sex diaries

The Consultant Juggling Nymphomaniacs and Longing for an Upgraded Ex

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Consultant Juggling Nymphomaniacs and Longing for an Upgraded Ex: male, single, 29, straight, Carroll Gardens.

7:30 a.m.: Typical morning: masturbate. Think about Nympho Babysitter from Sunday night, which was fun/weird 

… 3 drinks, my place, clothes off, sex talk. She rubs herself onto my thigh, asks me to put a finger in her ass. I oblige, she gets off, puts clothes on, and says, “You can get yourself off.”
9 a.m.: No beautiful women on train this morning, so no daydreaming about finding my gorgeous indie wife in bourgeois Brooklyn.
10 a.m.: Text from Upgraded Ex (she looks better than when we dated). We broke up because she was falling in love and I wasn’t. Recently, we’ve reconnected and sparked our attraction again. Part of me wants to be back with her because we get along so well but then I remember we just don’t have the same interests. We make plans to meet for drinks after work. I plan to clarify our current thing so neither of us gets hurt.
3:30 p.m.: Text Sweetheart Family Friend about planned drinks late tonight. I was surprised that we slept together when we hooked up, and now she wants more. This is a delicate situation that needs to be handled with care.
4 p.m.: Nympho Babysitter tells me she wants to be friends and will see me around the neighborhood, but no other dates. Damn, no more ass play. Not hurt at all.
5 p.m.: Text with New Girlfriend Material to set up our first date. I already thought she is girlfriend material from one half-hour conversation. Then again, I usually know when they aren’t within a half-hour.
8:26 p.m.: With UpEx at a bar on the LES, making out. Just had the talk. She brought it up. She thinks of me as the fun on the side. I couldn’t be happier.
9:19 p.m.: Big kiss, said good-bye. Bad time of month for her and she didn’t want to power through. Rubbing my cock with her knee has left me still hard on the train. She wants to come over late on Sunday and give me the greatest hits from our history. Grin ear to ear: Bday-ex-sex, NSA.
10:30 p.m.: I lay in bed and get off thinking about UpEx.

9:15 a.m.: The walk from the F at Broadway Lafayette to the uptown 6 = two blocks that are concentrated with the most beautiful, stylish women in all of New York. Where can I meet any of you?!? Do I have to resort to Internet dating to find a smart, successful, beautiful woman to settle down with?
1:35 p.m.: Text with SweetheartFF to see if she’ll be around for birthday celebration on Sunday. She said dinner would be long, but she’ll be around Sunday during the day. Might have to manage several partners on Sunday. Not looking forward to that …
4 p.m.: Just found out that I will be going backstage at the concert I’m going to tonight. Sick!! Gotta figure out a way to grab a girl at the show and bring her with.
5:14 p.m.: Send a text to Bartender Booty Call. I was her boss years ago and we had a steamy affair which included a few cocaine binges and lots of adventurous sex (especially in the restaurant where we worked). She also lets me come wherever I want on her and she especially loves the face. That’s hot. We’ve been trying to reconnect lately.
9:45 p.m.: Song lyric reminds me of Ex That Could Have Been the One. I miss her terribly. We broke up because of distance and now she won’t respond to texts. I really wonder why she’s acting like this. My hunch: She thinks I always knew that when I moved back to NY, we would break up. I never wanted that at all — I just wanted her.
1 a.m.: Riding around neighborhood in Brooklyn trying to figure out where I can pick up a girl. Finally go home, order food, fantasize about Bartender’s face, get off, sleep.

9 a.m.: Alarm wakes me up despite no work. I feel like it was a failure because I didn’t hook up last night. When am I going to stop judging everything based on getting laid? I wish I’d grow up at some point. I’m guessing this is all part of the reason I’m super-single.
11 a.m.: Hot Asian Setup texts me to figure out plan for the night. A friend brokered us into going out via picture texts and Facebook. I suggest we meet for lunch before our drink date later tonight. She loves the idea.
11:15 a.m.: I text the friend who set us up to get the updated scoop, and he already knows about the lunch. Says she has a boyfriend, but she recently convinced him to have an open relationship. Even better, he set her up with a different mutual friend who gave her her first orgasm. I love a challenge!! This also means that her current boyfriend doesn’t get her off. I’m baffled as to why any woman would stay in that situation. I’m sure this actually happens way too often.
2:40 p.m.: At lunch in best new Italian spot in Little Italy: Wu-Tang blaring with hipster servers. HotAsianSU is extremely, well, hot, with a petite yet curvy body.
6:15 p.m.: On the way to a food event in Queens, a buddy texts me that his colleague will be at the same event and we should meet up.
7:15 p.m.: After colleague and I pick a spot to meet, I text her my description. She returns with: “I’m 6’0”, blond, with a black dress on.” I hold back from dropping my phone and frantically searching for her.
9:45 p.m.: Setup date with Stunning Tall Blonde. Actually think this one has potential. For all the complaining I do about not knowing where to meet people, I seem to be on some type of roll here. Knock on wood.
10:30 p.m.: Drinks with HASU. She explains her open-relationship situation, and I counter by leaning in and kissing her. At first it’s soft, but then she gets a hold of my bottom lip and that gets me going.
2 a.m.: We’re back at my apartment making out. Wow, she has a hot body. And I always appreciate when a woman is aroused by nipple play. We keep it fairly innocent and decide no sex tonight, even though we both want it. I do get to play with her clit a little.
3:30 a.m.: After HASU leaves, I get off thinking about her. She will be very fun in bed, and I’m looking forward to it.

10 a.m.: Wake up, think about fooling around with HASU. Get off.
Noon: I get a text from HASU: “Wanna play today?” I guess I do, but hesitate cause I think she may be getting clingy. On the other hand, maybe she wants to finish what we started last night.
3:30 p.m.: At fun day-drinking food event with HASU. We’re constantly grabbing at each other, which I’m sure is annoying for everyone else. Invite her back to my place to smoke and hang. She’s in.
6 p.m.: Things escalate quickly. She reaches into my pants, and starts going down on me. I start talking dirty. For me, talking is one of the best parts of sex. I sense she wants me to throw her around and tell her what to do. We move from the couch to the bedroom, and I start to lick her.
6:30 p.m.: While I’m on top of her, she has a mini-orgasm and tells me she wants me to, also. I ask her if I can do it on her, and she says, “Wherever you want, baby … ” She loves it — so much for shy!
8:15 p.m.: After our session, I jump into the shower. I hear the door, then watch as she steps into the shower. I am hard again. Without saying anything, she sits on the edge of the tub, and starts blowing me while leering at me.
9:20 p.m.: I drop her off in a cab downtown. Three cute girls are on the same corner waiting for a cab and I gesture for them to get in. They ask me who the girl was and I tell them her it’s a no-attachment situation. One responds, “Well, I guess she’s seeing that in action right now” and lends a sultry smile. Cutesy redhead from Brooklyn gives me her number.
Midnight a.m.: In bed, alone. So tired from HASU. Too tired to get off. Pass out.

9 a.m.: Wake up. Think about UpEx coming over late. Watch old sex tape of us together, where she gives me an amazing blow job. Get off.
5:15 p.m.: UpEx shows up at bar where friends and I are gathered to watch football. I’m half-drunk at this point and she looks great. SweetheartFF is here as well. I do my best to pay attention to both, but focus on UpEx. I want her so bad I get hard several times.
6:40 p.m.: SFF leaves and gives me half a kiss. Uses some “I didn’t have gum excuse” via text. Again, no bother to me. She’s lost my interest.
9 p.m.: UpEx and I are in my apartment. I slowly take her clothes off and savor the opportunity. We move over to my kitchen counter, one of our favorite positions. She has her legs spread as much as possible.
9:30 p.m.: She says I should look behind us. I see my mirror is catching all the action and she is watching. She comes with me inside her. It was amazing. We work our way back to my bed (after a brief stop for doggy-style near that mirror). Feels amazing to embrace her intimately. We fall asleep.

8 a.m.: We wake up with time for her to shower before work. She kisses me passionately and rubs my body.
11 a.m.: Get a text from HASU saying she called sick to work and wanted to see if I could leave work for lunch. I tell her I’m off and she says she’ll be over in an hour. I shower.
Noon: HASU walks in. It takes her no time to get me over to my couch. She has on thigh-high stockings and a short skirt. She straddles me — I’m already hard — and her skirt rides up to reveal pink lace underwear; she obviously came over for a reason. I run my finger along her underwear, then pull it off, leaving the rest of her clothes on.
12:30 p.m.: I have her kneel next to me on the couch where she opens my pants. When she asks for me to get inside her, I pick her up and put her on my kitchen counter, where I was about twelve hours ago. Unfortunately, no comparison to UpEx, who could teach HASU about not only me but sex in general.
1:20 p.m.: No more than twenty minutes resting and she wants more. Then we order food. Delivery in 45 minutes. Attempt some rest.
1:50 p.m.: No rest, more sex. Give her some, and before either of us can come, the food arrives. Phew.
3:30 p.m.: After lunch, I fend off another session with a fictional prior engagement. HASU leaves, taking with her my mojo for the rest of the day. Still need to go to dinner with New Girlfriend Material at 7.
8 p.m.: Less then an hour in and I realize we have no chemistry. Do I find the nice ones too boring and the crazies too nuts? Where is that middle ground? I think I had it once and she cheated on me. This dating crap is tiring, boring, or simply absurd. And we all do it. Maybe I should turn to the interwebs for help.
9 p.m.: Cheek kiss. The second date’s kiss of death. Thank God.

8:30 a.m.: It’s raining and it’s my birthday, so I cab it to work. All I can think about is Ex That Could Have Been the One; I queue a playlist that she made me. I realize that none of the fucking-around crap makes me actually happy. Nothing like some good old birthday depression with Cat Stevens’s “Sea of Love” blaring in your ears. I miss her.
10 a.m.: UpEx sings happy bday to me on my voice mail. Warms my heart.
6 p.m.: Hit dinner with my two closest friends at four-star midtown restaurant. Meal outstanding. Run into some other friends who want to keep the party going.
2 a.m.: At private room in strip club on UES. Naked women everywhere. I live in the moment and go with it: triple kissing two girls, licking, stroking, pinching, biting. A year older is not a year wiser. Hopefully I’ll grow up some day.

Totals: five successful acts of masturbation, one hand job, three blow jobs, one act of cunnilingus, four acts of intercourse, three makeout sessions.

The Consultant Juggling Nymphomaniacs and Longing for an Upgraded Ex