sex diaries

The Aspiring Cool Best Friend With Benefits

Once a week, Daily Intel takes a peek at what your friends and neighbors are doing behind doors left slightly ajar. Today, the Aspiring Cool Best Friend With Benefits: female, 25, producer, Hell’s Kitchen, straight, single.

12:15 a.m.: Come home to my apartment with Pseudo Boyfriend. He’s my best friend of one year, best friend with benefits of six months. He recently said that he thinks I’m in love with him and he’s not feeling that — he enjoys random hookups too much to settle down with anyone right now. I laughed it off — I’ve had my random hookups too! But I think he may be right.
12:20 a.m.: On my couch smoking and talking. We’re a little buzzed from three drinks chugged at a too crowded club in midtown.
12:34 a.m.: My hand slips onto his thigh. A little playful poking turns into him getting me off with his fingers, me giving him a blow job. He seems winded afterward; tells me it was very good.
1:11 a.m.: Leaving, Pseudo says he doesn’t want to see me for three days. He’s got that hard-to-get asshole thing down pat, but he’s also more fun to hook up with and better at it than any guy I’ve ever been with. Such is the appeal of the bad boy.

1:12 a.m.: Open phone and see text from ex. We were together for five years but broke up six months ago because I cheated on him with Pseudo, though he doesn’t know that. (If Pseudo’s a 9 in bed, Ex is a 4. Although Ex is better at postcoital cuddling.) Part of me wants to salvage our relationship: He’s good to me, good for me, family loves him. The rest wants to move the hell on. He’s mad that I went out with Pseudo tonight. We’re all in the same circle of friends; Ex thinks Pseudo is after me. Don’t respond, go to sleep.

10:19 a.m.: At work, wondering how three drinks equals a hangover. See that Pseudo has signed on to Gchat. I need to work on being harder to get. Don’t message first, don’t message first…
10:20 a.m.: Now Ex is on too. Ugh.
10:21 a.m.: I cave and message Pseudo, “How are you feeling?” I have no self-control.
10:22 a.m.: Ex messages me to say he’s done with my bullshit, is swearing me off for life, and wants his keys back. I tell him to stop being so dramatic.
10:23 a.m.: Pseudo signs off after two one-word messages and no good-bye. Grr.
11:37 a.m.: An e-mail from Pseudo! Rejoice. Exchange a few messages about weekend plans.
1:45 p.m.: Run into former boss while getting off the elevator. I used to have fantasies about him and his (probably faux) mahogany desk. Consider reviving them.
9:54 p.m.: Having drinks with girlfriend, confess to her that I may like Pseudo. I haven’t told anyone that we’re more than friends for fear of my social network self-combusting. She asks how things would change he and I hooked up. I hope I’m a good liar.
11:35 p.m.: Tired, horny. Also feeling guilty about blowing off the ex earlier. But texting/calling will lead to an argument, and breaking out my vibrator will not. Get off, go to sleep.

10:35 a.m.: Pseudo and I are four e-mails deep, discussing plans for tonight/the weekend. He says he’s staying in and watching TV tonight.
11:06 a.m.: Gchat Ex, ask what’s up. He’s particularly unresponsive. Ex says he’s being unresponsive because if I’m friends with Pseudo, he doesn’t want to have anything to do with me. When did guys get so dramatic?
2:55 p.m.: Pseudo Gchats me. Looks like he might be interested in hanging out tonight after all.
9:30 p.m.: Meet up with Ex and friends at bar. Ex and I barely say a word to each other. Text Pseudo to see if he’s up for doing anything. No response.
11:35 p.m.: Back home. Guessing Pseudo passed out in front of the TV hours ago. Contemplate masturbating but too tired. Opt for sleep.

2:10 a.m.: Woken up by cell ringing. It’s Pseudo. Says he smells of sex, drugs, and alcohol. I’m mildly offended and more than a little intrigued — I know Pseudo’s been with other girls since we’ve started hooking up, but it’s been a while since his last fling. Possessive Pseudo girlfriend in me asks if he wants to come over for a drink, he says yes.
2:18 a.m.: Pseudo arrives, indeed reeking of booze, but not so much of sex and drugs. Says his night started out innocently enough with drinks with a co-worker, ended with her molesting him. Does he really think I believe that? Falls into my bed, asks me to take care of him, promptly starts snoring. Loudly.
3:30 a.m.: Unable to sleep through Pseudo’s snoring. Wonder why the hell he came over if he was just going to pass out.
7 a.m.: Hung-over and stumbling, Pseudo leaves. That visit was so not worth losing four hours of sleep.

10:05 a.m.: Get into huge fight with Ex via Gchat. He’s still mad that I’m friends with Pseudo. Thank God he has no way of knowing about last night. Gchat bickering plus lack of sleep equals headache.
12:21 p.m.: Run into ex-boss again. Kind of digging the preppy douche-bag look he’s sporting — pink button-down tucked into designer jeans.
7:10 p.m.: Agree to dinner with Ex to resolve Gchat argument. Half a bottle of wine puts us on much better terms.
7:43 p.m.: Confessing recent hookup activity. He went out with a 28-year-old? I divulge making out with a co-worker and a random dude at a bar but don’t even think about mentioning Pseudo. Ex would probably crack that bottle of wine over my head.
8:06 p.m.: Ex asks to get back together. No. Tell him maybe in the future, but right now, no, no, no.
2:20 a.m.: At a bar with Pseudo and other friends. Ex drunk-texts me: “Wanna fuck?” NO. Make up excuse about having my period and to placate him, say maybe in a few days.
3:17 a.m.: Half-bottle of wine plus mucho beer plus a few rounds of shots leads to me texting Pseudo, “Let’s get out of here and go back to my place.”
3:18 a.m.: Pseudo texts back, “I don’t feel like dealing with you.” WTF is his problem?
3:30 a.m.: Back at my place, alone. Buzzer rings. It’s Pseudo. This guy is such a fucking piece of work.
3:35 a.m.: Wow, he’s wasted too. That explains the antagonistic text.
3:42 a.m.: Pseudo passes out on my couch with beer in hand. Guess I’m not getting any tonight. Pass out in my bed.

1:11 p.m.: Wake up horny. Vaguely remember Pseudo leaving around ten. Thought of using vibrator makes head hurt more.
11:45 p.m.: At a bar with Pseudo and best girlfriend. Ex drunk-texts me again, wants to know what I’m doing. Make up a story that involves Best GF but not Pseudo.
5:17 a.m.: Thanks to an abundance of stimulants, Pseudo, Best GF, and I are at my place, wide awake, drinking, smoking, and talking. Pseudo reveals that he wants his next relationship to have marriage potential (he and his last girlfriend broke up over a year ago). Wonder if he considers our hookup arrangement to have marriage potential.
10:05 a.m.: Hoping Pseudo will stay longer, but he leaves my place shortly after Best GF. I don’t even want sex at this point, just want to lie next to him. Ugh, I really do like this guy.
1:30 p.m.: Ex calls and wakes me up. Says he needs to talk in person. It’s too hard for him to be friends with me while we’re broken up. How does he choose the worst times to start serious relationship talks?
3:20 p.m.: At Ex’s apartment. Tell him to do what he needs to do because I can’t handle the serious relationship conversations anymore. There’s a 90 percent chance he’s going to cave after four days and drunk-text me anyway.
7:49 p.m.: Text Pseudo and tell him about convo with Ex. Pseudo replies that he’s sorry, he hopes I end up getting what I want. What the hell does that mean? I have no idea what I want, clearly.

9:47 a.m.: Initiate the daily e-mail chain with Pseudo by asking how his morning’s going and what he did last night. Is it bad that the best part of work is by far e-mailing back and forth with him?
10:31 a.m.: Pseudo asks how I’m feeling after yesterday’s convo with the Ex. Wonder where the hell this thing with me and Pseudo is going. Is he asking because he wants to know if I’m really through with Ex? Wish I had the balls to confront him, but I don’t want to ruin our arrangement. I’m supposed to be his hot, good-in-bed best friend, not his insecure wannabe girlfriend.
7:48 p.m.: Text Pseudo to see if he’s doing anything tonight. He says he’s still tired from the weekend. Happy that he’s not sexing it up with another girl.
9 p.m.: Running on treadmill watching Rock of Love reruns.
11:54 p.m.: Annoyed that relationship woes have been taken precedence over sex. Take matters into own hands. Check up on a few favorite sex blogs, plug in vibrator. Mission accomplished.

11:21 a.m.: Pseudo e-mails me first.
3:57 p.m.: Ex messages me on Gchat. I ask if he’d be interested in hanging out with our friends this week. He says no — he’s busy at work and wants to hang out with other people. I think he’s trying to make me jealous. It’s working, a little.
9:17 p.m.: The work/gym/TV weekday routine is getting boring. Text Pseudo and ask if he’d be down to do something tomorrow night. He says probably. There’s the motivation I need to hit the treadmill.
10:35 p.m.: Get a text from friend who drunkenly confessed a crush on me a few months ago. He’s sweet, but I’m not interested in another friends-with-benefits situation. He asks if I want to meet him at a bar in Murray Hill. Not tonight, sweetheart, I’m saving my dalliances for tomorrow.

TOTALS: One act of fellatio; one hand job from Pseudo Boyfriend; two acts of masturbation with vibrator; one in person request from Ex to get back together, with refusal; one drunk text request for sex from Ex; one temporary promise of silent treatment from Ex, which lasts 47 hours.

The Aspiring Cool Best Friend With Benefits