Christian stopped as he reached the edge of the baseball field. The game going on had the fans and players focused on the diamond, not on the sissy creature standing near the parking lot.
Just moments earlier his sister had dropped him off, telling him that he needed to sit down in the stands and to be a good girl until the end of the ninth inning. "Make sure you answer any questions you get honestly and pose for pictures if anyone wants to take them," she had said as the van door slip closed behind Christian with a thunk. "If I hear from anyone else at the game that you weren't the perfect little dolly, it will be sandpaper time when you get home." She laughed as she put the van in drive and pulled out, leaving Christian frozen in fear until the thought of another sandpapering pushed him into action.
That damned sandpaper. About a year previous, Christian had been caught looking at trans girls along with sissy and diaper fetish porn by his ultra-conservative and very religous mother. She had broken down crying at what a shame her son was and had threatened to kick him out of the house. Christian was initially thankful when his sister had stepped in and convinced their mother to let him stay. "Where will he go mom?" She had asked. "He's 34 and only knows how to play video games and jack off to porn. No one is going to hire that loser."
Her words had stung but she did have a point. His life had been going kind of terribly lately and porn and video games were a regular outlet for him. Probably why he'd gotten so comfortable to the point of easily being caught. So he listened as his sister outlined a plan to let Christian stay at home, but under their terms and making sure he couldn't 'sin' any more with his masturbation habits.
So just a few weeks later his life was already completely flipped on its head. His sister still lives at home but not because she had to. She made very good money working for a tech startup in the cosmetics field. She had matched Christian down to her office the same day he was caught and ordered a full makeover done on him. "You get to be the pretty little sissy that you obviously want to be, and my company gets valuable Intel for future projects." The team had done micro surgeries on his face, tapering his jaw, shaving down his nose and Adam's apple, sewing thick fake eyelashes directly to his eyelids, and more. A cosmetic artist was brought up from the fourth floor to do tattooing and he was given a permanent soft makeup look with eyeliner, mascara, lipstick, and blush all being tattooed on before a stylist came over and did his hair into pigtails.
Next they stopped off on the second floor where his sister ordered a doctor to give him large but not ridiculous breast implants. The company has some amazing tech as they didn't even need to put him under and he walked out with DD tits swaying on his chest as he struggled to adjust to his new center of balance. Then it was back up to the sixth floor where his sister had gone over to a small team working in what looked like a metal fabrication shop and whispered excitedly with them before coming back to Christian and holding out her hands to show off what she had.
Up until this point Christian had pretty much gone a long with everything with just token resistance. He had long struggled with being secretly trans and having an excuse to do much of the physical work of transitioning from male to female, even if under the guide of it being a 'punishment' was too good an opportunity to pass up. But now as he looked down at his sister's hands and saw what she had, he began to back away in fear. "Hold her still," was all his sister had to say and Christian found two burly men at each arm, keeping him from running as she stepped forward with her prize. It was a custom chastity cage. The cage portion was nearly flat leaving any wearer no room for erections at all. The ring was fairly small and he worried that it might not even fit him. The lock on top was streamlined and nearly hidden. But what scared him the most was the tube coming out of the cage. It was thick and long, obviously designed to go up his urethra.
He whimpered as his sister reached him and slid his pants down, revealing his fairly unimpressive member. "The team here normally works on new piercing designs and new belt bucks and accessories, but Cheryl has been tinkering on this in her free time. It was supposed to be for her boyfriend but she was happy to give it up to be put on you." His sister prattled on like this was totally normal as she slipped the ring over his cock and balls. He had been right, the ring was a bit small and it made his balls plump up from the pressure. Next she slip the tube into the top of his cock and right when he started to protest, she thrust the tube in and quickly got the cage into position before locking it. She tucked the key into her pocket and simply laughed as Christian winced in pain from the pressure the tube was exerting on his cock.
When they got back home mother was shocked to see his transformation but she approved of it and also what was to come next. His room was gutted and over the course of a few weeks it was transformed from a stereotypical guys room into a nursery fit for a baby girl. A large custom crib and changing table, a rocking horse and highchair, a play space. Everything painted in soft whites and pinks. Once it was all set up his sister had brought in the diapers and dresses, telling him that he would never again be without either. "Say bye bye to your boy clothes and bye bye to the toilet, loser," she has said in an almost sing song voice, so pleased with herself and how quickly she had brought her brother down.
At the end of the first month his sister had approached him in the evening and pulled out the chastity cage key. He was excited until she had explained how his releases were going to work. "You will have one chance to get an orgasm per month. If you are a PERFECT little baby girl, you'll get to make cummies." She punctuated this statement by sticking the key into the lock on his cage as he lay on the changing table with his hands secured down by bondage straps. "But...." she continued, pulling the key back out without actually unlocking him, "if you are naughty. If you break any rules. If you refuse any orders, you'll get sandpaper instead." She held up a piece of sandpaper and pressed the teeth of the key against it. "You didn't thank me or mom for your transformation or for giving you the life that you obviously wanted, so this month will be a sandpaper month." And with that she quickly pulled the key along the sandpaper before putting the key back in her pocket and continuing the diaper change. "How many times do you think you can get the sandpaper treatment before that key has no chance of working in that lock and you're stuck permanently caged with no hope of ever cumming again?"
So now here he was, on the edge of the baseball field ten months later. In that time he'd gotten out of the hated cage 4 times and the key had been sandpapered 6 times. Just last month her had managed to secure an orgasm which he had ten minutes alone in his nursery to jerk himself off with nothing but his imagination to fuel him' before his sister returned with the cage and locked him back up whether he managed to cum or not. But even then the key had felt stuff in the lock and his sister had to force it to turn. How many more sandpaperings could he afford? He had to be a perfect sissy baby or else he'd quickly never have a chance at cumming again.
With a deep breath he stepped forward towards the bleachers, determined to get through this humiliating ordeal and be a good girl......or else.
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