sex diaries

The 36-Year-Old Having a Second Adolescence

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 36-year-old start-up exec who likes it rough: female, 36, Cobble Hill, single, straight.


Midnight After many, many years of being contentedly single, I started actively dating a few months ago. I now find myself a 36-year-old woman in the midst of a second adolescence. But I’m in intense therapy, so it’s okay.

1 a.m. Got “dumped” by a guy we’ll call Sex Pal. Sort of. First, I sent a series of texts in the vein of: “Maybe we should just end this anyway?” In return, I got: “Yeah, it’s probably run its course.”

1:30 p.m. A glutton for punishment, I ask him to complete what is basically a satisfaction survey. He says he had fun, but this was his first “sex-centric coupling” (GROAN) and that he’s just not into it. This is obviously bullshit, but it’s also the most interesting thing he’s said to me during the few months we’ve been fucking. I tell him not to lose my number. Winky emoticon.

2 a.m. Persistent dude from OKCreeper texts. I gave this guy my number months ago when I first started online dating and didn’t know better. I usually ignore him, but not tonight. He wants pictures and I don’t do that; I could still marry a senator, or be a senator, one day! But … I do let him FaceTime me while my camera is covered. We masturbate and come. I thank him for his service. I fall asleep. Sex Pal who?

8 a.m. I wake up surprised to feel sad about the Sex Pal situation. I know deep down that it’s (he’s) not a big loss. He just quieted my loneliness.

10 a.m. At the office. I’m an exec at a tiny start-up and it’s all open-plan. There’s no place for me to pout in peace. My therapist always tells me I need to “experience my feelings” and since I’m having an actual emotion, I reach out to him for an impromptu session. He can’t fit me in, though. Instead, I make Monday-night drink plans with an old friend.

9 p.m. My friend and I catch up over two Manhattans apiece. I notice that the cute guy sitting next to her at the bar is someone I matched with on multiple apps. Now, he’s on a hot, just-started-dating date. Brooklyn and the internet, am I right?


1  a.m. In bed, alone, drunk. Answer a call from OKCreeper. He talks very dirty to me while I play with toys.

1  p.m. Therapist texts that he can meet the next day. I know my window of emotional openness has already closed, but I take the appointment anyway. To a single, aimless woman approaching middle age, there’s no such thing as too much navel-gazing. Plus, he’s totally hot. And his job is to listen to me.

8 p.m. It’s cold and rainy and my heat is always broken when the winter weather arrives. I think about how nice it’d be if there were a warm body nearby.

10 p.m. Text from Sex Pal, who, if nothing else, has a warm body: “I think I might be an idiot.” Me: “You miss me already?”

11 p.m. Sex Pal comes over. He fingers me on the stairs up to my apartment.

11:01 p.m. We get into my apartment and he presses me against the door. He always kisses me really hard. He leads me to my bed and we do all the sex. All of it. We are not naturally in sync physically, but, like me, he likes it rough. He pushed my edges at first, but we’ve figured each other out. I’m assuming this was just the bonus tryst.


Midnight Sex Pal and I lie in bed talking. He makes me laugh, occasionally even on purpose. I can feel the spots on my body smart where he’s left marks and it makes me want to go again. Instead, we cuddle. It doesn’t take as much coercion from him as usual: I don’t like to cuddle, but rainy nights do something to me.

4 p.m. Mid-workday therapy. My therapist is young, handsome, and nearly clever enough to deal with me. He hangs on my words — because I pay him to — so obviously I want to sleep with him. I could seriously write an ongoing column on my very cliché therapy experience.

5 p.m. Back to work. I feel good and only minimally judged — a banner session.

8 p.m. Meet friend for Quiet Neighborhood Dinner. When unsupervised, we are idiots. We’ve been friends since we were children, but we’re not heart-to-heart close. We talk about all the things we would do to improve our lives if we were, say, “driven,” or even just “not lazy.” We sketch a screenplay idea on a stack of cocktail napkins. By our fourth round, I’ve lost half the napkins and all of the ambition they represented.

3 a.m. My Uber deposits me home after more drinking, karaoke, and a ~2 a.m. trip to Wo Hop. I pass out with a belly full of beers, lo mein, and regret. I really killed it at karaoke, though.


8 a.m. I get up and work very hard to get cute despite the limited sleep. After work, I’m hanging out with someone I went out with a few times. Things ended because he stopped being into it. Must be sex-/make-out-ready just in case. He’s really cute. And, uh, talented.

3 p.m. We finalize plans. I’ll go to his new apartment and we’ll “figure it out.”

8 p.m. I arrive at his new place. I’m struck by how hot I still find him. We get stoned and catch up and it’s perfectly pleasant. Despite the fact that I knew he had a girlfriend, I only now know for sure that we won’t be getting cozy.

8:30 p.m. Dinner. We talk about life, whom we’ve been dating, the kinds of sex we’ve been having. I’m neither jealous nor disappointed that he is not mine. I silently commend my maturity. But, real talk: I still totally would’ve MO’d with him. He has dimples and is always winking and shit. I’m not made of stone.

10 p.m. We warmly hug good-bye. He’s a great person I would absolutely not have met if not for Tinder. It’s a stretch to think we’ll actually stay friends, but I hope we do. The internet!

DAY FIVE       

3 p.m. I get an email from a guy with whom I’d exchanged scores of mental-/intellectual-submission fantasy emails. My last note to the Pen Pal told him I preferred he not tell his girlfriend about me, but that it was up to him. Open-relationship rules are personal and that was not my call. We plan to meet for the first time.

6 p.m. Regularly scheduled session. I tell my therapist that I am possibly embarking on a sexually intense weekend  between Pen Pal, Sex Pal (who will probably make his way *ahem* in), and a dinner party I’m attending in the remote part of NYC where OKCreeper lives. He tells me to “be careful” and then mutters to himself about his paternal reaction. I find it cute. I should get a new/second therapist.

8 p.m. Pen Pal arrives. We have small talk, wine, and limited time before he has to sneak back home and, presumably, wash me off. At first gently, and then not, his hands and mouth are all over me and we fumble toward my bedroom. He is smart and hot and strong. I could not be more into it.

8:30 p.m. After all the writing back and forth, he knows exactly what I like. He goes down on me for so long that I’m actually excited for him to stop so I can return the favor. When I stop, he flips me over, fucks me from behind, and inserts a toy into my ass. Outstanding. I come and he replaces the toy with himself. As always, the pain is incredible and disorienting at first. He asks me when I last had anal sex. When I say three days before, he tells me I should be better at taking it. I find this both repellent and intensely arousing, and he knows that. As I also find it when he asks, in a whisper, if I want him to stop and I can barely cry no. With the help of a vibrator, I come intensely while he pounds me, and another time while he stands next to the bed watching me. I want his cum on me, but not my new headboard (it’s upholstered, hello). So I get on my knees in front of him and he finishes all over my chest. It is the porniest sex I’ve ever had.

10 p.m. We’re both shaky, but now chatting and hydrating. I walk him out. I assume I won’t see him again, but I’d love to give him a high five. Because whoa.

Day Six

3 a.m. Stupidly tell OKCreeper that I’ll be in his neighborhood in two nights. Nothing like a few drinks to kick up my desperate attention-seeking drive.

1 p.m. Shamefully wake up super-late. Justify depressing behavior by remembering I’m in my sexual peak! That, or a second adolescence. It’s been a weird, but mostly fun few months.

2 p.m. Piece together events of previous night. Lament that intelligent, good lays are all actually unavailable. (Does this lament mean that I want someone to be seriously available for me?) Remember that the sneakiness makes it actually not ideal. Cringe at my part in it. (Does my complicity in the sneakiness mean I actually do just want to have fun?) Cringe, knowing I’d definitely do it again.

11 p.m. Arrive at a friend’s birthday party on the LES. Despite being in Manhattan, it’s excellent. I unintentionally ingest some molly. Decide, then, that I may as well go all-in. I do a bunch more.

Day Seven

1 a.m. Very high. Want to have sex. Text Sex Pal. He professes to want to eat my ass very badly. I tell him to come to the party.

2 a.m. I don’t hear from Sex Pal again. It should be illegal to answer affirmatively to a booty call and then disappear. Especially when the Bat-Signaler is on drugs.

3 a.m. Get chatted up by bearded dullard while smoking. He hits on me, fanned by my drug-induced bravado. “I bet you $100 I’m the smartest person you’ve ever spoken to.” I am a total dick.

3:20 a.m. Heading to Bushwick apartment of Insomniac Guy from a while ago. I don’t remember if the sex was that good, but you know … Gotta eat.

4 a.m. I now remember that Insomniac’s kissing stood to improve.

4:01 a.m. His teeth smack against mine and there’s an unsettling noise. Something’s in my mouth. He is Freaking Out.

4:01:03 a.m. I realize there is a TOOTH RATTLING AROUND IN MY MOUTH and that it is not my tooth. I repeat: IT IS NOT MY TOOTH.

4:01:11 a.m. I’m not sure why, but I lie when asked if there’s anything in my mouth. While he’s in the bathroom I pretend to find it. He retrieves his tooth shard. I am naked and confused and still slightly high.

4:05 a.m. He returns to the bed and we talk small. He’s really nice and I don’t want to exacerbate his embarrassment. I wonder how long is long enough to hang out before running away from the craziest mid-coital event of even my recently freaky sex life. Fifteen minutes, I estimate.

4:20 a.m. I (obviously) avoid kissing him good-bye. I get in an Uber and text every human I know about what has happened. I sleep like a champ.

5 p.m. Long subway ride. The day-after molly doldrums coalesce with an afternoon of running around the city visiting appropriately behaved friends. Cute babies! Enviable marriages! New homes! I switch my iPhone from playing Jeff Buckley to Run the Jewels. Things look up a little. I mean, I know I don’t want those things. Not yet, at least. But, Jeebus. I also don’t want other people’s teeth in my mouth.

5:45 p.m. I’m greeted at dinner by incredible, kind, non-judgy friends. They give me wine and love and support and pasta.

10 p.m. Vow to be a better adult next week. Or at least try harder.

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The 36-Year-Old Having a Second Adolescence