A bet is a bet_(0)

Just to give you some background, my name is Jordan and I am your typical cocky jock, in my twenties. I had recently graduated college and when I was there I was on the club basketball team; my specialty was talking shit! It wasn’t just on the basketball court but in bars and at parties as well. I avoided a handful of fights that could have ended badly for me on occasion. After college, I moved out to Massachusetts having been originally from Seattle. I was a big Seahawks fan and loved betting on the games. This was just going to be another repeat win I could feel it!

I quickly made friends in the area through coworkers and what not. I was single and managed to get women pretty easily, I was 6 ft, 170, pretty cut and not too broad. I was invited to a friend’s super bowl party and was happy to go. There was about 25 people total at the party, my friend John was hosting it. John was recently married and a few people there were couples and singles. John ordered subs, had a ton of beers and wings. I was having a great time before the game even started. Obviously, there were quite a bit of Pats fans but there was about five people rooting for the Seahawks with me. I had about 6 beers before the game even kicked off.

Of course, I was shit talking about how the Seahawks were going to beat the Pats. Kim was there, she and I always got into it, she was a tiny little beauty, long blonde hair, tight body, big tits and a big attitude. Her boyfriend was Mike, a 6’4” black guy, always dressed in baggy jeans with a want to be thug attitude. She and I have gotten into heated arguments and he just stood there like a little bitch and didn’t say anything. I knew she wanted me and couldn’t understand why she was into this black dude.

The game was about to start when I asked Kim if she would cry when Tom Brady lost again before he retires? “You’re such a jerk Jordon, fuck off! Tom Brady isn’t retiring and they aren’t losing” I laughed; someone’s gonna be a sore loser I can tell already. She threw her wing at me, and I laughed again. I told her, wow Kim, you seem really confident your Pats are going to win, let’s make a little bet here. “Fuck off Jordan” Wow someone get upset and the game hasn’t even started, Kim its ok, I’ll wipe you tears away when you lose. “Fuck you Jordan you’re on.”

The liquor was running though my veins at this point, Fine I exclaimed, money or something else. “I’m not betting money,” Great I didn’t want you to, let’s make a bet, loser has to walk around naked the rest of the night after the game! “No whoever is losing at halftime has to be naked!” So, we will have to walk around naked the rest of the game, who here really wants to see me naked during the game come’on! Now you, I would love to see you naked for a full half! A few of the guys laughed and chuckled.

Jennifer, John’s wife, who couldn’t really stand me spoke up, “Hey Jordan if you are losing at the half, how about we dress you up like the little pansy you are for the rest of the game!” All the people started laughing as I turned red. “Well, since I am not going to be losing or even tied for that matter you’re on Kim, I’ve always wanted to see that fantastic little ass of yours!” Mike mad a face, but he wouldn’t say shit! What about the actual game I said? “We can decide at half time” Kim said.

At half time, you mean while you’re sitting there naked down by 14, no way we decide before kickoff. Kim said, “what are you thinking you little pansy!” The women laughed, especially Melissa and Erica, they were good friends of Kim and lesbians who seemed to have a thing against guys. I told her, “how about you don’t write a check you tush can’t cash, let’s bet that little ass of yours, I win I get to fuck you here in front of everyone!” I figured let’s push her as far as I can go now and see if we can settle somewhere in the middle, why not? By this point no one was watching the pregame show, everyone was fixated on me and Kim and the bet. “Well since you ass is going to be in a pretty slutty little dress already, deal, but if you lose, I get to fuck you!” Deal! I exclaimed, wait how the hell is she going to fuck me? “Wo wo wo wo, how do you plan on fucking me?” I said. Erica jumped up, don’t worry Jordan we can make sure we equip her for that, we’ve got some stuff in the car for that, as a matter of fact, I can’t wait to see your Alpha male self with a cute little skirt on, legs hiked up in the air, getting rammed in your virgin ass from Kim here in the middle of the floor.” Well since I’m not going to lose who cares I said with a grin.
Melissa spoke up, “who said his ass was a virgin, he seems like your typical closet guy, macho alpha male as a front but loves getting drilled in his ass.” A few of the girls laughed. You know what Kim, since you and all your little friends find this idea so funny, I am sure some of these other guys here who are all single would love to drain their balls in your tight little cunt; I’m guessing Mike hasn’t stretched you out, tough guy attitude but a small dick between those legs. With that the girls faces turned to disgust at my words, Mike jumped up from his seat.

“Who the fuck do you think you are man! How dare you talk to my woman and me like that. “It speak I said, you know what I said is true, all show of tough guy attitude with nothing to back it. I bet my dick is bigger than yours. Kim spoke up, “Jordan, I know Mike’s dick is much bigger than yours, how about this, if I lose, you and all your little single buddies can fuck me if your tiny little dick is somehow bigger than Mike’s dick. Now if your dick is not bigger than Mike’s, which well find out at half time, while your naked, than you get to take every inch of his small dick up your ass and take his load deep in your bowels, and how about the same thing on your end, all your little friend including any girls that want to equip themselves get to stretch you out wide and breed your ass pussy. Why do I say it that way, because after tonight you will have come here a man, and leave here a woman full of cum. Now if I lose, have at it boys, double team me do what you want, but your counting on the Pats losing and Jordan having a package to back it up.” Everyone sat in shock, I reached my hand out, “You’re on!” and we shook.

“Fuck this game I can’t wait for this brutal fucking tonight, Melissa were gonna spit roast Jordan!” Erica exclaimed, “gotta run out a get a few things though first” said Erica as she headed out. Some of the guys were high fiving me and what not, “damn this is great I haven’t gotten laid in months” I started to sweat a little while high fiving some of the guys, what did I just get myself into, what if I lose? I looked over at Kim and she had this evil dead stare at me, I glanced over at Mike and he had the same hate filled stare.

There it was opening kickoff, the game was underway, given the bet I put myself in I started to kick back a few beers. I could hear around me people snickering the whole time. Melissa came up to me and plopped a seat next to me, “So Jordan, your cocky son of a bitch, can I ask you a question, maybe a side bet or so.” “Sure, what’s up.” “Jordan, if you lose, and just get fucked by Kim, your gonna rip that ass open in pain, however, if at halftime your Seahawks are losing or even tied, me and Erica get the privilege of dressing you up like a woman, with Jennifer of course since it’s her house, in addition to that, we get to give you an enema and use three different toys on you. If the seahawks are winning, or tied, you get a private showing of me and Erica taking our double headed dildo in our asses and scissor ourselves. How does that sound?” “Wo wo wo what’s an enema and what toys?” “I thought you might asked that, well and enema is when we will your ass with water, and some lube and you shoot it all out, along with anything else that’s in there. When it comes to the toys, we have a butt plug trainer set that Erica is going to grab, three plugs with jewels on the bottom, one bigger than the other, the key is once we get the large plug in, if your losing you have to wear it the rest of the half.” “Fuck it I’m in, private showing of dykes butt fucking each other, I’m game, plus if you lose the game you got to scissor in front of the crowd.” “Jordan, sounds like a plan! Oh and by the way, Erica isn’t only grabbing some stuff for you, she’s getting some guys that might be interested in this to come too, you know the guys you call Fag when were all out?” “Oh, you mean like Marshall.” “Jordan your right on the money how did you know.

As I laughed the first quarter ended, John made his way to the front the score was 0-0, “ok guys and gals, I know a side bet between Kim and Jordan has seemed to take center of attention over this, since this is my house I wanted to let you know after the game is over make you way downstairs. To accommodate I have set up a make shift table where the festivities will take place to whomever the winner or loser may be. Now Jordan and Kim, you two got yourselves into this, I want you both to shake that no matter who wins, the loser and winner will uphold their end of the bet like a sportsman, Mike that includes you too, no fighting, crying or wimping out. Now Kim and Jordan please shake and honor your bets,” and we did, she looked at me like she could kill me with those eyes.

Erica came in not to long after with a few large bags and quickly ran up with Jennifer to her room. I also saw a bunch of people come in after her, mostly the gay guys she hung out with who all were looking around as they came in. Now there must have been around 35 people there. First the pats scored, Kim jumped up and started cheering in my face then the Seahawks answered right back and I did the same, the clock ran out in the second quarter just as the score read, 14-14, now I was sweating before as the Seahawks were down and score with two seconds left. I looked at Kim blush red as did she right back at me, both of us sweating. The crowd cheered! “Take it off, take it off” they shouted. I saw Kim with a defeated look, pull her shirt over her head, the guys went wild, just as I was waiting I looked to Erica and Melissa, Erica obviously didn’t know about the side bet as she ran up and grabbed my hand. The girls Jenn, Erica and a hesitant Melissa ran up the stairs with me.

“Erica I kinda made a side bet, it’s a lose win, kinda of.” She told Erica what she did, and Erica said a bets a bet, Jenn, start shaving him well get ready on your bed. Shave me? “Silly, you can’t dress like a woman with all that hair,” next thing I knew I was naked in the shower, being shaved down, after I was done, Jenn took me out and applied a generous amount of make up to my face, “Com’on this is enough,” “Its enough when I say it is, a bets a bet.” Just as she said that a naked Melissa and Erica come in the bathroom, “Enema and butt plug time,” they say me down on the seat, applied a generous amount of cold lube and slowly worked it around my hole.