Sir Knows Whats Best For Cassie

An older man in a navy suit called out to me. He'd followed me home most of the way, and I'd almost turned the corner, feeling his eyes burning my back.

"Huh?" I turned, half ready to ignore him.

"Hey. This is you, right?"

He was holding up a photo on his phone as he approached. I squinted and let him walk closer, taking a few moments to process what he was trying to show me.

It was taken several minutes ago, and it was me - or at least my midsection. I was asleep, slumped over, but with someone's hand reaching out to hold up my bus pass.

And that bus pass was right next to the love-hearts that were sticking out of my waistband, my shirt tugged up and away. The lace of a black bra peeked from above, to boot.

"... Uh"

I choked for a moment, trying to think on the spot. There it was, my full name and face, my date of birth (I'd turned nineteen last August) right next to the crimson panties and glossy black pantyhose I'd chosen to wear today, for everyone else on the bus to see - at least I hope they didn't, I'd woken up still clothed as far as I could tell.

"It is, isn't it?"

The man didn't move, but my eyes darted from his face to the picture and back. What the hell was he doing?

"N-no... I...?"

I swallowed hard as he nodded, turning his expensive-looking phone back and tapping a few things.

"Okay." he muttered. "I want you to do something for me."

"P-please, whatever it is, please just..."

"Quiet". He said, with an edge to it. "Take those off. Now."

"I-"... I just couldn't think. Was this guy crazy? "No, I can't!"

He scoffed. "Yes you can. You'll do it, now, or else this photo will be sent to your family. Do you understand?"

"You can't-" I hissed, looking around for someone, anyone, to help. "Please!"

"I can. Isn't this yours?"

He held the phone up again, and indeed there was my profile picture and all my friends and family listed below. In a panic, I froze. My heart slammed in my chest.

"So, I'll ask you again. Take your jeans off." He pointed.

Forcing myself to take slow, deliberate breaths, I stared at him for several seconds. But it seemed like he was serious, and I wasn't close enough to snatch that phone and run. I slowly nodded and reached down to undo my zipper.

"That's right." He said under his breath, switching over to the camera again and stepping back.

After wiggling back and forth for a moment, then struggling to pull my jeans over my shoes, I stood back up with a glare that could kill. I was extremely tense, glancing around occasionally to make sure nobody else was coming - but thankfully (or not) this was a side-street backed behind several houses, so we were alone for now.

"Alright. Now unbutton your shirt."

"P-please..." I mumbled, ice in my stomach. I was already showing way too much to the whole world. But he just waved his hand in a 'get on with it' motion, and I grit my teeth before slowly undoing the buttons one-by-one. And my lacy bra revealed itself to the world.

There was my pale, skinny body exposed, trapped inside unmistakably feminine undergarments, and this man was taking several pictures of it all. I prayed he couldn't see the lump my chastity cage made underneath.

"Good. Very good, yes..." He finally stopped, and my shoulders slumped. "You can put them back on now."

I bit my tongue to tell him to fuck off, and hastily dragged my jeans back on before doing everything back up. He was busy tapping away on his phone, and I was still in great fear that he was about to just dump my secret to the people I really, REALLY did not want to know it... My life would be over.

"D-don't send those, I swear to god..."

He looked up. "Oh? Or what."

It wasn't a question, it was just a blunt statement.

"I won't post them, but please do everything I ask you to. Got that?" He pocketed the phone containing the blackmail, and folded his arms. He must be some kind of rich, because a fancy watch slid out from his shirt cuffs.

"I..." Well, what else could I do? "Like what?"

"Everything. I have lots of things for you to do, or to wear. You seem to be used to it, right?" He pointed down at my crotch, and I recoiled a little as if he'd reached out to grab me.

"No! I mean, I'm... It's not like that, I..."

He made another scoffing noise, unconvinced. "So how long have you been locked for this time?"

I pursed my lips, not keen to give the real answer. "Ff-three days."

"Oh, really." He had a damn smirk that I couldn't help but look away from. "That's not very much. Where are you headed?" He looked down to check the time, then back to me.

I shook my head and pointed. "I'm going home, actually..." I quickly fabricated a lie to back it up; "...and I already said I'd be there for dinner. So, uh..."

He brushed it off, just as quickly. "Then text to let them know you'll be later. Come with me."

He turned to walk back down the path, back to the car park. I was left with a dilemma: run and hope to god he was bluffing, living in fear, or...

In that moment, I took a sharp breath... and followed him.

---

Once he'd lead me into his car - a fancy BMW, as it turned out - I was there in his passenger seat, squirming. I sat my shoulder bag over my crotch as if it'd obscure my secret more effectively, but that ship had sailed.

"Tell me. When did you start?"

I looked to him, then back at the road again, resigned. I might as well go along with it for now.

"Okay so, uh, I guess. When I was younger. I guess, I was... I uh, I borrowed a pair of pantyhose from my older sister." The shame was like tar in my throat, but I kept going. "It made me happy. I started borrowing a few more things, and I even took some clothes from a neighbour to wear, but eventually I didn't want to keep sneaking them back to where they came from... so I bought my own."

He nodded, as if this was just any old conversation. "Okay. Then?"

"I uh, I mostly went to stores late at night. I hid it in a drawer in my room. Mostly hose, underwear, a skirt and a top."

"And the cage, when did you get into that?"

I guess he spotted it after all. "Well, uh. That. It was a friend online who introduced me to them, and said I could try on a spare one of his, and it just... uhm, yeah. It fit."

I rubbed my legs together, regretting everything.

"Where'd you keep the keys?"

"Uh. Just in my wallet. I don't, I haven't... done much with them." Another little lie, but I didn't want to give him any ideas.

"W-what are you gonna do?" I asked back, to stem the tide of probing questions.

"Hm? Well, it seems like you do things that make me very interested in you. You know what it's like wearing women's clothing, and seem to enjoy it so much you wear it going to college. Tell me, in school, how much do you want to wear the girl's uniform instead of the boy's?"

I looked down, a little red in the face again. "Uhm... I... sorta..." It was unconvincing.

"Mmm, that's good then." We'd travelled pretty far by now, and I was starting to get even more anxious about getting home some other way.

"Let me make myself clear. You will do what I say, or else everything gets sent to your parents and your friends. I will tell them you exposed yourself to me, for a sexual thrill, and report you to the police."

What the fuck? My fingernails dug into my palms. "Wait- That's not true!"

"-You can prevent this..." he continued, unwavering. "... By doing as I ask. Got that?"

It was quiet for a minute, other than the sound of the road passing below. I just stared out the window and wrestled with the situation mentally, looking for ways out. Could I convince my parents it wasn't true? Could I even face them after being found out? If I threw away my girly clothes and toys in time, could I say it wasn't me? It was all too terrifying to face.

"We're here."

Interrupting my thoughts, we'd stopped in the driveway of a stately two-story house. The message I was getting was that this guy had money, but didn't go overboard with particularly flashy displays of it - just the 'normal' sort of obnoxious rich-guy stuff. We stood in front of the door and he fished for a key before turning to face me.

"Now. You can leave at anytime, and I'll take you back. But the moment you do, everything I described will proceed, and everything will be made public. Okay? So you're making the choice to come inside."

I gave him a withering look, as if it was any sort of real choice. "Fine."

"And one more thing. You will only address me as 'Sir'. I will decide your name later, once I've had time to get to know you. Okay?"

"F-... Fine, Sir." The word was bitter in my mouth.

---

Down a sparse hallway with shoes lined up on one side, he gestured for me to take off my sneakers. Wasn't much point hiding my feet now, I guess.

Once that was done, he brought me upstairs and turned around into a carpeted bedroom, another clean and modern space that had only a few human necessities lying around on bedside tables or a desk.

He closed the door behind me, and pointed to the bed for me to sit.

"I'm going to get you out of those clothes now."

I didn't respond, knowing the answer if I objected. So I let him approach and begin. With an unexpectedly delicate touch he undid all my buttons, sliding off my hoodie and shirt before draping them over a nearby chair. Next was my jeans, tugged and pulled until they slid past my ankles, and those too were neatly put away.

Now I was there in nothing but girl's underwear and a chastity cage, on a stranger's bed, unable to get out. My throat was dry and my heart kept ramming against my ribs, but I stayed still, praying this guy would stop.

And he did - he just stood for a second, taking it all in.

"Not bad stuff. Cute." He ran a finger around the shoulder strap of my bra, then his hand went on my knee, feeling the black fabric I was trapped inside of. "Such a shame to hide it from the world when you look this good..."

A few more seconds went by as he caressed my legs and feet, down and up, before he reached for my waistband and I instinctively tensed up, his hands about to breach a final barrier. With only a moments hesitation as he looked me in the eye, he continued and pulled down the waistband, rolling slowly down my thighs as I shuffled and let him pull them off completely.

He was so close now, as he reached behind to unhook my bra, letting it fall and slide down my arms. And finally, the pink panties I treasured so much, the ones I felt the most devious in, he began to work down my thighs until they too came off.

Now I was laid bare. A small pink plastic cage between my legs was the last and only thing. It was kinda cold in the bedroom, as my toes curled and my lips pursed.

"Very good." He drank it all in for a moment, my shaved-hair body left helpless. Then he fetched my wallet from my hoodie and opened it, handing it to me.

"The keys."

I gulped, fearing this moment especially. My fingers dug inside, and out came a familiar rigid metal shape - a key, unassuming but very important to me. Before I could even comment, he grabbed it out of my hands and looked it over.

"One of them. They come as a set, don't they? So you still have one at home, right?"

I nodded. I figured it was a wise move. "I kept it under my bed just in case."

He turned it over in his hands for a few moments, before kneeling down and approaching again. "Legs apart."

This was even worse. In some twisted way I felt protected by the cage, and now he was reaching in to slot the key into the side, ever-so-gently. The key turned, clicked, and then was pulled back out with the brass lock mechanism on it.

And that meant the two pieces of the cage were free to detach, the ring was free to work its way over my testes, and after two weeks of restraint my cage was taken off.

It felt so weird. Someone else touching things that were sacred. At least I'd been diligent keeping clean, shaved and moisturised down there. He gave my member a few looks over, lifting and checking.

"Okay. Nice and small. You already know that you are never to pleasure yourself with that. And trust me, I will know..." He placed my cage on a side table. "So to make extra sure, I'll give you one that's much better... I can see you're not pierced yet..."

He left, and I was there for several moments just breathing and clinging to the sheets for stability. Could I run in time? Probably not. Fuck. I hated how much my cage twitched when he touched me.

Before my feet got any colder, he returned with a small bag, from which he withdrew some clanking metal pieces. It was a smaller cage, a shiny steel one I'd seen before on the web, with only a nub for the penis to be pushed into. I shivered as it dawned on me that he wanted to put me into it right away.

At least I was almost completely limp, all the blood rushing around my body, too busy being scared to be horny.

"Hold still." From the bag he withdrew a small bottle of lubricant and another set of keys. The stainless steel felt like ice when it touched my delicate areas, and I winced as he began to work it over my genitals, the lube helping it slide and shift until the metal ring reached the base of my shaft - it was tight, almost too tight, but the cold probably helped shrink things into place.

Now came the front cage part, and he took his time lining it up and applying pressure - it looked like my member wouldn't fit, but with enough patience it compressed and squeezed.

"Wait-" I took gasps as it came closer to mating with the ring, praying it somehow wouldn't fit and he'd have to give up - but once more at the edge of becoming too tight, the metal parts met and the cage was fit snugly.

"Gnnnh..." I let out an uncomfortable groan, expecting pain - but feeling only pressure and cold. And the chill was already beginning to let up as my body warmth spread to the cage.

"Good." I could feel his breath on my stomach. He reached over on the bed, picked up the fresh set of keys, and inserted the appropriate brass lock into the mating hole. I could feel it slide in and drew a breath to object, to say "no!", but nothing came in time - he'd turned the key, a click happened, the key was withdrawn, and the lock was secured.

He let go, and the cage hung in place. It was noticeably heavier and clung much tighter than mine.

"God..." I said under my breath, staring at the little prison. My member twitched involuntarily, but there was nowhere for it to go whatsoever.

"Now, say 'Thank You'." He clasped the keys in his hand, his expression giving nothing away. But it was hard to imagine he *wasn't* enjoying this horrific procedure.

"I-..." I hissed a sigh. "... Thank you. S-Sir."

"Good. We'll see how that one suits you for now." He started to turn away and I instinctively reached out, for the keys, for any sort of mercy - but he just scoffed again and jangled them in his palm.

"This is not negotiable. You will be caged from now on, at all times. You should be used to it, yes? No need for spares or releases."

I stopped myself snapping back and just rubbed my bare legs together, getting chilly. Noticing, he pocketed the keys and walked to the cupboards, rifling through a set of drawers.

"You'll wear something else home today."

I glanced over at my clothes, pantyhose and bra top of the pile on the chair - wondering what could be worse to wear than these? He turned and walked back carrying things that made my heart skip and my fingers clench the bed once more.

Schoolgirl uniform.

He even had the specific tie and crest of my old private school - it was unmistakable. It was as if it was totally prepared, and I noticed a few different sizes still hanging in the wardrobe. Next to the sharp-cut pleats of a grey miniskirt was a folded white blouse, and a matching short-sleeved blue sweater emblazoned with the school's preppy logo. The textbook uniform of the junior girls, one I'd seen before but never got to touch... Maybe this wasn't so bad?

"Something appropriate, yes? If you haven't already worn it in the past..."

I shook my head, and he laid everything flat on the bed. I resisted the urge to run my hands over it right away, and instead noticed the lack of panties to go with them. A strange omission for some guy who seemed to obsess over details.

"And there's something else."

This time, it was a drawer under the bed. From there he brought out something bulbous and black, and then came a flat rectangle - pink, but plastic and thickened, love hearts running around the edges.

It wasn't until he unfolded the latter object and brought it over to me that I realised what it was - a diaper. A big, thick, girly diaper. And with it came a big, threatening-looking buttplug.

"N-no way!" I objected, recoiling back onto the bed. This was far beyond anything I'd ever looked into, or dreamed of, or wanted. But he didn't seem to care, he just laid the items out next to me and stepped back to take his phone out again. The diaper was laid out like a trap waiting to spring, and the plug's thin stem held up a weighty, dense head that I worried was beyond the size of anything I'd tried before.

"Yes." He pointed to the bottle of lubricant, and the plug. "This first."

"Please, I can't!" I was almost in tears. "I've only ever... I mean, small stuff, not like... this!"

"Then you will take it slowly. Let me help."

After he'd taken a few more photos of me in such a state, despair in my eyes, he knelt down again and motioned for me to lie back. I scrunched up my toes, indignant, and he grabbed at my ankles to get the message across.

"I said... Let me help. Or your parents see you like this."

I felt sick, the terror of having to explain this to my family gripping my heart in a vice, so I slowly relaxed and allowed him to push me down onto the bed, legs raised to either side. The steel cage now poked upwards and he gently lifted it to reach beneath. The lubricant was icy-cool as he spread some on my waiting backside and plenty on the plug itself.

Then, he leant forward, lined the tip up, and began applying pressure.

"Grchh..." I moaned, trying to relax, even as all this was happening to me. I could feel that tip trying to find its way inside, and eventually it began to slide in. Slowly.

"Good, good girl, stay still now, that's it... Shhhhh..." He whispered. He clearly had experience at this and it made me so disgusted. I thought about resisting or forcing it out again, but it could end up just causing more pain - and risking his threats coming true.

So I just breathed. I closed my eyes and focused on my breathing, on calming my body down as deeply as I could, the method I'd used before to slip things into me. Not having to hold the toy myself actually made it easier, but I wasn't gonna admit that to him.

After several quiet seconds it seemed to work, progress being made until a moment of near-pain discomfort, the broadest edge of the plug passing inside - finally I gave way, making me gasp.

It was gulped inside, the base touching my taint. It was in me, and I had no idea how the hell I'd get it out again.

"Nngh...!"

"Ah, yes... much better, isn't it?" He remarked, wiping his hands on a small handkerchief. "Stay there for now."

I did as I was told, still breathing sharply at the intruder making itself at home inside of me. I could tell I would go crazy with this thing stimulating from within. God it felt good...

He brought over a white bottle of baby powder, tapping a few times to spread it over my crotch and inner thigh, working it delicately around my new cage. He wasn't seriously going to do this, was he?

"Please..." I whispered, but he just kept going. He confidently slid the bulk of the diaper under my lower back, then brought it up and around to the front. My crushed and caged manhood disappeared underneath, and the plug was given an extra push as he brought the padding tight up against me. Then two tapes were peeled and placed onto the front, and then...