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Sissy Stories: Fun Times at Halloween - Sissy maid

 'Fun Times at Halloween'

It was almost Halloween and I was stumped for a costume. I was excited, tonight was the annual Delta Kappa Halloween Bash, the biggest fraternity party of the year. All the Greeks got dressed up for this party, even those not in DK.

I headed down to my friend Kathy's room to see if she could help me figure out a costume. Kathy was in a local sorority and was also planning to attend.

I showed up to her dorm room and told her about my problem, that I had no good ideas for a costume. I wanted something fun, but stuff like fireman, or policemen were sure to be used.

She told me that one of her sisters had canceled on her and that they had planned to go as french maids together. She had picked up two identical costumes and had them in her room. She then shocked me by asking if I'd let her dress me up and see if she could make me into a convincing woman for the night.

Kathy was a good friend and I had borrowed some of her clothes for a themed cross dressing mixer we had with another sorority, so I figured what the heck. It wouldn't be much different than that and all the brothers in my fraternity had seen me somewhat dressed up before since they were all done up that night too. I was sold.

Kathy and I had hooked up before so I had no modesty in her presence. She told me to strip and I did as she asked. She then threw me a towel and we headed for the girls bathroom to shower together and take the necessary grooming steps to make the costume work. Forty minutes later and with a lot less body hair, we were back in her room applying makeup and nails. She was planning to go incognito and had purchased a brunette wig to cover her blonde hair, so she fastened that to my head instead. I'm not exactly sure how she did it but after she applied the makeup, the nails, and the wig I looked in the mirror, I would be not only be passable for a college-aged girl, but I thought I looked pretty hot.

Next, she started fishing through her lingerie drawer. She pulled out two small black g-strings and black lace bras. I just gave her a quizzical look and she said to roll with it. It was her show, so I did what I was told and put on our matching lingerie, tucking my average sized equipment away as best I could. She had insisted on leaving me a little patch of pubic hair in the shape of a triangle above my cock, but everything else from the waist down was gone. She added some inserts to the bra and gave me a little bit of cleavage, not too much, but enough to let me have a nice B cup. She wanted to keep an edge with her nice C's since she figured guys would be somewhat attracted to her leggy brunette friend.

She then opened up the costumes and helped me get into mine. Thankfully her sister was a tall girl because otherwise it wouldn't have been able to cover my 5'10" frame. Thankfully too I had been a cross country runner in school and was still very slim. She added the finishing touches with fishnet stockings and open toed 2" shoes that I somehow made work.

I took one last look in the mirror at two women, one 5'9" and one 6' tall, both wearing black fishnet stockings, black ruffly dresses, black chokers, and sexy makeup. All in all, she made me look much more feminine than I had looked for our mixer and I thought that this might actually work.

We started to head down to the DK house and she had me practice a lighter voice while we walked. She said I was not to reveal myself to anyone so she could test her handy work. We got to the house and there were people everywhere. About this time, I started to feel pretty weird but followed Kathy inside.

We paid the cover and headed toward the bar. I definitely needed a drink. The bar was downstairs, and as we entered, I remembered the lighting inside the house was going to be set for Halloween, which was darker than normal. I started to feel pretty confident that I was going to be able to pass as a woman in this kind of environment. Kathy held my hand as we made our way to the bar.

We got to the bar and were fed drinks by one of the Kappa guys. He introduced himself as Red and asked if we'd be interested in doing some 'cleaning' for him later. Kathy laughed and said she'd have to see to the dirtiest people first. Red, who was about 6'2" and pretty well built, just gave a devilish grin to that.

We took our drinks and backed away from the bar. I took a sip and noticed I left a little lipstick on the cup. We were just swaying to the music and laughing at some of the ridiculous costumes when a young looking guy in an orange jumpsuit came by with shots. I guess the orange jumpsuit guys were pledges as this one said he had the first 'installment' of payment from Red for cleaning services to hopefully be rendered later. Kathy grabbed the shots and thanked the pledge. She figured free drinks are free drinks and down the hatch they went.

I was starting to feel pretty relaxed in this environment. The music was pretty loud and the lighting pretty dark, so whenever someone came up to meet me, my girl voice was well masked and passable. Red kept sending us drinks through the pledge waiters. With the maid outfit being so short, a few guys had copped a feel on my bare ass as they walked by. I had to keep up the illusion for Kathy so I just pretended not to notice.

Once she caught a guy doing it and saw that I did not respond. She asked if I liked having my ass touched by guys. It was weird, I told her, but being in this sexy lingerie it was kind of a turn on. She smiled at me and said we should head back to the bar and refill our drinks in person.

The bar was set up behind a wall and had an opening for the counter. People got in and out through a section of the wall that swung open. We got through the crowd to the front where Red and another barkeep, Shooter, were ready with drinks. Red kind of stumbled and told us that empty cups had been piling up behind the bar and that he wasn't usually this clumsy. Kathy suggested perhaps that we could come back there and start some of our cleaning. Red showed us how to get in through the door in the wall.

With Kathy leading the way, we made our way along the wall to the bar area. She saw the piling of cups and said we should start to move them. She bent down from the waist in front of me to pick up cups. Where I was, I had a nice view of her ass and the g-string that went down her crack. She then turned towards the boys and kept picking up cups as I saw them both grin. I was facing the other way and bent down to pick a few up and asked what she was doing. She said to follow her lead but to keep my ass facing away from the boys so they wouldn't see my secret.

Kathy and I proceeded to pick up cups around the two bartenders and as we got nearer to them, Kathy turned her bend into a squat, which I followed. The boys were watching their maids clean up and we were moving empty cups off to the sides so they wouldn't step on them. Kathy wanted a thorough cleaning and led us right under the counter in front of the two barkeeps, picking up cups along the way. She got in front of Shooter and I was in front of Red when she put her cup stack down and leaned it against the wall. She gave me a wink and said do what I do.

She turned her squat into a kneel and undid Shooter's fly. She then pulled out his limp cock and kissed it on the head. With the counter as high as it was, shooter didn't miss a beat serving beers. Kathy turned to me and gave me a nod. By this time I was pretty turned on by the whole night and pretty drunk thanks to Red. My admission earlier that I had liked my ass being touched gave me a brazen courage to follow Kathy's lead.

I unzipped Red's pants, pulled his underwear down, and freed his cock. I mimicked Kathy and first kissed the head a few times, then duplicated her by sticking the head in and out of my mouth. Red peaked down and said, "now that's my kind of cleaning."

As Kathy sucked on Shooter's cock which had grown to a nice eight inches, I did the same to with Red's. By this time, he had become a fully-erect seven inches and I was moving it in and out of my mouth with a good pace, occasionally stopping to lick up and down the shaft. I had a great buzz going and was surprisingly hard underneath my maid outfit. I was actually enjoying sucking Red's cock.

Red was enjoying it too as he was having trouble keeping all the beer into the cups he was pouring. Kathy and I now had wet knees while we sucked the cocks in front of us. We sucked for about five minutes when to our surprise, the next shift of bartenders arrived behind Red and Shooter. Shooter said that they had a few more minutes in them and then they could serve drinks and also be serviced by the cleaning staff that they had 'hired.'

I peered over to see Kathy licking Shooter's cock and smiling at me evilly. She then put his lovely eight inches back in her mouth and went at a pace I had not seen from her. I followed suit and looked up to see the boys start to rest their elbows on the counter above us, getting ready for the weakness in their knees they would be feeling from dumping a load of cum down our throats.

Suddenly, Shooter buckled a bit and I saw Kathy start to swallow. She was a champ and didn't spill a single drop. A second later, I felt Red's cock pulse and felt a warm torrent of liquid fill my mouth. With his cock already there, I had no choice but to swallow. I tried to keep up, but a little sneaked out and dripped down onto my chin. Red pulled his cock out of my mouth and Kathy used her fingers to wipe his seed off me and then stuck them right in my mouth. I had to keep up the act so I licked them clean. She then began to kiss me and I could taste some of Shooter's cum in her mouth.

While we were kissing, Red and Shooter zipped up and moved out of the way for the two replacement bartenders. The two fraternity brothers happily stepped forward. The brother that stepped in front of me was a nice looking black guy with a thin build. Kathy's guy was another lanky white guy.

She broke our kiss and gave me another one of her devilish smiles. "Having fun yet?" She asked.

"Loads," I said. Pun intended.

She went right for the zipper of the new guy and proceeded to pull out and suck his cock to it's six inches in length. I followed suit again and was shocked at the length of my guy. As I started sucking him, he must have grown to at least ten inches. Kathy glanced over and gave me a big thumbs up.

Being my second cock, I went to work on it. I was sucking him fast, trying to get him to cum so I could get out from behind this bar before the next shift arrived. I looked over and saw Kathy take her guy all the way in and his balls were resting on her chin for a second. She pulled back and let his cock out and told me to try. I figured what the heck and slid as much in as I could, managing about two thirds. I let his magnificent cock out of mouth and went in for another try and this time I felt a hand on the back of my head. My guy had reached down to give me some help and sure enough this time his balls had made it to my chin. He pulled his cock back and I took in some air and then every tenth thrust or so was him burying his cock in to the hilt. About ten minutes later, I felt him pulse and he dumped a huge load down my throat. I was much more prepared this time and swallowed it all down and then was prompted to lick his cock clean as he held it in front of my face until it was completely spent.

Once I was done, I peered over to see that Kathy was done with her lanky guy. I inclined my head to see if she could get me out of here, but she just pointed. I leaned out and around my black guys' cock and saw another set of barkeeps. I guess the rumor was out and the shift changes were coming more quickly now.

Our guys zipped up and were replaced by two new guys, one a short muscular white guy, and the other a short skinny white guy.

Kathy leaned over and whispered to me that she wanted to see these french maids get fucked. With the barkeeps blocking the view from anyone else waiting on deck, she said that no one would notice my secret, and with the counter above, the ones fucking us couldn't look down to see past our asses either.

She told me to get my guy ready and I unzipped him and started sucking him. I had the short skinny guy and he turned out to be about six inches, but I was still nervous. She reached into her french maid purse and pulled out some lube and two condoms. She reached down under my dress and inserted a lubed finger into my ass and moved it around until she could fit a second one. She worked that one in too until I was nice and loose.

Kathy handed me a condom and then started on her guy. She got him aroused then put a condom on him. She turned around so that her ass was facing him and then backed up into his cock. Her guy didn't need much convincing as he slipped into her wet pussy and started leaning in and out. To the people he was serving, it appeared he was dancing in rhythm to the music. From where I was, I saw my friend Kathy getting pounded nicely. She had her hands against the front wall and was using the leverage to balance herself and to thrust back.

I took the skinny guy's cock out of my mouth and put the condom on him. I turned around and moved my g-string to the side, careful to keep my legs together just in case he looked down. I held his cock to my opening and proceeded to back up slowly. My guy held his ground and I felt a sharp pain for a moment. After a minute, I relaxed and backed up further and continued this process until I felt his balls touching the hand I had put up to cover my 'pussy'.

Having found my hand, my guy backed out slowly, then eased himself back in and repeated this process. I used one hand to balance myself and one to cover my privates. I lightly heard Kathy over the music and looked over to see her getting nailed, then saw her looking back at my ass as the skinny guy with the six inch cock began picking up steam and really laying into me. I could feel his balls slamming into my hand with some force as he fucked my virgin hole. After what seemed like an eternity, my guy started to buck and I could feel him start to soften in my ass. I leaned down and his cock eased out my ass. I removed the condom and threw it into one of the empty cups. About this time Kathy's guy was really laying into her as the DJ had thrown on some club dance music. I saw her really panting and then noticed her guy starting to spasm. Kathy fell forward off his cock and leaned against the front wall, composing herself.

She looked at me and gave a nod to the door and I breathed a sigh of relief. She insisted we give the cocks that just fucked us a goodbye kiss, then zip them back into place before squatting our way out from behind the bar. We managed to squeeze past and were able to get out before the next shift arrived. Kathy led me out of the basement and back to her dorm where she dressed me in a silk baby doll and then we proceeded to lay together and describe the events of the night. She insisted on calling me a little cum whore and told me that I sucked cock very well. I was actually pleased by this and looked forward to next Halloween.

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