A Sissy's Escape

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
KeiraSL
KeiraSL
72 Followers

Melody's delicate fingers wipe at my eyes and press the gathered cum gently into my mouth letting me suck them passionately clean. My eyes open to face a kindly smiling Melody who flicks her eyes to the side and giggles, "finish up".

My head turns back to face the dripping cock as I quickly dip to catch the falling strands of cum hanging from his slowly softening member. My tongue expertly licked and sucked at his length cleaning all of the juices enthusiastically from his cock. "Good job, sweetie. Let's head home" Melody says taking my hand to help me stand, a thick string connecting me to the puddle of juices I leaked on the floor. "Good job we're keeping you hydrated, hey?" she giggles leading me out the door, "Let's go."

"Yes, mistress" I drop into a maid curtsey before following her out the door

Leaving the restaurant and heading back down the street I feel the cum constantly dripping down my shoulders and body, as well as my constantly leaking juices dripping down the floral patterns of my black hosiery. A man in passing smacked my ass hard causing me to let out a little squeak as I followed Melody's unwavering pace with my cute little trot feeling my bouncing ass sting with every step

Coming into the house and heading straight for Melody's room she sits on the bed guiding me to stand tall in front of her as she reaches for my face. "Take your heels off, I can't reach you properly like this" she prompts, my feet immediately slipping from the tall stilettos

"Yes, mistress" dropping into a maid curtsey once more.

"Good girl" she encourages, her finger slowly wiping the dripping cum from my face and pressing it into my mouth bit by bit as she smiles kindly at me.

"I've had a lovely day with you" she reassures, "but I think we might have proven beyond a shadow of a doubt that being a pretty Sissy girl comes very naturally to you" she continues, her fingers still feeding me bit after bit of the thick stranded cum covering my face and body "as much as I love the idea of having my very own slutty Sissy plaything" her finger slowly pulling from the tight suction of my lips as my tongue greedily licks the cum clean "I have to ask, don't you think you should head back to your other owners?" she questions kindly, her finger wiping gently up my cheek "you made it sound like they might be worried about you, I'd hate to think how I would feel if you ran away from me like that" she insists, her brows bowing to show concern, her finger pressing lightly back into my expectant mouth, my tongue wrapping ravenously around it.

Her finger pops from my mouth and wipes across my brow. "You're right, I've been immature" I sigh looking forlornly down at her, savouring another thick strand of cum before continuing, "I really will miss you when I go, though. I've loved spending time with you."

"Sweetie! We'll stay in touch, I'm not just going to let a cute little thing like you vanish" she pipes, wiping the sticky pool from my collar bone and offering it slowly to me. "You can visit!" she insists, "and I'll visit you!"

I nod my head happily and beam a smile down at her, "thank you".

We stay silent for a few minutes as she finishes feeding me the covering of cum from my body with her dainty fingers letting me savour every drop as I slowly lick and suck at her digits greedily.

"Come now" she insists cheerily, "I'll drive you home!"

"But I look-" I start

"Like you've kept up with your training," she continues, "you said they were helping you come to terms with your feminine desires, right? I'm sure they'll understand. Get your heels on we'll head out now." she urges. My body naturally followed her orders. "Yes, mistress" I recite, dipping into a maid curtsey before slipping my heels back on.

The Academy

We pull up to The Academy parking lot, just as I had with my girlfriend when I first enrolled we sat in silence for minutes before one of us started.

"Whoa, it's big" Melody announces looking over at me.

"Yeah, they have a lot of classrooms" I respond "and just as many rooms for... private tutoring" I continue.

"Well, that's amazing! You must learn so much here." she enthuses beaming a happy smile at me.

"I suppose I have." I realise trapped by her gaze

"Come now!" she grins starting to push her door open "let's get you home"

"Yes, mistress" I recite, making my way out of the car.

As we start for the front of The Academy she jokes "think I'll get a reward for bringing home their lost puppy?"

"You deserve one." I insist, thankful to her for her constant support.

She gives a little chuckle as we walk through the automatic doors of the front entrance

"Congratulations, Sissy! You passed." Comes a deep voice from ahead followed by a few clapping hands, Melody also shining an excited smile at me as she claps along.

"I- I don't understand?" I say, eyes darting around the room spotting almost everyone I must have interacted with over the last couple of days.

"You were all in on it? Did you let me escape?" I question unsure what to think.

"We gave you an opportunity," says the deep-voiced man ahead of me. "All sissies here get them every two to three months. It just took you until month nine to take one."

"So none of this was real?" My eyes slowly start to tear up.

Melody looks over to me and wipes the tears from my eyes before planting a kiss on my cheek, "your choices were" she reassures brushing her thumb across my soft cheek.

"But you weren't?" I grimace scared of her response

"We were paid to watch you, but that's it. Everything we did together was real. I hadn't even met a Sissy before you. I researched it for the job" She comforts. "I had so much fun with you, please don't think it was fake" she sobs, her smile drained from her face.

I pull her into a deep hug and kiss her forehead. "Thank you" I whisper. Happy to know at least that was true.

"Eww! You're so sticky!" she giggles planting a kiss on my lips "I really can't believe how much you love cum though, you're a wild one, girl" she smirks stepping back as one of the security guards comes to reattach my chastity device.

"So, what exactly did I pass?" I ask looking forwards again to the deep-voiced man congratulating me.

"Your first exam, of course!" he states flatly "you proved to us how well your training is coming along."

"But I tried to escape, aren't you mad?" I ask unsure

"Everyone does eventually, it helps to realise why you're here," He says in his monotonous voice. "You did very well, by the way."

"I did?"

"Yes, at the first opportunity you tried to seduce Seth here, who was quite literally the first man you met outside of The Academy" he gestures over to Seth who smiles back at you. "Your denial of the creepy assistant at the hotel proved that you are making the decisions and not just submissively doing anything that someone asks of you" He looks quizically for a second. "that wasn't a part of the test though. We paid the hotel manager, not the assistant. We're starting her at The Academy today as mandatory disciplinary training. After watching her try to assault you it was agreed that she needed an updated outlook on sex. She'll start back at the hotel as Candy hopefully next year on the bimbo slut fast track course." He clears his throat "anyway the next day you went straight to get your chastity off, presumably you thought it was solely responsible for all of your cravings for cock?"

"Yes sir" I mumble.

"Well, the way you expertly led the locksmith to let you suck his cock within minutes of walking into the shop was expertly done. You didn't seem to consider even for a second that you might convince him otherwise to unlock you. Simply explaining your situation or offering to repay him later did you? Be honest with me."

"No, sir. I was too distracted by his cock to think of any other option. I would have begged to taste him even if he had refused to accept it as payment for his services." I agree face bright red as I stand at the centre of attention in the wide lobby forced to recount the last three days."

"Brilliant work." he encourages a tinge of emotion showing through his voice. "And after that you went shopping, right? To buy back your masculinity or some such absurdity I presume?"

"Yes sir. That about sums it up. Only having thrown my plug and chastity in the bin I was aching so badly that I could hardly think straight. I went to buy some men's clothes but by the time I was heading for a haircut, I couldn't help but visit the sex shop instead. I couldn't tell you if this was more because I was petrified by the idea of cutting my beautiful long hair or because the aching in my ass became an overwhelming need to be stuffed with a big plump plug but I spent the last of my money there on such a plug and some tight panties" I state honestly trying to recount my steps as I accept my situation.

"Both it would seem are fitting answers for a slut like you," He nods. "And then you went to the club, fitted with a buttplug, cumslut panties, long cared for hair, and perky breasts expecting to be seen as a man?"

"Yes sir." I accept "Having no money I just stood on the dancefloor trying to work out how to approach a girl"

"Until Melody showed up and you thought you hit the jackpot, right?"

"Exactly," I say, prompting him to let out a sharp cough. "Yes sir." I correct "as we headed out of the club absorbing each other passionately back to her house I thought I was doing everything right, maybe I was meant to be a man after all"

Melody lets out a little chuckle making me blush hard and look down to the floor before correcting my posture and continuing. "But when she pulled her panties down I realised my cock couldn't get hard, this was possibly the only time I briefly considered my clitty to be a cock. I looked down at her clean front and tried to kiss her but was unable to help tearing up as I started to accept that my body just wasn't compatible with girls anymore, wishing she had a juicy cock for me to bounce on. Trying to want her as I would have before but being unable." I look to Melody "Instead we just lay together for a while as she comforted me, she was sweet and kind and helped me to come to terms with who I had become. Assuring me that it was okay to embrace my femininity."

She smiles back at me "and then I had a wank" she says with a giggle.

"And I soaked my skin in a milky pink lavender bath and relaxed in the swirling feminine water" I continue.

"And the next day she allowed you to get some, obviously necessary, male attention?"

"Yes sir." I nod "within 5 minutes of leaving her room I had already found myself pressed against the cock of Genie"

"Of whom?" his eyebrow raised

"Eugine" Melody interjects, "my roommate"

"Ah, yes." He accepts "continue"

"His cock was unreal; it pushed so deep into my throat. He grabbed and pulled me about so dominantly. I felt so obedient." My mouth salivating from the memory "and then he turned me around and plunged so deep inside of me that I thought he was going to break me. I felt my clitty leaking so much while my body glowed with pleasure." I reminisce.

"Yes, yes. We don't need all of the details" He insists "though if he is that good perhaps we could have his contact information, Ms Ayre?"

"Of course!" Chirps Melody

"Continuing that you traversed the town a cum-covered Sissy slut and seduced a fellated the waiter for the price of a small salad?" He questions

"Yes sir." I start "but-"

"Technically the salad was free anyway" Melody interjects, "I had a coupon. I just wanted to see if she would do it"

"Excellent" he states

"I hadn't had the chance to report the rest yet actually" Melody starts "the waiter released an impressive load all over her face to such a degree that she was positively dripping with cum the whole walk back. It was so cute how her little clitty leaked so much down her pretty hosiery as she felt the cum dripping down her body."

"Exceptional work Ms Ayre." He congratulates.

Melody continues "As we got her back to my place, I stood her by the bed and slowly fed her the mix of cum, that had been dripping from her face and down her body throughout the day, with my fingers while we spoke about her feminine urges and she agreed that it was time to come home" she smiles proudly towards me.

"I say. Perhaps you should apply to be a trainer yourself, Ms Ayre." He pronounces. "We always need more people who know what it is a good Sissy needs."

"If all your sissies are as good as her I would be delighted to work with you" She beams.

"Good stuff, well I think that's all for today, if anyone has any questions feel free to contact me and otherwise I think we can adjourn this meeting. Again, Thank you all for helping." he shuffles his papers and starts to walk off

"Wait!" I protest. "We just went over the last few days but I still have no idea what happens next?"

"Well, you have three months to the end of your first year with us, usually that's when a Sissy graduates on to a new profession. Over the next week, you will be studying Sissy progression options. Hopefully, by then you will have decided what it is you would like to do in the future with your new Sissy life. Then you will end the year training towards your new Sissy life goal" he recites plainly "of course there will be an extra intensive month course preparing you for your one or two-year repayment scheme, where you act as a live-in Sissy maid and cum slave for your ex-partner's new boyfriend. This extra month comes complimentary with the year-long course. Whether you service him for one or two years depends entirely on the decision of your ex-partner as your academy appointed sponsor. For our trouble at The Academy, we also hold a right to use you as we see fit one day per week for the foreseeable future following your course."

"My girlfriend has a new boyfriend?" I gasp.

"Your ex-partner has indeed become engaged in another relationship, as her last relationship ended with her boyfriend at the time transforming himself into a feminine Sissy slut who lusts for nothing but to worship cocks and shower in their cum it became apparent to her that she needed a real alpha male to assure this doesn't happen again." he responds in his monotone voice "here's a picture of him for reference"

He holds out a Polaroid of a thick semi-erect cock that hangs almost down to his knee. "Your ex-partner did offer a picture of his face but I didn't see any reason for your interest in such matters and as such opted to keep it out of the file"

My mouth gapes wide as I realise I'm promised as a slave to that cock for at the very least a full year. Will it even fit inside of me? How much cum can a cock that big produce? My mouth starts to salivate so much at the images of this snake of a cock splitting me open that I feel it dribbling down my chin powerless to stop it as I'm hypnotised by this image.

"Good, I think that's enough for today. Take her back to her room if you'd please?" he says matter-of-factly before walking off.

Melody kisses me on the cheek, "I'm so glad you got to be my slut-for-the-day, thanks for everything" she says in her usual shining tone before bouncing off out the door.

As I watch the room jump back to life as everyone starts to file back out of The Academy security comes and takes me back to one of the small rooms with a single bed that I share every night with one of the other sissies.

I take my place on the hard small bed, my chastity buzzing with its never-ending pleasure keeping me on the edge, entangled with another Sissy embracing me with her endless, unachievable, need to orgasm as she hangs from my lips as if I'm the last only thing in the world, I think of the beautiful journey ahead of this rookie Sissy ravishing my body and sigh a happy breath.

I'm back.

KeiraSL
KeiraSL
72 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
tvlove007tvlove007about 1 year ago

Great story. I would love to walk in her shoes. Maybe the other optional course could include post op transition.

Butthobandit61Butthobandit61over 1 year ago

A very good and ingenious twist. Wish there was more upon the main character's return to the Academy.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
Sissy, Hypnotized A night out results in triggers unleashed for this sissy.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
More Stories