A Sissy's Escape

I start to explore his impressive length licking and kissing down to the base as I plant a kiss on his balls before my patience reaches its end and I eagerly pull back to press my lips back to his head pushing him slowly into my longing mouth. Finally, fully experience the taste of his heavy cock as my tongue wraps around him savouring the sweet-salty flavour as I continue to push him deeper and deeper into my throat. Pulling and pushing back and forth as I inch him closer to my throat taking in as much as I can before finally pushing further and forcing my lips to his base as he pierces down my throat. I hold my place for as long as I can before pulling back with a gasp for air admiring the mix of precum and saliva that still connects my mouth to his glistening, throbbing cock goading me back. I slow to lick around his head again gathering the mess of precum drooling from the end and plant another kiss at the tip before starting to greedily suck and gulp at his throbbing length again repeatedly taking him deep to the base. Feeling the pulses slowly increasing in pace as feel him nearing his edge. The taste of precum fills my lustful mouth now as I can think of nothing but the taste of his sweet release.

I pull back, reluctantly releasing his cock from my greedy mouth, waiting for him to cool down just enough to keep this going. I want nothing more than to take him back in my mouth and feel his cum push its way down to my core but instead, I kiss around the base waiting for the throbbing to lighten before sucking at his balls and eventually starting to make my way back from the base along the shaft in long sloppy licks and kisses. Taking the head back into my eager mouth taking him deep inside of me as I continue to wrap my tongue around him pushing him closer and closer to the edge excitedly speeding my pace as I feel him jump over that edge and explode in my mouth. I push his throbbing releasing cock as deeply as I can into my throat as I feel the warm, comforting, embrace of his cum filling me to the brim. I slowly start to pull him from my mouth as the last drops of his orgasm seep from his tip.

Warm and full from his glowing load inside of me I passionately kiss at his slowly softening cock as I softly lick around his edges cleaning the last of his load from him and savouring its flavour before swallowing it down.

Slowly coming back to reality I hear his and my groans of pleasure and heavy breaths slowing as we recover from the heated session my eyes still glued to his cock as I lean lightly against his leg.

"Wow, I wish every workday started like this" he jests between breaths

"Maybe it should" I mutter eyes still transfixed on his now hanging cock before shaking my head a little and starting to gather my composure.

He helps me slowly back to my feet and pulls me in for one last embrace as my head rests against his chest.

"I'm sorry, no one should have to pay for something like that. I didn't want to force you or anything. I just got a bit over-enthusiastic." he says gently brushing his hands through my hair

I shake my head in rebuttal "This was necessary, thank you for being kind." I insist with my head pressed heavily into his chest

"So, you had a job for me?" he prompts awkwardly as we slowly part from our embrace.

"Yeah, It's kind of urgent," I explain, slowly lifting the hem of my skirt to reveal the advanced chastity device belted to me.

"I see." He suggests dutifully. "This might be tricky but I'll see what I can do."

I sit up on the table with him below me on his chair working at the lock on the band just above my crotch, still dripping wet from our passionate exchange.

As he started working on the lock there were some brief minutes of silence as we sat together. Eventually, he broke that silence by asking "So, how does a beautiful girl like you end up in such a predicament?"

My cheeks flush red as I ponder how to answer his question delicately. But eventually, I found myself telling him all about The Academy, my classes, and how much I found myself starting to enjoy it. I even confessed I used to be quite a normal man - as he was going to find out soon anyway. Most of all I found myself talking about the day before though. Confessing how after escaping and having the chance to start becoming my old self again I had been having constant dreams of men and cock, how I constantly longed to feel that warmth filling my insides. How I kept my buttplug in the whole time because I felt empty without it.

This kind man sat and listened to all of my problems responding briefly but with understanding as he diligently worked to free me.

As my rambling account of events was becoming less coherent he started speaking softly "it sounds to me like your girlfriend was just looking out for you."

"But-" I interject

"Sometimes it's hard for people to see themselves as they truly are. We all have these notions of who we should be and we strive so hard to reach them that we forget to look inside ourselves" He continues

"So you think-" I try

"That your girlfriend might have seen the real you and been trying to help you grow into the beautiful flower you had the potential to be, always were, and have become" He insists briefly looking up to gesticulate his hand towards me as if to emphasise who I have become."

After about an hour of tinkering with the lock finally, we heard a 'click' as the mechanism released and the device loosened its grip on me. I let out a surprised squeak as it came loose

"You don't have to take my advice but maybe think about what you want and who you are instead of what's expected of you. At the end of the day, that's all that matters." He states calmly as he clips the small locks from my heels as well, I pull the device from myself for the first time in months. Finally feeling the pressure and the constant pulsing stop I sigh with relief.

starting to pull my lace panties back up I briefly feel my small loose clitty beneath them as I try to push it back to hide the small bulge from sight. I can't help but compare the small size of my 'penis' to the throbbing member I just had down my throat. Memories of my ex-girlfriend taking it to the base as it barely reaches the back of her mouth hit me like daggers as I compare the memories of cocks sliding deep into my throat with ease.

I shake off my thoughts and pull my dress back down as I turn to face the shop-keeper

"Thank you!" I exclaim kissing him firmly on the cheek "Thank you."

He walks over to the counter and gives me a few notes from the register

"It's not much but a girl like you shouldn't be walking about with no money at all." He states.

I meekly take the money from him "you've done so much for me. Please let me pay you back when I can"

"Just take care of yourself." he insists planting a delicate kiss on my forehead

"I will, thank you." I meekly reply before heading for the exit

I throw out the chastity device, and my plug, in the bin outside. Deciding to try and reclaim my old lifestyle even as his kind words of reassurance echoed in my mind "think about what you want"

Reluctantly I leave them behind and head for the shops.

Shopping Trip

Before long I find myself in the old clothes shop I used to get most of my clothes. The girl at the counter used to be almost someone I would consider a friend and she would always fill me in on the latest fashion trends. When I first saw her I positively bounced towards her and greeted her with a familiar "It's so good to see you!"

Her eyes darted up at me as she reluctantly smiled and prompts "Hey! Welcome to T&F clothing how can I help?" showing no recognition of me at all through her thin veil of pleasantry. She always hated dealing with "girly girls" as she put it and I was starting to think that's what I might look like.

"Oh, I was just looking for some new clothes," I say, suddenly completely unsure of how to interact with her.

"That IS what people normally come here for, yes," she states monotonously, rolling her eyes. "We don't do girly clothing here though, we're more of a menswear shop. Sorry sweety" she continues bitterly

"Yeah, I know. I was kind of looking for something a bit more... manly?" I murmur suddenly feeling insecure about my request. Do I look that out of place here?

"You just don't look- Ah whatever, let's get you some boyfriend jeans, girl!" She announces, getting up from her seat as her demeanour shifts to a slightly more friendly tone and she drags me along the store.

So, we know you want to look like a macho girl! So what are your measurements? We've got to do this right." She insists

"Medium?" I mumble, she never asked me that as a man.

"Medium?" She repeats emphatically. "That's probably not going to cut it, come to the changing room, let's get you measured up" she insists pulling me into the curtained room.

She helps me out of my dress and pulls her measuring tape out of a pocket and gently wraps it around my hips. As she looks down to get the measurement her cheeks redden ever so slightly and a smirk crosses her face. Did she just see my bulge? Does she know I'm a man? She quickly takes my waist and bust measurements as well and writes them down.

"Wait right here girly!" She decides, floating out of the room.

I stand completely still in my lingerie unsure of what I'm waiting for. Slowly I start to imagine her pushing through the curtain with a strap-on as she pushes me down and makes me suck on it

"I know your secret 'girly'. Get my cock nice and wet for me. You know where it's going." she demands as I catch myself in the mirror diligently sucking on her huge bright yellow ribbed strap-on leaving trails of saliva as I follow her instructions.

Feeling the strap-on deeply penetrate my throat as I start to choke on the unfamiliar texture she pushes me back, turns me around and presses my face against the mirror as my back arches my expectant hole towards her giant dripping monster-cock.

My mind snaps back to reality as I see the curtain twitch slightly open and she peeks her head and arm through passing me a small pile of clothes. I can't help but notice her eyes flick down and back up again before her head pops back out of view and she prompts "try some of these on" through the curtain.

I look down and see my little clitty dripping, and pushing, against the lace pattern of my panties making my bulge slightly more obvious. She knows. My cheeks turn a cherry-red colour as I rush to put some of the clothes on.

The outfit I chose was some high waisted, straight cut jeans, a plain white T-shirt, some cheap black trainers, and a simple grey jacket.

After thanking her for her help and continuing to browse I also got myself some men's underwear and took my lingerie off as well before heading to the counter to pay.

"You could put these old clothes in the charity box for me. I'd love for them to have a nice home!" I say cheerily dressed in my new men's clothing after paying.

"Sure thing, girly" she states happily chucking them in the box behind her.

As I start to leave she quickly prompts "I think you make a better girl by the way"

Pretending not to have heard her I squirrel out of the door and start down the street.

Starting to head for the barbers to get myself a more masculine haircut, my mind starts drifting to my crotch, a loose lonely feeling leaves it aching. Missing that constant attention. The free-hanging sway inside my boxers leaves me feeling uneasy and vulnerable. My butt tensing trying to pull at the plug that's no longer there leaves me feeling empty with every step feeling the absence of the plug pushing at my buttcheeks and moving around inside of me.

Continuing the painful walk to the barber takes me past an adult shop that echoes the locksmith's words in my head. I can't take this discomfort. I need you to do this for me.

Heading inside the adult shop I anxiously start looking around for a replacement buttplug, eventually finding something fairly similar in size to the one I had before and picking up a pair of panties to help my clitty feel snugger. I almost didn't buy the panties because they had "cumslut" written on the backside and an arrow pointing to the crotch with "freeuse" on the front but after mindfully walking to the counter without them I ran back to pick them up unable to bear the discomfort of the swinging feeling in my loose boxers.

Leaving the store as quickly as I could I dipped into a quiet corner and pulled my boxers down before pushing the plug snuggly back where it belongs and pulling the embarrassing panties up instead.

Not having enough money left over for the haircut I meant to get I picked up a hairband and messily tied it in a bunch hoping my long hair would appear less feminine when it's not flowing down my shoulders like a Disney princess.

The Club

As it starts to get later I head off down the club determined to prove my masculinity and meet a girl. After queuing for about half an hour to get into the club and spending the remainder of my money on the entrance fee I trotted off to the packed dance floor. Too scared to dance sober I find myself awkwardly bobbing up and down to the music as I look around at people looking for someone to awkwardly bob with. Quickly after landing on the dance floor my breasts start to feel sore from all the movement and I can't help but try to discreetly pull at my T-shirt and rub at them to try and relieve some of the pain but find little success in doing anything but getting some odd looks from the men around me.

After an excruciating amount of time I start to feel hopeless and consider making a turn for the exit but just before I do a small girl with shoulder-length curly brunette hair, sparkly earrings, and a little dark blue party dress taps me on the shoulder.

I let out a little squeak of surprise at her touch and turn to face her before trying to say "Oh, hey" in a manly voice that comes out a broken mess. That's going to take some work.

"Hey, I'm Melody, you looked like you could do with a drink so I got us some shots!" She chirps with a wide grin

"You were so right. Thanks!" I cheer, reverting to my, comfortable, trained feminine voice.

We each take two of the shots she's holding out and she pulls me further onto the dance floor and starts dancing around me pulling me in all different directions as I slowly loosen up and start naturally pulling out some of the dance knowledge they taught me at The Academy as we both get slowly more lewd in our dancing, our hips bouncing as we writhe against each other. As the music slows she looks up at me and gently plants her lips against mine in a delicate and fruit-flavoured kiss. I let her pull her lips from mine as she pulls my hairband out letting my hair flow back down my shoulders. Her lips dip to the side as she kisses my cheek and whispers in my ear "I like it better down"

As we separate I bump into a man behind me and his drink spills over me soaking my entire torso. Melody quickly grabs my wrist and pulls me towards her as she leads me neatly out of the club and presses herself up against me

"You're not wearing a bra," she states matter of factly

My cheeks redden as I look down at her face inches from mine "I suppose not."

"We need to get you dried off" she purrs softly pulling at my T-shirt to separate the fabric from my skin before using it as an excuse to feel my pert breasts beneath the small bit of transparent wet fabric.

As she pulls back she grabs me and kisses me with a lust devoid of the innocence of our last and I savour her taste as she pulls me off down the street. "My house is just down the road. I'll help you get cleaned up"

Her House

As we enter the house she pulls me close and kisses me deeply before pulling my shirt over my head revealing my bare breasts, nipples erect from the wet. Her mouth reached for my breast. As she licks and sucks at it simultaneously pinching the other. Flicking and biting, getting rougher as she hears my pleasured gasps and moans from her experienced touch. She starts to lead me through the hall into a small mostly pink room. Her bed took up most of the room with far too many pillows and a vanity at the end. She pushes me back onto the big soft bed and jumps on top of me pulling me into a passionate kiss as she fumbles with the buttons of my jeans. She pulls back as she frees the last button and pulls my jeans down revealing my black panties with 'freeuse" planted on the front. Realising the position I'm in I get ready to start explaining myself but she just giggles and pulls them back too.

As my panties come off her eyes widen and dart back to mine as she sits back slightly. "Oh, Uhm. I'm sorry! I thought you were a girl?" she says quizzically

"It's... complicated. I'm sorry" I say suddenly unsure of myself.

"Sweetie! It's fine, honestly. Let's try it! Here, you take the lead." she says reassuringly as she deftly rolls us around leaving me on top. As I look down at her, curls framing her delicate features and dress pulled down revealing a cute lace bralette covering her small chest I remember my time sharing beds with other sissies and how we would violently ravage each other in hopes of a release.

I gently help her out of her bralette and lean down into a soft kiss as I start to gently massage her breasts and kiss down her neck I slowly start to bring my focus to her nipples delicately pinching at them as I kiss across her collar and down to her chest.

Her hands lightly drop from my back as she pulls the hem of her dress up and lifts herself slightly as her matching panties slide down her smooth legs revealing her dripping pussy

"I'm ready" She groans as I look down before continuing to gently caress her body.

I pull back and bring my face to hers locking our lips once more before pulling back and letting a tear drop from my eye to her cheek. "I'm sorry" I whimper "I can't do it."

She hugs my head down next to hers letting my tears soak the pillow beneath her as she holds me in an embrace. "It's okay. You don't have to do anything you don't want to," she says reassuringly in her sweet delicate voice

A few minutes pass before I pull myself back off of her and start "I tried so hard to be a man today. It felt like everything was against me but I pushed through and I did everything I could to make it happen. I changed my clothes-"

"I did think you were dressed a little plain for the club" she interjects

"I even danced with a girl at the club"

"I did think you were a girl mind you" she prompts again

"And I got that blasted chastity cage off"

"Ooh kinky" she giggles

"Even after taking you home, I couldn't follow through. It's like nothing feels right anymore"

"Sorry, I'm not trying to make fun of you. Have you considered that maybe you're taking this whole thing too seriously? You said everything was against you, right?"

"Yes. It's like every time I take a step to be more manly something got in my way. There was a barrier that pushed me back to femininity"

Did you ever stop to think that maybe you were creating those barriers yourself because femininity is right for you? If nothing feels right when you're trying to be masculine that's probably because you're supposed to be feminine, right?

"But before this year I never would have considered the possibility that I could wear panties let alone publicly display as a woman, how can everything in my life just suddenly change like that?"

"Maybe it just took you this long to find out who you were. Sometimes it isn't until you find out what's right that you realise what was wrong before. Exploring your femininity could have helped you discover how wrong masculinity feels for you?"

"But I just threw away all of my female clothes, and ran from everyone who was helping me explore that femininity! What if I can't just go back? What if they don't forgive me?"