sex diaries

The Female First-Time Fistee

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the First-Time Fistee: female, writer, Greenwich Village, 26, straight, single.

7 a.m.: Gym is totally empty, none of the normal eye candy or anorexic motivators. Curse everyone for being smart enough to stay in bed except me.

3:27 p.m.: BBM from the Euro. Ever imagined sleeping with that hot stranger on the subway? All I can say is, I’m glad I gave it a shot. He’s well-endowed, extremely handsome, and the most sexual person I’ve ever met, sort of like a Labrador retriever — goofy, sweet, can’t stop humping things. Wants to get together tonight, but he’s hard to schedule — I have to allow a lot of time for my body to recover from him. Plus, I’m hoping to get things resolved with the Ninja, the guy I’ve been seeing enthusiastically but not exclusively, tonight, so maybe there won’t be any need for him at all.
8:30 p.m.: Text from the Midwesterner. We met over the summer, and he’s really hot. He’s coming to the city this weekend.
11 p.m.: Text the Ninja. I call him that because he’s a bit of a fighter (and has the body to match) and frequently disappears without warning — technically, he travels a lot for work. We had a weird fight last weekend when one of his friends told me that he had a live-in girlfriend, which I don’t really believe but we’ve been dating for three months and I’ve never seen his apartment. I’m not angry, but I need clarification. I ask him if I can come over just to talk it out. Am thinking a cursory check of the laundry pile and medicine cabinet followed by more of the aggressive but sweet fucking we had at the beginning of the weekend. He’s able hit my G-spot and look me in the eye and tell me I’m beautiful at the same time. Swoon.
12:30 a.m.: He’s accused me of not trusting him and essentially of being a gold digger. He says he didn’t want to be judged on the basis of material things, which is why he didn’t invite me over yet, and he’s mad that I pushed. That’s really not what I’m interested in. I really liked him for him. Like, would-show-up-at-City-Hall-and-marry-him-tomorrow-if-he-asked kind of liked him.
1:15 a.m.: Crying on the phone to friend. Wonder if this is karma for the amazingly nice guy I broke up with because I realized his money was just a Band-Aid over the things we didn’t have in common. Realize that that makes no sense, because that was the right thing to do. Eventually fall asleep and have horrible dreams.

5:30 p.m.: Text from the Golfer, a guy I met a few weeks after I met the Ninja. He seems so refreshingly normal, at least by my standards. I liked sleeping with him but am not really in a mood to think about anything sexy right now. He’ll be back in a few days, and I assume vaguely that I’ll feel better by then. Or else I will have walked in front of a bus.
7 p.m.: Dinner. Make my friend read the entire brutal text exchange with the Ninja, while I weep quietly, in a Chinese restaurant. Glory be. I can see the guy eating alone next to us texting someone that there’s a girl crying next to him, so I consider this a mitzvah — he is now no longer the loneliest person there. Go home to my roommate’s Xanax (I’ve never taken one before) and pass out.

7 a.m.: Gym. Xanax is amazing. I am officially a convert. Possibly the last one on the island, I know, but better late than never. Reward my frazzled nerves with an episode of The Twilight Zone, the single best addition to my gym routine since syncing my schedule with the male model who runs next to me most mornings.
9:15 a.m.: Walk through Greenmarket at Union Square to flirt with one of my favorite vendors. We chat about the fact that my hair has literally frozen in place, and it cheers me up a bit. I don’t bother with hair or makeup most mornings after I discovered I get hit on more without it.
12:30 p.m.: All the girls in the office order in food and lock ourselves in the conference room. I’m not the only one who got painfully rejected this week; it’s a regular therapy session in here.
7 p.m.: Gorgeous party at Milk Studios. Getting a little tipsy. I’m not expecting to stay long, so I decide to break in a new pair of boots, which make me approximately sox foot three — being that tall always draws out the weirdos.
7:45 p.m.: Sure enough, craggy old guy in beautiful suit and hot, dirty boy with ponytail and holes in his shirt are circling. I chat for a bit with a guy who asks what I do, and then when I ask the same question, he refuses to tell me. “Something boring,” he says, and then finally, after an awkward pause, “Finance.” I hate false modesty, and if you really don’t want to have the boring conversation about what we do, then don’t ask me in the first place.
9 p.m.: Spot a guy I went on two dates with who told me he didn’t think it was going to work out after I suggested that he didn’t have to have his tongue in my mouth the entire time we were within kissing distance — I like a little conversation. Apparently, he didn’t. He’s got about 50 percent less hair than he did the last time I saw him, so I decide not to be a bitch and say hello. Am feeling the cocktails a bit and fall into a cab home.

7:30 p.m.: Girls’ dinner at Cafe Cluny. Most of my friends have recently gotten into relationships, or their relationships have just gotten much more serious, but they’re still great fun to go out with. My nights just end differently than theirs.
10:30 p.m.: House party uptown. Flirt with a friend of a friend I’ve met before. He’s super hot, but my friend warns me repeatedly that he’s a total slut. We drink a lot, then end up at some terrible bar in Tribeca, where he gets really aggressive; I’m not big on PDA. I see a text from the Golfer asking if I want to come over, but when I call he doesn’t answer.
3:15 a.m.:Share a cab home with the friend. He’s a good kisser, aggressive, which normally I like, but he’s over the line, too pushy. I tell him to back off and he laughs in my face, but against my better judgment I come in for a minute to give him a chance to redeem himself. His apartment is a mess, he’s a mess, spilling Gatorade all over himself. He tries to take my boots off and can’t see the zipper. I’m not that drunk, and this is annoying.
3:30 a.m.:He nearly tears my shirt in half trying to take it off. I’d planned on about ten minutes of good-faith making out but now I’m done. I make a comment, which he laughs at, and then remarks, “You know, I don’t know many funny women. Most of them are such uptight bitches.” I’m not interested in the random misogyny and reach for my shirt, but he pins me back on the bed and starts pulling off my tights. I tell him in no uncertain terms to stop and he rolls his eyes and says, “Don’t be such a baby,” clawing at my thighs. Push him off with a lot more effort than should be necessary since I already said no and put my clothes back on. He doesn’t apologize but asks me to leave him my number and gestures at the nightstand — where there’s a piece of paper with another phone number already written on it. Regret the whole thing immediately.

9:45 a.m.: Wake up to a text from the Golfer. We agree to meet for lunch.
12:30 p.m.: Have a nice, chatty meal at Good; he’s really easy to talk to. There’s something about him that makes me feel really young and immature (probably because I am and he’s not), but I’m getting more comfortable with him. He walks me home but has to go out to see his family on Long Island; I want more.
3 p.m.: The Euro texts that he’s bored at home; I tell him to come over. I just want to feel something sexually positive. We go straight into the bedroom, where he spends about twenty minutes working his lips all over my breasts, which he knows drives me crazy. He reaches for a condom, skipping his usual 45 minutes of going down on me, and unsurprisingly, I notice this omission. He says it’s because he has a “thing” on his lip. I can’t see anything but don’t trust the language barrier to try to figure out the difference between a canker sore and a cold sore.
3:30 p.m.: He starts slow, and it’s amazing — it feels like it has been a long time, at least for me. Have a crazy Black Swan moment when I see the Ninja’s face instead of his when I look up at him but shake it off and try to focus; he flips me over, which certainly helps. He always tells me how much he’s missed me right before he starts thrusting harder to make himself come, and then lies on top of me for a long moment, before going to clean up and wash his hands.
3:45 p.m.: He comes back from the bathroom with a towel, which means it’s time for his favorite party trick. I’ve never squirted with anyone besides him, and he has this virtuoso technique down; I feel it coming as soon as he starts in on me, and he presses down on my stomach to get every drop out.
4 p.m.: The latest project we’ve talked about that we actually can agree on is fisting, something I’ve been curious about (more in an academic sense than a sexual sense) for a long time — I trust him implicitly, so we decide to give it a try. He squirts lube all over the back of his hand and all over me and starts working his fingers in one at a time, whispering encouragement; it doesn’t hurt, but the pressure is intense. He gets his hand in up to the base of his thumb, but that turns out to be the sticking point. The novelty is exciting, but I can’t do any more, and he tries a few more times but ultimately gives up and pulls me in to spoon me and talk for a while.
5 p.m.: Shower when we realize we’re literally stuck together from all the lube. We kiss goodbye; he has a client dinner and I have a missed call from the Midwesterner. Call him back, and then get back in the shower. First one was for the dirt, second one for the principle of the thing. Brush my teeth, put on clean clothes, change the sheets, light candles, sweep the floor, and take out the trash — I feel like I’m wiping a crime scene.
11 p.m.: Head to the Standard to meet the Midwesterner; his face lights up when I walk in. His friends are nice except for one girl, whom he explained previously was someone he’d recently reconnected with. She’s nice enough, but clearly interested in him, which I could probably have predicted. He doesn’t do too much to discourage her, but in that subtle, female-warfare way, I know he’s more interested in me and probably just enjoys the attention.
1 a.m.: He pins me against the wall on my way back from the bathroom and kisses me. Wish he would stay with me tonight but he says he has an early train to catch tomorrow.
1:30 a.m.: He’s walking us home — us, because this chick is still hanging around. She takes his arm and tells him that she has to turn at the next corner, clearly an invitation to go with her. I actually have to walk down the exact same street, but I’m tired of her, so I keep quiet in order to force a decision. Sure enough, he pulls his arm free and gives her a hug goodbye. That’s right, honey, walk away. We kiss on the corner for a while and he asks me to come visit him soon. Sad to see him go, but happy not to be doubling up today, although technically it’s after midnight.
4:30 a.m.: Oops. Ended up hanging out after hours at a nearby bar, where my friend bartends. Catch him up on the end of the weekend’s shenanigans. I’m still sad about what happened with the Ninja, but he hasn’t called, and I know I have to put it out of my mind. Gin helps.

8:30 a.m.: Wake up. Ouch. My breasts are sore from yesterday, and my hips are a little stiff, but overall I feel good. I’m still tired, and a bit sad.
6 p.m.: Feel bloated from all the alcohol this weekend, so I head to class at Physique 57. Missed call from an ex who is such a jackass he’s not even getting a nickname. My roommate has someone over. Ignore him, make dinner, shower, and pass out.

6:15 p.m.: Golfer texts and asks what I’m up to. He suggests ordering in sushi, which works for me. Normally I’m hesitant about spending too much time together informally at the beginning of a relationship, but then again, I’m still single, so what the fuck do I know? At least he lets me into his apartment. Decide from now on the only policy is doing exactly what I feel like, except for drunk-dialing and sex before the third date, and head up to Chelsea.
9:30 p.m.: Chatting about nothing in particular. For some reason, he always asks questions that get at my absolute worst, most sordid stories, and I worry he thinks I’m slutty. He throws me onto the bed and undresses me slowly. His bedroom is beautiful, and I always wonder if an ex-girlfriend decorated it. We kiss for a long time, and he fingers me until I come and then grabs a condom and gets on top of me. His dick is thick and gorgeous, but it’s over all too soon. I mention something vague about getting up early to give him an out if he doesn’t want me to stay, and he takes it — disappointing. Go home and research grad programs in France until I fall asleep.

TOTALS: Two acts of intercourse, one attempt at fisting, one act of pleasant making out, one act of date-rapey making out; one heartbreak.

The Female First-Time Fistee