His ass was still bruised from the spanking from the week before as Alice fed him his afternoon bottle. His fresh diaper crinkled as Alice teased his locked penis with her fingers. Her index finger ran over the flat head before gently caressing his balls a few times before going outside the diaper to rub it.
Weeks of relentless teasing made his balls constantly ache and leak. He found himself looking forward to his mother in law changing him since he knew she would at least touch him. The flat cage made it nearly impossible for him to get close but she was so good at dangling his orgasm in front of him that a couple of times he thought he would blow.
Billy bucked his hips at her hands making Alice smile. As he stared at her cleavage, Alice said
“Ok baby girl. Tonight, Mommy has a date to go to. That means i hired you a babysitter.”
Billy was shocked. He almost shook his head but thought better of it.
“I debated who to hire for a while. The lifeguard you always drool over, your prom date from high school, your own mother, maybe even Frank or that young man you sucked off at the waxing place. Mrs. Lollar was very interested but unfortunately she had plans.”
Alice kept her smile while Billy tried to figure out who he is going to be embarrassed by.
“Here’s the deal. If you’re good, then you’ll get a big reward. If you’re bad then you’ll be punished much worse than you’ve seen before. Let’s see…what would motivate you…”
Billy’s heart raced before Alice pulled her necklace out of her shirt.
“What about a release?”
Billy nodded quickly as she laughed.
“If you’re bad then all bets are off. I’ll make your life a living hell. Understand?”
He again nodded quickly as he finished the bottle.
Alice stood up and placed him in front of the door with some dolls in his pink dress. She put some blush on him and took his picture before saying.
“Don’t move. She will be here soon.”
He stayed put as she got ready for her date. His mind wondered trying to figure out who it was. She knew that Billy hated anticipation more than anything. The door bell rang and Alice quickly came to the door greeting a large man who gave her a kiss before looking down at Billy.
“Is that him?”
Alice nodded. He snorted and grabbed Billy by the wrist before quickly turning him around and pulling his diaper back, checking for a mess. He slapped the diapered butt and threw Billy back on the ground.
“Good girl. No messes for daddy to clean up.”
Billy shrunk down and felt his cage twitch making him blush even harder. The man’s suit was clearly expensive and he has clearly known Alice for a long time. Alice bent down and pulled out some pink lipgloss and put it on Billy making him feel even smaller.
The door rang again and Billy looked worried. As his babysitter walked in, his heart dropped. It was the religious freak from his high school he used to bully. Constantly calling her Virgin Mary, lifting her skirt, or, the worst one, putting a virus on her computer that flooded it with porn and had the sound on full blast in the middle of class.
The worst part about Rachel was how attractive she was without trying. Simple skirts and dresses showed her tan, toned legs and her ass could not be hidden.
Rachel laughed and said
“Hey little girl, remember me? The Virgin Mary! We are going to have so much fun tonight you won’t be able to stand it!”
Alice giggled and knelt down one more time putting his face in her hand saying
“Billy. She has no restrictions on what she can do with you. If I hear even one millisecond of a hesitation came from you, then I’m going to make sure you never cum again do you understand me Billy?”
The intensity at which she said it made Billy nervous. She only used this tone when she meant business. Last time he heard this voice the Gardner was deported.
Billy said quietly
“Yes, mommy…”
“I couldn’t hear you baby girl.”
“….Yes, mommy!”
With that Alice kissed his forehead and stood up turning so her ass was in his face making his cock strain.
“Rachel, she’s all yours. Just remember the incentives we discussed and you’ll make more money here than you did all of last year teaching.”
Alice kissed Rachel on the cheek before Daddy grabbed Alice’s ass as they walked out the door. Rachel stood over Billy for a second before walking towards the living room saying
“Come.”
As Billy started to stand up she said
“Excuse me? Baby’s crawl.”
He frowned and then went on all fours crawling behind her.
“I don’t like your hesitation baby girl…”
“I’m sorry Rachel! I didn’t mean to…”
“Quiet! It is Miss Rachel to you and I have every intention to be your babysitter for the foreseeable future and you will not ruin this for me.”
She sat on the couch snapping her fingers. Billy quickly made his way over in front of her crossed legs.
“You should have been nicer to me. Now it’s time for payback.”
The door opened and Billy was confused but a man about his age walked over and said
“Good evening Miss Rachel. I apologize for the delay.”
“Oh no worries. It’s your big night, I’m glad you took the extra time to make sure you were prepared. You may go change.”
A few moments later he came back out in a frilly sissy frock with a full face of makeup and heels. He knelt down next to Billy and Miss Rachel said
“Billy, say hello to Sarah. My sissy boyfriend. He’s earned an orgasm and guess who is going to help him with that.”
To be continued.
Source: reddit.com/r/Erotica/comments/11tpbcu/mother_in_law_takes_control_part_16_sissysitter
Updateme