sex diaries

The 52-Year-Old Birthday Girl Flirting With Hot Young Lesbians

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the 52-Year-Old Birthday Girl Flirting With Hot Young Lesbians: female, freelance writer, East Village, 52, straight, single.

6 p.m.: I stroll over to Tompkins Square Park to catch the Dance Parade post party. Run into friends and dance in the rain for a while before we seek shelter in a bar. On the way, I bump into a Drunk Acquaintance who is very excited to see me. He grabs me, hugs me, gives me a big kiss, and slurs to my friends what a “legend” I am and how I’m the coolest chick ever. I invite him to join us, and at the bar he is hanging on me, massaging my shoulders. My muscles have been tense for days so I welcome the semi-drunk massage and encourage him to keep rubbing.

7 p.m.: A Hot Young Lesbian who has somehow become friends with all my friends while I wasn’t paying attention also shows up. I’d met her briefly about a week before and thought she was adorable — and do-able — even though it’s been years since I played for the other team. Given the current climate — my sister’s recent decision to “experiment with her sexuality” and buy real estate with her new lesbian lover, and a close friend moving in with her girlfriend after years of only being with men — I note that it wouldn’t be beyond the realm of possibility. I flirt with her while the Drunk Acquaintance flirts with me … and falls off of his barstool. Twice.
9:30 p.m.: After a bunch of beers at the bar, we decide to move the drinking to my apartment, and everyone comes along, including Drunk Acquaintance. He eventually passes out sitting up, thereby removing any possibility of us hooking up. I let him sleep on the couch, since he lives upstate and is in no condition to drive — or move. My girlfriend and I pass out in my bed. No action with her, either!

10 a.m.: I wake up in bed next to my friend. Wish she was someone I actually wanted in my bed. Or at least someone I wanted to have sex with! She and I pull ourselves together, pick up bagels, and head to a Bloody Mary brunch with a live band that I saw at a party back in April. The Keyboard Player had spent all his offstage time flirting with me, buying me drinks, and bringing me pastries from the buffet. I’m excited and nervous to see him again and wondering if he’ll even recognize me.
12 p.m.: It’s the first of my (many) birthday celebrations, and I’d made reservations through the band’s manager, so it doesn’t completely surprise me when the band sings “Happy Birthday” to me. After the song, the adorable Keyboard Player dude comes over to me, drapes a string of Mardi Gras beads around my neck, and gives me a kiss on the cheek. That’s the most action I’ve gotten in ages! On our way out of the show, I stop to thank the manager, and Keyboard Player walks by just as we’re discussing where we’re all heading next. He doesn’t seem quite as taken with me as he was back in April (and I couldn’t tell if he was being sober and therefore shy or merely no longer interested), so although the band is continuing their afternoon at a Soho restaurant I decide it isn’t a great idea to go chasing after him, and head over to Mars Bar with my friends.

9 a.m.: Wake up in the midst of a wet dream, in which I’d just had an argument with a boyfriend and was locked in a bathroom, with family yelling outside, masturbating. Woke up just as I was climaxing and was actually climaxing in real life. Nice. An orgasm with no hands! I lie there wondering if that’s what Annie Sprinkle means when she talks about “thinking herself off.”
6 p.m.: Showering to dash off to a meet-and-greet happy hour, I feel a little “hmmm” and decide to jerk off. I prop myself against the bathroom sink with my little pocket rocket and get off in a matter of minutes. Not sure if it was in anticipation of meeting up with the Hot Young Lesbian or just giving myself a fresh blush, which seems to make me more appealing in social situations, one of my more recent tricks.
6:30 p.m.: The Hot Young Lesbian shows up and we stroll over to the bar, where there are a few new faces. I meet a guy wearing a very cool custom leather coat, but it’s hot and sticky out, so I assume he’s more interested in looking “cool” than actually being cool. Tool. While talking with a couple of fellow older people, a youngish gentleman is a bit turned off by my co-conversationalist’s cholesterol topic but warms up when I mention my sex diary, admitting that if he were doing one he could set an auto-write program to say “jerked off” every hour. I tell him that would be, what, over seventeen episodes of self-abuse, which seems excessive. We laugh about this, and I decide that it qualifies as flirtation. I mean, c’mon, talking with a stranger about jerking off? That counts, right?
8:30 p.m.: The Hot Young Lesbian and I get out of there and decide to continue our evening elsewhere, stopping at the roast beef joint, then eating our sandwiches at an old school Polish bar and finally ending up at my local watering hole. Even after a bunch of beers I don’t have the nerve — or the vibe — I’d need to hit on the Hot Young Lesbian. The goodnight hug is nice, though.
10:30 p.m.: On my way home I read an e-mail from my “pantie friend,” a lingerie fetishist I met on OkCupid but have never met in person. He says to meet him for a drink. I say I’m already out and ask where he is. “44th St.,” he answers, which is way out of my way. I tell him I’ve been drinking since 7 and that I’m on my way home. We continue our usual pantie banter until I pass out in bed.

8:30 a.m.: Read last night’s final e-mail. “Must be juicy,” he’d sent, meaning my underwear. I laugh and respond: “Juiced, yes. Juicy, not so much!” Check OkCupid and find a new message: “I am (insert high percentage point here) sure I saw you and made eye contact with a smirk on my face last Thursday or Friday, I had a bouquet of flowers it was 1st and 5th street and the cops had just razzed me, so the smirk was a combo of them and my fixation on your body….hello.” Hmmm, that’s pretty amazing, I think, and respond: “Hah! I actually recall seeing you! I wondered who you were taking the flowers to, thinking she was a lucky woman!” I’m flattered that the guy not only was fixated on my body but that he was able to find me amid the thousands of women on OkCupid and recognize me by my kooky photo!

11 a.m.: I show up at my volunteer gig, happy to see my co-worker. I’ve been kinda crushing on him, mostly because he’s the only new single guy I’ve been spending any significant time with. Also working with Travel Buddy, a guy I met on OkCupid. I was initially interested in (or should I say intrigued by) him because he looked so much like my ex-husband. When I met him he was way too creepily similar to my ex-husband in personality as well as looks. There was no way that was gonna work! We’ve become friends, though, and traveled together to Alaska, where we got smashed at his favorite strip club, the Great Alaskan Bush Company. He’s asked a few times if I’d want to have sex. Men — they’re ever hopeful! I wish it were as easy for me to just get drunk and screw whomever is handy as it used to be. Anyway, back to Co-worker Crush. We enjoy each other’s company, but it’s been so long (over a year) since I’ve hooked up with anyone I can’t tell if he’s even vaguely interested. I spend the day wondering whether he’d be a good kisser or not. He sure is tall 

8 p.m.: Sitting at a bar, waiting to meet a friend, I notice a handsome salt-and-pepper-haired man and give him a few meaningful glances. He seems nonplussed and leaves after he finishes his beer. My friend and I go to my sister’s housewarming party. A guy I had sex with in 1987 (now happily married with two kids and living in the ‘burbs) shows up and tells me how great I look. He has a friend who I clock as being single, but he doesn’t appear terribly interested. I wind up having the most fun with a short, gay Asian guy. Sigh.
12:30 a.m.: I get a “Happy Birthday to you!” text from my ex-boyfriend. Though it’s been over a year since our breakup, even seeing his name upsets me. I fall apart and call a friend in California to talk me down from the ledge.

8:30 a.m.: I had planned to wake up and give myself a birthday orgasm but am still feeling wrecked over the ex’s text. Instead I roll over and sleep a few more hours. Waking up a second time I briefly consider masturbating but can’t be bothered. Celebrate my 52nd birthday with a two-Bloody-Mary lunch and a three-hour-long drive to the Catskills, during which I drink a six-pack while my friends throw me a party in the back of the minivan.
11:45 p.m.: We arrive at the campground and meet our fellow campers, a few of whom appear to be available. I flirt with the two who look most appealing — and the most game. I complain about the pinched nerve in my neck that’s been causing me pain in my shoulder and down my arm and Game Guy No. 1 offers me a massage. He spends a good half-hour on me, moving my head around, rubbing my shoulders, and massaging my neck. I am so happy to have the pain lessened that it doesn’t even occur to me that he might be interested in rubbing more than my shoulders. I pass out in the back of the minivan.

TOTALS: one flirtation with hot lesbian, one quasi date with hot lesbian, one “pantie friend” date request, one wet dream with hands-free orgasm, one masturbation session with pocket rocket vibrator, one birthday masturbation session thwarted, two nonsexual but possibly flirtatious massages.

Would you like to take part in the glorious tradition that is the New York Magazine sex diaries? Just send an e-mail to with your contact information and why you think you’d make a good diarist. If you’ve got what it takes, we’ll be in touch!

The 52-Year-Old Birthday Girl Flirting With Hot Young Lesbians