The House Always Wins
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James Smith was always on the move. His job demanded it, every week or so he found himself in some area of the world. It was tiring but enjoyable. He loved to travel and always made a point to take in as much of the local culture as possible. That almost always included finding a local casino and playing a few hands of blackjack. James fancied himself a somewhat decent gambler, although he never really understood the concept of counting cards he always seemed to find himself on the winning hand of most games of blackjack he played. He always looked forward to stopping at a casino after the meeting getting a drink, playing a few hands and leaving with more money in his pocket than he came in with.
It always hadn’t been this way though, when he first started out he found that he had a horrible time knowing when to quit and found himself spent, drunk and exhausted. After a few times of that he made sure to cut himself off when he was ahead. He never wanted to be at the mercy of the house again.
This week James found himself in the Big Easy, the city of New Orleans. He had been around here before and knew of a few small casino places, the river boat one was pretty nice but he had heard of a new place that was somewhat secretive. Apparently this place was a classy joint; high end drinks, amazing decor, well mannered gamblers and supposedly some of the hottest women you’d ever see.
After a few bits of detective work and one boring business meeting later James was off. After a little bit of travel he found it. It was down a small alley and a flight of stairs, not exactly what he imagined but he was in it to win it.
He took the stairs down and went through a door. Immediately any concerns he had vanished. This place was exactly as he had heard, definitely a classy place and hidden very well. He took a look around, quite a few people here and all sorts of games going on. There was a decent mix of men and women, he could tell he was going to have a good night here.
A hostess appeared in front of him, “Hello there, first time?”
“Yes, yes it is.”
“Glad to have you here this evening? What’s your game?”
“Blackjack.”
She smiled and beckoned him towards the back of the room, “Right over there.”
“Thank you.” James headed over to the nearest table and sat down.
———-
James was having an amazing night.
Hand after hand he had been beating the house and all the other players. He was on a hot streak but made sure not to let it get to his head. He kept his bets low and safe and the returns were stacking up.
As the night progressed James found himself surrounded by fewer and fewer players, it seemed that it had gotten late and many of the players had lost quite a bit of money. Soon enough it was just him and the house.
He was still cleaning up when a hostess walked up to him.
“Excuse me sir?”
James turned around, “Yes?”
“Could you please come with me?”
James suddenly seemed a bit nervous, was he in some sort of trouble? He hadn’t done anything wrong why was he being lead away?
“Is there some sort of problem”
“Just follow me sir, if you would.”
She moved her hand towards the back of the room where a large stairway lead to another floor.
James cautiously took his chips and headed towards them. The hostess slowly walking behind him.
He reached the stairs and slowly ascended them. The hostess still behind him.
After what seemed like a long time in James’s head the two reached the top. It was much like downstairs but a lot less crowded. There were a few tables with a small amount of people but things seemed more relaxed up here.
The hostess walked in front of him, “Right this way.”
She lead him over to another blackjack table where a well dressed man sat where the house attendant usually did. Around him were two other players; an Asian businessman and a southern looking man in a sharp white suit and cowboy hat.
“Please, take a seat where you wish.”
James looked over to her and then to the table. He walked over and slowly took a seat between the two.
The man in the house seat gave him a smile.
“Welcome, Mr. Smith is it?”
“Uh… ya… yes, but you can just call me James.”
The man chuckled, “Very well James, do not be worried, you’re not in any sort of the trouble, actually quite the contrary. I’m the owner of this casino and I’ve got to say you have quite a knack at blackjack. You’re not counting cards? Are you?”
“What? No, I have no idea how that works.”
The man smirked, “I figured as much, well no matter. I want to welcome you to the high roller room. It seems that your skill, or maybe luck, has warranted you a seat up here with some of the more riskier players.”
James smiled, “Well thank you sir but that wasn’t necessary, I just play for fun. I was just having a good night.”
“No need for modesty. Let me explain how this works, up here we play a little differently. It’s quite simple, you pick what you bet and we go from there.”
“I’m sorry, I don’t quite understand.”
“I’ll give you some examples, Mr. Katsumi here has requested his winnings in the stock of his company, Mr. Westin has requested tracts of land in Texas. You name what you want and if you get a winning hand you’ll win some of it. Although money is acceptable its a bit… boring. So James, what shall it be?”
“How can you possibly offer these as winning?”
Mr. Katsumi chimed in, “Yes, how is such an offer possible?”
“James if you would select your choice of winning I shall show you fine gentlemen.”
James thought for a moment.
“I’ll go with gold bars, it’s sort of money but its got almost a romantic feel to it.”
The man shook his head in agreement, “A safe, but classy, choice.”
The man snapped his fingers and another hostess walked out with a silver tray. She presented it to him. He pulled off two sheets of paper and a small gold bar, he handed it to them.
The three men were a bit surprised as they inspected their items. To their shock they were all legitimate. The gold brick in James’s was real, the paper in Katsumi’s hand was a genuine stock certificate and the paper in Westin’s hand was an official deed to an acre of land.
“Now gentlemen, I assume you are content with these?”
The three nodded and murmured their approval.
The man smirked, “Now I think we can agree that since you have chosen your option of winnings the house can do the same?”
Westin looked at him funny, “Now sir, I don’t know how you managed to do this. I’m not questioning it but surely you don’t expect us to be able to conjure up whatever it is you plan on choosing.”
“Mr. Westin don’t you worry, my choice will be fulfilled by me but supplied by you.”
“Come again?”
“Gentlemen I will be playing for your genders.”
The three of them all reacted with shock, confusion and a little amusement.
“Say what now? You’re not trying anything funny are you?”
“No, no of course not. Let me give you an example once more.”
He snapped his fingers and James’s hair immediately extended past his shoulders.
Katsumi and Westin looked over in utter shock and a bit of horror as James grabbed his hair unable to believe what had just happened to him.
The Man snapped his fingers again and James was back to normal.
“It’s quite simple and actually rather lucrative for you, every hand that’s lower than the house’s and you’ll change just a bit. But if you beat me, you’ll earn a little bit more.”
“I will not agree to such a bizarre and perverted choice!”
“Mr. Katsumi, gentlemen. Let me assure you that nothing bad will befall you. At the end of the night you either walk out with a little bit of winnings or a lot but you will walk out as you are now so long as you play fairly and enjoy yourself.”
“And why such a choice?”
“My reasons are my own.”
The three looked at him still a bit uneasy but slowly the three cautiously agreed.
“Very good! Now let us begin, and as a final note you are free to leave whenever you please winnings and all. However the moment you walk down those stairs you will be back to normal but you will not be allowed to reenter.”
The three nodded. The Man smiled and began dealing the cards.
———-
James looked at his cards. He had another good hand, seemed like his winning streak was holding up. He couldn’t say the same for Mr. Westin and Katsumi. Westin already had long blonde hair, a feminine face, slender arms and an hourglass figure. Katsumi was doing a bit worse, his hair had grown into a short layered bob hairstyle, his face had feminized, he had shrunken a bit, and James couldn’t tell but it looked like breasts had formed under his suit. The weirdest part though was he was talking in a high pitched girly voice.
The two of them seemed to be getting a bit uncomfortable but were still holding on.
James on the other hand had only lost one hand resulting in his hair again growing past his shoulders. However bangs had formed in the front now. It was a bit odd but certainly nothing that could throw him off.
The three played their cards.
James ended with a 20, Katsumi at 17 and Westin at 18.
The Man had 21, damn.
Immediately James felt his arms tingle, he pulled his sleeves up and saw that they were now hairless, smooth and feminine.
A new girly voice was heard beside him, “Ah damn.”
Westin’s voice had changed.
“Shit!”
James turned in time to see Katsumi raise just a bit in his chair, seemed that his ass had widened lifting him up just a hair.
“Bad hands, I’m sure you’ll do better on the next round.”
“Just deal already” Westin said.
After a few moments the three had once again called. James had 19, Katsumi and Westin 17.
The Man played until he had 19.
“Lucky hand James, sorry for you other two.”
Suddenly Westin went cross eyed, he opened his mouth wide and seemed to shudder in an odd way.
Katsumi’s clothing changed into a school girl’s clothing confirming James’s belief about his breasts.
Westin suddenly seemed very uncomfortable, he stood up “That’s it I’m out. I have to draw the line here. Sir, it has certainly been an interesting evening but I must retire.”
“Are you certain Mr. Westin?
"Yes sir I am.”
“Very well then, your winnings will be available to you at the bottom of the stairs. Goodnight.”
Westin turned around and walked away and down the stairs.
The Man turned his attention back to the two remaining players.
“Ready to continue gentlemen?”
Both nodded.
The next few hands were not the best for James, it seemed that his luck was running out. He had quickly found himself sitting on more cushioning below in the form of a larger ass, his legs were wider now and it seemed that he was lower to the table.
Katsumi had won a few but had lost a few as well. James had noticed that his legs had filled out a bit and in his last hand he had squirmed in his seat resulting in him giving off the same awkward expression Westin had shown before he bowed out. It wasn’t hard to tell what that meant, he was now a she.
“Another riveting hand however Miss Katsumi I regret to inform you that you have lost. There is nothing left for you to gamble and so must ask you to take your leave. Your winnings will be waiting for you at the bottom of the stairs. I hope you enjoyed yourself.”
Katsumi stood up and bowed, “It has been a memorable evening, I thank you for the stocks.”
The Man nodded, “Of course.”
Katsumi walked towards the stairs and left.
“Well James, it’s just you and me now. You certainly have proven to be the superior player. Shall we continue?”
James nodded as he looked at his new cards.
He quickly hit only to immediately bust.
“Damn”.
He looked down and found he was now wearing a very skimpy white dress.
“Very fitting I’m sure.”
James was getting a bit tired of this guy’s quips after every hand.
“Can we please do with less chat and more play?”
“Certainly.”
James came up with 19, The Man 20.
His face began to tickle as it suddenly morphed into a woman’s. He licked a part of his lips and tasted something strange. It took him a moment to realize he had lipstick on. That probably meant he had all sorts of makeup on as well.
As strange as this was getting he was determined to continue. He realized that regardless of him losing he would just be able to cash out when he was done changing. He could play all night if his hands were good. It was a no lose scenario, it would just get a bit awkward before then. He was prepared for it though.
He got another hand and ended with 18, The Man ended with 18 as well, alright a win!
The next hand he ended with 18 again, The Man with 19.
Immediately he heard snapping noises and saw that his midsection was now properly filling into the dress he had been wearing.
The Man dealt again. 20, 21. A loss again.
“Son of a…”
His voice changed into a very seductive one.
This may end quicker than he thought.
Another deal, a win!
Another deal, another win!
A third deal, a loss.
“Damnit he said in his feminine voice. He enjoyed the sound of his voice as weird as it was.
He felt an odd sensation in his chest. He looked down just in time to see two tits pop out and fill in the dress. The view was actually pretty nice, they were not too large but not too small.
"Pardon the intrusion but one more loss and it seems you’re done James.”
James looked up at him. “So it seems, I’m in this until the end.”
James was getting a little annoyed now though. He was kicking himself for losing so much, he knew he could do better. What happened to his hot streak he had been on only a short while ago?
A quick hand and James went bust.
He felt a small tingle in his groin, suddenly it grew in intensity. He shuddered as a wave of pleasure went through him. He couldn’t help but moan as he felt his penis shrink away.
“A shame James, I must say though that you had quite a good evening if I say so my-”
“No! I’m not done, I want to continue.”
The Man stopped and looked at him, somewhat amused.
“Oh? And what do you have to barter now? As I’m sure you just noticed you are all woman now.”
“I don’t know, um… make my breasts larger or something.”
The man suddenly gave off a devious smile.
“How about this, we go all in? If you win I provide you with enough gold to buy anything you would ever need. However if I win…”
James seemed a bit nervous but determined.
“…you change just once more and then come work for me, as you are now. I’ve recently had an opening and need a new girl. No questions, whatever I say you do, however you receive no winnings.”
“How long would I have to work for you?”
“However long you wish.”
What? Was this guy joking? However long he wanted? Fine, a day and that’s it, he’d be back to business as usual. But that was only if he lost, he had no intention of doing that, he was going to walk out of here the with enough money to last multiple lifetimes.
“I’m in.”
“Wonderful”
The Man dealt a him two cards, two tens. Damn this was perfect!
“Hold.”
He looked at The Man’s hand. A ten and a eight.
The Man looked up at him, “I hit.”
He drew himself another card and laid it down. A three.
21.
Shit that was it, he lost everything in a single card.
“I am so sorry Miss Smith but it seems that you have lost.”
Fuck, he had lost control, he couldn’t believe he didn’t restrain himself, all that money. He was going to be kicking himself over this for a long time.
“Yeah yeah…”
“Well Miss Smith, as per our agreement you shall begin work working for me… tomorrow.”
Another hostess appeared behind him.
“This lovely lady will show you to your room for the evening, I hope this was as fun for you as it was for me.”
James did his best to hide his frustration as he followed the hostess.
They went through a few hallways of doors. It sounded like there were other people in each room. He could hear laughter, cheering and what sounded like moaning. This place certainly was interesting.
The hostess stopped and opened a door and showed James in.
“Thank you for playing tonight miss, I look forward to working with you in the future.”
James gave her a patronizing smile as she closed the door.
James looked around the room, it was actually pretty nice. He quickly walked over and sat down on the arm of a dark couch on one side of the room. He looked down at himself and couldn’t help but laugh a bit.
Now that he was by himself and had a minute to think about everything that had happened that night he couldn’t help but question what had happened. In hindsight he royally screwed up, he had let his inability to control his gambling take over now he was stuck working for some unknown guy as some slutty looking chick. This train of thought eventually lead him to remembering that The Man had mentioned one final change. What did he mean by that? To his knowledge nothing had changed. This didn’t bode well.
James started to get a little nervous, what could it be? He didn’t even know what his job was going to be. He needed to get out of here and fast.
He looked up at the clock just in time to see it strike midnight. James suddenly felt a wave of ecstasy wash over him.
He could feel his breasts pulsating, he was warm all over. Suddenly his breasts grew four times their size. He braced himself by grabbing onto the couch.
He let out a moan, the pleasure he was having was beyond any kind of orgasm he ever had in the past. He attempted to close his eyes and handle the enjoyment when he heard the door opened.
“Right in here sir, she’s ready for you.”
James looked up in time to see a hostess let a man in. This guy was dressed like he had been plucked right out of 1986.
“Thank you babe.”
The hostess closed the door as the guy turned his attention towards James who was still trying to control the extreme feelings of pleasure.
“Why hello there, they said you were hot but I didn’t expect this. Why don’t we get right to it?”
He slowly approached James as he started taking his clothes off and letting them fall to the floor.
Through the intense feelings James was having he finally managed to figure out what was going on, he had become a hooker for this casino. Some back room slut here to entertain whoever could pay. No fucking way he was going to let this happen. He stood up only to have another wave of pleasure knock him right back down, only this time he fell back onto the couch and let out a moan.
“No words and it looks like you’ve already warmed yourself up. Damn you know how I like them!”
The guy was now completely naked, his erect cock pointed straight at James.
James couldn’t do anything but lay there trying to ignore the pleasure but it was just too much.
The guy jumped on top of her and like a pro unzipped the dress revealing James’s massive breasts and a pair of white panties. In no time he had them off too. James bit his lip at the feeling of the silk panties slide off revealing his new tight pussy for the first time.
Immediately the guy rammed his cock into her, she let out a scream of pleasure. This was too much for her. James couldn’t think straight. She was trying to keep her composure but the intense feelings only grew as she felt his cock push in deep. She had enough and zoned out.
As the guy thrust in and out he couldn’t help but talk himself up, “Yeah… yeah… you like that you bitch. What’s your name you slut?!”
James managed to blurt out, “James.”
“What have I fucked your brains out already? What’s your name you bimbo?!”
“Jamie!”
———-
The next morning Jamie woke up completely nude on the couch. Her panties and dress laying on the floor.
She could remember all the events from last night up until the guy coming into the room and… holy shit she was fucked by a guy last night! She looked down at herself, she was still a busty bimbo.
“Fuck me, I can’t believe that happened” she said to herself under her breath.
As she began to recall the events after the clock struck 12 she began to feel a little horny. As perverted as it seemed to James’s male mind that sex was the most amazing thing that had ever happened to her.
The door slid open. Jamie quickly grabbed her dress of the ground and covered herself with it poorly.
A hostess escorted The Man into the room.
“Ah, I see you were working quite hard last night? So… how was your first shift working for me?”
Jamie sat up and stayed quiet. She was too embarrassed to say that it was the greatest night of her life.
“Oh shy are we? That’s fine, Jamie is it now? Cute choice. Well I am a man of my word. The door is open, all you have to do is walk out and down the hallway. The second you exit the building you will be James again and can return to business as usual.”
Jamie looked at him and the hostess then at the door. She then looked in a mirror mounted on the wall on the other side of the room. She could finally see her new body in its entirety. She slowly removed the dress exposing herself.
She looked back at the door.
In a low voice she asked, “I’d like to stay and work for you… for a little while longer… if that is alright?”
The Man grinned, “Of course it is my dear! I have to be entirely clear though, I don’t take part timers. You have a week to try things out. After that you must choose, stay or go. Until then you’re on the clock, your next client is due in a few minutes. Enjoy!”
The two of them left the room, closing the door.
Jamie stood up and walked up to the mirror, she posed in various positions. It was turning her on.
Unaware of the time the door opened and another man entered, some business type. Jamie turned to him surprised by his arrival.
“Hello there sweetie, looks like you’re already ready for me?”
Jamie immediately began thinking about the sex from last night and wanted more. She dropped the dress she was still holding and headed over to him.
———-
The Man sat in a chair in front of a series of monitors. They were all security feeds from various parts of the casino; the regular floor, the high roller and the numerous private rooms holding all sorts of activities.
He pressed on a feed to Jamie’s room. She was on a bed on her hands and knees while a guy was ramming his cock into her. It looked like she was really enjoying herself. After a moment the guy pulled out and quickly went into the bathroom to clean up. Jamie lowered herself onto the bed but kept her ass up as if waiting for more.
The Man pressed a button and spoke into a microphone.
“It’s the end of the week. I’d like your answer now if you don’t mind. Should I be calling you James or Jamie from now on?”
Jamie reacted slightly from the sudden voice, she smiled.
“A bet’s a bet and although I had a bad hand I think I ended up winning regardless. So… you can call me Jamie.”
“Glad to have you on board Jamie.”
He released the microphone as the guy exited the bathroom.
Over the monitor he could hear Jamie.
“Done? Already? Are you sure I can’t interest you in another round, I’ll let you do whatever you want to me. No extra charge.”
The Man deselected her feed.
He smiled, “The house always wins.”
It always hadn’t been this way though, when he first started out he found that he had a horrible time knowing when to quit and found himself spent, drunk and exhausted. After a few times of that he made sure to cut himself off when he was ahead. He never wanted to be at the mercy of the house again.
This week James found himself in the Big Easy, the city of New Orleans. He had been around here before and knew of a few small casino places, the river boat one was pretty nice but he had heard of a new place that was somewhat secretive. Apparently this place was a classy joint; high end drinks, amazing decor, well mannered gamblers and supposedly some of the hottest women you’d ever see.
After a few bits of detective work and one boring business meeting later James was off. After a little bit of travel he found it. It was down a small alley and a flight of stairs, not exactly what he imagined but he was in it to win it.
He took the stairs down and went through a door. Immediately any concerns he had vanished. This place was exactly as he had heard, definitely a classy place and hidden very well. He took a look around, quite a few people here and all sorts of games going on. There was a decent mix of men and women, he could tell he was going to have a good night here.
A hostess appeared in front of him, “Hello there, first time?”
“Yes, yes it is.”
“Glad to have you here this evening? What’s your game?”
“Blackjack.”
She smiled and beckoned him towards the back of the room, “Right over there.”
“Thank you.” James headed over to the nearest table and sat down.
———-
James was having an amazing night.
Hand after hand he had been beating the house and all the other players. He was on a hot streak but made sure not to let it get to his head. He kept his bets low and safe and the returns were stacking up.
As the night progressed James found himself surrounded by fewer and fewer players, it seemed that it had gotten late and many of the players had lost quite a bit of money. Soon enough it was just him and the house.
He was still cleaning up when a hostess walked up to him.
“Excuse me sir?”
James turned around, “Yes?”
“Could you please come with me?”
James suddenly seemed a bit nervous, was he in some sort of trouble? He hadn’t done anything wrong why was he being lead away?
“Is there some sort of problem”
“Just follow me sir, if you would.”
She moved her hand towards the back of the room where a large stairway lead to another floor.
James cautiously took his chips and headed towards them. The hostess slowly walking behind him.
He reached the stairs and slowly ascended them. The hostess still behind him.
After what seemed like a long time in James’s head the two reached the top. It was much like downstairs but a lot less crowded. There were a few tables with a small amount of people but things seemed more relaxed up here.
The hostess walked in front of him, “Right this way.”
She lead him over to another blackjack table where a well dressed man sat where the house attendant usually did. Around him were two other players; an Asian businessman and a southern looking man in a sharp white suit and cowboy hat.
“Please, take a seat where you wish.”
James looked over to her and then to the table. He walked over and slowly took a seat between the two.
The man in the house seat gave him a smile.
“Welcome, Mr. Smith is it?”
“Uh… ya… yes, but you can just call me James.”
The man chuckled, “Very well James, do not be worried, you’re not in any sort of the trouble, actually quite the contrary. I’m the owner of this casino and I’ve got to say you have quite a knack at blackjack. You’re not counting cards? Are you?”
“What? No, I have no idea how that works.”
The man smirked, “I figured as much, well no matter. I want to welcome you to the high roller room. It seems that your skill, or maybe luck, has warranted you a seat up here with some of the more riskier players.”
James smiled, “Well thank you sir but that wasn’t necessary, I just play for fun. I was just having a good night.”
“No need for modesty. Let me explain how this works, up here we play a little differently. It’s quite simple, you pick what you bet and we go from there.”
“I’m sorry, I don’t quite understand.”
“I’ll give you some examples, Mr. Katsumi here has requested his winnings in the stock of his company, Mr. Westin has requested tracts of land in Texas. You name what you want and if you get a winning hand you’ll win some of it. Although money is acceptable its a bit… boring. So James, what shall it be?”
“How can you possibly offer these as winning?”
Mr. Katsumi chimed in, “Yes, how is such an offer possible?”
“James if you would select your choice of winning I shall show you fine gentlemen.”
James thought for a moment.
“I’ll go with gold bars, it’s sort of money but its got almost a romantic feel to it.”
The man shook his head in agreement, “A safe, but classy, choice.”
The man snapped his fingers and another hostess walked out with a silver tray. She presented it to him. He pulled off two sheets of paper and a small gold bar, he handed it to them.
The three men were a bit surprised as they inspected their items. To their shock they were all legitimate. The gold brick in James’s was real, the paper in Katsumi’s hand was a genuine stock certificate and the paper in Westin’s hand was an official deed to an acre of land.
“Now gentlemen, I assume you are content with these?”
The three nodded and murmured their approval.
The man smirked, “Now I think we can agree that since you have chosen your option of winnings the house can do the same?”
Westin looked at him funny, “Now sir, I don’t know how you managed to do this. I’m not questioning it but surely you don’t expect us to be able to conjure up whatever it is you plan on choosing.”
“Mr. Westin don’t you worry, my choice will be fulfilled by me but supplied by you.”
“Come again?”
“Gentlemen I will be playing for your genders.”
The three of them all reacted with shock, confusion and a little amusement.
“Say what now? You’re not trying anything funny are you?”
“No, no of course not. Let me give you an example once more.”
He snapped his fingers and James’s hair immediately extended past his shoulders.
Katsumi and Westin looked over in utter shock and a bit of horror as James grabbed his hair unable to believe what had just happened to him.
The Man snapped his fingers again and James was back to normal.
“It’s quite simple and actually rather lucrative for you, every hand that’s lower than the house’s and you’ll change just a bit. But if you beat me, you’ll earn a little bit more.”
“I will not agree to such a bizarre and perverted choice!”
“Mr. Katsumi, gentlemen. Let me assure you that nothing bad will befall you. At the end of the night you either walk out with a little bit of winnings or a lot but you will walk out as you are now so long as you play fairly and enjoy yourself.”
“And why such a choice?”
“My reasons are my own.”
The three looked at him still a bit uneasy but slowly the three cautiously agreed.
“Very good! Now let us begin, and as a final note you are free to leave whenever you please winnings and all. However the moment you walk down those stairs you will be back to normal but you will not be allowed to reenter.”
The three nodded. The Man smiled and began dealing the cards.
———-
James looked at his cards. He had another good hand, seemed like his winning streak was holding up. He couldn’t say the same for Mr. Westin and Katsumi. Westin already had long blonde hair, a feminine face, slender arms and an hourglass figure. Katsumi was doing a bit worse, his hair had grown into a short layered bob hairstyle, his face had feminized, he had shrunken a bit, and James couldn’t tell but it looked like breasts had formed under his suit. The weirdest part though was he was talking in a high pitched girly voice.
The two of them seemed to be getting a bit uncomfortable but were still holding on.
James on the other hand had only lost one hand resulting in his hair again growing past his shoulders. However bangs had formed in the front now. It was a bit odd but certainly nothing that could throw him off.
The three played their cards.
James ended with a 20, Katsumi at 17 and Westin at 18.
The Man had 21, damn.
Immediately James felt his arms tingle, he pulled his sleeves up and saw that they were now hairless, smooth and feminine.
A new girly voice was heard beside him, “Ah damn.”
Westin’s voice had changed.
“Shit!”
James turned in time to see Katsumi raise just a bit in his chair, seemed that his ass had widened lifting him up just a hair.
“Bad hands, I’m sure you’ll do better on the next round.”
“Just deal already” Westin said.
After a few moments the three had once again called. James had 19, Katsumi and Westin 17.
The Man played until he had 19.
“Lucky hand James, sorry for you other two.”
Suddenly Westin went cross eyed, he opened his mouth wide and seemed to shudder in an odd way.
Katsumi’s clothing changed into a school girl’s clothing confirming James’s belief about his breasts.
Westin suddenly seemed very uncomfortable, he stood up “That’s it I’m out. I have to draw the line here. Sir, it has certainly been an interesting evening but I must retire.”
“Are you certain Mr. Westin?
"Yes sir I am.”
“Very well then, your winnings will be available to you at the bottom of the stairs. Goodnight.”
Westin turned around and walked away and down the stairs.
The Man turned his attention back to the two remaining players.
“Ready to continue gentlemen?”
Both nodded.
The next few hands were not the best for James, it seemed that his luck was running out. He had quickly found himself sitting on more cushioning below in the form of a larger ass, his legs were wider now and it seemed that he was lower to the table.
Katsumi had won a few but had lost a few as well. James had noticed that his legs had filled out a bit and in his last hand he had squirmed in his seat resulting in him giving off the same awkward expression Westin had shown before he bowed out. It wasn’t hard to tell what that meant, he was now a she.
“Another riveting hand however Miss Katsumi I regret to inform you that you have lost. There is nothing left for you to gamble and so must ask you to take your leave. Your winnings will be waiting for you at the bottom of the stairs. I hope you enjoyed yourself.”
Katsumi stood up and bowed, “It has been a memorable evening, I thank you for the stocks.”
The Man nodded, “Of course.”
Katsumi walked towards the stairs and left.
“Well James, it’s just you and me now. You certainly have proven to be the superior player. Shall we continue?”
James nodded as he looked at his new cards.
He quickly hit only to immediately bust.
“Damn”.
He looked down and found he was now wearing a very skimpy white dress.
“Very fitting I’m sure.”
James was getting a bit tired of this guy’s quips after every hand.
“Can we please do with less chat and more play?”
“Certainly.”
James came up with 19, The Man 20.
His face began to tickle as it suddenly morphed into a woman’s. He licked a part of his lips and tasted something strange. It took him a moment to realize he had lipstick on. That probably meant he had all sorts of makeup on as well.
As strange as this was getting he was determined to continue. He realized that regardless of him losing he would just be able to cash out when he was done changing. He could play all night if his hands were good. It was a no lose scenario, it would just get a bit awkward before then. He was prepared for it though.
He got another hand and ended with 18, The Man ended with 18 as well, alright a win!
The next hand he ended with 18 again, The Man with 19.
Immediately he heard snapping noises and saw that his midsection was now properly filling into the dress he had been wearing.
The Man dealt again. 20, 21. A loss again.
“Son of a…”
His voice changed into a very seductive one.
This may end quicker than he thought.
Another deal, a win!
Another deal, another win!
A third deal, a loss.
“Damnit he said in his feminine voice. He enjoyed the sound of his voice as weird as it was.
He felt an odd sensation in his chest. He looked down just in time to see two tits pop out and fill in the dress. The view was actually pretty nice, they were not too large but not too small.
"Pardon the intrusion but one more loss and it seems you’re done James.”
James looked up at him. “So it seems, I’m in this until the end.”
James was getting a little annoyed now though. He was kicking himself for losing so much, he knew he could do better. What happened to his hot streak he had been on only a short while ago?
A quick hand and James went bust.
He felt a small tingle in his groin, suddenly it grew in intensity. He shuddered as a wave of pleasure went through him. He couldn’t help but moan as he felt his penis shrink away.
“A shame James, I must say though that you had quite a good evening if I say so my-”
“No! I’m not done, I want to continue.”
The Man stopped and looked at him, somewhat amused.
“Oh? And what do you have to barter now? As I’m sure you just noticed you are all woman now.”
“I don’t know, um… make my breasts larger or something.”
The man suddenly gave off a devious smile.
“How about this, we go all in? If you win I provide you with enough gold to buy anything you would ever need. However if I win…”
James seemed a bit nervous but determined.
“…you change just once more and then come work for me, as you are now. I’ve recently had an opening and need a new girl. No questions, whatever I say you do, however you receive no winnings.”
“How long would I have to work for you?”
“However long you wish.”
What? Was this guy joking? However long he wanted? Fine, a day and that’s it, he’d be back to business as usual. But that was only if he lost, he had no intention of doing that, he was going to walk out of here the with enough money to last multiple lifetimes.
“I’m in.”
“Wonderful”
The Man dealt a him two cards, two tens. Damn this was perfect!
“Hold.”
He looked at The Man’s hand. A ten and a eight.
The Man looked up at him, “I hit.”
He drew himself another card and laid it down. A three.
21.
Shit that was it, he lost everything in a single card.
“I am so sorry Miss Smith but it seems that you have lost.”
Fuck, he had lost control, he couldn’t believe he didn’t restrain himself, all that money. He was going to be kicking himself over this for a long time.
“Yeah yeah…”
“Well Miss Smith, as per our agreement you shall begin work working for me… tomorrow.”
Another hostess appeared behind him.
“This lovely lady will show you to your room for the evening, I hope this was as fun for you as it was for me.”
James did his best to hide his frustration as he followed the hostess.
They went through a few hallways of doors. It sounded like there were other people in each room. He could hear laughter, cheering and what sounded like moaning. This place certainly was interesting.
The hostess stopped and opened a door and showed James in.
“Thank you for playing tonight miss, I look forward to working with you in the future.”
James gave her a patronizing smile as she closed the door.
James looked around the room, it was actually pretty nice. He quickly walked over and sat down on the arm of a dark couch on one side of the room. He looked down at himself and couldn’t help but laugh a bit.
Now that he was by himself and had a minute to think about everything that had happened that night he couldn’t help but question what had happened. In hindsight he royally screwed up, he had let his inability to control his gambling take over now he was stuck working for some unknown guy as some slutty looking chick. This train of thought eventually lead him to remembering that The Man had mentioned one final change. What did he mean by that? To his knowledge nothing had changed. This didn’t bode well.
James started to get a little nervous, what could it be? He didn’t even know what his job was going to be. He needed to get out of here and fast.
He looked up at the clock just in time to see it strike midnight. James suddenly felt a wave of ecstasy wash over him.
He could feel his breasts pulsating, he was warm all over. Suddenly his breasts grew four times their size. He braced himself by grabbing onto the couch.
He let out a moan, the pleasure he was having was beyond any kind of orgasm he ever had in the past. He attempted to close his eyes and handle the enjoyment when he heard the door opened.
“Right in here sir, she’s ready for you.”
James looked up in time to see a hostess let a man in. This guy was dressed like he had been plucked right out of 1986.
“Thank you babe.”
The hostess closed the door as the guy turned his attention towards James who was still trying to control the extreme feelings of pleasure.
“Why hello there, they said you were hot but I didn’t expect this. Why don’t we get right to it?”
He slowly approached James as he started taking his clothes off and letting them fall to the floor.
Through the intense feelings James was having he finally managed to figure out what was going on, he had become a hooker for this casino. Some back room slut here to entertain whoever could pay. No fucking way he was going to let this happen. He stood up only to have another wave of pleasure knock him right back down, only this time he fell back onto the couch and let out a moan.
“No words and it looks like you’ve already warmed yourself up. Damn you know how I like them!”
The guy was now completely naked, his erect cock pointed straight at James.
James couldn’t do anything but lay there trying to ignore the pleasure but it was just too much.
The guy jumped on top of her and like a pro unzipped the dress revealing James’s massive breasts and a pair of white panties. In no time he had them off too. James bit his lip at the feeling of the silk panties slide off revealing his new tight pussy for the first time.
Immediately the guy rammed his cock into her, she let out a scream of pleasure. This was too much for her. James couldn’t think straight. She was trying to keep her composure but the intense feelings only grew as she felt his cock push in deep. She had enough and zoned out.
As the guy thrust in and out he couldn’t help but talk himself up, “Yeah… yeah… you like that you bitch. What’s your name you slut?!”
James managed to blurt out, “James.”
“What have I fucked your brains out already? What’s your name you bimbo?!”
“Jamie!”
———-
The next morning Jamie woke up completely nude on the couch. Her panties and dress laying on the floor.
She could remember all the events from last night up until the guy coming into the room and… holy shit she was fucked by a guy last night! She looked down at herself, she was still a busty bimbo.
“Fuck me, I can’t believe that happened” she said to herself under her breath.
As she began to recall the events after the clock struck 12 she began to feel a little horny. As perverted as it seemed to James’s male mind that sex was the most amazing thing that had ever happened to her.
The door slid open. Jamie quickly grabbed her dress of the ground and covered herself with it poorly.
A hostess escorted The Man into the room.
“Ah, I see you were working quite hard last night? So… how was your first shift working for me?”
Jamie sat up and stayed quiet. She was too embarrassed to say that it was the greatest night of her life.
“Oh shy are we? That’s fine, Jamie is it now? Cute choice. Well I am a man of my word. The door is open, all you have to do is walk out and down the hallway. The second you exit the building you will be James again and can return to business as usual.”
Jamie looked at him and the hostess then at the door. She then looked in a mirror mounted on the wall on the other side of the room. She could finally see her new body in its entirety. She slowly removed the dress exposing herself.
She looked back at the door.
In a low voice she asked, “I’d like to stay and work for you… for a little while longer… if that is alright?”
The Man grinned, “Of course it is my dear! I have to be entirely clear though, I don’t take part timers. You have a week to try things out. After that you must choose, stay or go. Until then you’re on the clock, your next client is due in a few minutes. Enjoy!”
The two of them left the room, closing the door.
Jamie stood up and walked up to the mirror, she posed in various positions. It was turning her on.
Unaware of the time the door opened and another man entered, some business type. Jamie turned to him surprised by his arrival.
“Hello there sweetie, looks like you’re already ready for me?”
Jamie immediately began thinking about the sex from last night and wanted more. She dropped the dress she was still holding and headed over to him.
———-
The Man sat in a chair in front of a series of monitors. They were all security feeds from various parts of the casino; the regular floor, the high roller and the numerous private rooms holding all sorts of activities.
He pressed on a feed to Jamie’s room. She was on a bed on her hands and knees while a guy was ramming his cock into her. It looked like she was really enjoying herself. After a moment the guy pulled out and quickly went into the bathroom to clean up. Jamie lowered herself onto the bed but kept her ass up as if waiting for more.
The Man pressed a button and spoke into a microphone.
“It’s the end of the week. I’d like your answer now if you don’t mind. Should I be calling you James or Jamie from now on?”
Jamie reacted slightly from the sudden voice, she smiled.
“A bet’s a bet and although I had a bad hand I think I ended up winning regardless. So… you can call me Jamie.”
“Glad to have you on board Jamie.”
He released the microphone as the guy exited the bathroom.
Over the monitor he could hear Jamie.
“Done? Already? Are you sure I can’t interest you in another round, I’ll let you do whatever you want to me. No extra charge.”
The Man deselected her feed.
He smiled, “The house always wins.”
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