sex diaries

The ‘Funemployed’ Williamsburger Using OkCupid

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the “Funemployed” Williamsburger Using OkCupid: Female, 28, “funemployed,” Williamsburg, straight, single.


9 a.m. This is the first day I’ve slept in. Ever since I returned from my three-week solo trip to Europe, I’ve been waking up at 4 a.m. I hunker down and job hunt — I quit my data analytics job right before I left. They’d moved me to another department where I wasn’t doing so much data analytics so I decided to quit and travel for awhile.

9:45 a.m. I confirm another OkCupid date for tomorrow with OkC guy #1. He suggests meeting at his friend’s birthday party. Odd choice, but whatever. I’ve been unusually popular on OkC since my return; I’ve done virtually nothing different and yet have gone on dates almost every day. Being unemployed sucks, and as my friend puts it, I’m trying to screw the boredom away.

10:15 a.m. I get an IM from Young Woody Allen (YWA), a guy I hooked up with on my trip who lives in Portugal. We talk about twice a day, every day, about anything and everything. I don’t make a habit of keeping in contact with one-nighters, but he’s adorable, all lips, all wit, and the sex was toe-curling, scream at the top of your lungs good. But, he’s actually based in New York and will return by year’s end.

7 p.m. Meet Young Photographer (YP) at Brisketlab. He’s only two years younger, but I’m so used to dating older guys. Things have been going well and I really like being with him. I’ve seen him three times this week alone. We also met on OkC.

9:30 p.m. The event was amazing and we’re stuffed to the brim. YP met two of my friends tonight — everyone was chatty so I take it as a good sign. YP wants to go back to my place since I live by myself and he has roommates.

10 p.m. YP heads to my couch, and I turn on the TV. I don’t know why I did this. He takes the remote away from me and kisses me deeply. I straddle him and we start making out. He has thin lips but they feel so full when we kiss. We take off each other’s clothes and make a dash for my bed. I’m on top, I’m on the side, I’m everywhere. I love it on the side because it feels more intimate than from behind. It’s all the tangled legs, and reaching back to touch his face while his arms are around me, at my waist and fondling my chest. He gets on top of me and pushes both my knees to my chest. He’s quiet when he comes. I ask him to be a little louder next time.

11:30 p.m. I take a water break. He follows me into the kitchen, takes my glass and puts it down. He caresses my neck and kisses the other side. Then he pulls my leg up to his waist and we go at it again. He turns me around, bends me over the kitchen counter and we do it from behind. Best. Water. Break. Ever.                                                                                                                                

Midnight We’re back in bed, cuddling, and are oddly chatty. High school stories, exes, tickling is involved. I run my fingers over his stomach, and then gently play with him. He gets hard pretty quickly and asks me to go down on him and I oblige. I haven’t given head in ages. It’s partly because I hate when guys lay back with their hands behind their head all smug. Weird power play I usually don’t want to engage in. YP pulls me up and flips me around. We end up doing 69 but he stops to focus on me until I come. Then we do it from behind. He comes again, a little louder this time, and I can feel his breath and moans on my neck. Love it.

12:45 a.m. We fall asleep huddled together with limbs intertwined. Most of the time, I can’t sleep with someone draped on me. With him though, it works.


8:25 a.m. YP wakes up and is frisky. Inquires if I think we can manage sex in five minutes before he leaves for work. We fool around for much longer but he doesn’t come. I give him an extra toothbrush and recoil in terror mentally as to how this could be interpreted. As he leaves, he gives me a long hug and we just stand there locked in embrace for a while.

10:20 a.m. Am IM-ing with a friend about YP. I like him a lot but I can’t lay out what exactly we have in common that makes this work. It’s just playful and comfortable. We’ve only known each other a couple weeks. I also feel guilty about YWA. Friend says to stop overanalyzing and that no one has asked me to commit. Truth!

11 a.m. Daily IM from YWA. He tells me he’s coming back to the U.S. for a couple weeks and wants to stay with me a couple days. I hurriedly say yes. All I can think about is him pinning me to the wall and having his way with me. And taking lots of baths. And cooking together. I’m far more excited about seeing him again than I want to be.

12:30 p.m. Get a text from The Grader. The last time we hooked up, he actually, out loud, gave himself a B/B-. I don’t really like The Grader that much, but I have this warped idea that when dating I must have a full deck, just in case. The Grader wants to take me to some party on Friday. I’m kind of holding out Friday for YP but reconsider since I think we need some space to cool off.

9:30 p.m. Meet with OkC Guy #1 at Berry Park. The birthday party is well underway. He talks to me for a few minutes then ditches me to talk to a friend and returns ten minutes later — this repeats for a while. The girl next to me asks me what’s that about. I shrug and tell her I have no idea.

10 p.m. I’m getting annoyed. I’m not that interested in him, but this is just rude. He’s made no effort to carry a conversation with me nor made any effort to introduce me to people. He hasn’t even feigned an offer to get me a drink. I don’t need a guy to pay for my drinks but make a gesture at least, so I can shoot it down!

10:15 p.m. I’m over it. The girl next to me is sympathetic, and we exchange numbers. She encourages me to text YP or The Grader to finish out the night. I go to find OkC guy and tell him I don’t think this was a great idea. He answers, “Yeah I’m just going to get progressively drunk.” Where’s the social etiquette? Why meet me tonight in the first place??

10:20 p.m. I debate heeding the girl’s advice and texting YP/The Grader, but decide against it. Partly because I’m over it so I just want to get home. Partly because I need to spread out my social calendar so I always have something/someone to do.


10 a.m. Daily YWA IM-ing. I inadvertently bring up the bad date from last night. Fail. He asks me not to share these kinds of things. Understandable. Feeling like an ass. Later he says something about flirting with girls and I get a little queasy. I ask him also to refrain from sharing going forward.

7 p.m. Text OkC Guy #2 to confirm tonight. I have a volleyball game but I’m meeting him as soon as it finishes. Another bad idea, perhaps? Meeting someone while all sweaty and gross, in gym gear? Eh. Spandex shorts never fail.

9 p.m. My volleyball game finishes early. Turns out OkC Guy #2 also lives in Williamsburg so I bolt back to the hood.

9:40 p.m. We meet at Extra Fancy. He looks like Justin Timberlake circa curly haired era. Not sure if this is good or bad. He’s extra snarky—amusing, but don’t know if I can deal with 24/7 snark long term.

1:30 a.m. It’s late, and he’s leaving on a trip the next day straight from work, so he resigns himself. He tells me he likes me, in a way that makes me think I’m supposed to appreciate that comment like I passed some test. There’s a quick kiss. I wonder if he’s blowing me off since this is usually when guys try to go home with me.


9 a.m. Wake up feeling good. Start IM-ing a friend about the night before, but stumble upon a wrinkle in the story. Did that kiss last night really happen? Did I make shit up? I remember thinking, “Well that was brief.” But maybe I was pretty buzzed and may have filled in gaps? Guess I’ll have to wait and see upon his return.

1 p.m. More fun yet tortured IM-ing with YWA.

8 p.m. I text The Grader to get out of the party. He still wants to see me after. I don’t really want to, but agree to it.

11:30 p.m. The Grader and I are back are making out on my couch. All I can think is both YP’s and YWA’s lips are so much softer. He runs his fingers over my entire body and it feels nice, but a little forced. He gently breathes on me, I think, to be erotic, but all I can hear is a loud exhale and feel weirded out. He asks for a condom, and slowly penetrates me but there’s really no delayed-pleasure about it at all. I alternate fantasizing about YP and YWA. He comes soon after and declares this must be better than last time. I do not comment.


8 a.m. The Grader lets himself out and I am grateful to have my bed back to myself. Downgrade him on my roster. Snooze in a little more. Nothing big on my agenda today — job hunt as per usual.

11 a.m. YWA tells me he’s coming back to the U.S. sooner than anticipated, as in next week. I am delighted and terrified at the same time. It feels too much like reuniting in a long distance relationship — all that pent up energy and emotion. I dated someone long distance for six years; it brings up unpleasant memories.

10:45.m. I’m at Blind Barber for a friend’s birthday. It went from zero to douche real quick. I hear some guy tell his friend, “Oh my god dude, so many girls.” Almost straight out of a Dane Cook bit.

12:30 a.m. We relocate to Mona’s, and I decide to text YP to see if he’s out. My friend thinks all my dalliances are a feeble attempt to screw away my troubles, with YWA being so far away. Half true.

12:40 a.m. YP just got home to Bed-Stuy but is game to come out. Yes. Done and done.

1:25 a.m. My friend’s friends whom I don’t know are jokingly debating whether I’m being unfair to YWA and YP. They grant him points for making the trek all the way from Bed-Stuy to the city so late. YP walks in right as that comment is made.

2:05 a.m. My friends leave, and we grab another round: whiskey. Bad idea. We down it and grab a cab back to my place.

2:30 a.m. We immediately disrobe in my apartment. We stumble to my bed and I get on top of him again. I ride him for a short while and he rolls me over on my back and goes down on me. He’s a little forceful when he’s rubbing my clit and it kind of hurts, but a little in a good way. I can only get off through oral and I do, but he won’t stop. I try to deflect by stroking him and pushing him back on the bed. I go down on him but he quickly flips me over and goes at me hard. Eventually, I notice the sun come out and I plead with him to stop because I am so tired.


7:30 a.m. We’re snuggling and I manage to doze off briefly; I stir a little so we start making out and he wants to have sex again. I’m not wet enough and we have no lube so he relents. He soon starts up again, and I relent. We end up having sex for a couple hours, alternating between light, accidental sleep and raucous sex.

2 p.m. We finally gather our hungover, dehydrated selves to lunch at BAD Burger. The service is annoyingly slow and we are dying for greasy goodness. He asks me to come see his roommate’s show with him tonight. I’m surprised that he wants to hang out so much and that I’ll be meeting more friends. I’m a little paranoid that all this time together means we will combust in a fiery hell. Decide to not think about it. We loiter lazily for another hour.

7 p.m. Friends gather for another dinner party. This is also how I kill funemployment boredom — a cooking series, if you will (so far, using recipes YWA sends me).  It feels good to just hang out and not think about any guy. Food and sex seem to be all that occupies me these days.

9:45 p.m. YP texts that he’s finally made it to the show but that it’s wrapping up soon. We’re starting to clean up my apartment so I’m a little unsure on time. We text back and forth.

10:30 p.m. It’s kind of late so I decide not to come out. Space is good, I tell myself. I’ve been single for seven years and I’m trying to date a little more seriously but this is going a little quickly.


10:30 a.m. I wake up tired. Having nothing to do but go on drinking dates is kind of exhausting with all that socializing and alcohol. No one likes when I complain like this.

10:35 a.m. YWA again. I am starting to like the reliability of these IM sessions. It’s weird I find myself being open to YWA and YP in more ways than I normally am comfortable with, other than sexual tasks. Still, in accordance with Full Deck Rule, I’ll keep OkC Guy #2 and The Grader around (though I feel guilty about stringing this one along).

10:50 a.m. I fantasize about YWA and revisit our romps in Portugal. It was explosive and caught me entirely off guard how gentle yet dominating he was. We didn’t have YP-level marathons but the sex was playful and amazing.

Noon Decide to give my hoo-ha a rest, plus I’ve still got a dirty kitchen after last night’s festivities. Resign myself to doing nothing and no one today.

TOTALS: two orgasms; seven acts of intercourse; three acts of oral sex; one phantom kiss; one socially inept date; one new girl buddy; countless IM sessions filled with pining and sexual tension.

OkCupid Sex Diary