Alice was having the time of her life with Billy. Months of training and she could see how much he drooled for his mother in law. Putty in her hands. She loves to tease him while she reads a book. A foot in his crotch, a bare leg through the robe showing, maybe she lets it fall open a little more showing some cleavage.
She had been unlocking him every morning and evening for some playtime. Of course it had to be humiliating in some way. Sometimes he’s tied to his high chair while she teased him, others it was just one finger running up and down his short shaft while he did his makeup. The diapers were pulled out a few times to make it nearly impossible for him not to cry as she rubbed him through the crinkly material.
One of her favorite rituals was allowing him to be in the room while she changed. Of course she has her bra and slip on before he comes in. He watches her out her makeup on and choose an outfit or maybe watch as she talks to a friend on the phone. One day she told him not to touch her and she called a friend on the phone while she sat in his lap, breasts in front of his face making him grind her lap.
6 months of teasing twice a day made his balls so full that he was finding himself grinding on anything he could reach. Last night was even worse as she took a pair of old panties and taped onto his face with the stained parts over his mouth and nose.
“Billy come here.”
Alice called out waiting in her room in a bra and slip. Billy still had the panties on his head so she took them off and asked
“Have a fun night?”
Billy nodded before rubbing his eyes.
“Good. Get undressed and kneel.”
Billy complied by sliding his princess panties off and his pink pajama top before kneeling. Alice pulled out a package that Billy assumed was some chastity cage. He didn’t know how much less of a penis he could have so it frightened him. An inverted cage is as invasive as it gets.
“Today we are going to the beach. I think your hips are filling out and your chest is coming in nicely. It’s time to show off in a bikini.”
Billy stared for a second before asking
“Developing? Mommy…mommy you haven’t been…”
Alice smirked
“Of course I have. I said you’re a girl. Be quiet. You love your hips and love your little boobies don’t you?”
“Mommy…that’s…. not the point!”
“You feel pretty don’t you?”
“Stop it!”
“No! You be quiet or else. Now. As I was saying before you rudely interrupted. You can’t be wearing bikinis with that unless you want to be arrested and we can’t give you boy shorts because you clearly have breasts.”
Billy felt nervous
“So mommy called some people and they gave me this.”
She opened the package and inside was a silicone thong that was shaped like a vagina. Billy looked confused before seeing what was happening.
“Please…please mommy…I…that’s too much!”
“Quiet. Now normally it doesn’t work with a cage but of course mommy pulled some strings and had one specially made that will make it perfect for you. Stand up. Yep, one leg. Good girl.”
Billy stepped in and saw the inside had two tubes. Interior and exterior. The exterior surrounded his cage and pulled it back while the interior was shoved inside the catheter of his cage. Alice pulled it up tight on him and had him do a spin. Of course she took some pictures and sent it to her daughter/ his fiancé.
“You’ll be wearing this a lot from now on. I’m tired of messing with your situation down there. Here. Check this out.”
Alice licked her fingers and did circles around the fake clit. Billy surprisingly felt it in his cage making him even hornier. Billy didn’t like the feeling or the absence of his penis but knew he didn’t have a choice. She slipped her fingers inside the vagina and said
“See, now you can have sex without ever unlocking again. Now go put on the bikini I laid out and Meet me back in here.”
He scurried off feeling himself and his new situation. He saw the frilly pink bikini and he knew he would feel ridiculous. It rode up his cheeks and he hated how little it was. Fully dressed though he walked back into Alice’s room where she laid out the diaper bag, towels snacks, and last but not least a hair brush. She stepped into the bathroom and tossed out to Billy her freshly worn undergarments and he sniffed and felt both of them.
Alice stepped out in a high waisted one piece bathing suit that was black showing off her figure. The back was open and the front had deep cleavage. Billy drooled and felt himself twitch and strain in his cage.
“Come on little girl. It’s time to go.”
She held his hand as they walked out the door they got to the car and Alice realized she had forgotten something. Billy tried to hide from the neighbors but the driver wouldn’t open the door until Alice said so. The neighbors said hi and asked Billy some questions which mortified him as he stood in his bikini. Alice finally came out and they entered the car leading to his next unfortunate event.
To be continued.
Source: reddit.com/r/Erotica/comments/12qb1kp/mother_in_law_takes_control_part_28_f58_m27_sissy
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