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A Lost Bet Ch. 01

By: amarasfantasy



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.


A Lost Bet Ch. 01



"How about a game of poker?"

I looked over at my dad. He is attractive and quite youthful for someone who is forty-six years old. He has black hair and blue eyes and the kind of smile only an entrepreneur can carry. He owns seven five-star hotels and makes a very decent living. 

I am enrolled in graduate school in hopes of becoming an actress for Hollywood one day. Like my mother, who has been deceased for four years now, I have long white hair and light blue eyes that matches my milky white skin perfectly. I have always been skilled at acting, and I have the looks of a model, so between the two I am hoping I will soon be in the movies.

My mother was who I got all my looks from. Unfortunately, she passed away after a long, cruel fight of lung cancer. I was furious when she got diagnosed. She did not smoke, nor does anybody else in our immediate or extended family for that matter. How she got lung cancer was a complete mystery.

"Sure."

"I have an idea to spice things up a little bit."

I looked at him suspiciously. "And what might that be?"

He grinned. "We make a bet. The person who wins all the chips gets to request anything from the loser and the loser has to do it no matter what."

He must want something if he is making a bet like that. He has been talking about going camping for months now and every time he brings it up, I tell him no. I hate camping. I would be bored out of my mind for a week with just him and the twins.

The twins are my younger brother and sister, Travis and Kara. They are seniors in high school this year, which means they graduate this coming spring. Both of them have my father's black hair but they both have silver eyes instead of blue eyes. Travis has a lean, athletic build and Kara has a model figure like I do. They are extremely close to each other, which I admit does make me a little jealous.

I opened my mouth to turn him down but an idea popped up in my head. I have been dying to get a new car and if I win, Dad has to buy me a new one, even if it's a BMW.

"Alright deal. If I win..."

"No! We don't tell each other what the request will be! It will be more fun this way."

I rolled my eyes. "Like I don't know what you are going to ask for anyways."

He smirked. "I wouldn't be so sure if I were you."

We started the game. It continued for four hours, and it seemed to be going nowhere. Every time I played a good hand, the next one he did. The game was not going anywhere. I looked at the hand that I was now holding. I was holding a flush. I made a bold move and put in all my chips. 

"Winner of this hand takes all."

"Agreed. It doesn't seem like we would be able to finish tonight otherwise." He put in all of his chips.

"What do you have, Hannah?"

"A flush!," I exclaimed triumphantly. I can smell the leather interior of my new car already.

"Sorry Hannah, but I win."

"What?!"

He laid his hand down and he had four threes. My world came crashing down. No car. Camping. Shit.

"Alright. When do you want to go camping?"

"That wasn't what I had in mind. But before I tell you what I want from you, you have to tell me what you wanted from me. There must be something really wanted if you agreed to this bet."

"A BMW."

He laughed. I was starting to get annoyed.

"If you don't want to go camping, then what do you want?"

"The thing that I need from you is you."

"What?"

"Because I won, you and I now are going to be lovers until the day I die."

"WHAT?!?!"

"I haven't had sex for over four years, Hannah. Your mother was the last woman I have been with. I am sick of relying on porn and jacking off to get release. To tell you the truth, I have wanted you way before your mother died. I discussed it with her and she told me to wait until you were a legal adult before we fuck. It made perfect sense to me. I would wait until you are all grown up so that I had no guilty feelings and you could make the decision on your own."

"Okay, let me get this straight. Not only have you wanted to fuck your daughter since she was a teenager, but you discussed it with your wife and she said it was alright as long as you waited until I was old enough?"

"Pretty much."

"What the hell? Do you want to fuck Kara as well or is just me?"

"I thought I should be with you first since I have wanted you longer and I don't know if she is still a virgin or not. But in time I will definitely fuck her if she consents. I don't want to be her first. You are pretty open with your sex life with me thankfully. I know you have been with at least a dozen men."

That is an understatement. To be exact, I have been with twenty-eight different men and nine different women. I prefer men, but sometimes its fun to mix things up a bit. Luckily I have never contracted any diseases or gotten pregnant yet.

To make things even more funny is that I have had my boyfriend I am with for ten years. We have dated since we were fourteen and when I turned seventeen I cheated on him. I cried my eyes out and confessed my betrayal to him. To my surprise, he gave me a hug and a kiss and said he doesn't mind. He told me there is nothing wrong with having sex with multiple partners as long as the other partner is alright with it. He suggested that we both should try sleeping with other people and we tried it and we both loved it. Cody sleeps with as many people as I do and we are perfectly happy in our relationship. Like me, he sometimes sleeps with people of the same gender but prefers the opposite gender. Sometimes we have threesomes or orgies when we are extra horny.

"It is wrong, Dad."

"Why? Because society says it is? I don't see why so many family members suppress their sexual attraction to each other. And don't even try to tell me that Cody will have a problem with it because we both know he would be amused if anything."

I thought about that and agreed with him. Cody would laugh his ass off, strip me down, and fuck me if he found out because it would probably turn him on. Anything kinky like that always turns him on.

I looked over at my father who was now standing ten feet away from me. I decided to check him out as a man instead of as my father. If I hadn't known him, I would have pegged him as middle thirties instead of middle forties. I looked at his skin and it looked perfectly firm, the way a man's skin should be. I looked at his mouth and it looked promising, waiting to devour me. I shivered. I know without a doubt that mouth could do wonders on my clit. I looked down and found his muscular upper body. His pecs could be seen through his thin shirt and his biceps would be hard to miss. I mentally stripped his shirt off, knowing he had fur on his muscular chest. I wanted to run my mouth and hands all over it.

"God, Hannah. I have wanted you to look at me like that for so long."

I shifted my eyes and blushed. I had been giving him googly eyes longer than I should have.

"Don't look away! My body has been craving for your attention for so long, baby. It would end me if you ignored it now."

He won the bet and this is what he wanted. What kind of person would I be if I did not give him what I promised?

I looked back over at his upper body, imagining it naked. I imagined that he had just gotten out of the shower and his fur was soaked, hair getting thicker and darker as it lead closer to his groin.

And then my eyes were off his upper body and fixed solely on one spot: his genitals. The genitals that I have to thank for giving me life. I am alive only because of his penis and testicles. I would not be here today without them. I can't believe that I have been alive for twenty-four years and not properly thanked them. It was time to start thanking them now.

I walked over to him and got on my knees before him. My face was inches away from his cock. I covered the distance and massaged my face against his groin. He moaned.

I reached up and tried unbuttoning the top button of his jeans. He suddenly reached out caught my wrist, preventing further movement.

"Not here. We need to do this in the bedroom our first time. I want it to be perfect for you. Which one do you want to go to?"

I almost said my room since it was the closest, but I remember that my dad had a king-sized bed with red silk sheets. "Your room."

He led the way.

When we got in the room, he shut the door and quickly grabbed me by the shoulders and flung me against the wall. I let out a surprised yelp and his mouth was immediately on mine. He probed me with his tongue and I granted him access. His tongue kept on thrusting its way in, wanting to go as deep as it could. I kissed him back, thrusting my tongue encouragingly at his.

After a few more minutes of passionate kissing, I broke the kiss and shoved him towards the bed. He let me push him onto the bed. I grabbed for his shirt and tried stripping it off him. He helped me and when it finally came off, he threw it across the room.

Finally his chest was mine to explore. I began running my hands through his fur, enjoying the feel of his muscles. I leaned down and licked and sucked on each nipple. He moaned and I continued down his chest and past his belly button, finally reaching the top of his pants. We were both breathing loudly in anticipation, not saying a word.

I took his belt off, and he lifted his waist off the bed so that I could toss it aside. I unbuttoned his jeans and slid the zipper down. I dragged his pants down his legs and took them off completely and tossed them to the side along with his socks.

"Lets pick a better position so I can give you a blowjob."

He didn't argue. He just sat on the edge of the bed while I knelt in front of him, giving me easy access to suck his cock.

I wanted to see the entire package at once, so I looked away and grabbed the top of the waistband of his boxers, sliding it off him. I lazily tossed them aside, trying to build the nerve to finally see him completely naked.

"Look how ready I am for you, sweetheart."

I looked at him and gasped. He had the hugest cock I have ever seen! And I have seen a lot of cocks.

"It must be ten inches!"

"Ten and a half inches, actually. Your mother measured it. It is eight and a half inches round. This cock is always hard like this when you are around. It wants to be sucked by you."

I owed my life to this cock. I wrapped my hand around it and started stroking it. I still can't believe how huge it is.

"In your mouth, Hannah. Please."

I slid his cockhead into my mouth, sucking on it gently. I took it out and licked it slowly from the base to the top. I continued licking it, enjoying the taste of my father's cock. I then took it back into my mouth, and took it into my mouth as far as it would go.

"Fuck yeah!"

My dad reached for the back of my head and started a pace that he found the most pleasurable. God knows I love sucking cock.

This continued for a few minutes, then I took him out of my mouth, slowly. I pumped him with my hand a few times and I watched precum ooze out of the slit that I once came out of. I let it drip until it reached past the head then I started at the bottom and licked its way back up to the slit. It was delicious, and I wanted more of that salty goodness, so I continued sucking on his cockhead.

To my surprise he pulled out of my mouth and backed up on the bed. "That is enough for now. I do not want to cum in your mouth the first time."

"But I want to taste it in my throat," I argued. "I haven't shown you my best yet."

"Maybe next time." He added, "I want to suck your tits."

With that he quickly reached up, pulled me down to the bed, and got off the bed. He looked down at me with lust in his eyes. Him standing completely naked and hard before me, looking all dominant like that gave me the urge to spread my legs for him.

He reached down, grabbed a hold of my blouse, and ripped it open. I let out a gasp. He finished tearing it off, looking at my bra-covered breasts with hunger.

"Sit up and take your bra off," he demanded.

I sat up, reached back, and unclasped my bra, letting it fall off my breasts. He grabbed the bra and tossed it aside and shoved me back down on the bed. He possessively grabbed and squeezed my breasts.

"Mine," he said. "Just like your mother's. You have perfect tits."

He reached downed and put his mouth to work. He used every technique all the men I have been with have used, plus a few more I have never experienced. Sucking, brushing, biting, licking, you name it, he did it. I felt an orgasm approaching. He continued fondling my breasts.

"Who do these belong to?"

"Me," I answered.

He bit my nipple. "Wrong. Who do these belong to?"

"Cody."

He bit my nipple harder and I experienced pain mixed with pleasure . "Absolutely not. Who do these belong to."

"You."

He licked the pain away and continued with a combination of licking and sucking. An orgasm was just around the corner. "That's right. Who do they belong to again."

"You."

He moved onto the next nipple and started licking and sucking it. I was breathing loudly, needing sweet release. "One more time."

"It's your's, Daddy! All yours! Yours and yours alone! They were made for my daddy alone!"

"Don't you forget it."

He licked and sucked and it continued building. I started moaning and the orgasm was so close. Then it hit me. Wave after wave of pleasure came crashing through my body. I have never had an orgasm this strong without stimulation to my vagina. He continued until the tide subsided.

"Are you wet?

"I make the ocean look dry."

"Good. Its time to fuck."

We ripped the rest of my clothing off as soon as we could. It was a blur that I couldn't remember if I tried. I am completely naked for my father. I spread my legs far and wide for him. He positioned himself above me and pressed his cockhead against my entrance.

"Are you ready, Hannah?"

"Yes, Daddy."

He pushed his shaft through my sheath ever so slowly, stretching it wider than it has ever been stretched before. I waited for him to reach the bottom of his base and feel the slap of his balls. His cock seemed to never end. It was going to come out my mouth if it went any further. Then I felt his base and the feel of his balls on my ass.

He continued sliding himself slowly in and out a few more times. I got adjusted and was ready to go harder and faster.

"Daddy, I need more."

He picked up the pace, faster and harder with every thrust. I felt my sheath put a death grip on his cock, but it was relentless. It never stopped shoving its way through. I began to have another orgasm.

"Yes, Daddy, yes, yes, yes!"

"Fuck yeah! That's my little girl. Knows how to keep a grip on my big, fat cock!"

He continued fucking me hard and fast. I could hear his balls slapping into my ass.

He slid out of me.

"Daddy! Don't stop!"

"Tell me you love me."

"I love you, Daddy!"

"Who do you belong to?"

"You, Daddy!"

"Who fucks you better than anyone else?"

"My Daddy!"

He shoved his cock back into me. "Who's penis is in you right now?"

"Daddy's!"

He continued shoving his cock in and out.

"Who are you making love to?"

"Daddy!"

He fucked me hard and fast. I enjoyed the feeling of being impaled, fucked.

I felt my sheath tighten on his dick and I had the most powerful orgasm I have ever had. My vagina continued milking his shaft and I felt him come inside me. Jet after jet came pouring out of him into me. I felt amazing.

He rolled to the side and I rested my head on his sweaty chest.

"We need to do that again sometime."

"We will, Hannah, my love. I promise."

To be continued...



A Lost Bet Ch. 01



"Please, just let me up. I promise I won't say anything to anybody."

"You're damn right you won't. If you do, you have no idea what will happen to you. We tried to make this enjoyable for you, but you just won't stop begging like a bitch." Frank was obviously getting tired of my pleas for help. "You know, I was going to let you up, but instead, I think I'll just leave you here with my special friend...the machine."

"Frank, I didn't even know you had one of those. I always wanted to see one."

"Well, gag Jo while I set it up." And the ball gag came back. Then, I felt some pressure on my ass...again. I looked up and Tom snapped the head rest back into place. He said "since you're going to be here for awhile, you might as well be comfortable." Then Frank shoved the dildo attached to what looked like a large drill into my ass.

"Jo, this is 'the machine.' I'm going to turn it on and set it for 30 minute increments. That means, it will fuck you for 30 minutes, then shut off for a random period of time. At least for the first 3 cycles. After that, it's all random. Oh, and one other thing. Actually two. First, over the course of the night, you'll find that the dildo changes size at random. It's inflatable. It won't get much smaller than it is now. Stop shaking your head. Right now it's my size and I KNOW how much you enjoyed riding me. But it will get larger. The second thing is that it's hooked up to an ejaculation mechanism. That is, the machine will cum. It's kind of a mix of cream and water. That will help keep you clean and lubricated. I imagine that by the time we come down in the morning, you'll really have to go to the bathroom, but there shouldn't be too much of a mess. Are you ready?"

I was furiously shaking my head no as tears ran down my eyes which were pleading for them not to do this to me. Then they switched the machine on and I squealed like a girl. I grunted as the machine pumped into me. They watched for a few minutes, until I passed out. I remember waking up periodically through the night to the pumping, but also to periods of calm before the whole process began again. I couldn't understand what had happened but I knew I wanted things to end. But when would it?

To be continued...



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.




A Lost Bet Ch. 02



"Frank, you take the back bedroom. I'll take the master bedroom off to the left. Jo, you get the front bedroom. Hustle up and let's get everything inside before it gets too much colder," said Tom.

We hustled. We really only had to take in our ski equipment and bags (their luggage and my shopping bags). There wasn't any food in the house so one of the guys was going to have to go shopping.

"I'm going to run out and grab us some food for the week," offered Tom. "That will give you two time to explore the place and get started with...whatever it is Frank has in mind." And with a wink and a nod, Tom took off.

Frank smiled as he looked at me. "Jo, we are going to have some real fun with you this week. You can fight it if you want, but if you just relax and accept the week for what it is, you might actually end up enjoying yourself, alright?"

"Yeah Frank. What-e-ver" I responded cynically. 

"Fine, be like that. Just know that the activities are about to begin. Go sit down on the sofa. I'll join you in a minute." Frank then disappeared with his bags into the back bedroom. I carried mine into the front bedroom, then skulked my way back to the sofa. I really didn't want to know what Frank had planned but it really didn't matter. I already knew that I was in for a very different kind of week.

After about 30 minutes of watching TV and waiting, Frank finally emerged from his bedroom with a bag in hand. "Here Jo. These are some of the things that I brought from home for you. Now it's not everything, because I wanted to keep a few things as surprises. But what you will find in the bag are a few different outfits...some for wearing in public, some for here in the house. Believe it or not, you do have some flexibility in choosing what to wear...at least until either I or Tom ask you to put on something else. Also, during our time up here, you will be asked to perform various...tasks. If you refuse, there will be consequences. I need you to understand that."

"So basically, I'm your slave for the week." I retorted.

"Slave is such a harsh word Jo," Frank said. "Honestly, you can leave whenever you want. We don't want you to feel totally trapped."

"Of course, if you leave, you'll leave wearing only the clothes on your back," Tom added as he set down the groceries. "It's probably a mile or so to the nearest cabin, and it gets pretty dark and pretty cold up here at night. And I think I actually heard some reports about mountain lions roaming around. Basically, I wouldn't recommend it."

"Fine, fine," I grumbled. "Let's just get on with it."

"Jo, Jo? What's the rush? We've got all week long to play. Think of this as a vacation," Frank said. "It's a whole week where you can do whatever you want or whatever you're told to do without fear of judgment and without worrying about what would happen if anybody finds out. The only people in the area that know you are sitting in this room, and even though we took advantage of you (yes, we can admit that), we're not out to hurt you. Just try to have a good time over the next few days."

"Yeah Jo," added Tom. "Outside of times like this, you know we'll still treat you the way we always have. No big deal."

"You guys can stop trying to convince me because it's not going to work. But that doesn't matter does it? We're here now. You're getting what you want. So, what is it you want me to do first?" My attitude just continued to be sour even though the guys were being semi-nice to me. I couldn't help feeling cheated though. This just wasn't right...

"Well Jo," said Frank, "the first thing is to get you out of those clothes. I mean, you look cute and all, but I'd like to see you in something a little sexier."

"And what would that be?"

"Why don't you go in your bedroom and find out. The outfit is the top one in the bag."

"Fine," I huffed as I carried my bag into my room to change. 

Once I got into my room, I opened the bag to find a black garter belt and stockings, a black thong and bustier, the heels with the ankle straps, and a long, royal blue Chinese-style dress. Even I had to admit that the dress was beautiful. As I changed, I heard muffled voices coming from the other room, but I paid them no mind, figuring that I'd find out what the guys were talking about once I got out there. Putting on the garter belt and stockings first reminded me of the first time 3 months ago. That same silky feeling was there, but this time I allowed myself to feel the soft rustle of my legs brushing against each other. I still stubbornly refused to get into the act, but I couldn't help but acknowledge what I was feeling...I guess it was a little "naughty." I quickly put on the panties and bustier. The next step was the heels. Once I slid them on and had adjusted the straps, I stood up and caught a glimpse of myself in the mirror. From the neck down, I could kind of pass for a woman, albeit one that was not as curvaceous as the models on TV. Still, my figure was good enough that I would have approached me in a club. "I guess the clothes can go a long way in making the girl," I thought. Finally, I pulled on the dress. It reached almost to my ankles with a long slit up the side. I knew that when I sat down or as I walked, the guys would be able to see the tops of my stockings and the attached garters. But this was what they wanted. I stepped out of the bedroom to find the guys chatting in the kitchen. Something didn't feel right, but I approached them anyway.

"Ahem." I cleared my throat and both guys turned to look at me.

"Wow Jo. You look very sexy in that dress. Very...sensual," said Tom.

"Yeah. I'm definitely impressed," added Frank. "That wasn't a bad choice, now was it? Come on, you can admit it."

"I'll give you that Frank. It's a nice dress."

"Good, I'm glad you like it. Please, come and join us."

As I walked over to them, Frank said "turn around. I want you to face the wall and close your eyes." I did as instructed but started feeling apprehensive.

"What are you doing Frank?" I asked.

Then I felt my wrists being pulled behind me, and leather straps being bound around them.

"What? You're just going to try and repeat last time?"

"Shhhh..." Frank hushed me. "Keep your eyes closed. As a matter of fact, Tom, hand me that handkerchief." Tom handed it to him, and he quickly blindfolded me.

"Alright Jo. Time for you to choose. Would you like to have DP...WS...or NC?" Frank asked.

"Could you at least explain what those things are?"

"Nope. Make your choice."

I thought for a minute, considering my situation. 'I guess DP could be Double Penetration so I'm not going to choose that. But what else could it be? And WS, that's got to be some kind of Water Sport. NC...I don't know. Crap. Which one do I choose?' My mind was racing as I tried to predict my fate for the night. 

"Time's up Jo," said Tom. "What's it gonna be?"

"Umm...WS...no, wait...NC."

"Is that your final answer?" Frank joked.

"Yes, NC." I responded.

"Okay. Tom, please help Jo out...of the dress first of all. I hate to see it go, but I'm sure we'll find a way to get her back into it soon enough." Tom did as he was asked.

"What next Frank?" He asked.

"Now, please grab item number 1 from the table and help Jo into it."

I was standing there, in my underwear waiting for Tom to act. First, he took off the blindfold. Then he told me to keep my eyes closed. Then, I felt a silken hood being placed over my head, only it was tight and form-fitting. I started to speak, but Tom forced my mouth shut. I heard a zipping sound and felt my head encased in silk. I tried to open my eyes, but there was nothing to see. It was black and I was sightless. I tried to speak, but the mask came up under my chin and allowed no jaw movement. I could mumble and moan, but that was it. 

I felt hands on my legs, spreading them apart when all of a sudden I heard two quick clicks. I tried to move my legs, but felt them stuck almost in place by what could only be a spreader bar.

"Tom, please grab item number 2 from the table." I heard Tom moving around then I felt him close to me. He moved my panties aside while he grabbed my penis. "Just so you know," he whispered, "one thing that NC means is No Climaxing." Then, I felt him affix some kind of device to my penis and balls. I wasn't sure what it was, but he'd made the items intent clear. 

"Oh, one more thing Jo," said Frank. "NC also means Nipple Clamps." And I felt Frank pulling my nipples out of the bustier. He massaged them, even licked them to try and get them aroused. As they began to respond to his ministrations, I felt a pinch on my right nipple. I gasped...as much as I could gasp through the mask. Then, I felt a similar pinch on my left nipple. But it was the tug at the end that caught me by surprise.

"Those are just some light weights we attached. No more than a few ounces, but that should be just enough to keep you aware of them." Frank spoke as I felt him caressing my ass, running his hands all around, before probing with a finger. Just because I want you to get the full effect...and be ready for later...here's one more 'toy' for you." Then I felt him press what felt like a small ball...correction, a string of small balls into my ass. The string must have been 10-12 balls in length. I could still feel one outside my ass, but pressed up against it, while the others shifted inside me with every small shift. 

The last thing they did was lean me over the sofa for support. I felt them lift my wrists (which were still bound together) and tie them to something. Whatever it was, I was forced to stay bent over.

"You know Frank, that's a beautiful sight we've got there. What are the plans?" asked Tom.

"Well, now we start her up, have something to eat, then relax a little before bedtime. After all, we've got a full day of skiing ahead of us." 

All of a sudden, everything in my ass starting buzzing and it turned out that the balls were actually mini vibrators. They hummed and purred in my ass and I started to get excited, even though I didn't want to. That's when I felt the pain in my dick. I grunted and squealed in protest and discomfort.

"I told you Jo. No cumming." Tom laughed.

I had never been so uncomfortable. They must have left me there for an hour while they ate and talked. I never managed to get used to the vibrating beads because every time I did, the beads shifted positions. Or, as if that weren't enough, Tom or Frank would come by and pull on them, causing them to shift locations and sending new sensations running through my ass. 

Finally, they finished eating or doing whatever it was they were doing and they turned to focus their attention on me. I felt their hands on my ass and head, caressing me and pinching me and teasing me in different ways. My moans and protests were lost in the mask. I still couldn't see anything, but I felt hands pulling at it. I heard the zipper being undone, and then slowly, the mask was lifted off my head and my hands were released from their ceiling hook.

"Ooh," was all I could manage to say as I reveled in the ability to once again speak and see.

"Doing alright there Jo?" asked Tom with a grin on his face. 

"Please, let me up. I'm stiff and sore and my ass hurts." I begged and pleaded with them. "haven't you guys had enough fun for the evening?"

"Not even close Jo," said Frank. "Not even close." And with that, he started to deliver a few hard smacks to my ass.

"Ow...ow...ooh...stop...oh God...stop...ow...ooh...no...stop..." With each smack, I cried out. It didn't help that some of his smacks came right on the vibrating beads hanging from my ass. 

"Aw, Jo. Are you not enjoying yourself?" laughed Tom.

"Please...not so hard."

"Don't worry," said Frank. "It's almost time for the real fun."

And with that, he slowly pulled the vibrating beads out of my ass. He pulled at such an agonizingly slow pace that my legs literally started shaking as each bead passed through my sphincter. 

"Tom, come on over and undo Jo's right leg while I take care of her left leg."

As they untied my legs from the bar, I tried to raise myself up into a standing position. 

"Ah, ah, ah. You're coming down here now," Frank said as he pulled me down to the floor. He pulled me onto my knees, then spun me around to face him. "Come on Jo, you know what I want."

"Please don't make me do that Frank," I pleaded with tears in my eyes. "Can't I just have a break for tonight?"

"Not yet Jo. Soon, but not now." And with those words he pulled my head down until it was at crotch level. He unzipped his pants and pulled out his dick. He placed it on my lips and said "open wide." Slowly, he forced his dick into my mouth and began to force me to give him a blowjob. I wasn't able to move my head as much because, being in the kneeling position and not having my arms to support myself, I was extremely off-balance. While Frank was fucking my mouth, he held on to my shoulders for support. Tom decided to help out by kneeling behind me and holding my hands, pulling them back and taking some of the strain off of Frank. 

I heard a zip behind me and knew what was next. I tried to look up at Frank with pleading in my eyes, but to no avail. I felt Tom begin to push himself into my ass, then I felt him change position. "That's a good one Tom. I hadn't thought of that position," Frank said. I felt Tom kind of stand up behind me and push down into my ass. I felt a different kind of pressure as he pushed in. But I had a hard time focusing solely on the feeling in my ass because Frank was sliding himself farther and farther down my throat. The minutes dragged on, and in my head, I couldn't help but remember the last time...the first time they had done this to me. I felt powerless to do anything other than wait for it to end. Minute after minute, they pushed and pulled, until I heard them grunting with effort and anticipation as they came...Frank down my throat and Tom deep in my ass. 

"Swallow Jo. Swallow it all." And I was forced to because Frank wouldn't remove his cock from my mouth until whatever was in there was gone. I swallowed the sticky, salty mix and tried not to gag. "That's a good girl," Frank said. Then he pulled his cock out of my mouth and placed it back in his pants before closing up.

I felt Tom softening, then heard the soft, subtle "pop" when he slid out of my ass. Slowly, he lowered me by my arms onto the floor. I could feel his cum leaking out of my ass and running down my balls onto the floor. I lay there feeling used and trying not to cry, when Tom came close and started to release the bonds on my balls and cock.

"Ooohhh..." I moaned as I regained my freedom. "Thank you Tom."

"Sure Jo. Believe it or not, Frank and I actually want you to cum...just not all the time."

Frank came back to loosen the bonds on my arms, setting me entirely free. Unlike the last time, he started to massage my arms and wrists and back for me. I was shocked by the outpouring of kindness from the men who had just finished using me.

"What are you doing Frank?"

"Well, we're pretty much done for the night. I know we could do more with you...to you, but we've got a whole week ahead to play," he said. "Besides, if we're going to ski tomorrow, you'll need a little rest. If you look further into the bag that I gave you earlier, you'll find a couple of nighties, shorts and camisoles, and tampons. Use them, and have a good night. I'll leave your 'apparel instructions' under your door in the morning, alright?"

"Okay Frank. G'night...and g'night Tom," I said as I rose to my feet and stumbled to the bathroom to clean up. Once in the bathroom, I took a shower in order to get cleaned up, inside and out. After stepping out of the shower, I toweled off and put on a robe that I found in the bathroom. As I crossed the hall into my bedroom, I found one of the cotton nighties Frank told me about, as well as some cotton panties to wear. I decided to use one of the tampons, just in case. But as I crawled into bed, feeling exhausted and emotionally drained and hoping for blissful unconsciousness, I couldn't help but wonder what the rest of the week would bring. 

To be continued... 



A Lost Bet Ch. 03



I woke up the next morning feeling a little tired, a little stiff, and definitely sore. But it wasn't the kind of soreness that came from exercise. It was just my rear. The beads and the pounding from Tom had done their job. As I rolled out of bed, I felt the tampon in my rear and immediately wanted to get rid of it. I started to walk but even that felt different. I hoped the feeling would go away, but I didn't that it would because I knew that whatever Frank and Tom had planned for me would probably culminate in some sort of anal experience. As I grabbed my things and made my way to the shower, I heard Frank in the kitchen.

"Good morning Jo. Did you sleep alright?"

"I slept better this time than I did back at your house Frank, if that's what you're asking." My feelings were still a little raw and bitterness coated my words. Frank just shook his head and went back to eating breakfast.

"Jo, while you're in the shower, I'll lay out your ski outfit for you."

"Why? Do you think I'm incapable of dressing myself," I snapped.

"Dammit Jo. Just chill for a minute. All this hostility is going to make this week really rough and it doesn't have to be that way." Frank sounded exasperated.

"Alright, alright. I'm sorry." I said. "I just want to go get cleaned up."

"Fine, but don't take too long. Tom should be ready in a few minutes too, and I'm eager to hit the slopes." Frank looked like he was done, but there was one more thing he wanted to say... "By the way Jo. One last request."

"What's that Frank."

"Shave."

"What? Why?" I asked.

"Well, for two reasons," Frank responded. "The less important reason is that I want you to." He paused for a moment. "The more important reason is that if you're going to be out wearing women's clothes, do you really want a lot of people looking at you?"

That caused me to pause because up until that moment, I hadn't considered that Frank and Tom might actually make me leave the house en femme. 

"Frank, you're not seriously going to make me go outside dressed like a woman are you?" I started to feel panicked.

"Yes Jo, I am. But I still want you to be comfortable." He said. "I figure that if you shave...everything...then maybe, with a little make-up, you could pass for a woman. I mean, you won't be able to stand up to any in-depth scrutiny, but hopefully, it will be just enough to minimize the stares that I know you're worried about getting. Just trust me."

And with that, I was face-to-face with a stark realization. Frank and Tom wanted their 'ski bunny' and I was it. And if they wanted to go out on the town, they planned to drag me along. If I didn't want to be further embarrassed, I needed to get with the program. I started to shake.

"Frank, please don't make me do this. Don't make me go out like a woman. Just give me my ski clothes so I can be a man for the day and when we get back, I promise, my attitude will change. I'll be more feminine in the cabin. I give you my word. Just don't make me go out dressed." I begged with fear and nervousness tinging my voice.

"It's too late Jo," he said and I cringed. "I'm not doing this to be cruel. Honestly, it's just that the only clothes we brought for you are women's clothes, so you don't really have much choice as to what you're going to wear. Where you do have some control is in how people respond to you. I can guarantee you that wearing the outfits we brought will generate stares if you've got facial hair. Take the hair off and you'll get away with a lot more. Plus, I've got another special item for you that should also make it easier."

"God Frank. Do you hate me? Is that why you're torturing me like this?"

"No, it's not that at all. Tom and I just have specific things that we like and want. This time around, we hadn't planned on things taking the turn that they did, but now that we're here, we both intend to make the most of it. If you could stop being so pissed off at us, you'd see that our behaviors towards you are limited in their context. Once the bet is over, we'll treat you like the man you are. But until, we're treating you like our girl. And we want to make that easy for you, but you keep fighting us every step of the way. Now I don't mind a little bit of a challenge, and a little fight from you keeps it interesting and fun. However, once we step foot outside that door, Tom and I will only be able to do so much for you. You're the one that's going to control how others perceive you. If you want them to see you as a man en femme, then that's what they'll see. If you want to make them second-guess what they're seeing, then do what you've gotta do. The second option will be less embarrassing for you, I guarantee it. But if you want to fight us, go ahead. You'll be bringing the external humiliation on yourself, then you'll have to deal with the consequences once we get back and are behind closed doors." Frank stopped his diatribe and stared at me. "Jo, I've told you what I wanted. I've given you options when I chose to, but now, we're entering a situation that is beyond my control. It's your turn to make the decision. What are you going to do?"

Tom had, without my knowing, stepped out into the hallway and he echoed Frank's question, "what are you going to do Jo?"

Reluctantly, I nodded my head and turned back towards the bathroom. "Okay," I responded meekly. "I'll shave. I'll do whatever I have to in order to blend in as much as possible in public." And with a tear in my eye, I closed the bathroom door knowing that I had just made a major decision to do whatever I had to in order to survive. It wasn't physical survival that I felt threatened with. It was my emotional well-being that I had to look out for. I figured that following the commands from Frank and Tom would be easier to cope with than the potential public ridicule I would face if I continued to be stubborn and obstinate. I wasn't happy with my decision because I felt like a piece of "me" was slipping away, but I hoped that in the long run things would be easier if I did things their way. 

So, with my fingers crossed and a wish on my lips, I began getting cleaned up. I shaved my face, my body, my legs, even my groin. I showered, patted myself dry, then started putting on what was to be my public persona for the next few days. I slid on another pair of cotton panties, some hi-cut bikinis, and a matching camisole. 

"Jo," I heard Tom call through the door. "We left your clothes on your bed. Get a move on or else we're gonna get a bad parking spot and miss out on the best runs of the morning."

"Okay, I'm coming." I stepped out the bathroom and made my way across the hall to my room.

"Let us know when you're done getting dressed," Frank said. "Don't forget, we've got at least one more item that ought to help. Oh, and don't worry about any tampons or other anal gear. At least not for today. Unless you need them or want them...?"

"No, no. I'm okay. I'll be dressed in a few minutes," I responded.

As I shut my door, I looked at the clothes they had laid out. Since it was cold, they'd left me some silk thermals and sport socks to wear, but it was the ski outfit that did me in. They'd gotten me a baby blue turtleneck, a black fleece vest, a pink and blue ski coat, and some black stretch pants with a decisively feminine fit. I knew that anybody who saw me wearing those clothes would think I was a girl, so I was semi-glad that I'd gone along with Frank's suggestion to shave. After sliding into all the clothes but the jacket, I turned to the dresser. There, they'd left an array of make-up with a note that said "use only what you want...but lip gloss is required." As a show of defiance, I only put on the lip gloss. It was like winning a small victory.

I grabbed my coat and headed out the room to meet the guys.

"Jo, like we said, we've got one more thing for you. Sit down please," was Tom's request. "This will hopefully make it a little easier to feel feminine and it should pass casual inspections." Then I felt Frank placing something onto my head. It was a wig. I knew that the minute I felt the strands brush the side of my face. Frank tugged it, and shifted it a little until Tom gave him the ok. "Have a look," said Tom as he moved from in front of a mirror. 

And there I was. A softer face, made so by the black wig that framed my face, falling to just below my shoulders, and lip gloss giving my lips kind of a wet look. I wasn't perfect. Anyone looking closely would be able to tell that I was a guy, but for the first time that morning, I felt like I had a chance of making it through the day without broadcasting my (remaining?) masculinity.

"We added some adhesive to the wig that will definitely keep it from falling off," Frank said. "You can put it in a ponytail if you want, or even get it styled later on...if you want. But it won't come off until we add some of the solvent that came with it. So feel secure that you're not going to be flying down the mountain and then see your hair go in the opposite direction." He smiled.

I offered a small smile of thanks back to both of them.

"Now, are we ready to go? Jo, got your tennis shoes?" I nodded.

"Okay then. Let's hit the slopes."

"Oh yeah...Jo, one more thing to remember," Tom added. 

"What's that?"

"Well, we know you can keep a few small items in your pockets, so here's some lip gloss, a tampon if you need it," Tom smirked as he said that, "some money, and your cell phone. Last thing. Don't forget to use the LADIES room if you have to go to the bathroom."

"And for Pete's sake, sit down while you're in there," Frank added through a sudden fit of laughter.

My blush would have been visible if not for my brown skin.

"Off we go."

And off we went. We got to the slopes and, while we had missed a chance to lay "first tracks," we still got to do some great skiing. The guys were gentlemanly in their behavior towards me all day. They joked with me, teased me, and flirted with me as though I was a real girl. It was a little unnerving at the beginning because I was so worried that I'd be "read." Of course, it probably was a little easier since I had on ski clothes, which are generally a little bulky, hiding me. Still, once we got going, things were okay. I actually forgot about my appearance while we were actually skiing. Once we stopped for lunch though, I was reminded of my current state because I had to go to the bathroom. And that was the one time during the day that the guys subtly reminded me of my current position. When I made my intentions known, Frank leaned in and whispered, "remember...it's the door with the girl on it." Then he sat back with Tom and laughed. I quickly hustled off to take care of business, remembering to sit down while I was in the stall, and even going so far as to touch up my lip gloss as I was at the sink. I quickly made my way back to the guys who were still sitting at the table, enjoying what was left of lunch.

"Ready to go?" Tom asked as I got back to the table. I nodded. We gathered up our things and made our way back out for the afternoon runs. It felt really good to be floating down the mountain, twisting and turning and enjoying the challenge. But after about 2-3 hours, we were all ready to call it quits. We knew it was time to go when Tom got to the bottom of the hill and, in trying to show off, came to a stop, then promptly flipped over when his skis stuck in the slush at the bottom of the hill. We all laughed and got our gear together as we headed back to the truck.

"Jeez, I'm sore," I said as we climbed into the truck. "It's been a long time since I've had that type of workout."

"Really," said Frank. "What about last night?"

"That was different and that resulted in a different type of localized soreness. This, this is an all over type of soreness."

"Tell you what Jo, since you've been such a good sport today and it looked like you actually enjoyed yourself, how about I give you a massage after dinner?" I looked shocked and surprised at Frank's offer. But being naturally suspicious, I had to ask "what's the catch?"

"No catch," Frank responded. "Just trying to be nice. I'm not saying that there won't be 'extracurricular activities,' I'm just trying to help you take some of the edge off."

I looked at Tom for confirmation.

"Jo, you should do it. It doesn't all have to be forced. We told you that we wanted you to have a good time too, so let us hook you up. Once we get back to the cabin, take a bath, read a book. We'll have dinner, then for tonight, I'll make myself scarce. You two can have fun and do whatever. I'll rejoin the activities tomorrow. Does that sound any better?" Tom asked.

I was skeptical but figured I might as well take the shot, if for no other reason than to see if they were being sincere, or if they were just trying to sucker me in for something else.

"Okay Frank. After dinner, I'll take you up on your offer." I was still a little nervous about getting a massage from a guy that I knew, but I figured he'd already fucked me, so it's not like I had to worry about him making a pass. That was guaranteed. But it was still different, because before, I hadn't been in control. I had been forced to submit. Now, I was giving myself over to Frank willingly and that was my struggle. That was the thought on my mind as I fell asleep for the rest of the ride back to the cabin.

"Jo, wake up Jo. We're back," Tom said.

I had no idea that I'd been that tired. "Oh, okay. Thanks." I almost fell out of the truck while trying to gather my things together.

"Hey, try not to drown while you're in the bath, okay?" Frank laughed as he noticed my struggles. "Here, let me take the skis and poles." I was again surprised by his behavior because it was just so different from anything I'd seen or experienced before. I decided not to look a gift horse in the mouth and let him carry my equipment into the house while I headed straight for the bathroom to start the bath, then to my room to change. As I went into the bathroom for the bath, I heard the guys watching TV and planning dinner, so I figured I'd be undisturbed for awhile. As I started to lower myself in the tub, I remembered the wig and quickly found one of the scrunchies they'd provided me with and tried to put up my hair the way I'd seen past girlfriends do it. It wasn't perfect, but at least my new hair didn't get wet.

I must have lounged in the tub for almost an hour, just soaking the stresses of the day away. Finally, when my stomach reminded me that it needed attention too, I got out of the tub and dried off. As I made my way across the hallway I heard Frank call out "I left two outfits on your bed for you to wear tonight. Your choice." Then he went back to watching TV. As I entered my room, there on the bed were my options. One was a black sheer teddy with an open back. The other was a sheer black chemise with matching thong panties. I was intrigued by both of them, but decided to go with the teddy. Slowly, I pulled it on, first sliding my legs in, then tugging it close against my body, tucking my penis beneath me, before finally attaching the halter straps behind my neck. It was a unique type of feeling, being wrapped in the teddy as I was. I decided to keep Frank guessing by grabbing one of the sweaters that he'd bought for me on the way and pulling that on. I also grabbed a denim skirts and quickly slid that on with a pair of pumps before sauntering out for dinner. As Frank looked up with a question in his eyes, I ignored him and sat down at the table while waiting for Tom to bring the food.

"Well, that wasn't quite what I bargained for," said Frank.

"True," Tom added, "but you didn't specify in the note that she couldn't wear something on top of the outfits that you selected."

"Well, I guess I'll just have to be more specific next time," Frank responded with a smile. 

As we ate, we talked about the runs we enjoyed during the day and we made plans for the rest of the week. We decided to take the next day off, then ski at a different resort for the following days. But as for tomorrow, the guys wanted to take me to the casinos for a little gambling and a show. 

"I'll go to the show, but I'm not gambling. Don't think I've forgotten that that's what got me in this mess...or position to begin with. No thank you. No gambling for me." They both laughed.

"That's fine. You can be my arm candy," said Tom.

"Well, you two have fun tomorrow. I think I'm going to gamble for awhile, but maybe I'll hook up with you for the show. But as for tonight, I think I'm ready to flex my muscles a little bit."

"That's my cue. You kids be good now." And with a wink and a nod, Tom excused himself from the table, put his dishes in the sink, then retired to his room to watch movies or sleep. 

"So..." Frank looked me up and down. "Where would you like to receive your massage? Your room or mine?"

"So many decisions," I joked. "What am I to do?"

"Pick one, before the decision is made for you." Frank was about to take control again. "I'm going to clear the table. When I'm done, I'm going to find you wherever you are, then I'll give you a massage and we'll see how things go from there." He got up and started stacking dishes. I waited until he had ventured further into the kitchen before sliding my chair out and making my way down the hall. I was still mentally adjusting to the role that I had so willingly taken on during the day, but I swallowed my nervousness and made my way into Frank's room. As I stood in the doorway, I heard footsteps behind me.

"Go ahead."

I turned to face Frank. I looked him in the face and let him see my confusion and distress.

"Don't worry about anything. What happens here stays here." With that, he gently grabbed my waist and guided me further into the room. "Before we go any further, I want to see what you're wearing. Just take off the sweater and skirt. Keep the shoes on." Then he stepped back and waited for me to strip. Slowly I shimmied out of the skirt, letting it fall to my feet. As I started pulling the sweater up over my head, I heard him say in a soft voice "very nice." I stood there before him, dressed only in a teddy and pumps, with my hair hanging across my shoulders and my hands crossed in front of me.

"Lie face down on the bed."

I moved around the side of the bed and crawled onto it. I put my face on the pillow and tucked my hands underneath the pillow so he wouldn't see them shaking. I heard him taking off his clothes. By the time he got close, he was wearing only his boxers. Then I heard him turn on some soft music. He didn't sound like he was close by so I opened my eyes to peek at where he was. I saw him lighting candles around the room and I thought to myself "is he trying to set up a seduction." I didn't say a word. I just lay there and closed my eyes waiting for him to make the next move. I felt him looking me up and down, soaking the image of me in and burning it in his memory. I closed my eyes and waited for him to make the next move. I smelled it before I felt it. It was the scent of perfume. Then, I felt lotion being spread on my back. I felt Frank's hands kneading the muscles in my back, pushing all soreness and stress away. He started up towards my shoulders and worked a knot that had been there all day. "Relax" was all he had to say. Then he continued with the massage. He spent a few more minutes working on my shoulders and arms, then started working his way down my back again. I felt him spread more lotion on my lower back as he neared my hips and ass. He massaged my lower back and ass and only flirted with my asshole. I felt his fingers dip into the crack of my ass and just lightly probe my hole before he continued past it and started working on my legs. Slowly and methodically, Frank worked the muscles of my legs and involuntarily, I felt a moan escape my lips. I blamed it on the skiing we had done earlier and appreciated the relief his hands provided. Minute after minute, he worked on my legs moving with tender care further and further down until he reached my feet. I was surprised when he started taking my shoes off. I started to say something, but Frank stopped me. "I'm going to put them back on in a minute. I just wanted to massage them too, and put some lotion on them." I didn't say another word. I was still somewhat dazed by Frank's outpouring of gentleness and caring, and I was relishing the sensitivity with which he treated me. His massage nearly put me to sleep, but I suppose it was my curiosity at where he would take things next that kept me awake. Still, I could see how people got addicted to receiving massages.




A Lost Bet Ch. 03



"Roll over," he said. Slowly, I rolled over onto my back, feeling relaxed and sensual. It was a very different experience than the other times that I had been used by Frank. "Keep your eyes closed," he said. I felt him start to rub the front side of my legs with lotion and I couldn't believe that the massage was continuing. I started to peek at the clock when I heard him say "you're stubborn to the end aren't you?" But there was no malice or harshness in his tone. Not even the commanding nature that had characterized our other encounters. "I guess there are some things that we just won't be able to change," he said as he reached up and softly closed my eyes for me. "Since you seem to want to peek, against my requests, I'm going to blindfold you. After I do that, please, just try to relax...for me." I didn't say anything, but I did raise my head so he could slide the blindfold over my eyes.

"Now, back to the massage." And he started up right where he'd left off...rubbing the front part of my legs and working his way up to my thighs. As he got closer and closer to my groin, I felt myself start to harden, even while tucked away in the teddy. 

The next touch surprised me. Frank started to spread my legs and he pulled my penis loose. His lotioned hand started to stroke it slowly, gliding up and down, until he decided to tuck it in the front part of my teddy, trapping it against my stomach. I was in shock because in our past two encounters, Frank had never really acknowledged that I even had a penis, let alone touch it. Tom had been the one to put it in captivity the other night. So for Frank to touch it at all left me shaken and quivering with a desire for release that had long been denied to me.

Frank continued to massage my front...my thighs...my hips...my stomach...then he reached my chest. I wished I could see what he was doing but the blindfold made it impossible. I could only wait for the next touch, imagining where it would be. Then, it came. The soft touch on my nipples and my pecs/breasts. Frank started to massage them slowly, rubbing them all over then teasing the nipples through the teddy. He pinched them, but not to cause pain. But with each pinch, I still gasped and I felt my body arch as he pulled on them lightly. I'd never known a feeling like this. I almost wished he would continue...until I felt his hot breath on my right nipple as he started to lick it through the teddy. He licked it, then sucked it and I moaned. I felt myself starting to squirm with a pleasure that had been denied to me before. I thought to myself "my God...if this is what girls feel when guys are kissing on them, it's no wonder they like it..." I had no time to pause and consider the changes in my thought process because Frank moved to my left nipple and started the process all over again. I lay there, soaking in the experience, feeling myself moving closer to a precipice I never thought I'd reach with a man...a point that I'd never considered reaching with a man because I wasn't gay (was I?). I knew that I was moving towards a climax, but wasn't there yet. I was somewhat ashamed to be this aroused under the ministrations of another man, but I didn't want it to stop. 

Frank pulled himself away and I heard myself utter a moan of a disappointment. I couldn't believe that the sound came from me, but a part of me didn't care. I found that I was enjoying the experience of being on the other side of things. I wasn't the aggressor. I wasn't expected to be in control. I knew that I was still a participant, but for the first time, I started to really feel out of control...in a good way. 

"If you're enjoying yourself more than you thought you would, nod." I nodded. Slowly, but with no hesitation. "Good," he said. "Finally, you're coming around to the possibilities of what could be...at least in this time and place." 

I felt his weight come back on the bed, but I could feel him at the foot of the bed. As he moved up the bed, he spread my legs wide and situated himself on top of me. He didn't rest his weight on me though. I could tell he was using his arms to support himself as I felt his breath on my neck. Then, a nibble on the right...a nibble on the left...a little tongue in my left ear...a gentle kiss on my forehead...a light tonguing of my right ear. My breath was coming in sporadically and raggedly. I could feel his dick pressed against my balls while my dick strained against the teddy. I could feel his stomach pressed against mine. I reached out and felt his arms taut, supporting his body. Then...I felt his kiss on my lips. Lightly he kissed them. His tongue caressed my lips and parted them. I responded to his kiss as though I had no control over my own body. Deeper and deeper he kissed me and I felt myself rising to meet him. I wished I could see, but I settled for feeling as I wrapped my arms around his back. 

We continued kissing and rubbing our bodies against each other for a few more minutes before I felt Frank pull away again.

"Roll over, but stay lying down on your stomach."

I rolled, then waited for the next sensation. Again, I felt Frank spread my legs and position himself between them. I felt his hands on my ass, spreading my cheeks apart so he could find my hole. As he started to tease my hole with his fingers, I felt the coolness of the lotion dripping in. I tried to relax as he slid his fingers in...first one...then two...then three...I squirmed and he used his other hand to put pressure on my lower back, keeping me in place. I started to breathe ragged little breaths as he finger-fucked me for a few minutes, but I was mildly surprised as his slid his fourth finger into my ass. I gasped and tried not to move while I got accustomed to this sensation. This was so different from the invasion I had experienced from the vibrator on the machine, or the beads, or even from the cocks of Frank and Tom. This was a little more tender...a little less pressured...and a little more unpredictable. That last thought hit as he started moving his fingers around in my ass, causing me to sharply inhale right before a little moan escaped my lips. 

"Are you ready?" he asked.

"Ready for what?" I replied. Only I didn't get all of my answer out because right in the middle, Frank started forcing his entire hand into my ass. "Wait...wait...wait..." was all I could manage to get out. Even though he was going slow, the pressure was amazing and I had never been stretched quite like that. "Oh God...it's too much..." I moaned into the pillows. But Frank didn't stop. He pushed, added lotion, then pushed some more until his entire hand was up my ass. I didn't move. I just lay there reveling in the mix of pleasure and pain praying that he wouldn't move...because then I'd have to readjust. 

"I'm pulling out now." And he did just that. Slowly, gently, he removed his hand from my ass and I was left shuddering on the bed trying to get my mind around the fact that I had just had another man's hand ENTIRELY up my ass. I wasn't able to ponder the thought long though, because Frank moved on top of me and gently eased himself into me. 

This was different. I wasn't bound. I wasn't being handled by two guys at once. It was one man on top of me, slowly, almost lovingly, fucking my ass. For the first time, I didn't feel like I was being assaulted...I felt...sensual. Feeling his weight on my back with his dick in my ass, I wanted to move against him. Even as he fucked me, his hands caressed my arms and pulled them above my head where he intertwined his fingers with mine. His fucking was slow and luxurious and it forced me to grind my own dick into the bed. With each of his thrusts, my cock was caressed by the mattress and teddy giving me my own special pleasure. Thrust after thrust from Frank and my pleasure built.

"Oooh Frank," I moaned. "I think I'm gonna cum." 

"That's good Jo...that's good...I'm not far behind you."

Frank started pumping faster and his pressure on my prostate combined with the sensations from rubbing against the teddy made me feel like I was going to burst. 

"Please...Frank...please...quick...can't hold on..." My statements were jagged. My breath was ragged. My body was starting to shake from the exertion and the pleasure. I felt muscle twitches all over my body and second after prolonged second, I tried to hold on until I could go no further. "Mmm...ooo...uunnhh...mmmm...!!" was all I could sputter as I came all over my stomach. Then Frank started grunting...harder and harder...and his pounding reached a new level until finally...he came with a bed-shaking, toe-curling orgasm. My mouth was open in a silent "O" as I tried to breathe under the pressure. My hips bucked as Frank spurted jet after jet of cum into my ass. After he was done, we lay there for minute after minute, trying to breathe and recover our spent energies.

Finally he spoke. "So...was it good for you?"

I laughed. I didn't mean to. I never thought I would. But I did. I giggled and said "yes."

"See what can happen when you just relax?" I could hear the smile on his face as he spoke. Slowly, he let go of my hand and began to trace the outline of my body with his finger. I shivered at his touch, but I longed for more.

"Jo, that was the way things should have been. Maybe if we'd started there, you wouldn't have been so resistant all along."

"No. I disagree." I stated. "I never wanted any of this to happen. At least not on a conscious level. Now that it did, I'm still not entirely sure how I feel about it."

"Oh really?" teased Frank as he ran his hand over my nipples and then down to my softening cock which twitched involuntarily in his hand.

"Yes Frank. Really. I'm not going to lie to you though, and say that I didn't enjoy what just happened. I mean, that was amazing...and surprising...and sensual...and scary...and enjoyable. And I guess that while we're here on this trip, I'll go along with some of your games and plans. But once we get back, I want my life back. I want my manhood back."

"Okay Jo. I can respect that," said Frank as he continued to caress my body. "Let's deal with the real world once we're back in it though. Is that a deal? Can we just enjoy the moment and let tonight be tonight and this trip be what it is?"

"I suppose so," I mumbled through a yawn. "Damn, I'm tired."

"I know. I've got skills," Frank laughed.

"Oh, don't try to get a big head about things. You forget, I was already tired from skiing."

"Potato, po-tah-to." Frank continued to laugh lightly as he nuzzled my neck. "Go to sleep, but don't be surprised if you get woken up later on."

"I won't. I know you well enough to know that I need to expect the unexpected." Then I turned my head, pushed myself back into Frank's embrace and passed out dreaming of what the next day would bring.

To be continued... 



A Lost Bet Ch. 04



As I slept that night, I dreamt vivid dreams...sexual dreams. The next morning, I was able to remember one of the dreams that I had but I didn't tell Frank or Tom. I kept it to myself because I wanted to understand what it meant. I'd dreamt that I was walking down the street when I got close to the entrance of a park. It was me in my male clothes. As I got closer to the entrance I heard a voice behind me. I couldn't understand what it was saying but as I turned to look, I saw someone start to run after me. 

As I started to run forward, I saw another figure start running towards me from in front of me. In order to get away, I turned into the park to try and get away. As I ran, the hedges started to grow taller and taller until they stretched far above my head. They were too thick to run through, so I twisted and turned along the path trying to get away. I ran full speed, missing some corners and crashing into hedges as I tried to escape from the voices of my pursuers. With each crash, my clothing became torn, and as some parts of what I figured was a maze got narrower, or were overgrown, I found myself losing some of my clothes entirely. 

Finally, I entered the center of the maze but I felt a breeze all over my body. I looked down and realized that I was completely naked. I'd even managed to lose my shoes in the process of running away. I staggered towards what I believed to be a bench to catch my breath, but when I sat down, I fell straight through. It was as though the rabbit hole from Alice in Wonderland had swallowed me up. I slid down the hole faster and faster until I fell out onto a pile of pillows. I looked up, dazed and confused, but as I gathered my bearings I saw I was in a bedroom. I stumbled to my feet and looked around and there on the bed was a set of clothes that I could put on. The closer I got to the bed, the more the clothes looked like the very ones that Alice had worn in the story. I picked up the clothes and heard voices from outside the room...some in the hallway, others echoing down the tunnel through which I'd just fallen. I started rushing to get dressed in order to be able to make a partially decent escape...but I saw no door. Then, in the corner I saw nothing but a smile...the hallmark of the Cheshire Cat. "Now," he told me "it's time to find out just where the rabbit hole goes."

I started awake. "Jo, baby...you okay?" Frank roused from his slumber and reached for me. I was sitting up, breathing hard from the experience of the dream.

"It was nothing. Just a dream."

"Okay. If you say so." He rolled over to look at the clock. "It's about time to get up anyway. I must have been more tired than I thought."

As I gathered the covers around me, I felt fresh cum leaking from my ass. Frank saw me squirm and said "I guess we must have gone another couple of rounds in our sleep." He winked at me and made his way to the shower. While he was in the bathroom, I lay there contemplating my dream and figuring that the only meaning was that I was willingly ready to explore further dressing as a woman and whatever came with it. I had feelings of anxiousness and nervousness as I adapted to my new role, but I asked myself "how bad could it be? Last night wasn't that bad. It was actually kind of nice." I smiled as I thought about Frank's seduction of me. It really had been an interesting experience.

With those thoughts and feelings in mind, I made my way out of his bed and back towards my room.

"Hey Jo," Tom called out from the living room. "You guys sounded like you were having a REALLY good time last night." He laughed. "Well, today, you're with me. I laid out the outfit I want you to wear. I was going to wait for you, but it started getting so late that I figured you wouldn't mind."

"No problem Tom. Let me get cleaned up, get something to eat, then you can tell me what you've got planned."

I turned into my room and started to gather up what I needed for the bathroom. I saw the outfit Tom had laid out for me. It was a black leather miniskirt with matching jacket, royal blue corset with matching thong panties, black thigh-hi stockings, and knee hi boots with a stiletto heel.

"Tom," I asked, "where exactly are we going today?"

"Well, you're going to be my arm candy while I do some gambling. It always helps to have a sexy lady on your arm when you're at the tables."

"Okay." I didn't say anything else. I simply went into the bathroom and started getting cleaned up. After a few minutes, I heard Tom and Frank's muffled voices through the door...

"Frank, whatever you did last night really mellowed Jo out. What did you do?"

"Nothing big. Just treated Jo like the lady we knew he could be. I think she'll be much easier to handle throughout the rest of the week."

"Cool. Hey, check out this show that's taking place at the casino tonight. You think we should go?"

I didn't hear anything for a minute, then finally Frank responded "oh definitely. That party will be worth the trip. I'll tell you what. You guys enjoy your day, then I'll meet you at the casino around 5 this afternoon, a little before the show."

I was curious as to what party they were talking about, but I didn't have time to worry about it since I needed to get dressed. With that, I jumped in the shower and started my routine of showering, shaving, and putting on some light makeup. After I finished up in the bathroom, I went back to my bedroom to finish getting dressed. Once I was done, I stepped out into the hallway.

"Tom, do I look alright?"

"Jo, you look fantastic." Tom was looking rather dapper in a pair of slacks, a short-sleeved sweater, with his leather coat draped over his arm. 

"Are you sure we'll be warm enough? I mean, we're surrounded by snow?"

"Don't worry. Once you get into the car, you'll be fine. The casinos will be warm enough and we'll be there for the afternoon. Frank will meet us there for dinner and a show later on this evening." Frank then tossed me something. "Last thing Jo. Put this in."

I caught it and looked at it. It was a large butt plug. "Umm. I don't know if this is going to fit."

"Come here," commanded Tom. Slowly, I walked towards him. As I reached him, he put his coat on the chair then told me to "bend over." I leaned over the table with my ass in the air as Tom started lubing up the plug. He pulled my thong to the side, then slowly and gently started filling my ass with the butt plug. I moaned as he pushed it in. Finally, when it was all in, I noticed that my breathing was a little ragged. "Don't worry Jo. You'll get used to it. I just wanted you to wear it because it will give you a little more sway to your walk." As I stood up, I felt incredibly full. And as I walked towards the door, I noticed my hips swaying a little bit more as I tried to accommodate the plug in my ass.

Tom opened the door for me, and as I sat down in the truck, I really felt the pressure from the plug. I squirmed. "You doing okay over there?" Tom asked as he slid in the driver's side. "Yeah, just adjusting. Don't go over any bumps, okay?" I joked. Tom laughed and pulled off. We engaged in small talk all the way to the casino. He asked what happened last night and I gave him a brief description of the massage.

"How did you feel?"

"I guess I enjoyed it. I still feel a little funny, but last night was probably the most relaxing time that I've had with you guys so far."

"Well, that's good to hear. Hopefully you'll enjoy today too."

Once we got to the casino, we parked in the underground garage. "What are you going to do first?" I asked.

"I figure we'll start with roulette, then maybe play some blackjack. We'll see how things go from there. But first," Tom said as he started to unzip his pants, "how about a little blowjob to take the edge off?"

"Tom, somebody might see." I started to panic and backed up against the door as my eyes darted from side to side.

"No, they won't. Trust me, nobody's looking for anything down here. And even if they do see, it's not like they haven't seen it before." 

"What happened to not making me do anything out in public?" I asked, imploring him with my eyes to forego the blowjob.

"This...this is not public. I could have asked you to follow me into a restroom in the casino. I could still try to fuck you in the elevator. I could take you outside, find an alley in the cold snow and make you give me a blowjob there. I am ASKING you for one here in the privacy of my ride. I'm only going to ask the question one more time: Jo, please give me a blowjob before we go into the casino." Tom looked serious, but I didn't think he would hurt me if I refused.

"I...I can't. I'm too nervous. I'm sorry," I said as I put my head down and looked away. "Please don't be mad at me. It's just that...the cabin was one thing. This is another. I'm having a hard enough time knowing that I'm about to be in a public place dressed as a woman with a huge butt plug up my ass. Don't you think that's enough for me to have to do?"

"You're right Jo. No problem." And he zipped up his pants. "Let's go." He didn't look happy, but he didn't look pissed either. I really couldn't get a good read on what he was feeling.

"I'm sorry Tom. Look, I promise I'll make it up to you once we get back to the cabin. I promise," and I smiled at him, my eyes begging for forgiveness.

"Come on Jo," Tom said as he opened the door. "Don't even worry about later. For now, just be a sexy lady on my arm." He offered his arm to me as he walked me through the garage and into the elevator. He didn't say much to me as we walked but I tried to dismiss it and focus only on being as feminine as possible. I figured that the less I talked, the less likely I was to be read as a man.

I was so focused that I missed Tom's comments.

"Jo...Jo...listen to me. I was going to let you off the hook, but I think you should know that your refusal in the garage will have repercussions later on."

"Like what?" I asked hesitantly.

"I'll start with this," Tom said as he reached into his pocket. All of a sudden, I felt intense pressure in my ass as the butt plug started vibrating and pulsing.

"Oh...n-n-n-no...turn it off...please turn it off..." I stuttered and stammered as I tried to maintain my composure. "It's too intense."

"If you'd only done like I asked, you could have just enjoyed the plug," said Tom. "Since you still had to resist, you left me no choice. Well, that's not really true. I'm going to enjoy watching you squirm for the rest of the day, and that's a choice that...doesn't really bother me at all. You?" He smirked as he waited for my response. I was speechless as I rode the sensations and tried to stay ladylike. "Good. Glad to see you're not bothered. And you will make it up to me later. I guarantee it."

We walked to the main casino floor. Or perhaps Tom walked while I stumbled along beside him trying not to fall over due to the random sensations sent through my nether regions. Over the next few hours, we stopped at the blackjack tables, roulette tables, craps tables, and finally, the poker tables. Tom only let me sit down at the blackjack and poker tables. Honestly, I wasn't sure whether I was better off sitting or standing, because when I sat down, the plug got shoved further up my rear where it continued to twitch and vibrate and put pressure on my prostate. But when I was standing, I felt like me knees were going to buckle. There was no escaping its' relentless assault on my ass. I was only minimally aware of the occasional soft moan escaping my lips, but Tom paid me no mind. It was some of the looks that I got from others nearby that let me know that I'd actually made a sound. I saw some of the quizzical looks on their faces, but tried to ignore them, and they ignored me as they focused on their gambling. But I know that every now and again, while Tom and I were at the roulette and craps tables and the crowds were pressed together, I felt a hand pinch my ass. I knew it wasn't Tom because I could see both of his, but I couldn't turn around to see who might have done it. It didn't matter anyway, because I would soon be focusing on the vibrating butt plug again, alternately praying that the batteries would die so I could get a break and hoping it would continue so that I could cum. Neither one happened.

A few years later (okay, actually just a few hours later), we met up with Frank in the lobby of the casino.

"How'd you guys do?" Frank asked.

"I'm up about $700, so I'm pretty happy," said Tom. "Jo is feeling something else for an entirely different reason."

"Oh no. You didn't have to use it on her, did you Tom?" Frank asked as he shook his head.

"Yep. She refused a simple request when we got here, and I had to remind her that even minor innocuous requests should not be refused." Tom look disappointed as he continued on to say, "I thought that after last night with you, she'd be easier to work with, but since that doesn't seem to be the case, I guess we're running out of options."

"What...what are you guys talking about?" I stammered through my sensual onslaught.

Frank and Tom both looked at me, then each one took an arm and they led me to a hallway leading towards the ballrooms. They said nothing while we walked and I continued to look from one to the other for a response. Once we were in front of one the ballroom doors, they stopped.

"Jo," Frank said. "We're about to go into a different kind of show. The show is called Erotique, and there's a few things you ought to know. First of all, we'll probably be a few of only a small group of Black folks in the show. So that's going to draw attention to you regardless of anything else. Secondly, had you only obeyed, we might have let you enjoy the show in a different capacity. But since you continue to be stubborn, even after we had such a great night last night, then you're going to have to learn a few things. One is how to obey. The second is how to give pleasure on a moment's notice. The third is to surrender. I hate to say it, but in this show, the more you fight, the harder your life is going to be. I know I said back at the cabin that I don't mind a little fight because I like the challenge. But here, and know that I'm telling you this because I like you, fighting back, resisting is bad. Like on Star Trek, with the Borg... 'resistance is futile.'" Then he nodded at Tom who grabbed my wrists, turned me around and forced me to face the wall. As I started to stutter out a question, Frank produced a ball gag, seemingly from out nowhere and forced it into my mouth. "To keep the protests to a minimum," he said. I started having flashbacks to the first night the guys had their way with me and I started feeling nervous. I tried to squeeze a question out around the gag, but succeeded in making nothing more than a few mumbling sounds. Tom slid my jacket off my shoulders and arms, then tied my wrists together behind me.

"Are you ready Frank?"

"Yep. Let's go." Then Frank opened the door and guided me through the door in front of him. We took a couple of steps down a short hallway, then knocked on another door. A slat slid open and an eye looked us all up and down, then slowly pulled the larger door open. As we entered into the darkened room, my eyes started to adjust and I took in the scene around us. It was nothing like I'd ever seen before. Everywhere I looked, I saw people in bondage...people having sex...people being teased and tortured... I turned and looked at Frank and Tom with fear in my eyes because I knew what they were thinking. My eyes pleaded with them to walk us out of there. I pressed myself against Tom trying to coax forgiveness out of him by offering myself to him, but he just turned to Frank and said "I think our little Jo is feeling kind of frisky. Where should we start?" Either he'd misinterpreted my body signals, or he was just choosing to ignore my desire to escape. 

Frank took my arm and started leading me through the room towards a corner that seemed to have an array of spanking mechanisms. As we walked, I saw people turning to look at us making our way through the room. I looked around and was able to spot only one or two other Black faces and I knew that Frank's words were true. I was going to be an attraction.

When we arrived at the corner, Tom unzipped my skirt, pulling it to the floor and I heard a few whispers and giggles as the crowd noticed that, not only did I have a large, vibrating butt plug in my ass, but I was also a man. "Mmm... I'd like to get a piece of that ass," I heard someone say, but I had no idea who it was. More comments followed as Frank and Tom pulled me towards one of the devices. There was a woman standing there, and she almost looked like a saleswoman.

"I see you've got a 'bad girl' there. Does she need a proper spanking?" She asked with a twinkle in her eye. Her name tag said "Lisa," and she and the guys started to talk as if I wasn't even there.

"Lisa, our girl Jo just refuses to act right. We figured that we'll have her make the rounds of some of the activities here until she gets her attitude right. What can you tell us about what we've got here?" Frank asked her as he pointed at different set-ups.

"Well, we've got various hand-held spanking instruments that you're welcome to use, and buy if you'd like to take them home with you. We've got paddles, whips, rulers, breadboards, belts...and a couple of other things that I KNOW you'll enjoy. If you'd like to try some of them out, why don't you get...Jo, is it?...set up, or tied down over here." She pointed to what looked like a padded counter. Frank and Tom dragged me over to it as I tried to resist being moved over there. But there was nothing I could do. The pushed me over the padded edge of the counter and spread my feet apart. Tom secured my feet to each leg of the counter while Tom grabbed a chain that was hanging down and tied my wrists to it. It was a position I'd been in before, but this time I felt much more vulnerable. I could almost feel the tears start to form in my eyes.

"Don't cry yet Jo," said Tom. "We haven't even started yet."

Then Lisa noticed the butt plug. "Did you want to take out her plug, or leave it in?"

"Leave it," both Frank and Tom said in unison which drew a round of laughs from the gallery.

I continued to moan and struggle in my bonds but there was nothing I could do to free myself. As I looked ahead, I saw Lisa moving a mirror in front of me so I could see exactly what they were about to do to me. "Such a deserving girl. I'm sure that whatever you're about to receive, you had coming to you." Then she returned to Frank and Tom and discussed the merits of each spanking instrument.

I heard her say "the smaller instruments give a more focused sensation and tend to leave marks. See?" Then I jumped as she slapped my ass with a ruler. Again and again, harder and harder...she just kept spanking my ass and legs. "You've got to be careful though, because if you hit too hard with the smaller ones, the likelihood that you'll break the skin goes up. You want to try and find a balance. The larger tools, you want to be more careful for a different reason. While they do produce an overall stinging sensation in the spank-ee, you don't want to hit too hard. I've heard of people actually causing internal injuries from spanking someone too hard with one of the larger paddles or breadboards." She then proceeded to demonstrate what a good level of force could be. "Anything that strong or less should get you maximum reaction without feeling like you're not doing your girl too much damage. Here Tom, give it a try." I looked on in horror as Tom wound up and proceeded to paddle my ass. With each stroke, I squealed and moaned. After about 5 strokes, Tom backed away and Frank came from the other side with one of the breadboards. The larger paddles left my entire ass tingling and each stroke forced the butt plug further and further in. I was losing myself in the pain and humiliation.




A Lost Bet Ch. 04



"Now, I want to show you guys something really special," said Lisa. "Since you've already gotten her ass warmed up, I'm going to cool it down with a little ice before bringing out the next toy." A muffled yelped came out of through the ball gag as she ran a couple of ice cubes over my sensitive skin. When she took the ice away, my rear felt tingly...a cross between feeling numb and overly stimulated. I looked up into the mirror to see what she was doing and I heard the crowd mumble and "ooh" and "aah" and say "that's pretty cool" as she wheeled a device up behind me. All I could see was that it looked like a bicycle wheel mounted on its side.

Lisa started her spiel. "This is our newest spanking device. It's been affectionately named 'Sir Spanks-A-Lot." The crowd laughed. "What you see is a bicycle wheel mounted on a small electric motor with adjustable speeds. You can position the wheel horizontally or vertically or anywhere in-between thanks to the adjustable mount. On the wheel, you can mount up to 6 attachments that are included in with the machine. If you want to use the harder spanking tools, we recommend that you position the spank-ee in a way that allows the machine to move them as they are spanked. For now, we'll just use the leather straps. Once the straps are attached, you plug in the machine and then adjust the speed by turning this knob here. We're working on a wireless remote for the motor, and that model should be available in the next few months. Once you set the speed though, just relax and watch the machine do all the work of spanking and discipline for you." With that she turned the motor on low and I felt my ass being spanked anew. My yelps and moans were in time with the slaps from the leather straps.

"Do it faster," I heard a few people in the crowd call out. "Faster...faster...faster." A chant had broken out as the crowd watched me get spanked by the machine.

"Okay. Now be aware that the faster the machine goes, the harder some of the lashes will be. We've got a built in governor to keep it from going fast enough and hard enough to break the skin." Lisa explained. "Do you all want to see the highest setting?" She called out. "Yeah!" responded the crowd.

"Is that all right with you gentleman?" Frank and Tom nodded. And Lisa turned the speed on the motor up to high.

"MMMHHHMMPPH!!!..." was all I could get out as the leather straps bombarded my cheeks. There was no more moaning with the beat. The licks came quick with no breaks to catch my breath. My ass was so sore and tender that each slap sent a spark through my body. I wanted the spanking to be over more than I'd wanted anything else in my life. Tears started to run down my cheeks and my sobs could be heard through the gag. Finally, Lisa turned off the machine and Frank came around in front of me.

"Jo, Jo...are you finally ready to stop resisting and do what's being asked of you?" He asked these words while cupping my face with his hand and slowly wiping some of the tears away.

I nodded.

"Do you promise to do whatever we ask you to do?"

I sniffed...and nodded.

"Let her up Tom." And Tom started untying my arms from the hanging chain.

"Lisa," Tom said, "make sure we have your card and a brochure because I know we'll want to order one of these."

"Oh, most definitely," Lisa responded with a million-dollar grin. "Thank you for helping out with the demonstration. I think that worked much better than just displaying the products."

And indeed it had, because the line of people touching and examining the machine was long. 

Frank helped me stand up after Tom finished releasing my feet, and he cradled me to his side while I shed the remaining tears. Tom came by and slowly ran his hands over my ass and I squirmed. Everything was so tender that the slightest touch felt like fire on my cheeks. The guys guided me away from that particular corner and headed over to a wall. There they removed the butt plug from my ass and I stood there shivering and shaking as I got used to the empty feeling. 

"Okay Jo. Are you ready for your first test?" 

I nodded. 

The guys led me to another corner where there was a huge array of dildos and vibrators. Some were hand-held, but others were attached to a board jutting from the wall just high enough that someone could get on their hands and knees and fuck themselves with it. I knew what they were going to ask me to do because I could see a woman on her knees fucking herself against the mounted dildo with another one in her ass. Her eyes were glossy as she reveled in the self-induced pleasure while a group of people looked on. She continued to fuck herself while a man came up to her and started teasing her breasts. She moaned in apparent ecstasy. Then, someone who had apparently been at the other booth watching my "demonstration" called out, "let's see the Black tranny fuck herself!"

Tom and Frank looked at me as I shrunk. But knowing I had no choice, I hung my head while they untied my hands from behind me and retied them in front of me. "Jo," said Tom, "you can pick the first dildo to use. But before you cum, you have to use 'the big one' and you have to use the one on the wall." I looked up to see what "the big one" was and nearly froze as I saw a dildo that must have been 5 inches in diameter and 11 inches long. I couldn't stop staring at it...whether it was out of fear or desire, I couldn't tell. I'd never had anything that big in my ass and I wasn't sure about trying it in front of a large group of people.

I started to shuffle forward to some of the dildos lying around, trying to see which ones looked manageable. Finally, I found one that was about 6 inches long, and about an inch in diameter. I picked it up, then looked at Tom and Frank for approval. They nodded that it was okay. I knelt down, then had to reach through my legs to insert the dildo into my ass. My hands felt delicate as I eased it in with a small whimper. Slowly, I started to fuck myself with it, moving it around until I found a spot where it actually started to feel good. For the first time since the night before with Frank, my ass felt good being invaded. I started to moan in pleasure and my hips started to writhe. My eyes were half-closed and I didn't see Tom approaching me. It wasn't until I felt his hands on my chest that I looked up. He'd gotten some weighted nipple clamps from somewhere and he put them on my nipples one at a time. I gasped at each pinch and started to squirm even more. As I continued fucking myself, Frank appeared and handed me a larger dildo. It had to have been about the same length, but it was wider, probably 2-3 inches around. I slid the first one out and slid the second one in. My moan was louder as the feelings were more intense this time. Still, I continued to enjoy the erotic feelings that were waking inside me. I started to surrender to the pleasure...feeling my ass full, my nipples taut, and my cheeks tingling. It was an extremely exotic and erotic moment. The minutes passed and I could tell people were still watching me because I could hear their comments, but I started not to care. I did, however, attend to Tom's voice when he said "use the one on the wall." I pulled out the dildo I had been fucking myself with and got on my hands and knees facing away from the dildo that was sticking, almost obscenely, out from the wall. Slowly, I eased myself back onto it, relishing the feeling of having my ass filled. I started to want it, and I moved faster. The change in positions brought different sensations, different feelings, and sent me to a new level. I rocked faster and faster. But the crowd wasn't satisfied.

"Give her 'the big one.'"

"We want to see her ride 'the big one.'"

I opened my eyes to look around and see what Tom and Frank wanted me to do. I hoped they would let me stay here because I was so close to cumming. But they didn't. They motioned to the large dildo on the rack and I crawled forward towards it, hearing a small pop as my friend on the wall exited my rear. 

"Jo, stop right there for a minute." I turned to see Frank heading towards me. I wondered what he was planning to do. "You're going to need both hands for that one," he said as he untied my wrists. Then, he surprised me by taking out the ball gag. "The crowd wants to hear your unadulterated pleasure." He stepped back and let me continue on my path towards climax. I reached the rack and took down 'the big one.' I positioned myself on my knees over the huge dildo and aimed it at my ass. I started to force myself down onto it, trying to hold it steady with both hands, but was only moderately successful. I tried again and again, until I was panting from the exertion and pressure. I'd never felt that stretched before and it was taking awhile to get comfortable.

"Frank...Tom...please help me." The words came out of my mouth before I could realize what was happening. They both smiled at me and came over. 

"Get on your hands and knees," Tom instructed. Frank took hold of the dildo and started to push it in while Tom dribbled more lubricant down my ass crack. Slowly, inch by inch, it went in. I was gasping and moaning and mewing, and the crowd was eating it up. Frank stayed behind me and started to fuck me with the dildo. My eyes closed. Then Tom started playing with my nipples and caressing my ass. I was in another world. This continued on for a couple of minutes and the crowd was appreciating the show. The last straw came when I felt Frank reach around me and grab my dick and start to caress it. My mouth opened as my breathing got ragged. He started stroking me in time with the pushes of the dildo. I think I started calling out "yes...more...please fuck me...don't stop..." but I'm not sure. My body was convulsing and my legs were shaking and I was so gone by that point that I didn't know what I was doing. 

Until finally...I came. I spurted jet after jet of cum onto the floor in front of me, getting the release that had eluded me all day. I collapsed onto the floor to rousing applause from the crowd. "Oh my God," I thought to myself as I started regaining control of my senses. "What did I just do? What just happened?"

I opened my eyes to see Frank and Tom standing there like proud parents. "That's our girl. We always knew you could do it." I continued to lie there trying to catch my breath. Other people that had been watching stopped to congratulate Tom and Frank on having such a wonderful girl to play with. I saw them exchange information with a few people and heard mumbled words about a private party at a cabin by the lake in a couple of days. But I wasn't focusing on much. My body was wired and I could feel everything. The stickiness of the cum underneath me. The dildo still lodged in my ass which I was afraid to remove without help. The nipple clamps pulling. The twitching in my dick that was always there after climaxing. 

Finally, Frank and Tom turned their attention back to me. They removed the dildo from my rear, then took off the nipple clamps. They helped me stand up as Frank handed me my panties and skirt. "Jo, you are turning into quite the amazing lady," he said with a proud smile.

"That she is," Tom added as he helped me put on my coat. "That she is. Are you ready to go or was there more stuff in here that you wanted to see?"

Before Frank could respond, I interjected "could we PLEASE go home?"

Frank laughed at my response. "Sure, sure. After all, we can see some of the things that were in here another time." He winked at Tom. At least I thought he did. I couldn't really be sure because I was so exhausted that it took all my concentration to hold onto his arm as I tried to put one foot in front of the other.

We walked out of the "show" and back to garage. I gingerly sat down in the truck feeling both empty and sore. "Please, no more tonight. I just can't do anything else. All I want to do is go home and crawl into bed."

"Okay Jo. We'll give you a break, at least as far as sex goes. Just...take a bath when we get home, then you can go to sleep," Frank reassured me.

"Thank you. I promise, tomorrow, we'll do what you want. I just really want to sleep." 

Tom turned on the radio and I nodded off on the way home. Once we got there, Frank roused me and helped me inside and then into the bathroom where he started running the bath for me. "Just strip off your clothes and leave them in here. I'll take care of them for you. And I'll be back with a nightgown for you." He left me to get undressed and it felt so good to take off the jacket...the boots...the stockings...the skirt...the panties...and the bustier. My nipples and ass were still tender, and as I slid into the tub, I felt the water start to massage away some of the pain. I also felt it slip into my still stretched ass. "I guess I'll have to wear a tampon tonight anyway," I thought to myself before closing my eyes and relaxing in the tub.

About 30 minutes later, Frank came in with a pink cotton nightgown. "Here you go. Get some rest tonight, okay Jo? Don't forget, we're still going skiing tomorrow." I groaned as he winked at me and left. "Can't a sistah catch a break?" I thought before getting out of the tub and toweling off. I got dressed in the nightgown, waved goodnight to the guys, and crawled into bed. I passed out with unrecalled thoughts and dreams about what the next couple of days would bring.

To be continued... 



A Lost Bet Ch. 05



I slept soundly that night. For the first half off the night, I don't think I moved from the position in which I'd crawled into bed. I do remember waking up though, about 2 or 3 in the morning, to use the bathroom and get a drink of water. Upon returning to bed, I drifted off into a sleep filled with vivid dreams...much like the night before. This time, instead of falling down Alice's rabbit hole, I dreamt that I sitting in a classroom full of students, and I was one of them. As I looked around, I noticed that there were men and women in the class, but we were all wearing school uniforms. The guys had on slacks, shirts, and ties, and the girls were wearing grey, pleated skirts, white blouses, knee-high white stockings, and black mary-jane shoes...the classic schoolgirl look. The teacher was lecturing on sex education when he started asking students to pair up, male and female. I looked around and there was only one other available person and we were both guys. We looked at the teacher and told him, "we don't have partners."

"Don't worry about it. Just partner up together," he said. "One of you can change clothes and take on the girl's role." My new partner and I looked at each other and it quickly became apparent that I was going to be the girl in this class. My dream partner was 6'3", 220 lbs. of muscle. My 5'9", 190 pound frame made me a man, but once we got the clothes, we realized that he would never fit. Resigned to my role, I quickly stripped off my men's clothes and started donning the schoolgirl outfit. Once I was dressed, the teacher continued his lecture. He talked about sex...STDs and health maintenance...vaginal...oral...anal...how to use a condom...bondage...control & submission...role playing...and on and on. Finally, he started handing out in-class assignments. Each pair was to re-enact something that he had lectured about. He started handing out assignments, and when my partner and I received ours, I blushed. I couldn't believe the assignment we'd drawn. Our task was to role play in front of the class a doctor's visit. 

My partner quickly donned the doctor's coat (I have no idea where it came from...it just appeared in his hand) and told me to go lie down on the examining table. I did. He told me to close my eyes. I did. He told me to raise my arms above my head. I did. Quickly, using whatever tape was handy, my partner tied my hands together to a bar extending above the headrest. I lay there waiting as I felt his hands caress my arms down to my body. He unbuttoned my blouse and I felt him massaging my chest. I could hear the murmurs of my classmates as they took notes on what my partner was doing. I felt him move away from my body, heard a click, then I felt him come close again by my legs. He lifted my legs up and spread them apart. I opened my eyes to see what he was doing and almost jumped off the table as I saw him start to secure my right leg to one of the stirrups. He wasn't giving me just any doctor's exam. He planned to add a gynecological exam to the role play. 

He finished tying my right foot to the stirrup then focused his attention on my left leg. I tried to struggle and get away from him but I didn't have the leverage to do so. Without a second thought, he secured my left foot in the stirrup and left me spread wide open for the class to see. I started to complain in protest and say that this was not a part of the class, but he ignored me. He slid up my skirt then took a pair of scissors and cut my panties off. I cried out and asked him what he planned to do, but I soon had my answer as he came around towards my head, stuffed my panties in my mouth, then used tape to secure them there. Now the only sounds I could make were muffled gasps and moans...both of which I found myself doing as I felt his hands caressing my legs and playing with my balls and cock. 

I felt him start to slide his fingers into my anus. He pulled out some KY jelly to make it easier then stepped back. I couldn't see him. No matter how hard I strained, I couldn't see what he was doing. I felt him before I saw him again. There was an uncomfortable pain in my rear as I felt him try to force something up there. It felt too firm to be his fingers. Then he uttered one word... "speculum." And with that my humiliation was almost complete. I felt the tears in my eyes as I tried to cope with an experience that women dealt with on a daily basis. I struggled and squirmed, but that only made me more uncomfortable. 

So I lay still and let my tears silently roll out of my eyes. As I felt more pressure, I realized he was opening up the speculum making it wider so he could get a better look inside...if that's what he was going to do. But I was wrong. Instead of just taking a look around, he walked away then came back with an enema bag. Somewhere in the distance, I swore I heard the teacher describing what was going on to the class...the elements of control and submission, role playing, anal play, and the like. But I tuned the teacher out. My focus was drawn to the feeling of the liquid being forced into my body. It started to feel warm...then warmer. I started to feel pressure build up and I started squirming, trying to get away. But it didn't stop. As he started to push the devices in and out of my anus, my hips started to grind trying to find whatever pleasure might be there. 

On and on this went until I felt I was about to burst. I couldn't speak. I could only moan with frustration and a desire to be free from the torment that my partner was heaping on me. I was fighting for control but feeling powerless. My moans continued as I lay on the bed shuddering and twitching, while my partner came up near my head. He leaned down to whisper in my ear "embrace the pleasure, enjoy the pain, and...wake up!"

A searing light tore through my eyelids. "Hunh? What? What's going on?" I mumbled incoherently as I tried to remember where I was.

"Come on Jo. We're gonna be late for skiing, again" Frank said through the door. "Get up, get dressed, and come eat."

"Okay, okay," I replied. As I got over the shock of my rude awakening and started to get oriented as to where I was, I lay back on the bed and stared at the ceiling and tried to remember what I'd been dreaming about. Minute after minute, I lay there trying to remember. But all I could come up with was that I felt aroused, and full. My hands found their way to my erection and began to caress it through the nightgown, but it took me a minute to remember that the full feeling I had was caused by the tampon in my rear. "Shit...I guess I should get up and take care of things. First and foremost, get rid of the tampon, then maybe I can focus." My thoughts were starting to gain clarity through the early morning fog. I rolled out of bed and gathered my things so that I could get cleaned up and ready to hit the slopes. 

As I made my way towards the bathroom, Tom called out "that must have been some dream Jo. You were moaning like a champ." I blushed as I scurried into the bathroom to relieve myself. After finishing with the can, I pinned up my wig then hopped in the shower. The water felt exquisite as it ran down my body, washing away the remaining tension from the day before and opening up my mind to the possibilities of the day. I finished up the shower then got ready for skiing. With the panties and bra, thermals, turtleneck, stretch pants, and vest, I was ready to go. A little light makeup and pulling my wig into a ponytail, I stepped out to meet the guys. 

"Good. You're ready," said Frank. "We're late, so we put breakfast in a bag for you. We're heading to a different resort today, so that's the reason for the rush."

"Oh, okay. Well, let me put my shoes on, then we can go." I rushed to slide my feet into my boots and grab my coat, hat and gloves. "We're off." As we piled into the truck, we talked about plans for the day. But slowly, the conversation drifted back to the events of the day before.

"You know, Jo, I've gotta give it up to you," Frank said. "You were something to see yesterday. Very sexy. Probably sexier than you thought you were."

I found myself blushing again. 

"Yeah Jo," Tom added. "As a matter of fact, we got a number of compliments...about you. Some of the people who saw you with us were impressed by your...performance. They actually wanted to meet you, but we told them you'd be tired. So, we arranged to go out to dinner tonight with a couple of the people that were there."

"Wait...are you for real?"

"Sure. It's no big deal. And it's not like you haven't been out dressed before. I mean, did you already forget being my arm candy all day in the casino yesterday?" Tom asked.

I tried to respond, but no words were coming out.

"Don't worry about it Jo. Dinner will be fun. Besides, we promise to have it just be dinner. Nothing you don't want to do."

"Frank, you seem to forget that this whole trip has had elements of me doing things I didn't want to do," I responded.

"Perhaps that's true," Frank said. "But can you honestly tell me that you haven't been enjoying yourself? Way, deep down...honestly...have you enjoyed yourself?"

I sat silently for a little while as I gathered my thoughts. I thought about the shopping trip on the way to the slopes. I thought about the bondage and being fucked by Tom and Frank. I thought about my willingness to ski while en femme. I thought about the sensual evening that Frank and I spent together. I thought about Tom's treating me like a lady, his lady, while we were at the casino. I thought about the display that I'd put on at the sex show. There were a lot of parts that I had been uncomfortable with, at least on some level. I guess, if I'd really wanted to avoid any parts of it, I could have started by not coming on the trip, especially since I knew what their goal was. I could have fought harder and been a less compliant lady. If I'd had the courage, I could have gone to the cops, dressed as I was, endured the humiliation of other people's thoughts and perceptions, but at the least, I could have gotten a ride to the bus station and a ticket home. I could have fought Frank's kindness and not accepted his gentle overtures. But I didn't. I didn't do any of those things. I went along with each step of their plan, giving up a little of myself along the way. Why? Did I really want to be a woman? Did I want to be their woman? What would happen when we got back to "civilization?"

"Frank," I started, "I'm not going to say that I didn't have times when I enjoyed myself. I mean, I've gotten past the stage of hating you and Tom for what you've forced me to do. And I guess, if I'm being honest, I've even allowed myself to enjoy some parts of it. That doesn't mean that I'm totally comfortable with everything that's happening. But I guess everything that's happened has tapped into some deep curiosity in me. Granted, I feel resigned to my fate of being your woman for the trip, and I imagine that I'll be in this role again at different points in the future. Hell, I might even have a little anticipation for some of those times. But, I'm still not sure what this all means... I guess, yes, I have enjoyed myself on some parts of this trip more than others. But I've also found myself doing some things that I would not have otherwise done if there were not some fear there about the possibility of something worse coming down the line."

"Jo, we're not going to hurt you, and we're not going to let anyone else hurt you...at least not in a way that causes any permanent damage," Tom interjected. "But we are pushing your limits, and we know that. Be hesitant. That's fine. Be wary. That's cool. But let go and enjoy it. Enjoy the surrender...the release...the powerlessness. You might even find out some things about yourself that you didn't even know were there."

I stared out the window at the passing trees. "Maybe..."

"Jo, tell me something," Frank paused before he continued. "When you're dressed as you are, even though it wasn't necessarily your decision, how do you feel?"

"I don't know. Soft I guess." 

"Keep talking Jo," Frank encouraged.

"I feel...feminine is a word I would have to use. Maybe vulnerable too. I mean, it's a little scary to be out in public like this." I paused for a moment to gather my thoughts. "I am glad that we're in an area where nobody knows us because that makes it easier. But I still feel nervous about what someone might say if they read me."

"Okay, but what about when you're in a situation where nobody cares...like the sex show?" 

"Well, there it was different. I felt out of control there because for the first part, things were being done to me...that spanking and whatnot. I guess it was different when you made me fuck myself with the dildos. I mean, I was more in control in the sense that I was doing myself. I could control the tempo, the depth, the position...all that was under my control. I lost myself in my head at that time and started to think of myself as a woman. Or at least I thought to myself, how would a woman respond if she were in this position? But I still felt out of control because I was responding to your commands and instructions...and that made me feel...free, I guess is the word. I didn't have to worry about what I was doing because it's like I was being told to do it."

"Kind of like you were being given permission to let go?" Tom asked.

"Yes," was all I could say. "It's not a feeling that I've had before, especially not in a sexual situation. Even with the women that I've been with, I was still the one in charge, and I did like seeing them lose it."

"See," Frank jumped in. "That's all we really want from you...for you to let go, lose control and ride the experience for all it's worth. When else are you going to be in a position to truly explore all those areas of your mind that you're afraid to uncover? When else are you going to be in a position to be so free and out of control because you know you've got people around you who are going to take care of you?"

"Well hopefully, in my next relationship," I retorted quickly.

"Okay, Jo. Fine," Frank said. "Hopefully you'll find that with the girl you don't know yet. But until you find her, why not let yourself go? See what it's like to be in her role. It just might make you a better lover."

Frank was trying to push some interesting buttons at this point, but I had to give it to him. He was making some interesting observations. 

"Have you ever...let yourself go with your girlfriends Frank? Tom, what about you?" I asked, trying to regain some measure of composure.

"I wish I had. But I had to learn things the old-fashioned way," Frank said. "With some of my past lovers, they've been pretty open about things and the way that they felt while we were having sex. Hell, some of them turned me onto some of the same things that we've been doing with you. Now, I've never enjoyed receiving anal sex like you, but that doesn't mean that I didn't let one of my girlfriends stick her finger up my ass, just out of curiosity. It just didn't do it for me, not like it does for you."

"Same here," Tom added. "I've been into the bondage thing with my girl for awhile. We switch it up. Sometimes she's in control, sometimes I am. But whatever the case, we've both learned how to push those limits and learn how to be free in the moment."

"So, you're saying that you've done all these things for me for MY benefit?" I replied sarcastically.

"Honestly Jo," Frank looked thoughtful as he prepared his response. "Not entirely. Yes, I've thought you could stand to loosen up a little bit, but I also thought that it might be fun to step outside the lines a little and see what was there. Now that I've gone there, I've got a few more ideas of things to do with my girl."

I sat back, feeling pensive as I saw the sign for the resort coming up.

Tom said, "look, why don't we table things for now, and we can continue this discussion at dinner. Alright? For now, let's just hit the slopes and have some fun."

"Sounds like the best plan of the day," was Frank's response. "Jo? You okay?"

"Yeah. Just thinking." We grabbed our stuff from the back of the truck and off the ski rack and made our way to the day lodge. "I'm going to run to the 'ladies' room. Can you watch my stuff for me?"

"Sure Jo," Tom replied. "We'll be right here when you get back."

I walked off to the restroom to take care of business. In the hustle and bustle, no one paid me any mind, so I was able to get in, use the facilities, touch up my lip gloss, and head back outside. I found the guys in the same spot that I'd left them. "Okay. I'm ready." 

We stepped into our skis and took off towards the nearest lift. We skied run after run, sometimes just cruising down the slopes, other times playing follow the leader, and other times racing each other to the bottom. We were always careful to try not to fall because whenever one of us did, the other two promptly aimed straight for the fallen friend before sliding to an abrupt "hockey stop" and spraying the downed person with piles of snow. There was probably more laughter during today's runs than during the first day because I was more relaxed in my role. I let the guys treat me like a lady and, in return, I favored them with flirtatious attention. They even play fought over me at one point. All in all, it was a great day on the mountain. The ride back to the cabin was much more relaxed and the conversation flowed more freely. Frank even took to the time to tease me about a couple of guys he had seen checking me out in the lodge. I blushed a little, but teased him back about how he'd been trying to run some game on a couple of other ladies there while he thought my attention was all on Tom. The jokes and banter continued all the way home. Finally, we pulled up to the cabin and took our stuff inside. 

"Jo, ladies first in the shower. We KNOW how long it takes you to get ready," Frank said with a playful tap on my rear.

"That's right. I should get to take my time. After all, this kind of beauty isn't achieved overnight."

"Fine, fine," Tom added. "Take all the time that you need, so long as you're ready in an hour. Don't forget we've got dinner plans."

In the midst of having fun with my guys, I had temporarily misplaced that particular thought. "Right. I'll be ready." And I scampered off to the bathroom, shedding jackets and turtlenecks and ski pants along the way. I thought I heard Frank mumble something about getting his dollar bills ready for a private strip show later on, but I'd already closed the door by that point and was running my shower. I shaved and scrubbed and let the water wash over me. I got out and patted myself dry, feeling clean and refreshed. I sprayed perfume in all my intimate places and reflected on how much I seemed to be getting into my role as a woman. With each passing day, I fell further and further down the rabbit hole...but I didn't care. At least for the remaining time with the guys, I was okay being the girl. I accepted that there were things I should experience and learn about, and if I could find a way to integrate them into who I was trying to be, then it would all be worth it.

I sauntered out of the bathroom and across the hall into my bedroom. Through the door I called out to the guys, "hey, what kind of restaurant are we going to?"

Tom answered, "It's kind of upscale. We're wearing slacks and sweaters. I'm sure you'll find something appropriate."

I rummaged through the clothes that we had bought on the ride up and found a variation on the outfit that I'd worn to the casino. It was a pale blue suede miniskirt with a slit up the left thigh and matching jacket, which I paired with a black bustier with attached garters, black thigh hi stockings, black mesh panties with bows on the sides, and black 4" pumps. Probably the most striking feature of the outfit was the length of the skirt. It was short enough that you could see the tops of my stockings even while I was standing, but when I sat down, if my legs weren't crossed, my panties were pretty much in full view of anyone sitting across from me or next to me. I knew that the outfit was a little risqué given our location, but I figured that I might as well have a little fun with the guys. I let the hair from my wig fall across my shoulders and stepped out into the hallway.




A Lost Bet Ch. 05



"Hot damn Jo! You look amazing!" Frank had a look of awe on his face as I turned around to give him the full effect.

"What? What?" Tom called out from the shower. 

"Don't worry about it," Frank responded. "You'll see when you're done." Frank returned to memorizing every curve that was hinted at by my outfit. I could have sworn I saw him licking his lips. 

"You look pretty dapper yourself," I said to him to try and get his attention focused anywhere else. I was afraid that he might decide that he wanted to have me as an appetizer...which might not have been too bad, but I still wanted to maintain some level of decorum.

"Thanks Jo," he replied. "Can I get you anything while we're waiting on Tom?"

"Just water, thanks. Now what you can do is tell me about the people we're supposed to be eating with. I know you said that you and Tom met them during 'my show,' the other day. But who are they? What's the plan for tonight?"

"Well, it's a group of about 3-4 people that we're planning to meet at the restaurant. It's supposed to be 2 couples, males and females. The plan is just to enjoy a night out on the town and to meet some new people. Whether or not anything physical happens...we'll just have to wait and see. But I do know that the women want to get to know you. Back at the show, they were real curious about what your experiences had been like."

I nodded as I thought about what I might tell them. As I sat down to wait, I watched Frank's eyes follow my every move. I gave him a little show when I crossed my legs and I know I saw the front of his pants start to bulge. "Everything okay Frank?" I asked sweetly.

"Hunh? Oh, I'm fine. You know...just...taking in the sights," he said with a smile. "And I've gotta say, you are a helluva sight."

Tom finally came out from the back room to join us. "So what was all the commotion ab...?" He stopped dead in his tracks as he gave me the once over...then the double-take. "Jeez, I think I'm having a heart attack." Frank and I laughed. "Seriously, Jo...you look amazing."

"Thank you Tom." I smiled at him.

"Frank, do you notice that something seems different about Jo? There's something...I can't quite put my finger on it..."

"You're right Tom," Frank said. "I had the same feeling but I also wasn't too sure about what it might be." They looked at each other, then looked at me as if they were waiting for an answer. I sat for a minute soaking up the ambience and letting their minds work before responding.

"Guys, it's nothing physical. I didn't do anything different. The clothes are the same ones we saw in the store. The wig is the same one I've been wearing for the last few days. The amount of makeup I'm wearing hasn't changed, still just a little lip gloss." I paused before continuing, "The only thing that's different is my attitude." I looked each of them in the eye for a moment, trying to see if they understood. I decided to tell them a little more. 

"Look, while we were talking this morning, you gave me a few things to think about. And some of it represented the same 'struggles' we've been having since you guys started me down this path. Don't get me wrong, once we get back to civilization, my male stuff is coming back. There will still be basketball and football and poker and all the things that generally like to do when we're hanging out. But what I've finally come to grips with is the idea that, in a situation like this, where I'm under someone else's control, I'm free to do whatever I want and be whoever I want. Granted, it's not like I'm going to go out and be some tramp or floozy. That's just not my style. But I can get into being a lady, even one who occasionally acts a little slutty for the guys that I'm with, which is basically you two. I know that there are still things we might explore, but we've already done a lot. I've experienced a lot as your 'girl,' and it's been an eye-opener. A little uncomfortable, sometimes more than others. But I'm accepting that I've still done most of these things willingly, even under the threat of punishment, it was still my choice. And there have been parts that I've enjoyed. So, I say let's see where this goes. For this trip, I'm your lady and I expect to be treated like one. Of course, I think we're all about to see just what that means, but it ought to be an interesting experience. I guess you could say that I've gone over to 'the soft side.'"

The looks on their faces as I'd been talking changed from curiosity to confusion to understanding. They knew that I'd finally stopped resisting and that I was ready to relax and have fun and be open to whatever it is they still wanted to show me. I knew them well enough to know that they would still treat me with a level of respect, but I also knew that they still had some kinky stuff up their sleeves that they were waiting to roll out. 

"Are you ready?" I asked them.

"Yep," replied Tom. "It's about that time."

"On so many levels," Frank added. "Let's go." Tom simply nodded as he helped me put on my outer coat. As we walked to the truck, Frank was even gentlemanly enough to open the door for me and hold my hand as he helped me in. Before long, we were cruising down the road on our way into town to meet our companions for the evening. Along the way, we recounted our day's exploits on the mountain and laughed at various jokes. We also talked about future get-togethers...where we might go and what we might do. We arrived at the restaurant almost too soon. 

As soon as we walked in, Frank waved at a couple in the waiting area. "Hey Gina, Mark. Good to see you again. Have you been waiting long?"

"No, not at all," Gina replied. "You must be Jo," she said as she turned to look at me.

"I am. It's nice to meet you," I replied with an outstretched hand.

"Oh come, come," she said as she pulled me into one of those hugs that girls tend to give each other. "I've heard so much about you that I feel like we're already friends." Her smile was mischievous, but sincere. "You look delectable in that outfit."

I smiled and complemented her back, "so do you. That dress looks fantastic on you." She gave a little twirl in her burgundy cocktail dress. "You're not too cold, are you?" I winked as she glanced down and saw her nipples pointing through the dress. She laughed.

"Not really. Besides, I've got Mark to warm me up." In the midst of me getting to know Gina, Mark had gone on to greet Frank and Tom. As I looked at him, I thought his face was kind of familiar and I realized that he must have been at the show earlier that week. 

"Are the others here?" asked Tom.

"Yep. Elise and Alex are already seated," Mark informed us. "They're waiting on us."

Frank, Tom, and I followed Gina and Mark to a private booth in the back of the restaurant. It was obvious that the restaurant was designed to create as much privacy in a public place as possible. As I was introduced to Elise and Alex (apparently both of them had been at the show with Mark), I slid into the booth between Frank and Tom. Everyone chit-chatted as we looked over the menus and tried to figure out what we wanted to order. The waiters brought bread and water and took our drink orders while we continued to get to know each other. 

"So, Jo," Elise started in, "I thought your performance at the show the other day was very memorable. I'd never seen a transvestite live before and you looked like you were enjoying yourself." I felt my face get hot and was thankful that my brown skin hid what would have been a raging blush. "I've been dying to know how long you've been dressing and what it feels like for you."

"Oh definitely," chimed in Gina. "I really want to know the full story because you really do look amazing and feminine and you seem to really enjoy being with Frank and Tom."

"Well...would you believe that this whole 'situation' started with a bet about 6 months ago?"

"No," Gina gasped. "Six months? That's it?"

"It's true," Frank said. "Tom, Jo, and I were playing poker and Jo lost a bet. He had to do whatever we told him to do and we asked him to dress like a girl."

"So, you had him dress like a girl. Did he look as good as he does now?" Mark asked.

"Did you do anything else that day? That's the real question," Alex chimed in. 

"Well, we shouldn't kiss and tell..." said Tom, "but since we did more than kiss, I guess it's okay." Everyone laughed. "Once we got Jo dressed, it didn't take long before we had him serving us drinks and food...and after a few minor disagreements regarding point of view, Jo came around."

"Oh really?" asked Elise. "How so?"

Frank took this part of the response. "Well, he came over the couch after we tied him up and popped that cherry. He actually sucked his first cock that night...at least as far as we know."

"That was my first, thank you very much." The group laughed at my playfully indignant response. "The guys were my firsts for a lot of things. And I'll be honest, that first night left me pretty pissed off."

"I'll bet. It's just like a couple of guys to take advantage of a vulnerable young lady," Elise laughed as she responded with partial sympathy and scolded the guys. "Seriously though, you must have had a rough time."

"I don't know Elise," Gina replied. "After the first couple thrusts, I'd have imagined that Jo had a pretty smooth time." The laughter flowed freely at this point. The waiter returned with our meals so we put the conversation on hold while he was there. After he left, we started right back in.

"I'll be honest, it took me a few months after that night to even be willing to risk going out with those two again. My issue was that they told me that, now that they'd had me once, they were going to make it their goal to have me again and again whenever we were in private. That kind of scared me."

"So how did this trip come about?" asked Alex.

"It really happened because Jo made a mistake," said Tom. "Jo finally came by to hang out with us again for the superbowl. In the midst of the excitement of the game, he made a bet with Frank and Frank won...again. The bet consisted of this trip and Jo's obedience. And we have to give it to him, Jo has been a total sport going along with the bet. We've actually been talking a lot over the last few days and Jo has been coming to grips with 'her' position."

"Is that so?" asked Mark. I thought I caught a gleam in his eye.

"Within reason," I quickly added. "Yes, I've done some things over the last few days that are WAY out of the norm for me, but that's because Frank and Tom have generally treated me with respect and not made any demands that were inappropriate for the situation."

"So," Elise asked, "you were willing to do the demonstration at the sex show because everyone was doing it and it was basically okay?"

"Yes," I responded. "I'm not going to do anything in public that's going to cause me any unnecessary embarrassment and Frank and Tom have respected that. And as long as they continue to respect that, then I guess I'm willing to try most of the things they want to do...in private."

"So, what say we test that theory," Alex challenged.

"What are you thinking Alex?" asked Gina. Elise and Mark also looked curious, but I got the sense that they already had some ideas.

"Frank, if you and Tom are willing, how about we swap partners for the night?" 

"What, you want to trade Jo for Elise?" Frank asked.

"No. I want to trade Elise and Gina for Jo...for Mark and myself." Alex said.

Frank and Tom looked at me. "What do you say, Jo? Are you willing?"

To be continued... 



A Lost Bet Ch. 06



Everyone at the table looked at me as they awaited my response. I couldn't help but reflect that just a few days ago, I would have incredibly nervous and scared and on the spot and would have been unable to make a decision. But with my newfound freedom, I knew I could give them the response they were waiting for. Of course, I was still a little nervous because I didn't know how I would be treated by Mark and Alex, but I knew I would still go with them for the night. I looked up.

"I'll do it...on a couple of conditions."

"What are they?" asked Mark.

"One...you have to treat me with the same respect that Frank and Tom showed me. Two...I do have some limits and I expect you to respect them. Three...if I say stop, you stop."

"Wait a minute," Alex said. "How is that any different from your second condition?"

"Well, I can tell you what my known limits are. But I also don't know exactly what you guys have in mind, and I just want the assurance that I'm going to come out of this in one piece with all my limbs and faculties intact."

"That's fair," said Mark. "Basically, treat you with respect, but we can still make you do...stuff. Right?"

"Basically," I responded. "And just to make sure I'm clear, while I'm with you, your ladies will be with Frank and Tom and enjoying all their charms."

Gina jumped in. "Why don't we ladies adjourn to the ladies room and let the guys talk about what falls in and out of bounds. Is that alright?"

A chorus of "yeah" and "yes" could be heard around the table. "Alright, ladies?" And with that, Gina got up and Elise and I followed. As we got to the bathroom, I could feel myself starting to shake with nervousness.

"Okay, be straight with me. Am I in any trouble with your guys?" I asked the others.

"No, no. You'll be fine," Elise assured me. "I'm pretty sure they're going to push your limits though. I know that they've both got some fantasies that they've been wanting to act out, but Gina and I haven't gone there with them. But if they do alright with you, MAYBE we'll consider them."

"Yes, and make sure you tell us everything that they do with you because if they do anything out of bounds, then we'll make them pay for it," Elise added. "But you should be fine. The guys are really sweet. I'm sure they're going to try a few new things though. I'm interested to hear what you end up doing."

"I'll bet that at least one thing they have you do is role play..." Gina started to say before Elise stopped her.

"Shh, Elise. We don't want to ruin all the surprises for Jo," Gina winked. "Don't worry, it'll be a lot of fun. But I don't want to help you get ready for one thing."

"What's that?" I asked.

"Well, since we know you're going to get a lot of 'back door' play, we brought something to help you get 'warmed up.' Turn around." Gina turned me around, while Elise lifted my skirt and pulled down my panties. I heard her pull something out of her purse, then felt her squeeze a tube into my rear. "It's a warming gel. Trust us, you'll like it," Elise said as she continued to squeeze the gel from the tube. "One more thing," she said and I felt her start to slide some of the ben wa balls up my rear. "Just thought you'd like to have a little fun throughout the rest of dinner and on the way back to the house."

"Sure, that's what you say," I responded as I started to feel the warmth. Each movement I made caused the balls to shift slightly, and that in turn brought a different sensation of warmth. "Well, I imagine that you're going to enjoy things with Frank and Tom. I'll have to tell them to try a couple of 'tricks' with you as well." I winked at both of them as I pulled my panties back into place and readjusted my skirt. "Shall we...?" We quickly touched up our makeup and walked back to the table.

As we got close, the guys were all chatting animatedly with sly grins on their faces. "What's going on?" we asked as we settled back into our chairs.

"Nothing, we just got our plans together," said Frank.

"So," Gina asked. "What are they?"

Tom surprised me by taking the lead in answering. "Here's how it's going to go. Instead of just having a few hours together tonight, we agreed that we'll have the ladies until tomorrow afternoon, and Alex and Mark will have Jo until then."

"Okay, that's not such a bad plan," Elise said.

"Oh that's not all," said Mark. "Seeing as how this all got started with a bet for Jo, we figured we'd keep the tradition alive. So Alex and I made a bet with Frank and Tom. The bet is this: During our night together, whoever can come up with the most creative sequence of positions or stories or sensual tortures or layouts...yes there will be pictures for only those of us here...wins a weekend vacation with the partner of their choosing to the location of their choice. Now, we've got one night to be creative. Tomorrow afternoon, we'll get back together at our place where there will be kind of a bonus round. During that time there will be a chance for people to work out larger sequences using more people if they choose to. But the prize for that is something different. For the bonus round, the prize is...equally inviting...$100 in cash from each of the losers to spend on whatever they want at Night Dreams, but they also get to choose a partner who will be their servant for a weekend. That's it."

Gina, Elise, and I looked at each other with a mixture of awe, nervousness, and excited energy.

"We figure that there's a pretty even chance for anyone to win even though Frank and Tom have Gina and Elise, and we have only one Jo," Alex interjected. "See, Frank and Tom can do more with more partners and we know the ladies will be into it. But they're still kind of vanilla at the role playing and bondage and stuff. Even though we've only got one partner, we've got a bit more experience and a few more toys at our disposal so it ought to be interesting all the way around."

"Is everybody in?" Frank asked looking directly at me.

"Gee Frank. I don't think I should bet anymore. You remember what happened the last time..." I replied with a nervous look.

He started to respond, but I think he could see the twinkle in my eye. "You're not serious are you?"

"Nope. Like I said on the way here, I've made some decisions to be free, to experiment, and be the woman you and Tom made me to be, and I'm willing to see what Mark and Alex have to offer. So, I've got just three words for you... Bring...It...On!" Everybody laughed including me.

"Well then," said Gina. "Let the games begin." She raised her glass in a toast, and the rest of us did as well. The check came and the guys were nice enough to pick up the tab. 

"So I guess this is where we say goodnight," said Frank. We all gave out hugs and well wished each other good luck as Gina and Elise followed Tom and Frank to their truck and I started to follow Alex and Mark to their car. 

"Jo, you mentioned your limits back in the restaurant," Alex pointed out. "Why don't you tell us what they are so we can get a sense of what we can and cannot do with you...or to you."

I looked at both guys as we stood next to their car and started to respond. "Well, I'm not at all interested in scat or water sports or things like that. I'm also not interested in pain on having my body marked up or anything like that...nothing that will leave a mark. And like I said before, I'm not really into humiliation, so taking me out in public and calling me whore or slut does nothing for me other than piss me off. I mean, Frank and Tom wanted me to be a lady, so that's what I've been. I'm not a dog or a bitch and I don't expect to be treated like one. But will I be a willing participant in bedroom activities, yes...probably more now than I was when this whole thing started."

"Okay," Mark said. "We can deal with that. Now, I've got a question for you...since all this started, have you had any fantasies?"

I was kind of surprised by the question because I hadn't really expected to be that active a participant. Part of the fun that I'd been adjusting to was giving myself over to Tom and Frank to control. Being asked to contribute ideas was still kind of new so I had to think for a minute before responding. 

"Let me ask it another way because I can see it written all over your face that you weren't expecting the question. Of the things that you've seen on TV or in magazines, has there been anything that turned you on?" Mark was pretty sensitive to my nonverbal cues, so I had a feeling that things would be okay.

"Umm...well, I always liked seeing two women together, but then what guy doesn't?" We all laughed at that. "I also liked seeing women in lingerie, heels, short skirts or dresses, even costumes. And I can admit that I enjoyed seeing some bondage photos, like the sexy secretary tied up at her desk, or kidnapped. Things like that."

"Alright," Alex said. "Now we've got something to work with." He turned and flashed a smile at Mark. "Should we begin?"

"Oh definitely," Mark replied. "If the lady enjoys a good kidnapping scene, then how can we not oblige?"

I started to look at him like he was crazy when the lights went out. I could feel Alex's hand over my eyes as he grabbed my wrist and bent it behind my back. He shifted his weight back and I nearly left my feet. I started to say something, but before I could open my mouth, Mark stretched a piece of duct tape over it. There was a part of my mind that was wondering where he got the tape from, but before I could focus more on that, I felt my other wrist being pulled behind my back. Once Mark had both my wrists behind me, I felt him tape my hands together clasped as though I was in prayer, making sure I couldn't get free. He pulled up on my wrists forcing me to bend over at the waist.

"Looks like the girls already started getting Jo prepped for us," Mark said to Alex. "She's got the ben wa balls in."

"Good. That will be fine for the ride home. Let's do her legs then get her in the car," Alex said as he opened the trunk and pulled out some rope. Quickly and efficiently, they bound the rope around my elbows, wrists, knees and ankles making me feel incredibly helpless. Abruptly, Alex and Mark picked me up and set me down on my stomach in the trunk. Just as quickly, they tied my wrists to my ankles, putting me in the hogtie position. I started to mumble through tape, but nothing came out other than moans and grunts.

"Don't worry, we've done this before. We've rigged the trunk so you'll have plenty of air. Other than that, we'll see you at the house." And with that, they closed the trunk. I was kind of nervous and a little scared as I considered my situation. I figured that I could trust them, but things had gotten off to such a fast and unexpected start that I realized that I didn't really know what to expect. I had time to mull over my thoughts while we were moving though. I was actual thankful that they'd done this before because they'd seen fit to put some padding in the trunk to keep me (or whoever was occupying it) from getting additional bumps and bruises, and I appreciated that. Still, I wanted to know what they had planned.

I had no sense of time while we were riding around, but knew that we couldn't have been in the car for more than a few minutes when I felt us stop and heard them shut off the engine. I heard their muffled voices through the lid of the trunk but then heard them walking away. I let out a muffled call for assistance, but all that came out was "mmmppphhhh..." There was no answer. I tried again, but still no answer. I couldn't understand why they didn't take me out. I lay still for a few minutes but started to worry as the seconds continued to tick by and I heard no sounds. I actually started to cry softly because this was not what I had anticipated. After an insufferable eternity (but what couldn't have been more than 20 minutes) I heard sounds outside the car. The lid opened and relief flooded my body.

"Aww Jo, were you crying?" Alex asked. "We just had a couple of things we needed to get ready for your arrival." Then he snapped a couple of pictures. "Struggle against your bonds, just a little." I did as he asked, moaning all the way as he took a few more photos. "Good. We're off to a good start." He reached in and released me from the hogtie position but left my arms and legs bound together. Slowly, he and Mark reached in and pulled me out of the trunk. As they set me down, they leaned me against the car.

"What do you think? Should we start her off upstairs or down?" Mark asked Alex.

"Down, definitely. We'll save the upstairs for later on in the evening." Alex then proceeded to unceremoniously toss me over his shoulder as he made his way into the house, and down some stairs into the basement. As he turned around the pole at the bottom of the stairs, I tried to look around and could see a few things...like dildos and vibrators in one corner, straps and whips and other accoutrements in another...and a chest on another wall. I never saw the last wall, but my attention was drawn to the chest. It looked to be padded on the outside and there were straps at the corners, but I could also see where it could be opened and I wondered what was inside. 

Alex set me down in the middle of the room and helped me get as steady as possible while being tied as I was. "Now that we've kidnapped the 'secretary,' what should we do with her?" Alex looked at Mark while they both pondered the question. 

"Well," Mark started, "if I was her kidnapper I'd want to make sure she understood just how powerless she was to stop us from doing whatever we wanted to do with her." As he said these words, he looked me dead in the eye. I let out a mew of understanding and felt my body fill with a mix of fear and anticipation. Mark leaned in real close and ran his hands over my body as he whispered to me "you do know that you're under our control now, right?" I nodded. "Good. We'll make sure you get some enjoyment out of this, but remember, you've got to put on a good show. Of course, if your show outdoes ours, we'd actually have to face the possibility of losing the bet. But I don't think you've got it in you to be better than us." He started running his hands over my body as he was speaking and with each touch, I felt myself wanting to move away from him, but also towards him as I wanted the touches to continue. Slowly, he ran his hands across my breasts, feeling the corset and my nipples trapped within it. He slid his hands down and caressed my ass through my skirt.

"You know we're going to have to untie her in order to get her coat off?" was Alex's comment.

"Oh, I know. Why don't you get started on that while I get her ready for the first part of our activities." And as Mark finished his statement, he started sliding my skirt over my hips and pulling it down my legs. He didn't just let it fall though. He intentionally held on to it and slid it down so that his hands never left my body. The feel of his strong hands caressing my legs through my stockings had an immediate reaction on me and I felt myself getting excited in my panties.

Alex came behind me and started cutting the tape off my hands. As soon as they were free, I flexed my fingers with relief. My wrists and elbows were still bound, so I was limited as to how much freedom I could experience.

"Mark," Alex said. "Before I take off her coat and release her bonds, I think I'd like to have a little fun first."

"Go ahead," was Mark's response as he backed away. "What did you have in mind?"

"Just this..." and Alex bent me over at the waist. I heard him pulling on something, then felt him lift my wrists into place and latch them to something. He pulled some more and I felt my arms being raised behind me, forcing me to stay bent over. My hair fell around my face, blocking my view of anything that they might be doing. I could feel Mark's presence nearby and had the sense that he was there to make sure that I didn't fall over. Then I saw Alex's feet in front of me and I struggled to look up.

He pulled the tape off my mouth slowly, carefully, and with a minimum of discomfort. "Are you ready Jo?"

"Ready for what?" I asked. Then I heard him unzip his pants and I knew exactly what he had in mind. I nodded and he moved closer to me with his cock in his hands. As it got within reach, I tried to kiss it and lick it a little bit. After a few moments of straining, I started to open my mouth to take it in and Alex obliged me by sliding it between my waiting lips. From my bound position, there was only so much I could do, but Alex was more than happy to take control and slowly fuck my face. Gently and firmly, he continued to stroke himself in and out of me. Occasionally as he pulled out, I started to fall forward and Mark would grab my hips and hold me upright. The minutes went by as Alex continued to work on getting his rocks off in my mouth when I felt his rhythm change and he started to pump a little faster. Mark held my body stead as Alex held my head and took total control. Before I knew it, I heard him grunt and I felt stream after stream of cum flowing into my mouth. I started to sputter and Alex pulled out a little so that the overflow could escape, but he didn't remove himself entirely, forcing me to swallow as much as I could.

"That was nice," he said. "Mark, do you want to try her out? She's actually got a very nice mouth."

"Nah, I've got a plan to take her ass. Seeing as how you've had first crack at her, I'd like your help getting her set up for my turn. So, continue undressing her for me, then let's move her to the X facing the wall." I felt Mark loosening the bonds on my hands, letting me down so that I could once again stand upright. As I was helped back into a standing position, Alex moved in and gave me a deep kiss, then he licked some of his cum that had escaped from my mouth from my chin and kissed me again.

"That was unexpected," I breathed into him.

"Who says 'kidnappers' can't be gentlemen?" he asked with a wink. As Mark continued to untie my wrists and elbows, Alex bent over and started untying my ankles and knees, caressing them and massaging some of the feeling back into them. Mark finished with my arms and slid my jacket off my shoulders and down my arms. He tossed it off to the side, on top of my skirt.

The guys escorted me over to the X and I wondered what was the next thing they had in store for me. I knew I wouldn't have long to wait as they moved me into position facing the X. Mark wrapped some leather cuffs around my ankles, spread my legs and secured them to the base of the cross. Alex fastened similar cuffs around my wrists and secured them to a couple of chains hanging down from the top of the cross. I expected him to then pull the chains so that I was stretched taut against the cross, but he surprised me when he left my arms dangling lightly. I still couldn't move much, but I wasn't snug against the X.

"Alright," Mark said. "Now, I think we're ready."

"Ready for what?" I asked innocently.

"Funny girl. Keep talking and we'll have to silence our captive." Alex responded in such a dramatic fashion that I couldn't help but laugh.

Mark came up behind me and grabbed me by the waist, backing me away from the cross until I was almost hanging from my hands and ankles. "Ok, ok. I'm sorry." I wasn't in pain, but a little off balance and I didn't want to fall into the cross. Mark continued to hold me as he caressed my ass through my panties. Then I felt him untie the bows holding my panties up and pull them from between my legs. My cock sprang out erect in front of me and my ass got goosebumps in the chill air of the basement.

"Nice butt," Mark whispered as he pulled me close to him. He started kiss me on the side of my neck and caress my ass with his right hand while his left hand held me close to him. His kisses aroused me and I started to squirm under his ministrations. It didn't take long before he started playing with my hole. Quickly, he distracted me with a light bite on my neck. I gasped, then he slid a finger into my ass, and I gasped again. Slowly he started finger fucking me with one...then two fingers and I moaned a soft "ooohhh..." I'd almost forgotten that the ben wa balls were still in my ass until he started moving them around. Unintelligible sounds escaped my lips. He surprised me by quickly pulling the balls out, then sliding a tube of lube just past my anal ring and squeezing.




A Lost Bet Ch. 06



I yelped at the cold liquid being let loose inside my rear until I felt a new pressure. Mark had his cock pressed against my hole and was slowly...slowly entering me. He pushed against my hole and my ass expanded. My breathing increased as I tried to accommodate him, but he kept pushing and I'd never felt anything that wide before. I tried to adjust and I heard myself say "too big...too big...never had...anything...like you..."

"I thought you'd enjoy the surprise," Mark said and I could almost hear his grin.

A couple of tears escaped my eyes as I tried to cope with his size. "God, Mark. How big are you?" I managed to choke out.

"Almost the size of your wrist." My eyes snapped open as I looked at my wrists stretched in front of me.

"No way. No way." I couldn't believe it. I mean, it's not like my wrists were huge or anything. They were actually kind of all the small side for a guy, but still, Frank and Tom weren't that wide and I'd been unprepared for him.

"Just a little more," he said as he continued to push into me. The pain started to turn towards pleasure, but the pressure was unbelievable. I felt him deeper in my bowels than anything (except for the dildo at the show...maybe) and I was starting to shiver from the exertion. "That's it Jo, that's it. You're doing fine. As a matter a fact, I think you're in for a helluva ride." And with those words, he started to slowly pump in and out of my ass. My cries echoed off the basement's walls...random sounds like "ooohh" and "aaahh" and moans and a couple of choked sobs...until finally, the pleasure overwhelmed the pain, and a steady stream of "yes" and "oh Mark" became the norm.

Because of my position, he was pumping up into me, and my feet were pretty much lifted off the floor. It was almost like he was holding me in the air while fucking me and it brought new feelings of vulnerability to me...along with tight arms and legs. The minutes passed and Mark started fucking me faster and faster. My cries got louder and louder, the pitch higher and higher until I was practically squealing as I rode Mark's pole (best description of what he was packing). I couldn't stand it any longer. I began to cum and I saw my cum shoot in front of me, falling on the cross. Finally...he came. Jet after jet of cum emptied into my ass as he continued to pump in and out, until with his last exertion, he planted his dick hard in my ass and my mouth opened in a silent "O" as I stared at the ceiling in extasy, seeing nothing.

"Oh God...oh my God...I think I'm dead." I tried to get a sense of what was going on, but I felt utterly disoriented. Alex was laughing in the back at my reaction, and I could almost feel Mark's smile. With an audible "pop" he pulled out of my ass and my body went limp. I could feel his cum draining down my leg as I slumped on the bonds securing me to the cross.

"Ah, ah," was Alex's comments. "I don't think we're quite through with you yet." I looked up in surprise because I was sure they couldn't have more planned for me, not after that. I watched helplessly as he went and pulled the chains. Now, I truly was stretched against the X. Had it not been for the restraints, I most definitely would have fallen in a pile on the floor.

"That was a good warm up. Next time around, I'll definitely have more staying power," Mark said.

"What, like 30 minutes was too short?" Alex commented. "You were just too excited to get in her ass."

"True, true. And it was a delicious experience," Mark responded. "Jo, I think Frank and Tom did you a favor by putting you in this position. I mean, I'm sure you're a great guy, but you are an amazing chick. Shoot, we might even give them a thank you card." They both laughed and I smiled, but I still wasn't too sure about whether or not I shared their sentiment. I pushed the thoughts aside and resolved to deal with them later.

"Well, I'm glad you're enjoying yourselves. But, can I request a change of position? My arms are getting a little sore." I tried not to whine, but I couldn't help the pleading tone in my voice because my arms were starting to feel like they were on fire.

"Sure Jo, in just a second, we'll let you down. Just...hang on," Alex collapsed in laughter at his pitiful humor as Mark and I both groaned. Mark finished cleaning himself up and getting his pants back on straight.

"You know, I'm kind of thirsty." Mark looked over at Alex. "You want a drink?"

"Actually, I would. Jo, would you like something to drink?" asked Alex.

"Umm. Yes, I think I would." I was skeptical about what they had planned and was trying to figure out whether my choice was the right one.

"Fine. We'll help get you ready." Mark replied, but he walked away from me. I couldn't turn my head that far around so I didn't know what he was doing. "Don't worry Jo, we're just getting a chair for you." I felt some relief at those words, but it would last long. I heard them positioning the chair and then felt them come over and release my hands.

"First things first," was all that Alex said as he unchained my wrists and removed the cuffs. He positioned my arms behind me so that my arms were bent at the elbow and my arms were crossed. Then he tied my arms together, hand to elbow, which forced my chest forward as my back arched. "Okay, hold on to this button. We told you we wanted you to be safe, so only press it if you feel like things are going too far. One or two more little additions up top." Alex fastened a collar around my neck which forced my head stay up. I could no longer look down and see what they were doing, although I could still turn side to side (in a limited fashion).

By this time, my ankles had been uncuffed from the X and Mark had positioned the chair behind me. After Alex finished with me, Mark lifted me up and set me on the chair. As he did, I felt myself being penetrated by the chair.

"What the hell? What kind of chair is this?" I asked.

"It's a chair with a couple of little modifications," Mark said as he then pulled my legs together and started binding my knees together and my ankles to each other. "For instance, you felt the dildo enter your ass, right?"

"Yes."

"Well, it's not just a dildo. It's also a...special kind of enema delivery system." My eyes grew wide as I started to wonder what kind of discomfort I was going to be experiencing. "You see, with this system, you're in control. You have some measure of control over how much liquid gets forced up your ass."

"Okay, so how do I control it?" I was anxious to figure out what I was going to do, and why all this was necessary in order for me to get a drink.

"You suck on this," Alex said as he slid a penis shaped gag into my mouth. "Mmmpph..." was all I managed to get out. Alex held up a tube hanging from the end of the gag. Mark wheeled over a cart with two bottles on it. Alex attached the tube from the penis gag to the smaller bottle, while Mark attached a tube from under the chair to the larger one.

"It's simple really," Mark commented. "The more water you suck, the less water gets forced up your rear. But when you stop sucking, the pump kicks in and water goes in the back door. So, you may want to pace yourself."

There was nothing I could say as I watched them flick the switch and turn on the pump. Immediately, I felt liquid filling my insides, and they were filling fast. I started to suck, but I couldn't find a good rhythm. I turned my head as much as I could to look at them and plead with my eyes to have them let me go. But they only looked back at me with smiles on their faces. "We'll be back in a few minutes. We're gonna get some drinks, call a couple of friends and come back."

With a petrified look on my face, I watched them walk away and tried to figure out what they could possibly want to do next before I resumed sucking down my water and filling myself up like a balloon. I was starting to wonder if maybe I'd gotten myself in over my head, but I had the panic button and knew I could stop it all if I wanted to. 

The question was, did I want to? 



A Lost Bet Ch. 07



As I sat there and tried to keep my breathing out of the panic range, I continued reflecting on my options. After the first couple of minutes of alternating between swallowing with my throat and swallowing with my ass, I found a rhythm and pace that worked. But I didn't know how long I was going to be able to hold out because I was really starting to feel full. I had no idea how long Alex and Mark were gone, but I knew that if they didn't come back soon, I'd have to hit the panic button simply because I didn't want to drown. Already, with each turn of sucking on the "straw", I felt water leaking out of the corners of my mouth. Finally, when I didn't think I could take anymore and I felt like I was going to explode and was on the verge of hitting the panic button, I heard someone say "relax Jo...just slow yourself down, and relax." I looked up to see Alex sitting on the stairs, with Mark's frame highlighted by light from upstairs. "You didn't really think we'd leave you in such a precarious position with only a panic button, did you?"

Alex turned and nodded to Mark, then proceeded to come down the stairs and caress my face. I moaned a plea around the water with a tear in my eye and Alex moved close to reassure me. He shut off the water flowing through the penis gag and gave me a chance to swallow the water that had started to leak from my lips. "You were never in any danger Jo. I admit, your reaction was priceless and the desperate look on your face was such a turn-on, but we had our eyes on you the whole time."

"How's she doing?" Mark called down from upstairs.

"She's fine Mark. A little unnerved, but not broken. I think she just got a little taste of how extreme even little things can get." Alex kept petting my head as he talked and I found it incredibly soothing. "Still, I think we ought to move on to something else because I doubt that Frank or Tom would appreciate it if she ended up getting hurt through our games."

Mark moved to shut off the water pumping into my rear while Alex gingerly removed the penis gag and I coughed up a little water. 

"Are you okay?" Alex asked.

I nodded, coughed again and squeaked out a "yes, but I REALLY need to go to the bathroom."

Alex and Mark laughed at that, and Mark proceeded to lift me up off the chair and put me over his shoulder. I groaned and felt the water sloshing inside of me. Being on his shoulder only made me have to go to the bathroom more. "Please hurry...I really have to go and I don't know I can hold it in much longer." And with that statement, even as I clenched my cheeks together as tightly as possible, I felt a few drops leaking down my legs. Mark started walking with me towards the bathroom and Alex followed. As soon as we got there, he set me down on the toilet. Thankfully, my penis was already tucked so when I started to pee, it was pointed in the right direction. My ass opened with the barest urging and with an audible splash, I heard the water filling the bowl. I was visibly relieved and Alex and Mark smiled at my apparent relief. While I sat there, Alex undid the collar keeping my head in position and Mark started to unbind my legs. Multiple types of relief started to flow through my body. Every time I thought I was through though, more came out. Alex was kind enough to untie my elbows, but he left my wrists bound together. Finally, after a few minutes, I was through and Alex and Mark helped me to my unsteady feet.

"Here we go," Mark encouraged as they walked me back into the playroom. "We're expecting company in a few minutes." They sat me down on the bed in the room and (finally) untied my wrists. 

"Who's coming?" I asked. Mark slid my legs onto the bed and Alex nudged my shoulders down towards the bed. 

"Roll over," Alex gently commanded. I complied and the guys proceeded to massage my arms and neck, legs and back. The feel of their strong hands working out the kinks that had developed from being bound in so many different positions almost sent me in to neural overload. I didn't moan...I purred from the feeling and relished the sensations being wrought on my body. 

"To answer your question, a couple of ladies that we're familiar with are bringing their new boy-toy by. When we told them about you, they were absolutely insistent about coming by to meet you. I think they have an idea to do to him what Frank and Tom did to you...and they want your assistance." I abruptly looked up at Alex. "Relax and enjoy the massage. After talking with Tom and Frank, we, and they, realize that you've been on the receiving end of a most of these experiences...so to speak. So Mark and I agreed that it would be a good break for you to be on the other side of things for a little while. Are you okay with that?"

I closed my eyes and pondered his words for a minute. I wasn't sure what was expected of me. "Tell me more. I mean, what do these ladies expect me to do?"

"Well," Mark chimed in, "their new boy-toy is...a bit reluctant to try new things. He loves having sex with them, I mean, they're hot and bisexual, so what guy wouldn't love that? But they want more out of him. They want him to understand what it feels like to be patient and accepting of gentle touches and simple caresses. They want him to enjoy the act of surrendering himself to someone else instead of always being in control. They him to understand that by surrendering, he's actually gaining more control. They want him to appreciate the feeling of being penetrated, fucked, to the point of an earth-shattering, body-focused, over-the-top orgasm."

"Basically," Alex interjected, "we told them about how much you've come to enjoy your experience of being a girl...and we know about the feminine type of orgasms you have. They're written all over your face when you're riding someone's cock. I noticed it here. Frank and Tom noticed when they were having sex with you. And everybody saw it at the sex show (I blushed). Just open up and help this guy get a taste of what could be."

I was still a bit nervous. "Am I expected to be some kind of dom or something?"

"Not unless you want to," Mark responded. "We're not exactly sure that the girls have done that with him yet, but if that's what you're comfortable with, then yes. We'll be there to help as well. What do you say?"

"Okay, I'm in," I replied...as if there was ever any doubt. "But before they get here, can I have some clothes?"

We all laughed at that. Alex stopped rubbing my shoulders and neck as he went over to the chest that I had been strapped to earlier. As Mark removed what was left of my earlier outfit, Alex opened the chest and pulled out a pink bustier with matching thong, a pink ruffled skirt, and some matching pink and white skechers tennis shoes. As I put on the outfit, I relished in its soft comfort. The skirt was light and caressed my thighs and rear, and the bustier wasn't heavily boned so I had a lot of flexibility and even some cleavage to show. And the tennis shoes...after wearing heels for so long, I'd forgotten what really comfortable low key shoes might feel like. The overall look was sporty, yet sexy...and Alex pinched my butt as if to remind of how attractive he thought I was. But I could see it in his face. And as I looked at Mark, a similar look was written on his. Quickly, I leaned over to each one and gave them a quick peck and said "when do our guests arrive?"

The ringing of the doorbell answered the question for me. The three of us walked upstairs and headed towards the door to meet our guests. Alex was the first one there and opened the door. "Hey Chantelle, Maria. How are you?"

"We're good thank you. Hey Mark," Chantelle answered with a wave. "And you, you must be Jo. Cute outfit." She reached out to shake my hand and I shook hers back in a decidedly feminine fashion. I couldn't help but check her out with her long black hair and honey-colored skin. The jeans she was wearing clung to her in all the right places, and the red t-shirt she was wearing accented her breasts quite nicely. As I looked down, I saw that she had on matching red boots. It was a casual, yet very sexy outfit.

"Nice to meet you Chantelle, and thanks," I responded. "And you Maria." Maria smiled and shook my hand as well. I thought that she had to be Latina with her soft round face and brown curls. She'd decided to wear a long jean skirt with brown knee high boots and a white cashmere turtleneck. These two ladies were working their outfits.

"This is Charles," Maria introduced the man standing behind them. "Hi," was all he said as we ushered the three of them into the house. He was probably about 5'10" and maybe 170 lbs. His dark brown skin was accented by the grey sweater he was wearing over his jeans and boots. He was handsome, but he looked a little uncomfortable.

"Please, come in and have a seat," Mark offered as Alex took their coats and hung them in the closet. He led them to the living room (which I hadn't seen yet), and we all took seats. I sat on the loveseat next to Alex while Chantelle and Maria made themselves comfortable on the couch. Charles sat down on the big chair and tried to be casual. Mark kept going through the room towards the kitchen. "I've got some wine in here. Jo, can you help me bring out the glasses."

"Sure," I replied as I popped up off the loveseat and went into the kitchen. Mark had already set the glasses on the counter, so I picked up four of them and walked them back into the living room. Mark followed me in with the other two and the bottle of wine. As we set the glasses down, he started to pour and I passed the glasses around. When everybody had settled in and was sipping, he finally took a spot near the fireplace and I settled back into the loveseat. 

"Well, we're glad you all decided to come through," Alex said. "Everything been going well?"

"Oh yes," Maria replied. "Chantelle and I have been having a great time together. We still miss you guys though. How long are you in town?"

"Just another couple of days. Then we head back to the city."

"Did Elise and Gina come?" Chantelle asked.

"Yep, they're hanging out Frank and Tom, the guys who came up here with Jo," Alex responded. 

"Well, tell them we said 'Hi' and we'll call them later," Chantelle responded. "Now Jo, you've got to tell us how all this came to be. I mean, have you always been a crossdresser or was this something new? Are you bisexual, gay, straight? What's it like for you?"

"Alright, alright," I laughed in response. "Slow down and I'll try to answer all your questions. It all started with a bet..." I started off by relaying the details of my story...how Frank and Tom had basically turned me into their plaything, the things we'd done along the way, and how we'd come to meet Alex, Mark, Gina, and Elise. Chantelle and Maria listened with rapt attention, occasionally taking a sip of wine, laughing at times, and appearing to get aroused at others as they licked their lips at the images of me being skewered and caressed danced in their heads. Finally, I finished telling the facts of my experience and started delving into the other side...the emotional and psychological experiences.

"...It's been a real interesting experience. I never would have imagined that I'd find myself in this situation, let alone find myself enjoying it. But once I started to loosen up and go with the flow, it got to be quite a bit more enjoyable."

"So, now that you're here, what would you consider your sexuality to be?" Chantelle returned to her previous question. 

"You know Chantelle, I've been asking myself that same thing. The quickest answer is that I consider myself to be bisexual. But it's not necessarily that simple. The truth is, I think that I'm very much straight. When I'm in my day to day environment, I'm very heterosexual. I love women. I love being with them, talking with them, having sex with them, tasting them, loving them...I just love women. I walk down the street and imagine what it would be like to be with this one or that one. I also engage in very stereotypically male behaviors...I like sports, love technology, appreciate fast cars and motorcycles, and all that stuff." I paused to take a sip of wine and out of the corner of my eye, I noticed Charles listening closely while trying to appear like he wasn't being sucked into my story. "But when I'm dressed as a woman and hanging out with Frank and Tom, or Alex and Mark, I enjoy being treated like a woman. I was really uncomfortable at first because I was worried about being read as a man in a dress. But with Frank and Tom's urging, I started to go with the 'act', for lack of a better word. The more I let myself just relax and be treated like a woman, the more I was able to naturally emulate feminine behaviors, and the more a latent sexiness came out. I felt desirable...but in a different way from when I was in my 'masculine' mode. I saw other guys checking me out, and sure, some of them probably read me as a man, but nobody acted any differently. For the most part, I've been accepted and treated as a woman wherever we've gone. Granted, it's only been to a few places, but it's been good. And sexually, well...I'm not gonna lie. Being on the receiving end took some getting used to. I really struggled with it at first. But as I started to learn to surrender myself to the feelings and not get caught up in who was doing what to whom, I started to feel more pleasure. It's like I was given permission to be vulnerable, to be sexy, to be a woman. I stopped looking at things as 'being fucked by OTHER men' and started looking at it as 'being fucked BY men'. It was, and is, a subtle distinction but it works for me. I'm not necessarily attracted to guys, no more so than before...but when I'm dressed as woman, I can enjoy having sex with them. I just happen to be a woman with a little extra. I don't know...does that make any sense?"

I looked around at my audience and could see Chantelle and Maria nodding their heads. Even Alex and Mark seemed to understand what I was saying. Charles still looked skeptical, but if I understood correctly, he was going to have to get over it...or leave, I suppose.

"Here's another question for you Jo," Maria said. "Have you ever had sex with another woman while dressed as a woman?"

"Not yet I haven't," I replied. "Why, are you offering?" We all laughed.

"Maybe...probably," she responded. "I'm feeling a bit turned on...but don't want to go there just yet. Tell me, what do you think it would be like for you to have sex with a woman while dressed?"

I shrugged and said, "I don't know. I guess it would probably feel more like a lesbian thing to me. For some reason or the other, in my head, there's a real distinction between the male and female roles and the attire associated with each. I mean, if I were with another man who was also dressed as a woman, it would probably feel more like two women together than two men. Maybe it's just that societal double-standard that women can be affectionate, and we praise them for being bisexual, while men are limited in their options. Sorry guys." I winked as I said that and Alex and Mark laughed.

"It's okay, we understand," Mark said. "Actually, even for us being with you dressed as you are. We don't look at you and see a man in a dress. We see a woman...period. The fact that you still have a penis doesn't dissuade the image. It's just another part of you to be touched and played with."

Chantelle was nodding her head, almost unconsciously. Then she looked at Charles who had been silent the entire time. "Charles, what do you think? After everything that Jo just said...how do you feel about it?"

Charles looked startled by suddenly being the center of attention. He cleared his throat before answering. "I don't know Chantelle. It's a lot to take in. And my thoughts and feelings are two different things. I feel nervous. I think and wonder about my own sexuality if we go through with this. I admit, Jo you did an excellent job explaining things, although I'll probably have some other questions later on. Still, I like your conceptualization of sexuality. It's a good rationalization that, honestly, not everyone is going to accept. But I get it. And I can admit to some curiosity. Still," and he turned back to Chantelle, "are you sure this is what you want? For me to dress and be a woman?"

"Not all the time baby," Chantelle reassured him. "...Just sometimes. And I think that it will only enhance things between you, me, and Maria. It's not like we're out to hurt you. We do care about you and want you to feel included, but we...no, I need you to let yourself go. Let yourself feel things that will make our bedroom adventures sooooo much more enjoyable." There was a gentle pleading in her eyes that was echoed by Maria's. I got the distinct impression that Charles was not merely a boy-toy as Alex and Mark had suggested. He seemed to be more of a boyfriend who happened to be dating two lesbians. But with the opportunity to join them on an even deeper level, I didn't see how he could turn them down. I understood his angst though because, obviously, I'd gone through a similar process. What I thought was great for him, however, was that he was being given a choice as to whether or not he wanted to participate, whereas in my situation, it had been basically forced on me and I then chose to adapt to it.

I suppose my thoughts must have been written on my face because out of the corner of my eye, I saw Mark make a small gesture to Alex. Alex then turned towards me and put his hand on my shoulder. "Hey Jo, what's the matter?"

"Nothing, nothing," I quickly replied. "Just thinking about some things."

"What things?" Maria asked. 

"Oh, just...my situation," I said as I moved some strands of my wig behind my ear. "I guess being here and talking about everything and thinking about Charles' 'opportunity' has me thinking about some things that I want to discuss with Frank and Tom."

"Go on," Chantelle encouraged.

"Well, I was just thinking that one of the main differences between my experience and Charles' is that he's being given a choice, when my choice was really more of a forced decision. I don't know...I guess...I mean, I've adapted to the situation and even come to accept it and enjoy it. But still, I kind of envy you, Charles, because you're being invited to explore something different. You're not having it forced on you. I understand that you still may have some reluctance and whatnot, and maybe that's the challenge. Since I was kind of forced to do it, in some ways it made it more okay because I wasn't the one in control. If I did something that I wouldn't have otherwise done, I could always rationalize it and say 'I did it because they made me do it.' But for you, you're making a conscious decision as to where you want to go and what you want to do." I realized that I'd been rambling for a couple of minutes, so I tried to stop and pull myself together. "Just ignore me. I'll talk to Frank and Tom about 'my stuff' later on. For now, the question is to you Charles: what are you going to do? I promise that if you decide to go through with it, we'll try to make it as interesting and enjoyable for you as possible. So...?"

And with that, the attention was effectively shifted away from me and back to our star of the moment. Charles was faced with a decision that would invariably affect his life from this point on. We could all see the internal struggle that he was facing, but as I looked around the room, I could see that he was not the only one with stuff on his mind. Chantelle looked hopeful, as did Maria. Alex and Mark seemed to alternate between approval, curiosity, and resistance. I knew that they'd go for it though seeing as how they'd already enjoyed my pleasures and treasures. I think their reticence stemmed from actually being involved in the transformation process. Of course, for me, I was still coming to grips with what I would suggest if Charles said yes. Mentally, I was revisiting all the things that Frank and Tom had had me do and trying to modify those past actions to make them more...sensitive to Charles' situation. 




A Lost Bet Ch. 07



Finally, after a few moments of silent deliberation, Charles lifted his wine glass and took a sip to calm his nerves. "Okay. I'm in. I care about you two too much to not give this a shot," he said while looking at Chantelle and Maria. Immediately, they both started beaming and the mood in the room lightened significantly. 

"Now the fun begins," Alex surmised with a smile. "What should we do first?"

I jumped in and said "first things first...a shave. Ladies, why don't you handle that? That way you can decide how much hair you want to leave him with. Gentleman, you're with me...we're going back to that magic chest of yours to pick out a suitable outfit for Charles' coming out party." I clapped my hands and got a bunch of "yes ma'am's" and "yes sir's" from the comedians I was working with. There were smiles all around, and even Charles looked like he was getting caught up in the moment. I hoped he'd continue to feel that way as the evening progressed.

After the ladies took Charles off to the bathroom, Alex and Mark led me back downstairs so we could see what outfits might be available in the trunk. 

"Sorry, I forgot something upstairs," I said once we got down there. "Start pulling outfits out, but give me a minute to ask Chantelle something first." The guys nodded and I scampered back up the stairs.

"Chantelle, can you come out here for a minute?" I called through the bathroom door. I stood patiently waiting for her to stick her head out. Once she did, I asked "was there anything in particular that you wanted us to have ready for Charles? Any outfits you wanted to see or anything like that?"

She paused for a minute pondering how she wanted to answer the question. She glanced over her shoulder to watch Maria's efforts at shaving Charles and then turned back to me. "Something cute...like a sundress with a pair of flats...and a short wig, if they've got one." I nodded and shooed her back into the bathroom. With a smile of gratitude she turned and went back to the two loves of her life.

As I made my way back downstairs, I couldn't help but wonder how I'd gotten to be the de facto expert of feminization. The only answer I could come up with was that I was entrenched in it and the others were interested in my experience...and they trusted my judgment as to what would make the process easier and less traumatic than mine. I knew that I'd have to talk again with Frank and Tom about how this all came about. But that was a concern for another day. For today, it was time to help Charles get dressed.

"Alex, do you guys have a sundress, flats, and a wig that will fit Charles?" I asked as I got to the bottom of the stairs.

"Yep. At least to the sundress and wig. The only shoes we have are heels," Alex said.

"Well, I guess he'll just have to make do," I responded.

"Don't worry," Mark interjected. "It will all be fine." They dove into their chest to find the requested items, as well as a few items of underwear that he might want. "Actually, we were thinking about the bet and we have an idea for a photo that just might win the prize." 

"What's that?" I asked with blatant curiosity.

"It's a surprise," Alex whispered with a mischievous grin on his face. "But I'm sure you'll love it."

I started to respond when I heard the door open and Chantelle and Maria came downstairs leading a very naked, very clean-shaven Charles. He was wearing nothing but a towel, while the girls were wearing nothing but grins. As they reached the bottom of the stairs I asked him "are you ready Charles?" He nodded.

"Then step right up and see what's been laid out for you." I stepped back as Alex and Mark hammed up their display of the outfit.

"First," Alex said in a faux French accent, "we thought it would be nice if you started with a pair of pale pink, boy-cut, cotton panties and matching cami." He handed the lingerie to Charles who first took the panties and drew them up his legs. They fit quite snugly around his hips and nestled just a little bit into the crack of his ass. I slipped up next to him and whispered "you're probably going to want to tuck 'little Charles' between your legs for now. It will help the panties fit better." He paused and made a few adjustments, dealing not only with the first-timers discomfort of being tucked, but also being tucked in a semi-hard state. Next he took the cami and slid it over his head and arms. As he settled it around his frame, he looked pretty good. He wasn't muscle-bound to begin with, more lithe and sinewy, so the lingerie seemed to accentuate the softness of his frame...making him appear more toned and sensual. 

Mark jumped in next with an accent that was an obvious parody of someone gay. But he did it so well that we couldn't help but laugh (and I couldn't help but wonder if maybe he was telling on himself...you know, a little more gay than bi?). "The next thing we have for you is this lovely, flouncy, lavender sundress and matching 3" heels. You'll look FABU in this ensemble." We laughed at Mark's impression as Charles stepped into the sundress and slid it up and settled the straps on his shoulders. The change was amazing. His appearance was taking on a decidedly female form, especially once he stepped into the heels. I heard Maria whisper to Chantelle "My God, his legs are better than mine," to which Chantelle could only nod in agreement.

"Ladies," I asked, "would you be so kind as to help Charles with his wig and makeup?" They quickly agreed and settled him into a chair (not the same one that I'd been attached to) so they could get to work. They fiddled around getting Charles dolled up with just a little makeup...some lipstick, light eyeshadow and very little else. Finally, they settled the wig into place. It was kind of a dirty blond, layered wig that fell to right between his shoulder blades, and with his skin tone...it worked.

Chantelle stood back with a satisfied look on her face. "Ladies and Gentleman and everyone in between, may I present to you for the first time ever...Miss Charlene." And with that, a new girl had been born. Charlene stood up, a tad unsteadily, but turned to face the rest of us while Maria and Chantelle stood behind her glowing like proud parents. 

"Wow, Charlene..." Mark said with an appreciative smile on his face. "You look fantastic."

"I totally agree," Alex said after a short wolf whistle. "When you and the girls are doing your lesbian thing, somebody's going to have to keep track of who's who. You really do look...delectable." And if it was possible, Charles, now Charlene, appeared to blush a little bit. Shyly (and naturally too...what was that about?), she tucked a strand of hair behind her ear. 

"Jo," she asked. "What about you? What do you think?"

I paused, but only for a moment. "Girl, you've got nothing to worry about. Shoot, you look better than me." Everybody laughed because it was kind of true. "You almost look like you've done this before. But that's beside the point...at least for now. Here's my real question for you: How do you feel?"

Charles, now Charlene, stood there for a minute as she gathered her thoughts. "Well, I suppose you could say I feel...pretty. Being shaved is different...and maybe that's part of what I'm feeling right now. I have to admit, the panties and cami feel...soft...silky...and they make me want to rub something just to feel them slide across my body." We chuckled. "It's more than that, though. I mean, I would never have thought that I could look like this. I mean, as a guy...if I saw me walking down the street, I'd take notice. But it's still a little overwhelming. And Chantelle," she said as she turned to face the girls, "I'm not ready to go out like this, so get that idea out of your head right now." Chantelle had a fake wounded look on her face because she knew that she'd been caught.

"Seriously though, I'm actually surprised that I look as good as I do. I was worried that you were going to have me look like a man in a dress, but that's not the effect that I think I'm getting...at least not if I'm reading the looks on Mark's and Alex's face correctly." Alex and Mark winked at him and gave a couple of wolf whistles as if to emphasize her point.

"You do look really good Charlene," I said. "And I think you benefited from having two women with you who were committed to creating a complete image for you, even if it was to complete their fantasy. Now I imagine that after tonight, there will be some shopping trips down the road for you...but I'll let you fantasize about that on your own. I think the question on everyone's mind is...what do we do with the rest of the night?" We sat there staring at each other with silly grins on our faces while we waited for someone to make the first move. 

After a minute or two of people engaging in their own private visualizations, Alex spoke up. "Well I think that we should let Charlene get introduced to being a girl by another recent inductee...Jo, would you care to do the honors?"

"And what is it you'd like me to do?" 

"Start with a kiss. That's always a warm welcome," Alex suggested. 

I nodded and moved in to face Charlene...close enough to touch and leaving very little space between us. "Close your eyes," I whispered to her. She did and I moved in close enough for her to feel my breath on her neck. I let my arms reach up to caress hers, lightly running my hands from her shoulders down to her hands. As I took her hands, I intertwined my fingers with hers and moved to nuzzle her cheek. She stood motionless, but at each touch, I heard a small sharp intake of breath...almost a gasp. When I nuzzled her cheek, I felt her head move...turning to meet mine. Slowly and lightly our lips touched...gently at first, but with each passing second, the kiss became more intense. My tongue parted her lips to play tag with hers. And as our tongues danced together our hands came apart and pulled the other close. We kissed more and more passionately until soft moans were escaping from both of us. Finally, we separated and looked each other in the eyes.

"Well," Charlene said softly. "That was quite a welcome."

"Umm-hmmm," I echoed. "Just imagine what it will be like when Maria and Chantelle get their hands on you." 

"Yes," Maria called out. "We definitely want our chance to break Charlene in...the right way."

"What do you mean 'the right way'?" Charlene asked with a slight tinge of anxiety.

"Don't worry Charlene," Chantelle reassured her. "We'll save the toys and things for when we get home. For right now, we think the guys have a plan." And with a nod of her head, she directed our attention towards Alex and Mark. As we looked in their direction, we saw Mark with the camera capturing the whole experience so it could be relived whenever we chose.

"Jo, you remember that we still have a contest to win, right?" Mark asked. I nodded. "Alex and I came up with a plan...a position that should get us the win. Are you game?"

I was a bit nervous because I couldn't foresee what they might have in mind. "I suppose so. But what's involved?"

"Wait a minute," Charlene interjected. "What are you guys talking about?"

Alex decided to respond to Charlene's query. "Don't worry Charlene. You might be involved in this, but not in any way that should make you too uncomfortable. It's Jo that has the decision to make because this might be a little tough at first."

"Okay, now I'm getting worried," I said. "What are you guys talking about?" 

"Basically...a foursome Jo...and you're the center of attention," Mark said. "The challenge is going to be how much you can stretch."

I stood there for a moment and slowly, understanding spread over my face and my eyes widened as I grasped the full implications of what they were suggesting. "Wait a minute...you're telling me you want to fit two of you in my ass." They nodded slowly. I took a deep breath and pondered about what they were asking. Finally, I screwed on my resolve and said "O...K..."

To be continued...



A Lost Bet Ch. 08



"Don't worry Jo," Alex reassured me with a gentle smile. "We'll take it real slow. But you may want to start lubing up and doing your 'stretching' exercises."

"Yeah Jo, and we'd be happy to help you out," Maria chimed in. Quickly she came over and took one hand while Chantelle took the other. "Charlene, be a dear and grab some lube from over there near the wall." While Charlene went to follow Maria's instructions, she looked at me with a worried look on her face. I returned the look with a subtle nod indicating that everything would be okay. 

The girls led me over to the chest and got me settled over it like I was laying across someone's lap. Chantelle slid my skirt down my legs, caressing them lovingly all the way down. "You know you have beautiful legs. I could almost eat them up." Then she gave a quick kiss on each cheek before Charlene handed her the lube. Maria knelt down in front of me and gave me a deep tongue kiss, distracting me from the cold lube being spread on my ass. 

"Mmm," Maria intoned through our kiss. "You taste like strawberries." I smiled at that and returned her kiss with a playful nip. "Now are you feeling okay back there?"

"Yes, Chantelle has very soft hands," I replied.

"Okay, then she's going to start stretching you out," Maria started to describe what Chantelle was going to do and, out of the corner of my eye, I could see Charlene looking on with a mix of awe, nervousness, and a little bit of fear. "Jo, what Chantelle is going to do is use her hand, okay? Just nod." I nodded. "She'll start one finger at a time, until she can get her hand in there...then her fist, and by then, you should be plenty stretched for Alex and Mark, okay?" I nodded. "I'm going to stay right here next to you and if it gets to be too much or if she starts moving too fast, I just want you to squeeze my hand, okay?" I nodded.

I closed my eyes and started to lose myself in the sensations of Chantelle's hands on my butt. She wasn't rough in her technique...not that I'd expected her to be. But it's just, she was straightforward about getting her hand in either. She took her time with one finger, sliding it in and out, slowly, gently, and from different angles...tickling my prostate...curling the finger and pulling it out...every move measured against the reactions she drew from me. The thing was, she didn't just focus on her hands connection to my rear. With her other hand she caressed each cheek, sometimes running her hand all the way down my thighs to tickle the backs of my knees. It was such an odd sensation when she would do that with her fingers still inside me because I got confused about where I wanted to move to or how I wanted to move. When she added her second and third fingers, I couldn't help but moan. Unconsciously, I started to rock against her hand, but I gasped in surprise when I felt her bite my cheeks. I didn't think she drew blood, but the sensation set off sparks in my head. The spankings that she mixed in left me reeling and dizzy...not because they were hard enough to really hurt, but simply because the sensations came out of nowhere. I think I gazed out of half-closed eyes momentarily to see Maria smiling at me and licking her lips. I could still feel her hand in mine, but when I searched for her other hand with my eyes, I found it hidden in her own panties and I could see she was enjoying herself almost as much as I was. She gave a gentle squeeze when she saw me looking and I smiled at her. 

Apparently Chantelle saw our brief interaction and decided that I needed a little more...distraction, so she abruptly inserted her fourth finger into my rear eliciting an audible cry. Still, she didn't rush it after that. She gave me a few moments to adjust and wiggled her fingers just to hear my breathing get ragged. Slowly and methodically, she continued to slide her hand in and out, filling me...stretching me...making me feel sensations that I couldn't describe, only experience. As I got acclimated to her hand, I couldn't help but rock back and forth with her rhythm. But just when I thought that I had reached the pinnacle...that I could start to really relax and let myself go, Maria whispered to me "one more finger to go, then the hand...then she MIGHT let you come." I nodded as best I could and let myself slide back into that mental and physical cloud that was supposed to be carrying me to ecstasy. 

"Here we go," Chantelle said. And with that, I felt her pull out slightly and change her hand position so that all five fingers were teasing my sphincter. Her hand slid in until there was resistance...a silent "O" on my face the entire time...then as I relaxed, further and further in... Maria reminded me to breathe because I'd apparently forgotten to do so while focused on Chantelle's hand. Seconds seem to stretch into minutes and my ass felt fuller than anything I'd experienced thus far. Finally, the pressure eased and I could tell that Chantelle's hand was fully inside me. I could feel her moving her fingers around, and when she actually made a fist, I damn near cried. It seemed like every sensation I had was centered there. I didn't even feel the trunk under me. I was only vaguely aware of being pulled back from the trunk, guided by Chantelle's hand. 

"Open your eyes Jo," Chantelle told me. Slowly I opened them and as I did, I saw Maria positioning herself below me. She had stripped off her clothes (although I had no idea when she'd had time to do that) and had slid under me. Chantelle raised her hand and cantilevered me down to kiss Maria's welcoming mouth. As we kissed, I felt more movement near my groin. But it wasn't Chantelle's hand in my ass that I felt. It was her other hand stroking my penis... I'd been so focused on what she was doing to my rear that I'd forgotten I even had one. Slowly she stroked me, letting the silky softness and gentle touch of her hand massage me to a hard state. Maria and I continued to kiss and I started to lose myself again in a world of warm sensations that I had tasted over recent days, but had never really experienced before. 

Chantelle used her hand again to guide me lower, forcing my legs straighter until I started to feel a different warmth on the tip of my penis. It was then that I knew that she had positioned me right at the entrance of Maria's vagina. I could feel Maria start to shiver beneath me as my penis twitched against her labia and involuntarily jerked up towards her clit. As we continued to kiss, I could hear Maria moan lightly. 

As if that were a cue, Chantelle pushed her arm further into my ass, forcing me down and in to Maria's waiting embrace. An indescribable sound escaped my lips as I entered Maria. It had been so long since I'd been with a woman (instead of "being" the woman) that I'd almost forgotten what it felt like. But Maria's warmth...the way she fit me like a glove and used her muscles to clamp onto my penis...it was like riding a bike and I remembered the beauty of sexing a woman. 

I was still at Chantelle's mercy though. With her hand in my rear, she dictated the speed and pace of my thrusts into Maria. It's like she was using me as a dildo to fuck her girlfriend. Not that I minded. Each push and pull and squeeze and release elicited sounds from Maria and from me...sounds without words, but speaking of passion and excitement and feelings of pleasure. 

I thought that I heard the guys whispering something in the background but I had no clue. The focus of my world was being used by Chantelle and Maria...no, not used...accepted or included in the lovemaking experience maybe. I didn't know. I could barely think. All I knew was that I was enjoying one of the most fulfilling (and filling) sexual experiences that I'd ever had.

Chantelle changed her hand's position in my rear to put pressure on my prostate and I knew that I would not be long in cumming. Oh, the feeling of cumming inside a woman was something that had been too long in coming. From Maria's vibrations and moaning, I could tell that she was already well on her way over the brink of ecstasy. A few more seconds of Chantelle's pumping me into Maria and I was sent over the cliff as well...crying out...tensing up...shuddering uncontrollably...and tightening my ass around Chantelle's wrist. Until finally, I was done. Of course, Maria continued vibrating for a few moments, clutching onto my penis with her muscles like her life depended on it. Every little movement of Chantelle's hand in me caused me to move in Maria and set off a new round of fireworks for her (I think I actually saw sparks of color in her eyes when they rolled back in her head). 

As I lay there on top of Maria trying to catch enough breath for both of us, wrapped in Maria's arms, I felt pressure behind me. "Hold still," Chantelle said as she straightened out her hand and slowly removed it from my rear. "Did you enjoy that?"

I nodded. I tried to speak but apparently my voice wasn't ready to work yet. 

"Good, good," Chantelle said as she caressed each butt cheek. "Well, don't get too comfortable yet. I think the guys are ready for their turn."

My eyes snapped open at that. In all the pleasure for being with Chantelle and Maria, I'd managed to forget the original plan. "Do we have to do it now? Can't I just lay here with Maria for awhile?"

"No baby," Chantelle responded. "You probably ought to 'get your ride on' now while you're still stretched out and can accommodate them both."

Some of the nervousness returned, but it was overwhelmed by the warm afterglow I was feeling and the soft touch of Maria's hands on my back made me feel safe enough to go for it.

"Okay, okay," I mumbled from my after-sex haze. "Let's do this."

"Alright, gentleman?" Chantelle turned to Alex and Mark who had already taken off their shirts and looked like they were ready for action...if I was judging the bulges in their pants correctly from my vantage point.

"Here Jo," Alex offered. "Let me help you up...and over to the bed." Alex grabbed me by the waist and quickly got me into an upright position. I tried to stand up but found myself leaning on him because I couldn't trust my unsteady legs. He led me over to the bed where Mark had been getting situated. Mark was sitting on the edge of the bed when Alex surrendered me to him. He took me into his arms and gave me a slow, languid kiss. As he pulled me closer, he laid back on the bed, pulling me on top of him. As he continued to kiss me, I couldn't help but rub myself on top of him, letting my hands sneak up and play in his hair, while his hands caressed my legs and pulled them up until they were bent, one on each side. I felt him raise me up a little bit in order to slide his pants down to expose his erection. He settled me back down and I was able to feel his cock sliding through the crack of my rear. He stopped kissing me for a second. "Are you ready?"

"I am," and with no further words, he slid his penis into my stretched out rear-end. I was still able to feel him even though I'd been stretched farther than I ever though possible by Chantelle's hand. I placed my hands on his shoulders and levered myself up to a "riding" position. Mark put his hands on my hips as I got him settled comfortably in my rear. After a few up and down movements (and more than a few moans of pleasure from both of us), I indicated that I was ready to go for two.

"Well it's about time," Alex said. "Ya'll were acting like you didn't want to share." He crawled up on the bed behind me and gently pushed me back down on top of Mark. Mark was kind enough to grab both cheeks and part them so Alex could see what room he had to work with. The feel of his hands spreading me wide was...yummy. Still, I knew what was coming. I felt another pair of hands on my hips and knew that Alex was about to make his presence felt in a space that might or might not be able to accommodate him. 

"Here we go," Alex said. And with that, I felt Alex's cock fighting to slide past Mark's. "I'm going to add a little more lube...just to make things easier." The coolness was welcome as I enjoyed the heat and friction from Mark's penis and tried to relax enough to let Alex join in. Slowly and steadily, Alex pushed his penis past my opening.

"Ohh..." I didn't have any words as I experienced double penetration for the first time. The feeling was unlike Chantelle's hand because it wasn't just the width that I was dealing with, it was the contradictory movements as the guy's cocks slid past each other and moved around in an effort to get settled. If Alex moved, I felt sensations on one side, but if Mark moved, then I felt sensations on the other. And if they moved together...I experienced sensory overload. I think my eyes might have been open, but I wasn't sure. If they were, then I'm pretty sure they were rolled back in my head like Maria's had been. I won't say that it didn't hurt, at least a little bit. But if this was pain, then I was ready to be a masochist. Alex and Mark continued to jockey for position for a little while, eliciting grunts and moans and squeals (those were mainly from me) from all parties involved. Finally, after a few minutes of pleasure, they settled down so we could proceed with the next step of the plan.

"Charlene, why don't you take your place up front?" Maria suggested. I tried to refocus my eyes as I watched Charlene make her way over to the head of our bed. "Alright Jo, time for you to complete the foursome." Maria seemed to enjoy her newfound role as director. "Charlene, lift up your dress so we can see Jo sucking your cock." Charlene didn't hesitate to comply with Maria's suggestions and I didn't want to disappoint any of them, so I opened my mouth to enjoy my second taste of Charlene. 

Charlene stepped forward and slid her cock into my mouth while I moaned around the sensation. As soon as she got situated, the boys went to work. Alex and Mark started to pump in and out in and alternating fashion...never leaving me empty and leaving me confused about whether I was coming or going. Thankfully, with both of them holding my hips and waist, I didn't have to worry about which way I should be sliding. I was able to lose myself in the pleasure that they were generating inside my rear. I could tell that Charlene was enjoying watching me get fucked by the guys because she kept whispering "ohmigosh...Jo...that is so freaking sexy..." I responded by sucking with a little more insistency, occasionally switching up my technique and curling my tongue along the underside of her shaft as I tried to coax the cum out of her. 

"Jeez that's a helluva shot," Maria whispered. "Did you get it Chantelle?"

"Mmm-hmm," Chantelle murmured as she licked her lips with anticipation. "I'm just waiting for the money shot now."

"Did you hear that Alex?" Mark asked. "The girls are ready to see it all." (funny...his breathing was just a tad ragged) "Shall we give it to them?"

"Heh," Alex chuckled, "I'm ready whenever you are. Charlene, are you ready?"

"Oh God yes," Charlene stammered. "Jo is GREAT at sucking cock." 

"Will you look at that grin?" Chantelle asked. "I'd almost say that you like her better than me."

"No baby, that's not it," Charlene backpedaled. "You know I love how you do me, but I'd be lying if I didn't say that I really like Jo's technique."

"Fine, fine," Chantelle said with a smirk. "Are you ready? I think the guys are waiting on you."

"Yeah, if Jo keeps doing what she's doing, I'll be there in a minute," Charlene replied. Since that was all the encouragement I needed, I started going after Charlene's cum like it was the fountain of youth. I sucked with a little more force, tickling the underside of her shaft, moaning on her head, and trying every technique that I could imagine to send her over the edge. As my moans and my efforts got more enthusiastic, Alex and Mark started really taking advantage of their position. I could hear their grunts as they starting pumping in and out of my ass more aggressively, intermittently eliciting a squeal or delight from me as they hit spots I didn't even know could bring me pleasure. Seconds and minutes seemed to stretch into hours as I got lost on wave after wave of ecstasy...until...I felt Mark starting to tense up...then the first jet of cum filled my rear as Mark let out a grunt signaling the beginning of his release. As Mark continued to spurt cum into my rear, the activity spurred Alex's own climax and soon, both of them were shooting ropes of cum into my ass which was already filled to capacity. And to make sure that she wasn't left out, Charlene started to blow her load deep into my mouth and throat, quickly overwhelming my swallowing capacity. It didn't take long for the cum to start leaking out of my mouth and Chantelle made sure she got some shots of that. Then she quickly made her way around to get a close-up shot of Alex and Mark's cocks stuck in my ass with cum leaking from around them.

"Jo, I think you've got this little contest won. These shots are fantastic," Chantelle exclaimed.

I started to answer, but all that came out was "mmmpph...mmmm..." What I had been trying to say was "I can't wait to see them." But I knew I would have to try again after Charlene removed her penis from my mouth and I finished swallowing her gift to me. 

The collective hard breathing from Mark and Alex started to slow down as they recovered from their orgasms, and Charlene reached down to stroke my face as she looked at the world through half-closed eyes and twitching in her own post-orgasmic glow. "God Jo...that was a great blow job." 

Maria came up behind Charlene and started caressing her arms and chest. "Did you enjoy that hon?" Charlene nodded and I gave one final lick to her 'clit' as Maria pulled her from my space. I looked up into her face and saw her succumbing to Maria's ministrations.

"Were you enjoying yourself Jo," Chantelle asked. She'd come along side me and started to stroke my face even as Mark and Alex continued to lie there keeping me trapped in their sandwich. 

"Honestly...I did. I wasn't sure that I'd be able to do it...but it was...intense," I replied through my own warmth and glow. "I think I...oooohhh." My thoughts were interrupted as Alex, than Mark, extricated himself from my derriere. Their abrupt exit left me feeling empty, and more than a little weak. Chantelle continued to caress my face as the guys moved me over onto the bed and started to clean themselves up.

"Jo," Chantelle started, "I do want to say thank you for helping us all out. I think that whatever Maria and Charlene and I get into is going to be interesting and you are MORE than welcome to join us whenever we're in the same area."

"Hmm...," I hummed out through the contented smile on my face. "Thanks girl. I know ya'll are going to have lots of fun together. We've got to keep in touch." 

"Oh definitely," Chantelle said as she leaned down to give me a deep kiss...and lick off some of Charlene's cum that had dribbled down my chin. "You're amazing girl...and next time, I get to ride." She winked, gave a last caress to my face, then moved over to Charlene and Maria who were doing some caressing of their own. 

Mark and Alex came back to help me up, bringing warm washcloths to help me clean my face and dab at some of the gifts they'd left behind in my behind. 

"Oh...ok, as fun as that turned out to be," I squeaked out as I winced in discomfort, "I'm gonna be sore tomorrow." Alex chuckled as he ran a washcloth over and between my legs. 

"We're gonna get you some fresh panties and clothes to wear before we take you back to Frank and Tom," Mark said. "And a pad," Alex chortled. I wanted to be mad at him, but I couldn't help but smile since I knew he was right. I was going to have to do something about the leaking I was doing, but I didn't feel like inserting anything else back there for awhile.

"Alright guys," Maria called out. "It's time for us to head home. You've had your fun...hell, we've all had a great time...but it's time for us to get to bed." She walked over and gave me a kiss that rivaled Chantelle's. "Thanks chica...you're magnificent. Don't be a stranger, okay?" Then she moved out the way so that Charlene could say her goodbyes. 




A Lost Bet Ch. 08



"Thanks Jo. Having you here definitely made things easier." Charlene moved in for a hug and a kiss. "I'm sure we'll have even more fun the next time we get together."

"Oh you know we will," I responded as I gave her a tight hug and a deep kiss. "You all take care, okay? Be safe and have fun."

"Definitely," the three of them responded as they shared hugs and a few giggles and kisses with Mark and Alex. 

"Stay here Jo," Mark requested. "We're going to walk them out, then we'll come back and finish getting you cleaned up." I nodded and stretched out on the bed as I watched Mark, Alex, Charlene, Chantelle, and Maria head up the stairs. I listened to them gathering up clothing and coats and head out the door and spent a few minutes reflecting on how far I'd come in the last few days. 

I'd managed to do things that, a few months before, I never would have entertained. I'd become a woman in so many regards...and I'd come to like it. But I felt like I missed the male part of me. I wondered how I would feel though, once I was back in my male persona on a regular basis. I knew that I enjoyed the sexual side of things...being the woman...but I also enjoyed sex with women, and I still wanted to have a relationship with a woman. The question was, now that I'd been exposed to this new part of myself, would I find a woman who could appreciate it...kind of like Chantelle and Maria. Those thoughts continued to run through my head as I drifted off to sleep and dreamed of what was still to come once Mark and Alex took me back to Frank and Tom and Elise and Gina. 

To be continued...