A Sissy's Escape

[[[This story is a sort of continuation of the much shorter story I posted last year 'A New Sissy's Inspection'. If you have already read or intend to go and read that first you can skip this recap and head straight to the main story below.

Recap: A man who had recently started exploring gender with his girlfriend is taken to The Academy to get training to become a better lover for his partner. Upon arrival, he is put in an advanced chastity cage set to constantly keep him on the edge and receives heavy feminisation, given injections and modifications to feminise her figure on the first day before being thrown into intensive classes teaching her proper Sissy technique and etiquette to ensure she knows how to properly serve men. It doesn't take long before she loses herself to her Sissy desires and starts to become genuinely excited at the thought of servicing big juicy cocks]]]

The big red blinking sign taunted me every day. But this time it looked like an opportunity.

Security is 'helping' one of my Sissy peers, the front desk is empty. I'm being led by a big, suited man to my deportment lessons but he hasn't looked back the whole way.

So I ran, of course, I ran. This is the first opportunity I've had to make my own decision in what must have been months. But getting outside was as far ahead as I had planned. It was dark, I was locked in 5-inch heels and a chastity device that was leaving me just on the edge of orgasm at all times, and my heart felt like it could jump out of my chest at any moment.

I stumbled along the dark, cobbled road until my ankles felt like they were going to give way and further until I came out near the motorway. By the time I reached the hard shoulder my bones ached and I squinted into the blinding lights of passing cars as my legs pleaded for rest.

I had barely taken two steps as a huge black car slowed to a stop causing a shiver to crawl down my spine, had I been found already? Too tired to run I just froze like a deer in the headlights waiting to be taken away and brought back to the academy.

The Car

"Oi, get in! You'll freeze out there." Said a low voice emanating from the car window

I gripped the hem of my little pink dress and trotted to the side of the car, was this honestly just a charitable stranger? My legs made the decision; I would have to trust him.

"Thanks" I peeped as I awkwardly pulled myself up onto the seat and landed myself next to a tall, broad man wearing a tartan fleece and hat. Even in my 5-inch heels, this man must have been considerably taller than me, and with his broad figure, he made me feel so small and fae in my slim dress.

After only a couple of awkward seconds, I couldn't help but melt into my seat so deeply that I must have let out a small moan of pleasure as I heard him hum a deep

"Comfy aren't they?"

I peered up at him - briefly catching his eyes scanning down my torso before darting back to the road - "You wouldn't believe how long it's been since I've felt anything like it"

"What was a young lady like you doing out there anyway? You should be more careful" he prompted dutifully, perhaps slightly embarrassed even?

"I didn't have much another choice" I explained comforted by his awkward gesture

"Well, I'm happy to drop you off wherever you need to go s'long as it's this way mind you"

I smiled with genuine affection just gazing up at him. His name embroidered onto the edge of his hat catching the light 'Seth'.

Cute.

His posture stiffened further and his cheeks tinted red "did you have a place? You need to be, I mean."

I shook my head, realising my stare was making him uneasy, which just made me smile even wider. "A hotel I suppose, I just need time to think"

"Well now that's something I can do" He smiled encouragingly as we slowly drifted to silence

The lights of oncoming cars would illuminate us as I studied his frame in silence watching him focus on the road but seeing his hand slip beneath my skirt and massage my thigh. Feeling him reach over and kiss me as he pulls me into his mass. Anticipating every kiss he sends down my neck as his rugged fingers slide delicately down my back making my skin tingle with such sensual anticipation I would have barely thought possible. My breath trembles with every touch as he caresses me so sweetly before pulling back and slowly reaching for his zip. I see his bulge straining to push its way out as I lick my lips in anticipation...

"Hey, hey wake up"

I feel a soft tap on my shoulder, "Seth" I groan as my eyes fight to stay closed and my mind aches to go deeper.

"We're at the hotel. It's a nice one too; I've stayed here on occasion after a long shift. You'll like it"

"Thanks" I mumble softly, pictures of the vivid dream shrouding my mind as I peer down at his lap, my mouth watering in anticipation.

"I'm just glad you're okay, go in now, get yourself some proper rest." he gently coos

I look up at him flushed with an overwhelming embarrassment as images of his form from my dreams flood my mind "I don't have any money" I say almost inaudibly

"That's okay, we can work something out" he smiles kindly, eyes meeting my gaze.

My heart skips several beats as I reach forwards, pulling myself towards his face and pressing my lips to his. He pulls back as I reach my hands down towards his crotch-

"Stop stop stop" his voice breaking as he hastily blocks my hands "I meant I can get you a room, I know the manager"

I freeze in place as my face turns crimson red before hastily scrambling to open the door cursing myself for misreading his words so severely

"It's okay, honestly. It was just a mistake" he states, face flushed but, in a soft and comforting tone

We walk, side by side quietly to the entrance of the hotel leaving the warmth of his car - my first taste of freedom - vacant behind us.

The Lobby

Taking the lead entering the hotel lobby I immediately feel the gaze of the clerk bolt to my chest as his beady eyes greedily peruse my figure. I pull my arms over my chest; suddenly hyper-aware of how much skin this dress leaves on display.

The clerk grins up at me, barely taking his eyes off of my body until he notices the presence of the large man behind me "H-ow how can I help?" he mutters meekly, his whole demeanour shifting.

"The manager here?" comes his reply in a stern tone unlike any used between the two of us in his car

"He is!" says a small energetic man bouncing through the back door with a wide smile on his face appearing to look straight past me up to my companion

The two of them embrace in a kind hug as the beady-eyed clerk shuffles silently into the backroom

"It's been too long!" says the manager settling back into a chair in the lobby

I stand, awkwardly between the two of them, as they reminisce for what my still sore legs consider to be an eternity before the manager pulls his attention to me for the first time "so, you're a freeloader who took advantage of my friend here and is now looking to make a mug out of me too, huh?"

Tears start to well up in my eyes and my cheeks flush a crimson red. Was this really how I came across? "No! I swear I'm no freeloader. I'll pay you back every cent as soon as I sort myself out."

He breathed a laugh as he threw a bottle of water and a room key at me "that's okay, sweetie. If this guy vouches for you you've got a room here."

"Thank you, really." my watery eyes break into streams as they turn to meet Seth's before tightly hugging him "you've done so much for me tonight" I whisper as his arms wrap around me in such a warm and comforting embrace that I can barely stand to leave.

He pulls back, smiles, and heads out the door.

The First Night Alone

It feels so strange.

It's only just dawning on me that this is the most alone I've been in months. I have a room to myself.

I'm free!..

I tried to suck his cock.

I tried to suck the cock of the first man I met after escaping. He didn't even want me to. I've been taking those classes for so long now it was just natural. It didn't cross my mind for a second to correct them for talking about me like a woman. Can I even go back? Can I be a man again?

As I flop onto my huge bed exhausted from the day behind me all I can think about is that dream, salivating at the thought of his big juicy dick pushing against his pants moments from release. The emptiness in my mouth claws at my mind as my chastity device continues to pulse endlessly. Yearning for release. My fingers massage my thighs and soak in my leaking juices before I greedily suck at them with an insatiable craving; I play with my nipples and pull at my plug but can't stop the ache for more.

A whole bed to myself is too much to bear. I need to feel that embrace I've grown so used to. To be entangled with someone whose yearning matches my own.

The room is starting to feel claustrophobic. So I grab my water bottle and head outside. Just to sit and look at the stars.

The car park is so empty there must only be one or two other guests staying here.

Hearing a door creak I peer around to see who's coming, hoping they don't see me out here as I start to realise how vulnerable I must look sitting out here all alone. But my luck had to end at some point today.

My eyes lock with the beady-eyed clerks for a fraction of a second before I swiftly turn my head away looking anywhere but back at him as I hug myself a little tighter hoping he walks past.

A deep sigh escapes his lips as I hear his coat scratching against the bricks of the wall. My muscles tense further at each erratic sound as his figure creeps down inches from my side. His hand brushes against my outer thigh working its way further towards the hem of my dress.

"Some days just get to you," he says in a tired groan, head tilted to the sky. "You know, you were the fifth person I saw all day and the first good thing to happen"

My mind is muddled with so much uncertainty. But this man. He makes me uncomfortable. There's something about the way he holds himself that I can't place. And that initial meeting. The way his eyes locked onto my body as they refused to meet my eyes. Not even at The Academy had I felt this fear.

"You don't talk much do you?" He jabs, "That's okay, We don't need to talk."

I feel frozen in place as his fingers creep beneath my dress all the way up to my chest. His tongue edges down my neck planting kisses as he goes.

"Your skin is so soft"

My skin writhes at his touch.

He reaches his hands around my face and pulls my gaze to meet his as he draws near, eyes closing as his face inches closer to mine.

I inhale.

Deeply. I must have been holding my breath but I hadn't noticed until just now. My whole body jumps into motion as I push him back hard enough to knock him onto his side as I pull myself up, gasping for air, and trot back to my room as fast as my heels will allow.

I push the door shut and place a chair against the handle before I find myself with tears streaming down my face shaking in bed.

Today didn't end well.

Eventually, as the fear fades and I find myself alone again. My mind starts to drift, remembering Seth. Imagining how much different it would have gone if he hadn't left. How safe I felt in his car. In his arms. The warmth and longing I felt; my desire resurfacing as I remember the dream from his car about how close I got to releasing his girth. How much I needed to fill my mouth, taste it, experience it.

His giant cock pushes its way past my lips and over my tongue as the familiar salty flavour causes my mouth to stream with wanton desire. Letting him deep into my throat, my eyes water in protest but I keep pushing further striving to take his whole length. It twitches so slightly as I wrap my tongue elegantly around it savouring every taste as I work his pre-cum expertly from his now throbbing cock. I worship him with my mouth, making use of every bit of practice I've had over the past months.

He's getting so close to release that I can taste it. His cum seeps to the surface as I lust to feel it pulse down my throat and fill my mouth. His semen bursts out and fills my mouth so fully that it sails deep to my core lining my insides with his soft creamy juices. My lips hang so dearly to his head as it reluctantly pulls away from my mouth. Convulsing and moaning so sweetly as his cum warms my core. I peer up, still eager to take more of him into me - lips parted in pleasure and desire - I feel his cum leaking down my chin and onto my pert tits. Pawing at my body and breasts I spread his velvety load over my soft skin. Sucking at my fingers to save as much as I could while softly licking and sucking at his shaft and head in these final moments of bliss. See nothing but his looming cock as I worship him and savour this moment.

My eyes break open slowly as I wake from such a deep dream state still feeling a deep warmth and loving embrace as I hug the spare pillow tight against my chest

I peer out the window and see the sun low on the horizon. I suppose waking at the crack of dawn had become so natural to me that even after such a long night sleeping in was impossibility.

On my way down the hall to the shared bathroom catching myself in the mirror made it clear that the tears shed that night hadn't been kind. 'Waterproof' mascara clouded my eyes like I was taking make-up tips from Marilyn Manson and the rest of my face, having peeled from the bedsheets, wasn't safe from damage either. After tirelessly scrubbing at it for a few minutes I flinched at the sound of the door pressing open, anxiously looking around to see who was about to catch this indignant moment.

A beautiful tall brunette woman in a striking red business suit breezes in straight up to the sink beside me and starts inspecting her perfect face. Correcting an invisible smudge that I honestly think she imagined her eyes dart towards mine in the reflection of the mirror.

"Are you okay, sweetie? You look like you've had a long night" her gentle voice coos

"Other than being stuck looking like a clown I'm starting to feel quite optimistic this morning" I quip back surprising myself with the positive spin on the situation

A comforting smile turns to meet my gaze as she reaches for my cheek with one hand and brings a wipe to my face with the other

"I think I can help with that" she encourages softly wiping away the smeared make-up

A few moments pass as she gently finishes revealing my bare face and smiles down at me "you have beautiful features, I'll just do a quick natural look to enhance them" she says pulling a pencil eyeliner from her bag

Blushing at her compliment and the feel of her nurturing hands gently working on my features I find myself fully relaxing in her control, the tension seeping from my body.

Too soon her hands stay from my face and the bag of make-up zips shut as I look over to see myself beautifully made up. My wide doe eyes trying to understand how she had made such an impact so subtly.

"How did you-"

"Practice" she interjects handing me a card before hurriedly striding out the door

"Thank you!" I gleam stunned by her prompt exit

Looking back in the mirror admiring her work and feeling myself positively glowing the hum of my ever-pulsing chastity comes back to focus as my mind drifts back to the lonely night behind me. I start to think back to the small beds I used to share with other sissies, the long passionate sessions we would share throughout the night as we each longed for a release that could never come, the deep warm feeling of a job well done after a successful 'inspection'. My mouth-watering so much as I reminisce on the taste of a real man's cum filling my mouth, gliding deep down inside of me as I eagerly await my next order.

My hands drift to my breasts, pushing aside the fabric of my dress, and groping at my pert nipples as I slowly groan in pleasure and desire. My mind filled more and more with images of experience and longing. A sharp creak at the door pulls my mind back to reality.

A small elfish looking girl bursts in the door and stops abruptly as she sees my flush red face and almost bare breasts as I clamber to regain any degree of decency at the sudden intrusion.

"Sorry!" she exclaims darting past and into one of the stalls

I hurry from the toilets and rush for the exit wincing from embarrassment

The Locksmith

The hotel was only a short walk from town and the pace I had set from my swift exit made short work of that, landing me right in the centre of town. It felt weird being here like this. Such a familiar place but from such a new perspective. I felt so vulnerable. So small.

Before anything I had to visit the locksmith, I know I had no money but if I wanted to function without drifting into an erotic daydream every 5 minutes I needed to get out of this chastity device by any means necessary.

'Ting' the old fashioned bell cheerily announces my entrance as I push forwards into the dim old shop

The counter directly opposite the entrance is empty and the rest of the shop follows suit.

"Hello?" I murmur to the empty room as I start to slowly float around the shop looking at things mostly foreign to me waiting for someone to present themselves

"Just a minute!" prompts an echoed voice from a well-lit backroom

Eager to finally be rid of this infernal thing I quickly push forth towards the room to plead with the owner to help me.

"Sorry I just-" I stop freezing in place as I watch this handsome, trim, man fumbling with his zipper rushing to cover his crotch with his hands

"No! No, sorry. I'm so sorry, we don't usually have people in the shop this early so I was just, uhm, back here?" He blurts out, posture bending to try and hide the bulging member trying to push out from the hasty concealment. Even despite his best efforts to hide it his impressive length pushes down his leg tightly pressing against the fabric at his thigh.

Still frozen in place, my eyes locked on his crotch, my mouth starting to salivate as I'm taken back to that place, to The Academy. The greeting I was programmed to say to any adult rushed out of my mouth before I could stop it.

"How may I make your day better?" I ask, body and mind betraying me, as I neatly transition to a curtsey raising the hem of my skirt neatly as I had been taught countless times.

"That's.. Not how people usually greet me" He says curiously "How can I help you?"

"Ah- I" I start, face flush, arms crossing as I realise what I had just done

"I was just, I mean, I know this isn't the best way to start but I don't have any money. And... I need you to help me get this lock open."

"Well, if we helped everyone who asked that we'd be out of business!" he quips back

"Maybe we can arrange... Another means of payment?" I push, still salivating, eyes locked on his crotch, as I start to bite my lip

His posture straightens as his body closes the gap between us and his face stops inches from mine as I feel his breath brushing along my cheek and between my lips "I think we could find something you're good for"

My mind drifts further as I let out a gentle moan of anticipation

His arm reaches the small of my back as he pulls me into him, lips locking, as his tongue deftly presses its way into my mouth in a deep heated kiss. His big arms engulf me as I submit completely to his control - eventually encouraging me down towards that impatient bulge that had been avidly pushing into my thigh as we absorbed each other.

My mind blanks as I experience this suspense completely. Watching him strain against his trouser leg waiting to be released I press my face against his concealed cock kissing and licking at the length over the fabric barrier as my hands reach to help undress his lower half.

As I slowly pull his trousers down his cock bounces back up eagerly hitting my face as it finds its place pressed up against my cheek. I slowly pull my face back to align my soft lips with his head as I start to kiss and lick at the tip watching it bounce and throb at my gentle teasing touches.