Hot bartender hookup (boring old m/f but with a picture!) | 2016

I was in Wilmington, DE last week. Have you ever been to Wilmington? It sucks. You aren't to far from Philly, where you can have a lot of fun, but if you are stuck in Wilmington for three nights like I was, you want to poke your eyes out with the pen of John Dickinson (the Penman of the Revolution...shit, the fact that i know that means I've been in Delaware too much lately).

Anyway, so I'm stuck in Wilmington on business (corporate taxation is SUPER fun, lemme tell you about it) and sharing a rental with my boss, who's the opposite of fun. I ask him if I can go to Philly to visit friends one evening (really, to go to Center City and try to find a fuck buddy) but he's worried that I might get inebriated and what would that do to the insurance? Fine, after a "delightful" dinner near the Doubletree (you know it's a fun place when they have not one but TWO litigation centers...good lord kill me now) with my asshole boss, I tell him I going to crash, change out of my monkey suit, and try to find a bar that isn't catering to my kind (ie asshole businesspeople in Delaware for business).

After wandering for a little while, I find a bar that has a modest lighted sign out front, no neon, no dumb drink specials being touted, and I walk in and realize I found my joint for the night. 3 TVs, none of them larger than 25 inches or so, the bar not lit particularly well, the smell of fried food making its way into every pore, a jukebox playing rock music from the 70s, the whole joint half filled mostly with guys around my age dressed in decidedly unbusiness-like attire, mostly clumped together in groups of three or four...and a hot blonde bartender with a huge rack.

I walk up to the bar and order a burger and fries and ask for whatever's on tap, while enjoy the ample cleavage Cynthia is offering for all to see. I watch her head to the kitchen to make my order and enjoy her tight ass wrapped in jeans, a pleasant squeeze of fat spilling out from under her checked button down shirt and over her waistband.. When she comes back, I make chit chat, trying to figure out if I have a chance here or if I should wait to see if there are any ladies available later in the night.

Cynthia is pleasant and chatty, telling me how she ended up in Delaware, went to UD for a semester before dropping out and then getting stuck in Wilmington, and she milks me for information about me, all the while, deftly serving the other patrons, many who run their hands over her ass or even brush up against those big titties when she comes to the tables with drink orders. She doesn't seem to mind the attention or handsiness, which is a good sign to me.

People come and go, I finish my overcooked burger and fries and wash them down with 4 (or 5) beers, all the while staying at the bar and using all of my charm to hit on Cynthia. She's happy to flirt back--I can tell she does well on tips due to her gregarious, and understanding nature.

It's just part midnight when she let's me know the bar shuts down at 1. By now there are only a few other patrons left, and I've convinced Cynthia to join me for a beer (not that she needed much prodding). I put on a sad face and tell her that I'll miss hanging out with her, and am delighted when she tells me that she's also not ready to end the night.

1 AM rolls around and the bar is empty except for the two of us. I settle up my check with a very healthy tip added on top and Cynthia shuts the joint down. As we head for the door, I pull her close to me and we start to make out. My hands explore her curvy body and as I'm reaching into her pants, she pulls my hand out and shakes her head. Not her bar, she tells me, and she doesn't want to get in trouble with the owner, tilting her head at the video camera in the corner.

Fair enough. She agrees to see the inside of the jewel of Wilmington that is the Doubletree (did I mention that it has TWO litigation centers? HOT!) and we enjoy the cool fall air and get back to the hotel. Straight up to my room, where she lets me unbutton her shirt, kissing down her front as I do so. She wiggles out of her jeans and undoes her corset--as if she needed a way to show more cleavage--and I ask her to if I can take a picture of all her beauty. Thank the Gods that she says yes, and I can share below.

She asks if we can watch a little porn as we make out, and I'm happy to comply. I have a six pack of Heiniken in the minifridge and we crack a few open, her just in hot pink undies, me in grey boxer briefs, my cock tenting out, as we sit on the couch and watch Co-ed Sluts 3 or something or another. She's rubbing my cock through my underwear with one hand and downing her beer, as I fondle those wonderfully large breasts. I slid a hand into her wet underwear and probe her swollen clitoris, earning a gasp. I tell her to put down the beer and climb on top of me. She really wants to watch porn and get fucked, so she pulls down those panties and sit facing away from me. I continue to probe her wet slipper pussy as she slides her ass back and forth on my hard cock. She tells me where she wants me to put it, so I pull off my underwear and slide on a condom and penetrate her. She leans back against me and I kiss her shoulders, her neck, her lips as she twists around as she rides me hard, grunting in a very animal way. She's bouncing hard and I push against her, holding onto her hips so I don't pop out until she cums hard, falling forward on her meaty thighs and breathing heavily, her hair in her face. I let her come down from her orgasm just a bit, before pushing her off the sofa and onto her knees and hands, where I take over the hard work and do my best to send my cock all the way through her.

It's hard work and after five (ten?) minutes, I'm out of breath. I knew I should have done some more cardio in the hotel gym. Sweat's pouring down my face and her ass and pussy are slick with juices. Cynthia tells me to sit back down and turns to me, her heart shaped face lovely even with sweaty hair pressed against her cheeks and her mascara running. She gets between my thighs, slides off my condom and proceeds to give me a world class blowjob, expertly licking and sucking every part of my cock until I explode in her mouth. She swallows my entire load with a grin and comes up onto the sofa and presses her body against mine. We enjoy a companionable quiet, the only sounds the moans of the actors on the screen, and sip beer.

After a few minutes, Cynthia moves her hand to my cock and before you know it, we're on my bed. She's on her back, her legs up, and I'm on my knees and thrusting into her and watching her huge boobies bouncing and following like waves. So hot. I get her again before finally cumming too, so hard that it feel like I could have shot the condom right off (thankfully not. That be bad).

It's almost 4 AM and she asks to take advantage of the fine water pressure you can always find at a Doubletree. I nod and then nod off, waking up to see Cynthia fully dressed and leaning over me. "That'll be three hundred dollars," she tells me and I feel ice water shoot through my veins. She's a hooker? Really? All my flirting and macking was in vain? Then she laughs and I relax. She got me good and we both know it. She buttons the last two buttons on her shirt and I say goodbye to the twins and she asks if I'm in town for a while. Alas, I'm leaving the next day but I tell her I expect to be back in a few months. She tells me not to be a stranger, give me a chaste kiss on the cheek and is out the door.

I'll be heading back to Wilmington tomorrow and I know where I'm heading on my first night. Wilmington still sucks but at least there's one small bright spot in that shitty town.

As promised, a pic! http://imgur.com/GgyyjfD