When I was in my early twenties I suppose I was handsome. There were plenty of people around that told me I was anyway. A group of married women where I worked thought I looked like one of those 'cuff and collar' male strippers, and they were convinced that was what I did as a side job. They were only half right.
I did have a side job, but it was as a personal fitness instructor, not as a stripper. Maybe those women thought I was stripper because, at least back then, I was in great shape. Maybe it was just their own wishful thinking. Who knows?
Because of my side job I didn't have a ton of time to go out, but I always tried to keep Wednesdays open. That was the night that the Cadillac Bar had the best happy hour I've ever seen. Admission and food were free... and drinks were half price. The food was amazing and they even had a guy carving prime rib to make little sandwiches. The Caddy, as we called it, was just a few blocks from my day job, and it seemed like half of the office would show up to this place every week.
That group of married women who were convinced I was a stripper never missed a Wednesday happy hour, and they always tried their best to sit at the same table I did. Then they would flirt with me and take turns asking me to dance while the others watched to see if I'd make any obvious stripper moves out on the dance floor.
After an hour or so these married women would leave and go home to their husbands. One of them always made it a point to try and kiss me before she left. I'd always tell her not in front of our coworkers. Then I'd wave goodbye as my little band of wannabe sluts headed out the door. After they left I'd typically save the table and wait for my friends to arrive. Then we would stay and party... some nights until the bar closed.
For a couple of years The Caddy was the hottest pickup bar in town, and it was on one of these Wednesday nights at The Caddy that I met a woman named Tanni. I'm sure her name was actually Tanya or Tannicia or something, but everyone simply called her Tanni.
I was as surprised as anyone when I found out Tanni was almost twice my age. All of my friends had her pegged as being in her early-thirties. She sold commercial fitness equipment for a living and without a doubt had the body for it. She claimed that someday she was going to be the oldest woman ever pictured in Playboy. If anyone could have pulled that off, it would have been Tanni.
Tanni was there at The Caddy that night with a couple of other newly divorced women, and this tall, dark and curvy stack of hotness named Sandy. Sandy wasn't the sharpest tool in the shed, but she more than made up for that in beauty. Sandy was also much younger than the other women... Probably only a couple years older than I was.
Tanni said the thing brought them together as friends was that they were all single. It looked to me like the three cougars had brought Sandy along as bait. It didn't seem to work the way they wanted though. All of my friends pretty much ignored the cougars and swooped in on Sandy like seagulls on a french fry.
Even though three of the women were quite a bit older than us, we still had a blast that night. We all danced and partied the night away, and when the bar closed down I found myself carrying Sandy out to Tanni's car. My friends had been buying Sandy drinks all night and she was in no condition to walk, let alone drive. The reason I was carrying her came from a bet of sorts.
On the way out of The Caddy, Tanni bet me that I couldn't pick Sandy up, and I'm pretty sure she meant I couldn't get her to go home with me. Sandy overheard this and immediately agreed with Tanni, then she smirked and dared me to lift her off the ground. Sandy had clearly missed the point.
So I playfully went along with Sandy's interpretation of the bet, picked Sandy up, and carried her to their car. When Sandy realized I wasn't going to put her back down she wrapped her arms around my neck and started nibbling and licking my ear. Tanni just stared at her young friend like she was a total cunt the whole way to her car.
The Wednesday after meeting Tanni was pretty much the same as every other Wednesday. I was there at The Caddy and my little band of married wannabe sluts had all gone home to their families. My buddies actually arrived early for once, and shortly afterwards Tanni and Sandy found us sitting in our usual place. So we made room and crowed around that one little table.
This time Tanni made sure she stayed between me and Sandy all night, and every time Sandy so much as looked at me, Tanni pulled me onto the dance floor and did this super sexy dance. Damn this Tanni woman was hot. She pretty much rode my leg every time we danced, planting her hot camel toe clad crotch on my thigh and rubbing it on me as we danced.
Just like the week before we closed the place down, and we all left The Caddy together. On the way out Sandy was hanging on me hinting we should take the fun elsewhere. When Tanni noticed what Sandy was up to she stepped in and reminded Sandy that she had to be up early to get measured for some beauty pageant. Then Tanni gave me her address and invited all of us to go to a party at her place that coming Saturday.
When Saturday came around my friends and I couldn't find anything else to do so we decided to try out Tanni's party. One of the guys had to work that day so we were running a little late. By the time we got there the party was in full swing. There probably 50 or 60 people there ranging in ages from their early twenties like us, to their mid-forties like Tanni.
Almost as soon as we arrived Tanni latched onto me and started parading me around, introducing me like I was some sort of prize. About fifteen minutes later some loudmouth douchebag named Alan showed up with a large vase, a bag of whole wheat, and a bag of regular flour. The douchebag seemed to have a huge crush on Tanni and he said, "Hey look, I brought you some flours."
It wasn't long before Alan realized that I was Tanni's prize for the evening and his crush turned to sulking. Then he sat with a bunch of older guys that must have been his friends. That's the group of guys that came up with the nickname of Chip for me. Those guys hated me, and it didn't take long to find out that Chip was short for a Chippendale dancer. To this day I have no idea why everyone seemed to think I was a stripper.
We were there for maybe an hour and my buddies started getting antsy. That had all come to the party hoping Sandy would be there, but she was at that beauty pageant. They stayed for maybe another hour hoping she would show, then gave up and left with a couple of Tanni's cougar friends to go to The Caddy.
My friends just assumed I would be leaving with them, but Tanni convinced me to stay with her at the party. It didn't take much convincing, getting into The Caddy on a Saturday night usually meant standing in a line that wrapped half way around the building.
The party finally died down, and douchebag Alan and his friends were the last to leave. As soon as they were out the door, Tanni kissed me and told me she wanted to make love to me, but I wouldn't exactly call what we did making love. Something got licked stroked or shoved into one hole or another on almost every stair on the way up to her bedroom. Then when we finally made it to the bed we took turns licking, sucking and fucking each other until well past 3:00. At that point we were both just far too exhausted to go on.
I woke up somewhere around 9:00 the next morning feeling somewhat used and abused. I reached over to Tanni's side of the bed and found she wasn't there. I slipped on my jeans and went to find her.
When I got to the top of the stairs I could hear Tanni talking. It sounded like she was on the phone, and there was no doubt she was telling someone all about our wild night of sex. My best guess was that Tanni couldn't help but rub the fact that she had seduced me in Sandy's face.
I just sat and listened for a while hoping the call would end and Tanni would come back to bed, but the call went on and on so I wandered down the stairs and stood in front of her. Being this close I could faintly hear the person on the other end of the phone asking Tanni some sort of a question. She just smiled at me and said, "Hold on and I'll find out."
