Feminine Change to sissy (Part 1)

Charlie couldn’t stop himself. The cage wouldn’t come off and his pent-up arousal could only build so much before he began to crumble. Eventually it happened, he found himself walking back to her apartment, feeling his cock tremble in its prison as he knocked on her door.

There she stood, still holding her sadistic smile proudly on her face as she looked him up and down, seeing his tense demeanor and knowing instantly that he was still caged.

“So, is my little sissy ready for her training?”

That’s how it started, his quick descent into feminization, flung into a flurry of changes to his wardrobe in preparation of what Megan kept describing as ‘The first test’...

Each day he would receive a new piece of paper beneath his door, all containing her terms. Megan’s demands were pretty simple at first, buying slutty clothes, a pink miniskirt, matching crop top, heels, the whole lot. At first he thought she was just a sick fuck was looking for a steamy night, but after receiving her next demand under his door, he couldn’t help but feel his blood run cold.

You will parade yourself like the ditzy sissy you are in the mall, at which point you will meet with a woman and the guy she has with him. You will then beg the guy to let you suck him off, or else the photographs will be released.

The immediate question of the photographs was answered, several snapshots of Charlie trying on his new outfits from what seemed to be outside his window. He could hardly believe the audacity of it all, crumpling the paper just after reading it. She wants him to degrade himself whilst she looks on from some vantage point?! As angry as he wants to be, there’s little choice for him in the matter. Looking back at the pile of freshly-bought clothes, he sighs to himself, preparing for the next morning with a good night's sleep.

Morning having come, Charlie prepares himself for what’s to come, noticing another note that had been slid beneath his door. It was optimistic to think she wouldn’t send another today, but as he read through her words, his heart sank.

You won’t be needing your tiny sissy dick today, so I left you a little present~! Open your door.

His hand beginning to shake somewhat, Charlie clutches the handle and opens his door, seeing a small box had been left at the foot of it, dreading what’s inside. It was dreadfully tense, each second going by as he strips away the packaging to reveal what’s inside…

Once inside, his heart somehow sinks even further, seeing that she had a cruel sense of humor as he looks over the ‘Tiny Boy’s’ chastity cage she had left for him. He took it out, peering over it at first, not understanding how his cock was supposed to even fit inside of it, then seeing another note that had fallen out from the box.

You’d better be wearing this, or you won’t be meeting the girl and guy, instead I’ll have you locked in a room with a bachelor party.

A cold shiver ran down Charlie’s spine once he imagined what she meant by that, and opted to struggle the cage onto his dick, taking the key to his original one she had left and slotting it in. There was a brief moment after uncaging himself, realizing he could just opt out now, run away and even call the police perhaps, maybe they would do something?

All of his thoughts were slowly drowned out by the overwhelming sensation tingling from his dick, almost as if it was naked and begging to be put back where it belongs. He looked back, remembering how she had beaten him down with her strapon, teaching him the lesson that he knew was true all along… and painfully pressed the new cage against his cock, struggling to have it fit inside, until finally…

Click!

That was it. Charlie’s heart was racing as he squirmed from the slight pain of being pushed so tightly into a cage that was easily half the size of his last one. He felt the arousal building, only to turn to an agonizing pinching sensation, his cock struggling to throb in the new cage. Trying to forget the subtle control of Megan that clung around his dick, he decided to get ready before he was late.

Getting dressed was difficult enough, not having worn these kinds of tight clothes before, it was a hassle even getting into them. It was a struggle, but he eventually slid himself into the tight, revealing outfits that clung to his body, emphasizing his already-feminine look, solidifying his place in the bedroom at a glance. Then came the worst part, the fresh look that he hadn’t felt before, the many eyes darting across his barely-clothed body, the lecherous gazes of horny passerbys.

This continued all the way to the mall, where he was thankfully able to blend in with the many crowds there whilst he searched for his targets.

He didn’t expect it to be so difficult to walk around like this. Not only were the heels difficult, but the constant assault of people brushing by him was obscene. His eyes dart open at the sudden electric sensation as a rather bold person cops a feel, pressing his finger against his ass as he walks by. Charlie tries to turn and confront him, but with a sea of people surrounding him, it’d be impossible to tell who it was.

Pervy bastard is probably grinning to himself right now…

Lost in a moment of anger, he must have looked vulnerable, as the same thing happens again, a pair of hands grabbing at his asscheeks, squeezing them roughly as he let out a whimper before turning around to nothing but confused faces once again. The shame and humiliation turns his face red, and he tries to back up against a wall to avoid any further assault as he searches for the woman. Though in his panic, he didn’t realize that it was a window he was pressing up against, and gave the customers inside a good view of his ass pressed against the glass as they cheered at the sight of him.

Almost an hour goes by of him stuck in this building, his cheeks had been spanked red beneath his miniskirt, and his nipples had been twisted more times than he could count. The worst part was, at this point, there was a deep part of him that accepted it. He no longer shied away from the crowds, instead he readily stepped into them knowing he was about to be groped, and even sometimes ‘forgetting’ to search for his target, instead arching his back as a silent invitation for any bold individuals to take their turn~

For a moment, he genuinely feels himself slipping away, he can see what he’s doing, but doesn't care about the consequences of it. The letter told him to act like an airheaded sissy, but he didn’t expect to enjoy it!

Then it finally happens, before he has a chance to slip any deeper down this pit of desire, out of the corner of his eye, he notices a woman clinging to a man, just as Megan said they’d be. It stings that Megan can manipulate him so easily, but nevertheless, he bite down on his pride and obscenely waved up in the air at her. He watched in awe for a moment, the woman’s face focusing to reveal who it was, Megan. She squints at the sight before her, unsure if her eyes are playing tricks on her or not, until finally her gaze widens in relief, and the look on her face turns to her usual smug expression.

“What the fuck are you doing?!”

She hurriedly drags the man over, eyes glancing across your outfit.

“You cannot wear something like that out in public, what are you thinking?!”

He knows she’s right and he wishes he could explain what’s going on to the poor guy, but instead is forced to screw his eyes shut for a moment, steeling himself for what’s to come. No matter what she had planned for him, he knew he’d have to withstand her sadistic humiliation if he wanted the pictures to stay secret.

“Oh my god! I’ve missed you~”

Once his arms were wrapped around her back, he looked back at the guy she brought. Not expecting to hear her sultry voice in his ear, Charlie trembles at her words.

“Suck him dry before the day is over, or else.”

Her words were emphasized by her knee pressing against his crotch, grinding gently, just enough to have him whimpering when she stopped. The worst part of her challenge was that Charlie didn’t feel the way he had expected. Whilst he should have been filled with disgust or fear at having to do it, there was a burning desire in his chest instead. With his face out of Megan’s view, he licked his lips in an obscenely seductive manner before blowing him a kiss and flashing him a wink. The act itself topped all from this morning, mostly because he knows where it’s leading, and shivers in a perverse arousal at the thought.