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A teacher is blackmailed by a student.
"You can pay me for those pair, they belong to you now." When she explained that they were going to the mall to buy a more complete wardrobe for her sissy daughter, James finally got his nerve.
"Okay! Mom! I get your point! It wasn't anything! I'm not gay, I don't want to wear women's clothes I was just-" She slapped him across the face hard.
"Listen here you little pansy. It's bad enough you have to ruin my favorite piece of nightwear, you are not going to give me sass as well! Do you want everyone at your school to know that you're a filthy pervert who plays with his own Mother's underwear?"
"NO!" He shouted, falling to his knees again. And so they'd spent the day at the mall, going from store to store, trying on endless shoes, blouses, dresses and corsets before ending the day with a mani-pedi/tanning session at the salon. The embarrassment was almost too much for James to bear, but it was better than what his Mother had threatened to do if he didn't cooperate.
That night, James had to tear down his room completely, getting rid of all his male clothes, video games, books and belongings. He put new pink barbie-themed sheets on his bed and was getting into his new purple footie pajamas when his Mother came in with a small plastic device in one hand and a key in the other.
"Not so fast, Jasmine. We need to put this on first." She said, pulling his soft, small dick into the plastic tube and fixing the plastic ring around his balls.
James tried to recoil. "What are you doing! And my name isn't Jasmine!"
"It is now, sissy. And this is your chastity cage. It's going to keep you chaste and honest tonight and every night from now on. I don't want you getting horny and erect, being surrounded by all your new girly possessions. You're my good little virgin girl and you don't need any more dirty perversions to reveal to your school cums do you?"
"No..." Jasmine whimpered, defeated.
Today would be the hardest he knew. Today was so unfair. But if he didn't do exactly as she had instructed, the entire college might find out about what his life at home was like now.
Pulling his skimpy pink thong over his tiny chastity cage, Jasmine remarked how feminine and girlish she actually did look, done up as she was. Maybe Kim wouldn't immediately hate and reject her, maybe she'd find her attractive in a new way. 'Unlikely,' he thought, pulling up his sheer stockings and hooking on the bra with realistic breast forms he'd had to buy with his college fund.
The maid uniform she was making him wear was outrageous. It didn't cover up anything, the apron left his fake breasts spilling out over top of it, and the skirt ended well above the half way mark of his exposed butt, allowing everyone to see his little thong and cock cage. The 6 inch pink heels were wobbly to walk in at first, but a few hundred laps around the pool had taught him how to strut in them properly, wiggling his butt to stabilize himself. His outfit was completed by a ridiculous tiara which was shaped in the word 'COCK' bordered by big red and pink hearts, and comically small pink duster that he had to hold between thumb and forefinger.
Before inviting his girlfriend Kim to come by, his Mother mused on what might be the most humiliating thing to have her walk in on him doing. She considered making her new maid rub her feet and massage them thoroughly. That would be cute for Kim to see - her loser boyfriend done up as a french maid rubbing his tired mum's feet like a good boy.
Or maybe it would be better for her to find him in his proper place in life - scrubbing the toilet on his knees. She'd certainly have him doing that quite a bit from now on. Whenever he didn't have more important chores to keep him busy he could always work on polishing that toilet.
She finally settled on having him kneel on his knees up in the living room where his new 10 inch black dildo was fixed to the wall.