Alice giggled as she saw Billy blushing. They were in the airport waiting for their plane back home. Ella and Mark were sleeping next to them as Billy crossed his legs feeling the pad crinkle and the tampon shift around. Part of Billy’s punishment is that he is going to be on his “period” now once a month. He had to ask Alice to change them 4 times a day and if he missed the window to ask, Alice would add a week to his chastity sentence and spank him.

Alice made Billy wear a tight pink crop top and some white booty shorts that sometimes made his panties and pad peak out with a pair of pink flip flops. Some men were drooling at Billy while others laughed at him. Alice and Ella didn’t wear makeup but they made him wear a full face of makeup.

“….Mommy….can I change my tampon?”

Billy whispered to Alice.

“What honey? I can’t hear you when you speak that quietly.”

She smiled and Billy got frustrated as he said louder

“Mommy…can I change my tampon now?”

Alice laughed and said

“You’ve never changed it yourself. Why would you change it yourself now. Ask the real question.”

Billy hung his head before saying

“Mommy…can you please change my tampon…”

The man behind them chuckled making Billy feel self conscious. They got up and Alice grabbed Billy’s hand leading him to the ladies room. The stall was opened by the women coming out of it and she laughed seeing Billy

“Oh boy…”

Alice grinned and said

“This is my son in law. He’s a big sissy and is learned about menstruation currently.”

Billy blushed looking at this 30 something year old fit, tan, woman looking down on him.

“Oh shit…i heard about those…never thought I’d meet one.”

Alice smiled saying

“You want to watch or play with him a bit?”

She laughed saying

“Hell yeah I do!”

They all went into the stall and Billy wanted to run away but Alice said

“Do you need to potty first?”

Billy shook his head but Alice said

“Sissy…it has been a while since you made a pee pee. I think it’s about time.”

She began to push and tickle his stomach making the piss churn and feel like it was going to come out.

“Ok ok ok ok! I need to pee please!”

Alice and the woman laughed as he waited for permission.

“Go ahead sissy.”

He gulped and pulled down his shorts trying to hide his chastity cage but the woman said

“Hold on! What’s that!”

Alice giggled and said

“Show her.”

Billy hung his head and stood back up with his hands behind his back showing the flat urethral cage and the woman gasped

“It’s a chastity cage. He has no access to his little pee pee no matter how hard he tries. I have the key and he will never touch it without my permission.”

She was shocked.

“That’s crazy! But…he…you could say no?”

Alice nodded making the woman bite her lip loving the idea. She walked over to the sissy and began to gently fondle his balls and Billy moaned as he could see her cleavage. She saw him looking and said

“You want to feel them?”

Billy looked at Alice who gave him no indication of what to do and he said

“Yes please…”

She laughed and said

“Strip.”

Billy got excited but nervous as he took his clothes off.

“Shoes too.”

Billy looked at the floor and get gross walking barefoot on it but he did it. She then walked close to him so her cleavage pressed into Billy, her thighs against his, and her mouth almost touching his. She reached around and started pulling on his tampon string making him quiver and shake before she slapped his butt saying

“You have to say you’d rather see me naked then seeing your mother in law naked.”

Billy froze and looked at Alice who kept her poker face.

“Please miss…please…i….”

The woman smiled and said

“Tell me how much you’d rather be with a younger woman like myself.”

Billy felt embarrassed as he felt his locked dick leak but said

“I…I can’t…”

She laughed and said

“You’re sure? I’d take care of you…I’d give you blowjobs, i would let you cum all the time, and you can dress like a sissy while fucking me.”

Billy felt himself get harder in the cage and the thought of being able to cum almost sent him over the edge.

“I…”

The woman smiled and let the strap of her blouse fall to the side showing her shoulders and Billy whimpered

“Come on baby girl, you know you want me. Just tell her to fuck off and I’ll suck your dick right now.”

The woman caressed his balls making Billy squirm but Alice said

“I think it’s clear you’d rather have her than me. Have fun with your new mommy Billy.”

Alice turned and stormed out of the stall making Billy panic. He tried to run after her but the woman squeezed his balls saying

“Are you trying to run away from me?? No no no. It’s time for me to give you a blow job. Stay still and I’ll make you feel really good.”

Billy felt his panic rise but when he saw the woman kneel down in front of him he forgot about Alice. The woman started to suck and lick his cage which Billy was excited about but wanted to get a real blowjob.

“Miss…can…can I please have my cage off??”

She giggled and said

“Sure. Just give me your keys.”

Billy felt his heart drop.

“Wait…you don’t…you don’t have them..??”

She started to suck on his balls while shaking her head no. Billy turned red and felt the tears well up and he had to push her off saying

“I’m so sorry miss!!! I need my mommy!!!”

He took off after Alice and the woman ripped his shorts as he ran off so his butt was sticking out of them. He ran barefoot to the terminal where he saw Alice reading a newspaper casually.

“Mommy!!! Mommy wait!!”

Alice didn’t look up at the hard breathing sissy in front of her and said

“You made your choice. Go.”

He knelt down and kissed her feet saying

“Mommy please! I didn’t mean to!!! I got so confused with her touching me!!”

Everyone turned and laughed at the sissy who was begging.

“You only came back because of your cage didn’t you? Didn’t think that through at all did you?”

He cried as he said

“No!! I just can’t be without you!!”

She shook her head and said

“Well. If you need me so bad, then you won’t mind a spanking would you?”

He turned and saw everyone looking and looked back at her shakily saying

“Of course mommy….”

She grabbed him by the hair and pulled him over her knee slipping off her leather sandal without warming up his ass at all and began to wail on him. He cried out and started to squirm but she held him down tight before ripping his underwear and shorts off completely.

“OW MOMMY WAIT!!”

“No no. Bad sissys get spankings. You better be thanking me for taking you back.”

“THANK YOU MOMMY THANK UOU FOR TAKING ME BACK!!!”

His ass was a dark red by the time she was done spanking him. She made him put on the short pink skirt with his princess panties and a large pad before bending him over again and shoving a tampon into his ass.

“Be a good sissy and your punishment will only be for a few months.”

Billy got nervous

“Months??”

“You think one spanking is sufficient for embarrassing me like that?”

Billy hung his head as they lined up to board the plane.

To be continued.