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. Kathy had pulled out her chair so that she was sitting back from the table. "Bend over my knee right now."
I was all caught up in the situation and just followed her every command without thinking. Then to my surprise, she started to spank me. First I was embarrassed to wear this maid's uniform in front of all of these women, and now I was even more embarrassed to be spanked by Kathy. "I told you that you would be punished if you embarrassed me or my guests, so now you are being spanked. I hope you are more careful as the evening goes on, or you will be punished some more."
After Kathy had spanked me, she pulled down the thin pink panties and examined my ass. "I see that the spanking turned your ass a little pink already. Let's take off your panties right now so they don't get in the way of any future punishments." Then she slid them down my legs and completely off my feet. "You may stand up now and continue to serve my guests." Now, since I had no panties on, I was completely exposed in the front and back. To make matters worse, I had an erection due to the spanking. My penis stuck straight out from the little dress I was forced to wear.
As I continued to serve Kathy's guests, they grabbed at my now exposed penis and patted my bare ass. This made me even more unsteady and I spilled more coffee and food on the table. "After we are finished eating, I will punish Clyde in front of everyone for all of his clumsiness." Kathy said.
I was real happy when I had served everyone dessert. At least I won't have to keep going between the women with my erect penis and bare ass, and have them keep fondling me. When they had finished the dessert, they went back into the living room and I cleared the table of the dishes.
"As soon as you clear the table of dishes, please come into the living room. You can wash the dishes later." Kathy yelled out to me. Soon, I was standing in front of Kathy with all of the women staring at me. "You were very clumsy when you were serving my guests. Now it is time for you to apologize to my guests and to ask each of my friends to spank you."
"But this wasn't part of the deal. I was only suppose to serve your guests and wash the dishes!" I pleaded.
"Your have just earned yourself a more severe punishment for complaining like that. But before you get punished, take off your bra, blouse, apron and skirt." I did as commanded because I didn't want to receive an even greater punishment. Now all I had on was the pantyhose, with the hole cut out so my penis, balls, and ass were completely exposed. I felt so humiliated standing before the women like this. "Now be quiet, go over to Sarah and ask her to spank you."
Sarah had a big smile on her face as I approached her. "I'm sorry for my clumsiness. Please spank me."
"I'd be delighted to spank you," Sarah said. "Now bend over my lap."
Before I bent over her lap, Sarah hiked up her skirt and spread her legs a little. Soon I felt my penis between her thighs and then she squeezed her thighs together. My erect penis was now tightly trapped between her legs and she pulled me closer to her body. As Sarah began to spank me, I couldn't move. After she had spanked me for a while, Kathy said, "You can stop spanking him for now. Let him stand up so that Robin can spank him."
Next, I went around to each of Kathy's friends and asked them to spank me. My ass was feeling pretty sore by the time all of them had spanked me.
"I'm not done with your punishment, quite yet, Clyde. Go over to the buffet in the dining room and bring out everything that is in the top drawer." Kathy said. When I opened the top drawer, I was surprised to see that it contained several paddles, a riding crop, and some short whips. "Bring those in here and hand one spanking implement to me and each of my friends."
I felt so vulnerable handing each of the women an implement to spank me with. "Now I want you to bend over the edge of the couch. Lean forward as far as you can so that your ass sticks out high in the air." Kathy said. I had given the riding crop to Kathy and now she was hitting my inner thighs with it. "Spread your legs wide apart so that we can punish your whole naked naughty bottom." Now I was aware of my penis and balls dangling between my legs. To make matters worst, Kathy took the riding crop and smacked my penis and balls a few times.
"Everyone, gather around Clyde so that we can spank him all at the same time." Kathy said to the other women. At first I felt many hands touching my tender red bottom, then my spanking started again. With all of them spanking me, it really stung my bottom. It hurt so much that I raised up and rubbed my bottom.
"You better bend over again and stay bent over," Kathy said. "Otherwise, your spanking will last even longer." So I slowly bent over again.
"I'll go around in front of Clyde and make sure he stays in position." Sarah said. Then I felt her hands holding my shoulders down so I couldn't move. My spanking started again, but this time I was held in place.
My ass now felt like it was totally on fire. "You can stop spanking Clyde. I think he has been punished enough." Kathy said. "Clyde, stay bent over while I find some lotion to rub on your ass." The other women were talking about how red my ass looked while Kathy was away. When she returned, the lotion felt nice and cool and I felt many hands spreading it on my naked ass. Somebody even put some lotion on my exposed penis and balls. Although I had just received a spanking, I had an erection again from the women spreading the lotion on me.
"Now stand up and wash the dishes in the kitchen." Kathy said. I was hoping that since I was spanked, I wouldn't have to wash the dishes. As I walked into the kitchen, I heard them talk about spanking me.
After I had the dishes all washed and put away, I went into the middle of the living room where the women were talking. I still felt embarrassed because all I had on was the pantyhose with the holes cut out for my penis and ass.
"What do you want, Clyde?" Kathy asked.
"I'm through washing the dishes and I put them away. Am I now free to go?" I asked.
"I don't think that you were aware of it, but pictures were taken of you while you served us in the maid's uniform and during your spankings." Kathy said. "Robin is also in charge of Human Relations where you work. Unless you want these pictures to spread around where you work, we expect you to serve us again next Saturday, at the same time."
"But!!!!!!!" I exclaimed.
"Unless you want another spanking right now, don't say a word and go upstairs and get dressed. We expect to see you next week." Kathy said.
I didn't want to be spanked again, so I went upstairs and got dressed. It felt so good to be wearing my own clothes. I quickly left Kathy's house and drove back to my house. I looked in a mirror and looked at my very red, well spanked ass. I don't want anyone else to see the pictures of me, so I guess I will be serving the women again, next week.