sex diaries

The Gay Law Clerk Fantasizing About JFK in the White House Pool

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Gay Law Clerk Fantasizing About JFK in the White House Pool: Male, 25, Upper West Side, law student/law clerk, gay, single.


8:16 a.m. I wake up cuddling in bed with K.. Our first date, dinner and drinks in the West Village, was successful. We’re both comfy and tired, and he looks so sexy in my mesh high-school basketball shorts. We make out intensely, and I play with his penis while we dry hump each other. When we’re done, I make him some coffee and run him a shower. He’s off to work.

10:24 a.m. After dozing off contentedly, I wake up again. Glancing at the portrait of J.F.K.. on my bedroom wall, and enticed by Once Upon a Secret, Mimi Alford’s hot memoir, Ich bin ein horny. Have a hot jerk-off session, thinking about Mr. President emerging from the Oval Office in nothing but boat shoes and doing me in the White House pool. Come pretty hard.

11:45 a.m. I meet straight BFF and his lady friend at the Spotted Pig in the West Village for brunch. We start in on mimosas, and our cute, gay waiter is very friendly. “You look like such happy people,” he tells us, as he plies us with free drinks. I don’t mind his obvious flirting. After delicious food and lots of laughter, we leave pretty drunk.

3 p.m. After a mini bar crawl around the Village we end up at the Standard Hotel. Finish our drinks and head back to straight BFF’s in Union Square.

4 p.m. Back at straight BFF’s penthouse apartment, his lady friend and I pour some gin and tonics. I’m getting pretty sleepy. Straight BFF’s young, sexy investment banker roommate is there, hanging out in his sweats and dirty white socks. He’s so cocky, and it’s hot. I want to take him back to his room and have sex with him, with the socks on.

4:35 p.m. I head back to mine to nap. Text K. to see if he wants to come by. He texts back quickly in the affirmative, so I hop into bed wearing just my watch (and a grin).

5:45 p.m. K. arrives. He leaps in and kisses me; we fall onto my bed and start having sex. It’s so good I’m sure the entire building can hear how much fun I’m having. After he comes, we fall asleep in each other’s arms.

8:30 p.m. Head to dinner at El Centro in Hell’s Kitchen with straight BFF and the lady friend. I try to explain the unique species that is the “Hell’s Kitchen gay.” Using examples from Bravo helps me get my point across. We head to a house party in the East Village.

9:45 p.m. At the party. It’s crowded, mostly girls and not-so-cute guys, but there’s lots of booze. And I can’t emphasize how much I enjoy being hit on by women; it makes me feel masculine and sexy. After a bit, my best GF and her redhead friend from Columbia show up. I watch as they hit on dudes.

12:30 a.m. We all get tired of the party and head to Beauty Bar.

3:49 a.m. After a long night of drinking and dancing, I head home; best GF heads out with Ugly Asian Dude.


10:45 a.m. Wake up with raging headache/hangover. Also have messages from best girlfriend. I took all of her stuff along with my coat when I left Beauty Bar last night. Oops. Yes, I did.

11:15 a.m. Greeted at Westville East by best GF: “You took all my stuff, and I had to borrow cash for a subway ride from the guy I had sex with last night.” Well, I guess that’s two rides on him. She tries to act pissed, but I know she’s secretly delighted being able to say this. She says she’s only hooking up with ugly guys from now on, so she doesn’t have to shave her legs, or be nice.

12:15 p.m. Friend of mine who plays a character on Gossip Girl walks into Westville. I stop to say hello, and all the twentysomething women in the place commence trying to figure out who I am. Good luck!

1 p.m. Best GF makes eyes with a hot swarthy guy at the lunch counter, but is too shy to ask for a number. We also can’t tell if he’s actually hot, so I ask the waitress. She answers in the affirmative: he’s her friend, and he is hot. Numbers are exchanged. “If I get laid out of this, I forgive you for taking my stuff,” best GF says.

2:35 p.m. Best GF and I head to the Mercer Street sex toy store Babeland. I buy a prostate massager, lube and a silicone “egg” for masturbatory purposes. Standard Sunday shopping spree. The sales attendant asks if we need anything else. “I think I’m all set, but my friend would love to know her dildo options,” I say. I get punched.

6:13 p.m. K. comes over. We order Chinese food and watch the Oscars in my bed, with lots of kissing and cuddling. Last year I hooked up with one of the nominees and while I’m tempted to share the story, which is quite entertaining, with K., I resist the urge. I still want him to think I’m classy.

12:12 a.m. The combination of MSG and Billy Crystal have exhausted us both. After I give K. Oscar-caliber head, he heads off home and I fall asleep.


9 a.m. Arrive at work. I’m a bit distracted today. Spend lots of time sending sweet, flirty texts back and forth with K.

6 p.m. Arrive at school for three-hour class. Mondays are rough, but thankfully there are more than a few cute guys in my class. Especially Cute Black Dude, who has the most adorable smile. I’d really like to make out with him.

9:53 p.m. In bed, I start getting horny. Flip open my laptop to Eden Gay, my favorite free gay porn site. Browse through the amateur porn vids. There’s something so much hotter about real, vulnerable people having sex. Bust out the prostate massager. It’s my first try, and it doesn’t feel so good at first, but after lots of gentle fumbling and lube, I hit the sweet spot and make a gigantic mess out of my sheets. Good thing tomorrow’s laundry day.


10 a.m. Wake up and hit Equinox Columbus Circle. It’s so easy to go to the gym when you’re surrounded by hot men at all angles. I have a nice view of my favorite personal trainer, an angry-looking German, while I do an hour on the elliptical.

11:15 a.m. Hit the locker room. It’s an okay crowd. I’ve seen better, but there are some hot salt-and-pepper types and a few well-worked-out preppy boys, my favorite. Spend a few minutes in the sauna, hit the shower and head home.

12:45 p.m. Text with my college friend who’s the self-proclaimed Blow Job Queen of our elite undergrad. I tell her about K.. She tells me she has an important dinner with her boyfriend and others tonight, and that she needs to masturbate before so she won’t be distracted the whole time. I advise her on what kind of panties to wear. I love it. Girls are so much nastier/hornier than they usually let on.

4:15 p.m. In Corporations class, G-chat with classmate E. about other classmate Yoga Guy. He’s a Hatha instructor, works for an IP law firm, immaculately dressed. We both think he’s gay. I try to make eye contact with him to see, but he doesn’t bite. He’s too into the lecture. This makes him even hotter.

7:12 Take a break from reading; open up Grindr on my iPhone. Nothing but creepy old dudes. This app is severely overrated.


3:15 p.m. In the middle of a very long, taxing day at work, get a message from K.. Wants to have dinner and watch a movie tomorrow. Hurrah.

4:45 p.m. G-chat with ex-hookup who lives in London now, a lawyer. Used to have threesomes with him and his British journalist boyfriend. I miss them. Ex-hookup says he’s been enjoying the shirtless photos I put up on Facebook. That was my intention!

10:45 p.m. Colleagues and I submit motion; finally get home from work. Would like to jerk off, but I don’t have it in me. Pass out.


8:45 p.m. K. meets me at my apartment, and we head to have Japanese food on the Upper West Side. The restaurant is filled with gay couples, but mostly trolls. I’m very happy with who I’m looking at across the table. I have a few cocktails; we talk about our families, our careers, our goals. We’re getting more and more serious with each date.  We walk home side by side in the rain.

12:34 a.m.Snuggling in bed watching Arrested Development, K. falls asleep. I’ve had some wine on top of my cocktails, and I’m feeling pretty horny. But he won’t wake up to get busy; says he needs to leave early in the morning for work. Grrr.


9:24 a.m. Wake up and K. is gone. Boo. Text him; tell him to have a good day.

10:45 a.m. Head to Pilates at Equinox. My Brazilian instructor, who faintly reminds me of Teresa Heinz Kerry, is being super bitchy and difficult today, but it’s fine, because I work out better when my sex drive is high. (Although through that logic I should be in much, much better shape than I am.)

12:10 p.m. Hit the locker room. Two Adonises on each side of me, one a golden-brown boy with green eyes, black hair and a perfect amount of scruff, the other a Michael Phelps look-alike. I wish I were in a porno right now.

12:38 p.m. Resist urge to beat it in the shower. Go home and beat it standing up in the doorway of my bathroom instead. I like to mix it up. It’s harder to leverage, but worth it. Where’s my mop?

2:45 p.m. Commence three hours in the most sexless place in the universe—the law-school library. My undergrad library was so much better. There was an entire floor for hookups. “Second floor, pussy galore,” as the jocks said.

6 p.m. Arrive at gay-law-student mixer at Stonewall in West Village. My law-school chums are there, and we get pretty drunk. The guys are only okay-looking, and there are a LOT of girls, which is unusual for these events. “There are so many dykes, it’s practically the Netherlands.”

10:30 p.m. Friends and I head to Industry in Hell’s Kitchen. I’m mostly just goofing off, not really looking for any action. Fend off some desperate, fumbling attempts from fancy feminine boys. Not my type.

1:45 a.m.Just when I thought my sights were set solely on K., a gorgeous, preppy stud with piercing dark eyes and tie approaches. He’s a friend of a friend. We hit it off instantly. He tells me he has a boyfriend, but I can’t resist asking for his number. He seems somewhat scandalized, but gives it to me anyway. You never know what the future holds.

3:40 a.m. Bar closing. Offhandedly ask French and Serb dudes I’ve been chatting with if they want to come back to my place. Expect to get rejected, but they say yes. Preppy stud looks really jealous, but doesn’t join us.

4:15 a.m. Crack open beers, play cards on the Serb’s washboard stomach. Clothing comes off, kissing begins, commence threesome. The Serb and the Frenchman give me amazing tandem head; if only the Eurozone countries were this good at working together. Then the Frenchman and I take turns topping the Serb. It’s so hot hearing them both sigh and moan. When I eventually orgasm, it’s pretty fantastic.  I’ve missed threesomes!

5:45 a.m. Doze off with two satiated Euros at my sides. What a week.

Totals: three jerk-off sessions, one blow job, one act of intercourse, one dry hump, one fantasy, one threesome.

The Gay Law Clerk Sex Diary