You had made a bet with your sister after she had asked you if you would lend her an outfit for her meeting. You laughed at her. “You can never wear one of my outfits! If you pull that off, I’ll wear one of yours to one of my meetings!” You laughed, but she did not. “Ok. Deal!” She …
Read MoreThe bet was over Novak’s smart-ass remarks over how easy his girlfriend had it as a nanny. Beth challenged him to spend one day in her shoes. If he could keep up, then she would watch football with him all season. If he couldn’t, he had to substitute for her when she went back to visit her parents. Novak is …
Read MoreWhen Janice held up the skimpy white lingerie, Greg felt his heart sink. “I’m not wearing those!” he protested. “Oh yes you are,” Janice said enjoying her husband’s embarrassment at what she was proposing. “You agreed to play this game and you lost the draw. As agreed, that means you have to do whatever I ask and I’m asking you …
Read MoreDo I really have to wear this underwear too? It’s bad enough I’m going as a cheerleader, but- Of course, you have to wear proper underwear. You’d look pretty stupid wearing boxers under a cheerleading skirt. But everybody would know it’s just a joke. Like this, everyone will think I’m just…a…a girl. Is that my fault? I …
Read More“Come on baby, smile.” I just couldn’t bring myself to do it. For hours now, my sister has been dressing me up in these cute little outfits. And every pair of shoes she puts on my feet just seem to get taller and taller. I’m so tired and all I want to do is sit down for a few minutes …
Read MoreWhat started as a simple bet quickly spun out of control. Jim’s secretary had bet him he couldn’t last a week in heels. With a day left, he was caught taking them off. Now he had to dress as a secretary for the week. But on the third day, he came in with slacks instead of a skirt.. As he …
Read MoreWTF! I lost a bet with my girlfriend and I accepted piercing my ears as a pay. But as soon I entered to the salon, I became so nervous. My girlfriend talked with the beautician and she decided to give me a sedative. I have just wake up now and you can imagine my reaction when I have seen looking …
Read MoreLonny turned to look at his sister Gena and said as he put his hand on his hip “Just because you put me in this long-haired wig and a dress don’t think for a minute that somebody will mistake me for a girl” Gena almost laughed right in his face as she looked at her macho younger brother. She didn’t want to …
Read MoreAndrew’s girlfriend had dressed him up for firm’s Halloween party. The office girls had a ball teasing the new ‘girl’ and goaded him into a bet. For every girl that guessed correctly the colour of his panties…he would have to work for a week in drag. Andrew lost big time…16 office girls got it right. Damn it!! Now I …
Read MoreChris had been in college for a year and was used to getting drunk at parties. One night however, he got more drunk than usual- causing him to make a risky bet with some girls. After losing the bet the girls called him over the next day. His hangover made it difficult for him to wrap his head around it- …
Read MoreIt started out as a normal evening. You and your friend Brian were watching the Superbowl, as you did every year. You had bet on the Seahawks. Every year you and Brian placed bets on the game, and the winner got to choose the losers punishment. This year, you lost. You knew it was going to be bad as soon …
Read More“Francine… I know I have to clean your condo but really, is this outfit totally necessary?” “No, I’m not trying to go back on our deal. I remember the uniform being at the discretion of the home owner was my idea. I do remember saying that if I had won the bet I would have had you cleaning my …
Read More
