An Embarrassing Game

by Dick Dunham

 

I had gotten in to the routine of joining in with my sister and three of her friends every Thursday night for some board games. We had tried Truth or Dare and Trivial Pursuit but were looking for something new and different. The apartment for our regular meeting was over a costume shop owned by one of the girls mothers. Some one came up with the idea that we could modify the Monopoly game to make it more interesting. We could change the cards you had to draw to be something that we had selected. It was only natural to select a forfeit of dressing in one of the costumes from her mothers shop for a day. This could be quite embarrassing for the loser. Each of the contestants was allowed to enter one forfeit. In a way it was kind of unfair since I was the only male but I went along with it to show that I was a good sport.

The four cards selected were #1.. Dress up as a hooker, Picture showed Short skirt, fish net stockings, tight top showing ample cleavage. Very high heels. Submitted by me. #2 was a school girl outfit with a short pleated skirt and a white blouse tied in front. Little girls lace anklets and Mary Jane shoes. My sisters entry. #3 was a complete Shirley Temple outfit and the wearer had to sing the Good ship Lollipop on command. Submitted by Jane. # 4 was wearing a diaper and plastic panties under you clothes for the next 24 hours. Submitted by Colleen and the final one was Dressing up as a Pre-teen and carrying a dolly for the next 24 hours. Pig tails required. Submitted by Sandra.

As you can see it was going to be a lot more embarrassing for me if I happened to lose but being a good Monopoly player I felt I had an advantage. Just to make sure that the losers complied we were scheduled to have lunch together at the Dairy Queen on Friday. In addition it was unlikely that all five of us would actually have to draw a card. So the lucky ones had the duty of inspecting the losers at their jobs or school to check on them. Just to ensure compliance each player had to submit their credit card at the start of the game. If any loser did not do their forfeit their card would be charged for one hundred dollars for a shopping spree by the winners.

We had been doing this for a couple of weeks and the worst I did was wearing a diaper under my clothes. One other time I was supposed to wear the school girls outfit but I claimed I was sick so I got out of it. This night I was not so lucky. I drew the Hooker out fit which delighted the girls immensely. The 24 hours began at Midnight tonight but just to make sure I did not weasel out the game was interrupted and the girls insisted I try out the out fit now. They went down stairs and got the hooker stuff and brought it up for me. In order for this to be convincing I was made to do the shaving and Nair routine for hair removal. I had to dress in front of the girls which brought out a lot of giggles about the size of my manhood. They also took some pictures which they said would be returned if I faithfully paid my forfeit

I was dressed to their satisfaction which included plucking my eyebrows to a thin arch. I complained about this but was reminded about how I got away with my Sick Routine before. Since they were done I asked if I could get dressed and go home now. My sister said "one more thing now, turn around and put you hands behind you" This was a surprise but I did it any way. I heard a click and felt something metallic on my wrist. "What is this?" I asked. Sis said, "Those are handcuffs. We just want to make sure you follow through. You are going to have to walk home in that outfit and get some one to release you . At least we will get to see that. By the way, those are those rigid handcuffs and the key holes are facing up. We are going to fasten the keys to your genitals with a zip tie so that you will have to have some one release you. That should be really embarrassing to ask some one to drop you panties to get the key but you asked for it. It’s only 3 blocks to your apartment and we will follow in the car to make sure you get to your apartment O.K. The keys to your apartment are in the purse attached to your arm. You will probably need help getting that too. Have fun."

They put a cape over my shoulders so the handcuffs would not show. I got several looks and a few propositions on the way home but the girls in the car honked and yelled and kept every thing from getting out of hand.

It was a long 3 blocks since I was having difficulties with the high heels. When I got to my apartment I now had to find some one to get my keys out of the purse and also to release me. That part was going to be very embarrassing. My only choice was to be my ex girlfriend, Ramona, lived across the hall. My sister new this and it was part of her plan to humiliate me.

I could see she was still up by the light under her door and the music. I had to knock again. She finally opened the door and started laughing. "Why are you dressed as a hooker? Is there something you want to tell me? "Please Ramona, help me here. I need to get in to my apartment but my hands are cuffed so I cant get into my purse.".. "Who did this to you and where are the keys," she asked. My sister and her friends, we were playing a game and this was my penalty. They are in my panties fastened to my privates with a zip tie, you will need something to cut it with to get at them." "This I have to see," and with that she lifted my skirt and pulled down my panties. "Oh, how precious. Those are really sexy panties. Now tell me again why I should help you after the way you dumped me. You did not even face me. You left a message on my answering machine."

"I am really sorry about that but I just could not face you." Richard replied, "Please help me, these cuffs hurt" "What is in it for me" she asked. "Anything you want, just get me out of this nightmare." Said Richard. "O.K. she said. You never did this when we were going together, but now I want some oral sex". "O.K. Get these cuffs off and I will do it.". "The cuffs stay on. I want to make sure you satisfy me, It may take more than once Now get down on your knees." And with that she dropped her panties and spread her legs and sat down on the edge of the bed.

It took about three orgasms before she was satisfied. She finally dropped his panties and cut the key loose and handed it to him. "You have to release me, the keyholes are facing up and even with the keys these rigid cuffs are impossible to open that way." Richard said. "That’s your problem. I think a little payback is in order. I’ll open the door but you can sleep in the cuffs and that outfit. You look so sexy in it. Come see me in the morning and if you treat me right maybe I will release you.."

She took Richard across the hall and opened the door for him and said have a nice night. He sat on the bed and then realized he had to pee. He tried to get the panties off but cuffed as he was it was impossible. He went back to Ramona’s and knocked on her door. "Now what?". She grumbled. "I have to go potty and I can’t get the panties down." "Go in the bathroom and I will be there in a minute, "He sat down on the seat but could not get his skirt up. Ramona came in and helped him and just stood there and watched. "Could I have a little privacy," Richard asked. "No way sweetie, this looks like a Kodak moment to me," and she pulled out the camera from behind her back and snapped a couple of pictures of him sitting there with his skirt up and the panties down around his knees. He finished and she re-arranged every thing and took him back to his apartment. He tried to get comfortable but he knew he probably could not sleep much. About 15 minutes later Ramona came in. He was just sitting on the bed. "I have had second thoughts about leaving you like that; you were pretty good to me earlier so I will take the cuffs off. Stand up" When he did she kissed him on the cheek and with her hand reached under his skirt and fondled his rising manhood. Besides, I may want to use this in the morning, so I want you to be comfortable. I know you have to wear this outfit tomorrow so take it off and hang it up so it won’t get it all wrinkled. I’ll come over in the morning and do your make up so you won’t look like a clown." She asked if he wanted her to help him undress and he thanked her and said he could manage. Richard had trouble going to sleep. He kept thinking about how nice it would be to have sex with Ramona in the morning. That would be the only bright thing about tomorrow. He was not looking forward to the rest of the day having to go to work and lunch with the girls in the hooker outfit. My turn will come and the next game it will be pay back time. I think I will change my card to something really humiliating. On second thought may be we need to change the rules so you can’t get your own card. This is what got me into trouble this time.

  

  

  

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