Billy had his hands tied above him and his ankles tied almost spread Eagle with his tip toes on the floor. His flat cage felt super compressed from the daily teasing and maintenance spankings. She would unlock him every morning when he awoke and every evening before bed. Edging him multiple times before locking him back up.

Today was different though. It had been 2 months since the beach and Billy felt more submissive than ever. As she dressed him, he didn’t even budge in his mind. He let her put on the cute pink bunny outfit which split his asscheeks in two and showed off his hips with how high the cut was.

His toes were painted pink and his lip gloss was pink as well with super rosy cheeks as his makeup. Alice had him blindfolded as he heard her heels click on the floor. She had been dressing in cute dresses and skirts that teased but didn’t reveal too much. Her favorite combo was a long black skirt with a slit on the side along with a tank top that showed off her cleavage with a cardigan to hide her shoulders. She always wore her pearls.

“It’s time for you to work little sissy bunny baby. Your hips are developed, your breasts as developed as they will be, and your face already looks feminine so we don’t have to do any work there. There are thousands of little perverts that will pay top dollar to see me humiliate you. Today is your first day in your big role.”

She shoved a o ring gag that had bright red lips on it making Billy look ridiculous with his pig tails. He pulled on the straps as he saw Alice turn a camera on after putting a mask on her face made of lace. A large Amazonian woman walked in and grabbed the camera

“You remember Helga? She’s going to be our camera girl and your handler. If you step out of line, she will grab her paddle. Understood?”

Billy shrank down and nodded. Alice looked into the camera and said

“This sissy decided to break my rules and try to run off with another mistress. Today, is part one of her making it up to me. Let’s clean this filthy whores holes.”

She giggled as she pulled out the enema kit making Billy squirm. He tried to yell but Helga grabbed his swollen blue balls making him yelp like a little dog.

“Be good or get the paddle.”

Helga whispered to him making him stop yelling.

Alice shoved two fingers into Billies ass quickly just to show the viewers how slutty Billy had been. They even had a shot of the camera of a close up on Billy while Alice finger fucked him showing how much he loved anal play. His eyes rolled back and his cage leaked as Alice made fun of him for being a sissy.

Eventually, she shoved the enema tube into Billy’s asshole making him squirm before she turned it on full blast making Billy yell out as he felt his stomach cramping. Alice fondled Billy’s balls as she said

“You shouldn’t have left me. You should have known better.”

She slapped Billy multiple times before starting to tickle him making his cramping much worse.

She grabbed his jaw and pulled his face to the camera saying

“Now, Billy, I want you to apologize to mommy and tell everyone how much you love me.”

Billy panicked as he tried his best to speak but the ring gag made it impossible

“Tsk tsk tsk. I don’t like your tone sissy girl.”

The enema was empty and Alice took the tube out before shoving a large butt plug into his asshole. She said to him

“You’re in timeout. Hold it, until I come back.”

She walked out the door and left him there for an hour before walking back in seeing Billy crying and squirming. Helga was laughing as she filmed every second of it. Alice let Billy down and he crumpled over holding his stomach. Alice said

“You have two options. Either be regressed back to diapers or be a sissy pain slut. Which do you want to be?”

Billy looked around quickly as he went back and forth of what would be worse. He knew what being diapered looked like but not what being a pain slut would be. He knew either way it was not going to fun. But he really hated being diapered. He took a deep breath and said

“Ummm….can I…can I be a pain slut mommy?”

Alice smiled and nodded her head before giving him a kiss on the forehead.

“Good girl.”

The camera turned back on and Alice held Billy’s chin in her hand saying

“Is my little slut done being a brat and ready to get out of her enema timeout?”

Billy nodded saying

“Yes mommy please let me out of timeout!”

Alice pushed around Billy’s belly making him whimper and cry before she slapped his tit and balls. She giggled and said

“Come here.”

They went to the bathroom where she made him beg for the potty on his knees making it hard to keep the enema in. Alice then face Billy toward the wall while he straddled the toilet so the camera got a nice view.

“Be a big girl and let out that enema.”

Billy cried a bit as he felt it rush out of him painfully but was relieved to have it out of him.

“Good girl! Now come on. Let’s make the ending of this video.”

Billy hung his head as he felt Helga drag him towards the newly built dungeon in the basement of Alice’s house. They went straight towards the sybian where Billy was thrown right onto it with no issues. The dildo was inflatable so Helga inflated it until Billy begged her to stop. His wrists and ankles were tied and he was left with a ball gag in his mouth. Alice walked over and said

“Ready to cum sissy?”

Billy nodded looking excited.

“Good. Let’s take that mean old cage off.”

Alice knelt down so he could see her cleavage and she slowly unlocked the cage taking part one piece at a time before slowly removing the deep urethra tube making Billy shake and squirm. He tilted his head back in relief but was immediately brought back to reality as he felt a sharp pinching around his penis. Alice had attached a spiked chastity ring called Kalis Teeth to Billy’s cock making Billy panic.

“All you have to do is cum. It’s not that hard sissy girl.”

Helga turned the machine on full blast making Billy hard almost immediately which made him cry and squirm. Alice began to slowly stroke Billy making his head feel like it was swimming. Helga took her place behind Billy and began to beat the soles of his feet with her cane making him squirm more his cock rock solid as Alice’s fingers felt like silk around his cock.

She slowly increased her speed making Billy excited but in more pain that ever as the skin of his cock got pulled by the teeth. Helga began to go back and forth from beating his feet to his ass before Alice said

“Either cum or beg me to stop. You have 3 minutes.”

Billy pulled in his restraints as Alice used her other hand to massage his balls. Shaking his head violently he decided he would try to cum

“PWEAVE BAY I COME!!!”

Alice laughed and said “

you have less than 2 minutes before you’re locked back up. It’s up to you.”

He concentrated but the pain get like it was too much. As the timer counted down from 5 seconds Billy started to give up hope and Alice let go of his cock right at 1. Billy cried as his cock twitched in pleasure but to everyone’s surprise, he started to leak out cum. It was very slow and painful for Billy but Alice laughed and laughed before blowing a kiss to the camera.

She stood up and said

“Welcome to your new life slut.”

Helga turned the thrusting mode on the sybian as Alice walked out the door.

“Have fun with Helga dear. I’ll be back after dinner to put you to bed.”

Billy screamed as Helga pulled out her paddle bag

“Your ass is mine sissy!”

To be continued.