sex diaries

Sex Diaries: The Office Don Juan With a Taste for Casual Encounters

Once a week, Daily Intel takes a peek at what your friends and neighbors are doing behind doors left slightly ajar. Today, the Office Don Juan With a Taste for Casual Encounters: male, 33, Upper East Side, single, straight, program coordinator.

2:15 a.m.: Awakened in the middle of the night by my Craigette — a Craigslist casual encounter from a few months ago that worked out. We’ve been seeing each other fairly frequently since meeting. It’s starting to get pretty serious, which is as nice as it is unexpected. Her bad dream woke me up.
2:25 a.m.: Consoling Craigette leads to quiet, intense sex.
8:30 a.m. :Alarm clock goes off — I wake to radio chatter about high-class prostitutes.
8:39 a.m.: Alarm clock goes off — I wake to radio chatter about high-class prostitutes.
9:45 a.m.: Taking the train downtown for work. Incredibly crowded. As a man’s crotch sways in my face, and I contemplate whether I would ever be able to go down on a man.
10:05 a.m.: See an e-mail from a former co-worker. I slept with this woman some time back, immediately after she filed for her divorce. She’s coming to New York and wants to know if she needs to make “an appointment.” Not sure what I think about this trip, as I have done nothing to encourage her since our encounter.
11:13 a.m: In a meeting with several colleagues when I realize the woman across the table from me, a woman that I’ve never really contemplated sexually, has a very sheer shirt on. I stare at the outline of her bra. Consider asking if she wants to get a drink after work.
2:23 a.m.: Former co-worker writes again, asking about an appointment. I put her off by asking why she’s coming to New York and where’s she’s staying.
9:25 p.m.: Out with some people from work after a successful event. Craigette sends me a text message asking me to come over.
9:35 p.m.: Craigette calls. I tell her that I’ll give her a call when I get back to the neighborhood, but that it might be late.
2:12 a.m.: I call Craigette, but she doesn’t answer.

9:30 a.m.: Finally wake up. Incredibly hung-over and incredibly horny. When I’m this stricken by the cocktail flu, it hurts my head to masturbate.
9:45 a.m.: Give in to the urge and masturbate, headache be damned.
2:34 p.m.: I receive an e-mail from Craigette asking me to come over when I’m done with work. Her roommate is out of town, a rare treat. I accept.
4:45 p.m.: While presenting at a fairly large meeting at work, I’m overwhelmed by the number of pretty women in the room. I crash and burn — I am absolutely incoherent. The only thing I can think of is the movie Colors when Robert Duvall tells Sean Penn the allegory of the bull running down the hill and fucking one of the cows. “Why don’t we walk down there and fuck them all.”
5:20 p.m.: Bump into a lovely Turkish co-worker in the hall and I tell her about my flame-out in the meeting. She comes back to my office to discuss our current lives. We sustained a yearlong flirtation before finally spending the night together about a year ago. Since then we haven’t seen much of each other in private. During this conversation our old flirtation surfaces as I tell her about Craigette and the fact that she’s a “squirter.” This clearly excites my friend, and before I know what’s happening, I ask my co-worker if she would like to have a threesome with me and Craigette.
5:34 p.m.: I e-mail the Turkish co-worker one word: “seriously.”
5:41 p.m.: She responds: “Give me some time to think about it.”
5:53 p.m.: The Turkish girl writes back again: “No, I cannot do it. Don’t ask me again.”
8:35 p.m.: My co-workers arrive at my apartment after a reception. We drink several bottles of wine over the course of a few hours.
11:15 p.m.: Craigette calls to ask where I am. I tell her that I’m just on my way to her apartment.
11:25 p.m.: I arrive to face a fairly angry Craigette. I try to make it up to her, but I pass out before anything really gets going.

7:50 a.m.: Wake up next to Craigette. She’s no longer angry, and we roll pleasantly around in the bed. After a few minutes of kissing and rolling around, I slide down and perform oral sex on her.
8:30 a.m.: After dozing on and off, we have aggressive, noisy sex.
11:10 a.m.: I’m home and going over these experiences — the Turkish woman and Craigette are swirling through my mind. I masturbate.
10:25 p.m.: Meet an old friend from my hometown at a bar. We talk about how 30 minutes into the meal on a recent bad date, she brought up the fact that she’s got IBS — irritable bowel syndrome.
3 a.m. (I think): Stumble out of the bar with nothing gained but some glowering, defiant stares given in return for my drunken leers.

10:20 a.m.: Wake up late for a meeting in Brooklyn. No time to masturbate despite the desire.
6 p.m.: Surprise that nothing has happened at all to warrant inclusion in this diary.
11:30 p.m.: Go to bed, masturbate while thinking about a 22-year-old Korean-American cocktail waitress I picked up in K-town last year. She spent the weekend with me and we went out on a few dates after our dirty weekend, but there wasn’t really anything in common.

8:30 a.m.: Wake up. Masturbate. Think about my ex-girlfriend of five years and how great her mouth was. Haven’t talked to her since November, and we’ve been broken up for well over a year, so it’s strange that she pops into my mind.
10:20 a.m.: An e-mail arrives from my former co-worker, the one that’s paying a visit to the city soon. She wants to know if it matters where she stays. I break down and say, “Of course not.” I immediately start thinking of last-minute excuses I can deploy to keep from meeting her.
1:10 p.m.: Craigette texts with a request to meet her at Clandestino at 8 p.m. I immediately agree.
8 p.m.: Meet Craigette at the bar. She’s obviously been there for quite some time and is already quite drunk. She gives me a greedy kiss as soon as I sit down next to her, biting my lower lip. Kind of hurts, but …
8:44 p.m.: Craigette slaps me when I admit that I’ve never seen Serpico. She tells me that I can knock her around whenever I feel like she needs it.
10:35 p.m.: Back at my place after spending too much money on too many drinks at the bar. We wrestle each other out of our clothes and fall onto the bed. I am holding Craigette’s hands behind her back while I spank her. After a few minutes of this, I pull her up on her knees, tighten a belt around her neck, and enter her from behind, increasing and decreasing the tension on the belt.
11:05 p.m.: Lying in a very wet bed — she really does gush sometimes — but it’s worth it. Fall asleep perfectly tipsy and exercised.

8 a.m.: Craigette wakes me up by massaging my cock. Once I’m awake, she goes down on me. She squeezes my balls almost too tightly when I come.
8:35 a.m.: I get out of the shower to find Craigette gone and a note — “see you tonight?” We’re spending quite a bit of time together. I text Craigette a “yes.”
12:08 p.m.: Bump into my co-worker that wore the sheer shirt in the meeting from the other day. She looks radiant. I ask her to go to lunch tomorrow, all the while thinking about her red hair and perfect ass.
7:13 p.m.: Craigette texts and asks to come over. I, of course, agree.
7:34 p.m.: She shows up in a short skirt, a little sweater, and very high heels. We chat for a few minutes and then order some food. While I’m on the phone and watching her, she takes off her sweater and lies down on my bed. After I place the order, I strip down and get in bed with her. We have fairly aggressive sex with her skirt pushed up to her waist.
7:50 p.m.: Still kind of winded from our workout when the delivery guy rings the bell. I learn that my buzzer is no longer working, so I throw on clothes and run down four flights of steps.
10:15 p.m.: After rolling around in bed, eating Thai food, and watching The Wire, we fall asleep.

8:30 a.m.: Wake up, reset the alarm and spoon Craigette.
9 a.m.: Wake up late, jump out of bed, and leave her to sleep while I go to work.
Noon: My lunch date arrives, and we go to a small Brazilian place on Eighth Avenue. It’s a lot of fun, but she’s sending out absolutely no sexual energy. Alas, I won’t be getting myself into trouble with her.
7:45 p.m.: Meet Craigette at my corner bar for drinks.

Totals: Four acts of intercourse; two acts of oral sex; four acts of masturbation; one act of showing up two hours late to a very angry Craigette; two morning wake-ups to Spitzer-prostitute talk-radio discussion; one set of avoided e-mails from former fling.

Sex Diaries: The Office Don Juan With a Taste for Casual Encounters