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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 29-year-old businesswoman who parties hard, has a lot of sex, and harbors secret feelings for her ex-boss: single, straight, Gramercy.
DAY ONE
7 a.m. Alarm goes off. Snooze for 45 minutes then race to get ready. Always a struggle.
8 a.m. Standing on the subway platform with a mix of finance bros, hipsters, and homeless people. I take a deep breath, get a big whiff of trash, and think to myself how much I’d love to stay in New York City forever. I hate the monotony of suburbia and literally get panic attacks when I’m home for too long, even though home is on the beaches of California.
I miss my family, but I’m somewhat of the black sheep. Most of my siblings are hippies living in San Fran. Straight-up tree-hugging, no-makeup-wearing, flip-flops-for-life (I don’t even own a pair), composting hippies.
My stepdad is my main dude — he’s kind of like the father I never had. He listens to me bitch about the idiot men in my life and is always there to remind me to wear condoms. I should really listen to him more. My real dad left us when I was young for a fucking flight attendant. How cliché can you get? I blame him for my fucked-up view of men and reckless sexual ways. But also maybe … thanks? It’s been great fun.
6 p.m. Off to meet my friend’s sister, who just moved here. I feel obliged to put on a happy face. But I always hate forced interactions. Of course we have nothing in common and the conversation is driving me to drink more than expected.
7:30 p.m. Drunk texts inevitably ensue. My go-to buddy at the moment is an Israeli in the Columbia MBA program. YES, first cast, and a bite!
8 p.m. Make my way to a bar nearby since the Israeli is still in class. Dirty martini straight up, please. I make small talk with a lesbian couple next to me. Lesbians love me. If I stick around, I could probably go home with them — hooking up with women is definitely on the “fuck it” list. I guzzle my martini down just in time to catch the next express train to Harlem.
9 p.m. My Israeli greets me at the door with a shot of Jameson, then starts undressing me and calling me a slut. I’m instantly wet. He smacks my ass, hard, and throws me onto the bed, coming in right behind me. We scratch and smack each other around while he fucks me hard, almost always from behind. He’s obsessed with my ass, as most men are. He goes down on me for what seems like a lifetime.
DAY TWO
7 a.m. My alarm goes off. I wake up unaware of where I am. Look over to my right and see the Israeli. Damnit, I didn’t make it home. Then I realize I have a work conference downtown. Thank God I had meetings the day before and am in a killer work outfit; no need to go home first. He calls me an Uber after a morning fuck sesh and off I go. I hope I don’t leak through my panties.
8:30 a.m. Still completely hammered, I sleep en route. Coming from 125th, I get a decent snooze in.
10:30 a.m. During a break in the conference I manage to escape to the nearest deli. I order pad Thai and eat it on the corner of 56th and Sixth, clearly winning at life and not giving a fuck .
12 p.m. Conference over, I head home for a two-hour nap.
2 p.m. Meet my ex for coffee. We had a fun but VERY toxic relationship. Always partying, both of us unable to stop — it was like we brought out this crazy party side of each other for the two years we were together. I ended things because I couldn’t keep up that lifestyle and neither could he. As a boyfriend he was very controlling and critical and judgmental … he thought he was God’s gift to the world. Nothing I did was good enough. Happy to be out of that, though we still see each other (the sex is great). The two of us make plans for later, then I head back to the office.
6 p.m. Arrive at my ex’s apartment, where lines are racked, and he bends me over to do one off my ass (his favorite). I then turn around and do a line off his cock (my favorite). I suck him off until he almost comes, then I bend over in front of the window while he thrusts himself in me. I hope people are watching.
8 p.m. Doorbell rings, two bottles of Veuve Clicquot arrive. I love how bougie my ex is.
10 p.m. Snorting lines off his dick until my face is numb. He turns me around and starts eating out my ass before putting in anal beads. I rub my clit while he pulls the beads in and out — I’m about to come and turn to sit on his face to finish myself off.
1 a.m. Still racking lines and still fucking. We are both numb but can’t stop. We’ve done every position in every corner of his apartment at this point but still can’t stop licking, sucking, and fucking. His dick is just so perfect.
3 a.m. We try to sleep.
DAY THREE
8 a.m. Can barely move, but make it to work.
9 a.m. Bacon, egg, and cheese.
11 a.m. Street meat.
4 p.m. Ramen.
7 p.m. Home in bed.
DAY FOUR
12 p.m. Wake up feeling GREAT. Put on my Saturday best (college football jersey, of course) and head out to meet the crew.
3 p.m. Taking bumps in the bathroom; my team just won. Almost go home with a random, but I don’t want to ruin my makeup. It’s only 3 p.m. — I’ll pass. Off to meet the next crew for the later game.
4 p.m. Get to the next bar and see one of my old fuck buddies: He’s single and looking GOOD. Immediately start flirting and he flirts right back, game ON.
10 p.m. Stumble back to his apartment and light up a joint while we cuddle on the couch naked. He’s covered in hair and has piercing green eyes. I get wet while we start making out and he glides two fingers inside me. I’m never good at foreplay — I get too turned on and need a cock in me. I immediately get on top of him and start grinding while he sucks on my tits. He’s a calmer lover than my ex and the Israeli … he’s lucky he’s so hot or I wouldn’t keep fucking him.
11 p.m. Another joint, another beer, and a quickie before bed. Missionary, which puts me right to sleep.
DAY FIVE
9 a.m. Morning fuck sesh — reverse cowgirl, lucky bastard.
10 a.m. Order breakfast en route home, and the food meets me at the door. Shower, nap.
2 p.m. Seamless. Watch some Bravo. Nap.
7 p.m. Seamless. Harry Potter. Ready for another week.
DAY SIX
Noon Mondays are usually a grind day for me at work. Meetings back-to-back. Luckily my fuck buddies are scattered about the city, which means I can always get a free coffee or lunch with a quick text.
6 p.m. Mondays are also usually girls’ nights at jazz clubs in the Village. I always pack an extra pair of underwear because my ex lives down there and depending on how drunk I get, I end up at his place more often than not.
7 p.m. Sounds cliché, but we’re a very close group of four and totally Sex and the City. Clearly, I’m the Samantha. We have a ringleader who gives us all advice about everything (Carrie), and then a self-deprecating, super-serious badass with a morbid sense of humor (Miranda). Finally, the sweetest girl you will ever meet, the Charlotte who just wants to meet a man and start a family. She recently moved in with her BF — she’s one step closer to the dream. We all get a kick out of shocking her with our stories of random sex and awful dates. Tonight is no different.
11 p.m. I go to bed. Only three glasses of wine; nothing crazy to report.
DAY SEVEN
9 a.m. I’m starting to realize that I’m not sure what I’m looking for. I had a seven-year relationship in college and was convinced I’d marry him (so was everyone else). He was perfect, we were perfect, but I started realizing I had never really lived; I had never even been on a first date for fuck’s sake. I broke up with him and he still hates me to this day, as do most of his friends and family.
Shortly after the breakup, I moved to New York to start over. With no job and no friends upon arrival, I severely questioned myself — for about an hour. Then I went out and got drunk and gave myself a huge hug, GO ME. I worked in fashion for a few years but hated the environment so switched to finance. I mean, what else do you do in NYC? Fashion or finance, potato or po-tot-o.
2 p.m. Fighting the urge to grab a midday glass of Champs, my go-to when I’m feeling down.
2:30 p.m. Glass of Champs in hand, now it’s truth time: I’ve been in love with my former boss for two years. In November, he left the company for a better job and since then, we’ve stayed in touch. Our dynamic has always been super flirty and sexual — everyone actually thought we were together or at least one day would be. He’s only a year older so it’s not creepy at all, unlike when I fucked my friend’s boss from Goldman who was 25 years my senior. Oops.
Anyway, my former boss is a total Jersey family man — very close to his extended family, but no wife or kids or anything like that — who loves grilling and has the worst possible taste in travel and décor; the complete opposite of my standard bougie finance bro. You can understand why it’s confusing to me.
5 p.m. Fuck it — I’m asking him to after-work drinks.
7 p.m. Drinking dirty martinis (our favorite) while watching the Jets (his favorite) and thinking about fucking him (my favorite).
9 p.m. Two martinis deep and the drunk talk starts. I tell him how much I care about him and without hesitation he leans in and gives me the MOST perfect kiss. I almost melt off the chair. What is happening to me right now? Butterflies? Feelings? I feel a little sick and not sure what to do. WAY too many emotions. He then makes it worse by telling me he’s always liked me too. I fight every ounce of my being to stop myself from whispering sweet nothings in his ear and taking him home immediately — I can’t do that with people I ACTUALLY care about.
10:30 p.m. Walk him to the PATH train, he gives me another incredible kiss, and I finally feel something other than a need for the next rush.
10:40 p.m. Heading home and my phone vibrates: It’s my buddy on 33rd. I guess I can make a pit stop.
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