Billy heard and felt the laughter of the mistresses. He could not see that the sissies had been wearing condoms while they got their release. Some were given handjobs, blowjobs, and some even had sex with their mistress. The mistresses gathered their condoms and made their way to Billy after being dressed.
His hood was taken off and he saw the sissies were still unlocked and that everyone had a condom in their hands. Alice walked behind him and said
“I want you to beg for them to feed you their cum.”
Billy grimaced and said
“Mommy please please please don’t make me do this! I’ll do anything please!”
Alice laughed in his face making Billy want to cry. His mother in law had made him into putty in her hands. Even though he kept his desire to not be humiliated, she had trained him to be this way.
“Say, ‘aaahhh!’”
The first mistress walked up and held the condom to his mouth which he closed immediately. They gasped and Alice laughed.
“Ooooohhhh Helga! I think it’s time to take some practice swings at my sissy.”
The massive woman came over holding a heavy wooden paddle wearing a black dress that had a long slit up the leg and a deep neck line. Helga said
“Don’t mind if I do dear.”
The women tied his ankles to more hooks and Helga lined up before she loaded up and gave Billy such a hard spank that the sound hurt the ears of the other people there. Billy wailed and started shaking asking for mercy and forgiveness. Alice quickly put a ball gag with holes in his mouth before saying
“The safe word is peaches.”
With that Helga unleashed five more spanks with the same intensity. Billy wailed and screamed as he tried to say peaches over and over again but his gag made it impossible to do so. He was sobbing and overall terrified of Helga now. She was relentless giving him only a few moments rest at a time.
Helga stood in front of Billy and tied his hair in pig tails saying
“Such a little baby girl. Crying and crying for your mommy huh? Do we need to get your diapers since you’re such a baby?”
They all laughed as Billy shook his head no while begging for mercy. Helga pulled out a cattle prod and liked it up to Billy’s nose and said
“Now the real fun begins. Dance.”
Billy looked confused then she zapped his now A cup titty making him squeal causing an uproar of laughter. She repeated herself
“Dance bitch boy. Shake that ass for me.”
She dragged the prod down his chest to above his pubic. She traced his cage and he tried with all his might to shake his ass for her making everyone laugh. Helga said
“Good girl!”
Then zapped Billy in the testicles 6 times making him pee himself a little.
“Are you serious??? Did you just wee yourself??”
Helga went and grabbed a cane before gathering his balls jutting them out and unleashing a flurry of strikes with the cane. Billy pulled and strained but it was no use. He kept babbling and babbling trying to scream peaches but no one could understand him.
She finally let up as everyone cheered except for the other sissies who trembled before Helga. Miss X said
“I think we found our newest sissy sitter ladies don’t you?”
All the mistresses agreed as Alice undid the ball gag saying
“I don’t want to hear another word besides you begging me to let you eat those cummies.”
Billy trembled and weakly said
“P…please feed me your cum…”
Without hesitation the mistresses walked up and fed him condom after after of cum making him beg each one of them individually. Once finished Billy was brought to his knees with his hands tied behind his back.
“Now the other sissies need someone to clean their messy clittys up. And guess who gets to do that yucky job.”
Alice smiled down at Billy who felt his testicles swelling and his ass burning. He nodded his head and they lined up as Billy sucked their little sissy cocks clean. Some got boners but we’re quickly deterred by how quick Helga lifted her cane.
The sissies were then locked up immediately after the cleaning and everyone went to the table to eat except for Billy, who was led to a flat cage standing up in front of the table.
To be continued.
Source: reddit.com/r/Erotica/comments/12oyy2m/mother_in_law_takes_control_part_26_f58_m27_sissy