I took over running my dad's bar in the early 70's after he had a heart attack and couldn't work for awhile. I was 22
Had a lady begin coming in every Friday night and would always find some guy, usually an older male to take home with her. She was 59.
One Friday she came in and sat at bar while I was tending. She was attractive, a couple of extra pounds but not to the point that she would be considered fat and always dressed nice. It was fairly slow that my night so we were carrying on a conversation. Found out she was a widow and worked for a Federal judge.
She was wearing a shortish skirt, loose flowing blouse, hose and heels. The skirt was just short enough that it rode up on her thighs as she sat on the stool. As I said there were just a handful of folks in the bar, but a few guys, looked to be in their early 50's came in sat at the end of the bar and offered to buy her a drink, so I figured soon she would leave her bar stool and go join them. Well she did so I said to myself that those two guys are going to have some fun tonight. I closed at one AM and to my surprise about 12:30 the guys left and she moved back to the stool near the middle of the bar.
Near closing time there was no left in the bar except her and I. I ask her if I could buy her a drink, she accepted so I said it's after one I needed to lock up and she said she would leave after she finished her drink. After I got everything secure I made me a drink and sat at a table near the pool tables. She came over, joined me and sat facing me.
She had a decent buzz on and kept adjusting her seating in the chair, her skirt was riding up and soon I could see she was wearing no panties. After a bit she began crossing her legs and I look between them and she saw me looking stopped mid cross, and ask if I like what I saw. Of course I said very much so and she stood unzipped her skirt and stepped out of it. Standing in front of me she bent at the waist, undid my pants, I stood and she removed them, got in her knees and to my now hard cock between her lips. The bar was dark except for a couple of neon signs. Damn she looked so good squatting there in front of me with my cock getting a great sucking. She sucked on me till I told her I was near cumming, she stood and I guided her to a pool table, she laid on her back and spread her legs wide. Getting between them her pussy was about dripping as I began lapping at her pussy and damn did it taste sweet. I climbed on the table got into a 69 with her. She had two hard orgasms and she took a load of my cum down her throat but kept sucking and got me hard in no time. I climbed off the table, helped her off, bent her over the table and entered her doggy. We fucked for what seemed like ages, she came a few more times but I had cum in her mouth shortly prior so I was not near ready to cum again so she turned around, got on her knees, and started sucking me again. I was as hard as I had ever been in my life and pumping her mouth and down her throat deep.
She stopped sucking me and I thought we were done but she stood up turned to the table and said I really like that you have a longest thin penis and I love anal sex, please fuck my ass. She bent over the table I got behind her dropped down and began tongue fucking her, she was pushing her ass into my tongue and letting out a soft coo. I stood, rubbed my cock over her ass and pussy, pushed my cock in her very wet pussy then placed it up to her asshole, trying to go slow she immediately pushed back on my cock and took me totally deep. I just stood there as she just pushed it all the way in and then back off till just the head was in them pushed back deep again. This went on for a bit and I grabbed my cock and began rubbing it on her pussy and ass, soon she was squirting all over my legs and on the floor, I dropped to my knees and lapped as much of the squirt as I could swallow.
We continued this routine for about 8 months, she would show up on Friday, dressed to the hilt, always no panties or bra. She would allow guys to buy her drinks and if she liked them she would go out to their car and give them a blow job. Then come back into the bar till closing time, then it was my time. Never met a woman who enjoyed anal sex like she did.
