The Bet

The six months had gone quicker than Sabrina, no Jon he had to remind himself, had thought they would.

He had expected Mistress Ashley to try to break him. Flaunting her power, teasing him, spankings, bondage sessions etc. All the things he, as a master, would have tried to do to her.

But she hadn't.

When they got to her house she gave him a quick tour, then brought him to his room, not a cage or a cell, a room. A comfortable room at that. A large bed, bathroom, a closet full of maids uniforms, granted they were all fetish uniforms, latex, leather, but even a few normal ones. There was a fully stocked makeup vanity. A selection of wigs.

"The wigs are only there until your hair grows out Sabrina," Ashley explained. "then we will get it styled for you."

There was a large screen TV on the wall. The room was more comfortable than most hotels he had stayed at.

"The TV has YouTube on it. You are responsible for watching videos on doing your makeup. I will not be training you." She said with a wave at the TV. "Pick a uniform, you will find panties and bras in the dresser. There are heels in the closet, I would suggest you start with the three inch heels until you are used to them. Unless, of course, you have worn heels before?" She smiled that cat-like grin when she said that.

Sabrina shook her head no, too overwhelmed to speak.

Ashley looked at him with a raised skeptical eyebrow.

"Get dressed, I will give you your list for tomorrow, tonight just wander and get used to your new home."

With that Ashley turned and left Sabrina to herself.

That's how the six months had gone. No sex stuff, no bondage stuff, just being her maid.

Now as they entered the last week of his sentence Sabrina was wearing six inch pumps. Her outfit was immaculate. Her makeup looked professionally done. Her nails were long, natural and painted a subtle shade of pink. Her hair was long, natural, and had perky curls.

Her Mistress called her into the private office. Waving her to a chair, Ashly watched as Sebrina adjusted her skirt and sat In a ladylike way with her legs crossed.

Ashley lit a cigarette and sat back studying her slave. She took a long sultry drag. Sabrina fidgeted a bit, her cock getting hard in her cage. This made Ashley smile.

After a silence that was becoming uncomfortable, on purpose, Ashly spoke.

"Well Sabrina, you have done well, better than I had hoped." Pausing to take another drag.

"Would you like a cigarette? We are just relaxing and talking. You can speak freely."

Sabrina thought about it for a moment, she didn't smoke but Mistress made it look so sexy and feminine. Maybe, but no, what was she, (he?), thinking?

"No Mistress, thank you."

"Suit yourself. I brought you in here to propose another bet. You don't have to accept it, you can finish your sentence and go back to being Jon."

She paused again to smoke.

So sexy Sabrina thought to herself. I wonder how a cigarette would look next to my freshly polished nails?

"This weekend The Queen of Hearts club is having the fundraiser party you tried to stop at the last council meeting you attended."

Sebrina felt shame at who she used to be, and blushed.

Ashly continued. "I think you like being my sissy slave, I think deep down you know this is who you want to be, Sabrina, not Jon."

Sabrina shook her head no. But wondered just the same at her Mistress's statement.

"So you say, but," Ashly continued, "Everything you are today, the beautiful looking lady I see before me, you made yourself. I provided the tools but you learned on your own to do your makeup. I never asked you to do your Nails, yet, there you are. I told you to wear 3 inch heels, yet here you are in six inch stilettos doing house work like a girl who grew up in heels." She paused to let Sabrina think about this. "But no matter, you think about it, come to terms in your own head."

Sabrina's well made up eyes went up when she realized everything Mistress said was true.

"No, let's talk about the bet I am proposing. As I said, this weekend is the fundraiser. I won't make you go in front of all your friends as my maid, I'm cruel, but not that cruel." She paused again to study Sebrina, surprisingly she didn't look relieved. Maybe even disappointed. "I want to revisit our bet from six months ago. My contribution to the fundraiser is going to be a glory hole box. There will be two holes, one slave in the box, you can do the math as to where the holes will line up. If you take the bet you will be tied up in the box, dressed however you choose. If at the end of the night you haven't cum, you will leave here with $100,000 in cash. If on the other hand you do cum, you will remain my sissy slave for as long as you want. Slave with benefits this time."

Sabrina started to open her mouth to say something. Ashley stopped her.

"There's more. My Aunt is coming back here, she doesn't Like Belize. So I will be moving into her home in Belize for the time being. If you lose the bet you will be going with me as a female. We will have your Passport and driver's license changed to female. We will even get you real boob's before we leave, if you want. I won't force a change like that on you."

Sebrina looked shocked this time.

"I know, it's a lot to take in. Take the rest of the day off to think about it. Tell me your answer in the morning."

"I will take the bet Mistress. But I want to make one stipulation. I want you to make the boob job a consequence of losing, I won't have a choice."

A smile crept slowly across Ashley's face.

Saturday, day of the fund raiser, 4pm.

Sebrina was decked out in her kinkiest black latex maids outfit. On her feet were thigh high boots. Makeup was on ten. Her lips bright, wet, red. Her hair tied back in a ponytail.

Mistress led her to a box. Stamped on the sides, in large letters,"Glory hole $250."

Mistress turned Sabrina to look at her. "I will let you out when you make me ten thousand dollars, slave." with that she took Sabrina's face in her hands and gave her a long slow wet kiss. Breaking the kiss she put a hand under Sabrina's skirt to feel her locked up cock. "What size boob's should we do slave? You're damp already."

Taking a condom from on top of the box, Mistress put it over Sabrina's cage.

"So we can tell you're cum from everyone else's." Ashley said with a laugh.

With that she nudged her slave to enter the box.

Sabrina did. As soon as she kneeled, Mistress passed several straps over her calves pulling her legs down into the box. Next a strap went around her waist pulling her back so her butt was forced up to the hole. Her hands went into mitts mounted to the inside of the box, the ties on the wrists were pulled tight trapping her. Mistress pushed her head forward until Sabrina's chin hit a padded shelf. A strap was pulled tight around her head forcing her lips to the hole. Finally the lid was put on the box and Sabrina was trapped.

She had been preoccupied with getting in the box and had not thought about what Mistress had said. Ten thousand to get free. That would be....40 uses, uses of her, uses of her mouth or butt.

"FUCK."She said, her words muffled By the side of the box.

She hadn't cum in over six months, there was bound to be some leaking with 40 uses, 40 loads bring deposited in her mouth or ass.

She had insisted on changing the terms of the bet not because she wanted breast's, but because she was afraid of going that far. She was tempted to go with Mistress and live like a girl for a while, she could enjoy that. But getting breast implants would make her a permanent girl, she wasn't sure she could deal with that. By making it part of the bet it gave her incentive to avoid cumming and take home $100,000.

Sabrina felt the box being moved from the storage area where Mistress had locked her in, to the main party floor. Then she was left alone for an hour or so. She started to rethink the last six months, what had she learned about herself. Who was Jon? Who was Sabrina?

The first cock entered her mouth and shattered her thoughts.

It moved gently at first, probing her mouth. Then it began moving faster, and deeper. It was long and started going down her throat. Sabrina quickly learned to breathe in rhythm with the movement, when her throat was open. Suddenly The cock began to pulse and fluid poured down her throat.

"He came in me. Oh my god, he came in me." started running through Sabrina's mind. Then a moment later,"Oh my god, I swallowed it!"

Before she could come to grips with that thought a cock slid into her ass. She had never been fucked in the ass but she had worn plugs before so the feeling was not unexpected. But this was so much better than a plug. The movement in and out, the pressure on her prostate, it was like nothing she had ever felt before.

Another cock entered her mouth as she was being sawn in half by the cock in her ass. She had to concentrate on the cock in her mouth, breathing in rhythm with the fucking. She didn't notice, at first, the building need to cum. The pressure built and built, until it was overwhelming. That's when she realized how much trouble she was in.

She tried to calm down as the cocks at both ends came and were replaced.

"I'm being spit roasted" she thought to herself. As she pictured her predicament, suddenly cum started flooding into her penis.

One last chance to stop it and save herself from.... from what exactly?

"I wonder how big Mistress will make them?" Was her last thought before her body was rocked by her first orgasm in six months. Being in a tight cage the cum didn't just spurt out. Her body felt the orgasm, but the cum came out afterwards, dribbling into the condom.

It was several hours later that she reached the goal of 40 loads. She had cum many times as well, the condom had long ago fallen from the cage, overfull, and lay in the bottom of the box covered in more cum. More cum leaked from her..pussy and ran down her thighs. Only her mouth was clean, she had swallowed every drop.

Her lips still looked perfect, thanks to the long lasting lip gloss she had applied. But the rest of her face was a mess. Between sweet in the hot box and tears as she dealt with her future being decided for her by her cock, she looked every bit the part of a party slut cum dumpster that she now was.

Mistress removed the straps, and helped her rise from the box. Once she was steady on her feet Mistress kissed her long and hard.

When they broke the kiss Sabrina was crying again.

"Sabrina, why are you crying?" Mistress asked, but before Sabrina could answer."You are still free to leave and go back to your life as Jon, I won't force you to stay with me."

"I came Mistress, I lost the bet, I am your slave as long as you will have me."

Mistress hugged the sobbing girl tight.

"Hoooo, hoo, how did you know this is what I needed?" Sabrina sputtered and finally got out.

"Because Sabrina, I loved you from the first moment I saw you. I knew the asshole you were projecting as Jon was a mask. I just needed to give you a chance to come out from behind that mask."

Sabrina sobbed more. And clung on harder to her mistress.