Casey's Submissive Journey Pt. 13

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out.

Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again."

She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?"

She chuckled. "Sorry sissyboy, you're just a cocksucker, you should know that by now."

She then returned her attention to the other guy.

Maxi's humiliation wasn't really necessary, Debbie did indeed understand why he was there. His confusion was brought on by Susan's affectionate overtures, that's all. As he sat there reviewing the blow job in his mind and savoring the taste of Susan's sperm, he eyed the guy in the corduroy outfit. He was wearing a pair of baggy pleated dress trousers. They were rust colored and the fabric was a thick wide-wale that looked very soft. His shirt was brown and also wide-wale, and his sports jacket matched his pants in color and fabric. He wore brown shoes and an orange corduroy driving cap. Debbie Knew he'd seen that outfit before, or at least something very similar, and it took a few minutes before he remembered where.

In the past he'd downloaded videos made by guys who shared his love of corduroy. There were some out there, many more than he expected, but almost all of them were queer and that wasn't his thing. However, sometimes they made videos of themselves jerking off while wearing corduroy, and most of them were pretty good. He especially loved the ones where they came on their corduroy clothes, mostly on a pair of pants. He liked to jerk off and fantasize about licking it all up.

In one particular video, a guy dressed just like this one had his dick sticking out through the zipper of his pants and jerked off for a while. After about ten minutes he held his cap out in front and shot a load of thick creamy white jizzum all over it. Then he held the sperm coated cap in front of the camera for a close look, and that always made Debbie's mouth water and his dick as hard as a rock.

Thinking about the video and staring at a guy dressed in the same outfit made him so horny that his boner turned his skirt into a circus tent. The odds of running into a guy dressed like that must have been astronomical.

And then it hit him.

Karen. Karen had seen him jerk off to the video many times, she knew how much he liked watching the guy squirt and she must have set it up with Maxi's help. That excited him tremendously, mainly for two reasons:

It meant that in the midst of humiliating him by making him be a traveling homo whore for her, she was rewarding him by making one of his fantasies come true. So underneath it all she was really a benevolent Mistress.

It also meant he'd get to lick up at least one load of jizzum from this guy's corduroy outfit, and that brightened his whole outlook.

When there was a pause in their conversation Maxi looked over at Debbie, and noticing his tented skirt she shook her head in amusement. She pointed to the floor in front of them.

"Come over here princess."

Debbie got up and quickly did as told. Being on display he didn't know what to do with his hands and his skirt had no pockets, so he nervously folded his arms behind his back. Unfortunately, that caused his boner to tent his skirt even more, and he looked just like what he was, a ridiculous fag. The young guy stared at his skirt and looked unsure of how to react, but Maxi certainly had no problem expressing herself, she laughed and pointed at his dick.

"As you can see Robin, he's every bit as pathetic as I told you, and being twice your age I'm sure you'll enjoy having an older guy as your bitch."

He said nothing but gave Debbie a leering once over, and getting a good look at his face for the first time Debbie could easily believe he was half his age.

Adopting a more formal tone, she continued. "Robin this is your sissy bitch for the day, his name is Debbie. Debbie this is Robin, he's our newest fag, and the youngest we've ever admitted into the club. He and his wife are both nineteen, and we'll be welcoming Mistress Wynonna to the club at our next meeting. Since Susan no longer dresses like a man, she'll be unable to help with your wife's video project. So instead, Wynonna has been kind enough to lend me her fag for the day. Karen picked out his outfit and we'll be making videos of you being a whore for Robin while he's dressed in his man clothes."

"Out of all the fags in the club, I picked Robin for two reasons. Since he's new, I wanted him to have a bitch for a day before he spends the next few months being one himself. In addition, he's a very horny young man, Wynonna tells me he can cum five or six times a day. And Debbie dear, I intend to see that he cums at least that many times today. You're going to provide Karen with a lot of video to watch. Do you understand princess?"

"Yes Mistress, I do."

"Good. Now pull up your skirt."

He did, causing Maxi to chuckle and shake her head.

"How utterly pathetic, although it's about what I expected. I was just explaining to Robin that his nine-inch penis didn't measure up to my minimum standard of ten, so I really don't consider him to be a man. However, being close, I might consider treating him like a man if no other real men were around. But you fag, well I'm guessing maybe seven inches tops. To be blunt Debbie dear, you are completely useless to a woman. You should have your balls cut off and serve as a eunuch."

She paused to sip of her tea.

"I love all the ladies in my club, I really do, but for the life of me I can't understand how they can go through life being fucked by little dick sissies. I mean being fucked with a dildo would be better than having sex with that puny thing. Your wife really needs to be fucked by a real man Debbie."

"But I digress."

She cleared her throat, and said to Robin. "Are the cameras set up and running?"

"Yes Mistress Maxi, everything is ready."

"Alright fag, get on your knees in front of Robin, it's time for you to suck man cock."

Robin sat up straight and spread his legs, and Debbie did as instructed. He laid his hands on Robin's thighs and the soft wide-wale fabric felt wonderful. He looked up at his lap and the baggy corduroy pants were tenting in a major way, making two things very obvious. He wasn't wearing any underwear, and he was very horny.

"Karen tells me you like to kiss a man's corduroys for a while before you suck his dick. Is that true Debbie?"

He spoke without removing his eyes from Robin's bulge. "Yes Mistress I do, may I please kiss Robin's pants?"

She chuckled. "You really are a pervert, aren't you? Alright princess, you can start at his knees and work your way up."

He liked that.

Leaning forward he brought his lips to the inside of Robin's right thigh and kissed a bit. Then falling prey to his lust he pushed his face in and rubbed it all around. He did the same to his other thigh. He slowly worked his face up his legs until he was kissing Robin's corduroy covered balls. He was now horny as hell, and even though he just swallowed a big load of jizzum a few minutes ago, he wanted another. He pressed his face into the bulging lap of the dress pants and rubbed it all around, kissing and nibbling on the hardness underneath while his hands roamed freely around his hips and belly. Maxi could see he was getting himself worked up into a cocksucking frenzy and seized the moment.

"Beg to suck his dick fag, I want to hear you plead with your Mistress to suck another man's cock. Go ahead princess, do it!" He was about to do it anyway, but he always enjoyed being ordered to do things he loved doing.

"Mistress Maxine may I please suck Robin's dick? I want very much to be his cock whore. Please allow me to show you what a good cocksucker I am, I want you to be happy with me. I love sucking dick and you know I was meant to be a bitch for other men's cocks so please use me, use me to please your friends and lovers."

He continued for another five minutes, completely debasing himself and molesting Robin's pants and shirt. He was working himself into a genuine cocksucking frenzy. Maxi was somewhat surprised by how much of a dick slut Debbie was, and she was rarely surprised by anything. As he kissed and begged he briefly looked up, and seeing the corduroy cap he thought about the guy in the video pumping his load all over his hat. He really wanted to see something like that in person, he really wanted to lick up that jizzum for real. Although, as he thought about it, watching him cum all over his trousers would be a lot better. But Debbie knew none of that would be happening anytime soon. Besides, Robin's pants and shirt had him so horny to suck cock that he really didn't want to stop what he was doing anyway.

Finally, Maxi said. "Oh alright fag, shut up and suck his dick before you start crying, God, what a pathetic wimp you are."

Debbie gave his corduroy covered knob one last kiss, then slowly unzipped his trousers and pulled out his hard young boner. It was a beautiful cock, nine inches long with a perfectly shaped mushroom. It was a little on the slim side but that made the crown of his mushroom more pronounced, and Debbie guessed it would feel wonderful being popped in and out of his asshole. There were a couple drops of pre-cum oozing out of his pee-hole and they looked very thick and creamy. He hoped that was a sign of things to come.

He stuck his tongue out and licked them up, then succumbed to his horniness and gobbled his mushroom into his mouth. Robin gave a little moan in response and Debbie sensed he would be cumming quickly. With a cock as long as Robin's, he usually wouldn't be able to rub his face in a guy's pants while sucking him, but with his trousers being very baggy they puffed up to meet his face, and he liked that a lot. Sensing they both wanted Robin to cum quickly, he passed on the idea of teasing and went straight into cocksucking mode. As his face rapidly bobbed up and down in his lap he could hear Maxi talking to Robin.

"Oh I bet that feels good sissyboy, Karen's fag appears to be a very good cocksucker. Tell me young Robin, do you like having an older sissy bitch sucking your cock?"

Maxi's humiliation, Robin's cock, all the corduroy, the image of Susan's huge boner, everything was making him crazy with lust, and his lips were jerking Robin's boner off as fast as any hand could. Then, just like that, without any warning, Robin grunted loudly and pumped his mouth full of sperm. Debbie swallowed quickly, but unlike Susan his young horny dick squirted its streams very rapidly, and he came a ton. Debbie tried to stay with it but it was a lost cause, twice the jizzum gushed out the sides of his mouth and splattered all over the front of his pants. He did his best to swallow as much as he could but by the time his ball sack was empty there was a pretty big mess on the front of his trousers, and he was quite sure Mistress Maxine wouldn't be pleased.

However, oddly enough, when Debbie took his mouth off Robin's limp penis and Maxi got a good look at the pants, she only seemed mildly annoyed.

"Clean up your mess fag."

Debbie didn't have to be told twice, and after pausing for a moment to savor the sight of the creamy jizzum clinging to the thick ribs of his trousers, he slowly licked up one glob after another until his pants were nice and clean.

He was in corduroy fag heaven.

Robin never said a word to him the whole time, but Debbie could tell he liked having him as his cocksucker. Maxi ordered Debbie on his feet and told robin to zip up his pants and leave, but reminded him to be back in an hour. As he was walking out she added. "And Robin, make sure your dick is ready to give the fag another workout."

After he left, Maxi told Debbie to sit down and Sonya showed up with two drinks.

"I know it's a little early in the day, but what the hell princess, you've got a long day ahead of you." She chuckled and took a sip, and Sonya again gave Debbie a dirty look as she left.

He wasn't sure if he should take a sip or not, she could be baiting him into doing something stupid. Mistresses sometimes did that to their fags. But after her second sip she said. "Go ahead tinkerbell, drink up."

They talked for a while and Debbie was surprised that Maxi was carrying on a civil conversation with him. Make no mistake, she was still talking to him like he was a piece of fag shit, but there weren't any threats and the insults were kept to a minimum. For his part Debbie made sure he didn't forget his place and get too familiar.

She asked him why corduroy turned him on so much and why it made him such a cock whore, and he related his first experiences with corduroy, crossdressing and sissy sex. He told her how much seeing a cock sticking out through the zipper of a pair of corduroy pants excited him, and how worshiping corduroy and cock had evolved into one of his favorite things to do in life. In addition, being forced to lick up another guy's sperm off a pair of corduroys had become an obsession, he wanted to do it at every opportunity. It was both humiliating and very sexually exciting.

She listened and at times seemed interested, but other times she dismissed what he was saying with a smirk, as if it was pathetic. After a half an hour or so she told him to kneel down in front of her and she spread her legs to let him get in close. She asked him if seeing a woman in corduroy still turned him on, or was he transitioning into some kind of queer. He explained that he very much enjoyed seeing a woman in corduroy, in fact seeing a woman with a dildo sticking out of her pants excited him every bit as much as a real dick.

"Well fag, don't you ever want pussy?"

"Yes Mistress I do, but I'm not allowed to fuck anyone but my wife, and although I'm expected to lick and worship other mistress's pussies with enthusiasm, my mistress would be very angry with me if she thought I was dreaming about fucking them."

She took a sip and had a sly smile. "Tell me Debbie, do you want to fuck me?"

Alarm bells suddenly rang in his head, he was entering very dangerous ground and he knew it.

Thinking quickly, he said. "Mistress Maxine, you're an extremely beautiful woman and the most dignified mistress I've ever had the pleasure to serve. But my useless penis not up to your standards so I'm not worthy of even fantasizing about having sex with you. It would be an insult to your queen like stature for a worthless little cocksucker such as myself to even think about defiling your charming femininity with his pathetic sissy penis. My respect for you as club matriarch, and your superiority as a beautiful woman, would never allow me to insult your dignity like that."

She stared at him blankly for a few seconds, then smiled and spoke slowly. "Oh Princess Penis Licker, you really know how to lay it on thick don't you? You've obviously been well trained, perhaps I've underestimated your wife."

Maintaining her smile she pointed between her legs. "Alright Debbie, that got you off the hook for the time being. Now get your face in here and kiss my corduroy crotch, and fag, I better see as much enthusiasm as I saw when you were kissing Robin's pants."

Debbie was a bit shocked, but in a very pleasant way. He raised his hands to put them on her legs but wisely stopped.

"Mistress, may I touch your pants?"

"I don't wear pants faggot, I wear trousers or slacks, and yes you may."

He laid his hands on her thighs and the feeling of the corduroy was heavenly, even more than he thought it'd be, and his cock sprang to attention under his skirt. He leaned in, gently rubbed his face against the inside of her legs and let out a moan. She liked hearing that. Not wanting to try her patients, he spent only a minute or two enjoying her pants before working his way up to her crotch, he then kissed it all over and let out little moans.

A few minutes later, he paused and said. "Mistress I love your corduroy pants, I mean trousers. Thank you for letting me kiss your crotch, may I kiss your trousers freely now?"

"Go ahead fag, just behave yourself or I'll kick you in the balls." She nudged the toe of her shoe against his dick for emphasis.

He was ecstatic and began kissing all around the front of her pants enthusiastically.

As he did, she said. "I hope you like it down there fag."

"I do Mistress, thank you, I..." She cut him off. "Just shut up and listen sissyboy."

"If you're lucky you'll get the opportunity to lick my pussy later, maybe even suck on my titties too, we'll see. However, I never let any fag lick my pussy unless he's made Susan happy first. Are you paying attention faggot?"

He stopped kissing and looked up. "Yes Mistress Maxine."

"You'd damn well better be pantyboy, because if my pussy doesn't get licked I'm going to be one angry Mistress, do you understand me Debbie?"

"Yes Mistress, I do."

"And trust me princess, the last thing you ever want to do in this world is get Maxine Montgomery pissed off."

She let those words hang in the air and he slowly lowered his face to her pants.

*************************************************************

About twenty minutes later Robin returned and sat in the other chair. Debbie was still kissing and fondling Maxi's trousers as she watched TV, and he felt like he was in sissy-fag heaven.

He heard her say. "From what I see Robin, I take it you're ready for round two."

"Yes Mistress, I am."

Debbie snuck a peak and saw that Robin's dress pants were tenting a mile high.

"That's good dear, because I have a little chore for you to perform before Susan returns. I want you to loosen up Debbie's bottom for my girl's big dick. Susan hasn't been laid in a while, and I'm sure she's going to want to bury it right to the balls when she finally gets it inside our little Debbie. Seeing as how you almost have a real dick, I want you to be a good boy and loosen him up the best you can. Otherwise the bitch might pass out if he's not properly prepared. And Robin dear, you can cum in his rectum if you'd like.

Debbie didn't like the sound of that but kept kissing Maxi's pants.

"Tell me Debbie dear, did you clean yourself out before you came over today?"

"Yes Mistress, I did."

"I'm glad to hear that fag, because if I see one little turd at any time today, someone will be going home with their sissy balls in a jar."

Again, her threat of castration didn't even sound like a threat at all, it sounded more like a simple reminder, and for some reason her being so nonchalant made it sound even more chilling than if she was pissed off.

"Stand up and turn around Robin, it's time for Debbie to act like the little cock whore he is."

"Back off fag, right now!"

Debbie retreated back so he was sitting on his heels.

"Robin dear, take your jacket off, put your hands on your knees and stick your ass out at Debbie."

He did.

Pointing at his bottom, she said flatly. "Go kiss the man's fanny. Kiss his ass and beg me to make him fuck you, I want to hear you beg to have a dick in your pooper."

An image of the goddess Cordella suddenly flashed through his mind, and he wondered if Maxi was her reincarnation. He looked at Robin's ass sticking out and waiting for him to humiliate himself, and as much as he wanted to deny it, it turned him on like crazy. Both the idea of rubbing his face in the thick soft corduroy pants, and the humiliation of kissing his ass while begging for his dick, played directly into his sissy submissive persona. She wanted him to castrate himself, to willingly surrender his masculinity right in front of her. It was her way of crushing any shred of dignity that might still be lurking about, and the truth was, he loved her for it.

He moved forward on his knees, stuck his face in Robin's ass and spent the next ten minutes proving to the both of them that he was not a man, he was indeed a castrated eunuch willing to do anything his Mistress commanded. Debbie recently stopped pretending that he only did these things to satisfy his Mistress. He now knew he submitted to their humiliation because he wanted them to destroy his masculinity and free will, he wanted to be a completely submissive sissy fag more than anything else in the world. He also realized that his Mistresses knew it too, his previous resistance had been fooling no one.