Literotic asexstories – The Halloween Wager by 49greg,49greg 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.
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.”
“Ouch!”
“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.”
“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.”
“You stripped!”
“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!”
“Yes Mistress.”
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.
“What?”
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
lodged.
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.
Ken noticed a slight squelch as he pulled the crotch away from her pussy lips, and the aroma of what he though of as his mothers’ arousal got stronger. The lips were moist.
Kathy had hoped that he would have gotten over his mother-crush by now, but thought that perhaps the absence of his father was prolonging it. She couldn’t deny that the preparations of the last few days had built up a sexual tension between them.
He pulled the thong down and she stepped out of it. He placed it with her other things.
“Bend over and kiss her feet sissy boy, she is your mistress after all.”
As he bent over. Sherry could see his bare bottom under the frills of the short underskirt he still wore. She cold see his balls and his erection. She noticed that his balls were shaved. They had really gone all out with their preparations for this contest.
Kathy was trembling with suppressed excitement. She was horrified by what Sherry was making them do. She knew that she could probably get out of this debt, after all it was going too far. But she didn’t push it. Partly from bravado, she wanted to show Sherry that she had the guts to do it.
But Kathy was also turned on by her son, ever since they went into that fetish shop with Ms. Kent she had been feeling a vibe from her son. Maybe it was in her mind, but she though he was also feeling something more than a crush.
Ken kissed her feet, he ran his tongue between her toes, he tasted and smelled the sweat, he didn’t care he was worshiping his mother. He moved to her other foot and kissed and licked it as well.
Kathy was loving his kisses, she hadn’t expected him to more than the bare minimum, but here he was acting like they were still playing the mistress slave game. She mentally shrugged, they still were, only Sherry was the mistress.
“Kiss your way up her shins, kiss her knees.”
Kathy shuddered and moaned inwardly, she could see where this might lead, her own son, body worshiping her, if he kept going upward ….
Ken loved it, he knew he was exposed to Sherry, and his cock thrilled to the attention. He kissed his way up her legs, not so much licking, just light kisses up her legs, going back and forth from one to the other as he worked his way up.
“Straighten up Ken. Stare straight ahead.”
He straightened up. Regret that he wasn’t going to kiss his way to her pussy, he knew that he would never get another chance like this to her. He wanted to taste his mother, but didn’t want to let either of the two women how eager he was.
Kathy was horny, the old feeling that she used to get when she was a swinger was coming back, she wanted sex, with a man, a woman, or even her son. She tried to hide it from Sherry.
Sherry was excited, she loved the idea of being in charge, and she loved the idea of fucking Kathy’s son. It was even better than fucking her husband. She could smell Kathy’s arousal, and see that Ken had a hard-on, but didn’t realize that he was turned on by his mother.
Originally Sherry thought that she would let the boy fuck her, then have his mother take his anal cherry with the strap-on. Now she thought it would be more fun to make the boy fuck his mother, and then have one or both of them fuck her.
Sherry assumed that making the boy fuck his mother would hurt Kathy more than having one of them take him with the strap-on.
“Lick her sissy.”
He turned to look at Sherry, he tried to put a horrified look on his face.
“Please Sherry, not that,” Kathy whispered.
Sherry leaned forward and brought her hand back and with a full swing slapped Ken on the face. It hurt Ken, Sherry was surprised how much it stung her hand! She managed to keep the pain from her face.
“Lick her!”
His face stinging but secretly elated Ken leaned forward and placed a kiss at the top his mother’s slit.
Sherry directed Kathy to step back and sit on the bed. Ken moved between her legs at her order, but she stopped him and made him strip the petticoat. His erection bobbed in front of him. Both women assumed it was because of the presence of the two naked women.
Kathy realized that he was attracted to her but didn’t realize how much. Sherry did not suspecting the true cause — he was excited by his mother, and only marginally by the naked Sherry.
When she ordered it, Ken leaned forward again and kissed his mother’s pussy, he started to lick up and down her slit, trying to worm his tongue into her. He had read about licking pussy but had never done it and he was trying to find her clit with his tongue.
Suddenly his tongue slid into it, it seemed huge, he had no idea how big it was supposed to be, but he thought this was big. It was easily the size of the tip of his little finger and now it was actually peeking out of the folds of her slit.
He felt his Mom jerk when he first hit it and now he was licking all around it. His Mom murmured to be careful, not so hard, not so direct with his tongue. He took the hint and the other hints, her murmurs and the hands on his head directing him.
Soon one of her hands left his head, and the other just gently lay on his head, reminding him that his mother was the one he was eating. He was like a kid in a candy shop.
He licked and nuzzled freely, when she sounded like she liked anything, he kept doing it, he slid first one finger, then another into her. He was loving it, and managed to push a third finger into her.
Sherry was excited, horny, totally horny, she had planned on reducing Kathy into a slut by Monday, and beyond. She dreamed of having Kathy-slut at her disposal for ever.
When she saw how excited Ken was, she also wanted him, he would be a willing stud for her, and she hoped eventually for her husband or whomever else she wanted. Perhaps she could find a porn producer that would use the two of them in and incest film.
But now she had become so turned on that all she wanted was orgasms, lot of them. She stepped over Ken and put her knees on the edge of the bed and leaned over and started kissing Kathy.
Ken noticed the weight of Sherry moving the bed as she knelt on it. He looked up and could see along his mother’s body, he now saw Sherry poised over his mother and kissing her. It looked as they were in a deep open mouth kiss, with dueling tongues.
He looked up and just above him he could see Sherry’s pussy, her breasts were pressing against his mother’s. One of his Mom’s hands was snaking back towards Sherry’s pussy. Ken bent back towards his mothers pussy.
Kathy came right away, her thighs capturing Ken’s head and holding it tight as her pelvis arced upwards.
Sherry collapsed onto Kathy and Ken was pulled back, he cold see both pussy’s, one atop the other. Sherry’s bottom was there in front of him as well. He didn’t want to lick it, but thought that if he tried now without being told, maybe she would let him off lightly.
Sherry felt Ken start to kiss her bottom cheeks, several kisses on each cheek, slowly working inwards. Soon she felt his hands pull the cheeks apart, there was a pause, she imagined him looking at her little rosebud. She was proud of how she looked.
Sherry grinned and started to kiss her enemy again, she thought that it would be fun to see Kathy’s face when she found out that Ken had already eaten Sherry’s bottom.
He stared at the crack before him, he could smell her pussy and he slid a finger into her and got it wet, he ran the finger coated with pussy juice up and down her bottom crack.
Kathy was hoping that the gently kisses and the obvious delight that Sherry seemed to be experiencing as they kissed each other meant that she had mellowed out a little.
She could feel Ken between her legs still, and he seemed to be moving around, but he wasn’t eating her anymore.
Ken slid his finger down to his mothers pussy, it was even more soaking wet than Sherry’s, he collected as much of her essence as he could on his fingers and tried to transfer it to Sherry’s bottom.
He took a large breath and started kissing at the top of Sherry’s crack, and worked his way further and further down. It wasn’t as bad as he had feared, it wasn’t going to be his favorite thing to do, but he thought he could do this.
Sherry loved the feeling of the tongue approaching her little rosebud. It sent a thrill through her, not so much from the act itself, but that there was someone who could be compelled to do it.
He came to her anus, he kissed it, then started to lick all around it, he went on down her taint, then back, and resumed licking, he pushed his tongue in, the meaty heavy smell wasn’t great, but she obviously kept herself clean.
She felt the tongue try to penetrate her, so she tried to relax her muscles and it actually popped in. She smiled against Kathy’s lips. She pulled her lips away from Kathy and snuggled her head down towards Kathy’s ear.
Kathy felt Sherry start to nibble on her earlobe, the let go and whisper to her:
“His tongue is in my ass, your son is licking my ass and sticking his tongue in.”
Kathy closed her eyes in pain, she wanted to throw Sherry off of her, throw her across the room and gouge her eyes out. As suddenly as the rage came, it went, she felt a flutter in her stomach. Maybe he’ll do it to me as well, was the thought that came unbidden to her.
Ken kept up his ministrations for about five more minutes. It seemed like hours, her ran his hands over her bottom, up her sides to her armpits, up her back, then back to her bottom, never leaving contact.
One hand slid down to her pussy with the thought that he could make her cum again. He wanted her tired and satisfied. As he ran a hand down to her pussy he found a hand there already. He could see that Sherry had both her hands holding onto his Kathy’s shoulders, so it could only be his mother’s hand.
Sherry felt both mother and son working on her and she loved it, but it was time to get on with her plans.
Ken felt Sherry push her bottom up and back, her hand reached behind her and pushed against his head. He pulled it back as she stood back up, and stepped over him and back to her chair.
“That was very good sissy boy, I like that you showed initiative, and I may show you some leniency later. I want you to go and wash your face and brush your teeth and come back, don’t you dare touch your cock.”
When he came back he found his mother on bed, face down. Her hands were tied to the headboard and her legs spread, each ankle also tied to either end of what looked like a collapsible aluminium rod, perhaps a hiking stick. She was bound to one side of the king sized bed.
With her legs spread and hands tied above her head she was helpless, he could see how her pussy was soaking and had already started to soak the mattress. She was also gagged, there was a wide piece of duct tape over her mouth.
Sherry was standing beside her, she was holding up another strap-on, it was huge, far too big to fit he thought, it had to be 15 inches long and bigger around than a beer can.
“You have a choice to make, either you fuck your mother and commit incest, or I fuck her with this. I can’t guarantee that it won’t tear something because I won’t be gentle. Make your choice.”
“I .. uh.”
“Don’t look at her, and be quick.”
“I’ll do it.”
Sherry was ecstatic, she planned on taking pictures and using them to blackmail Kathy to do whatever she wanted.
“I thought you would, but first, while your mother is tied up, I want you to fuck me.”
She directed Ken to lay down on his back next to his mother.
“I can see you’re erect, you must be excited, I want you to remember this moment, you mother is convinced that you are a virgin, is this true?”
Ken hesitated, then answered in a quiet voice:
“Yes ma’am, I mean I’ve never actually had intercourse.”
“What kind of experience have you had, go ahead and stroke your cock while you tell me.”
Sherry got on the bed and straddled Ken’s thighs.
“I, uh, made out with a few girls, and, well, felt Cathy Robbie’s tits, and Sandy Booker, uh, she, she uh, sucked me.”
“Oh, so you’ve had a blow job, did you cum in her mouth?”
“Uh, no, I was too nervous, and she had to go inside, we were in my car in her driveway, and a light went on in the house.”
“Just as well. Perhaps I’ll give your mother a chance to give you a blow job tonight, would you like that?”
Ken was embarrassed, he would love to get a bj from his Mom, but he also knew that he didn’t want Sherry to know that. On the other hand he didn’t want his mother to think that he didn’t want her to do it. He didn’t know what to say.
“You don’t have to say anything, your face gave you away, let me give you a tip, don’t ever try to play poker.” Sherry then laughed. It sounded to Ken like the laugh of an evil witch, to Kathy like the laugh of a triumphant conqueror.
Sherry leaned forward, he tits were inches from his face, he just stared at her distended nipples, he paid no attention to her while she took one hand and handcuffed it to the headboard right next to his mothers’ hand.
He felt his mother reach her hand to his and clasp it, he squeezed her hand in response. It made him feel a little better. With both of them secured he felt a little fearful.
Ken turned his head and faced his mother, he could see tears coursing down her cheeks, her makeup smeared. He was glad that he had scrubbed his off while he was in the bathroom. He smiled at her. It looked like she smiled back under the tape.
While he was still looking at his mother Sherry eased forward and sat on his cock. She sank down on his in one stroke. He could feel her, but he thought that it should have felt tighter. It just seemed loose.
She grabbed his free hand and brought it to her breast, guiding his fingers to her nipple.
“Pinch it, tug on it, not to hard, yes, yes, yes, that’s it. Keep it up.”
She began to fuck him, lifting herself up and down, he instinctively fell into a rhythm thrusting up as she came down, and pulling back as she rose. He looked at his mother and she was sobbing beneath her tape gag, her eyes were running and so was her nose.
“Look at your pitiful slut mother boy, she’s sad that she isn’t the first one to fuck you.”
He squeezed his mothers hand, as he continued to fuck Sherry, she continued to crow about fucking him in front of his mother. It seemed to go on forever, her pussy was stimulating him, but not as much as his right hand usually did, in spite of that he felt the beginnings of cum building up.
Ken came suddenly, as much from the idea that he was finally fucking a woman as from the friction in her loose pussy.
Sherry immediately moved off of Ken and squatted over Kathy, ripping the duct tape off of Kathy’s mouth, reaching four fingers into her own pussy she pulled out gobs of Ken’s sperm and smeared it on Kathy’s mouth.
“Eat cum you slut, it’s not the first and it isn’t the last, open up and swallow it!”
Kathy complied as best she could in her face down position with her head turned sideways. She actually didn’t mind eating her own son’s cum, it wasn’t like it was voluntary and that seemed to satisfy her conscience.
Sherry leaped off the bed and standing beside Kathy she began to spank her, it began to sting her hand and she pulled a ping pong paddle from her bag and began to swat Kathy with that.
“Please don’t hit her so hard, please, we’ll do whatever you say, just don’t hit her so hard.”
Sherry had a wild look in her eye and suddenly stopped, she handed the paddle to Ken.
“Go ahead then, you hit her, spank her hard, your slut mother just ate your cum without a whimper, what kind of slut does that. Hit her!”
Ken tried to not hit too hard, he could just reach her bottom from his position, and Kathy actually tried to move forward to help him. Ken felt sexually charged hitting his own mother on her bottom, her lovely and bouncy bottom.
He had been ogling her bottom all evening and now he had the chance, he just wished he could use his bare hand, but then he would caress it, not hit it.
“That’s enough you sissy boy, get over her, fuck her.”
She grabbed the paddle from his hand and pulled him over his mother. He tried to clamber onto her as best he could with one hand cuffed to the headboard. Kathy scrunched up as best she could.
Ken couldn’t believe that he was suddenly hard again, this was nothing like any of the scenarios he had played in his mind for the last few years when he masturbated while thinking of his mother. But it was just as erotic.
Before he knew it he was between her legs as she raised her bottom up toward him. He inched forward, he didn’t know what to think of the expression on her face, he just wanted to get his cock into her.
Kathy would happily taken the huge cock, no matter the cost, but was relieved that Ken was going to fuck her. She was alarmed when she saw the cameras that Sherry produced from her bag.
Sherry quickly extended the tripod and started the movie camera going, meanwhile she took the still camera and began to snap pictures. The lighting in the room was plenty adequate for what she planned.
Ken tried to hunker closer to her to cover as much of her face as he could.
Sherry was a little frustrated with the way Ken was trying to cover up Kathy’s face. She stopped the movie camera and reached over and pulled Ken’s head back by his hair and told him not to hide Kathy’s face. She ordered both of them to look to the side and smile.
As Ken entered his mother he nearly came just from the mental stimulation of knowing he was fucking his Mom.
Kathy also loved the sensation, it seemed like her son’s cock hit every nerve ending in her vagina, in a very very good way. She let out a sigh.
Ken held himself still, he ignored Sherry and concentrated on not cumming, he wanted to make his Mom cum from fucking. He loved the tightness of her pussy.
Kathy loved it, she realized what Ken was doing and didn’t try to clench or move until he did. And soon enough the worried look on his face dissolved into a grin as he started to slowly pull out, then back in. He was soon pumping into the pussy that he came out of all those years ago.
Kathy was in heaven, the rope holding her ankles was biting into her, but she ignored it as she tried to push up onto Ken as he pushed down into her. She could feel the beginning of an orgasm coming.
Sherry was livid, those two bastards were enjoying it! She would show them! It wasn’t so much that they did anything wrong, it was that they hardly complained at all and complied with whatever she asked. What kind of revenge was that?
She fumed as she filmed. Furious as the woman she hated enjoyed fucking her own son and so did he. She tried to ignore the tiny little pop-up message in the back of her brain that asked why she hated Kathy and what did she need revenge for.
Kathy came. She shrieked her sweet agony as Ken continued to fuck her, he was like a metronome, and now he was pulling on a nipple with his free hand. Kathy started to make grunting sounds as she felt another cum on it’s way.
This wasn’t what Sherry had planned, she had bargained with Kathy while Ken was in the bathroom, Kathy would let Ken fuck her and Sherry wouldn’t use the strap-on on Ken. Now she felt like it was a trap, she’d been suckered.
At least she would have the film, she would make her life a living hell, she would give the film to her husband, Kathy would have nothing when he divorced her. She held onto that.
Why do you hate her. Hasn’t she always done what you said?
Shut UP! I’ll show her!
Kathy came again, and again, a whole series of rolling cums. By now Ken was kissing the back of her neck and her shoulder, tugging and pinching her nipples and slamming into as fast as he could..
He had changed his angle a little as she tilted her pelvis as much as she could, each stroke rubbed hard on her g-spot and the rolling cums were building up, she could feel it, like nothing ever before, nothing else existed, just her pussy and his cock.
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