The Halloween Wager


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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