Mistress Kate Pt. 01

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all the stories. Regan O'Reilly, AKA: The Leprechaun, controlled all the gambling and prostitution in Waller City, a busy metropolis in the south east. When sober, Jordan was a fairly good poker player and he'd won good money at O'Reilly's tables over the past few years. The Leprechaun ran a clean operation and didn't bother the serious players provided they didn't win too much too often. He didn't need to, the odds were on his side. However, if you got caught cheating, were suspected of counting or borrowed money you couldn't repay, then you got to meet the Leprechaun, or some of his "associates".

Jordan never tried to cheat, he wasn't that stupid, but the week before he committed the third sin, he borrowed money, a lot of it. Over the past few months his drinking had steadily increased and he started playing drunk, which made him a disaster waiting to happen. All was well for a while, but then the worst thing that could happen to a drunk happened last Wednesday night, he started winning really big. He was doing so well in fact that he moved to the high-end tables where the buy in was $10,000, and that's when everything turned to shit. After briefly winning big he started losing, and borrowing. That continued until the bottom fell out. Based on the money Jordan brought to the table the pit boss allowed him to borrow a lot more than he should, a mistake for which Jordan guessed the guy paid dearly.

$186,500.

That was the damage before they finally cut him off and Jordan had about $20,000 in his dresser drawer. Being known to them, they allowed him to go home on a promise he would have the cash within a week. That was seven days ago. He wasn't sure why, perhaps because of the large amount of money involved, but O'Reilly didn't have his associates take care of business when they came calling. Instead he instructed them to bring Jordan to his office, a development that relieved Jordan greatly, however it also left him confused and fearful.

When he entered the room someone closed the door behind him, and he found himself staring into the Leprechaun's eyes. He wasn't anything like what Jordan had envisioned. He'd been expecting to find a burly, red faced Irishman sitting behind the desk, a big ugly guy with a short temper. However, the young man seated in front of him didn't look intimidating at all. He was slim, looked to be in his mid-twenties and although he was sitting Jordan guessed he was about 5'10" tall, maybe shorter. He was wearing a white t-shirt under a grey corduroy jeans jacket, again not what Jordan would have expected. His long red hair was tied back in a ponytail and he had no facial hair. Quite frankly, he looked like a kid. Jordan wasn't stupid enough to let that lull him into a false sense of security, he knew the danger wasn't in the kid, it was in the big bad people the kid paid handsomely. He saw the nameplate on the desk that said Regan O'Reilly, and he wondered if that was really necessary.

There was a wooden chair positioned in front of the desk and Regan told him to sit. As he did a woman entered through a door in the rear of the office and sat in an armchair off to the side. She was a tall attractive woman wearing a tan corduroy shirt tucked into a pair of dark brown mid-wale corduroy jeans. Her resemblance to the character Gemma on the show Sons of Anarchy was striking.

"I take it you don't have the money. Am I right?"

He quickly returned his attention to O'Reilly, then looked down and shook his head.

"Well Jordan, what are you planning to do about this unacceptable situation?"

Jordan knew he was fucked.

"Mr. O'Reilly, I know I'm in deep shit and I don't want to insult you by making promises I can't keep. But as you probably know I've been playing around here for a while, and, and I'm pretty good. So maybe if you, I know I don't deserve it, but maybe if you'd give me some time, I could pay you off."

Regan looked over at the woman and chuckled.

"So if I understand you correctly, you want to use my tables to pay me back with my own money. Is that about right Jordan?"

He immediately realized how stupid it was and looked down in defeat. Reagan leaned forward and spoke in a matter of fact, almost pleasant tone.

"Under normal circumstances when someone comes to me in your position Jordan, one of two things happen. If I don't like the individual or don't see a way to recoup my losses, well then, things don't end well for them. On the other hand, if the individual is of some value I have my associates see to it that they spend a little time in the hospital instead. That gives them a chance to make good in the future and sends a message to all the other players."

Jordan wasn't happy about what he was hearing but he'd been expecting it, in fact, he didn't understand why it hadn't happened already. He dropped his head and shut his eyes tightly.

"I'm sorry Mr. O'Reilly, I'll do anything, please let me fix it."

There was a long pause before O'Reilly spoke. "Well, what do you think Miss Katie?"

Jordan dared a peak, Regan was looking at the woman.

She sighed deeply. "I guess he's worth taking a chance on Regan."

"Should I go on?"

She sat up and crossed her long legs, then lit a cigarette and opened a manila folder in her lap.

"No, I'll take over from here you little wimp, just sit back and shut up."

Jordan wasn't sure he heard her right, but it appeared he did when Regan obediently sat back and lowered his eyes. She kept her eyes in the folder.

"Let's see. L. Jordan Bains. The L stands for Leslie doesn't it?"

He nodded.

"Answer me asshole, that's the way this works, I ask a question and you give me a fucking answer. Got it Mary Jane?

The sharpness of her voice shocked him. "Um, yes Ma'am, my name is Leslie, but I prefer Jordan."

"I don't give a fuck what you prefer. Leslie is a girly name and right now you're not much of a man, so I think it fits pretty good."

She took a drag and kept reading. Jordan had no idea what was going on.

"It says here you're a fucking faggot, you like to dress in women's clothes and act like a girl. Is that true Leslie?"

He was devastated by the question, mostly because it was true. He hesitated, but when she looked straight at him he immediately knew she was no one to fuck with.

"Yes Ma'am, that's true."

"I know it's true Leslie, because I know everything about you. You're a prancing Nancy with a corduroy fetish, corduroy makes your little dickie hard. Is that why you're wearing those pants?"

He had on a pair of corduroy trousers but at that moment he was far from turned on, he was confused and scared.

"Um, yes Ma'am, but how..."

"And according to your ex-wife, when you're dressed girly you're a submissive sissy who loves sucking cock. Is that also true Leslie the fag?"

He stared blankly with his mouth hanging open, not knowing what to say.

"That's right Leslie, your ex-wife hasn't been having much luck at the tables either. When she was offered a clean slate she was more than happy to give up all your little secrets. I know all about your Tumblr account too."

She motioned to Regan and he turned his computer monitor around.

"And after a friend of mine figured out your password I learned a whole lot more. I saw all the pictures of fags and trannies having sex, and the dominant women too, along with all those pictures of cocks sticking out of corduroy pants. You really like that, don't you sissyboy?"

He shut his mouth, swallowed hard and nodded.

"You see Leslie, I've done my homework and I know everything about you. Actually fag you should be glad I did, because it's the only reason you're still sitting here in one piece."

She put out her cigarette, then took a deep breath and spoke very matter of factly.

"OK Leslie the fag, this is your situation. My name is Mistress Kate, and you have two choices. You can either go to work for me starting immediately, or you can resume your conversation with Regan."

He made eye contact as he thought. She was an attractive woman and really did look a lot like Gemma. She appeared to be in her mid-forties and her long brown hair had blond highlights. Her corduroy shirt was filled out nicely with a large pair of tits and the top three buttons were undone exposing ample cleavage. She was not a petite woman. He guessed she was about 6' tall and 150 pounds, pretty much the same size as him, and she sounded a lot like a woman who didn't take shit from anybody. He cleared his throat.

"What kind of work are you talking about Ma'am?"

She chuckled. "Does it really matter at this point asshole?"

There was a snotty smile on her stone face and he wasn't sure if he should maintain eye contact.

"You'll be my full time sissified cocksucker in a dress. You'll be my slave 24/7, and when you're not servicing my pussy you'll be sucking the dicks of my sissy slaves."

She stood up, slowly walked over and her heels sounded ominous on the wood floor. She got right in his face, so close in fact that he had to sit back. She leaned forward putting her arms passed him and grabbed the back of the chair. Looming over him with her big tits, she was both intimidating and very sexy.

"Do you like my corduroy outfit fag?"

He ogled her tits and slowly nodded.

"Answer me asshole."

"Yes Ma'am, your outfit is very sexy."

"I bet you'd love to rub your pathetic little dickie against my pants, wouldn't you sissyboy?"

He hesitated, then looked up at her face. "Yes Ma'am."

"Oh I bet you would, you fucking pervert."

He couldn't believe what was happening. A moment ago he thought he'd get the worst beating of his life, and now this.

"Alright Leslie, this is how it's going to work. You'll be paid a thousand dollars a week which will be applied directly to your debt, Regan will even let you slide on the vig. In return you'll be my full-time maid. You'll always be in drag and you'll keep my house spotless. You'll also be used as a training tool for Gloria, my newest sissy slave. Until now he's been a cock virgin, but I'm about to make him worship his first dick. He also has a corduroy fetish and that's the reason I chose you."

Jordan remained mute, staring in disbelief.

"I've decided it's time for my sissyboy to become a real fag, it's time for him to worship a cock, and you're going to help me with that Daisy May. He's never even touched a penis before, so I'm going to start him off with a sissy dick. Your dick Leslie. I'm guessing that with the both of you in corduroy drag and making each other horny, my bitch will be begging me for your dick in no time at all. Isn't that right Gloria?"

Jordan was confused, until he heard a very meek voice behind her. "Yes Miss Katie."

She and Jordan held their stare, and when she saw the realization on his face she smiled.

"That's right Leslie the fag, my newest sissyboy is none other than Regan. The all-powerful Leprechaun is my bitch. Isn't that right Gloria?"

"Yes Misstress, you are right as always."

"So keep that in mind you fucking wimp, the most dangerous man in Waller City answers to me, he's my bitch. So what do you think that makes me?"

"A very dangerous woman."

"Mistress you little shit, a very dangerous Mistress."

"Yes Ma'am, I meant Mistress."

She slowly stepped back a few feet without breaking eye contact and maintained her sneering smile. She then snapped her fingers and pointed at the floor next to her.

"Get over here Gloria."

He came around his desk quickly and knelt down in front of her, never looking at Jordan. His face was red as a beet and it seemed obvious he was extremely embarrassed. Jordan noticed he was wearing a pair of gray mid-wale corduroy jeans that matched his jacket, they hugged his ass nicely and the fabric looked plush and expensive. Seeing Regan on his knees made Jordan relax a little, and now that the immediate danger was gone their corduroy outfits started giving him a boner. Once in place she ordered him to kiss her boot, which Regan did obediently. Returning her attention to Jordan she was amused by the shock on his face.

"That's right fag, the Leprechaun kisses my feet, and you're the only one who knows. Do I need to spell out what would happen to you if you ever opened your mouth?"

The look on her face was pure hard core bitchiness, it screamed, "don't fuck with me asshole."

"No ma'am, I think I get it."

"Mistress, asshole, from now on you call me Mistress."

"Yes Mistress, I'm sorry."

She ordered Gloria to straighten up then stepped forward. She grabbed the back of his head and shoved his face into her crotch and he immediately started kissing it.

"Guess what Gloria, I think Leslie likes your corduroy butt, I think he wants to fuck it. Do you want your sissy ass fucked bitch?

He mumbled something into her crotch but Jordan couldn't make it out. She asked him several more questions designed to humiliate him and Regan endured without protest. Jordan was confuse. Obviously he was relieved by his reprieve, but he still wondered where all this was leading. She turned her attention back to him.

"You see fag, Regan pays me a great deal of money to be his Mistress. Yes, the little bitch really needs his discreet tormenting queen. Isn't that right Gloria dear?"

He gave a muffled affirmative into her crotch.

"And because of that I've dropped most of my clients, I'm now semi-retired. However, I did keep a handful of my well-paying clients. They're all submissive sissy fags just like you, but because of Regan's notoriety I can't use any of them for his cock training. I'm not sure why but when Regan told me you owed him all that money I decided to check you out, and the more I learned the more you sounded ideal for the job."

She lit another cigarette.

"Well, in truth, the corduroy thing is what put you over the top. So I told Gloria I wanted to see you in person and decide whether I wanted to take a chance on you or not."

Gloria kept kissing around the front of her pants like a horny bitch and she gave Leslie a long stare, eyeing him up and down with a smirk. The more he saw that look the more he got the feeling it wasn't contrived, it seemed to be her natural expression. Somewhere between disgusted and amused.

"Alright fag sit up straight, spread your legs and make room for my bitch."

Her voice left no room for rebuttal and he did as told.

"Go get between the fag's legs Gloria."

He looked up and hesitated.

"Did you suddenly go deaf bitch? Move it."

He turned around and positioned himself on his knees between Jordan's legs. He kept his face lowered and his eyes glued on the bulge in Jordan's pants, he apparently had no intentions of looking at Jordan's face.

"You know what Leslie? You're a lucky fag. The big bad Leprechaun's about to suck your dick. He doesn't look so tough now, does he sissyboy?"

Regan shut his eyes tightly and took a deep breath, her humiliation had obviously hit its mark. Not sure how to answer and not wanting to antagonize him, Jordan just gave her a very confused look.

She chuckled. "That's right Leslie, you, a pathetic little crossdressing sissyboy, are going to squirt your jizzum in the Leprechaun's mouth. Think about that Gloria. God, what a fucking wimp you are."

She laughed. "Go ahead bitch, kiss his bulge, you know you want it, you've been wanting to suck cock for months. Kiss his corduroys and think about what's waiting for you in those pants."

Regan slowly opened his eyes and they immediately focused on Jordan's bulge. There was still a look of embarrassment on his face but his eyes were now full of lust. He put his hands on Jordan's thighs and the feeling of the corduroy made him inhale sharply, then a look of surrender came over him and he lowered his face, kissing his corduroy covered prize. That only lasted for a minute or so before he started rubbing his face all around the front of Jordan's pants. The more he did that the more turned on he got and his lips kept returning to Jordan's bulge, it was pretty obvious he wanted to do more than kiss his trousers. Apparently the corduroy had broken down any resistance he had left, and Jordan could certainly understand that.

In the midst of all his fear and confusion, the fact that he had just met another guy with a corduroy fetish had gotten lost. Jordan had never met another corduroy lover before, and that idea began to excite him. After a few minutes it became obvious Regan had lost all reservations and was thoroughly enjoying himself. In fact, at one point his moaning got pretty loud and Mistress Kate seemed to take that as a cue. She walked over and crouched down beside Jordan so her face was near Reagan's.

"Are you enjoying yourself Gloria dear?"

"Uh-huh."

"Oh I knew you would, I knew as soon as you started rubbing your face in the fag's pants you wouldn't be able to stop yourself. You're such a perverted little shit, I ought to fuck you with a strap on right now."

She paused for his reaction but he just kept kissing.

"Well it's time sissyboy, pick your face up, right now."

He did, keeping his eyes glued on Jordan's bulge. She Looked at Jordan with a stone face.

"Pull it out through the zipper sissyboy, my bitch wants to suck your dick when it's sticking out of your corduroys."

That's exactly how Jordan liked to suck cock too, and hearing those words turned him on like crazy. He obeyed, and a moment later his very hard seven inch dick was free of its cage. She grabbed his boner and stuck it right in Gloria's face.

"Kiss it fag, kiss another guy's dick, that's what sissy cocksuckers do."

He just stared at it for a brief moment, then suddenly blinked several times and obediently kissed his mushroom. She teased him unmercifully for several minutes, making him lick it all over while telling him he was about to become a sissy cocksucker. Her humiliation was very skillful and Jordan soon found himself getting jealous, he wished he could be her sissy bitch instead. She even slapped Regan's face with his boner a few times and made it very clear he better be a good little cocksucker for his Mistress. She soon decided he was ready.

"That's enough playtime Gloria, now suck his dick. Make another man cum in your sissy mouth."

He obeyed without protest, quickly wrapping his lips around Jordan's mushroom and sliding his mouth half way down his boner. His desire to suck dick was obviously, probably from years of fantasizing about it. He started slowly, tentatively running his lips up and down Jordan's shaft, he seemed to be savoring the fact that he finally had a cock in his mouth. Jordan sighed deeply. Despite the insane situation he found himself in, Regan's mouth felt wonderful.

"Are you enjoying yourself sissyboy?"

They both mumbled. "Uh-huh."

She chuckled. "I was talking to Leslie, Gloria. He's the sissyboy, you're the cocksucker. Does my bitch's mouth feel good on your penis Leslie?"

The sight of her in her corduroy outfit was turning him on even more than Gloria's mouth.

"Yes Mistress, it feels very good."

"Tell me Leslie the fag, would you like to suck a dick too? Do you want to be one of my obedient little cocksuckers?"

"Yes Mistress, very much."

"Right answer bitchboy, and don't you worry princess, you'll be one very soon."

She reached out and patted Gloria's ass.

"However, right now it's Gloria's virgin mouth that's going to get pumped full of jizzum. Would you like to take my bitch's mouth cherry? Are you going to be a good sissyboy and cum in his mouth for me dear?"