Losing the Bet

"They stink at free throws!"

That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a buddy's car. Mike had to prank call his boss (yes, we were smart enough to use a pay phone, which you can actually still find sometimes). Timmy had the worst one so far. He was so sure he was right about Kerry beating Bush in 2004 that he had to do a 5k running race wearing nothing but a Speedo, a cape, and his shoes. He did end up writing in marker on his chest "yes, I lost a bet" so that people would stop asking about it. He actually made the paper with his outfit, which is when he realized he should have worn a batman mask as well. Copies of the newspaper picture kept showing up in his office for years.

Normally, it is just the guys of the group that are dumb enough to put in for the bets. Sometimes though, one of the girls gets adventurous or drunk or confident enough to lay one down. Mike's wife, Katie, had to take over carpool service for Julie's week. Whenever a girl was crazy enough to bet with a guy there was always some type of sexual subtext. Or at least an attempt at it. Usually, they wouldn't agree to the bet and the few times they did they ended up winning and the guy had to do something stupid, like sing his undying love to her at a karaoke bar. But, as all stories here demonstrate, things often take strange and unexpected turns.

My wife, Sharon, went to Kentucky which, if you recall, had a spectacular basketball team in the 2009-2010 season and they were expected to breeze easily through the tournament and play Kansas in the final. Jason, however, went to West Virginia. During a night out, with plenty of drinking, Sharon was shooting her mouth off about how Kentucky was the winningest hoops program ever and all that stuff. All of us were getting sick of it but Jason was really having none of it. He kept saying how Huggins would coach WV over Kentucky even though WV had far less talent and clearly less history but she would get in his face about John Wall carrying everything. Finally, he had had enough and told her to put her money where her mouth is.

The room actually got pretty quiet at that point. Most of us were pretty lit and we all knew what a male-female bet would be like. Sharon didn't even hesitate about the bet. She said that Jason would have to clean our house when Kentucky won. I'm not sure why, but she thought the bet would be even. Actually, I don't believe she thought there was a chance she would lose the bet. So, she nodded when Jason said she would have to clean his apartment. But then he dropped the bomb everyone else was expecting. If Kentucky and Sharon lost, he said, she would have to clean his apartment while wearing a French Maid outfit he would pick out from the costume shop.

As a little back story, our group is mostly made up of players from our coed softball team, with a few spouses and other hangers on. Most of us are in our late 20s or early 30s, with a few older guys who lend stability to the softball team. About half of us are married. Sharon and I had both turned 30 in the last year and neither of us was happy that our youths were slipping away. Both of us were working harder than ever, and needing to blow off steam every once in a while. For years I had been trying to get Sharon to dress a little sexier but she had resisted most of my efforts. Until we turned 30 that is. I think she realized she might not ever be able to dress sexy if she didn't do it now. Either that or she realized that she enjoyed the attention she got from me and others when we went out and she wore a low-cut shirt, or short-shorts. Every once in a while she would agree to wear a tight shirt that allowed for her pert nipples to poke through.

For the past few months she had been flirting much more often than normal. I used to think that I would be jealous about a girlfriend or wife that flirted with other guys. But once it started to happen I had to admit that I was really turned on. She had been particularly flirtatious with Jason over the past few months. During a party at his house she had some bread crumbs on her shirt and managed to talk him into plucking them off. The tight shirt with no bra left little to the imagination that night and her nipples were showing off. Jason did his best to pluck off the crumbs and made little or no contact, but it was a great sight. At the time, I was extremely conflicted. On the one hand, I was hurt and jealous that my wife was encouraging another guy to touch her breasts. On the other hand, my cock would get hard every time I thought about the event. The more I thought about it the more I came to terms with how I felt and how I actually wanted things to go further. What would it be like if one of the guys saw her tits? What would be like if they saw her naked? What would it be like if things went further?

The more I thought about it the more I got worked up. Finally, I had no choice but to let her know how I felt. I was scared to think what she would say. I'm not sure if I was more scared that she would call me a pervert or that she would jump at the chance to mess around with other guys. At first, I just kind of joked around about how it would be funny if she lost her top when we went to the beach and some of the guys saw her tits. She kind of chuckled at that. But she got kind of thoughtful. And we had amazing sex that night.

Back to the bet -- Well, if you're a college hoops fan you already know that WV upset Kentucky in the tournament. Like any good fan, Sharon was beside herself. She puts so much into her support for the team that she sometimes gets depressed when they lose in a situation like that. With this loss though, she didn't have time to be depressed, because Jason was on her as soon as the buzzer sounded.

"Oooooohhhhhh! This is going to be so great! My apartment is a mess and it needs a really good cleaning."

"I, I, I. well shit." Sharon's face was scrunched up pretty seriously at this point. I couldn't tell if she was more peeved about the game, losing the bet, or having to clean someone else's place.

"Saturday for the final four would be a great time to clean the place. Let's all party at my apartment! Sharon is going to do the cleaning! And she'll be in a French maid outfit kids."

Sharon flushed in embarrassment, but, because I know her, I could tell she was a bit excited about the whole thing. She put her hand on my thigh under the table and gave me a squeeze. Lately, she would quickly move her hand away, but now she was leaving it there, slowing moving her fingers in slow circles. Kind of like we used to do back when we were dating.

"Look Jason. You've seen our house. I'm not very good at cleaning," she mumbled. "Don't expect miracles."

"Oh honey," Jason replied. "It is only a little about the cleaning," he said with a glint in his eye. Sharon's hand moved further up my thigh, getting dangerously close to intimate contact. Already, it wouldn't be appropriate for me to stand.

During the drive home that night Sharon kept wringing her hands. I could tell she was fretting about the bet, but actually afraid that if I talked to her about it she would come up with some reason not to follow through. Which would be a huge disappointment. Finally, after long enough, I asked her what she was thinking about.

"I'm pissed!" That's not really what I thought her response would be, and my first inclination was that she was mad at me for doing or not doing something, or saying or not saying something. "I can't believe my Cats lost. I feel like there is an empty spot in my heart. Several of those guys are seniors and will never get to play another game." To be honest, I had almost forgotten about the game, immersing myself in the bet. But I patted her leg and consoled her as best I could. I love college basketball, but my alma mater hasn't been in the Final Four since before I was born and have only made the tourney a few times since. It is just tough to get emotionally involved in a team like that. But when your team is always in contention, and expected to win, losing in an upset like that is heartbreaking.

"You don't think Jason will make me watch the Final Four do you? I don't think I can stomach watching another game so soon."

"Well, maybe you won't have to watch the game since you'll be busy cleaning." Good God, that was probably the worst thing to say. Not supportive, and a reminder of the bet. She hates cleaning. Before I even finished the sentence her head whipped around so fast her hair flew up.

I'm going to spare you the argument, but I think it is clear that nothing sexy happened the rest of that night.

As the week rolled on, a strong weather system started building. That's important, because almost all of us are in some sort of emergency management job. The big party for Final Four night steadily got smaller and smaller as everyone got called into some sort of duty. By Thursday, we were down to Jason, Sharon, myself, and Jason's roommate Pete. And then I got the call. I had to head to Charlotte, about three hours away for a day or so. With the games on Saturday, it wasn't clear if I would be released to come back. But the bet wasn't with me, it was between Jason and Sharon and neither of them had any relation to the emergency roles. I actually started getting nervous about the conversation Jason and I had when Sharon wasn't around. He asked how risqué he could get with the outfit Sharon would have to wear. After thinking about it a bit, I told him to get something as risqué as he could find.

Sharon and I had joked about costumes like this before, and I had pointed out things like this when we were looking for Halloween costumes. She never really jumped at the idea and the department store costumes were sexy, but not any more outlandish than you would see on a network TV show. Either way, when Sharon learned I might not be there for the game she was beside herself and we had to have a chat.

"I'm not sure I'm comfortable with this," she told me.

"I'm not sure about it either. But a bet is a bet. I'm going to try to get back for the game. Just be cool. Heck, you don't even have to be in the same room with the guys if you don't want to." I was as much talking myself into it as I was Sharon.

In the end, we agreed that she had to go through with paying off the bet. And I would do everything I could to get back for the game.

When Saturday rolled around I really was stuck in Charlotte, hoping for a reprieve from the weather and potential crisis. If I could get out by six I could make it for the start of the game, but it was clear I wouldn't be there for any pre-game activity. Sharon's agreement required her to arrive at 8 and put in an hour of cleaning before the late game.

Fortunately, the weather cooperated and I was released from duty at 6. With some luck, I could get back in time for tip-off. I wouldn't be there for the cleaning, but Sharon was supposed to wear the costume through the game and get people chips and beer when they needed. I also had another plan.

"I'm just getting out of here now. I should be there in time for the second half," I told her over the phone. I had actually gotten out an hour earlier and pulled over to the side of the road to call.

"Second half? Are you serious? I have to be there by myself for 2 hours before you get there? I don't know if I can do this."

"Look. We've been through this before. You have to do this. And we can trust Jason and Pete. We've known them for years. You'll be fine. It will be fun. And I'll be there soon. I can't wait to see you in that outfit anyway."

A pause on the other end of the line was long enough I looked at my phone to see if the call dropped. "You still there?" I asked.

"Yeah. But I think I have something to tell you." She may, at this point, have actually heard my eyebrows rising at this.

"Go ahead."

"Well, I don't know how to say this."

"Just say it Sharon. What's wrong?"

"It's just that, well. This whole thing. Um. I am really horny right now." Wow!

"I'll be there as quickly as I can. Might have to break a few speeding laws. But I'll get there. What are you going to do?"

Her voice got really low, and I think she was touching herself. "I'm going to go over there, change into the costume he bought me, and clean the apartment. I'm going to strut a little. When they want some food, I'll get it for them. When they want a drink, I'll get it for them. I've got some high heels, so my legs and ass are going to be on display. I'm going to bend over to get the beer out of the fridge and show off the bottoms of the outfit he got for me. When I bring the beer over, I'm going to bend over and show off my tits."

"Wow." It's a good thing I was smart enough to pull over earlier, as I don't think I could drive. "That is so hot. How fast should I drive?"

"Don't you really want to know what I'm going to do if they want more?" My heart started racing at about the same speed my mind was. I mean, I've always wanted her to wear sexy things and be more provocative, but this was even more than I had thought through.

"Ahem. Well. Ok. What if they want more?

"Mmm," she moaned, clearly pleasuring herself. "Maybe I'll let them." My cock jumped painfully in my pants, demonstrating what I had wondered about. Yes, this was turning me on more than I had been turned on since high school.

"I better get going. See you in a couple of hours. Be careful." I fired up the car and squealed out of the rest area, hitting speed in seconds. Was my plan good or bad? This is the type of thing that could change a marriage and a life.

To say I broke the law on speed would be to put it mildly. But even at speed there was no way I could get there even 45 minutes after Sharon was to start cleaning. The miles went by fast, but not fast enough. Even better, I never got pulled over, which could have been bad due to my job.

About 8:15, about a half our away, my phone buzzed. I don't generally like to talk while driving, especially at the speed I was going, but this seemed important.

"This is crazy," she said before I could even say hello. "Did you see the costume he got for me?"

"No, why? What's wrong? Does it not fit?"

"I'm in the bathroom and just changed into the outfit. It's a lot more, um, revealing than the ones we've looked at before."

"What do you mean; they're supposed to be sexy. And I thought you had gotten into this."

"No, this is much more. Well, much less than I thought. There's really not much there -- there, if you know what I mean."

"I'm going as fast as I can. What do you mean about not much being there? That's the point isn't it?"

"Well, the skirt is much shorter than I expected. The whole skirt is maybe 3 or 4 inches long. And it is sheer." Again, my cock jumped and I seriously got concerned about too much blood flowing from my brain so quickly that I would pass out.

"But you've got the skivvies that come with the costume. Those cover more than most bikini bottoms."

"Not on this outfit. It's just a g-string. And the front of that is sheer too." The nerves in her voice were no match for the emotions going through my head as I thought about her in a tiny sheer skirt with only a sheer g-string underneath. And that she would be spending time in front of my friends like that.

"Um. Ok." Really supportive, eh. But it was all I could manage to get out.

"And the top. It's um. It's pretty much just a black bikini. And it is sheer too." Oh God. I almost ran off the road.

"Are you going to be able to do this?" I asked. Hoping she would back out but also turned on that she would go forward.

"No. But I think I have to. Are you ok with this?" I think this was the first time she asked me if I was ok.

"I think so, but just be careful ok." Man, just the thought of her in that outfit was making me crazy. "Are you going to do all that bending over you mentioned earlier?"

"I don't know if I can do that. We'll see." The tension in her voice could be cut with a knife, but it seemed like she was also pretty excited too. "I think I've been in here long enough that the guys are getting worried. I should probably go out there."

"Ok. I love you. Be careful Sharon. I'll be there as soon as I can, probably just before the end of the first half."

"Love you," she replied and then the line went dead.

I screeched into Jason's apartment lot at about 8:45. My initial "plan" was to be able to surprise them a little early since they didn't think I would get there until 10. But as I arrived I thought of another plan. Jason's apartment is garden level and with it being dark out, I realized they wouldn't be able to see me if I took a look in the windows. Yeah, a bit illegal, and I might freak out the neighbors, but I wanted to see what was happening. Plus, it was warm enough to hang out outside.

I walked (ok, I snuck) around the side of the building. Fortunately, the back side had a courtyard with a bunch of trees, but I had to push through some bushes to get to the back of Jason's apartment. As I finally got through it was a relief to see that all of their lights were on, meaning it would be very difficult for them to see outside. Plus, several of the windows were open to let in the fresh air. What would I see? Heck, with the windows open, what would I hear? As I approached I could hear some type of machinery going and once I got to the window I could see Sharon vacuuming a bedroom. And she was right when we talked on the phone. The French Maid outfit was indeed a lot more revealing than the ones we had looked at before. With her high heels and the short skirt, half of her ass hung below the end of the skirt. And the g-string didn't hide much. At 5'7" and 125 pounds, she was still pretty damn tight. No cellulite. I had never watched her like this and I had to arrange my cock. When she bent over to pick up the power cord I just about shot a load right there. Her pussy lips were completely on display in the sheer outfit and it was clear that she was pretty excited. I couldn't believe there was nobody in the room with her, watching her work. But then she turned around and I thought I was busted until I noticed she was looking just to my right, in the corner just next to the window I was looking in. There was Jason, holding a beer and watching Sharon work.

With her turn in my (our) direction I finally got the full view. Her top was so completely sheer that every bit of her was visible, and clearly turned on. Her nipples were extended as much as I've ever seen them. She clicked off the vacuum and I heard her ask what was next on the list.

"It's five minutes to tipoff, let's go into the living room. You can start putting out."

"The food. Right?" she finished for him.

"yeah, put out the food. That's what I meant." They walked out of the room, Sharon in her very little clothing with her high heels, showing off just about everything.

As they left the room I slid over about 10 feet so I could look into the living room where Pete was watching the pre-game show. The living room had a small couch, a recliner, and a decent sized coffee table, covered with the normal crap guys in their 20's own. Some sports magazines, a trinket from a trip to Cancun, and a bunch of remote controls. Jason and Sharon entered the room as Pete was tipping up the last of his beer. "Oh Sharon! This one is empty. I need another."

Sharon sneered at Pete. He has never been one of her favorites. "So?"

"Aren't you the maid today? Get me another beer." Sharon stared at Pete with more than a bit of anger. Did I mention that she doesn't like to be ordered around? Then she looked over at Jason and he nodded, indicating that she should indeed be delivering fresh drinks. I could see the resolve set in her face, and then she walked over to Pete to get the empty. He had put it on the coffee table so she walked over to it, turned her back to him and bent over to pick up the can. From my angle I couldn't really see what he saw, but it is pretty clear that he got an amazing view of her ass and pussy from about 12 inches away.