The Next Step

George was a slight young man. Only a few years out of college and now that he was settled in at his job he was left with more time to indulge in his secret. A secret born out of a bet he'd lost to a friend back home years ago.

Now George sat in front of the mirror. Transforming from George to Georgette. Getting ready for his first date. A blind date of all things. His cock strained in its device and his ass quivered around the jeweled plug. He wished he had something to fill out black and lacy bra he wore, however the matching panties, garter and stockings always made his groin tingle.

Georgette looked into the full length mirror. A black thigh high dress, with ruffles to help cover his chastity bulge. White wrist length formal gloves. Black heels that laced up over his ankles finished off the outfit.

Georgette packed his phone, money, some make up and keys into his clutch, took a deep breath and stepped out. As the door closed he was now a she to the world.

Georgette soon felt comfortable she could blend in as she past by the other tenants in her building on the way out. Unnoticed.

Along the way apprehension swirled within. A blind date. That's not a step he thought. It was a leap. Georgette always wanted to take the next step, but a quick wank always let George back out of anything that risqué. The chastity device and some ED medication purchased online allowed him to build the sexual energy to give Georgette the courage to go out.

Some catcalls and a few head turns boosted her confidence as she made her way to the hotel bar they were to meet at.

Georgette felt her cock leak as she felt all the prying eyes giving her the once over when she sat down at the bar and ordered her martini. Just as her date directed her to do.

She grew nervous as she sat, waiting for a man she'd never seen before. Wondering how long it would be before the other men, who'd been eyeing her since she walked in, finally make an attempt to pick her up.

Georgette felt wild, free and alive. A sexual energy rippled across her skin. She wanted to race home and masturbate, but that was impossible. Her chastity cage was controlled by an app on her phone and it wasn't set to unlock for another two weeks. George wanted to run, but Georgette was in her glory as she felt the stares. She was here, in public. Not a slight, almost, effeminate male; but a petite beautiful woman. A woman who was actually getting attention.

Her hand covered her mouth as she stifled a laugh. She was awash with unbridled hormones. So horny. A sexual energy coursed through her veins.

Suddenly, Georgette froze, her drink inches from her painted lips as her eyes locked on her boss, Mr. Sanderson, staring at her from the other side of the bar. She watched as he slowly got to his feet and made his way around the bar to where she was.

The older gentleman sat down next to her. "Georgette?"

Georgette simply nodded.

"You're prettier than the pictures you sent." he said with a slight grin.

She was gripped by fear. 'He was my date!?!' she thought. 'Oh God. Please, no.'

"May I?" he said pointing to the stool next to her.

"Please."

John took a seat. "Bartender? Another for me and a martini for the lady."

Georgette gulped down the remainder of her drink. Wishing she could just run.

The new drinks arrived and John put his hand on her shoulder causing her to jump.

"Relax!" he said with a chuckle.

"I'm sorry. It's just..."

"Not used to going out."

"No. First time."

"A big step."

"It is. It took so long to build up the courage." she said meekly.

"Look at me Georgette." he said in a comforting tone.

She sipped her drink and turned to him.

"You could have come out on your own and chanced one of these wolves finding out your secret, but I'm with you and it's because of your secret. We talked about this. You and your secret are safe tonight. Relax and let yourself enjoy what you came out for."

"What I came out for?" she asked. She knew. Deep down she knew. She was so caught up with the fact she was actually going out in public as Georgette, she'd forgotten what she might really do. It started to sink in what might actually happen tonight.

"How long have you been a sissy?" he asked as he sipped his drink.

"A sissy?" No one had called her that before.

John smiled. "This is your first time. Isn't it?"

"Yes. A long journey to finally get to this point." she sipped her drink.

"Have you never?" he let the question hang there for a moment.

"Never." she gulped her drink and pushed the glass away. "I'd always chicken out at the last moment."

John moved closer and put his finger on her chin, turning her head back to him.

"Look at me. Your safe. And tonight your my sissy. You'll experience everything you've wished for. All your training and hard work will come to fruition."

He put a hand on her thigh and slowly started to slide it up. Her eyes still locked on his. Fearful that he'd recognize her. His hand finally stopped atop her panty clad chastity device.

"First, I need to hear about your journey. Tell me how you got here."

He moved his hand out from her crotch, brought his finger to her lips and wiped the dollop of her pre cum on her lip.

"Tell me and I promise you a night that you'll cherish for the rest of your days."

Her eyes were locked on his. A jumble of sissy hypno videos flashed in her head.

Her tongue licked the precum off her lip like a lizard catching an insect.

"Bartender." she barked, breaking their gaze.

Once the drinks came Georgette took a deep breath and a sip of her drink.

"I lost a bet to a girl and I had to dress up like a prostitute for a Halloween party. After the party we had sex, but she made me stay in costume. She lay on top, missionary, but I had to spread my legs and wrap them around her."

"Very psychological." he added.

"It was. She talked to me as if she were a John and I was a whore she bought for a good time."

John listened intently.

"After that time I tried to see her again. She said only if I dressed up."

"And you did."

"A lot." she nodded. "She would call me and we would meet, she paid me. She would treat me like a cheap whore. I would have to wear multiple condoms so that I wouldn't cum. She would climax, pay me and then leave or kick me out. Depending. The more we met, the more I wanted to dress up. To be taken. Used." As she spoke her tone changed from a story to a confessional of a dark secret.

"And then."

She sighed. "She moved to another school. I floundered. Sex was no longer interesting if I wasn't dressed, but I couldn't trust anyone else with this secret and living on campus prevented me from going further."

"Frustrating, I'm sure."

"Very and after college I got my own place. Free to do as I choose. Lingerie at first. Then outfits. Shoes and so on."

"But you're still just wearing women's clothing. Still frustrating. Like something was missing. A void that needed filling. An itch to be scratched."

"Yes. Yes! Make up, exercise, pampering. The more I did, the emptier I felt." she added. Excited to hear someone who understood her plight.

"It wasn't enough." he added.

She shook her head.

"You needed to know what it was like to be a woman, not just dress as one."

She nodded, her hand shook slightly as she sipped her drink.

"Which came next? Toys? Videos? Something else?"

"The more I dressed and trained; the more aroused I became. The more videos I watched. Hours and hours of audio. Teaching. Training. I did it all. Yet I wasn't satisfied."

"Only one thing left."

She nodded. "Yes."

"But you couldn't take the next step."

She shook her head. "Yet it burned inside of me."

"It is a very big step. Here you are though." he responded. "Seeking the satisfaction you crave."

"My device really helped. Well, that and some pharmaceutical assistance." she chuckled. "And a whole bunch of porn."

"What did you do with the key? How did you keep from unlocking it?"

"No physical key. There's an app on my phone." she said holding up her smartphone. "I programed it for a month."

She opened the app and showed him.

He flipped through the app. "Very interesting."

"Excuse me. I need to powder my nose." she said and walked off to the bathroom.

John continued to browse the app while she was gone. He put the phone down moments before her return.

"Mmm. How long did it take after you programed it before tonight?"

"Two weeks." she looked up at him. Still in disbelief that she was talking to Mr. Sanderson. The man that George would talk to at least once a day.

"So much training, preparation. All to bring you here. Tonight. Are you ready now?" he asked flatly. "Don't say no. Your damp panties betray you."

Georgette's hand was shaking as she tried to sip her drink.

John leaned in and put his arm on the back of her chair. He took the glass from her trembling hand. Then took her hand and put it on his leg.

"What are you Georgette? What have you been training to become?"

"A sissy."

"What kind of sissy?"

"A sissy whore." Georgette replied. Her libido and alcohol taking control.

"No Georgette. Not a whore. Unlike your college friend I don't pay for sex."

"I'm sorry." she said apologetically. "I don't think I can."

John held her arm to keep her seated.

"What is it you want sissy? What do you truly desire?"

She swallowed hard as she slid the hand up to his crotch. It brushed over his cock. Her nervous eyes stayed locked on his as she gave it a good squeeze.

"Tell me sissy."

"This."

"And what is 'this' Sissy?"

"Cock." she whispered, her heart pounding in her chest. She was flush and dizzy as she spoke. "A real cock."

"A hunger for it?"

"Yes." she squeezed and rubbed it. Her eyes went soft and her lips parted slightly. Allowing a small gasp to escape.

Georgette was still in disbelief. She was out in public, allowing herself to be seduced by a man. A man who happened to be George's boss, trolling for sissies, seducing, unbeknownst to him, his employee.

'A real cock; in my hand. So warm. So thick.' she thought. Her own crotch tingled.

"What does that make you?"

"A cock hungry sissy." she cooed. Her body awash with an explosive energy.

"Is that what you've trained yourself to be?"

"Yes." she said as her soft submissive looked at his.

"Are you ready to take the next step?" he held up a key card. "It's closer than you think."

She squeezed his hardening shaft. "Please." she whispered and paused.

"Address me as Master from here on out and it will happen."

Her pleading eyes locked onto his. "Please... Master."

A grin spread across his face as he gulped down his drink and stood up. "Let's go make a real sissy slut out of you."

She stood and smooth her dress with gloved hands as he paid the tab. 'Sissy slut.' she thought. 'A real sissy slut.'

John held his crooked arm out and she hooked hers into his as the walked to the elevators.

Georgette's head was swimming. She felt the eyes upon her as the handsome gentleman escorted her to the elevators. Her body tingled as she could almost hear the lewd thoughts going through their heads.

He let her enter the glass elevator first and as soon as it began to ascend he pulled her in and kissed her deeply, his tongue invading her mouth as a hand slid to her ass. One of her legs reflexively kicked back as he kissed her.

'Taken. Used.' she thought.

He released her as the elevator dinged and the doors opened. She blushed and exhaled, brushing her hair behind her ear.

'This is it.' she thought. 'The next step.'

She followed him to the room, her heart pounding in anticipation.

He slipped the key into the reader and opened the door.

"Last chance." he said as he held the door open. "If you back out I'll understand. I'll be disappointed, but I'll understand."

"The next step." she whispered as she brushed past George's boss.

He grabbed her ass as she went past. "Your my sissy now."

Georgette looked around the suite as John went to the minibar.

"Drink?"

"Please."

John stopped and stared at her.

Georgette grew nervous and looked around.

"Would you like a drink... Sissy?"

She cleared her throat. "Yes, Master."

"Better." he responded as he went to making drinks. "Now lose the dress. Leave everything else on."

Georgette worked herself out of the dress and waited awkwardly in the center of the room. A mixture of fear, apprehension and lust swirled within. Her mouth watered and her plugged ass quivered. Her cock swelled and soaked her black lace panties.

"My, my. Look at you. You are a sexy little tart." he said as he brought her her drink. "Does your lingerie make you feel like a sexy sissy? Eager to become a real sissy?"

He sipped his drink. "Well, I think you're very sexy."

"Thank you Master."

They stood together, drinking. An awkward silence developed.

"Master?" she inquired.

"You look like I should know you. I can't place it."

She tried to controlled the panic sweeping through her. "Another cock hungry sissy perhaps?" she said with a sly grin and seductive eyes.

"Squat." he snorted, taking the glass from her and then pushing her down.

He tilted her head back. "What are you?"

"A cock hungry sissy, Master."

"Well, let's satisfy that hunger. Go to work Sissy. Make your Master proud."

Nervously, she worked his pants open and pulled them down. Her gloved fingers slid across his thick shaft. She was taken aback by its size as she gently caressed it, watching it slowly grow. Although she'd practiced nightly on her gag reflex; she knew her limits were about to be tested.

It swelled past six inches and was still growing. She glanced up at John and kissed the tip. Again. And again. Her tongue swirled across it. She teased the head as his thick eight inch monster came to life as she held it. Her other silk covered hand cupped his balls.

She moaned as she began sucking on the head. Slowly taking more and more in. It seemed to take forever as she worked more and more of him into her mouth. She had worked herself up to a ten inch dildo without gagging, but his girth tested the limits of her mouth.

She impaled herself almost to the base, moaning seductively. She hummed loudly and rubbed her nose on his belly. She glanced up, seeking his approval. Georgette found that although he was much larger than her dildos, actual flesh was much more pliable than the toys she had.

"Well, you have been training haven't you?" he said mockingly placing a hand on her head and pulling her off. "Now what kind of sissy are you?"

"A cock sucking sissy, Master." she replied, wiping saliva from her chin.

"Very good. Back to work." he said, pushing her head back on to his cock. "Let's get me ready for your breeding."

She worked the warm shaft of flesh in and out of her mouth. The briny taste of his precum coated her tongue.

'You finally did it.' she thought. 'Your first cock.' She always enjoyed following the directions of the sissy training videos, but now to hear the soft moans of pleasure coming from John set off fireworks of lust inside of her. She worked his cock deftly. Mixing quick short strokes with long deep throating along with passionate moans.

"You're a natural Sissy. Born to suck cock." he said resting his hands on her head.

She didn't even hear him as she was consumed with bringing her first cock to orgasm and savoring her first load.

As she felt his hands grip her head and his body tense she began to piston her head on and off his massive tool. Going as deep as she could with each thrust. Eager to bring about his orgasm.

"Yes. Suck it, Sissy. Suck it good." he grunted as his body tensed and a leg began to quiver.

"UGH!!! Swallow it! Swallow every drop you little slut." he grunted through gritted teeth. He held her head firmly as he push himself in to the hilt.

Georgette was taken aback as his thick rod exploded in her mouth. Spewing wave after wave of warm milky sperm into her throat.

He held her fast as his climax wash over him.

Squatting in front of him with his rod stuck in her throat, she began to panic. She learned to relax her gag reflex, but now he was lodged there. Plus she struggled to swallow all he was injecting into her. Struggling for air she began to pull away and slap his legs.

Suddenly it all went wrong. She began to gag and cough. In her panic some of his cum went up instead of down and soon shot out of her nose.

John finally released her head and she instantly collapsed to the ground, coughing and wheezing.

"There." he said with an bit of arrogance. "Now you also look like a cock sucking sissy."

John stepped out of his pants and took off his shirt.

"Make me a drink Sissy." he demanded as he sat down.

She sat there, crumpled on the floor. Tears, cum and saliva smearing her make up. Yet, all she could do was drink in the sight of his hard and muscular body. She'd never seen him out of his suit and tie. Her caged dick twitched in anticipation of what was next. Her ass clamped down on his plug. Any apprehension gave way to a desire to give herself to him.

'Taken. Used.' she thought.

"SISSY!" he barked. Breaking her train of thought. "My Drink!"

Georgette wobbled to her feet and worked her sore jaw.

As she leaned across the table to get his glass he grabbed her arm that was on the table and gave her a hard slap on the ass with his other.

She let out a shriek and jumped.

He held her hand and kept her from standing upright. She looked over her shoulder at him in shock and disbelief.

"When I tell you to do something, you do it. Do you understand?" he barked.

"Yes."

SMACK.

"Yes what?"

"Yes Master." she replied apologetically. "I'm sorry Master."

Smack. Smack.

"I'll send your your useless ass down to the lobby just like you are if the next step is too much for you."

"Please Master. I'm sorry. I'll be a good Sissy. Please."

SMACK.

"You need to be punished Sissy."

"I understand Master."

"You can take the ice bucket and go fill it up or get my belt and bend over."

Georgette stood there in shock. Pain or humiliation.

She knew what the belt meant, but he didn't say for how long. His ass still stung from his open hand.

A trip to the ice machine was different. In lingerie.

"I would like to get more ice Master."

"Don't dawdle or you'll get the belt as well."

"Yes Master."

She hurried off, taking the bucket with her; pausing at the door, which had a full length mirror on it and took stock of her reflection. Her tussled hair, smeared makeup and sperm running from her nose and caking on her upper lip. Clad only in her lingerie, gloves and heels. She was shaking as her hand opened the door. 'You were born a sissy.' an erotic voice echoed in her head.

The hotel had an open atrium. All the rooms faced the open center, all the elevators were glass. She would be completely exposed, to multiple floors and all of the elevators for the entire journey.

Georgette jumped as the door closed behind her. The ice machine seemed to be a mile away. In reality it was only 10 doors down. She steeled herself and fought back her emotions. She took a deep breath and was flooded with the musky scent of his cum that coated her nostrils.

She walked with false confidence, ignoring the looks from across the way or the elevators.

'All they see is another bimbo, out for ice on a wild Friday night.' she thought. The trip turned out to be uneventful. No jeers or catcalls. No confrontations or molestations. It's not that she went unseen. To the contrary, many had viewed her. However, none were close enough to see through her facade.

She knocked on the door, but there was no response.

She knocked again.

"Master?"

Knock. Knock. Knock.

"Master?"

Knock. Knock.

"Please Master."