sex diaries

The Kinky Theater Manager Ordering Around the Cross-dressing Professor

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Kinky Theater Manager Ordering Around the Cross-dressing Professor: Female, theater manager (between jobs), 25, Hell’s Kitchen, bisexual, “single.”

10:30 a.m.: Wake up in bed with the Professor. We met two years ago at work and have been playing ever since. He’s in a long-term relationship with another woman who is unaware of me. They live together, but she’s often out of town.

10:35 a.m.: The Professor slides his arms around me and pulls me into him. He’s already hard. Game on. He wakes me up even more by going down on me under the covers.
10:55 a.m.: Prof pounds on me until I shriek and he finishes inside of me and collapses. Just the way I like it.
11 a.m.: Still lying in bed. Thinking maybe I should have been more persistent about my own orgasmic needs.
2:30 p.m.: Straddle him at the table. I mention I haven’t come in over 24 hours and he is ON IT. After 69, he puts on a latex glove and goes to work, a surefire way to get me off. I use my favorite vibe and tell Prof to switch to the giant curved black dildo. He eagerly obliges.
2:45 p.m.: I come with resounding screams.
2:48 p.m.: We have sex missionary style, our fave position. It allows me to play with his nipples (a guarantee to a big finish). Usually we incorporate rubber attire or BDSM accessories, but so far today sex has been vanilla, naked, and loud.
3:05 p.m.: Prof finishes inside me.
12:55 p.m.: After some Iron Chef on the couch, it’s cuddle time.

11:45 a.m.: Wake up, no Prof.
12:30 p.m.: Shower. Time to get rubbered up for latex photo shoot. Slip on some leggings, a dress, and latex panties with an inflatable, inward-facing dildo.
1:17 p.m.: My mother texts me from Maryland, where my entire Orthodox Jewish family is gathered for a bar mitzvah. The Jewish guilt is staggering, and I succumb to it.
2:25 p.m.: With the Prof. He shows me a gay-porn link from a toy website. I so want to have sex, but he stops me, claiming we have to hurry.
3:25 p.m.: Arrive in Dumbo to take pics on the Brooklyn Bridge.
4:57 p.m.: Prof has a text from his girlfriend. It reads “I miss u :(” — slap in the face and back to reality. It sucks out here.
5:35 p.m.: Quick flasher photo in front of David Letterman. Why not?
5:55 p.m.: Back at the Prof’s. We are both extremely horny, but he has to go to work and I have to order train tickets. He pushes me to the bed and goes down on me …
6 p.m.: And he’s done. I am naked and lying on the bed, sopping wet and abandoned. Awesome.
7:45 p.m.: Text from Amazon Blonde whom I met at a mutual friend’s wedding. She wants to grab a drink. I am intrigued.
7:47 p.m.: Text Prof that AB has texted me. Not surprisingly, he wants to meet her.
10:50 p.m.: Convince AB to meet me and Prof at a bar close by where HOT Bartendress friend is working.
11:35 p.m.: AB is even taller and more Barbie blonde then I remember!
1:30 a.m.: Bartendress keeps the rounds coming, all of us are flirting our faces off. Prof keeps winking at me. I’m sure he wants me to be aggressive with AB and make out.
2:15 a.m.: Blueberry kamikaze shots.
2:30 a.m.: Bartendress asks for my number so we can all hang out on the LES sometime.
3:10 a.m.: We are D-Runk. AB is hell-bent on finding someone to make out with, and sadly, it ain’t gonna be me.
3:45 a.m.: Drunk, Facebook-stalking Bartendress.

12:35 p.m.: Make it to synagogue for bar mitzvah lunch with family.
1:45 p.m.: Rabbi gives post-luncheon D’var Torah about Hedonism vs. Religious Observation. I begin to daydream about jerking the Prof off as we watched gay porn. I think Rabbi is directly addressing me.
2:45 p.m.: Hiding in cousin’s room. Orthodox Jews aren’t allowed to use electricity on the Sabbath. I open my laptop and check in with Prof via iChat.
3:13 p.m.: Notice Married Stagehand Friend has commented on my Facebook status. He’s in the same town! I text him. He is waiting to get on a train back to NY but would change his train ticket if I wanted to come out drinking with him tonight. Where are his wife and kids??
4:05 p.m.: Another text from MSF. I’m in a 12-year-old girl’s bedroom. I feel majorly pervy.
4:12 p.m.: Prof asks if I will give him naughty commands to carry out this evening. I love the idea of being his Domme.
4:30 p.m.: MUST NAP OR WILL DIE. I am so horny, but the idea of masturbating is far from plausible in this house.
10:55 p.m.: Texting Prof his “instructions.” I want him to wear latex, a gag, clothespins on his nipples, and cock ring on his balls. I also tell him he needs to screw his own ass with a dildo. He is not allowed to orgasm until he has something in his ass, and I want pics for proof. Hope I sound convincing.
12:47 a.m.: Three pics arrive in my in-box of him doing EXACTLY as I ordered. Yum. Fall asleep wishing he had sent the money shot I had asked for.

10:27 a.m.: On train. Twenty-four hours with the Jews and I am ready for serious debauchery. Good thing Prof and I have plans to go to a fetish-play party tonight.
6:05 p.m.: Prof arrives home. I have to physically restrain myself from ripping his pants off. Decide that might not be interpreted as sexy.
6:36 p.m.: Prof goes down on me. It feels amazing, and I am on the brink of orgasm when he stops and says he’s hungry and we should go eat. WTF!?
7:30 p.m.: Prof has his clothes off and about to put on his latex ensemble. I play with his nipples, and he gets hard instantly.
7:44 p.m.: With his hand he makes me come so hard I nearly black out. We switch to missionary as I torture his nipples. He screams when he finishes and collapses on top of me.
8:50 p.m.: Freemans for dinner. Drunk after one cocktail.
10:25 p.m.: We stumble drunk and full to the Back Room.
11:30 p.m.: Head to fetish-play party at the Delancey. Text Editrix to make sure she is going to be there. She is married but poly. She was my first full-blown lesbian sex experience.
11:55 p.m.: Crowd is small but the vibe is very young and playful.
12:45 a.m.: Chatting with Editrix, her ex-poly partner, the Artist (a girl I often play with at parties), and the Artist’s current boyfriend (though she is also married). Artist and Prof kiss. I am definitely not in the mood to watch him make out with other girls tonight.
12:50 a.m.: Artist sits in a dark corner and demands that Prof and I play with her. He obliges quickly. I begrudgingly sit down. Prof rubs her through her panties as I tease her nipples. Prof whispers dirty stories into Artist’s ear as we play.
1:05 a.m.: Artist has to work in the morning and excuses herself.
1:10 a.m.: Chat with Editrix. Make out.
1:15 a.m.: There is Jell-O wrestling at this party. Green Jell-O. Ew.
1:30 a.m.: Prof and I are watching a few couples play. I just want to crawl into bed and cuddle. Hope I’m just tired and haven’t permanently lost my party mojo.
2:15 a.m.: In bed with Prof. Too tired to have sex, but spooning as we fall asleep in each other’s arms.

12:02 p.m.: Prof wakes up and instantly pulls me close. We start to grope and then have sex.
12:35 p.m.: I take one for the team as Prof finishes inside of me and rolls over, spent.
3 p.m.: Prof and I shop for a tranny outfit for him. We have epic plans of dressing him in vanilla drag and going out on the town.
7:30 p.m.: Dinner at Prune . Prof spoils me.
7:37 p.m.: Prof gets a call from MSF#2, who he went to high school with and wants to join us for drinks.
9:45 p.m.: Sandwiched at bar between MSF#2 and Prof. All kerplackered. MSF#2 comments that I have nice tits and proceeds to motorboat them. THREE TIMES.
10:15 p.m.: We discuss my frequent nickname “Glitter Tits,” and Prof actually pulls my pierced nipple out from my bra to show MSF#2. I don’t know whether to be turned on or pissed off! Settle for drunk and amused.
10:35 p.m.: MSF#2 and I exchange numbers. He puts me in his phone under “perfect” (almost negating the motorboating, but not quite).
11:15 p.m.: Oh, God. Meatball Shop is good.
11:20 p.m.: Bond with waitress because we both have same brass heart necklace from In God We Trust. Hers says “Sweet Tits.” Mine says “Fuck My Face” (a gift from Prof).
1:30 a.m.: In bed. Prof pulls me in to spoon, and though I am full of meatballs, beer, ice cream, and cookies, I am also incredibly horny. We start fooling around with our hands, and it feels out of this world and then…Prof falls asleep. Completely worked up, I acquiesce to sleep.

11:35 a.m.: Woken up by the Prof wanting to cuddle. I must have hit the morning sex jackpot this week.
11:50 a.m.: Prof is going down on me again. God bless his lusty new passion for this. Feels amazing, but after a few minutes I want sex.
12:07 p.m.: Prof grabs the amazing curved dildo. I yelp from the pain and pleasure.
12:35 p.m.: Mind-blowing, earth-shattering orgasm. I can’t feel my extremities.
12:40 p.m.: I am a post-orgasmic puddle, but Prof has sex with me anyway.
1:15 p.m.: I shower and groom for job interview. Morning sex has made me calm and ready to put on some good face.
3:18 p.m.: Interview over. Short and sweet.
4:21 p.m.: While I’m on Internet, Prof distracts me with the promise of sex.
4:25 p.m.: Prof rips off my panties and we go to it. We watch ourselves fuck in the closet door mirrors across from his bed. The giant black dildo comes out. I see stars.
4:40 p.m.: I wish that all of my job interviews began and ended with sex.
2:15 a.m.: We’re cuddling in bed and pillow-talking.

11:25 a.m.: Wake up in empty bed. Prof is manscaping in the bathroom. Today is tranny day, where Prof will dress completely in drag, and we will go out and do a photo shoot.
12:30 p.m.: I’m horny. I know Prof has preparations to do, but I want to get off.
12:42 p.m.: We have sex. I finish with him inside me, a rare occurrence.
3:30 p.m.: Prof is primed, primped, and wearing a butt plug and cock cage under his tights. Isn’t this how most couples spend their Thursday afternoons?
4:15 p.m.: Quick tranny jaunt around the block. A few photos and we’re back in the apartment as the sun sets.
5:35 p.m.: We’re both horny. Prof tells me I need to have another orgasm before he goes to work. No arguments here! I get his lipstick in an unusual place.
5:47 p.m.: As I orgasm I scream so hard I am convinced the neighbors must think someone has just been murdered.
6:15 p.m.: Forced to keep the cock cage on through work, Prof and I kiss goodbye and leave him unsatisfied.
7:15 p.m.: Pick up fried memory card from Tekserve. Ask to see what files have been recovered on a store computer with a giant screen. The first and only pic I click on is me flashing my tits to the camera, and also now the entire group of waiting patrons at Tekserve. Blushing, I take the card and dash.
8:49 p.m.: Text from Prof about how horny he is and can’t wait to get the cage off and have sex.
9:35 p.m.: At Bryant Park Grill listening to Cousin rail into me for my relationship with Prof and how I deserve better.
10:45pm p.m.: Ditch cousin, meet up with Prof. Ironic. I need about twelve cocktails to de-stress.
11:55 p.m.: Three Coronas, a cheese plate, and some kisses later, the stress melts.
12:45 p.m.: Exhausted and ready for sleep, crawl into bed with Prof and take the cage off his cock. I can tell we are both too tired to play and pass out in each other’s arms instead.

TOTALS: Seven acts of intercourse, six orgasms, two acts of finger-fucking, five acts of oral sex, two girl-on-girl make-out sessions, one public excursion with Prof wearing dildo panties, one rabbi lecture on hedonism, one act of public nudity under the Manhattan Bridge, one flashing photo in front of Letterman, one cell-phone number acquired from hot bartender, one naked photo displayed in Tekserve, three acts of motorboating, one tranny photo shoot.

The Kinky Theater Manager Ordering Around the Cross-dressing Professor