The Halloween Wager

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49greg
49greg
453 Followers

Sherry had dropped the still camera and snatched the strap-on up, she detached the dildo and looked at it, looked at Ken's bottom.

Golden white fire filled Kathy's vision, filled her brain, her pleasure center was overloaded, her pussy clenched down on the cock and squeezed, it shot, it shot and shot and shot, filling her with white hot cum.

He collapsed onto her.

It was quiet, a few street noises made it up to the room. Ken had untied Kathy and tucked her into bed, she was breathing deep and slowly in her sleep. He cleaned up and dressed, trying not to look at the form on the floor.

The room 'phone rang a few minutes later. It was Sherry's husband. Ken asked him to come down.

Sherry sat on the floor, leaning back against the foot of the bed, legs spread and the giant dildo shoved all the way into her pussy, she drooled and panted. The quiet monotone she panted out was hard to understand, but they finally understood it.

"Gotta cum, she cums I don't, I gotta cum she cums I don't, I gotta cum she cums I don't, I gotta cum.

Her husband looked at Ken sadly.

"Don't worry, she does this sometimes. She finally told me once that the only time she ever came was once when she was with Kathy, she seemed to hate Kathy and I don't know why.

"She usually ends up wearing me out and then forcing that monster into herself, but she never cums. I tried to get her to see someone but she refuses."

"I'm sorry. I couldn't understand this bet, but I just got sucked into it."

"The last thing she said to me was that she was going to cum again and rub Kathy's face in it."

"Are you sure she's OK?"

"Yes, look, I think she said something to Kathy's husband, probably told him some lie, I know they split up afterwords, you might tell her that."

After they were gone with the bag and all the gear. Ken locked the door. He checked one more time and made sure he had the flash memories from both the still camera and the movie camera. He smiled, he had finally fucked his Mom and she seemed to like it. They might never do it again, but it was something he would always cherish.

49greg
49greg
453 Followers
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ToughSailorToughSailor6 months ago

I'm really not into the dom/sub thing but just had to read the story to the end just to find the outcome. Have to agree with rightbank's comments that there we no winners . . . .

Foxterot7aFoxterot7a11 months ago

I liked the story but do not know why. I felt sorry for the son even though I realized how much he loves his mother. With as much implied shame, guilt, self-loathing, self-doubt, and self-recrimination, I would have liked to read about how the 4 characters were able to interact with each other the morning after/week after. The psychological/psychiatric damage that could be done to mother, son and co-worker could be tremendous.

rightbankrightbankover 6 years ago
They all

Lost

There were no Winners

AnonymousAnonymousalmost 9 years ago
mothers love

I love this story, it reminds me of my time with my own mother. I still dress as a sissy with her and we are still lovers 20 years later.

my parents split when I was very young, there was me and my twin sister, she always dressed me as a girl in lovely frilly sissy girl clothes, as I grew into puberty she kept my body hair free, the clothes felt wonderful, as I grew my erections became stronger as my penis grew she would gently stroke my hardness, on my sixteenth birthday we followed our routine until the evening, she gave me a baby doll nightie with sheer matching panties, she told me to put them on then go to her room in 15 mins, when went to her room she was wearing an identical nightie, her naked breasts and shaven pussy clearly visible through the thin material, I had longed for so long to see her naked body, my cock throbbed in the panties, she beckoned me to her, her arms went around my waist and we had our first lovers kiss as she pulled me against her, she guided me to her bed, she gripped my cock through my panties, and took my hand first to her breasts then her pussy patiently showing and telling me how to touch her, her pussy felt so good and so wet, we removed our nighties, I then got to taste her pussy it was everything I expected and more it was so sweet and salty, my mum said she wanted my cock in her pussy but only if I promised to be hers and my sisters sissy sex slave, I moved up her body and slid my cock easily into wet welcoming pussy, this first time inside her I did not last very long, she got me to lick her clean I lapped up every drop on our combined juices, I was so engrossed licking my mums pussy I had not noticed my sister enter the room until she got onto the bed, my mum said I should now please my sister, which I did gladly and took her virginity.

the three of us all still live together and I am still their sissy sex slave, I have seen them with many different men and women and tasted all of the guys spunk from their pussies I have also had many men use me too, god I love my life.

AnonymousAnonymousover 10 years ago
Not sure about this one

It appears in the ending that Sherry has some unexplained mental issues? And why would Kathy risk her son in this silly wager that could have been called off by a simple"no"? Why wouldn't she call her husband to help her? She could have explained the bet to him. And who was Ms. Kent really? I found it hard to believe that Kathy would let her take pictures of her son that day in the shop. Not that this was badly written, but there were to many unexplained issues and too many implausible happenings to make it an enjoyable read.

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