to her. I grew up very Christian — as in, she cried when she found out I lost my virginity rather than waiting for marriage.

I removed religion from my life almost immediately after I left home for college, and then I went in the opposite direction and had a lot of casual sex. My last boyfriend was during my senior year of college. He was a bartender and I never told my parents about him because they don’t drink and would never approve. Needless to say, I don’t tell her about the guys I’m seeing now.

11 p.m. S tells me to pack a bag for tomorrow and asks for nudes. I give him a noncommittal reply because I don’t know how I can have sex with this giant bandage hanging right above my vagina.


8 a.m. I hop in the shower and send S a picture. I’m still not sure about sleeping over but at least I can tease him.

12:30 p.m. Work is dragging on — all I can think about is seeing S tonight. He texts me that he’s been sneaking glances at the picture I sent. Good job, S, this is how you keep getting nudes. He asks for more but sexting from an open floor plan is just too difficult. Trust me, I’ve tried.

7 p.m. I’m home and catching up with my roommate. She went away for a few days to visit her boyfriend and I didn’t realize how much I’d miss her. The apartment feels empty when she’s not here.

10 p.m. Meet S at the same bar where we were introduced. He’s celebrating his last day at his old job and greets me with a shot. I say hi to his friends before he pulls me away. That’s the thing about S: He has these moments when he looks at me and I feel like I’m the only person in the world.

10:20 p.m. I ask S about his new job. His expense account is bigger than my annual salary, jeez. He mentions that he has to go to Miami at the end of the month and offers to fly me down if I can take a couple of days off from work. If it wasn’t only my second month on the job, I’d already be bikini shopping.

12:15 a.m. We club hop and end up at a rooftop in Chelsea. My favorite part about his friends is that they’re all just as enthralled with me as he is. They ask why I didn’t bring my girlfriends out. Sorry guys, but I’m the only one of my friends who’s into wealthy older businessmen.

12:30 a.m. We are *that* annoying couple making out in a corner by the bar. I typically hate PDA but I don’t care when I’m with him. Good kissers are rare and S is incredible. He keeps pulling me closer by the waistband of my miniskirt. It takes everything in me not to ask to go home right then.

1 a.m. The last bar of the night, a hookah lounge. We smoke hookah and dance until we can slip away in an Uber.

1:30 a.m. Dollar pizza is life.

2 a.m. His place is actually clean! The first time I came over, I was appalled at the state of his apartment. The next time we hung out, I may have drunkenly chewed him out for being a 42-year-old who doesn’t have his shit together. I don’t care if you have three places, if you can own a two-bedroom downtown, you can afford a cleaner.

I’m honestly so impressed he took it to heart and actually did something about it. He also shows me the Bluetooth speaker he bought because I mentioned it last time. Men actually listening and acting on what they hear are such a turn-on. We have horny drunk sex — I don’t really explain why I have it, but he says my Band-Aid is no big deal — and then pass out.


7 a.m. Morning sex is my favorite, so I set an early alarm. We cuddle and kiss and talk and I climb on top of him. I’m not typically self-conscious in bed and I know he said it was fine last night … but in the sober light of day, this god-awful Band-Aid is throwing me for a loop. It’s hard to feel sexy with an infected abscess on your pubic bone!

9:15 a.m. I get dressed while S orders an Uber. I decide now is the time to ask about other people. We haven’t been using protection, (I know it’s dumb but we already had the STD talk) and I want to make sure we stay safe. He assures me he isn’t sleeping with anyone else and says he hopes I’m not either.

I’m not on any BC at the moment … I had an IUD removed a few months ago and still need to get a replacement. Thankfully, it’s super hard for S to actually come so pregnancy isn’t really a concern. He’s definitely a pleaser.

10 a.m. The last time I slept over I was late to work because I was too busy orgasming. Thankfully, I’m on time today, with coffee.

2 p.m. Fuck. Forgot I’m supposed to meet up with a guy from Hinge tonight. After this morning, I’ve kind of lost all motivation to see other guys. I hate to put all my eggs in one basket but I also want to see where things go with S.

6 p.m. The clinic doctor checks on my incision and takes out the packing. I look at the ceiling to avoid passing out. And to think I wanted to be a doctor when I started college.

8:30 p.m. Getting dressed for this date that I’m kind of dreading. We’ve already pushed it back and now I’m tired and don’t feel like having to be “on” to meet someone new.

9:30 p.m. I ride two stops on the subway and realize the bar he’s picked is going to take an hour to get to. I text him to let him know I just can’t do it tonight. He’s super understanding and we agree to meet later in the week.


11:30 a.m. Doze for a few hours before finally getting up. My roommate and I are hosting a wine-and-cheese night and haven’t prepared anything …

6 p.m. I’m stressed about getting ready for this wine night in addition to being worried I said something wrong to S since I haven’t heard from him. Fuck feelings.

10:20 p.m. Wine night is a success. I tell the girls about S. The girls are surprised but more inquisitive than anything else. I exaggerate a little for the shock factor and say I want to become a real sugar baby, but to be honest I get feelings too easily for that. They want to know things like how we met, what we do when we hang out, and what he looks like. I show them a stealthy picture I snuck in the elevator of the club. I have to admit, I love being the one with the most vibrant dating life.

12 a.m. My roommate and I stay up late talking. This is the thing I love about her, she’s one of the few people I’m close enough with to actually have these kinds of intense, analytical discussions. She tells me she thinks I’m basing a lot of my identity on my dating life and she’s right. When I first came to the city four months ago, having a lot of options was exciting. At the same time though, meeting and juggling guys can be emotionally exhausting. I need a break and some time to focus on myself.

1 a.m. I smoke a bowl, write in my journal, read some poetry, and fall asleep.


9:30 a.m. I laze in bed for a while and touch myself while thinking of S going down on me. Imaginary S is as quick to make me come as the real version.

11 a.m. I’m stressed that I haven’t heard from S and playing through everything I said in case I fucked up somehow. I smoke a bowl and go for a run along the Hudson.

2:10 p.m. Remember that I’m supposed to go on the rescheduled date with Hinge guy tonight. I text him and explain that I’m taking a step back from dating and focusing on myself. He’s surprisingly chill about it.

10 p.m. Laundry, cooking, and watching the Netflix show, You, with my roommate. This show reminds me why I have trust issues. Can you ever really know someone?

12 a.m. I used to be a bit of a pothead and I still use it as a coping mechanism when I’m stressed. Not to mention, it’s so much easier to fall asleep when you’re baked.


7 a.m. My first alarm goes off but it’s just not happening today. I snooze it and go back to sleep.

8:02 a.m. Up and not ready to start the day. Mondays are so much harder when the weather is gloomy.

9:05 a.m. I read New American Best Friend on the subway in an effort to remain unconcerned with the men who don’t text me. Thank you, Olivia Gatwood, for reminding me I have so much more mental space when I’m not thinking about guys.

11:40 a.m. Attempting to dive into work in an effort to avoid thinking about S. I can’t say it’s working. I formulate a dozen nonchalant texts that I’ll never send.

2:48 p.m. S texts. It’s about damn time and I’m annoyed with just how relieved I am. He asks how my Monday is going and if I’d like to go to dinner before he flies out tomorrow. This Monday just got infinitely brighter.

9 p.m. Bingeing You again and online shopping for lingerie. I feel like I need to step up my game for S since he’s older and seen a lot more.

12 a.m. I fall asleep watching Glee. I don’t know why I never watched it sooner, it’s adorable.


7:20 a.m. I hop in the shower and then actually put on makeup before work for once, in anticipation of my date with S.

9:15 a.m. Walking to work and I feel on top of the world. I’m living in the most amazing city, starting my career, and seeing a hot guy. I’m actually living my best life.

1:01 p.m. A text from S explaining that his flight got canceled and he has to catch an earlier one. Fuck. For some reason, I’m not surprised. He thanks me for understanding and I tell him we’ll just have to make up for it when he comes back. He’s lucky he’s so sexy.

6:15 p.m. Grab hand-pulled noodles with my roommate. She knows I’m disappointed the date didn’t happen. We explore downtown and grab gelato as consolation.

11 p.m. Roommate is at her boyfriend’s and I have the apartment to myself. I call my mom and update her on our no-heat situation (we live in a shithole). I love my mom endlessly but it’s moments like this that I wish I could tell her everything going on in my life, like canceled dates. Oh well.

12:07 a.m. Smoke the last of my weed and wonder if S made it safely. I fall asleep feeling positive, convinced I’m on the way to becoming everything I’ve ever wanted.

Want to submit a sex diary? Email and tell us a little about yourself.

The Assistant Going Clubbing With Wealthy Businessmen