Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the ‘Mostly Straight’ Woman Jumping From One Male Lover’s Bed to Another’s: female, web editor, Spanish Harlem, 25, mostly straight, casually dating.
7:20 a.m.: Emotionally exhausted. Yesterday did not go as planned. Ex-boyfriend the Teacher flirttexted that he wanted my “sweet ass” in the middle of the day. Met up for date at the Soho Playhouse but had fight after the show. It ended with me crying and him deciding to go home solo. I’m tense and want to masturbate, but too tired.
7:55 a.m.: Text from the Teacher: “I apologize for last night.” Reply that I don’t love his mood swings.
8:20 a.m.: Decide I need to finally meet a girl. Put ad on Craigslist in “women for women” section. It was hot to hook up with girls at sex parties with Teacher but want to date one. After a couple failed attempts at dating girls in college, I stopped trying. I think maybe a girl would be able to give me more of the emotional connection and commitment that I’m seeking.
9:47 a.m.: Text the Photographer I’ve been seeing for a couple of months to confirm plans for tonight. He forgot he was coming over, invites me over instead. Annoyed because am unprepared for a sleepover.
1:14 p.m.: I have to work late and won’t make it home in time to change. Unhappy I’m the one who has to make such an effort. Ask him if he’s free in two days instead. He’s not free for six. Feeling stubborn and reply that I’m not free for four days after that. Only partially true, but I’m feeling unloved and don’t feel like trying.
2:57 p.m.: Teacher asks me to a movie this week. I agree, ask if we can do dinner and have sex beforehand. He’s excited.
3:05 p.m.: Text Photographer that seeing each other once a week is not enough for me. Says his schedule should open up soon.
4:20 p.m.: Text Teacher to see if he’s heard from Actress we had a threesome with at a sex party about tomorrow. I really want to see her again. He replies she wants one-on-one with him this time. Feel jealous. Ask if he’ll do it. Says he’s working on the threesome but yes, he will. Feel more uncomfortable.
8:05 p.m.: Dinner at Taco Chulo. Photographer asks about my fight with Teacher. Try to explain without revealing too much. I prefer honesty but always feel so awkward. Says he’s jealous I’m getting so much action. I point out he has a date tomorrow.
9:44 p.m.: Text from Firefighter I met on OkCupid. We have a first date in a few days, and he wanted to tell me his work troubles tonight. I am not in the mood since we haven’t met yet, so ignore.
10:30 p.m.: At his place. Photographer gets on top, turns me over. He goes down on me. I dislike that I have to stay quiet this time because his roommate is home. He gives me multiple orgasms for the first time. Hooray! I go down on him, and we have sex. I suggest we try the vibrating ring he bought last time. It’s fun but doesn’t do much for either of us.
10:55 p.m.: He finishes, and I don’t, but I was close. We lie in bed cuddling, I grab my vibrator and get myself off again while he strokes my breasts.
11:30 p.m.: Tell him about my Craigslist ad to date a girl. He laughs.
8:45 a.m.: Write back to some of the girls that answered ad. Try not to be too picky.
12:01 p.m.: Feel insecure. Tell friend that last night with Photographer was great but I’m feeling like maybe it’s best to break it off and look for something more. Dating several people is fun but I ultimately want a monogamous, devoted partner. Why is that so hard to find?
6:02 p.m.: Text from Teacher. He’s disappointed Actress said not to kiss when they meet. I remind him it’s their first actual “date.” He says they’ve already had sex. I’m feeling jealous. Both my men have dates tonight and I’m going to a gay drag party. My actual chances of meeting and flirting are pretty slim. Decide to masturbate when I get home.
10:54 p.m.: At Gansevoort Park’s rooftop for Amanda Lepore party. So many sexy people. Too bad they’re all gay men. Would they enjoy me wearing a strap-on? Also: Amanda Lepore is gorgeous.
12:15 a.m.: Tipsy and admiring hot go-go dancer. So turned on.
12:45 a.m.: Too tired to stay out late. Masturbate with favorite vibrator. Think of go-go dancer’s tight abs and cocky smile. Give myself three orgasms. I think I’m done.
8:05 a.m.: Wake up dreading news of what happened on Teacher’s and Photographer’s dates last night. Decide to wait till they offer the information.
9:15 a.m.: Give in to the curiosity and ask Teacher and Photographer how their dates went.
9:25 a.m.: Photographer felt no fireworks. I feel better. Teacher had sex after a long night of Actress playing hard-to-get. I feel worse.
9:47 a.m.: Tell Teacher I’m glad he had fun, but I feel uncomfortable doing future threesomes with Actress. Now it feels like I would be invading something.
11:45 a.m.: Teacher e-mails link to a pansexual kissing party, says we can do this tomorrow instead of movies. Text him that it makes me feel unhappy and unwanted that he wants to turn our one date night into a “let’s make out with random people” night. He replies he wants to spend time with me regardless of what we do. I feel much better knowing that I’m more important than group sex. I still want to go, just not as often. Right now we need alone time. He tells me he’ll get the movie tickets.
12:30 p.m.: Debate how much of a hypocrite I am. I want just one loving devoted boyfriend, but I’m dating two guys and flirting/setting up dates with with several more. Plus a few girls.
2:23 p.m.: Teacher asks if we can have anal tomorrow. I’m still sore from having it twice last week, once with Photographer and then once with Teacher. I enjoy it sometimes, so tell him maybe.
6:27 p.m.: Realize what I miss about how serious Teacher and I were before is that he never says “I miss you” anymore. Text him that. He replies he got movie tickets for tomorrow. Awkwardness.
11:05 p.m.: Want to masturbate. Too tired. Pass out instead.
8:10 a.m.: Shower and shave for Teacher. I don’t really like it, but he loves it and I like to please.
11:07 a.m.: Teacher texts: “Can’t wait to have my tongue between your legs …” I get horny instantly. He suggests bringing the dildo over so he can double penetrate me. Didn’t love it before but feel up for it.
12:45 p.m.: IM from Texas girl I met through CL ad. She wants to chat at night for some “quality time.” I tell her I’m busy. She’s hot but not in NY, so what’s the point?
3:30 p.m.: Conversation with Texas girl is a bit awkward. I wonder if all CL people are nuts.
5:55 p.m.: Greet Teacher wearing fishnet thigh-highs, heels, and a tight black dress and say, “Hope you’re ready.” He responds by pushing me against the wall and kissing me fiercely. Pushes me to my knees, I blow him until he’s hard. He bends me over the kitchen counter and fucks me. I come. He takes the dildo and puts it in my ass. Tells me I’m a pro. I bite his finger. He wants me to come, I tell him I can’t without my toy. He orders me to get it without letting the dildo slip out. I walk to my room holding it in, grab the clit vibe, and join him in the living room. He fucks me again, then takes the dildo out of my ass, takes off its condom and puts on a new one, then switches. I use my vibe and come with the dildo in me and Teacher in my ass. He goes to wash off, comes back and jerks off while I finger him and lick his balls. He finishes. I complain I didn’t get any tongue. He immediately throws me on the bed and goes down on me. I come.
10:30 p.m.: Back home after the movies, cuddling and watching TV in bed.
9:30 a.m.: Make plans with Photographer for tonight.
12:22 p.m.: IM with Texas girl again; she really seems clingy. Tells me “see you when I see you.” Ugh.
1:26 p.m.: Photographer cancels plan, has to work at 5 a.m.
1:40 p.m.: Text Teacher if I can come over later tonight.
1:58 p.m.: Super horny. Feeling like I want to tie someone up and sit on their face. Decide on Photographer.
8:00 p.m.: Cat gets really sick, tell Fireman I can’t make it. He freaks and calls me a liar. I call him crazy.
1:46 a.m.: Masturbate with my clit vibe again. Five orgasms. Pass out.
8:21 a.m.: Text from Teacher. Says I can come over now. Lie in bed contemplating.
8:38 a.m.: Decide to go. It’s pathetic what a girl will do for good sex.
11:14 a.m.: Cuddle and talk with Teacher.
12:55 p.m.: I blow him, he turns me over and fucks me. Tells me to touch myself with both hands then turns me over again, and we have sex missionary, then from the side. Tell him I won’t come without oral. He goes down on me. Have amazing orgasm.
2:35 p.m.: Photographer texts he can’t come over tonight because wants to rest.
2:45 p.m.: Friend calls and cancels dinner plans.
3:15 p.m.: Call Teacher. Don’t want to be alone right now after all my plans for today got canceled. He says he wants to be solo. Go home and cry. WTF is wrong with me?
3:35 p.m.: Text Teacher about the crying, he insists I come over.
4:35 p.m.: Teacher puts finger in my mouth. I bite it; I know he likes that. Pulls me over and I blow him, then he fucks me doggy style.
4:41 p.m.: I like our random quickies sometimes. Neither of us came, it was just for fun.
6:17 p.m.: Go to kitchen because of smell of popcorn, just in bra. Teacher tells me if I’m going to be naked, to just be naked. Take my bra off. Tell him I have to leave, which has the positive effect I wanted. He tells me to get on my knees. I blow him. After, he bends me over the chair, fucks me. Then he lays me on the table and fucks me again.
6:30 p.m.: Back in his bedroom. Tell him I think I’m finally ready to be tied up. He messages a married friend I’ve played with a bit at parties who’s an S&M expert. Excited for when this happens in the future. Maybe his wife will join.
9:05 p.m.: Meet up with Photographer at Barcade. He changed his mind about resting but I had to come to his area again. Ugh.
10:05 p.m.: He’s drunk and talking about how he’s still in love with his ex. I feel like we’re breaking up. We talk about how there’s something missing. Although I like him, I don’t really have feelings for him either, but we agree it’s really fun to hang out.
11ish p.m.: Getting more drunk at Post Office Bar. Feeling ballsy, I give my card to the waiter as we leave. Photographer can’t believe I just did that.
12ish a.m.: Drunken sex. I don’t remember much, except that I didn’t come and was angry about it.
9:08 a.m.: Wake up, surprisingly not hung-over despite blacking out. No more drinking, though.
10:15 a.m.: Part with Photographer at the train station, kiss goodbye. Guess I’ll be seeing him again.
11:05 a.m.: Go straight to Teacher’s house and cuddle. He tells me about fucking a student’s mom last night; I tell him that somehow I wanted a boyfriend but ended up with another lover instead. We talk about whether him ramping up dating girls again is going to cause problems. We’re not as emotionally close anymore, so I hope not.
2:30 p.m.: After shower, have lunch and watch TV. He pulls me over and I blow him, then ride him. Blow him again. There’s a lot since he hasn’t come the past few days. Ha.
11:00 p.m.: Back at Teacher’s place. Been seeing him a lot this week, almost feels like what it was when we were still seriously dating. But this is just casual. Try not to think about it, just watch True Blood.
12:15 a.m.: He turns me over. I say I’m sore and need foreplay. He goes down on me, then turns me over again and we have sex. Stops. I say I wanted to come. He fucks me from the side while I use my lipstick vibrator and cum quickly.
12:30 a.m.: Remind myself to set up more dates for next week, especially with a girl. Pass out.
TOTALS: two solo masturbation sessions; one masturbation session with breast play; two uses of clitoral vibrator during sex; four acts of oral sex received; six acts of oral sex performed; seven acts of intercourse; two acts of double penetration anal; one act of drunken barely-remember-it sex.
Would you like to take part in the glorious tradition that is the New York Magazine sex diaries? Just send an e-mail to firstname.lastname@example.org with your contact information and why you think you’d make a good diarist. If you’ve got what it takes, we’ll be in touch!