Mistress Kate Pt. 01

"Yes Mistress, I'd be very happy to."

Now that the immediate danger was gone, having the Leprechaun being his bitch was giving him a thrill. An hour ago he thought this guy was going to have him killed, and now he was down on his knees all dressed up in corduroy and sucking his dick. Feeling his hands running around his trousers was getting him horny too. The idea that Regan O'Reilly was getting turned on by his pants was inconceivable, and the thought that he probably wanted to rub his boner against Jordan's corduroys was almost surreal. He had several fantasies about the two of them using corduroy to make each other cum, especially when they were in full drag. Looking at the ponytail running down his back he wondered what he would look like in feminine attire, he obviously wouldn't need a wig. He fantasized about the two of them all dressed up and rubbing their boners against each other's corduroy girly clothes. He liked that idea a lot. However, his lust was interrupted by his new Mistress.

"Are you enjoying yourself Gloria? I think Leslie really wants to cum in your mouth, so be a good girl and suck him off. Hurry it up dear, I have other things to do today."

He was bobbing his head up and down faster and faster, jerking him off with his lips, and Jordan imagined the bitch was loving every minute of it. Kate stood up, then leaned down so her face was within inches of Jordan's, and the closeness of her corduroy covered tits drove him crazy with lust. His eyes immediately locked on her boobies and stayed there far longer than they should. Suddenly realizing his insolence he quickly looked away.

"Hey fag, look at me."

He complied.

"Do my titties turn you on?"

He looked frightened, but nodded.

She chuckled and gave her tit a playful squeeze. "In your dreams wimp."

She then whispered in his ear. "If you don't cum in his mouth in the next five minutes I'll rip your sissy balls off so you never cum again"

She then straightened up, walked over to the desk and lit a cigarette. Fortunately for Jordan Regan was a fast learner, and between his eager mouth and the sight of Mistress Kate in corduroy he felt an orgasm coming on quickly. As it drew closer his first instinct was to call his bitch a fucking cocksucker and several other nasty things, but then he remembered whose mouth was on his dick, and insulting the Leprechaun suddenly seemed like a bad idea. His mouth was doing such an excellent job that his orgasm overtook him and he started moaning loudly. Jordan's boner spasmed between his lips a split second before his mouth filled with jizzum for the very first time. He was now officially a cocksucker, and the realization that a real cock was spitting sperm in his mouth thrilled him to no end, his only regret was that he wasn't dressed in full drag.

However, having his mouth fill so quickly also caught him by surprise. He swallowed hastily and pulled his mouth up so just his mushroom was still in it, but by the time he got there Jordan had already pumped it full again, his mushroom was spitting rapid fire. He did manage to swallow that mouthful too, but being a virgin he panicked a little and pulled his mouth off, that left Jordan's swollen knob staring him right in the face. It then did what any horny dick would do in the middle of an orgasm, it spit out a long stream of thick creamy jizzum that splattered all over Regan's face. His panic increased and he wasn't sure what to do, but he knew he only had two choices. Either pull his face away and ruin the blowjob, or jam his mouth back down and swallow the rest like a good little cocksucker. Not surprisingly he chose door number two, after all he liked being called Gloria for a reason. Jordan emptied his ball sack in his mouth and the bitchboy swallowed every bit of it.

Jordan's eyes were glued on Mistress Kate in her butch corduroy outfit the whole time, and he couldn't help thinking of her as Gemma, the tough bitch from the TV show. She however completely ignored him, keeping her eyes cast upward as she smoked her cigarette. The smirk on her face was a mixture of boredom and amusement, she was simply waiting for her fag slave to finish sucking his first cock. Just before his orgasm tapered off, a picture of her leering at him with a big dildo sticking out through the zipper of her pants flashed in his mind. He really liked that picture. Under normal circumstances right about then he would slip into a contented afterglow, but these were far from normal circumstances.

He wasn't sure what the Leprechaun was going to do to him when he entered the room, but it's safe to say that sucking his dick wasn't one of the possibilities Jordan considered. Yet there he was with Jordan's limp dick in his mouth and his sperm splattered all over his face. Jordan couldn't let himself relax however, because even though he loved having his dick sucked by a virgin dressed in corduroy, he couldn't be sure that Regan wouldn't suddenly have regrets, and who the hell knows what would happened then.

Regan didn't help things either. Without giving Jordan a smile or any indication that he enjoyed himself, he suddenly pulled his mouth of his dick and spun around on his knees to face Mistress Kate. She looked down at him with a smiled and chuckled.

"I like what I see Gloria, not only are you officially a cocksucker, but you've got jizzum splattered all over your sissy face. What a pathetic wimp you are. I love it!"

She crushed out her cigarette and pointed to the floor in front of her.

"Get over here bitchboy, right now!"

He did so obediently.

She gave him a dirty look and shook her head in disgust, then reached over and yanked his ponytail, forcing him to look up at her. Using two fingers she scooped up a big glob of sperm and held it in front of his lips.

"Open your mouth Gloria, now that you're my newest little cocksucker you need to learn the rules. Rule number one, my bitches never waste sperm."

She shoved her fingers in his mouth and he obediently licked them clean. As she continued to feed Gloria his jizzum, she humiliated him for being a cocksucking sissyboy and he didn't protest. Seeing that, Jordan felt relieved. He guessed Regan wouldn't be having any regrets today, and that allowed him to relax a little. However, after a minute Kate must have decided he looked a little too relaxed.

"I hope you're not trying to impress me with that little pecker Daisy May, because it's nothing to be proud of. You better zip it up right now before I give your sissy balls a good hard slapping."

Her sudden nastiness caught him by surprise, but even though the insult to his masculinity was like a slap in the face, it also excited him a little. It'd been a while since he had a Mistress talk to him like that. Not wanting to piss her off, he lowered his eyes, stuck his dick in his pants and zipped them up. Satisfied with his obedience she turned her attention back to Gloria and fed him the last of the sperm.

"You've been a good sissyboy today Gloria, would you like a reward? Would you like me to make the fag suck your dickie?"

He said something to her and shook his head, but with his back to Jordan he couldn't make out what it was. She smiled, then patted his head like a puppy.

"Alright Gloria I understand, you want him all girlied up before we go any further, that certainly sounds reasonable, and since you've been a good little cocksucker I'll allow it. In a few minutes you'll be permitted to go back in the bedroom while I finish up with the fag. I left my blue corduroy skirt on the bed and you may jerk off with it if you'd like, but first I want you to stand up."

He obeyed her and she kissed him on the forehead.

"Alright Gloria take a few steps back and bend over."

Again he obeyed her command, and that left his corduroy covered ass right in front of Jordan's face.

"Kiss his ass Leslie. Kiss it all over and thank me for making him suck your pathetic little penis. I want to see you display proper gratitude to your mistress."

Jordan was shocked, however he found her ability to dish out humiliation in such a casual manner very exciting, it seemed second nature to her. In addition, something about having a corduroy covered ass just inches from his face turned him on like crazy. Not wanting to anger his new mistress, he immediately pressed his face into Regan's bottom and the feeling of the corduroy was fantastic. He grabbed his hips with both hands, started kissing all around the seat of his pants and the reality of what he was doing sank in. He was literally kissing another man's ass, it was probably the most humiliating thing he'd ever done. As he thanked her for making Regan suck his dick, he imagined she'd be taking him to far more humiliating places in the future, and even though he wasn't sure where things were going, he liked the idea of that. She let him continue for several minutes then decided she'd heard enough.

"That's enough Leslie. God, what a pathetic sissy wimp you are, sitting there kissing another guy's ass like a fucking queer. Maybe I should order Regan to pull down his pants so you can stick your tongue up his shitter. Would you like that Daisy May pantyboy?"

"Yes Mistress, very much."

She chuckled. "I'm sure you would dear, however I was talking to Leslie. Well fag, would you like to be a turd licker for your Mistress?"

He froze, and with his face still pressed into Regan's ass he thought, well that certainly didn't take long. His first instinct was to say no, maybe if it was her ass he might consider it, but he had no desire to do anything that gross with a man. Although he had to admit, the humiliation was exciting, but the reality of the act wasn't appealing. During his lifetime he'd been with a few dominant women and enjoyed their threats. But when it came to having men involved in their games, other than making him suck a few dicks or occasionally take one in the ass, their threats to do anything else were just that, threats, and nothing more. This woman however, didn't seem like the kind of lady who wasted her time with idle threats, no, he sensed she was very different. In addition, with all the dangers involved in his situation he decided being obedient to her was his best bet, he'd be her sissy bitch and hope for the best. It's not like there were a lot of choices available anyway. He continued to kiss Regan's bottom.

"Yes Mistress, I want to serve you, may I please suck Regan's dick for you?"

He threw that in to try and change the subject. Although, with Regan in his corduroy pants he really would have enjoyed doing it.

"Are you trying to get on my good side you little ass kissing queer, all the sudden you want to be my bitch's cocksucker now?"

She chuckled. "I must admit Leslie it was a nice try, however my Gloria wants you in a pretty dress before you suck his dickie, he wants to play sissy games before he squirts in your mouth."

Jordan felt the same way, although he decided it wasn't a good time to point that out.

"I just want to please you Mistress Kate."

She slid her hand between her legs for no particular reason, then slowly started rubbing her crotch.

"Alright Gloria you can go, go have fun with my skirt. Just remember dear, I'll snip your little nuts off if you cum without permission."

He stepped forward removing his ass from Jordan's face, then without looking back he left through the doorway behind his desk, closing the door behind him. As Jordan watched the corduroy ass he'd just been kissing walk out of the room he couldn't believe it belonged to Regan O'Reilly, that reality was still mind-boggling.

When she heard the door close behind her she sat up on the desk and spread her legs. She looked down and rubbed both hands all around the front of her corduroys in a very suggestive manner. That sight excited him tremendously. After ignoring him for a minute or so she looked his way, and her face was a mixture of desire, amusement and pure bitchiness.

"Don't worry newbie you'll be sucking Gloria's dick tomorrow, and every day after that for a long time to come, along with a few other dicks."

Jordan gave her a strange look, and she found that amusing.

"What's puzzling you Mary Jane? Do you still not understand why you're here?"

He began to say something but then thought better of it.

"May I speak Mistress?"

"Yeah fag, go ahead."

"I thought he wanted me to be Gloria's sissy playmate, to suck his dick until I paid off my debt, so why are you talking about other guy's dicks?"

"Did you think I was kidding before? I said you'd be sucking the dicks of my sissy slaves."

"I thought you meant Gloria."

"I said slaves with an S sissyboy, that's plural, Gloria is not my only slave."

"But he's the only one I owe money to."

She laughed out loud.

"You really don't have a fucking clue, do you princess? Although you'll be used for that purpose, you're not here to be Regan's bitch, you're here to be my full time sissy slave until you pay off your debt. He's using your debt to give his Mistress a gift, you're his present to me sissyboy. I'm sure he's hoping that the happier you make me the more rewards I'll give him in return, especially corduroy rewards. You see Leslie the fag, until further notice his happiness depends entirely on how much I like your behavior. If you're a good pussy licker for me, and a good little cock whore for my clients, I'll make Gloria a happy little sissy. Now think Leslie dear, do I need to spell out what he'll do if you don't make me happy?

He exhaled loudly. "No Mistress, I just thought. Never mind Mistress, I'm sorry."

He'd finally accepted his fate, he had no other options, it was either this or the hospital, or worse.

"Much better dear. Just be very obedient for me and your sissy little balls will have nothing to worry about. Do you understand your position a little better now Leslie the fag?"

He nodded.

"Good, I'll explain a lot more tomorrow when you start your training. You are to report to my house tomorrow morning at ten, and I want you in full drag princess, so pick out something pretty to wear. Also, I want you to bring all your clothes, you'll be living at my place until further notice."

She lit a cigarette.

"Oh, I almost forgot. Tonight you'll receive a delivery, the package will contain a satchel with a lot of money in it, $100,000. You're to bring it with you to the office tomorrow at eight o'clock before coming to my house. When you get here Regan's boys won't let you in without looking in the satchel, and that's OK, that's what we want. We want them to think you're making a big payment, it will explain why they weren't required to hurt you. So first you are to come here and give Regan the bag, then go home, get dressed and report to my house without being late. I despise tardiness sissyboy. Do you understand what I expect from you tomorrow?"

He nodded.

"Answer me fag, this is fucking important, and you'd better do it right."

"Yes Mistress, I understand what you want, and I will do as instructed."

She smirked and gave him a long, hard stare, she seemed to be deciding whether she believed him or not.

"Alright sissyboy you'd damn well better if you know what's good for your sorry ass."

She slowly slid off the desk then walked over and sat in the armchair, keeping her bottom right on the edge of the seat. Snapping her fingers she pointed to the floor in front of her.

"Come over here Leslie."

He did so quickly, kneeling between her legs, and the close proximity of her corduroy outfit made his cock begin to harden. Seeing the sudden look of lust on his face she chuckled.

"Do you like my pants pervert, are my corduroys making your little dickie hard?"

He kept his eyes glued on her trousers and nodded.

"Get your face in my crotch and give my pussy a good sniff."

She roughly grabbed the back of his head and pushed his face between her legs, which caused him to grab her thighs for balance. He wondered if that would piss her off but when she didn't react negatively he relaxed a little and enjoyed the feeling of her trousers, they felt wonderful. Deciding to let the new bitch explore her pants for a little while, she sat back in the chair and relaxed. The fabric was on the wide side of mid-wale, almost a wide-wale, and the ribs were firm with a soft finish. It felt like a perfect mid-wale corduroy to Jordan, firm but soft, the same way he liked his mistresses, rough but with soft edges.

She reached over, grabbed a pack of cigarettes and lit one, then tossed the pack back on the table. Her face looked preoccupied and bored, she looked as though she was making up her mind about something trivial. As he kissed her crotch his eyes raped her corduroy outfit, and the sight made him very horny. Her face was sitting just above her large corduroy covered tits, and he decided to study it for a few minutes. She wasn't a young woman and although her face was pretty, it was also somewhat hard-bitten. He guessed she was in her mid-forties, maybe even a little older, but he didn't mind that as he preferred older women, he thought they were far sexier than young bimbos with no brains. She'd gone a little heavy on the make-up and he wondered if that was a compensation for her age, but whatever her reason, it added an air of sluttiness that he found exciting.

She was an attractive tough bitch, a well-practiced mistress, and even though he was in an insane situation he wanted to be owned by her. His eyes then focused on her tits, and the thought of burying his face in those corduroy mounds made him crazy with lust. After a few more minutes they zeroed in on the fly of her pants right in front of his face, and he dreamed about a huge dildo sticking out through the zipper, one he knew she was going to shove up his ass with great enthusiasm. Suddenly all the dangers involved in his Leprechaun predicament disappeared, and all that remained was the sight of this very sexy woman. And even though he knew the idea was crazy, spending a couple of years dressed in full drag and being her sissy slave seemed like something he really wanted to do. His thoughts were cut short however when she sent a large plume of smoke toward the ceiling and spoke.

"By the way asshole, just in case you're thinking about taking the money and running, don't do it. You'll be found and you'll be killed, it's that simple, nobody ever gets away with shit like that. You seem nice enough for a wimp, and I think you'll be a good little sissy slave, so don't you dare ruin my plans."

She took another drag.

"Tell me fag, are you a good pussy licker?"

He thought he was, he'd received many compliments from the ladies. He removed his mouth from her crotch.

"Yes Mistress, I like to think so, would you like me to lick your pussy?"

His enthusiasm impressed her.

"Actually sissyboy I'd like that a lot, but I think I'll make Gloria do it instead. I'm going to humiliate him for sucking his first dick and I want him licking my cunt when I do it. Don't worry princess you'll get your chance tomorrow, and for your sake fag, I hope your tongue is well skilled."

She stared at the ceiling as she finished her cigarette and he continued kissing her pants for another ten minutes.

"Alright fag, that's enough corduroy fun for now, do you have a boner?"

The question caught him a little off guard and he leaned back, sitting on his heels.

"Um, yes Mistress I do."

She sat up straight in the chair. "Stand up."

When he did, she rubbed his corduroy bulge and smiled.

"Well good for you princess. You better have a boner whenever you're with me, if you don't I'll take it as a personal insult, you should always be horny for your mistress. But then again, being a worthless turd you aren't allowed to have any boners without my permission. Did I give you permission for this boner sissyboy?