The well dressed milf in the corner

You decide to take that more glamorous looking crossdresser sitting at the end of the bar, from where you can see, she's a pretty drop dead gorgeous girl with ruby red lips and a simple slick black dress and long pantyhose. You maneuver around the crowded bar, keeping an eye on the lady. She hasn't really noticed you accept for when you first came in and she has since gone back to her drink, keeping a casual eye on the rest of the large room. You successfully get through the mass of many alluring ladies and manage to get behind the sexy lady and come right up against her. She's in great shape with just a little curve in the hips. She still hasn't noticed you yet but as she looks back out across the bar, she detects you out of the corner of her eye. Before she can say anything, you grab her hips and pull her back, sliding her ass halfway off the bar stool.

"Hey-"

You reach out and place your hand firmly over her mouth.

"Don't cause a scene baby." You purr in her ear. She looks back at you, grabbing for your hand. She manages to pull your hand away with both hands but you’re clearly stronger.

“What do you think you’re doing?”

“Come on, baby, every girl in this bar is looking for a cock in her ass, even you.”

Your other hand reaches around the pretty lady’s front and quickly finds a modest little bulge in her dress. You squeeze it firmly and she seems to lose her resistance, her hands drop from your arm and you feel her lift her firm ass up a bit off the barstool so you pull her skirt out from underneath her and lift it. She has nice snow while lacy panties and with her halfway off the stool, you easily pull them down far enough. The woman doesn't struggle too much as you pull your cock out of your dress pants, your hand back to covering her mouth. She tries to get your attention, her eyes a little fearful, but you tighten your grip and she freezes.

"Spread 'em wide."

She looks over her shoulder with wide eyes but does as she's told. She grabs her ass cheeks and pulls them apart for you, exposing her tight little entrance. You let go of her mouth and she remains silent as you grab her hips again and press the tip of your dick to her asshole.

'Please, you're not even lubed up." She whispers.

"You look like the kind of girl who can take it dry, I’ll bet you’ve had some pretty big tools thrust up your little ass, maybe so huge toys. Now get ready baby."

She tries to pull herself open as wide as possible as you push the head of your dick against her tiny little hole. You feel the milf take a deep breath and you decide just to ram all eight inches of your manhood deep inside her. She lets out a little cry of pain before cutting herself off. She places her hands firmly on the bar and braces herself as you immediately start pounding away at her. She’s unable to relax as you rapidly pump your dick in and out of her already red and sore hole, loving how amazingly tight she is. She resists as much as she can, but the more she presses back against you, the easier it is to piston in and out of her aching body. You look around and try not to draw too much attention to the two of you as you fuck this sexy bitch right out in the open. No matter how much she seemed to protest, she still just sat there and let you plow into her so you figure she couldn’t be that much against what’s happening. You’re surprised at how quickly you feel your orgasm build, it must be from how much she is clenching tightly around your erection, so you slow down to draw out the experience. Maybe she wants you to cum quickly so you’ll pull out of her and leave her be. You silently promise her that isn’t going to happen, weather that was her intention or not as you pull nearly all the way out of her ass before thrusting your entire length balls deep back inside her. Her face is pressed against the bar and she seems torn between enjoying the rough treatment and being in sheer agony from having her ass dry fucked like this. You could be a little more gentle with her if you wanted to, but you don't.