Page 22

Chapter 5

"Isn't she just a darling little sissy!" the woman cooed. "Very lovely work as always, Saskia."

My chin was pinched between her fingers, my head tilted up and backwards so she could inspect me. Her eyes ran down my neck to my chest and across my black skirt. She released me with a shove and circled me, her hand brushing against the satin of my dress. One hand disappeared under my skirt and encircled my cage through my panties.

I managed to stifle a yelp, turning it into a mere gasp of surprise, shooting a wide-eyed look at Mistress. She had a nonchalant smile on her face as the other girl took her coat.

Probably a sissy like me, I thought, admiring her tiny yellow dress. The sissy had curtseyed politely to Mistress when we had arrived, but given me a look like she smelled something foul.

"Hush, girl," the woman holding my cage snapped, looking up and past me while her fingers worked their way over my panties.

I felt her feeling my cage, probing its contours. She gave it a satisfied wiggle, then withdrew her hand. She nodded and smiled, gesturing towards the sitting room.

"New style of cage, Saskia?" she asked as we followed.

"Yes, Colleen," Mistress answered, settling into a wingback armchair at one side of the room. "The shaft angle is a little steeper now. Pushes everything back. This creates a perfectly smooth front. You'd never even guess she's wearing one."

"It's true!" Colleen laughed, the sound of it filling the room. "That's why I had to feel it for myself. What a lovely first cage. You're a very lucky sissy, Michaela."

"Thank you, Miss Crawford," I said lightly, nodding my head. "Mistress Saskia is very generous."

Colleen chuckled and turned back to face my Mistress. Through an archway next to her, the sissy in yellow appeared carrying a tray stacked with pastries and a coffee service. She busied herself preparing their drinks, studiously avoiding looking at me while she worked. I noticed that when she bent, she pivoted at her waist like I did, her miniature dress flaring up and framing her rear with cream-colored lace.

"Not that I'm disappointed to see you, Saskia, but why do I have the pleasure of entertaining you on this lovely summer afternoon?" Colleen asked, accepting a mug and saucer from the sissy.

"It's time for Michaela to meet the women of Coopersville," Mistress explained.

"Taking her out for a little tour d'debutante? "

"She needs to see how things work around here. What's… expected of her."

"And you thought of me first, Saskia?" Colleen said, her voice playful. "Why, I'm flattered! "

"Of course, Colleen, who else? And of course, I wanted to see how little Georgiana was doing."

"Ahh, I knew you had ulterior motives," Colleen grinned, pointing a long finger at Mistress. "Shall I call her? Are you ready to start?"

"When am I not, Colleen?"

"You naughty, filthy girl," Colleen laughed, grin widening. "No wonder your girls always turn out so well. Georgiana! "

The sissy in yellow — Georgiana, I gathered — appeared in the archway again, back straight and knees together, hands folded neatly across her lap. Her sleeveless dress was empire-waisted and made from several layers of shimmering, sheer fabric trimmed in white lace. The neckline was a high collar. There were two oversized floppy ribbons atop each shoulder. She wore matching sheer panties, the barest sliver of which were visible beneath the swaying layers of her dress. She looked at Colleen expectantly.

"Yes, Madame?" she asked, voice high-pitched and breathy.

"Georgiana, it must be so lovely to see Saskia again," Colleen began.

"It is, ma'am!" she squealed. "It has been much too long, Mistress Saskia. Such a pleasure to see you again."

She curtseyed, pulling the topmost layer of her dress outwards and bowing her head. Mistress returned the gesture with an almost sarcastic lift of her coffee and a small nod. Georgiana straightened and stepped backwards before Colleen gestured for her to remain close.

"How long has it been since you gave her to me?" Colleen asked Saskia.

"Goodness, at least a year," Mistress said, glancing at Georgiana. Then she added, eyes twinkling: "I am very pleased to see you enjoying the fruits of my hard work."

Colleen laughed again. "Nobody trains a sissy as well as you do, Saskia. And nobody enjoys them as much as me."

"I bet Angelica could give you a run for your money."

"The difference between her and me," Colleen said with a smile, enunciating every word. "Is that I have taste when it comes to the sissies I let into my home."

Mistress chuckled, the sound almost surprising me with how rarely I heard it.

"Would you like to see what she's capable of now?" Colleen asked.

"I'm afraid that will have to wait until next time," Mistress said apologetically.

"Ahh, you're here for Playtime," Colleen said, a grin spreading across her wide face. "Georgiana, the toys?"

The sissy curtseyed and disappeared from the room, returning a moment later carrying a silver tray covered in all shape and size of dildoes. Some trembled at the slightest touch while other towering shafts remained steadfastly rigid. Georgiana bent to lower the tray in front of Mistress, who quickly selected a long, broad dildo shaped exactly like an erect cock. Georgia plucked it from the tray and handed it to Mistress, then disappeared from the room again.

"Michaela," Mistress said, gesturing for me to come over. "This is an important day for you. How long have you worn that cage?"

"Almost four weeks, Mistress," I answered.

"And have you been allowed to take it off?"

"No, Mistress."

"When will you get to?"

"When Mistress allows it."

"How long do you think that will be?"

I looked at her and bit my lip, brow knitting together. I felt my palms begin to sweat.

"I'm not sure if you ever will, Mistress."

She smiled and nodded as if I had answered an exam question correctly. She looked over at Colleen, who gave her an impressed expression and a mock, silent clap.

"I'm sure you're worried that means you'll never get to have an orgasm again," Mistress said. "Of course, they will be far, far less frequent for you. And why is that?"

"Because a good sissy should be horny and have her mind on her panties and cage," I answered quickly.

Colleen let out a stifled giggle behind me.

"Right. Of course, you won't ever use your little clitty for cummies," she said, reaching out and poking my cage through my panties. "If you ever want to have an orgasm again, you'll have to do it the way a sissy girl is supposed to."

She hefted the dildo towards me with both hands.

"You'll have to do it with this. Perhaps my old disciple Georgiana can demonstrate."

I hadn't even heard her enter. She was laying on her side across a couch, her dress pulled up to reveal a tall garter belt and sheer panties. A small metal cage was clearly visible in them, her clit straining against the bars. She had a thick black dildo in her hands.

Is she going to use that —

Georgiana's panties were open in the rear, and she slowly slid the dildo between her cheeks, bending and lifting one of her legs as she did. She draped it over the back of the couch, allowing the dildo to enter her smoothly and easily. To my shock, she slid the massive thing down to its flared base before quickly pulling it out. Her head fell back as she let out a long, low moan of pleasure.

" That is what you're for, girl," Colleen said to me as I stared at Georgiana with wide eyes. "Look pretty, be desperate, and get fucked."

Hearing my life distilled so simply made my cage feel even tighter.

The purple dildo Mistress selected had a suction cup which she used to attach it to the glossy coffee table in front of her. It wiggled luridly at me, its thick, swollen tip staring up at me. It seemed enormous, far too big to fit inside of me. I trembled, biting my lip again and looking at Mistress with terrified eyes.

"Take off your panties, Michaela," she said firmly, nodding her head at it. "And prove to me I'm not wasting my time with you."

I pulled my panties down with shaking hands, setting them gently on the table next to the dildo. Georgiana was moaning and groaning, quickly thrusting her dildo deep into her.

Mistress trained her before me, I realized, finally connecting the dots. Well, I'm going to be better at this than she ever was. If she can do it, I can too.

And so I squatted backwards, letting the enormous purple head nestle between my cheeks. My cage hung between my legs, my clit dwarfed by the size of what was about to be inside of me. It pressed firmly against my rear entrance, barely spreading it just as Mistress' fingertip had that first day. I steadied myself on my tall heels, and gathered my skirts up in my arms.

Then I let it inside of me.

It split me open, filling me with a sick pleasure that made my stocking-covered legs tremble. I pushed down against it, lowering myself as best I could, feeling each of its curves and stretching from its thickness. I gasped as the head entered me fully, the weight of it pushing inside of me and making my cage twitch.

"That's excellent , Michaela," Colleen said with a clap. "Even Georgiana couldn't do anything like that on her first try."

I glanced at the other sissy and saw that she had paused her motions. She was seething at me, her lip curling into a sneer. The intensity of it almost startled me. I had to look away, back towards Mistress. Her expression was simple expectation, waiting for me to continue.

"Thank you, ma'am," I moaned as I continued to lower myself down the shaft's length.

It slid deeper and deeper into me, spreading me open and filling me in a way I'd never felt. The feeling made me buckle forwards, bending in half at my waist. My cage and package brushed against the dildo as I let it stretch me. The feeling drew another moan from me.

"Look at her!" squealed Colleen gleefully. "She's leaking already! "

I looked down, my thoughts hazy and vision blurred. I could feel something dribbling from the tip of my cage, a slender stream slowly dropping towards the floor. There was immense pressure building in me.

"Georgiana," Mistress Saskia said, her voice like cool air cutting through the room. "Come over here."

Georgiana removed her dildo and went to Mistress, looking straight ahead with a perfectly straight back. Silently, Mistress reached between her breasts and lifted a small silver key on the end of a slender chain. Georgiana stared at with eyes the size of saucers, her body stiffening in excitement. Ignoring her, Mistress lifted Georgiana's skirts and grabbed her chastity cage. The sissy sucked in a ragged breath.

"With your Madame's permission —" Mistress shot a glance at Colleen, who gave an idle nod and waved her hand in a dismissive way "— I think you need to show Michaela what her mouth is good for."

Georgiana's padlock fell away and Mistress removed her key, tucking it back into the depths of her dress. The cage fell from Georgiana's rapidly growing shaft, finally free of its confines. It was much larger than I expected, slender but long with a pink tip that bounced in front of her, parting the delicate layers of her dress like a curtain being pulled open.

Mistress Saskia looked first at me, then at Georgiana, nodding her head in my direction with raised eyebrows. The sissy didn't need to be instructed twice. She all but ran to me, shaft waggling. Like me, she was already leaking. A sticky smear spread on my lips as she pushed her against my mouth.

Am I really about to suck a cock?

Georgiana did not give me time to reflect. Her erection pushed open my lips and slid into my mouth, trailing pre-cum behind it. Her shaft was hot and salty, the taste of her pre-cum mixing with her sweat and the scent of perfume. Automatically, I wrapped my lips around it, thinking about all the times when a girl had done this to me.

And how much things had changed.

I reached my limit on the dildo, halting in a half-squat, my skirts flared around me. I could feel my muscles tense and relax around it, pulsing waves of pleasure coursing through me. Georgiana began aggressively thrusting herself into my mouth, peering down at me with smug satisfaction. My clit ached as it fought against the confines of the cage, my body overwhelmed with the pressure of the dildo.

"Georgiana was one of mine," Mistress Saskia said, leaning back in her chair. "I trained her, just like I'm training you. I'm very proud of how far she's come."

"She is a delight, " Colleen agreed cheerily. "Very obedient. Eager to please. Built for it, really. Dresses well. Honestly, Saskia, no one does a better job with them around here than you. You've really outdone yourself with little Michaela here."

Is she jealous of me? I wondered as Georgiana glared at me with a mixture of contempt and arousal.

She was thrusting in and out of my mouth with more than just the fervor of an unlocked sissy. There was an aggression there that went beyond that. She was going to take out all her frustration on me, prove that she was the finest sissy Mistress Saskia had ever trained.

Two can play at that game, I thought, furrowing my brow and sucking hard, swirling my tongue around her.

This was the first cock I was sucking, and she was going to make it as hard for me as she could. So I decided to return the favor.

Georgiana's gasp melted into a groan, her expression turning from smugness to surprise. Just as quickly as it appeared, it hardened. With determined motions, she grabbed the back of my head and began forcing my mouth along her length. Her shaft slid along my tongue until it was almost in my throat. I suppressed a cough and gag, remaining in place even as my eyes began to water.

"Oh my, look at these two go! " Colleen giggled. "Georgiana, do you have some sissy frustration you'd like to take out on Saskia's newest?"

Georgiana looked at her with a look of mock innocence before releasing me. I lurched backwards but managed to keep my lips around her, sucking tightly. I grabbed her shaft and began to stroke while I bobbed my head forwards and back. She moaned, pushing her hips forwards. This time I expected it and pulled back, keeping her out of my throat.

"If I'm being honest, I'd like to see her do a better job riding that cock," Colleen said to Mistress. "Wouldn't you, Saskia?"

"Yes, I would," Mistress said lightly. "Michaela, it's not enough to have it inside of you. I need you to ride it like you would a real one. Whoever it's attached to will expect pleasure, not just a hole. "

I closed my eyes and began to rise off the dildo, feeling it slip out of me. Cold emptiness flooded into me. I continued sucking Georgiana, twisting my hand along her shaft while I swirled my tongue around her tip.

You're going to cum, I thought angrily at her. And I'm going to prove that I'm better at this than you are.

As if reading my thoughts, Georgiana pulled out of my mouth completely and stared at me with contempt.

"You have to do a better job riding a cock than that, sissy," she said.

Colleen burst into laughter, swiveling her gaze to Mistress with a look that screamed can you believe she said that?

"And how would you do it, Georgiana?" Mistress asked with a humoring smirk.

"She's far too slow, for one," Georgiana critiqued. "And she's all hunched over like it's some sort of inconvenience for her."

"What do you think, Michaela?" Mistress asked. "Is this whole thing some sort of hardship?"

"No!" I gasped, feeling the truth of it.

"Then act like it!" Georgiana snapped, receiving a warning look from Colleen.

"Careful, sissy," she chastised, the laughter drained away. "Don't overstep your limits."

"I'm very sorry, Madame," Georgiana quickly said, bowing her head. "Forgive me, please."

"Only because you're correct, " Colleen said, turning her attention back to me. "Who wants to fuck a sissy who's not enjoying it? Straighten that back and ride the damn thing, girl!"

"Yes, ma'am," I said softly.

I leaned backwards, letting my petticoat fall around me in a cloud of lace. Georgiana took a step towards me and I snatched her shaft, stroking her and pulling her back into my mouth. I curved my lower back, trying to adopt a pose of pleasured happiness, as if the dildo was the only thing I wanted in the world.

Then I began to bounce.

If the size had been overwhelming, riding it quickly nearly made me explode. Wave after wave of stomach-knotting pleasure washed over me with every movement. I could barely focus on Georgiana in my mouth, even as she thrust into me with steady fierceness.

My legs burned from the effort. My skirts flew around me, my cage swinging up before clattering back down, my package bouncing off the dildo below me. I moaned around Georgiana's cock, stocking-covered toes curling. I felt more pre-cum squirt from my cage. I burned to be free of it, for our places to be switched: for my cock to be in Georgiana's mouth. I needed to cum so desperately, but even as a tight, hard pleasure built inside of me, I knew I wouldn't.

All I would get is frustration.

"Georgiana, you have my permission to cum," Colleen said. "Fill her pretty little mouth with your sissy cream."

"For how long has she been locked?" Mistress asked while Georgiana wrapped her hands around the back of my head again.

The sissy was moaning loudly now, a high-pitched sound that grew louder with every thrust into my cherry-pink lips. Her dress swung around her, petticoats brushing against my nose. I could tell she was close.

I wonder what it's going to taste like, I thought suddenly.

I'd never had a cock in my mouth before, much less tasted cum. The knowledge that I was about to made me surge in my cage.

"Let me see. How long has it been, Georgiana?" Colleen asked, though it was clear she wasn't expecting an answer. "Six months?"

Georgiana nodded, pulling my head against her while I bounced on the dildo. The pressure kept building inside of me. Even when I thought I couldn't take anymore it mounted, pressing outwards. It filled my arms and legs, my cage, my body. A burning need to cum, to finish, to be released! All it would take is one touch, a brush against my clit.

But the lock on my cage held, the tube in place, my clit hidden away.

"Fuck, your mouth feels amazing," Georgiana moaned above me. "I'm going to cum in you, sissy. Are you ready?"

I began to shake my head no. How could I be ready for this? How could anyone?

"I don't care," she squealed. "I'm cumming!"

Thin, sticky strands flew from her tip. I slurped and licked her while she came, feeling her buck and twitch around me. Her squeals turned into choked grunts as six months' worth of cum filled my mouth and ran down my throat. I swallowed it as fast I could, but there was too much — it began to dribble out of the corners of my mouth.

"That's quite the load, Georgiana," Colleen said approvingly. "Looks like little Michaela is struggling with it."

Mistress Saskia didn't respond. I felt a pang of fearful sadness. Had I disappointed her? Was I supposed to do better?

When Georgiana finally finished, her limp clit slipped out of my mouth. A long strand of cum ran from her tip to my lips, breaking as she fell backwards against the couch. I kept bouncing on the dildo, pre-cum spilling from my cage, Georgiana's cum spilling down my face.

"You can stop that, now." Mistress' voice came with a softness that unnerved me.

Gingerly, I stood, the enormous purple head sliding out of me and leaving me feeling empty and hollow. I turned to face her, barely able to look her in the eyes. Her expression was hard and unreadable, eyes narrowed while she stared at me. Her lips were pressed in a thin line.

"Next time, you swallow every single drop," she said tightly. "I expected better of you, Michaela."

I hung my head, surprised at how much shame I felt crush through my body. The pleasure, the pressure, the arousal all washed away in an instant. Even my cage felt looser. I wiped away a dribble of Georgiana's cum from my cheek.

"I'm sorry, Mistress Saskia," I said, voice barely above a whisper. "I'm sorry I let you down."

"Well, I thought you did a remarkable job," Colleen cooed from behind me. "Saskia, your standards are impossible! Look at the poor thing, trying to swallow a load that big."

Mistress said nothing. Her gaze remained on me. Colleen glanced between us with raised eyebrows.

"Well," she said slowly, trying to break the tension. "At any rate. Welcome to Coopersville, Michaela. Don't worry about this too much. You'll be getting plenty of practice. Isn't that right, Georgiana?"

The crumpled, panting form of Georgiana moaned an affirmative sound from the couch. She had fallen backwards with her legs spread, her clearly visible clit dribbling a small stream between her legs. Colleen snorted at the sight, shaking her head with a smile. She turned back to my Mistress.

"Be gentle with her, Saskia," she said quietly. "Give her some time to learn."

But Mistress just stared at me, her eyes hard. Demanding more from me.

Expecting the perfect sissy girl.