It had been a typical Wednesday night at the bar. A few regulars sat at the bar stools slowly drinking themselves into a stupor after a day’s work or whatever they do before they come in. A random table of coworkers still dressed in business attire drank their gin and tonics and laughed periodically throughout the night. There were a couple of ladies, maybe old friends reliving their younger days, who sat at the end of the bar who kept calling for my attention asking questions about women, sex, or whatever they thought could embarrass me with. They really didn’t faze me too much; I would flirt back every now and again or maybe fake a blush because I needed the tips. Other than that, it was pretty slow.
I had just graduated from college, and bartending was about as good of money as my friends were making, plus it provided some interesting stories and more than its share of ladies. I had bartended all through college, and pulled more than my fair share of pussy. This place was a little slower though. Besides the bar waitresses, there wasn’t a whole lot of young and fresh faces to look at. About an hour before closing I stood smoking a cigarette, almost ready to start my closing chores early so I could get out of the place at a decent time and was thinking about getting a job at one of the clubs downtown. The hours were later, but better money and more women were the upside and I have my priorities.
One guy had come in by himself earlier in the night and sat in the far corner, slowly drinking his vodka martinis, slightly dirty and slightly dry. He was dressed rather well, and by his taste in drink and his tipping I found it rather odd that he was by himself at this place instead of going to a place where there was a little more action. Regardless I didn’t mind his business on a slow night.
I began stocking up beer for the next day and noticed him watching me. It was a little weird but I went about stocking and breaking down the boxes. At last call he came up and ordered another drink.
“Another Grey Goose martini bartender,” he said as he sat down, reaching for an ashtray.
As I poured the vodka I said to him, “This is actually my favorite drink, to make and drink.” I figured I’d strike up a conversation since the guy was by himself and was tipping good, plus it gave me a reason not to check up on the ladies down at the end who by this time where getting a little more drunk and upfront with their comments. If they were about ten years younger and ten pounds lighter I might have offered them a ride home and see were that would lead, but for now I was going to figure this guy out.
“Same here,” he said while taking the first drag of his cigarette. “I can only drink a few though, even though they go down like water.”
“Well, that’s your third so you might want to watch your way home so you don’t get pulled over,” I said while putting the bottle back.
“I need the extra courage I guess. I’ve got a little situation and it’s a little hard to bring up to someone you don’t really know,” he said while taking his first sip of the drink.
I really didn’t like where this was headed. “Extra encouragement” and “Situations” might be okay if it is some blonde with blowjob lips and fuck me eyes, but not for guys. I decided to cut to the chase on this one, “What’s the situation?”
“Well, me and my wife have this fantasy and we need your help,” he said taking another drag off his smoke and putting it out little over half finished.
“Hey buddy,” I interrupted, “I’m not really down with any funny stuff. I mean, I’m straight.”
“Good.” He said, “I’m not asking you for a threesome. My wife has this fantasy of fucking a stranger and she asked me to pick one out for her. That’s why I was kinda checking you out, you are an attractive guy and I’m sure bartending has given you some experience so I know you won’t disappoint. The only catch is that I get to watch, out of your way but still being able to view. I’ll even pay you.”
I’m not above taking a few extra dollars for my services, might as make some money, but the fact that he offered money made me a little skeptical. His wife couldn’t be all that if he was putting up money for extra incentive. “I’ll tell you what, bring me a picture and I’ll consider it.”
He smiled at me and reached inside his jacket, pulling out a Polaroid. Flipping it on the bar upside down. I picked it up, turned it over, and almost lost it. Keeping my composure I put the picture back down on the bar and said I would gladly do it and had tomorrow night off. He wrote down the address on the back of a coaster and said be there around eight.
After that, it was time to close so I excused myself and went about getting everybody to finish the drinks and out the door. Turning the lock, I went over to my bar waitress and said, “You are not going to believe this, but that guy offered me money to sleep with his wife.”
“Are you going to do it, is she hot?”
“Yeah, and she is one of my old high school teachers!”
I couldn’t believe my luck. Some horny wife sends her husband out to find a stranger to play out their fantasy and spice up their sex life, and it turns out to be Mrs. Scott. Mrs. Scott had been a constant fantasy of mine my senior year when I had her for Spanish class, hell, she had been every horny teenager’s fantasy, probably most of the male faculty as well. She was tall, maybe about 5’ 8’’ with red hair and major curves in the right places. Her beautiful face was highlighted by full lips that were made to suck cock.
When I flipped over the picture and saw her lying back on a bed, her legs slightly spread to give a hint at her red pubic hair and her hands lifting up slightly on her 36C breasts I almost came right there. She looked a little older, it had been about five years, but she was every bit as gorgeous as I remembered.
I kept replaying the image over in my head while driving home. When I got there, I had to relieve myself and began jerking off remembering how she would bend over in front of my desk, her ass in perfect view. Or how she would lean over my desk when I would ask for her help, her blouse coming down to reveal two perfect white globes held back by her lacey bra.
I had trouble sleeping that night. I mean, I had numerous sexual encounters with beautiful women, had plenty of good sex, but nailing the teacher of my early sexual desires was in a league of its own. I drifted off thinking about all the nasty things I was going to do to Mrs. Scott.
I arrived at the house at exactly eight the next night freshly showered and ready to fuck. The husband answered the door and invited me in. We went into the kitchen and he made a couple drinks. He asked if everything was still okay and if I had any questions before I began.