sex diaries

The Underemployed Ivy Grad With a Rolodex of Options and a Hot New Boyfriend

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Underemployed Ivy Grad With a Rolodex of Options and a Hot New Boyfriend: 28, male, Williamsburg, gay.


7:22 a.m.: Wake up right before my alarm goes off. Still not adjusted to being back at work from vacation. See Adam4Adam still open from last night on my laptop — check in-box, nada. Jerk off thinking about a Latin guy I slept with. Already late for work.

8:36 a.m.: See boy that I slept with a few times and stopped calling on the subway platform with his boyfriend. This is why I hate the Bedford stop. It’s like the walk of shame every morning. Note to self: start wearing sunglasses to work.

11:31 a.m.: Sexy Banker, who I hooked up with on Saturday night, just Gchatted me. Hoping to see him tonight at a gay happy hour I am going to. I think he might be into me.

3:30 p.m.: Terrible day at work. I must find a real job. In need of sexual/romantic distraction. Look at photos of Sexy Banker on Facebook, fantasizing about tonight.

7:57 p.m.: Trying to pace myself at happy hour, which is not so easy. Sexy Banker just texted that he is on his way.

11:35 p.m.: Post-happy-hour dinner includes footsie and hand-holding. We walk to the subway together, make out for a little (I never do this in public), and part ways. Strangely satisfied, go home and straight to bed; no masturbating.


10:37 a.m.: Horny and antsy at work, I e-mail two boys in the neighborhood about getting together after work. I’ve hooked up with both of them several times, and with the two of them together a couple times. Thinking a three-way would be hot.

10:50 a.m.: Stoner Boy IMs me; we had a thing not too long ago. He got attached, I bailed. I consider inviting him over after work but don’t. He’ll just get hurt, and I don’t want to be that much of an asshole.

1:45 p.m.: E-mail Sexy Banker about getting together over the weekend. We agree to meet up at some point.

3:52 p.m.: Stoner Boy IMs me that he just wants to meet up to have sex when I get out of work, no talking. Seeing that neither fuck buddy has responded, I give in, hoping this is not a terrible mistake.

7:17 p.m.: We make it quick. As usual, the sex is average. He is not the most sexually adventurous person and won’t let me top him, which is part of the reason I lost interest. I feel a little bad that I was kind of cold with him, but he was the one who said no talking. “I made dinner plans, so I need to go.” Twenty minutes later, I’m at dinner solo.


7:45 a.m.: For once, not completely hung-over — surf porn for a bit, jerk off to Xtube.

10:30 a.m.: Get an e-mail on my BlackBerry that I have new messages on Adam4Adam. A “smile” from someone with no pic, and a blow-job offer from a guy I have ignored numerous times. Fail.

11:30 a.m.: Sexy Banker messages me on Gchat. I can’t tell whether he is just really friendly or if he is interested. I am definitely intrigued. He’s hot, went to a good school, and seems to have his act together, no emotional hang-ups. Unlike the last two years of losers I have been with.

1:15 p.m.: Get text from Neighborhood Boy, apologizing for bailing yesterday. Plan to get together over the weekend.

1:35 p.m.: Pass an adult video store near work that I didn’t know existed. I find a bunch of midtown suits cruising the back booths. Enter a booth, put in a dollar for 60 seconds of porn. Anonymous BJ from a guy wearing a wedding band. Feeling mildly dirty, I go back to work.

9:48 p.m.: Text Sexy Banker on my way back to city from an off-site meeting. He suggests meeting for a drink, if it’s not too late. It’s not too late.

10:10 p.m.: Have a few drinks. He is friendly but I don’t really get a flirty vibe.

11:50 p.m.: He kisses me good-night — with tongue. Surprised but happy about this. I’m getting a clear message from him. Hope I don’t screw this one up.


7:30 a.m.: Wake up to my cleaning lady ringing the buzzer. Decide not to masturbate for once. Roommate texts to remind me she is out of town for the weekend. I instantly fantasize about having group sex in the apartment.

1:32 p.m.: At a boozy Friday lunch with friends from the office, I text Neighborhood Boy about organizing some group fun on Saturday afternoon. He is available and said he had a few guys he could ask. Seems promising.

4:35 p.m.: Confirm plans for tonight with Sexy Banker. Excited to see him.

12:35 a.m.: Making out and grinding with Sexy Banker at a gay party in Brooklyn. We both have way too many drinks. Best Friend mentions that everyone in Brooklyn now knows we are into each other.

2:10 a.m.: Get to his apartment. We have drunken sex, I don’t orgasm. I can’t decide if this is because I am nervous because I actually like him or because I am drunk.

2:35 a.m.: Start making out again. He is a great kisser. We go at it again, this time I finish and we go to sleep.


9:37 a.m.: Wake up to street noise, can’t go back to sleep, start kissing to wake him up, go down on him, now he is really up. Proceed to have great morning sex, finish together, definitely the best sex we have had so far.

12:31 p.m.: Get back to my apartment and realize I am completely content with last night and this morning’s sexual episodes, and totally forget about hosting afternoon group-sex party. Cancel.

4:40 p.m.: After a boozy brunch in the West Village, discuss with Ex-Boyfriend Turned Friend and Best Friend the pros/cons of Sexy Banker. We decide to buy some coke from a dealer in the city before heading back to Williamsburg.
10:57 p.m.: Over at Ex-Boyfriend Turned Friend’s house, listening to him lament about his breakup while doing bumps.

Midnight: Sexy Banker calls, I meet him at a college friend’s birthday party on the Lower East Side.

1:30 a.m.: Pouring rain, takes forever to get a cab. End up going back to his place and make out a little in cab. We’re quickly in his bed having sex.


10:10 a.m.: Wake up spooning, we kiss a little and just lay in bed and talk. Nice, but strange feeling to be in bed with someone and not want to just find my pants and leave.

10:45 a.m.: Kissing turns into reciprocal oral sex which turns into him topping me for the first time. Glad to know we have options.

8:10 p.m.: On way back to Williamsburg, send Sexy Banker a text, no immediate response. I go for drinks with friends in the neighborhood.

Midnight Wake up to text message from Sexy Banker, he says that he has got a busy week.

12:19 a.m.: Stoner Boy texts me that he wants to come over for a booty call and maybe stay the night. I briefly consider it and decide not to respond.


7:20 a.m.: Check Adam4Adam, no messages worth responding to. Jerk off. Shower.

10:30 a.m.: Talk with girlfriends at work about whether I should contact Sexy Banker today. They say no, I decide to find another distraction.

10:40 a.m.: E-mail Hot Actor/Bartender I met in a sex party awhile back — pretty sure he is not working right now. We always have a good time. He responds and we plan to meet up when I am home from work.

1:56 p.m.: Mom calls and wants to know why I haven’t talked to her all weekend. I almost tell her about my new prospect, but don’t want to jinx it.

6:17 p.m.: At home alone for the first time all week, get text from Sexy Banker asking how my day is going. Glad he contacted me. I was getting nervous.

6:45 p.m.: Hot Actor/Bartender arrives. We have a drink, talk about the bar he works at, and we get down to business. Always great sex with him, sweet guy, absolutely not datable. We lay on my bed and joke about some of the guys we have hooked up with together. NYC can be such a small town.

9:30 p.m.: Dinner with a girlfriend who jokingly gives me a hard time about my sex life. I agree that if things work out with Sexy Banker, I will be monogamous. She laughs.

TOTALS: Three acts of masturbation; six acts of intercourse with two partners; one anonymous porn-booth blow job.

The Underemployed Ivy Grad With a Rolodex of Options and a Hot New Boyfriend