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  • A Lost Bet Ch. 01

A Lost Bet Ch. 01

12

I was afraid. I knew I'd lost a bet with some guys I didn't really know and I had no idea what they had planned. It was stupid of me to have made the bet, but I just knew I'd win. We'd been sitting around playing poker and I was almost out of chips. I was biding my time though, watching my stack dwindle as I waited for my hand. Then it came, a straight flush, Jacks high. I went all in, confident that this would be where I got back in the game.

Frank said "are you sure that's what you want to do? If you lose, you're out."

"Oh, I'm sure. Shoot, if I had more chips, I'd still go all in." I knew I shouldn't have been talking all that trash, but I couldn't resist. I wasn't trying to bluff, but I was trying to draw them in, just to see what I had.

Tom folded. I wasn't surprised though. He'd been playing smart and, as the chip leader, he didn't have to make foolish bets or risk his chips. "It's on you Frank. What you gonna do?"

Frank pondered his cards. Even though my bet wasn't substantial, it was enough that if he lost, he'd be at a serious disadvantage against Tom, and he'd be in danger from me too. "I'll take the bet Jo...but my question to you is, how confident are you that you're going to win this pot?"

"Pretty confident. I'm about to take your money and I'll be very happy to do it."

"Alright then. How about we up the stakes a little?" Frank asked.

"With what? You already know that I'm all in." I responded.

"True dat. But I'm willing to go all in against you because I don't think you've got the cards to beat me." He was cocky and I started to get a little worried, but I had confidence in my almost unstoppable hand. I pondered his proposition for a minute, before answering "What are your stakes?"

"If you win, obviously, you're in the game and it's down to you and Tom. But if I win, then you have to do whatever I say for the rest of the night. Bet?"

Hastily and anxiously I answered "Done."

"Alright. Show us what you've got!"

And I laid out my straight flush feeling excited and happy to be back in the game. I just knew that I was in and I had a chance to make a run at Tom. But the glee on my face quickly turned to dismay as Frank slowly grinned and turned over 1 card after the other: 10-hearts...J-hearts...Q-hearts...K-hearts...A-hearts. And there it was. A royal flush sending me away from the table a broken man.

"That's alright Jo. I won't make the rest of the night too hard on you." Frank had to stop himself from cackling with glee. Even Tom couldn't resist a smile. "Jo, are you man enough to stick with the bet?"

"Yeah, yeah. Whatever you say for the rest of the night. What's first?"

"Well, since you've been talking trash, why don't you start by taking out the trash. But try not to slip out there. It's wet and dirty and I'm not letting you mess up my house if you get dirty."

"Fine. I'll be back in a few minutes." And I got up to gather the cans and pizza remains into the trash, empty the kitchen receptacle and head out to the cans in the yard.

Frank hadn't been kidding when he said it was slippery though. I had to cross the lawn in the rain, and no sooner had I made it halfway down the lawn when I slipped in a puddle and fell flat on my ass. "Great, there goes a pair of pants." But the grass was so wet that I soon felt the rain and water from the lawn soaking through the rest of my clothes. "Why in the hell does Frank have to live in a house so far back from the road?" I grumbled. After finally dumping the trash in the cans at the street, I huffed my way back up the gravel driveway to the house.

"Hey Frank, you got something I can change into? I got soaked out there and need to run my clothes through the wash."

"Yeah," he yelled. "Throw your stuff in the washer in the garage and I'll leave you a robe by the door."

I stripped in the garage and stood there shivering and naked. "Hurry up, would you? I'm freezing out here!"

"Here you go," Frank said with a smile.

"What's this?" I asked with a dumbfounded look on my face. What he'd handed me was like a silk kimono that would only come down to mid-thigh.

"That's the only robe I've got that will fit you. I'm sure you'll look cute in it." And with that smile on his face, I heard Tom start laughing in the background.

"Ya'll aren't funny. Get me some real clothes."

"Dude, the only stuff I've got that will fit you is some leftover stuff from the last girl I was dating. Can I help it that you're short?"

Tom decided to add his two cents saying, "Hey Frank, why don't you just order Jo to wear that stuff? After all, he lost the bet and has to do what you say for the rest of the night."

"That's right," Frank said as he looked at me with a glint of mischief in his eye. "For tonight, you're mine." I felt a sense of dread at what was coming next. "Put this on, the go take a shower. There's a bottle of nice smelling soap that my girl used to use. Wash with that, because tonight, you get to be the girl. How much of a girl you are depends on you. I'll leave some stuff for you to wear in the bedroom."

And just like that, an innocent bet took me towards a night I would never forget.

After I showered, I went to the bedroom and found 3 different outfits numbered and laid out for me to wear. The first included a baby blue teddy, matching thigh-hi stockings, a darker blue minidress, and some matching 3" heels. The second was the classic schoolgirl outfit with a red pleated skirt, white thigh-hi stockings, mary-jane heels, and pink cotton panties and a pink camisole to wear under the white blouse. The third outfit had sex written all over it. It was a black corset with a black g-string, black thigh-hi stockings, and black 5" pumps with an ankle strap. I assumed by the numbers that I was supposed to put them on in the assigned order for Frank and Tom's amusement. As I slid into the first outfit, the teddy fit snug and the stockings felt smooth. The dress hugged my figure and the shoes made my legs look toned and touchable. It took me a minute to adjust to walking in them because it felt like they forced me to tilt forward a little bit.

"You coming out Jo?" Frank yelled. "I figure this is a show we've got to see."

"I'm coming, I'm coming." I said as I stepped out the room. Then a flash, and another and another. "For our memoirs" Tom laughed. "Oh yeah. I'm loving this." Frank added. "Hey Jo, why don't you get us some drinks and make us some sandwiches while we finish off this game? I'm feeling so good that if I win, I just might have Tom join you...then I'll have 2 girls for the night!"

"That's what you think Frank," Tom said. "If that's how you want to play it, then I guess I'll just have to whup that ass, take all your money, then figure out how to take my own revenge." Tom laughed, and so did Frank. I grumbled and groused as I went through the kitchen, fetching beers and making sandwiches.

Finally done, I took the sandwiches out to the guys who were going back and forth with the game. I pulled up a stool and sat down.

"Cross your legs Jo. I don't want Tom getting any ideas."

"You wouldn't go there anyway. I mean this is all fine, but there's got to be a line somewhere." I said.

"Oh really?" Frank got that gleam in his eye. "Come here."

"No."

"Come here."

"No."

"Tom, I think Jo needs a little lesson in obedience. Care to lend a hand?"

"Oh absolutely. We can finish up this hand later."

Then they rushed me from the table.

"Get your hands off me! You guys are taking this way too far. Let me go!" I yelled as I squirmed and tried to fight them off. They threw me across the table and held my hands behind my back.

"Tom, get me the duct tape."

"Right here playa. First, let me have a piece to quit her down."

"Wait. Stop. I'll be good." I tried to plead with them. But to no avail. Tom placed the duct tape over my mouth, and for the first time, I got a real appreciation of how effective a gag it could be. Then Frank took the tape and tied my wrists together behind my back.

"There we go...almost. I've got another idea. Tom, go into the top drawer on the left, fill the hot water bottle with warm water, then bring the 'special' attachment." Frank continued to hold me down as I squirmed, but I couldn't get any leverage. My muffled moans and cries went unanswered as Tom prepared the bottle. Frank began to massage my ass, then unexpectedly, he spanked me. Hard.

"That's for being so hard-headed. I imagine there will be more of that tonight." Then forcing my legs apart, Frank found my asshole and began to force the nozzle up my rear.

"MMMPPHH!!!"

"Stop squirming and relax otherwise this will hurt more." Frank said. Once he got the nozzle firmly secured up my rear and in my teddy, he brought my legs back together and duct taped them together. Then, he made me sit down on the other chair at the table while he hung the bottle on a hook on the wall.

"Comfy Jo?" he asked with a smile. Tom sat there smirking then said "we've got to get her into some other positions later on."

"Oh, there will be plenty of time for that...plus a few other things." Frank added. Then they sat down and continued playing there game.

As the water bottle empty into my rear, I began to squirm from discomfort. My insides started feeling full and I really needed to go to the bathroom. I began to mew soft pleas that caused them to look up.

"Jo, I didn't know the bottle was almost empty. Here let us refill it for you." And I looked up in horror as they replace the first bottle with a second. The tears started to fall from my eyes as I scooted around. My mews became cries and grunts, begging for relief. Finally, the second bottle was empty and I felt like I was going to burst. The guys looked at me, at my distended stomach and began to laugh.

"Come on Frank. Let's give our little lady a break and take her to the bathroom." No sweeter words had ever been spoken. But as Tom hoisted me on his shoulder, all the liquid inside shifted and I began to cry again from the discomfort. Finally, they laid me across the sink.

"Jo. You better hold all the water in while we remove the nozzle. If you don't, there will be a serious price to pay." Tom said.

And I tried. I really tried. But as they removed the nozzle, I felt it begin to leak. I tightened my sphincter and could hear them laughing as they watched me try to keep it in. It probably helped that my legs were bound together, but I got to the point where I couldn't hold it any longer and the water started to run down my legs. "Dammit Jo." Frank exclaimed as he roughly moved me over to the toilet. "Go ahead. Let it out. Feel better now?" he said with disgust in his voice.

The relief that I felt as I was able to let my insides empty was apparent all over my face. "Tom, since she made such a mess, would you be so kind as to go and get the schoolgirl outfit so we can change her?"

"My pleasure Frank."

A few minutes later, I found myself tied to the shower curtain pole with my legs spread by a bar. I was naked as the guys had seen fit to strip me in preparation for the next part of the night. One by one, then slid the next garments on me. First the white thigh-hi stockings. Then the black mary-jane shoes. Then they took my arms down to get the camisole and blouse on. Finally they slid the skirt up my legs.

"Leave the panties off Tom. We're going to have a little fun here." Then Frank started to fondle my dick. Caressing it till it grew hard in his hand.

"Guys, really, what are you doing?" I asked.

"Taking advantage of the bet Jo. You know that. Now be quiet." And with that, Tom grabbed a ball gag from out of nowhere, forced in my mouth and silenced me yet again.

As Frank held onto my hardening dick, he produced some kind of ribbed butt plug that was attached to some kind of cage for my dick. Quickly, he put the cage on my dick and explained, "this will keep you hard, but it won't let you come." Then he lubed the plug and forced it into my ass. I grimaced with pain then my eyes grew wide as he turned it on. I didn't know it was a vibrator until that moment when I felt the sensations from the back to the front.

"There, that ought to be fun for awhile." My body started to twist to get away from the sensations that were running through it, but there was nowhere to go.

"Tom, untie her feet from the bar, then tie them back together. Knees too." After Tom did that, he undid my hands from the shower rod and tied them together behind my back. As they carried me back to the living room, they laid me down on my stomach on the couch. My dick was stuck beneath me, hard and caught between my skirt, my stomach, and the couch. Tom took my ankles and brought them towards my hands as he hogtied me. I grunted and moaned as the sensations from my ass made me shift and struggle. Only, it didn't make things any better because the rubbing was stimulating my dick.

"Watch her Tom. I think she's enjoying this."

"Oh I'm sure she is. But she's just not getting any relief is she."

"Not right now she's not. I bet she wishes she could come though." Frank laughed.

And I did. I was so uncomfortable and feeling victimized, yet I was still stimulated. I didn't have any control and couldn't get any release. Finally, after about 20 minutes, Frank came over and released the cage on my dick and I spurted come all over my stomach, skirt and his couch. I grunted with relief as my dick softened, even as the sensations continued in my ass. I panted with exhaustion at the surprising exertion I'd experienced when Tom came and freed me from the hogtie position. I remained bound though as they flipped me over onto my stomach, then sat me up.

"She really is kind of cute, isn't she Frank?"

"Yeah, we should show her how to really appreciate men though. I mean, now that she's gotten hers, we should get ours."

"True, true. I always hate how girls say we never worry about whether or not they come. Here's one that ought to be satisfied."

I was nervous about what was to happen next because I knew it could really only be two things...either they were going to make me give them blow jobs or they were going to fuck me. How little did I know.

"Flip her over the couch."

And with that, they had me standing behind the couch, bent over with my hands tied behind me and my legs tied together. Then Frank removed the ball gag from my mouth and said "a little something for you to gather your strength." Next thing I knew, he had inserted his penis into my mouth and I felt it growing until it filled up my entire mouth and I thought I would gag. Slowly, he began to move back and forth, fucking my face slowly.

"Go ahead Tom. Have at it."

Then Tom, standing behind me, began to force his dick into my ass. It was bigger than the vibrator and longer and because my legs were together, he had to force himself harder. My groans were lost in Frank's pubes as Tom got himself situated into my ass.

"Shit Frank. You oughta be riding back here. It's nice and tight and it feels just right." Tom laughed as he continued his ride. Frank smiled back at him as he said "Don't worry. I'll get my turn riding soon. Right now, I'm just enjoying her nice, warm mouth. I guarantee, you won't be disappointed when it's your turn up front." And with that, they continued their respective pumping, getting their push-pull rhythm in sync until I started to get lost in the overwhelming sensations.

"Tom, I'm about to cum...you almost there?"

"Yeah Frank. Ready when you are."

"Okay then...1...2...3...awww, shit that feels good." And Frank spurted down my throat. Stream after stream, jet after jet. It started to overwhelm me, and as I struggled not to choke, it started to seep out the corners of my mouth. At the same time, I felt Tom cumming in my ass. I felt the warmth deep inside, filling me, making my insides wet and seeping down my legs. Then, by surprise, I felt my own orgasm spewing as my cock rubbed against the top of the sofa, caught between my skirt and the cushions. "MMMPPPHHHH!!!" was all that they heard.

"Frank, I think Jo came too. Was that what that was? Did you like your ride Jo?"

As Frank pulled out of my mouth, I begged them "no more, please no more. You guys can't keep doing this to me."

"Oh, but I think we can Jo," said Frank. "After all, the night's not over, and I've still got big plans for you." Tom smiled at Frank's insinuation, and I couldn't help but wonder what else they had in store for me.

"Quick Tom. Grab the vibrator and shove it up her ass. We don't want her to lose all her lubrication. She's going to need it."

"What's the plan?"

"First, change her into outfit number 3. Then take her to the playroom in the basement."

"What playroom?" I asked. "I didn't even know you had anything down there besides storage."

"My bad Frank. Here's the vibrator and the gag. I don't want to hear her mouth, but I do want to hear her moans and squeals once we get her into your playroom." Tom was just a bit too excited about the room, and I started to get scared.

They dragged me back into the bedroom and stripped off the blouse and skirt. They gripped each arm in a wrestler's hold while they removed the camisole. They switched the mary-jane shoes with the heels with the ankle straps, and the panties, they simply tore off. "Let her keep on the white stockings. It will be a nice contrast to the black outfit. A little trashy, you think?"

"Oh yeah," said Tom. "That will work just fine. As a matter of fact, I think I remember seeing a black and white corset that might tie the whole look together. What do you say Frank?"

"Find it and let's do it."

A moment later, Tom came back in the room with the corset he had found. As Frank held my arms behind me, and my legs stayed bound, Tom slipped the corset around me, then began lacing it up. "Do it tight Tom. I want to see her sexy little hourglass figure." Finally, tight enough that I felt I could barely breathe, I stood wobbly and bound, but Frank wasn't finished.

"For this next part, I've got a couple more surprises Jo." And with that, he taped my wrists together, then wrapped them in a sheath that covered my hands and my arms up to my elbows, pulling my arms back and forcing my chest out.

"There we go. Tom, if you'll be so kind as to get the door, I'd be happy to carry Jo down to the playroom." And with a smile, he tossed me over his shoulder, moving the vibrator in my ass as he followed Tom down the stairs.

"Are you ready Jo?" Frank asked.

I tried to squeal out a "No" and begged for them to stop, but the only thing that came out were squeals and grunts.

Frank set me down in a special kind of chair. I knew it was special because my sheathed arms, while under me, were not uncomfortable. I wondered what he was going to do when he suddenly pulled a strap around my waist, effectively fastening me to the chair. After securing my torso to the chair, Frank began to untie my legs. As he did, Tom came over and moved one leg into a stirrup, while Frank did the other. Then they fastened my legs to the stirrups, immobilizing me. Frank took out the gag...

"Frank, Tom, what are you guys doing to me? I mean, you've already had plenty of fun. Please just let me go. I think this is taking the bet a little far." I pleaded with them.

"Shh. Jo, it's okay. Actually, you can make all the noise you want down here. The room is soundproof. As for now, now we trade. One more round of 'fun in Jo', then we'll let you rest for the night. Tom, you take the front, and I'll take the back." All of a sudden, the bed tilted flat, and the part supporting my head disappeared and I found myself looking at Tom, upside down. I felt Frank spreading the stirrups and pushing them back so that my asshole was pointed just right before he plunged in.

"AHHHH" I managed to get out as Frank plunged in before Tom forced his cock into my open mouth. And they started again, fucking me from both sides. I could have sworn I heard them hi-five each other, but I couldn't see anything but Tom's legs. Harder and harder they pushed. Faster and faster they went. Time was immeasurable and I knew they'd take longer this time around since they'd already come once. Still, I could feel them tightening up as they started to cum. On and on, until finally they both let out large grunts, repeated again and again as they pounded harder and harder, eking out every drop into my throat and ass. Finally they were through. I gulped in air and felt woozy.

12
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