Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereBilly's diaper was pulled down to his knees and his dress lifted up to expose his butt while he lay flat on the table with ankles and wrists tied to the corners. His tears slipped down as he tried to beg through his cock shaped pacifier to not be spanked.
Alice was walking back with some implements she ordered earlier this week: a thick and thin cane, a narrow and wide wooden paddle, butt plugs, vibrators, and much much more.
She pulled the thin cane out first and rested it across his butt cheeks. He squirmed and she laughed. He heard her in the kitchen and it sounded like she was peeling potatoes. Her feet slapped the ground as she came back to the table
"Billy Billy Billy Billy. You seem to think you can do whatever you want still. Playing with yourself? No no no. Very very bad sissy. If you need some sexual relief, you have to beg mommy."
She picked up the cane and said
"So beg..."
The first hit of the cane came down hard without warning. Billy cried loudly pulling against the restraints and Alice kept a steady pace repeating herself,
"Beg me, Billy. Beg me to give you some relief."
The welts were quickly forming before she stopped after what must have been 30 strikes. She started to pull his butt cheeks apart and shoved something in Billy's ass. She taped over it so it wouldn't move and to Billy's shock it started to burn badly. It was a pain he never felt before. It was like fire ants were eating his colon. He screamed and screamed but Alice said again
"Beg mommy to relieve you."
Muffled screams were unintelligible. The thin paddle was brought out and she began to beat his butt with it relentlessly. His begging sounded like, "MMM BWEEEE WEEEWEEFF MMMMEEEEHHH!!!!!! MMMAAAMMMEEE!!!"
Alice quickly switched to the heavy paddle and made him sob as he kept trying to beg her. After seeing his butt turning purple she set down the paddle and started to move the piece of ginger in and out like she was fucking him and twisting it around to make sure it reached all of his insides.
He writhed and twisted trying to get away but it was no use. His sobbing made it impossible to talk.
She started to tie a thread around his balls before pulling them up and tying them to the gag making his balls exposed. He whimpered and tried to kick but the restraints were too tight.
He heard her laugh and she picked up the thin wooden paddle.
"I warned you about touching yourself."
With that, she started to hit his balls hard with a consistent rhythm over and over again. His shrieks were intense as the ginger was twisting inside him and his blue sensitive balls were being made into mush it felt like. As the beating continued, Alice noticed some fluid leaking from the cage.
"Oh sissy, is the ginger hitting your prostate nicely? You like it?"
She pushed her finger on the ginger to make it go deeper while she spanked his balls. He was a sniveling mess. When she finally stopped, he just lay there shaking.
"I bet now you will think twice before trying to touch yourself again."
Alice tapped his balls making him jump.
"Now you'll be in timeout for the next hour with your friend that's resting in your butt. If I hear anything other than an apology then we will have to start your punishment over. Understand?"
Billy nodded quickly and rested his head on the table as his hips and butt wiggled around trying to get the burning to stop.
Alice made him wait the next hour making sure to avoid the room altogether so he would be completely alone. Billy found himself crying feeling the disappointment he made Alice feel in him for touching himself. He tried to knock himself out of the thought process but it kept coming back.
Alice walked in to him crying and it made her smile. She untied him and pulled the ginger out before leading him to his bedroom having him lay face down where she applied some lotion to his bottom before saying
"Are you feeling guilty sissy?"
Billy sniffled saying
"Yes, mommy...I don't want to disappoint you..."
Alice smiled saying
"But you also kind of get off being humiliated don't you?"
Billy blushed and wiped his nose with the back of his hand looking away.
"You like to be bullied and not quite measure up. That's why you dated my daughter. She was out of your league and you knew it. You were insecure and you found it exhilarating."
Billy thought for a moment realizing she was right.
"You protested in the mall but you loved being pathetic. You were so hard that it left marks on your little clitty cock. You like to be bossed around by me, to wear these ridiculous clothes, to be made into a sissy. You want to be mommy's little slutty plaything."
Billy couldn't believe how right she was. He loved and hated being embarrassed. She called him a pervert the first time she met him, maybe he was a pervert? He felt so much shame as he buried his head into the mattress.
"Don't hide away from me. No need to feel ashamed. It is just who you are. You want to be humiliated by mommy. You want to be humiliated by Ella. You want to be humiliated by your sissy sitter and anyone else who is willing to put you in your place."
Billy remained quiet but looked at her. He slowly nodded his head. Alice nodded back saying
"You just need to be trained. You will resist, but I will not let you fail to be who you are and I will not let you keep Ella from being the domineering woman she is, do you understand?"
Billy nodded his head and felt his cage pinch him more.
"Come here."
Billy sat up and watched Alice unlock his cage and put him over her knee. He squirmed, nervous that he was going to get spanked again but she said
"Stay still. Your punishment is over for today. I need to reinforce your realization from today."
She lifted her skirt up so the top of Billy's cock could feel her warm thigh making him hard as a rock. He heard her squirt some lotion in her hand and she began to rub the underside of his cock making him involuntarily hump. She kept her hand still and said
"Go on. Cum like the sissy you are, humping my hand instead of fucking a pussy like a man would."
Billy humped for maybe thirty seconds before he hastily called out in a squeaky voice
"Mommy! Mommy please can I cum??"
She said in a stern voice
"Yes sissy, you may cum."
He cried out in a high pitch voice as the first spurt shot out onto the floor but then felt no pressure any longer as Alice pulled her hand away ruining his orgasm making him whimper. Alice said
"Now now sissy, don't be greedy. You got caught touching yourself, did you really think you were getting a full orgasm after that? Tsk Tsk. No no no, you get something for at least realizing what mommy is doing for you."
Billy slowly seeped out the remnants of an orgasm before she smacked his sore bottom and commanded.
"Clean up your mess with your tongue, then go do your chores."
She locked him back up in his cage and then walked out slowly making Billy feel like he was ready for round two if it wasn't for his cage.