sex diaries

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

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Picky, Prowling 23-Year-Old Woman Looking for a Guy Who Knows How to Give Head: Female, digital marketing coordinator, Chelsea, 23, straight (until the third drink), single.

7 a.m.: Impressed by all the hot, shirtless guys on my run around Hudson River Park. This must be where all the straight men in my neighborhood hide. Decide to cut my run short so I can fantasize about them.
7:36 a.m.: Despite my steamy thoughts of the stud I jogged next to, this shower is not doing it. Suddenly remember that waterproof vibrator I got from some press event and hop out of shower. Can’t find it. UGH.
7:53 a.m.: Race back into apartment to change panties to slutty red lace thong because I realize I probably won’t have time to come back after work before I meet up with 920 (his area code).
8 p.m.: On Charles Street by August where 920 told me to meet him. Admittedly, we’ve never hung out before 11 p.m. so this could get awkward. Giddy up.

8:15 p.m.: Realize I was so drunk the first time we met that I know nothing about him other than he’s 28, has a nice dick, and is likely balding.
8:20 p.m.: Text friend telling her she might need to rescue me because am meeting up with some obese, greasy, bald dude I accidentally hooked up with when I was really drunk at Brother Jimmy’s (shocker) a few weeks back. Hey, at least it wasn’t Tonic. So it’s probably safe to assume he’s not a Pauly D but a harmless post-fratboy went-to-“Wisco”-Delta-Epsilon whatfuckingever type.
8:30 p.m.: Shocked and pleasantly surprised when 920 approaches me and kisses my cheek. Incredibly handsome. Aren’t beer goggles supposed to work the other way?
9 p.m.: Well, it might have been awkward at first but nothing a little fig-infused vodka can’t solve. He’s rubbing my thigh. He tells me he likes my dress and I reply, “You can borrow it anytime you want.” Clever, I know.
10:15 p.m. In a cab. Remove his cock from his crisp business pants. Start going down on him in the taxi. A pedestrian slaps him five through the window. I love Manhattan. Cab stops short and I nearly choke.
10:38 p.m.: He pushes me onto his bed and flings my dress off in one fell swoop. I’m riding him slowly and he’s trading off between pulling my hair and rubbing my clit. Great sex but I can’t stand the baby talk. Wish I could use the mute button on the remote control lying next to his bed on him.
10:55 p.m.: Okay, I really can’t stand this baby talk. I’m pretty close, but as soon as he’s done I bolt the fuck out of there so as to not listen to this Gerber Baby’s soundtrack any longer.

3 p.m.: 858, the 31-year-old advertising guy, and I are texting. He’s at his company picnic but would like to make a bad decision or two with me tonight.
11 p.m.: I’ve somehow managed to secure a stamp for a free open bar and bottle service at this snooty place called the Anchor. Allegedly, this is on account of my business card, but based on their creepy stares, more likely because I look like a pair of legs tonight.
11:02 p.m.: 858 shows up, tells me my ass looks good in that skirt, grabs it, and ushers me in.
11:05 p.m.: Holy shit. Is this intern night? There is no way the girls in here were born before Selena Gomez. God, I’m getting old if half of America worships a Disney character born in the nineties. The guys are all twentysomething banker types and the gold-digging minors are loving it. 858 and I discuss how we are bringing up the average age by 9.7 years.
11:30 p.m.: Only way to cope with being at the Mickey Mouse Club is via vodka.
11:55 p.m.: Lots. Of. Vodka.
12:20 a.m.: We’re grinding on the dance floor to the likes of “Too Close” by Next, “C’mon Over” by Christina, and “I’m a Slave 4 U”–era Britney. Nobody on the dance floor knows the lyrics but us.
1 a.m.: 858 pushes me up against the D.J. booth and is trying to finger-bang me on the dance floor. I suggest we relocate, mainly because I’m convinced we’ll bump into my little brother, a senior in high school.
1:40 a.m.: We stumble down the street to the Ear Inn, a romantically rundown bar. Contemplate giving him a blow job in the bathroom but then realize he might call it a night from there and head back to his apartment and I don’t want to risk hailing a cab alone in the part of Soho so fucking west I might as well be in Jersey.
2 a.m.: Glad we didn’t do the whole BJ-in-a-public-space thing. Back at my place. I am quite drunk. Vague recollections of having my period.
2:05 a.m.: 858’s going down on me. I’m normally not into that because it makes me too horny and I’d rather just fuck, but 858 is quite talented at teasing my pussy with his tongue.
2:08 a.m.: Is he spelling out the alphabet? Really? Bet he thinks he can get me off by Z …
2:15 a.m.: He’s using one hand to finger me and when I’m on the brink, he sucks on my clit nice and hard. Why do I normally get all squeamish over getting oral? This is fucking awesome. Why does he keep telling me how wet I am?
2:16 a.m.: OH SHIT. I know why.
2:18 a.m.: Please don’t kiss me. Fuck. Fuck. Phew. Crisis averted.

10:05 a.m.: Wake up to a trail of five (what the fuck?!) Magnum wrappers on my floor and a pile of bloody condoms in my trash bin. I briefly wonder what it tastes like to go down on a girl who has her period.
10:07 a.m.: Throw up.
8:25 p.m.: Over dinner, my poor guy friend is convinced he has herpes after hooking up with a girl from Turtle Bay (shocking).
8:30 p.m.: I ask him to describe the symptoms. After this morning, how bad can it be? “Um, babe, You just have ingrown hairs … ”
8:40 p.m.: Celebratory beers to celebrate lack of herpes.
9:30 p.m.: I’m chatting up a group of eight finance (fuh-nance, not fy-nance, sweetheart) types. Vaguely attracted to the only guy in the group who doesn’t look like he’s been transplanted from Martha’s Vineyard.
9:45 p.m.: 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.
11 p.m.: I repeat the experiment using another pool of guys. I tell three they’re hot, and three they’re hotter than all of their friends.
11:20 p.m.: Tallying up statistics on a napkin. I got six out of seven phone numbers when I phrased my statement in the comparative form (“I just want to let you know, I think you’re hotter than all of your friends”). Only got two out of seven numbers when I told them they were just plain cute/hot. I think I’m onto something. I should contact the Journal of Social Psych.
12:10 a.m.: Making out with 216, the original guy I thought was cute, plucked from the table housing the Manhattan Outlet of Martha’s Vineyard. Turned on but then think of this morning’s bloody fiasco. Decide an Irish Good-bye is best.
12:30 a.m.: Bed, box of Crispix, a juicy peach, slice of olive pizza, Diet Coke, Possible Side Effects by Augusten Burroughs, “Gold” humming from my speakers. Life is good.

7 p.m.: Nursing a frozen mojito at Reunion, rereading Dry by Augusten Burroughs.
8:30 p.m.: Very strange fortysomething women dressed like psychics approach me and say I’m beautiful but they want to realign “my energy field” so I can attract better mates.
8:40 p.m.: Energies realigned and now strolling along Ninth Avenue when I spot a really cute guy. Decide to approach him and say, “I’m sorry to bother you but I just moved here and I was wondering if you knew any good bars?” He suggests several and asks for my number so we can get a drink sometime. I tell him, “How about we make that sometime now?”
8:50 p.m.: Sitting at dive bar with 310 and thinking maybe those crazy psychics did the trick. He’s handsome, well spoken, and paying for my drinks. A rare combination in this town.
1 a.m.: Back at my apartment with 310. I don’t normally do that, but I was getting really good vibes from him. We’re a mess of tangled tongues and limbs. I hate hooking up to music but I know if I put on Nirvana, it’ll give me an opportunity to pull away if he’s trying to have sex with me and play the “Oh my God, Lithium!!! I love this song!” annoying girl card, so I throw it on. He gives me two orgasms with his hand. I really don’t want to return the favor and find out so soon that this seemingly great guy has a Burt Bees’ for a penis and get disappointed but I take a peek.
1:03 a.m.: Yep, definitely wouldn’t be able to tell whether or not he was trying to fuck me or fix chapped lips with that thing.
3:05 a.m.: Text from “No Idea But Cute Flannel” (310) who has just left my apartment saying he can’t wait to see me again. And oh, did I like waffles? He could take me to this great waffle truck! Starting to get the ick from him. Ugh.
3:20 a.m.: Three missed calls from 310. He’s stuck in my elevator. Ha ha ha ha ha. Decide it is in my best interest to pretend to be sleeping. God, I’m a bitch.

7:05 a.m.: Wake up to a text from 310 telling me he didn’t want me to wake up to “stuck in your elevator!” texts so he wanted to compose a sweeter one for me instead. Now I understand why it is so unattractive when girls send these flowery texts to guys they just met and try to turn a one-night stand/make-out/whatever into something more meaningful.
11:30 a.m.: These texts need to stop. I don’t even know his name. Ick, ick, ick.
5:30 p.m.: Get every girl’s worst nightmare text from 310: “Hey, listen, there’s something I need to talk to you about the other night, confidentially. Can you call me?”
5:45 p.m.: You sent me that god-awful text to tell me the reason you were acting so weird was because the night we met you found out your friend’s dad is sick? Listen, I’m sorry about that, but really?
7:30 p.m.: Drinks with work mentor and bitching about 858, 310, etc., and the generally pathetic trajectory of my love life. She wisely reminds me that I’m still young and dating around is healthy.
9 p.m.: 858’s b-day so we meet for drinks at Rattle ‘n’ Hum. He’s groping me and very clearly wants to get out of there.
10:02 p.m.: 858 grabs his digital camera while I go down on him. I think he thinks I’ll be too drunk to remember, but I’m not.
10:15 p.m.: But it’d be really fucking awesome if he could hook up his camera to his TV right now so we could watch him bend me over his coffee table and fuck me while it’s happening.
10:16 p.m.: He comes all over my face.
11:30 p.m.: Walking back to apartment. Ugh, my hair kind of feels like straw right there, definitely in my hair, too. Great.

7 p.m.: Why is 310 still texting me? Can’t he fucking take a hint? This is a great wake-up call of how I probably come off when I text somebody I’m into who wanted nothing more than a drunken tryst and to leave it at that. Now I completely see how goddamn annoying it is.
8:30 p.m.: Giving girlfriend advice over dinner. Trying to remind her that dating in your early twenties is more about having experiences than the actual boys themselves, it’s about nights that make you cringe and not about just getting hung up on a specific dude or situation. Wish I could follow my own advice.

9 p.m.: Buzzed at my friend’s apartment. She just happens to be neighbors with 858. I text 858 that I’m at his neighbor’s and have a surprise for him.
9:20 p.m.: I don’t really have a surprise for him other than I’m drunk.
9:30 p.m.: Do my pigtails count as a surprise? 858 wants to know what the surprise is. I tell him, “If you come back uptown, it’ll be worth it.”
9:35 p.m.: 858 arrives. Men are so easily persuaded.
9:38 p.m.: Oh shit, does he think I was implying a threesome? Whoops.
9:40 p.m.: He’s drunk and doesn’t seem to care about the lack of surprise.
10:45 p.m.: Boys in suits at Banc are trying to buy me drinks. I flirt with them for a little bit, but only to see if 858 will swoop in.
1:10 a.m.: Back at 858’s apartment. Drop to my knees to blow him while he pulls my pigtails.
1:15 a.m.: Having sex with him on top. Normally I’m a fan of slinging my legs over the guys shoulders but he’s so big that I’m scared it will hurt. He’s not taking no for answer tonight. I kind of like when he gets all rough and aggressive and pins me down like this.
1:30 a.m.: 858 is bending me over the couch and fucking me from behind. He’s clenching my neck with one hand and spanking me with the other, telling me I better be ready to be his dirty little slut tonight. He’s a cashmere sweater and blue jeans sort of guy. It’s always the sweet, reserved-looking ones who are the best dirty talkers.
1:45 a.m.: 858 is passed out, so I hunt around for his camera and delete the pictures from the other night that he doesn’t think I remember him taking.
2:03 a.m.: As I drift along Park Avenue, I soak in the smells of almost-burnt and incredibly doughy bagels, the sounds of happy twentysomethings clacking their flip-flops, and the sight of the ever-comforting glow of Grand Central Terminal. It feels great to feel the breeze of the night kiss my neck and reunite with my city. The city. His city. And though I may not know who he is yet, for the first time in a while, you know what? I’m okay with that. Sure, there are those nights when I wish I had a boy to hold hands with on my late-night stumble home. But most nights, I’m perfectly content with knowing Manhattan is the one man I can count on whose hand will always interlock perfectly with mine.

TOTALS: one would-be orgasm interrupted by a Gerber’s sponsorship; two manual orgasms; one blowjob to a golf pencil; two acts of oral sex given; one act of oral sex received; five acts of intercourse; one Stage Five clinger; one eternal love affair with Manhattan

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