Mistress Kate Pt. 02

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking fag-slave until he paid off his debt to O'Reilly. On the way home he'd resolved to do no such thing, and as he downed his first drink it supplied him with the liquid bravado necessary to back it up.

His anger and resolve lasted through the second drink as well, but by the time he poured his third the beacon of reality had pierced the fog. He remembered that by agreeing to do exactly what Kate said he'd literally dodged a bullet from Reagan. Like air escaping from a leaky tire his defiance slowly abated, and as it did the memory of how sexy she looked in her corduroy outfit caused his dick to stir in his pants. Even though he wanted to deny it, the idea of being her bitch was very exciting. In fact, it only took about fifteen minutes before his dick was sticking out of his pants and he was slowly stroking it with one of his corduroy skirts. She'd told him to enjoy jerking off with corduroy tonight, because starting tomorrow he'd be forbidden to do so without her permission. He decided to heed her advice.

Around ten o'clock the doorbell rang, and after quickly shoving his dick back in his pants he opened the door to a very strange sight. Standing in the doorway was a tall effeminate guy dressed in a blue girly jumpsuit. He held a clip board and package but didn't look like any delivery man Jordan had ever seen before. In fact, his looks and demeanor spelled out "FAGGOT" in capital letters a mile high. He gave the bulge in Jordan's trousers a quick look and a smile, then turned his attention to the clip board.

"Are you Leslie Bains?" Emphasizing "Leslie".

No one ever called him that, very few people even knew the L in his names stood for Leslie. He immediately suspected it was Mistress Kate's way of trying to humiliating him.

"Yeah that's me."

He reached for the package but the fag pulled it back.

"Wait a minute sweetie, she wants you to sign for it."

He handed Jordan the clip board, and after signing they exchanged items. Before he turned to walk away the fag added to his embarrassment by giving him a wink. As he closed the door he wondered why they entrusted such a large sum of money to such a wimpy looking fag, but then he remembered they couldn't use any of Regan's goons, so he guessed they used one of Kate's sissyboys instead.

He sat down and immediately opened the package. Inside was a black corduroy cash bag, and inside that, a four inch stack of bills. Pulling it out he couldn't believe his eyes, and after fanning the stack his hands began to shake a little when he realized what he was holding. She said the package would contain a $100,000, and he guessed the stack contained one thousand $100 bills. He downed the rest of his drink. He'd never held that much cash before and for a while he just sat mesmerized by it. Between the alcohol and the thrill of holding the cash, after a few minutes Kate's prediction came true and he started devising a plan to run. His mind toyed with the idea for several minutes, and as it did he picked up the money bag and gave it a closer look. He'd never seen one made of corduroy before and something told him it probably wasn't very common. He suddenly wondered if using a corduroy bag was her way of reminding him not to run. That thought put a quick end to his flight fantasies and he returned the money to the bag.

He poured himself yet another drink, then packed a couple of suitcases and laid out the outfit he planned on wearing the next day. It consisted of a long black wide-wale corduroy skirt, light green wide-wale corduroy big shirt, black bra with large breastforms, light green tights, black corduroy Mary Janes and a shoulder length curly black wig. He had several outfits that were far sexier, but since he'd be driving while in drag, from a distance he thought the big shirt would be less conspicuous.

After his suitcases were packed he set his alarm clock, then laid down on the bed. Even though he was drunk and worried he was also very horny, part of him was actually looking forward to spending time with Mistress Kate. She was a very sexy woman. Maybe the full time slave stuff was just bullshit, maybe he'd only have to worship Regan/Gloria's dick for a few weeks before they'd leave him alone. With them both dressing in corduroy drag he could easily live with that, in fact he'd enjoy it. Remembering that he and Regan both shared the same fetish made him even more excited and he had to do something about it. He pulled off his trousers, laid them out neatly on his belly, wrapped one of the pants legs around his boner and started masturbating. As he did he fantasized about Gloria and Mistress Kate dressed in corduroy, and it didn't take long before he pumped a big load of creamy jizzum all over the front of his pants.

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The clock radio was screaming Let's Get Excited by the Pointer sisters, but at that moment he was feeling hung over, not excited. He Got up, took a piss and decided to get dressed. When he picked up his pants however, he noticed the dried jizzum all over the front of them. So he pulled another pair of pants out of his suitcase and put them on. He had a cup of coffee, thought about his dilemma and tried to find a silver lining, but it wasn't working. Thoughts of flight returned momentarily, but he dismissed them quickly.

When the time came to go he sighed deeply, grabbed the money bag and headed to his car. As he drove across town the fact that he was carrying such a large amount of cash began to scare the hell out of him, and he felt relieved when he arrived. The goons did indeed insist on checking his bag, and when the inspecting goon let out a long low whistle it convinced Jordan the charade had worked as planned.

O'Reilly was sitting behind his desk in the same t-shirt and corduroy jacket he had on the day before. Jordan had no intention of asking him why, but it did cause the memory of Regan on his knees sucking his cock to flash through his mind, and that made the whole interlude feel very weird. He handed Regan the money, and after checking it, he told Jordan to sit.

The Leprechaun was hard to read. He seemed a little embarrassed, which would be natural after being forced to suck Jordan's dick, but he wasn't overly so. He didn't seem pissed off either, as if regretting what he did, and that relieved Jordan a great deal. He obediently sat in the chair and Regan spoke in an even tone.

"Wait here five minutes, then leave, and when you do look relieved."

He returned to his computer and proceeded to ignore him. As Jordan sat he occasionally snuck peaks at Regan and fantasized about the two of them in drag. The idea of sucking Gloria's cock suddenly became very appealing, and he had to fight off the urge to rub his dick through his trousers. The minutes went by quickly though and he left without a word.

Arriving home he spent the next hour slowly dressing in his sissy outfit and having a drink. Yes it was early in the morning, way too early for a drink, but he was so nervous he didn't give a shit. He was hung over and minutes away from driving across town dressed in drag, going to a professional mistress's house to do God knows what. At that point becoming an alcoholic was the least of his worries. When the clock told him it was time to go he panicked a little, but since the money was gone, there was no more incentive to flee. He accepted his fate and headed out to do whatever the fuck she had in mind for him.

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Kate's house was on the western edge of town. It was a large white two story colonial hidden behind a row of high bushes, which provided its yard with privacy. Jordan parked behind the house, put on his wig and spent a minute trying to settle the butterflies in his belly. Taking a deep breath he pulled the suitcases from the rear seat, headed to the back door and timidly rang the bell. A minute later the door opened revealing his new mistress and he actually gasped. She was stunning. She was clad in a pair of black mid-wale corduroy jeans that looked plush and expensive. They were similar to the pants she wore the day before, and they fit her like a glove, snug but not tight. On top she donned a black mid-wale bolero jacket over a scarlet red tube top, and the top was taut over her large firm tits. Her hair looked beautiful cascading over her shoulders and her make-up was done tastefully, there was no sluttiness like the day before. Below she wore red corduroy ankle boots with three inch heels, and something told him he'd be kissing them very soon. In short she was fucking gorgeous, and the smug look on her face told him she knew it.

"Well fag, you're five minutes early and in full drag, good for you girl, but where's your make-up? How can you be a pretty sissy without make-up?"

"I, um, I don't have any Mistress, I've never used any before."

For a moment she looked pissed off, but her face quickly softened.

"Alright Leslie, I'll fix your face today. However, you'd better learn quick because I'm not doing it every day, and my slaves are to keep themselves pretty at all times. Understand fag?"

He nodded.

"Answer me you stupid shit, I thought we covered this yesterday."

"Yes Mistress, I understand, I'm sorry."

She chuckled. "Take a good look in the mirror princess. You're not sorry, you're fucking pathetic."

She took a step back and opened the door.

"Bring your suitcases and follow me Leslie the fag."

As he did his eyes remained glued on her ass the whole time. She led him to a bedroom on the far side of the house. The room had a double bed, night stand, dresser with mirror, a simple arm chair, a closet and a small bathroom. Next to the dresser was a television stand and a small flat screen TV. The accommodations were by no means fancy, but they were comfortable and in good shape.

"You should be very happy here Leslie, now unpack your things. I'll be back in a minute."

When she returned she was carrying a make-up kit. His suitcases were empty and in the back of the closet, which pleased her. He seemed to be accepting his fate easier than she expected. She sat on the bed and ordered him to stand directly in front of her. She looked up momentarily with an annoyed expression, then down at the bulge in his skirt.

"Do you have anything you want to ask me sissyboy?"

He was confused for a moment until he realized what she was looking at, then he suddenly remembered what she told him yesterday about unauthorized boners.

"Mistress, may I please have a boner?"

A small smile appeared on her face.

"Are you sexually excited princess?"

"Yes Mistress, very much."

"Well fag, is it me or my corduroy outfit that's making your little penis hard?"

"It's you Mistress, I'd be horny for you no matter what you were wearing."

Her smile morphed into a smirk. "Somehow I don't believe that for one minute, but it was the right answer, so good for you fag. Now lift your skirt."

She unzipped her make-up case and pulled out a small pair of scissors.

"Hold still sissyboy, unless you want your mistress to make you a real girl."

She pinched his tights just above his ball sack and snipped off a little piece, which expanded into a one inch hole when she let go. Putting the scissors down she used her fingers to tear the hole open just enough to pull out first his boner, and then his sissy balls. She wrapped her fingers around the top of his ball sack leaving his balls in the palm of her hand where she could easily squeeze the shit out of them if she so desired. She then tugged on his balls just enough to get his attention and make it clear who they now belonged to.

"In the future you'll see to it that your sissy penis is always easily accessible. Do you understand princess?"

"Yes Mistress."

She gave his balls a hard yank and he grunted loudly in response.

"I can't hear you sissyboy."

His volume increased. "Yes Mistress I understand, I'll always keep my penis easily available."

"Good girl."

After letting go of his balls she playfully slapped them, which caused him to jump. She found that very amusing. She alternated between gently massaging them and slapping them just hard enough to sting. She definitely knew what she was doing and kept him on pins and needle wondering what coming next, pain or pleasure. She seemed to enjoy what she was doing immensely and kept her eyes on his penis while she spoke.

"Are you going to be a good little cocksucker for me sissyboy?"

"Yes Mistress."

"Do you want to suck cock for me Daisy May?"

"Yes ma'am, I always want to please you in any way I can."

"That's not what I asked faggot."

Her next slap was a little harder and he emitted a sissy squeal.

"Yes Mistress I want to suck cock. I want to worship dicks for your pleasure. I want to be a cock whore for your amusement. Please make me be your cocksucking bitch!"

She gently patted his balls and purred loudly. "Right answer fag, you're a fast learner, I like that."

That was true. Jordan had been a submissive sissy a few times before and it not only came natural to him, he enjoyed being that way. She decided to move on.

"Put down your skirt Leslie, then pull the chair over and sit."

He did, and she spent the next twenty minutes using her cosmetics to give him a pretty face. Upon finishing, she held up a small mirror and he was truly amazed. He'd need another opinion to be sure, but he actually thought he might be passable. Well, from a distance anyway. That excitement him tremendously, and between that and her unexpected pleasant demeanor he relaxed a bit. Seeing that, she zipped her case closed and her smirk returned.

"I'm going to give you a piece of friendly advice, so listen carefully fag. Don't ever relax when you're around me, not even for a minute. I mean it Daisy May, sissies who relax tend to get insolent, and there's nothing I despise more than an insolence bitchboy, just ask naughty Natalie. So if you don't want to find yourself in a world of shit, and maybe even missing your sissy balls, you'd better be trying to please me every fucking minute of every fucking day."

She paused to let her words sink in and appeared amused as she watched the smile slowly fade from his pretty face.

"Are you beginning to see the big picture Leslie Bains?"

Having his balls threatened in such a calm manner caused those threats to be more chilling than if she'd shouted them in anger, and she definitely seemed like a mistress very capable of carrying out those threats.

"Yes Mistress, I am."

And that wasn't bullshit. This woman was different than the previous ones, she was the real deal. She was clearly the most sexually exciting woman he'd ever been with, and she was also by far the most dangerous.

"Alright Leslie the fag, if you really do understand then we'll get along famously. Now it's time for you to start serving your purpose and earning your keep."

She stood up, fussed with her hair a little and straightened her jacket.

"Follow me fag, and make sure you speak only when spoken to."

She walked out of the room without looking back, and he obediently followed. As they entered a large living room his attention was drawn to the person seated in one of the armchairs, there were two positioned at either end of a long sofa. He appeared to be a little older than Leslie, and he was definitely a tinkerbell. Leslie's mind immediately compared himself to the fag and judged himself to be the prettier of the two. When he realized how sissy and petty that was, he was shocked by his own thinking.

The fag wore a Light blue wide-wale corduroy skirt that came just above the knee, and a maroon ribbed knit top that was stretched over a pair of medium sized titties. He guessed the boobies were fake because he didn't appear feminine enough to be a tranny. His long blond hair was full bodied and didn't look like a wig. The make-up was well done and his face was fairly attractive, and but it still had a slightly masculine edge to it. He was a thin fag, definitely taller than Leslie and looked to be about five years older. He sat with his long stocking clad legs crossed like a lady and his arms draped over the arms of the chair. For a tall man he did dainty well. His painted lips were full and inviting, and he had a very cute smile on his face, one that belied the traces of masculinity sitting just below the surface.

Mistress Kate sat in the other armchair and instructed Leslie to sit on the couch. There was a stack of neatly folded corduroy trousers sitting on the end of the sofa nearest his Mistress, so he sat at the other end near the fag. With a cute tinkerbell to his left and a stack of corduroy pants to his right he didn't know where to focus his attention. His skirt began to tent with a new boner and he looked at Mistress Kate hoping to distract himself. However, doing so only made matters worse, because she too was a very sexy sight. Seeing the mixture of confusion and panic on his face she chuckled and lit a cigarette.

"What's the matter Daisy May, are you confused?"

He just stared blankly, having no idea what to say.

"I hope that boner is still the same one from before. I'd hate to have to give your balls a good hard slapping right in front of Natalie."

"Um, yes Mistress, it's the same boner."

They all knew he was lying and he felt humiliated for acting like a dickless wimp. She blew a large plume of smoke at him.

"This is Natalie. He's been one of my clients for about fifteen years. Say hello fag."

Leslie looked to his left, and when they made eye contact Natalie's smile got even sexier.

"Hello Natalie, my name is Leslie."

"So I've been told gorgeous, I hope we're going to get to know each other very intimately, real soon."

He winked, and his voice was dripping with lust.

"That'll be quite enough Natalie."

There was an edge of annoyance in her voice, she sounded like a house mother correcting a salacious teenage girl. Natalie held Leslie's stare a lot longer than he should have before looking at his mistress, and Leslie thought that was rather insolent behavior. Apparently Mistress Kate felt the same way.

"Tell me Natalie dear, did it ever occur to you that being an insolent bitch and being forced to wear a cock cage for two months, might be related?"

Natalie's smile faded and he dropped his eyes to his lap.

She chuckled. "God, sometimes you can be a really stupid little bitchboy Natalie."

She turned her attention back to Leslie.

"You see fag, of all my slaves Natalie requires the most correcting. I've been training him for fifteen years and he still can't help being disobedient. Sometimes I think the little bitch actually enjoys being punished."

Sizing things up quickly, Leslie suspected she was right.

"This stupid bitch still has two weeks to go on a two-month punishment for jerking off without permission. You'd think that after not cumming for six weeks he'd smarten up and behave like a good little slave. However, as you just saw, the horny little shit tries to seduce you right in front of me."

She sighed deeply. "Well anyway, I brought you in here to show him the kinds of rewards that are now available if he starts behaving properly."

Leslie wasn't sure he liked the sound of that.

She gave Natalie a look of disgust. "Are you done being a naughty girl dearie?"

His head was bowed submissively and all his cheekiness had disappeared.