The Bet
The Bet
Jon watched as she walked in like she owned the place.
That pissed him off.
It was the monthly meeting of the Queen of Hart's club. They were a loosely aligned Club of dominants that tried to keep the scene safe in their city. They held meetups and kink nights, the normal fare, but they also regulated the local dominants trying to make sure no sadistic basterds made trouble or hurt anyone, well more than they wanted to be hurt.
This was a board meeting, not open to the general members. There were five seats on the board, and sitting in one was a highly prized goal for everyone in the area.
That's what made Jon mad. Ashley hadn't earned her seat. Her aunt had, Ashley's aunt was well liked, respected, and feared in the community. But six months ago she had decided to move to Belize, and had given her house. Her slaves, and her seat to Ashley.
Ashley wasn't even from here, she moved in when her aunt left. No one even knew her before then.
Jon seathed.
It had taken him ten years of hard work to get on the board. Ten years ago Ashley probably was in Jr high, Jon thought. Now she was here, showing up late and making everyone wait for her.
The meeting started, and Jon found ways to argue with every point Ashley made. She even suggested a spring fundraiser that was actually a pretty good idea. But Jon shot it down and tabled it until a later date.
At the break. Ashley approached him.
"You don't like me do you Jon?"
"Ashley, I don't know you." Jon spat back, surprising even himself with the tone of it.
Ashley was the only one in the room not surprised. Others turned at his statement, waiting to see what came next.
"No you don't." she replied coldly "So you have no reason to hate me, yet."
Jon chuckled "Ashley, the respect you demand has to be earned, you have done nothing to earn my respect."
A smile spread across Ashley's face. "Are You offering yourself up for a chance to earn respect?"
Jon didn't see the trap that suddenly appeared before him.
"I've been a dom for many years, I don't think you could earn my respect"
One of Ashley's eyebrows went up.
In a slow sultry voice Ashley said "Want to bet?"
The room went silent. Jon knew immediately he had stepped in it.
"I'm not going to do a scene where you can tie me up and spank me." he said, quickly trying to get out of the trap.
Ashley just stared at him, letting him flail desperately.
Jon waited knowing to speak first was to lose, but also needing to extract himself from this spot he had put himself in.
"What do you have in mind?" he finally said, much weaker than he had intended.
Silence.
"So you have nothing, Ashley?" Jon said, finding some courage and feelings like he was winning.
"You sound like a petulant teenager Jon, stop talking." Ashley said, controlling the room.
"We will do a scene right here one week from tonight." She continued "I will not spank you, hurt you or fuck you in anyway. I wont even touch you sexualy. But if I win, you will be my slave for six months."
"So you won't be doing any sexual activity?" Jon responded.
"No, Jon, no typical Mistress activities. As a matter of fact I will be dressed in a sundress and flats, no latex or leather."
Jon couldn't believe his ears, "OK, but when I win you will be my slave for six months. How will we know who wins?"
"Simple, Jon, you will be wearing a chastity cage and a pair of panties. Nothing else. If, when we are done, your panties are wet, you lose."
"And if I'm dry, you become my slave?" Jon responded.
"Sentences don't start with 'and' Jon, but yes if that is you're counter to my bet, I accept." She said, correcting him and showing her control without him even noticing.
Turning to address the other board members she said "The members of the board will of course be judges, no?"
There were nods of assent but no one spoke.
"Well then, until next week." Ashley gathered her things and walked out.
No one talked for a minute, no one realized the meeting had never finished. Finally Jon broke the silence.
"Well, it looks like I will be training a new slave." He said with a slight laugh.
The other board members, still in shock from the events of the evening, didn't say anything, just started gathering their things and cleaning up the room.
One week later.
Jon was there. Under his clothes he wore his own chastity cage, as agreed. The keys he left at home. She had told him to bring them on a necklace for him to wear, but he didn't see the point.
The rest of the board were there as well, excited to see how this played out.
Ashley showed up late, fashionably. Dressed as promised in a sundress and flats, cute, but not sexy. She carried in a large bag and set it on the table.
"Ready, Jon?" She said with no small talk.
Pulling out a small bag she handed it to the nearest board member.
"A brand new pair of panties, please check them to make sure I haven't tampered with them" she said, taking control of everyone in the room.
The panties were passed around, the last person checked them and tried to hand them back to Ashley, she held up a hand.
"Give them To Jon," she said. "Jon, you strip and put them on."
Jon did as told.
Once done, Ashley stepped forward to inspect her victim. The panties were tight, showing a bulge over a tight cage. Ashley suspected he chose a tight cage to keep from getting a hard on. He was clean shaven from his eyebrows down as agreed upon in texts confirming the Bet. She also suspected this was his normal state, not something new for him.
"The keys, slave?"
Jon was taken aback by the slave comment, but decided he was that for the next hour, and he had agreed to it, so didn't argue.
"At home." he said
"At home, who? For the next hour, and perhaps longer, I am your Mistress and demand you treat me as such." Ashley said in a low dangerous tone.
"At home, Mistress." Jon replied.
"You may come to regret disobeying my command, slave boy."
Jon hated being called that and looked shocked.
"You are my slave for the next hour, as per the bet." Ashley said, her lips breaking into a smile.
"Now have a seat," she said as she shoved one of the desk chairs his way. "We said no whips and chains, but do you mind if I use my scarf to gently tie your arms to the chair? Only with your consent of course."
He thought for a moment, and agreed to this.
She slid a scarf off her neck, it turned out to be two scarfs, heavily perfumed. She passed them under his nose before kneeling down to loosely tie his wrists. They smelled beautiful, feminine, and sexy.
Next she took a makeup kit out of her bag, it looked like a tackle box for fishing, a big one. She opened it and pondered for a moment. Selecting the color foundation she wanted she went to work.
"Wait, what are you doing?" Jon asked.
"Makeup??" the sarcasm heavy in her voice. "You agreed to anything outside the traditional bondage and pain of our normal day to day scenes. Judges, do you agree this is allowed?"
There were some murmurs. Finally one of the board members said yes she could continue.
With a sponge and a brush in hand she started applying the foundation. She covered his whole face, out to his ears and even down his neck.
Jon wouldn't admit it but this was a bit of a turn on for him. The attention, the feeling of the brushes. He had to be careful though and not get too excited.
Ashly continued on, contouring, blush, eye liner, eye shadow, lashes, and even contoured his brows.
As she went, Jon fell deeper and deeper into her spell.
Finally she felt she was done.
Going to her bag she pulled out a wig. It took her a few minutes to adjust it, then she stood back.
Sitting down, she took a cigarette from her bag and lit it.
"You can't, ah, you can't smoke in here." One of the judges spoke up.
Ashley turned and glared at him, he backed down.
Jon watched her, mesmerized as she took a long drag and held it. Then blew the smoke at the ceiling. Unknowingly Jon licked his lips, making the red lipstick shiny and wet looking.
"You will learn to make yourself up like that on your own as my slave, Jon." Ashley stated with authority. As if it was a done deal.
Jon nodded agreement without really hearing her words.
"Jon, Jon, Jon. That doesn't sound feminine. You are going to spend the next six months as my French maid, you need a proper name. Joan would be easy for you, but I think you look more like a Sabrina to me." She mused, as if the bet was won.
"You can cum now Sabrina." Ashley ordered with authority that enveloped everyone.
Jon did, soaking his panties, not even realizing how hard he was in his cage. His eyes went wide and he mouthed "no". He was her slave. Six months. No.
"Judges, do you need to check?" Ashley asked, a smile on her face, as she stubbed out her cigarette.
One of the judges let out a laugh and said, "No you've proved your point, you deserve his respect, and frankly all our respect. If I never said it before, welcome to our club."
Getting up she started to clean up, once her bag was packed, she took her scarves back off Jon's, now Sabrina's, arms and told him to get dressed, they were leaving.
Turning she addressed the judges.
"I trust you can get his car back home?"
"We will take care of it Mistress, would you like us to bring his chastity keys to you?"
Ashley laughed, "No, he gave himself a six month chastity sentence, I will hold him to it."
Turning to Sabrina, she said. "Come slave, you have a maids outfit waiting, and work to attend to."
Sabrina, still in shock, followed her mistress out into the night and six months of servitude.
- During the heated discussion, Jon suggested that Ashley could prove her dominance by organizing a charity event without involving any BDSM elements, a suggestion that was met with silence in the room.
- After the meeting, as Sabrina, Jon found himself performing household chores under Ashley's stern yet forgiving gaze, his chastity cage barely allowing any relief from his growing excitement, a stark contrast to his previous life as a dominator.