The Halloween Wager


It was quite a bill, but until and unless she was divorced her husband was paying the credit card bill. She made a mental note to call him and explain, in general terms, that the costume was was very expensive.

Kathy had just put her winter coat over her outfit and gone to the car with her street clothes in a bag. Ken had insisted on changing back.

In addition to Ken's outfit she had also purchased a pink leather collar and matching leash, along with some three inch heels that fit him, and some breast forms that would fit out his 'B' cup bra.

After they got home Kathy prepared dinner. Kellie, Ken's older sister was staying at the University that she was attending, and wouldn't be home this weekend, much to Ken's relief. After dinner they sat in the living room staring at the blank TV, both a little shell shocked.

"Mom I am so sorry I didn't listen earlier to you about getting a costume."

Ken and Kathy had both completely forgotten that she was still in her costume.

"It's OK honey, I didn't know 'till this morning that the bet was still on. It's probably better this way."

"If I'm going through with all this, I ought to know what the bet is, it might give me incentive to act my part better."

Kathy sighed, she knew this was coming, and she felt that he should know, even if the odds were now that they would beat Sherry.

"This is very embarrassing, and you can't tell anyone, but." She stopped, it was hard to admit to her son.

"Go on Mom, you were almost there."

"Sherry and I don't get along. I don't know why, we just always seem to clash. It's more an instinctive thing than anything either of us has done, I'm sure that she's actually a decent person."

"OK, but that doesn't explain ...."

"It's more than that, It goes back a long time. Before I went to work there. You see, when we were younger, when your sister was a baby, even before you were born, well, your father and I were."

"Go on."

She took a big breath.

"We were swingers."

"You mean like wife swapping?"

"Yes, it was something we tried. It was fun, actually I didn't want to go at first, but your father wanted to, it turned out to be fun."

"So you just went the one time? Who else, I mean, how did you find someone else?"

"We didn't just go once. It was a friend of your fathers', he and your Dad had talked about it a lot I guess, then your Dad talked me into it, just at their house one night."

"So you just went over and what happened." Ken was excited, his normal, conservative parents, that always told him to wait for the right woman, warned him about sex, then he finds out they were swingers.

"At first we went to their hot tub, naked, then the next night that we went, we started making out with each other. Then we went to their 'party room', it had mattresses all over the floor. Your father and I had sex next to them, there were doing it as well. It kind of escalated after that."

"Did you, and the other man, do it?"

"Yes, usually with your father right there, sometimes in other rooms."

"And that was it?"

"No, there were other couples that they introduced us to, sometimes there were three of four other couples at the same time, a few times there were, well, I guess you would call them orgies."

"Oh wow, you were a swinger, orgies!"

"You can't tell anyone this."

"I know, but where does Sherry come into it."

"She and her first husband were one of the couples, you know how some people just don't get along, well she and I were that way. She kept picking your father, and her first husband wasn't much in the sack."

"So you got the short end of things?"

"Not always, someone else got him, some of the ladies liked him fine, and really he was OK, it was just that she made such a big deal about your Dad, and he really liked her."

"Oh, OK."

Ken was seeing his Mom in a completely new light. He always knew she looked good, but now, now she was positively a sexy knock-out."

"And then we sometimes had parties, that's what we called them, parties. Sometimes we had contests."

"Wow, like what?"

"Silly things, like who could make the men cum the fastest. We kept score from week to week, and she was really good. She loved it that she got your father off faster than I could, or anyone could."

"Didn't you ask him to try to slow down."

She looked at her son blankly.

"Of course honey, but he would just say that she was so sexy."

"Ouch, that must have hurt. So you made him quit?"

"No, he wanted to quit first. We slowly wound down, there was this one couple that we went with for a long time after we stopped going to the group things."

"So sort of like a four way marriage."

"Sort of, but just for sex, and just once a month or so. A few times we actually split up, me with the other man, your dad with the other wife, for a whole weekend, in separate places. I would get your grandparents to take Kellie for a weekend and he would come here, your Dad would go to their house."

"Wow. So why did you stop."

"A combination of things, mostly your Dad wanted to."

"And you wanted to go on?"

"Yes, actually I enjoyed it when we were all together, sort of a four way orgy, I liked others to be there."

"But you stopped because Dad wanted you to."

"Sort of, I ... I, uh. Well I kept on for a while."

"Without Dad?"

"Yes. For a little while."

"Did he know?"

"At first, yes, the first few times, they invited us over and I went without him."

"But then?"

"You mustn't tell anyone, especially your Dad, but yes, I kept meeting them, and others, and sometimes just the men, sometimes just one of the wives. I kept doing it for about 8 or 9 months after your Dad thought that I quit."

"Wow, just you and another woman, that's hot."

"It started because her husband wanted to stop as well, and we were both free during the day, while our husbands worked, so we would meet at each others' houses."

"While Kellie was there?"

"She was just a baby, the other lady would bring her baby over too, and once they were asleep, we would go to the bedroom."

"I always thought you were sexy, but this, this is ..."

"No one knows or will know Ken, are you straight on that!"

"My lips are sealed, but what about Sherry?"

"Well, after your Dad stayed away, at first he said I could go if I wanted, so I did, and once when I went over, thinking it would just be the three of us, Sherry and a new boyfriend was there. And we made it a few times. But it was always a contest with her somehow."

"Is that all?"

"I know it sounds silly, but since I was there alone, she made it sound like I really wanted sex, I guess I did, but sometimes she would call me Kathy-slut when we were hot at it."

"Kathy-slut, wow."

"Sometimes slut-Kathy, and soon she became a regular there, and she began to bring extra men, just for me, she said, like I couldn't find any of my own, a few times she brought two extra guys, so I had two guys at once. She called me 'slut-girl' then. And then she started calling me up, calling me that, and telling me to be somewhere or another and have two, or three sometimes four guys, and just me. They all called me slut-girl."

"Oh Mom!"

"I know, I couldn't help it, then your father found out, that I was still going, not about the gang-bangs, and he was really hurt, but it was like a drug, not because it was fun, just because there were all these men that wanted me, it was really a high."

"What did you do?"

"I stopped, just stopped cold. Your Dad was very good to me, he did everything he could to make me feel wanted, and that was really the problem, I didn't miss it afterwords, but I really wore him out. Then about a year later I went off the pill and got pregnant with you."

"And you haven't wanted to do it again?"

"Nope, sometimes I have fantasies of another man, just day dreams, but I've never really thought about a gang-bang since you were born."

"And all this time you were working with Sherry?"

"No, she just started there about a year and a half ago. I don't think she realized it was me for a few months. We haven't said anything, just don't like each other."

"So what's the penalty, another gang-bang?"

"No, the losing couple have to be sex-slaves for the winners, for a weekend."


"And you can bet that they'll want us to do it if we lose."

Ken was worried, and all his apprehension of appearing in public as a sissy were over. He had to win. At any cost.

For the rest of the evening they talked about what they would do. Kathy had reserved a room in the hotel where the party was to take place, Lots of the company employees did, it was traditional that there was a lot of booze drunk since the company paid for the open bar, and arranged a special rate for the rooms.

It seemed that there was a parade early in the night of the contenders for the various prizes, many of the contenders for the prizes would hide their costumes and only uncover just before joining the lineup to parade past the judges.

As each contender or couple was in front of the judges they could pause for a few seconds and do any kind of routine that went with the costume. Usually lots of musketeers and pirates swished their swords, belly-dancers danced, stuff like that.

After finishing the parade, usually a route around the room, contestants could circle into a central area for more involved routines. Ken and Kathy thought up a few things that they would do, all of them would be more humiliating for Ken.

That evening as the headed for bed, Kathy came out her bedroom and intercepted Ken as he headed into the bathroom. She carried a short nighty and matching panties.

"I know this is even more embarrassing for you, but we need every edge, if you wear this tonight maybe it will get you into the spirit of things, and I want to practice with you in the morning, I'll get something for you to wear so that we won't wrinkle your outfit, but I want you to completely act like a sissy slave boy by tomorrow.

He looked at her, then lowered his face, took the garments.

"Thanks Mom, I won't let you down."

He spent the night in satin, and even went to breakfast that way. He had been excited all night, had sexy dreams about his mother and himself. Before he could get to sleep he had to bring himself off. He was careful not to get anything on his night dress.

After breakfast his mother had another pair of panties for him, very frilly, along with a camisole. She had a bra that his older sister had worn as a teen-ager and it was the same size as his sissy one. His mother glued on his breast forms and he put the bra on.

She started to put a pair of nylons on him.

"Honey, you are going to have to shave your legs, and while you're at it, we should probably shave your arm-pits and chest as well."

He nodded, and red faced he stripped down to his panties and followed her to the bathroom, he put a new blade in his razor and she got his legs and pits, then went to his chest and tummy. He really wasn't very hairy and it was quickly done.

"Ken dear, I can't help but notice that with this low cut pair of panties your pubes are sticking out the top, and even a few stray hairs are coming out of the inner leg holes."

"Do you want to shave there too?" He was OK with the rest, but this was getting bad, he was aroused just wearing these clothes and now being half naked with his mother he had a semi woody.

"I know this is going to sound bad, but I was thinking that for our routine I could discipline you, spank you with the crop, and to make it convincing I should pull your panties down."

"What about the thong?"

"Maybe we shouldn't use it."

"That might be super embarrassing."

"I can't help but notice that you're aroused in these clothes."

"I don't know if it's the clothes, or just being around you after hearing about your swinging and all. Or maybe the idea of doing this in public, but I keep getting hard."

"We're going to change in our room at the hotel, maybe you could take care of things just before we go to the party, and if you need to, do it here today as we practice. That'll get you tired out."

"It might work, but how much do you want to shave?"

"You get what you can, if you don't mind I'll check and pick up any you miss, I think you should be completely bare, we should probably do your arms too, even though you don't have much hair there anyway, and don't forget your toes and fingers."

"That will be OK, I'll be wearing long sleeved shirts until spring anyway. Do you have to check?"

"You don't have anything that I haven't seen honey, and remember, if we lose this because of some detail, you'll be showing everything."

"All right, lets get started." He didn't wait for his mother to leave, he just pulled down his panties and started clipping his hair, seeing this his mother stayed and watched and helped.

She was more nervous about him if they lost than she was about her. Sherry had mentioned that her husband was bi, and that she liked to use a strap-on. She didn't want either of them hurting her son, who she knew would honor the bet and submit to anything asked of him.

The hardest part for Ken was when he bent over holding his cheeks apart as Kathy shaved him clean. With virtually no hair on him below his eyebrows Ken spent the rest of the day practicing the role of a sissy slave to his mother.

Kathy practiced going down on one knee, the other leg forward with the foot flat on the floor, leaving her thigh level and ready for sissy-Ken to bend over for his spanking. The also practiced him just kneeling on the floor, his head on the floor and his bottom raised with legs parted. Kathy could easily swat his behind with the crop in that position.

After lunch Kathy took him into her room and sat him at her dressing table. She started to put make up on him, but stopped and lightly plucked his eyebrows. She didn't give him much make-up, just some blush and eye liner, shadow, and fake eye lashes, along with bright red lipstick.

She also gave him a manicure and painted his nails to match his lipstick, she also painted his toe-nails.

By mid-afternoon they both were very confident in their roles, they showered and then met in Kathy's room. Ken was wearing his boxers and t-shirt. Kathy was wearing panties and a bra. While in a shower she had shaven herself completely smooth.

Ken was expecting to be made up again, but Kathy told him that she would do it at the hotel, and told him to go and pack an overnight bag, that they would spend the night at the hotel since the party wouldn't be over until very late.

All to soon they were on the way, the costumes in clothing bags, Kathy was nearly as nervous as Ken, while he had been obviously excited to be near her all day while wearing her lingerie, while had been wearing a garter belt and stockings with panties and bra along with her new boots, just to get into the mood of things, and it had excited her as well.

Once it had gotten to be too much for Ken and he had developed a full erection, they both stood there staring at it for a few seconds, both blushing, Kathy's nipples were standing out and she could smell her arousal. When Ken had gone to his room to masturbate, she had done the same in her room.

They checked into the Hotel and went to their rooms. It was still a few hours to the start of the party, so they ordered a light meal from room service. All to soon it was time to get into costume, Ken gave his face a last shaving, and got into costume.

Kathy got dressed and Ken dropped his jaw in surprise to see that instead of the leather panties, she was wearing the leather thong. He helped her on with her boots and realized that her pussy lips were barely covered by the thin strip going between her lips.

"Are you going to need to masturbate again."

"No, I'll be OK, I'm really nervous."

"You were looking at me awfully hard," she said with a smile.

"You are so beautiful Mom, so very sexy, if you weren't my mother, I ..."

"I know son, I know. Me too."

"Put on your cloak and lets go."

Once in the ballroom that had been reserved for the party they were surrounded by people in costume. His mother worked for a small company, but it did employ a little over a thousand people, and the Headquarters facility and the plant in this area consisted of about seven hundred.

It seemed to Ken that all of them came, and brought their spouses. In actuality there were probably not more than 200 people all together. Kathy explained that it was an adult party in every sense of the word.

Many of the costumes were very skimpy, and there was a lot of flirting and even some groping going on before the evening was over. A lot of the single people hooked up before the evening was out and even some of the married people usually to end up in the wrong rooms.

There was also a lot of drinking that would go on. She showed him that the stamp that was put on her hand was different than his. Hers was red, his was black.

The reason was that everyone had to be over eighteen, but if you weren't twenty-one, then you couldn't drink and the bartenders wouldn't serve alcoholic beverages to anyone with a black stamp.

"That's silly, not the drinking thing, but the eighteen rule, in this state the age of consent is sixteen!"

"I know dear, but Mr. Gore sets the rules, it is a privately owned company and he is the sole owner. Or at least he and his younger sister, that's her in the harem outfit."

"Wow, she can't be more than thirty, if that."

"Prettier than me?" She answered with false anger.

"No Mom, no-one is prettier than you."

"Look, there's Sherry's husband."

"He's wearing a cloak as well, or at least a bed sheet."

"Yes, but look at what he's carrying, it looks like a horse head."

"You don't think they're going to be a horse do you?"

"That would make her a horses' ass! Surely it won't be that easy."

"Mom, you're always telling me not to count my chickens...."

"I know, there's something else going on. It looks like he's got a lump on his back. It's going to be different whatever it is."

"How come some people are covered up like us, and most aren't?"

"Some, like us, are in risque costumes and are only going to show it at the parade, others are just doing it for a surprise."


"Yes, I'm not the only one involved in a bet, it's a tradition that there are a lot of risque costumes, and another that there are a lot of bets, sometimes for some of the prizes, some for the most shocking."

"Have you bet before?"

"A few times, usually for bragging rights or a round of beers or something, always before it has been a department bet, mine against another department. I only made an individual bet once before."

"What was that?"

"It was when I transferred from the order department to accounting, the head of the department at the time was Miss McCartle, she said that if I would show up as a stripper she would OK the transfer and jump me a pay grade."

"Why would she do that, surely that wouldn't be allowed."

"She was an odd bird, that's for sure. But she was a relative of Mr. Gore, didn't have any ownership of the company, but he let her pretty much run things the way she wanted."

"Did you do it?"

"Yes I did! It was between me and someone else, we were both equally qualified, had both worked for the company about the same amount of time, and I think she just didn't want to make a choice herself."

"So you just dressed as a stripper? What did the other person dress as?"

"We were both dressed as strippers, I was more old fashioned, a long gown, opera gloves, garter belt, stockings, that sort of thing. She was more modern, a sleezy short gold lame dress, torn stockings high heels."

"I know you got into that department, you work there now, so how did you win?"

"It was quite simple really, she didn't strip, I did."

Report Story

by49greg© 10 comments/ 161279 views/ 83 favorites

Share the love

Report a Bug

5 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: