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Amateur Night

This happened many years ago with a girl I dated briefly. I ended up being transferred and moving to another state and often wonder what would have happened if we had been together longer.

To set the stage, this girl was a slut (and I mean that in the nicest sense). She absolutely loved sex and could wear me out (which was not easy to do back then). She was also up for just about anything. She was the girl who couldn’t say “no”. Her name was Allison and she was probably the most open person I had ever met. Shortly after we met and became intimate I asked her about her sexual experience. I was amazed that a 23-year-old had that many stories to tell AND that she would tell them to me.

Over the next few weeks I heard about; her and her Father’s business partner (he was 42 and she was 18), the first time she did it with a girl (a fellow high school cheerleader), the time she did three guys at once in a college dorm room, and more.

I decided I had to fully explore the possibilities when dating a girl like Allison. She would never suggest any scenarios, but was always open to my ideas. One Saturday night I asked if she wanted to get dressed sexy and go out. Of course, she agreed.

I went over to Allison’s apartment and she agreed to let me pick out her outfit for the evening. She had an extensive collection of lingerie and some sexy outfits. Prior to our dating, she had dated an older businessman who liked buying her outfits and then having her model for him. Most were only for the bedroom, but he also bought her a nice selection of tops, skirts, and heels.

Allison was a short girl (around 5’3”), what is usually described as “curvy” (she is most likely heavy now, but as a 23-year-old she had some great curves). But, the feature that got her the most attention were her 40 E breasts! They were huge and she had large nipples that would get rock hard when she was turned on (which was most of the time). Her breasts were very large and looked even larger on a short girl.

I started by picking out a red panty and garter set with a matching red shelf bra. Allison’s breasts were surprisingly not saggy, but the shelf bra just made them impossible to resist (or miss when she walked in a room). I had seen her in one before and knew she would look amazing. She added some black stockings and heels. I then picked out a short skirt that had a slit up one thigh. She then pulled out a white, button-down shirt that I wasn’t sure of. However, when she put it on it became a mid-riff with a couple of inches of belly showing when her breasts used up most of the material going out rather than down. I added a scarf tied as a choker and the completed package looked like the slutty school teacher of my dreams.

She looked so hot walking to my car, I thought I might have to fuck her right there in the parking lot. But, I had other plans. I told her I had a surprise, but would not let her know what it was. I had planned to start with dinner and as I drove she wasted no time in pulling me out, leaning over and blowing me the whole way to the restaurant. I got a kick out of seeing some teenage boy’s eyes get big as he saw the back of her head going up and down in my lap while we sat at a stoplight.

I had picked a nice steakhouse and watched as every man in the place turned to watch Allison walk to our table. She seemed oblivious to all the attention her outfit and her body were receiving. We spent the next hour or so getting the absolute best service imaginable. The busboy almost never left our table as he stared down Allison’s top. I had fun rubbing against her nipples as I reached for bread or pointed something out. Her white shirt did nothing to hide their hardness. She would also make a point of bending for something when the waiter came over, giving him a nice view down her top. I knew she loved it and that her panties were surely already soaked.

When we returned to the car she begged me to fuck her right there. But, I had other things in mind for her that evening. As I drove she leaned her seat back, lifted her skirt and spread her legs. I knew that all of the teasing in the restaurant had gotten her hot and she needed to get off. I pinched her nipples as she played with her pussy. We had not gotten 5 miles from the restaurant before she moaned and twitched in her first of many orgasms of the evening.

When we reached out destination Allison smiled wide. She had admitted to me that it had been a long-time fantasy of her’s to go to a strip club and I had pulled into the parking lot of Diamonds Men’s Club. I had done some research on the various strip clubs in town and this one rated high, especially for couples. There were rumors that swingers came there, but nothing I could confirm.
Before we got out of the car, I reached over and unbuttoned two more buttons. Her breasts were now hanging out of her top. Rather than voicing any objection, she just smiled and pushed them together.

We paid our cover charge and entered the club. The club was not too large, but there were two stages, both with tables around them with booths toward the back. I noticed that there were 3-4 other couples on the right side of the room, so I steered Allison over to an empty booth on what appeared to be the couple’s side.

We spent the next hour drinking and watching the strippers as they took the stage. Allison would comment on the various women and tell me which ones she would like to eat (pretty much all of them). I even got a couple of lapdances for her. She was a little frustrated because she kept trying to touch the women, but they gently told her that was against the rules.
At this point we heard the DJ announce there would be an amateur strip contest starting in 30 minutes. The winner would receive $100. We watched as a couple of the women in the crowd walked over to the DJ booth to sign up. I smiled and gently pushed Allison out of the booth and she walked over to sign up.

She came back and told me there were three of them signed up. The other two had gone to the back to change, obviously experienced with the contest. She said even though she was not going to change, she needed to head back there before the contest began.

After she went to the back I watched as they stopped the music and an announcer got on the stage closest to my seat. He said there would be three participants that night and the winner would be decided on crowd reaction. Most of the guys who had been around the other stage moved over so there were now probably 40 men crowded around.

The announcer introduced the first amateur and music began to play. The first woman looked to be in her late 20s to early 30s. She was a redhead with perky tits. She was wearing a matching bra and g-string, with a sheer skirt and some killer high heels. She danced for the next two songs, removing her bra and getting a very favorable reaction from the men.

When she was done the second woman came out. This woman was older, probably in her late 30s or maybe even her early 40s. She had blonde hair and looked like a PTA Mom. She was wearing a bright blue teddy and high heels. She had a nice set of 34 Ds and strutted and smiled as the men whooped. This woman looked like she had done this many times and obviously got off on the men’s reaction. She quickly pulled down her top and unsnapped her crotch so she could expose her shaved pussy. Even though nudity was not allowed for the regular dancers, they seemed to be more lax with the amateurs.

When the second song started, she moved out into the crowd. She started with her husband. She gave him an incredibly erotic lapdance and everyone could see how hard he was as she rubbed him all over. Before her time was up she had given brief lapdances to another 4-5 of the men, rubbing their crotches with her breasts and ass, and even grabbing one man’s obvious hard-on. The crowd went crazy as she waved and left.

Allison was up last. I was not sure how she could top that woman’s performance. She came out wearing the outfit she had worn the entire evening. The first song she had picked was slower than the others we had heard for the other dancers. She danced slowly and erotically. She circled her leg on the pole, licking her fingers as she unbuttoned the few remaining buttons, setting her giant tits free.
The men sat watching in amazement as she slowly swayed and worked all around the stage. The men were practically drooling as they dreamed of sucking her hard nipples, now sticking out a full inch. She would lick her fingers and then pinch a nipple as she looked first one man then another directly in the eyes. She was managing to seduce a whole room full of men.

The second song came on and it was faster. She took the opportunity to go out in the crowd. She wold go up to a man, straddle his legs and move her tits into his face. Sometimes she would grab his hand and move it under her skirt. I knew that those men must be feeling a river of wetness. I could tell she was extremely worked up. If she had been given a third song, I am pretty sure she would have blown one of the men in the audience.
When she was done, the crowd went crazy. Most of the men stood up to applaud. The announcer brought all three women back on stage and had the crowd cheer for them one at a time. Although the other two women got nice ovations, it was no contest. In a few minutes Allison was back at our booth with a hundred dollar bill.

We had just ordered a new round of drinks when the manager came over and introduced himself. He said if Allison ever wanted to dance professionally at his club to let him know and handed her his card. We both laughed .
As our drinks arrived the woman who had danced second approached our booth holding her husband’s hand. She asked if they could join us for a drink? We agreed and they sat down.

She was Pat and his name was Stan. Pat was still wearing her teddy and merely smiled when my eyes kept moving to her breasts barely contained by the lacy material. We came to find out a lot about Pat and Stan.

They were regulars at the club and came every other weekend when her ex had her kids. She had entered the amateur contest 6-7 times before and won a couple of times. She said the first girl who danced was not a regular and had not entered before. As some of the dancers and waitresses came by it became apparent that Pat and Stan spent a lot of time there. They seemed to be on good terms with everyone and we got a couple of rounds of free drinks.

As the hour got later, Stan explained that due to the liquor laws in the county the club had to close at midnight. However, they lived close by and usually had a few people over after hours. They asked if we wanted to come and we agreed.

We followed Pat and Stan to a very nice house about 5 miles from the club. They gave us a brief tour and then lead us to the basement. It had a big rec room with a bar, pool table, and a hot tub on the patio. Stan made us drinks and we chatted for a while. Before long many of the people from the club arrived in the basement. I watched as 4 of the strippers came downstairs. A couple of them brought boyfriends. In a few minutes one of the male bartenders arrived with a female bartender and a waitress.
Everyone seemed to feel very comfortable and one of the bartenders hopped behind the bar and made a round of drinks. We watched from the couch as people played pool, played video games on the big screen TV and continued to drink the seemly endless supply of booze.
Stan came over and asked if we would like to use the hot tub? I declined, but Allison seemed interested. She confessed she did not have a suit to wear, but Stan reminded her everyone there had seen pretty much everything she had to offer. She laughed and followed him out to the patio. Not surprisingly I saw as a couple of the men quickly made their way as well.

After a bit I decided to see how Allison was doing. I went out to the patio and found it quite dark. I made my way over to the hot tub, with the only lights being the ones in the tub. When I got closer I could see Allison was in the tub as three men sat on the edge. She was in the middle of the three with his cock in her mouth while she stroked the other two. I watched as she moved between the three keeping them hard. Stan was sitting on the opposite side of the tub when he noticed me. “I hope you aren’t the jealous type.” He said.

“That would be hard when dating Allison. As long as she is having fun, I am okay with it.”

“That is good to hear. She got a lot of men going tonight, including me.” Stan replied. I watched as he stood revealing a rock hard 10 inch cock. He may have been a little older, but he was packing some meat. He moved behind Allison and I heard her moan as he slowly entered her.

At that point I felt a hand on my ass and turned quickly. Behind me Pat was smiling as she held the hand of one of the strippers. “I knew Stan would be the first to fuck that girl. “ she smiled. “Make sure you don’t keep her to yourself all night,” she yelled over my shoulder.
“Since your girlfriend seems to be occupied, why don’t you spend some time with me and Crystal.”

Crystal looked very young, no older than 20. She was bleached blonde with long hair, and was wearing a jeans skirt, heels, and a bikini top. She was small breasted, but her nipples were poking through the bikini material.
I followed Pat as she held onto Crystal’s hand and lead her to a room off the main rec room. It was a small bedroom and pat gently pushed Crystal onto the bed. She turned and told me to strip and I watched as she got down between Crystal’s legs, moved her panties aside and began licking her. It was not long before Crystal was moaning loudly. Since Pat had left the door open, several people drifted to the entry to watch the action.

After Pat had brought Crystal to a screaming orgasm she grabbed my hand and pulled me between them. I spent the next 30 minutes taking turns first fucking Pat, then Crystal, then Pat. Whoever was not getting fucked would be kissing me, or licking the other woman. I even had one of the female waitresses come in and play with my ass while she kissed me, all the while I was buried deep in Crystal. One of the guys at the party took her hand and I could see as the fucked on a couch out in the rec room.

When we finally got done I went back out to the patio to try to find Allison. The hot tub was empty but I could hear her moans coming from a corner. I made my way in the darkness and found her on a couch, riding one man while another was fucking her ass from behind. She was sucking a third who was standing on the couch. It seemed everyone but me was getting a turn on Allison that night. I knew it would pay off for me because she would be insatiable for the next week.

I made my way back to the rec room and ended up fucking two more women before the night was done.
Allison and I went back to that strip club a few more times, and once went back to Pat and Stan’s for their after hours party. It was a time in my life I would love to repeat.

End of Story