The Halloween Wagerby49greg©
"Not so loud, but yes I did. I was younger then and I really wanted that position. I said as much to your father, and he joked to me that the only way I could win it now was to actually do a strip-tease."
"Dad said that?"
"He was a little tipsy even that early, and he was mostly joking. I looked him straight in the eye and asked if it was OK, and if he wanted me to."
"Don't stop now."
"He got sober very quick, and said it would turn him on. I went to the ladies room and added the tassels that came with the outfit and got in line. He was dressed as a thirties gangster, double breasted suit, fedora, that sort of thing.
"So I started imagining stripper music, I was about 5 people back from the other lady, and started slowly dancing around, slowly tugged one of my gloves off, danced some more as the line advanced, I think everyone was watching.
"When I got in front of the judges, and Miss McCardle was one of them, I stopped and put my foot on a chair and slowly peeled one stocking down."
"I would love you to do that for me some time."
"We'll see, but don't hold your breath."
"Is that all you did?"
"there was only a few people who wanted to do anything in the center after the parade, and I just waited 'till they were all done. I had put everything back on again, went out and started up.
"Your Dad had put a chair out there for me and I used it a little, I started with the gloves again, and eventually pulled my dress off, then my stockings, by then I was in the moment and pulled my bra off too, I was just standing out in front of more than a hundred people.
"But I wasn't nervous, I had these tassels on my nipples, they stuck to them and covered them, with a few inches of tassels hanging down. I had heard that old time strippers could twirl them and I tried.
"I couldn't get them to go at first, I was wiggling around like crazy, everyone was laughing and I was getting stage fright, then all of a sudden they started up, it was pretty easy once I got them going. It felt weird to have my boobs doing that though."
"That is neat. I wish Dad had taken movies!"
"Enough chit chat, it looks like things are starting up. Lets get in line at about the middle, looks like Sherry and her husband are waiting for last."
They got in line and dropped their capes, there was a coat rack there just so people could hang their coverings up. Ken heard some audible gasps as people saw them.
So far it looked to Ken that they were the most unusual couple there. As soon as they hung up their capes his mother got into her role.
"What are you doing there Sissy Slave, get on your knees!"
She gave him a quick slap on his bottom as soon as he was on his knees, the crop stung for a second but didn't really hurt through all the layers of ruffles and satin.
She pulled him and he walked a step behind her as she pulled on his leash. They slowly made their way to the judging stand. Some of the costumes were predictable, cowboys, dancing girls, a saloon girl was with a cowboy and obviously in the couples category.
There were many couples who were bride and groom, His mother said that they were actually two departments that were competing in their own private competition. There was a twist though, one department had all switched roles, the men were brides and the women were grooms.
There was a hula girl that was swaying and moving as she walked, several harem girls, and several Princess Leia costumes, all very revealing. Ken could see why it was an adult party.
Right behind them was a guy dressed up as Boba Fett in a costume that had seen better days, he was dragging another very curvy and well padded Princess Leia in a very revealing outfit, Ken kept trying to catch a glimpse of her because he thought the her top was actually just painted on.
Kathy kept tugging at his leash, and suddenly they were in front of the judges, she yelled at him, asking what he was, it was part of the script that they had gone over, he mumbled, she asked him to speak up, finally loud and clear he told everyone that he was a sissy slave that needed a spanking.
She pushed him down to his knees again, and then further so that his forehead was resting on the floor and his bottom up in the air, she flipped up his skirt, then his petticoat to reveal his satin frilly bloomers.
"All right sissy, you know what to do!" And she hit him with the crop, a lot harder than in practice. He yelped, then quickly:
"One! Thank you Mistress! May I have another!"
She obliged, and he got ten hard hits onto his bloomer clad bottom. It really hurt.
She dragged him up by his leash and he had to struggle to get to his feet in his high heeled shoes.
He couldn't help but admire his mothers' virtually naked bottom with the thin leather strap appearing from between her cheeks to meet the waistband of her thong just below her waist cincher.
She looked and acted like a real dominatrix, and he could imagine what she looked like doing a strip-tease right hear in front of all these people.
As they passed the Judges stand they heard gasps and some clapping, looking over at the beginning of the line they saw Sherry and her husband throw off the bed sheets that served as their cloaks.
Sherry was approximately the same age as his mother, mid forties, and like his mother she was blond and in very good shape, no doubt she worked out as often as his mother did.
Instead of a revealing costume, she was completely naked, Ken could see that she was completely shaved and her lower lips were bare. As he watched she was pulling on a very long blond wig that fell to her knees.
"Shit, she's lady Godiva!"
"And no body stocking." His mother looked harshly at him. "Mistress." He added then looked down to get back into character.
They finished the parade and went into the center 'stage' when it was their turn, Kathy kept up the harsh treatment. There was a chair there as a prop for whoever wanted to use it, and at the end she had him kneeling on the chair, facing backwards, his head bowed toward the floor.
She pulled up his skirt and then pulled down his petticoat and then his bloomers, showing his naked bottom, he had never been so exposed in his life, completely shaved, he was sure that anyone that looked closely could see his shaven balls and cock.
She started to spank him with her hand, he followed each blow by the count and the request for more. Between his spanks she caressed his bottom, she never did that in practice, her fingers several times slipped between his cheeks.
She finished up with ten more blows from the crop, ten more hard blows. As a finale she let him pull up the petticoat, but pulled off his bloomers. He had to step out of them and bend to pick them up. That wasn't in the script, but he followed every direction to try to win the competition.
Sherry's husband meanwhile had put on the horse head, it mostly rose from the back of his head, he bend over facing down, the horse head was then in the correct position, he had two front legs that held in his hands, they ended in hooves that he supported himself with.
So he was bent over, his back level and parallel with the floor, the extensions he held in his hands supported him and made his arms the same length as his legs.
Sherry, spectacularly naked, used a chair to sit on the sidesaddle strapped to his back. They made the circuit.
When she was in front of the judges she made sure that they saw all her charms, her performance in the center stage consisted of her riding her horse around in circles, her hair thrown back concealing nothing and her legs spread as far as she could and still keep balance.
After the parade she simply pulled on her bed sheet, but now instead of clasping it closed, she just knotted it around her neck, leaving her front unprotected except for the wig that was now mostly falling forward. When she extended an arm to hold a drink her sheet gaped open in front. She seemed to be perfectly at ease.
Kathy and ken stayed in costume as well, he without his bloomers, she with her buttock baring thong. Ken had to be careful not to bend over as his dress and petticoat barely covered his groin. He felt nervous, but somehow free, he could understand now how his mother dared to do a strip-tease.
The two couples completely ignored each other for the duration of the party. Finally about two hours after the end of the parade and all the performances all the awards were announced. The announcement for the couples trophy was held until the end.
Ken had spent the time drinking soda and following his mother around, fetching snacks and carrying them back whenever she asked. She mostly stayed in character and was usually holding his leash. Occasionally she would introduce him to a friend from work.
When the prize announcements started everyone gathered at the end of the ballroom where Mr. Gore and his wife and sister were standing at the table with the trophys.
Mr Reeve, the CFO for the corporation, was handing each trophy to Mr. Gore who in turn presented it to each winner. Mr. Reeve had a short fake beard on and was dressed in a dark blue naval officers uniform with ornate sword and a short imitation ermine cape and a crown. He told people he was King George the Fifth.
When it came time to present the three places for the couples prize, he called Sherry and her husband, Ken and Kathy, and a couple dressed as reverse groom and bride.
The groom would never pass as a man, although she came as close as possible, but the bride was very convincing, and could have passed as a woman under any but close scrutiny.
Mr Gore announced that instead of handing the prizes out in the traditional third place, second place, and first place order he wanted to hand them out as close to all at once as he could. He said that they were all very good and in any other year each could have one first place.
He went on to say that he knew there were some private bets placed, and that by handing out the prizes in the usual order it would give away the winner too soon. He then took the first place trophy, looked at each contestant in the eye, and then quickly handed it to Sherry.
Ken was stunned, his mother let out a breath as if she had been holding it in. Mr Gore then handed out the second place prize to Kathy and the third trophy to the groom.
Along with each trophy came an envelope, in Kathy's envelope were five fifty dollar bills. First place got five hundred dollars and third got two hundred.
Before they all left Miss Gore, dressed in her harem outfit, came over and congratulated each of the six finalists, when she got to Ken she put her arms around him and kissed him on the lips.
"I think you should have won, you make a wonderful sissy, especially since I think that without makeup and that costume it's obvious that you are such a handsome young man."
"Thank you." Ken tried not to stutter. When she had hugged him her barely clad knee had risen up between his legs and he felt it nudge and caress his cock and balls.
"I do hope we can meet again."
After that the three couples split up and Ken and Kathy circulated and accepted congratulations and condolences from many of her friends and co-workers. Kathy had another stiff drink.
Eventually they went to get their cloaks. Sherry intercepted them as they were leaving the ballroom. Her husband was no-where in sight. She was actually quite polite and friendly sounding.
She asked if they could talk on the way up to their respective rooms. In the elevator it was apparent that they were all on the same floor. She asked if she could come into their room.
Once in the room she sat down, her sheet still the only covering, and it was spread apart in front, she had taken on her wig and dropped it on the floor, Ken could hardly keep his eyes from her naked body, from her slim build with round, slightly sagging medium sized breasts and shaven slit with the inner lips just peeping out.
Kathy sat on the end of the single king sized bed in the room.
"I guess you want to discuss my weekend as your sex-slave." Kathy said in a low voice.
"Actually it's sex slaves." The emphasis on the plural.
"Sherry, look, he's my son, I told you my husband and I are separated."
"The bet said guest, not husband, not son. He's your guest to this party, he pays the penalty."
"But your husband, I know he's bi. If my husband was here, he could take it, but this is my son, he's never, he couldn't."
"He came, he pays. Did you know about the bet when you came here boy?" She looked directly at Ken.
"Yes ma'am. I'll pay up, whatever it takes."
"I like that, the 'ma'am', you've raised him well. We'll both enjoy the both of you."
Kathy was subdued, she had lost fair and square, part of her was thrilled, part of her was appalled.
"Of course," Sherry continued, "there might be a way we could work this out without my husband."
Kathy's head jerked up.
"What are you saying, don't jerk me around, what do you mean."
"Maybe I could be persuaded to leave him out of this, for consideration."
Kathy thought she was being teased, she was beaten, she was afraid it was all a ploy to raise her hopes and then dash them.
"OK, I'll bite, what do you want me to do."
"Some gratitude would be nice, and some enthusiasm wouldn't hurt."
Kathy knew she was being taunted, but there was nothing she could do, she knew that Ken would insist on paying the bet. Damn Halloween anyway!
"All right Sherry, thank you for sparing my son, I was stupid to bring him into this. I'll do anything I can to keep him away from your husband."
"It's going to be a multi-part deal. First, you hand over your prize money."
"OK, here." Kathy stood up and extended her hand with the envelope in it.
"Not good enough Kathy-slut, you're my slave, both of you are my slaves, I think you should both kneel and beg me to take the prize money."
Ken and Kathy exchanged glances, the 'Kathy-slut' hadn't gone unnoticed by either of them. They both got on the their knees in front of Sherry and bowed their heads, Kathy extended the envelope toward Sherry.
"Please kind mistress Sherry, accept our humble gift."
"That's better, that wasn't so hard was it. Now what I had in mind was to get this over tonight, maybe tomorrow morning depending on how much fun this is."
"Yes Mistress, we are yours for the night and into the morning if you want."
Instead of answering Sherry picked up the room telephone, she dialed her own room and told her husband to bring her bag, leave it at the door and knock.
They all waited, Ken and Kathy on their knees, Ken hardly able to keep his eyes off of Sherry's exposed pussy, he thought it was getting moist, he could just see some glistening. He also thought he cold smell her scent.
In a few minutes there was a knock on the door, Ken was sent to get a bag that was waiting on the floor in the hallway, he placed it next to Sherry and took his position on his knees. He realized that he was erect.
"I said it was a multi-part deal. First the money. Next, you both will be my slaves tonight, you will both do whatever I say. I can tell you now that at the very least you will both be satisfying me orally, and I've always wanted my ass licked, so one or both of you will get that honor."
Ken was thinking he would love to lick her pussy, he wasn't so sure of the other, but he'd do it. Kathy was resigned that she would be there as her son was having sex with another woman, or at least having oral sex with her.
"Then, in addition to whatever else I have you do, one of us, either you Kathy, or me, may end up fucking that sweet little sissy Ken here." She had an evil grin as she said that.
Kathy was shocked, she froze.
Sherry opened the bag and pulled out a strap on.
"Oh god no! Please Sherry, not that, not my little boy."
"It's OK Mom, I can take it."
"The question is Kathy-slut, do you want to gently take your son in the ass, or do you want to watch as I ram this thing into him, it's your choice." Sherry spoke in a sugary sweet voice as she held up the strap on. It actually wasn't that big.
Ken looked at it, He knew he'd had things come out bigger than that, if fact it didn't look as big as his erect cock. Still, this would be a big deal. His Mom, or Sherry. He knew Mom would be gentle as she could, but would she do it, did he want her to?
Sherry was grinning, she had come up with this plan weeks ago when her husband put his foot down and said that he wanted no part in humiliating Kathy.
She had purchased this strap on just for this occasion. Part of it fit into her as well as whomever she was going to fuck, and if felt really good. She convinced her husband to let her do him last night, she loved it.
"But first you too slaves need to get naked. Stand up and face each other!"
Ken couldn't look at his Mom as he stripped. She had recently seen him naked, and she was all but naked in that outfit, but there was something about getting undressed while someone watched that was unnerving.
Sherry was elated, both of them were knuckling under to her, she was so turned on she could smell herself. She was trying to introduced them slowly into what was her ultimate goal, but it was hard not to do it all at once. Get them used to obeying orders now, and later ... well later they would obey.
Kathy pulled off her bra first, she looked down at the floor, from the corner of her eye she could see Ken struggling with the back closure of his dress.
"At least unzip him Kathy-slut, what kind of mother are you."
Ken automatically turned and let his mother undo the hook at the neck and pull down the zipper. He pulled the dress over his head. He went to the hanger near the entrance to the room and hung it up, then returned as he pulled the camisole off his head also.
Kathy was sitting as she unzipped her boots and pulled them off. She was unhooking her stockings as Ken came back from hanging his dress, the sight of her topless, unclasping her stockings and rolling them down her legs was one of the sexiest things her had ever seen.
Kathy saw Ken drape his camisole over a chair, then he came over to her and turned his back.
"Mom, could you help?"
She unhooked his bra and handed it to him as he turned around, they were nearly face to face, she had one stocking on along with her thong and garter belt, he was only in the frilly petticoat/slip. Of course he still had the fake breasts glued to his chest.
"Go ahead boy, kneel down and help her with her stockings," ordered Sherry.
He did as she told him, he fumbled with the first fastener, figured it out and reached around to get the back on. As he reached around her thong was right in his face.
Seconds later he was rolling down her stocking. He put the rolled stocking with the other on the bed next them.
"Turn around Kathy-slut, let him uh-hook your waist cincher."
As she turned he noticed that the garter straps went under the straps on her thong. He reached up and easily unhooked the cincher, then pulled the straps out of her thong and she took the garment and placed it on the foot of the bed next to the stockings and the bra she had removed earlier.
She turned around and he was staring right at the thong covered pussy. He could smell the leather, but he could also smell her scent. Was his Mom also getting turned on by this. Was she truly the slut that Sherry called her?
"Pull it down sissy boy."
He reached up and slowly pulled it down, as it got below her pussy he felt resistance as it tried to free itself from between her butt cheeks where it had
As her son undressed her, Kathy became more and more aroused, she knew that he had been attracted to her for some time, she assumed that it was just the phase that most boys go through on their way to manhood.