Mistress Sylvia Pt. 01

She pointed to the large front doors of the mansion.

"At that time I'll show you around the slave's quarters and spend an hour or so making it very clear what will be expected of you. After that you'll be required to commit or leave. Do you understand me Debbie?"

He made momentary eye contact and looked very intimidated, which pleased her.

"Yes Madam Bartolo, I do."

She pulled off her head scarf and held it up in front of him.

"Take it home fag and do whatever you want with it. If you don't show up tomorrow I'll never see you again, so I couldn't care less what you do. However, if you do show up tomorrow you better have it with you, and that scarf better be spotless. You see fag, if you want to be my slave then you are forbidden to jerk off with it. That's your first order from your new mistress and you damn well better obey it. Do you understand me Debbie dear?"

He took the scarf. "Yes Madam Bartolo, I do."

"Good, then bugger off fag."

She opened the door, got out and disappears into her mansion.

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Debbie arrived at Sylvia's home at ten o'clock and parked in the same place he did the night before. Even though the estate was somewhat secluded he felt extremely vulnerable as he ascended the stairs in full drag. He'd selected his orange wide-wale corduroy skirt and vest outfit, it was one of his favorites. Under the vest he wore a white, long sleeve, ribbed-knit turtle neck top, which was stretched over his bra and medium sized breast forms. The skirt was full, pleated and came down below the knee, and below that he donned a pair of light brown cowboy boots. Under his skirt he wore nothing. He initially debated wearing a pair of orange tights, but finally decided that if things went the way he thought they might, Sylvia would be pleased with him for providing easy access to his balls and ass. The cool autumn air actually felt good under the heavy skirt. He again had on his blond wig and he went a bit heavy on the make-up in an effort to look a little slutty, he hoped he didn't overdo it.

Despite the fact that the butterflies in his belly were multiplying by the minute he was very turned on, in fact he was beginning to get a boner. He took a deep breath and rang the doorbell. It took a minute, and when the door finally opened Mistress Sylvia was standing tall and looking down at him. She didn't smile, in fact she showed no emotion at all, she simply said.

"What do you want Debbie?"

He hesitated for a moment and wondered if he'd made a mistake. She was wearing a double breasted pantsuit that made her look very powerful, like she belonged in the boardroom of some big company. He suddenly feared that she was on her way out the door and wasn't expecting him at all. Had she forgot the night before?

The suit was obviously tailored and fit her large frame like a glove, snug but not tight, it hugged her form perfectly. It was done in a chocolate brown mid-wale corduroy that looked like it would be heaven to touch, and just like her outfit the night before the fabric looked plush and expensive. It was a very attractive outfit, and even though it was a business suit it was cut in a soft feminine manner. He wondered how much money went into keeping this big strong woman looking so feminine and beautiful.

She continued looking down her nose at him and waited for an answer. Not really sure what to do he brought his hands from behind his back and held up her scarf, as if that explained everything. She made no effort to take it and instead folded her arms across her chest and sighed. Her face took on a look of annoyed impatience.

"Tell me fag, did I misjudge you last night?"

He suddenly realized there'd be no easing into their new roles, he'd seen that look on Mrs. Monroe's face many times before and he knew what she wanted. He dropped to his knees right there on the stoop, bent over and began kissing her light brown pumps.

"Mistress Sylvia, may I please be one of your fag-slaves?"

"I can't hear you fag, speak up!"

In a much louder voice he continued.

"Mistress Sylvia, please let me worship you. I know I'm not even worthy of licking your turds, so please train me and make me worthy. I want to worship you."

She'd never had a fag beg to be a turd licker the first time on their knees, and it impressed her a lot.

"You are everything Mistress, and I am nothing, I exist only to service you and please you. I'll do anything you desire of me willingly and to the best of my ability. May I please show you what a good pussy-licker I am Mistress, I want you to see how well I can pleasure your magnificent body."

She laughed out loud. "What a stupid little shit you are. You'll be sticking your tongue up my asshole a half dozen times before you ever get to lick my pussy. You'll show me how well you use it in my rectum first. Got it fag?"

"Yes Mistress I understand completely. May I please lick your beautiful bottom, please Mistress, please may I stick my tongue up the Queen's shitter. Pretty please Mistress?"

She liked what she was hearing and let him beg for a few more minutes before cutting him off.

"Alright turd, shut up and get inside, but first give me my scarf, and you better pray it's spotless."

He handed her the scarf and began to get up, but as he did she grabbed his shoulders and pushed him back down.

"Where the fuck do you think you're going turd?"

He looked up with confusion written all over his face.

"Mistress Sylvia, I'm sorry, I thought you told me to get inside."

"That's right sissyboy I did. You've earned the privilege of entering my home and you'll do it like every other fag-slave before you, on your hands and knees like a good little doggie. Now move!"

Her voice had suddenly become a lot sharper, so he did as told quickly. He crawled past her into the large foyer, and as he did he snuck a peek at her trousers. Being that close he desperately wanted to rub his face against the soft corduroy fabric, but he sensed that would be suicide.

Once inside, she walked right past him saying. "Follow me fag."

She entered a room to the left of the foyer and he obediently crawled behind her. The wood paneled room was small, had bare walls and only two pieces of furniture, a comfortable looking armchair and a simple wooden desk chair. Naturally she sat in the armchair and he, not being stupid, stayed on all fours next to the desk chair. She sat with her legs crossed and inspected her scarf.

"This is my screening room, if anyone arrives without an appointment this is where they sit and state their business. Few people ever get past here."

After a minute she told him he could sit in the chair and he obeyed. Sitting up straight with his knees together and his hands folded in his lap he looked like an obedient schoolgirl. She gave the scarf one last look, shrugged and threw it at him.

"I guess you were a good little faggot last night, it looks very clean."

It hit him in the face and fell in his lap.

"You can keep it Debbie, but you're still forbidden to let it touch your sissy little penis."

She pulled a pack of cigarettes from her jacket pocket and lit one, there was no holder today.

"Alright fag, I'm going to explain some things to you, and if you have any brains in that sissy head of yours, you'll keep your mouth shut until I tell you to open it. Understand Daisy May?"

He nodded, and she blew a large plume of smoke toward the ceiling.

"You've made it quite clear that you desire to be one of my slaves. However, I never take on one of you sniveling wimps until I've explained exactly what will be expected of you. So let's start at the beginning. The moment you crawled into my home fag, you left your masculinity, your free will, your ego, and your dignity on that stoop. Is that clear?"

He nodded.

"Now listen carefully wimp, your useless sissy balls now belong to me. I'll do with them whatever I wish. And trust me fag, you don't want to find out what I'll do to them if you piss me off. Once you become my slave it's for keeps, and you don't leave here with your balls attached unless I allow you to."

She took another drag and studied his face. He seemed nervous but not scared, and she was impressed by that.

"And in your case fag, which is pretty unique, there's something else I now own, and that Debbie dear, is corduroy. That's right fag, I know there's nothing in life that turns you on more than corduroy, and if you're a good little bitch you'll get many corduroy rewards. But if you piss me off, or are disobedient in any way, I'll make corduroy disappear with a snap of my fingers. Am I making myself clear Debbie?

He nodded, and she sensed he didn't like hearing the last part.

"I love when a slave gives me a tool to control them with, and you've certainly supplied me with a good one."

She gave him a snotty smile and took another drag.

"But I don't think we need to worry about punishments right now because I have a feeling you're going to be an excellent fag-slave. And because of that, corduroy will play a big role in your training. Make no mistake fag, that's not a reward. I'm only doing it because I firmly believe keeping you in a constant state of arousal will accelerate your learning curve.

However. If you prove to be a slow learner, or I get bad reports from your trainer Joan, I'll have every item of corduroy clothing removed from this estate so fast it'll make you head spin. Am I making myself crystal clear Tinkerbell?"

"Yes Mistress Sylvia, I understand and I'll be very obedient."

"For your sake sissyboy, I hope so. Remember this Debbie, the better you behave, the more opportunities there will be for rewards. And in your case those reward will probably involve a lot of corduroy."

She put out her cigarette and steepled her fingers in front of her.

"Now comes the part where most of you fucking sissies go running back to your mommas. After your training is completed to my satisfaction, and you've earned a place as a fag-slave in my stable, you'll then start earning your keep. As you'll soon see, I love my fags and I take care of them completely. Their food, shelter, clothing and medical needs are all taken care of by me. I even supply them with a small allowance every week, which permits them to purchase some items for their personal enjoyment. Of course, the amount of that allowance is determined by how well they perform their job. My head fag-slave Joan, who you'll meet shortly, has even earned a position where she gets two days off a week to do as she pleases. In return for my generosity however, I expect my fags to be very obedient. They'll do whatever I demand of them at all times, and without question. If not, they are severely punished.

Now, to put it bluntly fag, when you become one of my slaves I become your pimp and you start whoring for me. Over the years I've developed a loyal client base and my fags keep them happy and coming back for more. You'll be an eager and willing whore to about a dozen dicks a day, five days a week. Occasionally there may be a few pussies in the mix, but you'll spend ninety-eight percent of your time being pumped full of sperm in one end or the other.

My clients pay very well but you'll receive none of it, you'll eagerly prostitute yourself simply because I tell you to. Joan is in charge of coordinating all the whoring, and you'll be as obedient to her as you are to me. If you perform your job well Joan will provide you with your allowance. You may also find yourself receiving rewards from me, and your one on one worship time with me will probably increase, which I'm sure you'll enjoy.

Now I want you to understand something before we go any further. I don't sell your asses for the money, I have no need for it. Besides, what you fags bring in covers less than half of what you cost me. No Daisy May, I do it because I love obedience and servitude. Knowing that you little whoring homos are worshipping dick after dick, day after day, just to obey me, pleases me a great deal."

She smiled momentarily as if relishing her own words, then resumed her icy stare.

"On the other hand, nothing in this world pisses me off more than a disobedient faggot. And bitchboy, your sissy balls will find out just how much if you ever disobey me in any way."

She let the words hang in the air for several seconds, then asked.

"Do you have any questions fag?"

He slowly shook his head and she found it a little odd that he didn't. Usually a prospect had plenty of questions by then, in fact it was normally the make or break point. She'd never had one simply accept all her terms so easily.

"Now to save us both time, after what I just told you, do you want to leave now, or are you prepared to be one of my whores?"

Without hesitation he said slowly. "Mistress Sylvia, I want to worship you in any way that I can. I'm eager to do whatever you require of me to prove to you that I'm worthy enough to worship you in any manner you desire. I'll gladly suck a hundred dicks if it'll get me one chance to lick your pussy. Yes Mistress, I'm willing to be whatever you want me to be."

She was bit stunned but didn't show it, she'd never had a fag be so willing so early before. She gave him a long hard stare searching his face for a tell, anything to indicate that he was bullshitting her to get what he wanted, but she found none. His voice and demeanor left her convinced that this fag was a genuine slave waiting to happen. She cleared her throat.

"Well Debbie, I'm very glad to hear that and I've decided we'll take the next step. Very shortly you'll be shown where the fags live, work and play. You'll then be introduced to Janice and Joan. After Joan explains what your day to day life here will be like, I'll expect a definitive answer from you. At that time you'll either leave or I'll turn you over to Joan to get you started on your training. But before we do that, I have one last thing I want to discuss.

When I'm not around you're to obey and worship Joan as if you're worshipping me. Joan will be in charge of your training, and within my guidelines she has permission to punish you without consulting me first. That means bitch, Joan can make your life here a living hell if she wants to. And know this tinkerbell, if at any time there's a problem between you two, I'll side with her in an instant. You may be a promising prospect, but Joan has been my loyal bitch for several years now. So don't let a problem develop, because faggot, you'll lose if it does.

I've instructed Joan to include corduroy in your training in many different ways. Unfortunately for you fag, she's dead set against the idea and I understand why. She thinks I'm giving you a reward before you've proven yourself worthy of one, and she resents the idea of a worthless turd like you receiving any special treatment. Especially when she's the one who has to provide it."

She saw concern developing on his face.

"Don't worry fag, Joan may have power over you but she's still my bitch. She'll obey me or I'll have her sissy balls in a jar. However, in the interest of fag harmony, I suggest you be the best bitch you can be for her at all times. If she gets mad at you, treat her even better. Understand fag? Win her over with obedience and worship, I guarantee you that once she realizes you're as good a prospect as I know you are, she'll come around."

She lowered her hands, folded them across her breasts and her face took on an almost pleasant look. She even smiled a bit.

"I'm going to give you a little tip that'll get you on her good side quickly, but what I'm about to tell you is to never leave this room, and if you value your sissy balls at all, you'll see to it that it doesn't. Understand fag?"

He nodded and looked intrigued.

"Joan loves having her toes sucked on. She gets extremely turned on by it, but it also embarrasses her, so only a few people know about it. If you make her think that you really love sucking toes you just might win her over very quickly. But don't be obvious about it moron, you're not supposed to know. I suggest you beg to kiss her feet a lot, and when she allows you to let her know that you really love sucking toes while you're doing it. Then fag, wait for her to make you do it. You be smart about this Daisy May, and when it comes to Joan your life might be a whole lot easier."

She smiled and looked off into space for a moment.

"OK, I've said all I have to say about that, in fact I've probably said more than I should have, and you better make damn sure I don't regret doing so."

She checked her watch and let out a sigh. "Alright sissyboy, it's time for us to get moving, let's go, follow me. She got up and headed toward the door. Debbie immediately got down on all fours behind her, and starts crawling. As she went through the door she looked back over her shoulder and stopped.

"No-no sissyboy, get on your feet, we have a lot of ground to cover."

He scrambled to his feet and followed her, rubbing his penis through his skirt while he ogled her corduroy covered ass. She was right, it was a long walk to the back corner of the estate where they came upon a set of doors marked Do Not Enter. Once inside the slave area, or dungeon as some called it, they walked down a hall of what looked like bedrooms, each of them empty but looking lived in. She said nothing the whole way until they arrived at the last room at the far end. It had a single bed, dresser, chair and a night stand, and it was obviously not being used. She stood in the doorway and motioned inside.

"This fag, is where you will live."

She pointing to the closet.

"That closet could wind up full of corduroy clothing, or it could remain just as barren as it is now, that all depends on how obedient you are."

She watched him scan the room, and after seeing the camera in the corner of the ceiling he looked at her puzzled.

"That fag, will remain on until your training is complete. You'll be watched at all times, so don't even think about jerking off without permission. There's another one in the bathroom."

She paused to light a cigarette.

"Blind obedience is your best bet faggot, because any attempt to disobey me or Joan will be spotted, and you'll be punished severely. And if you become a discipline problem, trust me turd, you'll find yourself living in a place a lot worse than this.

Take a good look around Debbie dear. Then we'll head to the playroom."