Bet

Embarrassing bet

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My friend kerra and I always enjoy making bets, between one another. So we both went to the highschool football game together. In the beginning of the game I made a bet, that if my team won then she would have to wear and do what I tell her for a day. And vise versa. Anyway my team lost, and she had me wear a maid uniform. Then she drove me to her house wearing that uniform. Her friends were there laughing at me, and I was completely embarrassed. I cleaned her house, completley, then she told me to put on a diaper. I did as I am a man of my word, they had baby stuff like, pacifiers, bottles, and bibs. They took lots of photos, and my face started to turn red with embarrasment.

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Servant

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I was 12 years old and with my friend we lost a bet (she was also 12).

We were both tomboys, for this often hang out with the boys, going to play soccer or wargames.

Often boys, since we were girls, we challenged each other to do things, how to win at soccer 2 vs 4,  obviously we lost the game and had to undergo a penance.

The boys had recently watched a show on TV concerning ancient Rome, in a party where some nobles were served by scantily dressed slave girls.

So here’s the penance, the Saturday after the boys have organized a party in the garden of one of them, with them and some friends of our age.
The parents were not present, as they were out for the weekend.
We would have had to serve as a waiter for the party, but wearing only a scrap of cloth around the hips.

Me and my friends accepted the challenge couse we where stubborn and crazy.

But it was one of the most embarassing event in my life. There were a dozen of our classmates, all boys, and we were practically naked. I think I had the red face all the time. The rag of cloth was in danger of loosing and falling all the time. already it did not cover much, the knot with which I had tied occasionally undid, and often I had my hands busy from the trays, and I could not fix it. The garden, then, had the bushes all around, but from the street you could see inside.

Wearing only a rag of cloth meant not only no panties underneath, not only that our torso was under the eyes of all, but also any kind of footwear, and even if the garden had a little ‘lawn, most was made of gravel, really sharp gravel, and cement, scorching cement. Not only do we suffered the embarrassment of being practically naked in front of our classmates, but also the torture of burnt feet onto concrete and sting them on the sharp gravel.

The party started at 2.00 PM and ended at 11.00 PM, when we were allowed to dress, our clothes were kept locked away for the entire time of the party, so we can’t flee the chalenge.

It was one of the most embarassing moment of my life, but not the last one.

1

My bet with my sister

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This just happened a few weeks ago. I’m a 17-year-old guy, and my sister is 15. One interest we both share is sports. Only my sister also likes to gamble on sports. She generally breaks even. Occasionally, she loses big, but pays for it with a lot of small wins. I’ve always worried about her, but she ignores my warnings. Our parents think it is just a phase.

So earlier this month, on Sunday, Jamie and I were planning to watch the Rangers-Angels game on TV. But Mom wanted us to run a few errands for her. No problem. We would just record the game on TV and watch it later. That meant keeping the radio in the car turned off so we don’t accidentally hear the score. So we made a few stops and then went to the mall for the final errand. Jamie wanted to then go look for a new top to wear to a friend’s party. I didn’t want to spend time watching Jamie shop, so I went elsewhere and told her to call me on my cell when she was ready to leave.

So I pass by an electronics score and the radio is on. I accidently hear part of the game. It is the top of the ninth, Texas already has a big lead and they are putting together yet another rally. Well, I guess the game is spoiled for me, but I get an idea on how to teach Jamie a lesson.   As we are driving home, I say to her that I would like to make a bet on the game. Jamie is surprised because I never gamble, but I am betting against her Angels, and she cannot pass up any bet. She asks how much, and I say no money. If Texas wins, she has to get naked in front of my friends, but if the Angels win I get naked in front of her friends. She immediately agrees.

So we start watching the recorded game. Texas takes an early lead, and by the middle innings it is clear how the game will turn out. From the middle innings on, Jamie says nothing. She just stares at the screen. When the final out is made, she takes the remote and turns off the set. Jamie turns to me and asks, “So, when do I put on the show?”

Now I have no intention of having my sister go naked in front of my friends. But I am trying to teach her a lesson, so I am going to make her squirm for a while. I note that next Sunday our parents will be gone for the entire day. I will invite my friends over to see the Clippers-Thunder playoff game. Jamie can do her little strip tease then.

All week Jamie is obviously thinking about Sunday. Sunday comes and she is helping me get a few snacks ready for the guys. She asks, “Do I do it before or after the game?” I decide she has enough, so I tell her to forget it. The bet is off. I thought Jamie would be relieved, but no. “I don’t welsh on a bet,” she says. I tell her it’s OK. It’s not welshing if I let her off the hook. She says she always pays her bets regardless. I finally confess the bet was rigged, but it makes no difference. “I took the bet willingly. I lost. I don’t welsh on my bets for any reason.” I do not like the way this is going.

By the time my friends arrive, I am pleading with Jamie not to undress. With everyone sitting waiting for the game, Jamie stands up and tells the guys about our bet, and that she is now delivering the payoff. My friends whoop and holler as Jamie begins to undress. When she gets down to her bra and panties, they call for more. So off comes the bra. The guys cheer. Down come the panties. More cheering. Someone asks her to turn around so they can see her ass. Jamie does what is requested. Finally she says the show is over and gets dressed. I am dying.

After the game, everyone leaves and I ask Jamie why she stripped when she didn’t have to. “You wanted to teach me a lesson?,” she says. “Well, I wanted to teach you a lesson. It was humiliating and embarrassing to go naked in front of your friends. But now it’s over. My embarrassment is done. Your friends will never mention this to me again. But they will mention it to you. They will tease you for months on end, and you will continue to be embarrassed.”

Jamie was right. From the next day on, whenever my friends see Jamie, they are also polite and nice to her. They say hi, or ask how she’s doing. It is just like before. No one mentions seeing her nude. But when it is just me, the guys bring it up constantly. It is now only going on three weeks about, so it hasn’t been months yet as Jamie predicted. But I am getting pretty sick of the ragging.

 

BTW, Jamie is still gambling. She lost a lot betting on the first two games of the Thunder-Spurs series. She hopes to make it up on the Magic-Pacers series. And I still worry.

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little brother bet

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Me(15) and my younger brother(13) has always have a strong rivalry but i allways win every thing. So dicied to have a race who ever could run around the block twice first wins and the loser had to do anything the winner told him today all weekend. i lost (over cofident). so a week goes by and my parents are going out of the town for the weekend for the aniversary and my brother ask if some of his friends could spend the weekend they said if it was ok with me, i of coarse said yes i didnt have much choice. so any way my brothers four friends come over and after a couple hours my brother says i have to walk around in underwear he found in my room. they are boxer briefs but were tight so you could see the outline of my dick they thought it was funny and he said we should order a pizza and i have to pay the way i was. so after awhile the pizza comes and i get a random boner so the tip of my dick is sticking out so the pizza dilvery guy saw it. my brother found paint in his room and they wanted to paint my bare skin i let them and they painted me every color of the rainbow and when i go to take a shower by brother said they get to watch so i am taking a shower in front of 13 year old boys and he said every time i got a boner i had to jack off with them watching so then they decide to watch porn on the computer so i get an instant erection and my brother sayed i had to jack him of what was kinda gross. so that was by far the most humaliting time of my life. he made sure none of them took pictures or anything so at lest he was still looking out for me ona grand scale

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My Brother and I — A Naked Wager

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Hi to all! I’m a 16 year old girl. This adventure involves me and my 13 year old brother. We are not the ones who were embarrassed, but it is still a good story. Especially for my brother!

First let me tell you when I was 6 and he was 3, every night at bath time I would take him with me to the tub. Mom prepared the bath while I undressed and helped my brother Aaron to undress. We then got into the tub together. I would wash Aaron and then myself. It was fun for a while, until we decided we were old enough to bath by ourselves. Still we got used to the idea of being naked in front of each other. This was as normal to us as being fully clothed. Even in our teen years, we thought nothing of it. Although outside the family, Aaron was shy in front of other girls and I was just as shy in front of other guys.

Now for the story. Not too long ago, I was having three of my best friends (all girls) over for a sleepover. We know that other kids are not as open with nudity as Aaron and I are.  Aaron said if my friends saw me naked in front of him, they would totally freak. I said my friends were more mature than that, so Aaron challenged me to a bet with the loser treating the winner to a movie of the winner’s choice.

We set the whole thing up beforehand. My friends arrived. I told them to go up to my room to change into their jammies and nighties. I would be up soon as soon as I got the food ready. So after 10 minutes I went upstairs to my friends. I began getting undressed. Meanwhile, outside my room Aaron was waiting listening for our special code word. When I was in nothing more than my bra and panties, I said the word. Aaron knocked on the door and asked if he could come in. I said yes. My friends started shrieking, “Susie! You’re in your underwear!” Yeah, I know that. So what? Aaron entered under the guise of lending me some CD’s I asked to borrow. He started talking about one which was new and I haven’t heard yet. My friends were yelling at Aaron to get out because I was half naked. (They were in their pj’s and bathrobes.) But Aaron and I weren’t finished yet.

As Aaron talked, I undid my bra. The girls really lost it then. “He’s looking at your boobs!” Right. But he has seen them before. I then slipped off my panties, and my friends were in hysterics. As soon as I got my pajamas on, Aaron left. He had won the bet easy. I ended up taking him to an action flick which I hated, but he totally loved.

But I demanded a rematch. This time Aaron would invite his guy friends over. My bet was that they would freak just as bad as my friends did, or worse. We used the same scenario. When I heard the code word, I knocked on Aaron’s door. He told me to come in. He was in nothing but his briefs. I started talking about the CD’s he asked to borrow. Only one boy commented saying, “Cool. Put on a show for your sister.” Aaron slipped off his briefs, there was a comment or two, but no one really freaked or shouted. Aaron slipped on his pajama bottoms, and I left. They guys make a joke or two, but that was it. No yelling, freaking, just a remark or two.

I lost another bet. I had to treat Aaron to another crappy action movie. I have to find something to bet on where I can win. He’s two up on me!

5

puking

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I was in the lunch line feeling pretty ill and a teacher came up to me asking if i was ok and padded my back and i ended up puking on her infront of everybody and kept puking all the way to the nurses More

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He’s Gay, I’m Not

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My friend Andy and I were in my room messing around after one of our baseball games.  At the time we were both 13 and decided to have a summer sleepover.  I was getting ready to take a shower and then More

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Horrible Bet

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I’m 14 and I have a 11 year old sister. Our parents were gone for the weekend so we had the house to ourselves. Anyway, we were outside and my sister claimed she was faster than me. I I quickly denied More

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Embarrassing freshman wedgie girl

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I was walking home from school one day during Homecoming week, which is in early November at my school. Since I was wearing a 9th grade class shirt, all knew what grade I was in. It was a few days after More

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Biggest mistake of my LIFE!

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I’m female and 13. So I made this bet with my little brother and who ever won got to make the person do something they wanted them to do. I thought I would win but I lost.I forgot about it and when he More

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