The Trials of Dave Pt. 01

Dave walked up to the check in desk. He was so nervous, after months of communication he was finally going to meet his Goddess. She said if things went well she would considering formalising their relationship and taking control of him fully, as long as he proved his dedication... whatever that meant! The receptionist was a pretty girl in her early 20s, bright red hair tied back in a bun engrossed in her phone. She looked up at him sternly with piercing demanding eyes which made him painfully aware of his chastity device.

"Checking in, Mr Jones, staying with Mrs Jones."

"Ah yes", her face softened as she corrected back into customer service mode. "Your wife is already here sir, some time ago. I think she went out again, but she left one of the keys for you, room 417, fourth floor." It seemed like there was a hint of a knowing smile in her face, but he dismissed it.

Dave thanked the lady and walked towards the elevator, before remembering he's supposed to always take the stairs, Goddess says that if he's going to lead the life she wants he needs to get fitter. He groaned a little but before he knew it he'd conquered them and was outside of the door to the expensive room he'd paid for. It did however take him a little while to catch his breath. His Goddess was right, he did need to be fitter, his waistline had grown considerably over the past few years.

He knocked on the door in case the receptionist was mistaken, after a few moments of silence he assumed she probably wasn't. He fumbled the key card as he nervously put it into the slot, watched the light go green and then entered into the room.

Inside the room he was met with a strong odour of intoxicating perfume. He felt weak almost immediately. His eyes were drawn straight to the four poster bed with its red silk drapes and sheets. Positioned on the bed he saw a white envelope. Eagerly he headed straight for it. It was addressed simply to "Sissy", as he turned it over he saw it was sealed with a lipstick mark, clearly from a kiss.

His heart skipped a beat as he carefully tore into the paper, determined not to damage anything. Inside was the most elegant handwritten letter he'd ever seen, he read it slowly taking in every word:

Dearest Sissy Davina,

The last few months getting to know you have been an absolute delight. However, I am looking for someone who will do whatever I say, whenever I say it, with no hesitation and no inhibitions, trusting that I will keep them safe. I want someone who will push through their embarrassment and their comfort zone to make me happy. Are you that person? You may well be, but I worry that you still listen too much to your ego brain and fight my instructions. If we are to continue to the next stage of this relationship I'm going to need you to prove that you can be the person I want.

I have set up a series of tasks for you, if you complete them you'll end the day you'll have the chance to pledge yourself to me in person. If you fail, then I'm afraid that will be the end of the line for us and I will be focusing my attentions elsewhere. If at any point the requirement is more than you can meet you have two ways to escape the situation; either say to whomever you are with "Cuttlefish", or, if you are on your own sit down on either a bench or the floor and raise your left arm in the air. These are your safe word/actions my pet. Remember them, and also remember there is no shame in using them if something is too much for you.

Your first task, is to remove your padlock and replace it with my own which is in the top draw of the dresser, do not remove your device. My sissy is my property and her pleasure is for me to control. Once you have done this read your next task. Good luck my darling little pet, I will be routing for you!

There was another lipstick kiss at the bottom of it. Dave realised he'd been holding his breath for some time, he exhaled and composed himself. After re-reading the letter to make sure he hadn't missed anything he walked over to the oak dresser by the window. He looked out at the Birmingham landscape for a moment, was this what he really wanted? It sounded like he was probably going to be pushed beyond his capabilities today. His Goddess was the only good thing he had going for his current life, his job was going nowhere, his inheritance wouldn't last forever and he hasn't spoken to his family in months. He caught his reflection in the glass, grimaced at his receding hairline and double chin. He was deluding himself if he thought he would ever have a better opportunity than this, now in his 40s he should be grateful that Goddess Amelia even acknowledged his presence.

Any doubt in his mind that he had that he had to try this slipped away. He opened up the draw and picked up the pink lock, which would go nicely against his steel cage. There was another envelope below but he knew he should complete them in order. He quickly pulled down his trousers and boxers, then retrieved his keys from his jacket pocket, found the one for his cage and swiftly unlocked.

How long had it been? Maybe a month since he last stroked, he was not allowed to keep count! Weakness filled him, it'd be so easy to have a quick orgasm now, when would he next be allowed the chance? He was so horny! But if he did would he really have the ability to do anything his Goddess asked for him? Then he knew he'd lose her for sure. Quickly making his mind up he snatched at the new pink lock and forced it onto his cage... Goddess Amelia smiled to herself as she watched via webcam just next door.

Dave's head was swimming, in all of his years playing with chastity he'd never been separated from the key to his cage. Now he'd just clicked a strange lock into place, despite never actually meeting the person who had given it to him, having no idea where they lived, their real name or even that they definitely had the key! He couldn't let himself think about that, this was about trust, and he did trust her, he had to trust her!

Dave picked up the envelope from the draw, and another that was sitting below it and took them over to a chair on the other side of the dresser. There was another lipstick kiss on the back of the one titled "Task 2". He pressed that against his lips, would he ever feel his Goddess's kiss actually on his lips?

He carefully opened the envelope and read his next instructions.

I like my sissy to wear pretty clothes. In the wardrobe you'll find your initial outfit, dress completely and leave your own clothes folded neatly on the bed. Then read task three.

He apprehensively opened the wardrobe. Hanging up was a long floaty floral, predominantly purple, dress, a racy black lingerie set, some black high heeled shoes and a blonde wig on a manikin head.

Dave didn't know what to think. He had dabbled in feminisation but only ever in the privacy of his own home, but this was what his Goddess wanted. He started carefully removing each item of clothing and folding as instructed. Once he was completely naked (except of course his cage), he turned back to the wardrobe. Here goes nothing...

It took him a little while to hook the bra on, and then get it positioned correctly, but it did cup his man-boobs pretty well. He realised this was why his Goddess had asked for his measurements a few weeks previously. Then he pulled up the lacy thong. The fit was tight, pressing his cage closer to his body, but overall pretty good. He was not used to the sensation of the almost permanent wedgie though, and instinctively reached to pull it away from the crack of his behind. He was starting to feel uncomfortable so quickly slipped the dress over his head to cover up more. He was relieved that it was very loose fitting and went down well below his knees. He slipped on the shoes, grateful again that the heels were only 2 inches, though even that was enough to make him unsteady. Finally he applied the wig, which came just below his shoulders.

Dave closed the wardrobe and looked into the mirror. He felt pretty ridiculous. Anyone with more than a passing glance would be able to tell he was a man, not even close to passing as a woman. At the same time he didn't think he'd ever felt so aroused. He stumbled back towards the bed, struggling with the heals, and picked up the next envelope.

Very good sissy, now it's time to go out into the world, proud of looking how I wish you to look. You are to walk to 'Bubbly Blondes' beauty parlour on New Bond Street and ask for Madame Roxanne. You must not take anything with you, no phone, no wallet, no keys, if you don't know the way then you are to ask for directions. Remember your safe word/actions, I won't let any harm come to you.

Dave was physically shaking now. He'd never been to Birmingham before and had know idea how to get around, he was going to be so vulnerable. It took him a full 5 minutes to make his way to the door, repeating again and again "Bubbly Blondes", "New Bond Street", "Madame Roxanne", "Cuttlefish".

He paused with his hand on the door, his last opportunity to keep his dignity. After a deep breath he turned the handle and walked awkwardly into the corridor and into the unknown...