sex diaries

The Top 20 Sex Diaries of All Time [Updated]

Once a week, Daily Intelligencer used to peek behind doors left slightly ajar. We’re not doing that anymore. But as one last celebration of this glorious tradition, we have compiled the top twenty Sex Diaries of all time (according to traffic numbers), along with a selected excerpt from each. Enjoy. 

20. The Single Grad Student With an NSA Buddy and a Roommate Dating a Total Loser

Trying to decide which online experience was worse: tonight’s, or the one with the woman who confessed to sleeping with her college professor freshman year, breaking up his marriage and then contemplating killing herself when he broke things off. Decide to quit online dating.

19. The Freelancer in Love With a Junkie and a Good Guy

I need to work. Beg Junkie to leave, but he tells me he won’t be moving out until the weekend. I give him the same 24-hour speech I gave Carl, but unlike Carl, he doesn’t play nice. He pauses the porn and opens a folder with explicit photos of me that he took two years ago, and announces that he will send the images to various blogs if I call the cops to get him out. He’s high. Junkie spends the rest of the day trying to jerk off, manically — he can’t.

18.  Recent College Grad Who’s Never Had a Meaningful Relationship

He says, “Are you on the Pill, because I just came inside you.” I freak out, I am NOT on the pill and I just had sex with my guy friend with two of my girlfriends in the same bed. This is a new low.

17. The College Student Choosing Between Three Men

On our way home, Adam’s best friend tells me that I present a danger to him because he knows his girlfriend wants to sleep with me, and vice versa. He tells me I can sleep in his room tonight if I have to, and that he will wear long pajamas.

16.   Hot Tutor With a Sex-Filled Life (and HPV)

The dog heaves puke on the floor. Mike doesn’t care, so I clean it up. I’m wildly annoyed. When I get back to bed I’m not in the mood to touch him so he turns and farts. I want to kick him.

15. The Nice-Guy Bachelor Who Wants a Girlfriend

Text from a friend asking if I want to move into her new place with her. I most definitely do. Three years ago we dated for a month or two, and have become good friends. She’s cool, makes a lot of money, and has huge tits. After all this time I still kinda want to feel her up.

14. The Disgruntled, Divorced Former Banker Back in School and the Dating Market

No morning wood, just a mild chubby. I think I might be getting some sort of heart disease. I need to go to the doctor — it’s been a while. Isn’t that what they say? That if you don’t wake up with morning wood, it’s a sign of possible heart failure?

13. 18-Year-Old Extensively Cheating on Her Boyfriend

At apartment with Connecticut Boy. Receive a text from Boyfriend saying, “I know you’re out with your friend. Just wanted to say I love you.” I swoon and feel guilty. Connecticut Boy and I make out, but I don’t let it go any further.

12. The Writer Whose Boyfriend Is Doing the Hot-Sex-Then-Fade-Away Maneuver

V hasn’t returned my call. I had chosen to ignore the signs, but now realize he is indeed pulling a fadeaway on me. I am enraged and upset.

11. The Successful Ad Guy Who Uses His iPhone in Ways Steve Jobs Probably Didn’t Intend

 She is already dressed. I try to convince her to stay and she says she needs to wake up early. I try to pull her back to bed and she finally admits, “I just heard you vomit.” Damn.

10.  The Photographer in Love With a Film Guy Who May or May Not Love Her

I make him watch artsy Bardot film. He wants to try anal. I’m still a “back-door virgin.” Luckily I brought lube. He lays me over his lap and slides his fingers in while rubbing my clit. We go for the kill. Ow. No.

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

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.

8. The Young Dominatrix in an Open Relationship

B, the CEO of a bank, likes for me to kick him repeatedly in the testicles. I threaten him with my two pink dildos, Fat Man and Little Boy. Sometimes I’m disturbed by the ease with which I perform acts of such egregious violence. He calls what we do “making love.” $800.

7. The Poet Dating His Much-Younger Former Student

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.

6. That Drunk Female Lawyer [Note: We have no idea why it’s called that.]

Stumble home drunk and wake up my boyfriend, demanding sex. He has a 7:30 a.m. meeting the next morning and is not amused. I loudly masturbate next to him while he tries to fall back asleep.

5. The Sexed-Up Student With Plenty of Surrogates But No Real Thing

There he is, waiting outside, tall and muscular and on mescaline. He scares me a little, but that’s what I like about him. He tells me that he’s now living in a monastery near Gramercy Park, so he can’t bring girls there. Shockingly, this is not the weirdest thing he’s ever told me.

4. The Aging Professor Struggling With His Youthful Girlfriend’s Sex Drive

Choosing pastrami over pussy, am I crazy? I don’t think so. Sex I can have every day of the week, but we only ever go to the deli on Sundays.

3. The Picky, Prowling 23-Year-Old Woman Looking for a Guy Who Knows How to Give Head

Decide to conduct a little psychological experiment to glean insight into the male species using the bar as my laboratory. Whenever one of the guys gets up to order a round of drinks I strike up a conversation with him at the bar by saying (Condition 1) “Just so you know, I think you’re pretty cute.” or (Condition 2) “Just so you know, I think you’re cuter than all of your friends,” which plays to their competitive instincts and I hypothesize will yield to better outcomes. I tell four of the guys the first statement, then four the latter.

2.  The Finance Guy With a Girl (or Two) Every Night

She arrives and gives me a sob story about her boyfriend being unsure he can meet her. Nonetheless, she tells me she has to be “good” for him. She climbs into bed and lets me play with her fake breasts and gives me a blow job.

And the No. 1 Sex Diary of all time 

1. The Ex-Banker Living on Alcohol, Hookups, and Unemployment

He freaks out and asks me to leave. I angrily storm out and the doorman asks me if I was with the twins last night. I say their little brother and he laughs. When I get home, I look him up on Facebook and see that he graduated HIGH SCHOOL in 2009. He is 17 YEARS OLD and it was his parents’ penthouse in the city.

Update: By popular demand, here is comfortablysmug’s diary, which was somehow not even close to cracking this list. 

Back AGAIN on Facebook looking at the Only One’s profile. Her new boyfriend has put up new pictures of them. I can feel my face get hot, even though I know she’s been seeing him. I’m better looking than him, have more friends, and know I make far more money … he’s a freaking graduate student in philosophy. I will never understand or stop wanting her.

The Top 20 Sex Diaries of All Time