A Lost Bet Ch. 02


It was a fitful night. While the chair had been designed to provide at least a little comfort, having my arms bound behind me all night got to be uncomfortable. Plus, I was forced to remain in the same position because of being bound to the chair. And it didn't help that every so often, I had a machine pumping in and out of my ass. I slept intermittently, but when the light came on in the morning and I heard Frank come back in the playroom, I struggled to wake up.

"How ya doing sleepyhead? Did you have a good night's sleep?" He asked with a big grin on his face.

"mmpphh..." was all I could say as I remembered that I still had the gag in my mouth.

He chuckled as he walked over to the machine and shut it off. As he pulled the vibrator out of my ass, he gave it a little slap and said "looks like you got pretty well stretched back there. I wonder how long it will take before your hole reduces back to its normal size?" He smirked at that thought as he watched me squirm, feeling the cold air tickle my insides and trying to squeeze my sphincter muscle back into its smaller size.

"Hold still. I'm going to take off the gag first. Then I'll let you up." He lifted my head off the chair's headrest and unbuckled the gag from behind it.

"Owww. My mouth is so freaking sore." I complained. "Let me up Frank."

"Hold your horses Jo. I just want to get a couple of things clear. Okay? As soon as we do that, I promise I'll let you up and you can go. After all, the bet was only for one night." He paused for a second to let me gather myself. "Deal?"

"Okay Frank. I'll hear what you have to say but I can't make any guarantees about how I'm going to respond."

"Okay." And as he started talking, he loosened my legs and let them rest in front of me...and it felt SO GOOD to finally have them down.

"Look Jo. Last night was a trip. You kind of set yourself up for it. You have to know that. Granted, I know you thought you'd win the bet, but that's just the way the cards fall sometimes. Last night you got beat. I had to take you down an extra peg or two because you were talking so much trash..."

"But Frank, c'mon...making me dress like a girl? Fucking me? Both you and Tom ought to be put in jail for that. That was rape, dammit!" I yelled back at him.

"See, that's what I'm talking about. All that out of one mouth, and 2 ears that you just won't use. Will you shut up for a moment? If you don't, I'll just gag you again, then say what I want to say. Your choice."

I shut up.

"Jo, as far as Tom and I are concerned, we all had fun last night. Granted, I can see how you might not have thought so, but that's on you. I mean, you can try and report us if you want, but do you really want to go through the shame? I mean, first of all, you're a guy. You really want to be seen as being so weak that you got raped by another guy? Secondly, do you really want to share all the details with the cops...remember the enema, the outfits, the fucking machine...do you really want them knowing that you went through all that?"

"Frank, excuse me for interrupting, but I need to say this. What you and Tom did to me was wrong. Plain and simple. Now please, let me up. I want to go home."

"Okay. In a minute. As far as the reporting goes, do what you've gotta do. But let me say this too. You are always welcome in my home, and you're always welcome to come to the card games. Now pay close attention to this, because here's where your future really rests in your hands. We, okay, I did this to you once. I enjoyed it. I'm not gay, but I did like fucking you. Hell, so did Tom. After we left you last night, we agreed that this was not going to be the last time. Get that panicked look off your face. We're not going to come kidnap you out of your house...unless you want us to, that is. But know that whenever you come over here, you're going to have to earn your right to be a man. Anytime you're over here, there will be betting, and you're the prize. The bets will vary, the games will change. Sometimes, you might even get off scot-free. But for the most part, once you walk in that door, one of our goals, one of my goals, is to treat you like a woman. You can fight it, or you can give in. Personally, I'd prefer that you fight it. It's more fun that way. But last night, initially after you lost the bet, you responded with dignity...like a man. And that was cool. You just didn't know what to expect. I didn't either...until things start going the way that they did. Now that I know what's possible, I have no intentions to stop. So the question is...are you man enough to come back to this house knowing what's in store?"

I sat there looking at Frank like he was crazy. I mean, did he seriously think that after everything he and Tom put me through the night before, I'd willingly come back over and risk the same treatment?

"Let me up Frank. I'm going home."

"Okay, that's fine. You can think about what I've said." He undid the straps holding me to the chair, then released my arms from their bondage. I spent a few moments massaging the life back into them, totally forgetting that I was standing in a bustier, stockings, and heels. "Where are my clothes Frank?"

"They're upstairs in the bedroom. You can take the outfits with you if you want." Then he snickered a little bit. I started to feel a runny feeling down the insides of my legs. As I looked down, I saw the remains of the lubricant and machine ejaculate running down my legs.

"Jo, I hate to say this, but you may need a tampon, or probably a butt plug to not make a mess while you're heading home." Then he laughed. I didn't know whether to be embarrassed or pissed off. "Check the bathroom next to the guest bedroom. Feel free to use whatever you find in there." He continued to laugh as he left me there to clean up.

I tottered my way to the guest bathroom on cramped and unsteady legs feeling violated and raw. As I rummaged through the cabinets in the bathroom, I found some old tampons. "Will this humiliation never end?" I thought to myself as I sat on the toilet to try and insert it. Apparently, the answer was no, because the tampon fell right into the toilet. My ass was too stretched to keep it in. I gathered myself together as I dug around in the drawers until I found a butt plug that didn't look too intimidating. As I lubed it up and sat on the toilet, I continued to think about what had happened. The butt plug slid right in. It felt a little loose, but as I stood and clenched my cheeks together, the plug stayed in place. I figured that as soon as I had my underwear on, it would be more secure. "I still can't believe those guys raped me. Of course I'm not going to the cops because I don't want to explain all this. I don't care that it wasn't entirely my fault. I'm not doing it. But I'm damn sure not coming back here," I thought to myself.

I hustled into the bedroom to take off the lingerie and get the hell out of there. The bustier went first. As I unfastened it, I took a deep breath and felt the oxygen flooding my veins as the air filled my lungs. I felt relieved. Next came the heels. As I sat down, I was still keenly aware of the plug in my rear. "Just ignore it. You've gotta do what you've gotta do." I lifted my leg up to undo the ankle strap and saw a flash.

"For my scrapbook," laughed Frank. "You look sexy." Then he walked away down the hall.

"Sonovabitch," I grumbled, sliding off first one heel, then the other. I flexed my toes and calves and felt muscles I didn't know I had. Lastly, I started sliding off the stockings. Of course I noticed the silky feelings on my legs, but that was secondary to coolness of the air on my naked skin.

I couldn't help but notice the different texture of my clothes. Any person who has ever tried on women's clothes and then men's clothes would note the difference. But that didn't matter. I was going home to try and forget that the night had ever happened. After I finished getting dressed, I made sure to leave all the lingerie and outfits right there on the bed. I didn't want Frank getting any ideas and thinking that I might have enjoyed it.

As I headed for the front door, Frank called out to me from the living room "See you next time Jo."

"Not on your life Frank. It's been nice knowing you." And I walked out, head held high, but with a slight switch in my hips. "Damn butt plug," I thought to myself. As I (gingerly) sat in my car to drive home, I was still trying to come to grips with all that had happened. "Man, I just need to go home, take a shower, have a nap, then go to the movies or the coffee shop or something. I just need to feel clean and free."

I drove home and did exactly that. I stripped off everything as I walked through my door, not stopping until I got into my bathroom where I finally dropped both my shorts and the butt plug. The shower felt good as the water caressed my body. After I finished, I wrapped a towel around my waist and went to have a drink while I dried off and watched TV. I don't even remember what came on. I know I sat down on the couch, turned on the TV and set my beer on the coffee table, then I passed out. I was more exhausted than I thought, because when I woke up, it was the middle of the afternoon.

"That's it," I thought. "I guess I'll have to find some other guys to hang out with because there's no way I'm going back to Frank's place. I mean, since I know what he has in store for me, why would I?" And since there was no good reason to do so, I resolved not to.

That was three months ago.

--- --- --- ---

"I thought you weren't coming back?"

"Yeah well, don't get any ideas. I'm only here because it's Super Bowl Sunday and you've got HDTV with cable. I'm not making any bets, so you can keep all your kinky ideas to yourself."

"Okay. Cool. Tom's in the kitchen. Go grab a beer and make yourself comfortable." Frank said.

"Thanks, but I'll stick to soda. I still don't trust you guys."

"I'm offended," Frank said with a laugh. "Hey Tom, Jo thinks we're going to drug him and have our way with her...I mean, him. I laid out the rules last time, and none of us are going to break them. No rohypnol. No chloroform. No need to worry. Just don't get pulled into any bets Jo and you'll be fine."

And with that, the game was on.

I had to give credit to the guys. Throughout the majority of the first half, the word "bet" didn't even enter into the conversation. We laughed and joked and yelled at the screen like most football fans. Then, it happened. I let down my guard. We had just seen a Lay's potato chip commercial on TV, and Frank asked for me to pass the bowl with the chips and salsa in it. I was trying to be funny and that infamous phrase slipped out as I handed Frank the bowl: "Frank, I bet you can't eat just one?" I regretted the words as soon as they came out. Both Frank and Tom turned to look at me. "Never mind. Never mind." I backpeddled. "Forget I said anything."

"No way Jo. Too late for that. You KNOW I'm always down for a good bet." Frank looked at me with a sinister grin on his face. "What's the time frame?"

"C'mon guys, I was joking. I take it back. That wasn't a real bet."

"Sorry Jo," said Tom. "A bet's a bet. Name the time frame."

"Seriously, guys, no bet. I was trying to be funny. I didn't mean it."

"Well funny-man. Looks like the jokes on you. Name the time frame," Frank demanded.

"1 week," I responded figuring that would give us all an easy out.

"Make it 2 weeks," said Tom.

Frank chimed in, "let's make it interesting. How about I don't eat anymore desserts OR meat for the rest of the week? How's that sound?"

"Can't we just forget it? I really don't want to do this." I felt like I'd just walked in to a trap.

"Nope. I'm ready to earn another night of fun. Oh, you are SO going to owe me for this." Frank chortled.

Tom, acting as judge said "I think we've got ourselves a bet."

"But how are we going to know if Frank ate or not?"

"Tell you what Jo. You're on vacation next week aren't you?" Tom asked. I nodded "yes."

"Well, I've got a way to make it interesting and fun for all parties involved. I know that we all have enough vacation time to take a couple of weeks off, so let's take a trip. We can go crash at a cabin at the slopes starting at the end of this week. Frank will check in with us for the first couple of days this week. As a matter of fact, I'll eat breakfast with him to make sure he doesn't cheat. Jo, you can have lunch with him since you don't work too far from each other, then for dinner, we'll check in with Frank's girlfriend. I know she'll be cool with the idea...both of him not eating meat and of him going away for a few days."

"What do you mean by that?" Frank asked, looking surprised.

"Don't worry about it man. She just wants a couple of days to hang out with her girlfriends and come to miss you. She'll be waiting for you when you get back. Trust me." Tom assured him.

"Alright. I'm in," said Frank. "Jo, don't bother packing too much for this trip. Once I win this bet, I'll take you shopping at one of the outlets on the way to the slopes." Tom grinned at Frank's suggestion.

"That's actually a good idea. Jo, if Frank wins, then next week at the cabin, you have to do WHATEVER WE SAY. That's the deal." Tom said.

"You guys aren't going to let me out of this are you?" I asked and watched as they both shook their heads no. "I don't even know why the hell I came over here. It was a stupid risk to take."

"Don't give up hope Jo," Tom said. "Frank could still lose his nerve."

"Not likely," said Frank. And with that, I watched him get some bread and water and gloat throughout the rest of the game as he proceeded to work on claiming his prize. I left that evening disheartened, and wondering what I had gotten myself in to.

Over the course of the week, I ate with Frank at my appointed time and tried to entice him to eat meat and desserts as much as possible. I even tried to make another bet with him, but he only responded with "one bet at a time Jo...one bet at a time." Then he'd leer at me. Finally, the end of the week came.

"I made it. A whole week without meat or desserts. Heck, my girlfriend was so impressed that she encouraged us to keep doing whatever it is we're doing if it will help me stay in good shape. I guess that means more 'workouts' with you, right Jo?" Frank laughed as he congratulated himself for a job well done.

Tom reported, "Frank did well as far as I could see. How about with you Jo?"

Grudgingly, I admitted that "yeah, Frank made it. He didn't even look like he was tempted."

"So you know what that means. For the next week Jo, my wish is your command." Frank literally could not stop himself from grinning and I could see the possibilities running through his head. Even Tom looked like the cat that caught the canary.

"Tomorrow morning, 10 am. We leave for the ski trip," Tom said. "I'll drive. Jo, we'll meet at your place. Don't worry, I don't think you'll have much packing to do."

And with that, the night ended. The next morning, the guys pulled up to my place at 10 sharp. "Jo, the only thing you need to bring is your ski equipment and toiletries. Everything else, we'll get on the way...including your ski outfits. You know Tom, I think we'll enjoy having our own private ski bunny."

"Frank, I believe you're right. Do we need to stop and shop along the way?"

"Yeah. We'll stop at the outlet stores to pick up the day to day wear that our little Jo is going to need. But I've already got a special bag packed for 'HER'" Frank said.

"Then let's get this show on the road!"

I climbed into the backseat of the SUV and Tom pulled off. Already, I could tell I was in for it because there was a note for me on the seat...appropriately, from Tom and Frank. Here's what it said:

Dear Jo, thanks for being man enough to uphold the bet. This week is going to be fun. Trust us. Your first responsibility is to strip here in the car, put on the panties and camisole that are in the seat pocket, then put your regular clothes back on. We'll handle the rest when we stop to shop... Yours truly, Frank and Tom.

I looked up and saw them watching me through the rearview mirror. With a sigh, I did as instructed. It would have been much easier to do in the house as opposed to the truck, but I suppose they wouldn't have had as much fun watching me struggle, and they wouldn't have enjoyed the looks given by some of the truckers we drove next to during the change.

A couple of hours later, we pulled into the outlet stores. We bought some ladies thermals, ski pants and jacket, workout clothes, sweaters, and tennis shoes at the sporting good store. At a shoe store, the purchases included a pair of hi-heeled Timberland boots, a pair of knee high black boots with a 4" heel, a pair of slippers, and a pair of red pumps. Frank told me he'd already bought a few outfits from the adult store that he thought I'd enjoy, but he also wanted to get a few more "appropriate" clothes. Probably the most uncomfortable part of the shopping trip was when we went into the lingerie outlet store. Frank asked one of the salespeople to take me in the back to get my measurements and the lady was just too tickled to be involved in my humiliation. We picked up panties, camisoles, stockings, a couple of bustiers and a couple of corsets that could be worn without shirts. We also bought a red leather miniskirt and jacket, a light blue minidress, a mohair sweater dress that came to mid-thigh, a jersey dress (you know...the ones that look like basketball jerseys), a couple of shirts, and a pair of cream Capri pants.

"Okay Jo. Here's your next task. Take the Capri pants, the baby blue shirt which should match your cami, and the tennis shoes we just bought and find some place to change," Frank ordered.

"Wait, you mean I have to travel the rest of the trip in women's clothes? People will know I'm a guy. C'mon, at least let me change once we get to the cabin."

"Jo, you can either change here, or ride the rest of the way to the cabin in nothing but your underwear. Either way, your male clothes end the trip here. It's your choice."

Obviously, I chose to change. I found a men's restroom near one the parking lot and, after locking myself in one of the stalls, stripped off my boots, jeans and sweatshirt. Then I slid the shirt over my head. I noticed that it felt different in the way that it fit. It was tight across the body and shoulders and arms, and it didn't leave much to the imagination. Next, I slid on the pants. I was thankful that the guys hadn't forced me to wear a skirt. But as I slid the Capri's up my legs, I realized that since they fit so snug, I'd have to tuck my dick back between my legs. That was a little uncomfortable, but one the pants were pulled up, it held fairly well. Finally, the tennis shoes. No big deal there, but the color scheme did match the shirt and cami I was wearing. As I exited the restroom, I couldn't help but look in the mirror.

"I'm so in for it. I don't know how I managed to let myself get roped in to this. If I'd never started hanging out with these guys, I wouldn't be doing any of this." My thoughts raced through my head. And the question that still bothered me was why I was going along with these outrageous things. Surely there had been a point where I could have walked away, but what was it? I could barely think straight at the moment, but I figured I'd have the next few days to ponder the answer to that particular question.

"All ready to go Jo?" asked Tom.

My answer was only to hand over my male clothes, then climb into the back of the truck. I crossed my arms petulantly and tried to ignore the guys as we started on the last leg of our trip.

As we drove for the next couple of hours, we listened to music and I tried to read to keep myself from obsessing about my current situation. I guess I must have dozed off, because next thing I knew, we were pulling up at a solitary cabin that was more like a chalet. I wanted to be pissed, but I was impressed by the layout of the place.

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