Working Day
Keywords: Day, Working,
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Kelly had told her that she would meet her here in our room later. The problem was that Amy was only interested in Kelly one on one. Kelly had wanted to try sex with a woman for a while but never had the opportunity. Dressing me up had been a substitute for the real thing. I was feeling disappointed about being left out and replaced but Kelly assured me that I wasn't being replaced. This was a one in lifetime chance for her and I wouldn't stand in her way. She also told me that she would tape the tryst for me so I could watch it after. I hoped that I had brought enough blank tapes.
Now I had to figure out what to do myself. I was feeling very confident about my ability to pass as a woman and was confidant enough to try something more. I told Kelly that while she was entertaining her masseuse Amy, Mary-Ann would make a solo trip to the cocktail lounge. I rummaged through the items of clothing in the second suitcase and selected some choice items. I started with a black garter belt and black fishnet stockings. Next were black thong panties and a black corset. I selected a silk red Chinese jacket that had dragons embroidered on it. It matched the cocksucker red lipstick, and nail polish I was wearing. The collar was high, the sleeves short and the fit was very snug but it looked fantastic with my black hair. I selected a way too short black leather mini skirt that had a little slit over one thigh and a pair of paten red platform stripper shoes. I added the appropriate gold accessories and black choker to complete the look. After I had finished dressing and finishing my makeup and hair, I modelled for Kelly.
"So, how do I look?" I asked.
"Like a hooker!" Kelly replied with an expression of disbelief on her face.
I smiled proudly, "Good! That's the look I'm going for."
Kelly and I wished each other luck and I ventured off on my own as Mary-Ann to the hotel lounge. Not surprising, I was greeted with many glances and shocked expressions as I entered. After getting myself a Cosmo, I was again told that it was taken care of. The bartender pointed out the same group of gentlemen from the previous night. I smiled and seductively sauntered over to their booth to join them. They were all in agreement that I looked fantastic. I always knew women dressed too conservatively. One of them asked where my friend was in reference to Kelly.
"Back in the room with a migraine I'm afraid," I said. "Looks like you will have to settle for just little ol' me tonight." They didn't seem too put out by that and Brian was first to drag me to the dance floor. As I danced with Brian he aggressively fondled my very popular ass. He pressed his body close and I could feel his bulge rubbing against me. After that dance, Richard took his place. The story was the same as it was with Martin and David who fallowed, each feeling up my ass and rubbing themselves against me. At the end of each song they would give me a little kiss. After they had all had one dance, they rotated through again. The story was the same with the addition of some kisses on the neck and cheek. It was definitely getting steamier. All four of the men seems very interested in me and my early departure from the night before appeared to be forgiven.
The dancing was tiring so I took a break for a drink. Soon Brian was bugging me to go back to the dance floor with him. My feet were really killing me in those shoes. I didn't want to be a party pooper again so I jokingly asked, "How about a nice lap dance instead?"
Brian's eyes lit up. "Sure, great idea!" he spouted. What had I got myself into? Brian pats his lap indicating for me to sit down. I carefully sat on his lap keeping my knees together so that my male parts were safely between my thighs out of any possible contact. Right away, I could feel Brian's erection through his wool pants and my leather skirt. The other four gentlemen watched intently as I began moving my hips in time to the music, grinding on Brian's lap. The tablecloth hid everything happening below the waistline from view of other patrons and the staff. Brian began feeling me up all over my legs. I had to divert his hands from my inner thighs a couple times. I took hold of them and moved them to my boobs. He enjoyed the feel of my fake tits. The silicone gel made them very realistic to the touch. My silk top provided a good shield from his curious hands. It began to get very erotic and my bum was feeling hungry again. I then did something that still amazes me. Right there, at the table, surrounded by people, I reached back and unzipped Andy's fly. I reached inside and pulled out his stiff member. I pulled out a small bottle of hand cream from my purse and put some in my palm. I rubbed it up and down the shaft of Brian's cock. My skirt was so short that I only needed to slide my panties an inch to the side to expose my asshole. I positioned his cock at the entrance to my tunnel and eased myself down on it. The fucking that I had taken earlier from Andy made it not too difficult to insert. I was still tight enough and hot enough to make Brian groan with pleasure.
"Am I in your ass sweetheart?" Brian whispered to me. I nodded. "God damn! I've never done that before," he added. I tried to move my hips and flex my ass cheeks just enough to not create a scene but still stimulate the cock inside me. It was working and in short order Brian was filling my bum with his liquid love. I was ready to excuse myself but David, sitting next to us, had already taken out his big cock and was pulling me to his lap.
I repeated the lap dance, getting my bum fucked again as I ended up doing for all four of the men. During my last lap dance with Martin, I felt Richard slipping something into the top of my stocking. I didn't bother checking to see what it was at the time. By the time Martin at the end of the line was finished blasting his cum inside my worn out rectum the bouncer of the club was standing next to the table. The large, muscle bound man did not looked pleased.
"Ma'am, I'm afraid I am going to have to ask you to leave," the bouncer, with his chiselled face framed by a brush cut, informed me. He must have thought I was a hooker. The guys looked a bit embarrassed and quickly scattered from the bar. The bouncer escorted me out the back way so not to disturb the other guests. As we stepped outside into the back alley the burly man said, "Sorry lady, not my idea, the manager made me do it. It looked like a lot a fun to me. No hard feelings hon?" He was smiling. I smiled back and grabbed hold of his crotch. His cock was already stiff as iron.
"Well, at least one hard feeling," I answered. He paused, and then undid his pants, releasing his tool.
"Ok lady, make it quick, I gotta be back before I get in shit," he told me very business like. Suddenly, I was a whore. I found myself kneeling in the dirty ally, giving a blowjob to this guy who just threw me out of the club. There was no romance involved. He held my head in place and fucked my face as fast as he could. He took fast hard stokes at my mouth. I was choking on many of the thrusts but he didn't care. In five minutes he spurted his load down my throat. He didn't give me any choice about swallowing or not. He had a firm grip on my head as his balls pressed against my chin. It all went down. Then he was gone, back into the bar. I was still kneeling there, catching my breath. I felt so cheap, but only for a minute. I found the item that had been slipped into my stocking. It was a roll bills adding up to five hundred bucks.
"So, I'm a whore!" I announced to Kelly as I entered the room. Kelly's date had left a little earlier. My wife was lying on the bed, wearing a tiny black teddy, waiting for my return. She demanded to know the details and I told her everything. She was excited to hear about it and when my story was over she told me to climb on top of her and sit on her face. Kelly eagerly ate my ass out for the next hour while I watched the video of her and Amy making love.
The next morning we agreed that things had got out of hand and we needed to take a step back. We didn't have any more excitement like that for the rest of our trip. When we got home we decided to go back to our one night a month theme night but we added another day to our monthly rotation. We haven't got a name for it, but I dress up as slutty as possible, Kelly takes me down town and drops me off in party district while she heads to local 'ladies only' club. The next day we share the details of our respective adventures and add up the money I come home with.
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Keywords: Day, Working,