Misadventures in Dating

Spot: Hudson Bar
Chic: 26/Cuban
Body type: Fit with long flowing hair
Occupation: Bartender

The night started off with what some would call a boring uneventful dinner with clients and their wives. As if having my mother constantly nagging as to when and/or if I would ever get married, I had to put up with a barrage of questions form my clients wives as they tried to pry into my social life. One went so far as to be willing to set me up with her daughter. To which I politely declined. After all fucking a co-worker is perfectly acceptable, on the other hand fucking your clients daughter when said client knows what you are due to his many nights out sans wife, is generally not a way to make your career.

Side note: This is one of my oldest clients, When I moved from my last company to their competitor he came without a question asked.

As the dinner wound down, picking up a scent that the gentlemen weren’t quite ready to go back to the hotel, but they didn’t want their wives to come out, I mentioned my analysts had just finished the proposal and we should stop by the office to hammer out the details. Reluctantly the ladies agreed as we had the car take them back to the hotel.

When the car cracked the corner, cigars were lit and the pats on my shoulder began. Now these guys were in their late 50’s and desperate for a night out on the town. Knowing they had a penchant for the 22-25 year old women, I decided there was only one place to take them to have their ego’s stroked. Hudson Bar.

Usually no one gets a table here, but I couldn’t have then standing like a bunch of schlubs waiting on the little pixies to wander over. So I did what I had to, a bottle of single malt scotch, a bottle of vodka and 3 bottles of champagne. Don’t worry they will be billed back for all this at some point I’m sure.

As the waitress was bringing the mixers to our table I slipped her a couple bills and asked she send over some women who weren’t put off by older men. So said so done. Within minutes the waitress was bringing chic after chic. When the guys got settled in with their lady friends I decided to set up position at the bar and perhaps find a warm body for the night.

True to form I gave the bartenders the once over and set up shop so to speak at the hottest ones station. Her body was ridiculous, not an ounce of fat, an ass you could eat all night and the right amount of perky tits for her 5′2″ frame. I leaned over ordered my drink and turned away to wait for my drink.

As expected she tried to get my attention to give me the drink, but I waiting till she leaned over to tap my shoulder. Turning around I said “sorry I couldn’t hear you” with my fathers sly smile half cocked.

We spent the next couple hours talking, flirting and probing for a little background on each other.

As the minutes turned to hours it was time for me to put my clients into a car and send them home. Good timing to, as she was closing out her shift.

After my clients were gone, I headed back upstairs, asked her for a piece of paper, I wrote down the name of a diner and I told her there would be a car waiting downstairs to bring her for breakfast in about 30 minutes and I walked away.

While I was walking away, she said “you don’t know my name, you haven’t asked for my number and what if I don’t show?” Turning around I said nothing ventured nothing gained and left.

Well I’m happy to blog she showed up at the diner and we had breakfast, it was here we introduced ourselves and exchanged names and numbers. I’m still trying to get over the fact that her name is Babbette. Deciding that I had to slow play her to get her in bed I dropped her home after breakfast and waited a few days to call her.

Now here is the thing about bartenders, they hear it all. So you have to make some form of effort.

Eventually Friday rolled around and I had taken the day off when I called her and asked for her address, initially she asked why and I said I needed to know where to pick her up.

When I picked her up. She kept asking where we were going, all I told her was to pack a bag in case we got wet. About an hour and half later we got to a vineyard on Long Island, not too far from a great hotel .

We spent a few hours on the tour and sampling different wines when I threw it out there. “We can stay for the night or we can go back to the city.”

Without any hesitation she agreed, we were both having a great time and decided to venture out of the area for dinner. Found a great hole in the wall restaurant where we shared stories and gained a bit of insight into each other.

After dinner we went back to the jacuzzi in our room. Now I don’t know about you but, Hot tub + wine + 2 horny people = A GREAT FUCKING TIME!

The sex was nothing short of great. I would even give her an A+.

We ended up making a weekend out of it and we still hook up every couple days. Maybe I can get her to do a 3 way with the Indian.

By the way she was Cuban, strike off number 4…

Casual Dater Hit List, Real Life ass, bartender, cuban, Vineyard

Cum – thick white fluid containing spermatoza that is ejaculated by the male genital tract

Bucket – typically a cylindrical vessel for catching, holding, or carrying liquids or solids

CUM Bucket – my date from last night.

Its about 1 p.m. on Tuesday and I am stressing because, I mistakenly scheduled 5 Match dates for last night.
Date 1; The Jewish chic
Date 2; The Cuban chic
Date 3; The Indian chic
Date 4; The Armenian chic
Date 5; The Spaniard

Scrambling for ways to make this work, I bite the bullet and decide I have to clip one off and reschedule her for dinner another night as opposed to drinks last night. The Jewish chic is the first to bite the bullet. So perhaps I’ll blog her over the weekend. At least I know she will swallow.
Next is the Spaniard, had to text her saying I was working late, worst case scenario i text her every couple hours saying I was still working.
2 down, 3 to go. Now I figured if I choose 2 different bars across the street from each other I can stagger my dates and give each chic an hour. On my way out the door the Cuban calls and said “something came up” happily I said OK (she prob blew me off for some douche). Now left with 2 chics, I begin to get in the mood for the night allocating say 2 hours a piece.
First I head to Brooklyn to pick up the Armenian, waiting on the corner of her street and like a true hooker she she hops into the car as if I were a John at Hunts Pointe coming for a blow job. Finally we get back to the city, a few martinis in and Im bored, this chic couldn’t keep my interest if she paid me, so I tell her that my buddy is having a problem and I had to go help him out leaving her to work the corner.
Walked up a couple of blocks and I meet the Indian, surprisingly she was pretty hot, got along great, decided maybe she has potential to date, so lets be honest you don’t wanna hear about me wanting to date some chic. Ended up staying with her for 5 hours.
Now properly drunk and horny I decided to text the Armenian, figured she would be up for a shag, and guess what I was right. Ended up meeting her at Marquee, god I felt old. She comes out with some Russian chic and we go back to her place in BK, I’m fucking her in every hole and she is a a screamer.

Side note: She is 26 years old, in Law School and lets just say I doubt you would want her to represent you.

I’m about ready to blow my load when I decided I hadn’t given a pearl necklace in a while so I pulled out, flipped her over and as I took off the condom I came all over her.

THIS IS WHERE IT GETS PRETTY FUCKING DISGUSTING.

She looks at me smiling, rolls onto her stomach, does a wiggle and dries/cleans herself off with her sheets and turns to me and says let go to bed.
Are you fucking kidding me, you just rubbed my cum all over your bed and expect me to sleep in it. FUCK NO! How many other guys jizz is probably smeared throughout her sheets.
I got up, threw my clothes on and hunted a few blocks to find a cab back home.

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