I work in a large company and every year we have a large fundraising event. If you don't have the money to contribute, you can also donate any goods or services. All of the funds go to local charities, so it helps everyone. The event is held at a large hotel, and there is a large silent auction of donated items. There is also plenty of food and drink, although it is a cash bar and the profits go to the different charities.
At the time, I was just making ends meet with my bills, so I donated something that I could do for somebody. I wrote out the description this way: "A cheerful male willing to help fix the food and serve your guests during a dinner party. If needed, willing to help with the dishes. This would take place on a Saturday or Sunday and would include 4 to 8 hours of my time."
I thought another man would buy this for his wife. That way, if they wanted to entertain guests, this would take much of the work off of his wife.
At the end of the fundraising event, all of the service donations were auctioned off. The person who donated the service stood on stage as the Master of Ceremonies read the service, and then the auction took place. Mine was near the end, and to my surprise, and my service went for a thousand dollars. That was a lot more than expected. Before I left the hotel, a woman approached me
"Hi. Is your name Clyde and are you the man who donated 4 to 8 hours to help serve a dinner?" She asked.
"Yes I am. Are you the one who donated the thousand dollars?"
"Yes. My name is Kathy and I was wondering if you could serve my guests at a dinner party this Saturday?"
I checked my calendar and said, "Okay. I would be able to do it on Saturday. Just give me the address and when you want me there."
Kathy proceeded to give me her address, phone number, and told me I should be there at 4 PM. I was surprised that all of this was happening so fast. Then she also asked me for my measurements; height, weight, pants length, waist size, and shoe size. She said I would find out on Saturday why these measurements were needed. Kathy was also a woman about my age. She was nice looking, and I was looking forward to help serve her dinner guests.
When Saturday finally happened, I took a long shower, and put on a sharp looking suit. If Kathy had paid a thousand dollars for my service, I wanted to look real good for her. She lived out in the suburbs, in a big house. I arrived right at 4 PM, and she greeted me at the door.
"I'm glad to see that you are right on time. Come on in."
Her house really looked nice. There was plenty of wide-open space, and she gave me a quick tour of her house. Then she said, "Follow me. I want you dressed the proper way to serve my guests." Kathy led me upstairs to a bedroom. To my surprise, there was a maid's outfit on the bed, complete with an apron, ruffled pink panties, pantyhose, skirt, padded bra, blouse, and shoes.
"You don't expect me to wear that!" I protested.
"Yes I do," Kathy said. "When you donated your service, you signed a form saying that you would perform the service to the satisfaction of the person who bought it. I need to sign another form stating that you performed your donated service. If I don't sign the form, you will need to donate the thousand dollars."
"Show me where it says that!" I said.
Sure enough, the form I signed said this. I was shocked. I didn't have the thousand dollars to donate, but I didn't want to serve the guests in this maid's uniform either. But I gave in and said, "I wasn't expecting this, but I guess I will serve your guests in this." Now I could see why she took down my measurements at the auction.
"Good. Get dressed and then meet me in the kitchen." Kathy said.
The black pantyhose had a big seam down the middle of them, and the panty part was cut out so that my penis and balls poked through in the front, and most of my ass was bare in the back. The panties were pink, thin, and almost transparent. The skirt wasn't very long and it didn't cover up much. I felt very embarrassed to put on the padded bra and the blouse, which buttoned differently than what I was used to. Everything fit me a bit snug, but it did make me look more like a female maid. But I knew that anyone looking at me could see my male anatomy. The last thing I put on was the shoes. They were high heel shoes that weren't very high, but I had to get used to walking in them. I was quite unstable as I came down the stairs to the kitchen.
When I walked into the kitchen, Kathy was fixing something over the stove. "Come over here so that I can inspect you." Then she started making little adjustments to this maid's outfit. The seams of my pantyhose must not of been straight because she said, "When will you men ever learn how to put on stockings. You never get the seams straight." She lifted up the front of the skirt and said, "You better keep this down, or you will pay the consequences for it." I even had to bend down so that she could examine my ass.
"In this house, a maid is not to speak unless spoken to or asked to say something. If you do anything to disturb my guests or embarrass me in any way, you will be punished for it. So why don't you keep stirring this for me and my guests should start arriving in a half hour." I stirred a lot of food, put food in special bowls, and helped Kathy in he kitchen. I still wasn't used to walking with high heels, so I was real unsteady when I walked.
Soon the doorbell rang. "Clyde, I want you to greet each guest. So answer the door for me."
"But I'm dressed like a maid. You have got to be kidding."
"I'm not kidding! So hurry up and answer the door."
So I wobbled over to the door, and when I opened it, there was a woman about my age waiting impatiently outside. She stared at me up and down and said, "Well look at you. Aren't you something to behold? Kathy said this was going to be a different type of evening, and I guess she wasn't kidding. I'm sorry. My name is Sarah. What's your name?"
"I'm Clyde. Please come on in."
"Maybe we should call you Claudia in that outfit." Sarah said as she walked past me into the living room.
I helped Kathy in the kitchen, again, and the doorbell rang five more times. Each time it was a woman and all of them said something about the outfit I had on. Soon, Kathy walked into the living room and greeted the ladies. She told them that this would be a special evening because she had this "special" maid who was going to serve them. Then she had them gather around the large dining room table. Now it was my job to bring out the food and to serve each woman.
Since I was so wobbly in the high heel shoes, I almost spilled some coffee on one of the ladies. "If you do that again, you will be punished on the spot', Kathy said. I was trying to be careful but one of the ladies reached under my skirt and grabbed my penis and balls. Sure enough, I missed her coffee cup and spilled coffee on the nice white tablecloth.
"Come over here this instant." Kathy demanded. "I won't tolerate your clumsiness." I walked over to her and stood beside her.