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By Cheryl (cjr34@hotmail.com)

Halloween weekend starts on October 27th, a Saturday, and time for another night out on the town. This night I had decided to go to the Pimps and Ho's celebration at the Metro club. Now this club is sort of in the heart of the gay and lesbian community but not restricted to members attracted to the same sex only. In fact they pride themselves on their ability to attract members of all sex preferences and color.
The celebration is about dressing up as pimps and the girls of the night and of course there is a contest at the end of the night for best outfit for both men and women. I had an outfit in mind and called up a girlfriend who I've had personal fun with in the past to go with me and she was all for it.
Naturally a night out to a place and event like this called for a severe hooker's outfit and after a few minor modifications I had my outfit ready. My girlfriend Mandy arrived on time and if I had seen her on the streets with the other working girls I would have wasted no time connecting with her cause she looked the part. But enough about that slut ha ha, I am here to tell you about me and my outfit.
I have several skirts that are about ten inches in length from hem to waist and I had altered one of these skirts so that it was no more than 7 inches long which meant on me it had to hang way below my belly button to barely even cover the cheeks of my ass.
I had on under the skirt a very tiny g-string barely an inch wide and four inches long, which means it ended in the vicinity of my pussy and the string up the back disappeared into the crack of my ass. I had also taken one of my old tube tops that had been 7 inches wide and cut off 3 and « inches and after hemming the loose material it was now a three inch tube top. Three inches is not a lot of material to cover my 34d breasts nor was a 7 inch long skirt long enough to conceal my 35 lower measurement but keep in mind we were supposed to look like hookers.
I also put on my over the knee white stockings that came to about 4 inches below my skirt so I had some skin exposed between stocking and skirt. A pair of 5 inch gold heels completed the outfit except for the overdone makeup, which really made me stand out.
Once inside the club we separated as agreed both of us hoping to get lucky and I have to admit she is as much a good time girl as I am so I knew we'd be seeing each other through out the evening just to check in on each other. I wandered around the large club for awhile and then ambled back towards the pool tables in the back and while I love to shoot pool and I am no good at it despite the efforts of my husband who at one time considered turning pro.
I was standing there by myself watching the would-be hustlers and wishing my husband were not in Washington D.C. on national business. I was not alone for long when a large black man dressed like super fly (if you've seen the movie you know what I mean) came over and offered me a drink and settled himself down next to me making small talk. He asked me about my outfit and I told him I was supposed to be a streetwalker keeping in theme with the evening.
He said since he was a pimp and I was a lady of the evening, would I consider acting the part for him and making us a duo at the party. I saw no problem with that so I said yes.
Acting as his 'ho' I was the one who had to either go for drinks or pay for them when they got to us and I had no problem there either since drinks were half price for all in costume.
During one of his pool games he came over to me and said I should sit more hooker like on the bar stool in hopes of distracting his opponent and I knew what he wanted so I did it. I sat perched on top of the bar stool with my legs open and my g-string easily on display for all to see. Of course my man won the game and he came over and gave me a lip lock in congratulations.
About four drinks later and a lot of money later that he had won he was feeling cocky and took a break and sat down beside me and we chatted some. He asked me how much of into pretending I was really in to and I told him test me. He said, "Well, you know all good pimps check out the goods personally before offering his girls up for the public," he smiled and waited for my response.
I knew what he was after, and after all we had been talked about it for the hour and a half and he seemed kind of cool. So I think I freaked him out when I said, "Lets go outside so you can check out the goods then." I smiled at him and stood up and grabbed my little handbag and started walking out the door. Sure enough he was right behind me acting the role with his exaggerated pimps walk.
In the parking lot I leaned against a car just outside the door but far enough away the bouncers couldn't see us. He leaned up against me and gave me a lip lock and started feeling up my tits which weren't all that concealed. He began a soft pushing down motion on my shoulders and I knew what he wanted and went to my knees and unzipped him and pulled out his long cock. It wasn't all that thick but had to be ten inches long when my mouth was through encouraging it to grow.
He then stood me up and I leaned over onto the hood of the trunk and he spread my legs a bit and in one motion he entered my hot wet tiny pink pussy and buried himself balls deep and it felt so good. He pulled down my tube top and used my tits as handles that he squeezed hard to pull my body back onto his cock and it felt so hot.
When guys walking by to go into the club made comments, some even stopped to watch. My pimp fucked me in the parking lot for about fifteen minutes. Finally he moaned that he was going to cum, did I want it inside my cunt or my mouth?
I told him he could choose since he was the pimp. He wasn't going to pull out and he kept banging me really hard for another minute, then he shot his baby making cum deep into my belly.
After a few minutes rest he pulled out and told me to clean off his cock. So I knelt down in front of him and used my tongue and mouth to clean all of my juices and his cum from his dick.
Than he told me that I had fucked up. I asked him what he meant. He told me that a hooker always has a supply of condoms for the johns. I told him that he wasn't really a john. That is unless he was going to pay me.
He smiled at that and said, "You're right," and with that I wiped my thighs clean of his cum and licked his my fingers clean, and then we both reentered the club.

I was now totally into the role of hooker. I made a big show of smacking my chewing gum and chain smoking (like I hoped a real hooker would) and I was talking loudly about "my man" and just having a good time showing off my body to the guys hanging around.
I even made one guy lose a pool game by my blatant display. When he lost he paid up the ten bucks to my pimp and then he came over to me while the next challenger got ready. He was drinking a miller's out of a bottle and finished it while he stood near me. Then after eying me, he turned to my "pimp" and said, "Since your lady friend here cost me a game I have another bet for you."
We both looked at him like "what are you talking about." Then he said, "I have twenty bucks (which he slapped down on the tiny table) that says she can't do my bottle."
I looked at him and started to say, "What do you mean do your bottle?" but I never got finished. My "pimp" spoke for the both of us, "Of course she can, man." I guess after taking his ten inches plus up my cunt outside he had all the confidence in the world in me.
I still wasn't exactly sure what to do with a beer bottle, but I was beginning to get a good idea when the guy drained it of beer and handed it to me. My pimp leaned over and told me what I had to do and thank god I'd done this a few times before at home so I figured I could do it.
I thought we'd go outside again but no one moved. I told the guys to gather close around me because I didn't want to cause a problem with the bar owner, and they formed a wall male bodies all around me.
I licked the bottle seductively trying to get it extra wet and then I stood up on the lower rungs of the bar stool and placed the bottle under my g-string and then I pulled it aside and started to slide it into my pussy and when I knew it was about halfway in I slowly sat down and the bottle disappeared into my cunt and filled me up. My cheeks were flat on the seat and there was no doubt the bottle was all the way up inside me.
The guy handed over the twenty and said it was worth it and walked away. Several other guys had witnessed this event and my pimp told me to just sit there with the bottle inside me for a while. Know what I really dreaded? Taking that monster out of me because it felt like I was so full and stuffed with a large cock inside me as I sat there watching them watch me. It felt so cool to see their lust.

Later on, after our private little party broke up I found my girlfriend making friends with two guys who looked "safe" if you know what I mean. She told me she was going home with them and that she would call me later to tell me how it went.
Now all by myself, I went back into the bar and to the pool tables and resumed my seat and waited for whatever would happen to happen. I was pretty buzzed and feeling very horny by now and probably would've done anything I was asked at this point.
I was a bit surprised though when my "pimp" said he had to go, and just like that he left me there alone sitting there by myself. Turns out his wife showed up and he had to go sit with her and her girlfriends before any connection could be made between him and me.
You know what all good-looking party girls say? How guys are usually too shy to make a move because our looks scare them off? Or how guys don't make a move till they think they all look like Tom Cruise?
Well, that's what happened to me. I stayed alone back there for half an hour and no one even came close to me. By closing time though I was surrounded by guys who couldn't even say their names right without slurring the words. My only salvation was when I got home that night my girlfriend was there waiting for me with her two studs.
We ended up in a fuck-a-thon till dawn. All in all the night was pretty damn exciting although I wished it had turned out a bit different.
Oh well, Halloween this year is the 31st and I'm planning on going to the fetish ball and will tell you all about it.
Love and kisses, Cheryl.