sex diaries

The Poet Dating His Much-Younger Former Student

Once a week, Daily Intel looks behind doors left slightly ajar. The Poet Dating His Much-Younger Former Student: male, 31, Manhattan, straight, in an open long-distance relationship.

11 a.m.: Am supposed to edit/critique a client’s writing all day, but first decide to masturbate to pictures of my Grad School Ex’s head Photoshopped onto Neiman Marcus models.
2 p.m.: New girlfriend of two months, a 20-year-old former student of mine who lives in another state, texts to say she liked the porn I sent her last night, and used the big vibrator I gave her, which was risky because she’s home on break, and her room is right next to her mom’s room, and there’s no lock on her door.

2:30 p.m.: I finally climax to a combination of the photos and a video of a German brunette doing things to herself involving rubber tubing. Mad at myself because that’s way too long to spend masturbating when I’ve got work to do. Made the same mistake yesterday, and swore I wouldn’t do it again today.
4 p.m.: Typing up notes on client’s work, and 20-Year-Old texts to say she can come into town next week. She was a student of mine two years ago, and we reconnected on Facebook around the time my Ex broke up with me.
6:30 p.m.: See a woman in high heels crossing the street; jog up half a block so I can be walking right behind her. They’re expensive heels, but she’s wearing them with tight jeans. Skinny blonde in her 30s with a very nice ass.
7 p.m.: Normally get horny in Trader Joe’s because every female employee is a nerdy redhead (exactly my type), but today it is too crowded to concentrate. Very disappointing.
10:30 p.m.: Receive flirty e-mail from Most Recent Ex’s friend. Would love to screw this girl, but don’t respond. Most Recent Ex kicked me out in November — one day she came back from the museum and told me it was over and that she wanted me out of the apartment in two weeks. I was with her two and a half years. But she still owes me money, and I’m afraid friend e-mail might be a trap so she can get mad and not pay me. If e-mail is genuine, will screw friend after I get my money.
11 p.m.: Maggie Gyllenhaal on The Daily Show. Would like to dress her up in twenties period costume and have quick rough anal sex with her in a stairwell with a lot of echo.
4 a.m.: Finally go to bed. Hump my pillow while thinking about big-haired teachers from the eighties.

9 a.m.: Succeed in waking up early and not masturbating, which is difficult because coffee makes me so horny.
6 p.m.: Twenty-Year-Old sending me texts about being my sex toy. Driving me crazy because I didn’t want to risk masturbating for hours and not getting edits done on client’s shitty writing.
11:45 p.m.: Teri Hatcher on Letterman. Think I should move her up into my Celebrity Top Five, but can’t decide whether she should bump out Madonna or Tina Fey. Fey may be more a love fantasy than a sex one, but sometimes it’s hard to tell. Still want to keep Madonna on the list as a matter of principle, but sadly it may be time to transfer her from Current Top Five to All-Time.
12:30 a.m.: Send porn to 20-Year-Old. High-class, artsy stuff. 1 a.m.: Friend of a friend that I had NSA sex with two weeks ago texts to ask where I am. I tell her I’m at home and she doesn’t text back. I still half-suspect that the sex was just the setup for an eventual elaborate prank on me by current roommate, and am waiting for the other shoe to drop.

9 a.m.: Again succeed in waking up early and not masturbating all day. Spend day on my own writing.
9:30 p.m.: Finally post to my website the essay I’d been writing all day about vaginas. Ironically, the process was not at all sexy.
10:15 p.m.: Twenty-Year-Old texts to say the new essay is awesome, and that I’m brilliant, and that she loves it when I dress her up and screw her like a whore.
12:30 a.m.: Twenty-Year-Old texts to say she wants me to send her some extreme degradation porn. I do so. Then we watch the same videos at the same time while masturbating and texting each other. She doesn’t like talking on the phone, which is extremely refreshing in a girlfriend. I pass out before coming.

11 a.m.: Woke up cripplingly horny. Realize I haven’t actually climaxed in three days. Text 20-Year-Old to tell her so, and then masturbate to unfaithful-wife porn while having my coffee.
6 p.m.: Chest/back workout. Hard to work out because new place is so small. Was too depressed to work out for first few weeks, but am getting back into it because I want to be flawless for 20-Year-Old.
11 p.m.: The 20-Year-Old e-mails me 34 pictures she just took of herself posing in lingerie. She tells me she’s never done this for a man before. She is a natural model, extremely lithe and fine-featured. I tell her she should set up a profile on a model networking site and try to get paying gigs. She says she would have to use a fake name. We text back and forth thinking of private-joke fake names.

11:30 a.m.: Jack off quickly to housewife porn in between interviewing potential roommates.
6:45 p.m.: Twenty-Year-Old texts to say she just got red and blonde streaks in her hair. Awesome.
8 p.m.: Twenty-Year-Old texts to say her mom got the two of them a hotel room so they could talk because she is worried about her, probably because of the hair. Twenty-Year-Old is pissed because she wanted to spend the night getting high and watching the porn I sent her. I had been looking forward to that, too.
9 p.m.: Worried that one potential roommate is too sexy, and that I couldn’t manage not to eventually try something if I gave her the room. Current Roommate suggests that I go for it, and then afterward just constantly bring home other chicks until she gets mad and moves out. Current Roommate writes the advice column in a men’s magazine, so I take his suggestions with a grain of salt.
9:15 p.m.: Biceps/triceps workout, to a mix of Madonna and Wagner. I love the erections I get after working out.

10 a.m.: Quickly jack off to interracial secretary porn before people start arriving to view the apartment.
5:45 p.m.: Woman viewing apartment looks like hipster version of Cuddy from House and is wearing stockings and chunky heels and has foot tattoo. I have a boner the whole time. Once again, decide sexy female roommate is bad decision.
6:30 p.m.: Twenty-Year-Old texts to say she gets in at noon tomorrow, and that when it gets dark she wants us to walk around in the Village with her dressed really slutty so people think she’s a hooker. I’m so proud of her.
10 p.m.: Chest/back workout. Normally don’t work out this late, but it feels good to have a reason to push myself.
10:30 p.m.: Twenty-Year-Old texts to say she got dragged to a shitty hometown bar for a friend’s birthday. I tell her she should tease men all night and then tomorrow while I’m screwing her whisper to me about how badly they wanted her and how mad it made them that they couldn’t have her.
10:45 p.m.: Twenty-Year-Old texts to say she’s leaving the bar because she ran into an ex, and that I should send her porn for when she gets home.
11:30 p.m.: I send porn to 20-Year-Old and we both masturbate while texting. It is cartoon porn about maids banging nurses with strap-ons in fifties London. I don’t let myself climax, so I’ll have a lot saved up for her tomorrow. She says she wants to dress up like a businesswoman and play like I’m forcing her.

11:30 a.m.: Twenty-Year-Old texts from the train. She has stolen tan panty hose from her mom so I can tear them open because she will feel more violated that way. As always, she is on the train in a green skirt with no panties.
12:45 p.m.: Grand Central. Dizzy because so much blood has rushed downward. Finally see her. She is wearing four-inch peep-toe platforms. Every time I see her, her body is even more perfect than I remember. We kiss. It’s the first time she’s said “I love you” in person.
1:30 p.m.: I’m naked and 20-Year-Old is going down on me, still fully dressed. I tell her to lay back and I take some pictures. Then I remove her jacket, hike up her skirt, tear open the crotch panel of her pantyhose, and we have sex for about 45 minutes, screaming filth to each other the whole time.
3 p.m.: After a bit of stunned cuddling we both want it again. I go down on her, and like the rest of her, she tastes and smells like chocolate ice-cream cake. We go at it again. She says she wants it even rougher this time, so I’m choking her and slapping her. I start screaming that I love a whore. She screams that I’m right and that she’s a giant whore. I tell her I forgive her for being a whore. She thanks me, and says that she loves being my receptacle.
4:45 p.m.: One last person arrives to view the apartment. It’s a woman, and she’s clearly uncomfortable because 20-Year-Old is strutting around, and both our hair is messed up and we’ve clearly just been screwing.
7:30 p.m.: Twenty-Year-Old says something about a guy she used to sleep with, and something about the way she says it makes me need her immediately. I drag her to the floor and go down on her until she orgasms twice.
10 p.m.: Twenty-Year-Old and I both take bong rips, and she laughs about how it feels more wrong to be smoking weed with her former professor than it does to be having kinky sex with him. Then she sits in my lap at the computer and we watch degradation porn together while I play with her.
10:04 p.m.: She says she needs to have sex right away and I lead her to the mattress. She wants to play like she’s not on birth control and I’m forcing her. She wants me to laugh at her and I do, and she pretends to cry and beg me to stop. I throw her legs over my shoulders, brace my feet against the wall, and start pounding down into her with all my body weight. She’s screaming like I’ve never heard her. Biggest orgasm of the day.
1:30 a.m.: Twenty-Year-Old and I realize we’re both falling asleep on the couch and decide to get up and go to bed for real. She asks if she can wear one of my shirts and I tell her she can and that I want her to bring it with her when she goes home on Saturday. She puts on my big gray sweatshirt and we fall asleep with me holding her.

TOTALS: Seven acts of masturbation; two acts of cunnilingus; one act of fellatio; three acts of intercourse; four suggestive texts or e-mails with other partners; one loving transfer of the boyfriend sweatshirt.

The Poet Dating His Much-Younger Former Student