The Lesbian Sommelier Celebrating Her 40th Birthday

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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: female, 39, sommelier, single, gay, Soho.

DAY ONE

9 a.m. I am already dreading tonight. I’m going to watch the Oscars at this girl’s apartment; it’s our second date. She’s not my type but I’m trying to be open-minded.

Noon I’m getting my hair cut and colored in Soho. My date is very sexy and dates beautiful women — or so I’ve deduced from internet stalking. So now I feel a pressure to look as hot as possible, even though I don’t even like her. We met on a flight home from Paris. She’s annoying and pretentious, and I’m exhausted and just want to watch the Oscars alone with some pie. And by pie, I mean pie.

3 p.m. I decide to start drinking to tame the building horror. I’ve pretty much always dated women, and people don’t realize that it’s all the same: Dating sucks. Pussy, cock, whatever.

6 p.m. I show up at her apartment with an amazing Brunello. I work in the wine business and know my shit. She looks sensational. But. So. Much. Perfume.

10 p.m. The Oscars are long and tedious and we are sitting on opposite ends of the couch and it’s awkward and boring and her perfume makes me want to gag.  I say something about a fake spin class the next day at 6 a.m. so that I can leave.

10:30 p.m. Hot make-out good-bye. Just kissing. My work here is done.

DAY TWO

9 a.m. No desire to see sexygrrrl again. That perfume!!!

10 a.m. I go to the office. I’m the sommelier at a popular New York restaurant. Needless to say, my workplace could be a reality show.

Noon Paperwork and inventory-type crap. I’m cranky that I can never get back those five hours from last night.

3 p.m. I think I’m the only single lesbian in the world not on any dating apps. My family has a recognizable last name and even though I’ve been “out” forever, I don’t want to risk any “Page Six” shit. I smoke a joint with the prep staff and take a moment to think about someone who’s been on my mind: Amelia.

3:30 p.m. I text Amelia. She works at a competing restaurant and we get together a few times a year between other failed relationships. On paper, we should be the perfect couple. But there is always something lacking that I can’t put my finger on.

8 p.m. Amelia and I make plans for tomorrow night. We know the drill.

DAY THREE

8 a.m. I masturbate in bed, just using my fingers and imagination. Old-school. I always imagine rough ass-play in my fantasies, and yet zero interest in it IRL.

9 a.m. I go on a ten-mile run.

11 a.m. Amelia’s bringing the wine tonight, so I’m in charge of the cooking. Decide to go for lamb chops and a crisp salad. Steal most of my ingredients from the resto before the chef — that coked-up dick — gets in.

3 p.m. So here’s the deal with Amelia. I think there’s something off in our chemistry. Like a pheromone thing. That is the only way I can explain the reason we’ve never dated seriously. But pheromones can change, can’t they? I feel a little hopeful. With each year, we are both older and wiser, less slutty, more tired. Maybe our sweet spot is now.

8 p.m. Amelia shows up. She looks pretty. I don’t know the right term for her on the butch to femme scale; I’ve never been into that shit. We’re both pretty, fit, and more girlish-looking than boyish.

10 p.m. Dinner is simple and delicious. The wine is smooth and expensive. We end up in bed together.

Midnight The sex is hot. It always is. We eat cunt for days.

DAY FOUR

9 a.m. Amelia is in my bed. It’s comfortable. I get up to brush my teeth and get a little self-conscious about my ass. Is it starting to sag? I turn 40 this week.

9:15 a.m. I confess to Amelia that I feel my ass is sagging. She feels her tits are sagging. We laugh, kiss, tickle, and fall back asleep peacefully. Ah, the sweet beauty of two naked dykes.

3 p.m. Back at work. The loveliness of being with Amelia is already fading. This happens every time: It’s like when you’re watching a great movie that you never want to end, and then the credits roll, you get up, you pee, you get on the subway, and you don’t really need to see that movie again … ?

6 p.m. I browse sperm donors online. I’m constantly debating having a baby. Not sure. I have ten nieces and nephews, all in the area, who generally scratch the itch.

DAY FIVE

8 a.m. Very early breakfast meeting with a dude, Zach, who’s in town from L.A., and who wants to hire me for this massive restaurant project. He knows my brother and has done business with my family, so I assume he knows I’m queer. And yet … is he flirting?

10:30 a.m. I’m not even at the restaurant and Zach texts about checking out a wine bar later. I’d like to hang with this guy; it’s smart professionally and personally, but he needs to know know ASAP that there’s nothing for him here. I text back, “Yes! My ex-girlfriend used to bartend there.” That’s a lie. But he’ll get the point. And probably an erection.

11 a.m. He writes back with a black thumbs-up emoji. (He’s white?) No wonder the fucker is single.

2 p.m. Amelia swings by the resto to say hi. It’s like our romantic ambivalence mirrors each other. The healthiest thing would be to talk it out. I’m just not that into you, and you’re just not that into me … now let’s rub up against each other til we come like crazy.

Midnight I am wasted and having a blast with Zach. It is inevitable that he’s going to try to fuck me. Nothing I can’t handle. I do make out with him a little at the bar. What a huge, wet tongue he has. It’s hotness. But it stops there. I stopped fucking men in college and never, ever, ever looked back. UBER!

DAY SIX

11 a.m. I’m hungry and have the day off. Bacon, egg, cheese, and … sperm donors. This is what I do.

Noon Two of my straight girlfriends recently became Single Mothers by Choice. They are the happiest out of everyone. I text them both about meeting for coffee. Raphaella says she’s around.

1:30 p.m. Raphaella looks like Salma Hayek. She was a patron at my old restaurant, and everyone wanted her. I’m really happy we’re friends. She used to tell me how good sex felt while pregnant — she’s an open book, that one. I tell her I’m getting close to pulling the trigger. She says it’s a no-brainer. Raphaella glows. She shows me baby pictures and a dick pic of her new man. Now, it’s not my expertise, but this guy’s cock is a fucking work of art.

7 p.m. I get into bed. Rub one out to my go-to fantasy: getting rammed in the ass by some sort of candlestick/strap-on mash-up while Heather Graham in her Rollergirl (Boogie Nights) costume licks my pussy dry.

DAY SEVEN

9 a.m. It’s my birthday.

10 a.m. On my walk to work, I get a Nutella croissant. Call it a secret celebration.

Noon So many texts and Facebook notes. It feels really nice. My family has a big dinner planned for me tonight. I can’t wait to see everyone. I plan on telling the gang that this is the year I pursue pregnancy. Maybe it will work, maybe it won’t, but I’m ready to try. I anticipate many tears of joy with this announcement.

5 p.m. I leave work a little early to continue a tradition I’ve had since childhood: one new outfit from Bergdorf. It used to be from my mother to me, but now it’s from me to me. This year, I am very good to me.

7 p.m. I show up at my parents’ place feeling blessed. Yes, dating is hideous. Women are difficult. Soul mates are far and few between. But I love my family, my job, and my new Alexander Wang. And the rest is all TBD!