The Halloween Wager

This story is a complete fabrication and any similarity to any person living or dead, or any event is a coincidence. All characters are over 18 years of age. The plot is a fantasy or an adult nature and includes sexual acts that may or may not be legal or pleasant in real life, if any adult story offends you, don't read it. If you are not of legal age of consent in your area, don't read it. Have fun.

Ken -- Our Hero

Kathy -- His Mom.

Sherry -- Kathy's nemesis

Ken was running late, He was in his first semester at the local Community College. His plan was to save money for his first 2 years of college, then he could afford to go to a better school for his Bachelor's degree.

His last class on Friday usually let out ten minutes or so before the bell, but this instructor, know by the student body as "Mr. Mumbles", had kept them over the full hour. As a result he was late getting out.

Then the instructor wanted to talk to him about his research paper, he didn't like the progress Ken had made on the bi-weekly report he had turned in on Monday, he had to go with the professor to his office for twenty more minutes. When he finally got to his car he had a flat and had to change the tire.

It had capped off a frustrating day. Classes seemed to drone on, he couldn't concentrate on the lectures, parking was a problem everywhere on campus so he had parked in the furthest lot from his last class.

His Mom had kept nagging him to get a costume for her company Halloween party all week, and he kept putting it off. The last few days she had augmented her evening and morning nags with texts, all day long.

So for Friday she had insisted he come straight home and they would go to a costume shop for their costumes.

The party should have been next Wednesday night anyway, that was Halloween. Then he could argue that it was a school night and he would have to come home early, and why the heck did he have to fill in for Dad anyway, and why did Mom and Dad pick this time to split up now anyway!

It wasn't like they were divorced, they were just separated, people got back together didn't they, couldn't Dad take her? Mom said no, and when she said no she always stuck by it.

And what was so important about this Costume party anyway? Her company had parties all the time, summer picnic, Thanksgiving, the Christmas party was in early December so it wouldn't interfere with real Christmas parties, there was something in Spring, and of course the New Years Eve party was legendary.

When he and Kellie were little they had wanted to go the Halloween party but Mom and Dad always said it was for grown-ups. He wasn't sure what she meant by that even now.

One thing was sure, and that was that Mom was going to go ballistic when he finally showed up. She had stopped texting and that was a bad sign. When he finally got home she didn't say anything just hustled him into her car and they left. A worse sign.

On the way she finally let him know why it was so important. She had made a wager with a coworker. It had sounded to Ken if she had been suckered into a bet because he knew she didn't like Sherry, he had heard her name often enough, often preceded by the words "that bitch".

The bet had been made before she and Dad had separated and involved some sort of penalty for the looser. The winner was the couple who won the best couple costume. Up until now Ken had not realized what a big deal the company costume party was.

"Ken, I'm sorry I've been so bitchy, I assumed that since your Dad and I are separated the bet would be off, but this morning I found out that the written bet that we made just mentioned guest, not husband."

"You've been wanting me to go all along."

"That was just because I didn't want to go alone, It was going to be fun, but now I've got to honor that damn bet I got talked into and we better win, I put your name down as my guest a few weeks ago so it's got to be you."

"So we have to get matching costumes? What does that mean?"

"Well, for instance, if I went as lady, you would be a knight, something like that. But I want something spectacular, something that can't loose."

"Like what?"

"I don't know. We'll see when we get there."

"What's this bet for anyway, a few bucks? Dad would help out if you wanted wouldn't he?"

"No, it's not money, it's something else. I can't tell you."

"It's OK Mom, I'm over eighteen, I can take it."

"I just don't want to loose, we can't loose."

"Well, if we win, what can I expect?"

"If we win I was just not going to insist that they go through with it, and that bitch Sherry knows it."

"If I'm involved, I should know."

"Here we are, we'll discuss this later."

Kathy was worried, the store was well known, it sold party supplies all year and always had a small selection of costumes, but at Halloween they brought in huge amounts of costumes for sale and rent. But the parking lot was nearly empty.

They found out why when they got in, as the walked into the area where the costumes were kept, they saw that very few were left, and as they walked up and down the two aisles they couldn't find anything they liked.

When Kathy asked the sales girl, she was told that the truckload of costumes they had ordered had been in an accident and wouldn't be arriving. While Kathy was talking the owner of the store came up.

He gave her the name of several department stores, a couple of thrift stores, and even the other costume shops in the city that might have something at this late date, but none of them would have the range of costumes that this store was noted for.

"But we have to have a pair of killer costumes, so much is riding on this."

She went on to tell him that she had made a bet with a co-worker for some high stakes, and that the company party was on Saturday.

"It's very unfortunate I know, but nearly everyone is having a party this weekend, and even the official trick or treat for children is this weekend. This disaster is very bad for us as well, we usually make a great deal of profit."

By this time the sales girl, a high school girl that Ken had seen around his high school before he graduated, had left to wait on someone else.

"There is one other place that I know of, you might have to buy the costumes, and they aren't cheap, and they certainly aren't for the faint of heart."

"What ever you have to suggest. I should have come earlier or made them myself, but ... well we didn't so here we are."

He took out his business card, wrote something on the back, and gave it to Kathy.

"I will call and let them know you are coming. Ask for Ms. Kent, she is the owner and will do what she can, but I warn you, the costumes are not ordinary in any sense of the word."

Kathy thanked him and as they left he took out his cell and made a call.

When Kathy and her son were in the car she looked at the card and keyed in the address to her GPS.

"Madam Kent's Boutique Exotique, Kathy read from the card. I wonder what that is?"

"Sounds kind of sinister to me." Ken said.

They found their way following the GPS directions, Ken was looking at the street map as well. It was in an older section of town, not exactly run down but at best it was well worn.

Madam Kent's boutique was in a brick building that had two stories, and looked as if I might have been a hardware store or some sort of small specialty store at some time, perhaps sixty years ago.

The building itself looked well cared for and the signage was discrete and well made, one could almost take it for a high end ladies dress shop. As they entered a bell over the door tinkled.

Once inside they found a well ordered rack of what looked like dance costumes on one side, and uniforms on the other, further back were some mannequins dressed in outfits that looked like belly-dance costumes.

A tall woman with black hair pulled back into a severe bun came out of the back of the store.

"Yes, can I help you?"

"Are you Ms. Kent? Mr. Hollies at Hollies Costumes and Party Supplies sent us here, he said that he would call...."

The lady smiled, "I am Ms. Kent, so glad that you came, I understand that you are in need of a prize winning costume?"

"Yes, you see at a company party, I made a foolish wager with a co-worker that we would win the couples costume prize."

"I understand, I know how these things can lead to all kinds of work-place rivalries. I hope you hadn't been drinking when you made the bet?" She made a soft laugh as she said that.

"Actually we had, just some of us stopping for drinks after work, that's the worse part. My co-worker and I don't get along and she would definitely want me to pay up."

Ken was intrigued by this commanding woman and hadn't made a sound so far.

"And who is this beautiful boy? Surely not your husband?"

"No, it would still be bad if my husband was there when we lost, but we, uh, we are temporarily separated, and my son has to fill in, so you see I can't lose." Kathy was blushing, and Ken was more puzzled.

Ms. Kent seemed to catch on, even if Ken didn't.

"We aren't really a costume shop in the ordinary sense, but out here we have some things that we could make into a couples type costume. A Cheer Leader's outfit, I'm sure you could find a football uniform for your son."

"I'm not sure...."

"Or a harem dancer, we could find something to make him look like a sultan?"

"No, I really need something with, with ... zing."

"We have an area in the back, not your usual thing, I must insist that your son be over eighteen."

"Yes, he turns nineteen in a few months."

"These things are quite expensive, if you like I can arrange a payment plan, and of course we accept all the major credit cards. But they are more in the way of being, well, fetish items."

Kathy hesitated, she had suspected that was what Mr. Hollies had hinted at, but she had to win.

"Lets see them."

Ms Kent went to the front and flipped over the open/closed sign and walked back past them.

"Follow me then. It is close to our normal closing hour as it is and my assistant has already left"

Ken thought that Ms. Kent had beautiful hips and her bottom was very round and he could hardly keep his eyes off of it as she worked each hip and cheek with every step. The close fitting skirt and high heels certainly helped.

Ken couldn't help compare Ms. Kent with his Mom. Kathy wasn't as tall, but since he became interested in girls, Ken had thought of his Mom as a really sexy. Most of the time she projected an image of an innocent but pretty housewife, but when she got angry she could be very severely sexy.

They went through a doorway into a smaller room, it had some mannequins dressed in an assortment of sexy leather lingerie, some deep shelving along one wall that seemed to be filled with clothing or costumes of some sort. The lighting was subdued. A fitting area with mirrors on three sides of a raised dais, and several cabinets completed the room.

"Now Mrs. ...?"

"Vaughn, Kathy Upstell, and this is my Son Ken."

"Very pleased to meet you, I am Rona Kent. Please call me Rona."

Rona looked at Kathy for a second and then Ken before continuing.

"Kathy, I see you as basically a dominant person. With your looks you would be very striking. If you prefer we can fit you into a more submissive type of costume, but I see you in black leather, perhaps Red."

"Oh, I don't know, what do you have if I was more submissive?"

"There are a variety, if it is a more adult party perhaps a series of leather straps, and a collar, we could leave most of your, ah, private areas, bare of course."

"I'm not sure about that."

"We have something on the order of a slave girl, something that would be similar to a Princess leia type thing, it wouldn't be as conservative as that of course."

"Oh, well, I'm not sure."

"I really think you should dress more dominantly, come with me, Ken, you can sit over there."

She went to what looked like a huge walk in closet, selected a few things and took his mother into a fitting room.

Ken heard a few gasps and an "oh my!" and even a giggle from his Mom. Eventually she came out.

"Ken, you are not to talk about this with ANY of your friends, or your father."

Ken could only gasp.

His Mom was wearing some king of black waist cincher a leather bra that barely hid anything, black leather bikini panties, black stockings that were held up by garters hanging from the waist cincher, and her sensible flats.

She stood on the platform and turned from side to side and completely around as she looked at herself. Kent just stared and tried to keep from getting erect.

Ms. Kent came back with some high boots and what looked like a riding crop. Ken had a straight on view of his Mom as she sat down across from him and put on the boots. He could see a zipper seam down the front of the panties clear down past her crotch and up the back.

Kathy stood up and she zipped up one boot while Rona did the other. Rona took the riding crop and slid it down the top of one boot. The boots had four inch heels! They came nearly as high as the stocking tops.

"We can get higher heels if you like, but if you're going to be on your feet for very long these are better."

"I think these will be fine." Kathy had a glow about herself, she couldn't stop looking at herself. Ken had an erection. He crossed his legs to hide it.

"I think I can find some higher stockings, you can adjust the garters up, that way they would show more above the boots."

"Higher than these?"

"Yes, I have some that will come nearly to your pussy."

"Yes, I think a few pair of each size, I can try different ones at home and see what I like."

"Here, this will be good too."

Rona added a studded leather collar as well. Then stood behind Kathy and pulled her hair back and held it as if it was in a bun.

"That will look more severe. And your blond hair and blue eyes will contrast nicely with the black costume."

"Yes, I can do a bun, or even a single braid."

"Exactly. I also have another pair of panties, leather of course, but much smaller, a thong really, it will leave your buttocks bare."

"I'm not sure."

"I insist, you must try it, if you are in a more intimate situation at some future time you will want them."

"OK."

Ken was nearly drooling while he waited for his Mom to come out of the dressing room. But after a few minutes a disappointed groan from his mother and a laugh from Rona announced that she wouldn't be coming out in the thong.

But she did come out in the previous costume.

"I'll get it anyway, I can always get a bikini wax before I put it on."

"You'll be surprised at how it attracts the men. And be sure to put your garters under your panties when you go to your party, it makes it much easier if you have to visit the ladies, and, well if things get frisky." Rona gave a little smile as she said the last.

"What about Ken?"

"A slave boy would be a good choice, and almost the only one. I have several ensembles."

Ken got white, he had forgotten that he needed a costume as well. Luckily his cock shrunk as his Mother and Rona looked at him. Rona then took his Kathy with her as she looked at several combinations.

Soon Ken found himself trying on one scanty costume after another. At the end he was shown a gold lame thong with some black wrist and ankle cuffs, as well as a collar.

"I think I get the idea, he doesn't need to try that on. They are all fairly skimpy, I suppose the leather pouch, the sandals collar, cuffs and that leather harness will do."

"It is probably best, but he really doesn't have the physique needed for these revealing costumes." Said Rona.

"I know, he is a nice boy, and I love him, but he's never been an athlete."

"He's thin enough, just very little muscle definition. In real life, with the people in the scene he wouldn't look much different than any other subbie, but for a costume contest he'll take away from the whole effect of your outfit."

"I can't think of anything else, can you?"

"There is something, but it will be even more embarrassing for him."

Ken was embarrassed enough as it was, having them discussing him like a prize ham didn't help. He wanted to help and decided to do whatever it took.

"Mom, I'll do whatever it takes, I don't know what kind of penalty there is, but it must be pretty bad, so I'll do whatever you decided."

"Your son loves you very much, just let me get what I need."

She came back with clothing that was predominantly pink with lots of white ruffles. Ken groaned and Ms Kent flashed him a smile that he could only describe as predatory.

It consisted of a pair of bloomers of pink satin, the leg openings had ribbons to tighten with bows, several rows of ruffles at the legs, and four or five more rows of ruffles covering the bottom. Over that was to go an underskirt of white ruffled lace that was full enough and stiff enough to stick out.

He had a bra, a camisole and a dress that barely came past his bloomer panties. The ruffled lace underskirt was full enough and had enough stiffening to hold the overdress away from him and show the legs of ruffled bloomers. He knew that if he bent over his bottom, covered in ruffles and lace, would be on display.

Rona Kent showed each item to them, then handed them one by one to Ken. When he was holding the whole ensemble in his arms she traced a finger down the side of his face, then cupped his chin, staring into his eyes she told him:

"It will take a very very brave man to wear these things in public, no matter if you love dressing like this or hate it, to wear it in public, to face possible ridicule, is going to be the bravest thing that you have ever done."

His mother stroked his head, "Honey I know how embarrassing this will be, for both of us, but I think this will do it."

He didn't say anything, just went into the fitting room and stripped down. As he was reaching for the bloomers he heard a slight knock on the door.

The door opened just enough for his mother hand to push through, she was holding something pink.

"Ken darling, Ms. Kent thinks you may need this under the bloomers, to sort of hold things down."

At first look it was a pink satin and white lace jock-strap, except it was a thong, the thin rear strap went between his cheeks. Well he thought to himself, I've had that darn leather thong on just a few minutes ago too. But somehow this pink lace thing was worse.

Problem was though, that he had been fighting an erection ever since he had seen his mother dressed up as a domanatrix. Pulling up the sating thong didn't help matters, and as he pulled on the satin bloomers his erection fought with the thong. He knew that he would be oozing pre-cum by now, or at least would be very soon.

When Ken came out of the fitting room door he was the very picture of a sissy boy-slave. He rustled as he walked, the pink and white set off his longish ginger hair and pale complexion. He was blushing and that added to the picture.

Rona was prepared and took a few pictures of the poor boy.

"Well Mom, what do you think?"

She stepped up and hugged him.

"I think we have a winner, do you think you can do this?"

"If you can, I can."

A half hour later and they were heading home in Kathy's car, she had not only purchased the sissy outfit, but the leather slave outfit, and the gold lame posing pouch and collar and cuff set as well. She had seriously looked at some of the female slave outfits as well, but in the end left them there.

Rona had thrown in two hooded full length cloaks out of a lightweight but opaque material, and she made sure that Kathy had a business card. She also told Kathy (while Ken was changing back) that there was a community of people in the fetish scene that met at various places, if Kathy was interested Rona would be glad to sponsor her, as well as Ken if he wanted to come.