Casey's Submissive Journey Pt. 12

Mistress Maxi -- Part 1

Maxine Montgomery was sixty-four years old, five-foot seven-inches tall, and one hundred and forty pounds. She was an attractively handsome woman whose looks and demeanor were very similar to the character Katherine Chancellor on the soap opera The Young and the Restless. "Distinguished" was a very good adjective for Maxine, "arrogant" would be too if her sense of self-importance was actually exaggerated. But in her case with her power, influence and money, she really was as important as she thought herself to be.

She was born into wealth because her father founded a chain of very successful manufacturing plants. She was the only child of a mother who died young and at the age of 43 she inherited her father's business. Being an educated and determined woman she took a hands-on approach and ran the business very successfully. In fact she expanded her product line and almost doubled the number of factories in her empire.

For the most part, her success could be attributed to the fact that she was a no-nonsense woman who didn't take shit from anyone. Her demeanor was firm but pleasant, unless of course you rubbed her the wrong way or failed to perform your duties properly, in those cases she could easily be described as a castrating bitch. With her money, connections and power she could be a very dangerous enemy. On the other hand, if she took a liking to you she could be an invaluable ally, someone who could open doors you didn't even know existed.

In general she was a calculating woman used to getting her way, and she possessed the power, intelligence and means to see that she did. Maxine, or Maxi to those in her good graces, was never a social butterfly. She didn't date much and found most of the men in her circles either weak and snobbish, or boorishly arrogant. She did have some flings over the years but nothing she ever considered love, and by the time she inherited her father's business she was still unmarried. She liked sex, but like everything else in her life she needed to be in control, and the men in her social class generally didn't like that in a woman. In her college days she experimented with her roommate Patricia on a few occasions and found the sex to be exciting, but she never acted on those urges again after that. Not because she didn't like it, she just never found herself with anyone who raised the subject again, and the urges weren't strong enough for her to pursue another woman.

Maxine Montgomery's one true secret was that she loved pornography. In fact, she was a bit obsessed with it and loved to masturbate while indulging. She knew that by gravitating to such things it made her different than most women, but that didn't bother her, and being very wealthy she had no problem discreetly acquiring whatever she desired. She enjoyed masturbating to many forms of pornography but her main preference was heterosexual. And although she would be loath to admit it, she loved seeing and fantasizing about very large cocks. To Maxi anything smaller than a ten-inch dick wasn't really a dick at all. That explained her marriage to Bruce, or Susan as he currently called himself.

One night about two years after taking over the business, she was in her office working late while a maintenance man was fixing her air conditioning unit. As usual, Maxi had a couple of drinks after hours and was feeling a little tipsy. She danced around a drinking problem on and off her whole life, but it never really became a serious issue. The office was warm and at one point she removed her Jacket and opened several buttons of her blouse. The guy, who was twenty years younger took that as her flirting with him. To be honest, she would later admit that it was. It may not have been the Duchess and the stable boy, but it was something along those lines. When she unzipped his pants she almost fell out of her chair, his dick was enormous, bigger than anything she had ever seen before, and they wound up having sex right on her desk. His name was Bruce, and they were married ten months later.

Shortly after their marriage she let Bruce in on her pornography secret, and they both went about enjoying it together. However, after a while she found some crossdressing magazines and asked him if he was getting turned on by men in drag. He admitted that he was, but more importantly he liked to dress in drag and act girly himself. At first she was devastated, she thought her marriage was headed for an end, but when push came to shove she knew that she loved him and would never leave him over something like that. So she set out to learn everything she could about his sissy desires. She offered to be his Mistress and fuck him with a strap-on dildo, which he definitely liked, but it soon became apparent that it wouldn't be enough to replace his desire to have sex with other sissyboys.

Her fears remained for a while until she finally came to understand that he had no desire to have sex with other women, or other men for that matter. He was a closet sissyboy who wanted to have sex with other fags, and he made it clear to her that he still liked women and wasn't looking to replace her. When that happened she relaxed a little and accepted the idea of him having occasional sexual encounters with other tinkerbells.

However, the world was full of disease and she didn't like the idea of him picking up strangers. So Maxi being Maxi, used her intelligence, determination and the internet to find other women whose husbands were closet fags. It took a while, but after six months she made friends with another woman in a similar circumstance and they decided to make a pact. They had their husbands tested and when they were sure things were safe they allowed their faggots to have sex with each other on a regular basis, as long as they agreed not to have sex with anyone else. Occasionally the ladies would even watch. As time went on she found additional ladies and after two years there were a dozen couples in her "club".

Along the way the ladies discovered that all their sissyboys were submissive to one degree or another, and they all craved female dominance. Some of the ladies had already adopted the mistress role with their fags and they helped train the less initiated girls who wanted to learn. They also started having once a month meetings, and after the first few they started bringing their husbands. They let them dress up girly and have a sissy orgy while they watched and ordered them about. They called it "Fag Night" and their tinkerbells loved it.

While bullshitting at one of their meetings Maxi and some of the other ladies discovered that they liked watching men have sex with each other, as men, not faggots. They kicked around the idea of watching homosexual videos at the next meeting, but after discussing it at length they decided that instead they would create "Homo Hubby Night" and hold them in between the Fag Nights. On those nights their husbands would be dressed masculine and suck and fuck each other for the ladies' entertainment.

They found that the best way to do it was to make two of the guys be "homo whores" for the night, and the rest of the guys could fuck their mouths and asses as many times as they wanted. Most of the guys didn't have a problem with fucking another guy, but very few liked the idea of being a masculine bitch other men. That's why the ladies decided on doing it with the two homo whores, it meant that if they didn't like being a man bitch they only had to do it twice a year. They also all knew that if they wanted Fag Night they had to give the ladies a good show on Homo Hubby Night first. The guys did it too because they knew with Maxine's money, power and connections, having her as their wife's friend could come in very handy. So everyone wanted Mrs. Montgomery happy at all times. Conversely, they knew that if they pissed Maxi off in any way she could make their life miserable.

The name of the group was originally just "The Lady's Club", in fact some people still called it that, but years ago someone told Maxi about the Greek goddess Cordella, and she loved the story. The short version says that Cordella was a beautiful goddess whose fiancé turned out to be a homosexual, and he jilted her for a man. She became so enraged that she made it her purpose in life to make men suffer. She used her beauty and seductive powers to turn men into willing sex slaves, then once under her power she forced them to have sex with each other for her amusement. There was a lot more to the story but that was the gist of it. So Maxi renamed the club "The Sisters of Cordella", because on Homo Hubby Night that's what the ladies were doing to their husbands. There was also a passage in the story about Cordella punishing her slaves with "colossal symbols of humiliation" and someone found out that meant really big phallic objects. So apparently she enjoyed fucking their asses with huge dildos too, that part amused Maxi a great deal.

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All that set the stage for why Casey was standing at the front door of the Montgomery mansion carrying an overnight bag. He was wearing a pair of maroon, mid-wale corduroy lady's jeans and a black polo shirt. He didn't usually wear lady's pants in public but he knew he'd only be exposed while driving to Maxi's, so he gave himself a little sissy thrill. In his overnight bag was a black, wide-wale corduroy skirt/vest outfit that his wife-mistress Karen bought for him to wear for his date with Susan, Maxi's husband, sometimes known as Brutus. In addition he had a long sleeve, ribbed-knit turtle neck blouse along with his bra and breast forms. The blouse was crimson in color and the bra was black. His outfit would be completed with a pair of dark pink textured stockings, black garter belt and black corduroy Mary-Janes. With that outfit Karen decided she wanted him to be a redhead, so he had his shoulder length red wig with him. While bullshitting with Karen a while ago Maxi told her that her husband thought red and black were sexy colors.

His asshole was still a little sore thanks to the punishment administered by Mistress Dorothy the day before, but it wasn't a problem. If anything it was a pleasant reminder of her beauty and Italian princess bitchiness. He enjoyed his day with Dorothy and her fag Julian and hoped Karen would be sending him back there in the future. When he got home he asked Karen if what Dorothy said about running a "slow train" on him was true, and she confirmed that it was. That scared him a little, and excited him a lot. He also asked if she was being truthful about the cocks he sucked while blindfolded, and although Karen was a little pissed off that she blabbed her secret, she again confirmed what Dorothy said. The dicks he sucked did indeed belong to two members of his softball team, and she'd see to it that he sucked their dicks like that on a regular basis from now on.

By then the demure woman he married had completely disappeared, Mistress Karen had taken over, and it was all his own doing. He coaxed her into exploring her dominant side and now had to live with the fact that she loved being a Mistress, far more than he ever thought she would. There was no going back, Karen was his full-time mistress and Casey was her obedient sissyboy slave, end of subject.

Casey took a deep breath and pushed the doorbell. The door opened to what he assumed was the maid. She was dressed in a smock top, corduroy slacks and sneakers, all of it in black. She looked nothing like Casey's idea of a maid. She was a slender Hispanic woman in her mid-twenties and reminded him of a young Rita Moreno. Standing about five-foot six-inches tall, she had shoulder-length black hair and spoke with a fairly thick accent. She looked very bored, almost to the point of annoyed.

"Can I help you?"

Casey explained he was there to see Maxine but she cut him off in mid-sentence.

"I know why you're here maricón, follow me." Her tone was very snotty.

He followed her down a long hall and into a pink sitting room where Maxi was drinking tea and watching a large screen TV. The maid pointed to the middle of the room.

"Stand right there you fucking maricón."

He did so obediently.

Maxi was not the least bit fazed by her rudeness or insult.

"Thank you Sonya, that will be all for now dear."

Sonya left, but not before giving Casey a very dirty look.

Maxi then turned her attention to Casey and gave him an insincere smile.

"You'll have to excuse Sonya, she has nothing but disdain for sissyboys."

She chuckled. "You'd think working in a house with Susan she'd have been fired long ago, but the dear girl is smart enough to keep it to herself when Susan's around. Personally, I think the way she treats you fags is amusing, in fact I encourage it."

She sipped her tea and watched a report on the stock market for a minute, making no effort to put him at ease. She was dressed in a pretty peasant blouse, it was white with a blue floral pattern, had a slight V-neck and tassels hanging down from the collar. Her breast were fairly large and filled her top out nicely. Below she wore a pair of powder-blue, designer mid-wale corduroy jeans. They fit like a glove, snug but not tight, and the corduroy fabric looked plush and expensive. Other than her wedding ring she wore no jewelry, which surprised Casey a bit. Her face and neck had a few wrinkles and showed some wear, but there was no sagging and she looked rather good for her age.

She finally put down her cup, folded her hands in her lap and gave him a forced smile.

"Alright sissyboy, let's get some basics out of the way. My name is Maxine, to people I like it's Maxi. To you it's neither, to you it's Mistress. If I take a liking to you, which is doubtful, you may get to address me as Mistress Maxi. The only way that'll ever happen however, is if you prove to be a good pussy licker. And the only way you'll get a chance to lick my pussy is if you first make my husband Susan a very happy fag.

You've probably heard the rumors about Brutus, saying he's mean to other sissyboys, well that's all bullshit. I don't know who started that rumor but if I find out they'll be in deep shit, and if I ever hear you refer to him as Brutus I'll have your sissy little nuts snipped off."

She leaned forward, lowered her voice and had devilish smile.

"Don't tell anyone pantyboy, but I have people who really enjoy doing that sort of thing."

She chuckled and seemed amused.

Casey's had his balls threatened by mistresses many times before and it was always mistress talk, it never really faze him. But her threat was so cold and matter of fact that it didn't sound like a threat at all, it sounded more like a promise. Whatever it was, he didn't like it.

She leaned back and spoke formally again.

"The only truth in that rumor is that my husband is very well endowed, actually sissyboy, his cock is fucking huge. Now it's true that he has hurt a few fags with it in the past, but he only did it after they called him Brutus or mocked him. My husband is normally a very delicate sissy who is gentle with sister sissies, if they treat him like a lady. Do you understand Casey?"

"Yes Mistress, I do."

"Susan has gone full time now so it's even more imperative that you reinforce his femininity. From what Karen told me you enjoy being an effeminate tinkerbell yourself, so you should have no problem understanding how my Susan likes to be treated."

She glanced at a notepad on the table next to her.

"So Debbie. Are we clear on that? It's Debbie, right?"

"Yes to both Mistress, I want to please you in any way I can, I want you to be happy with me so you'll be happy with my wife."

She gave him a smirk that said she'd heard it all before, then changed the subject.

"As you can see I'm wearing corduroy trousers. Trust me princess, corduroy is not part of my wardrobe. Your wife told me a little bit about your fetish, and quite frankly I think it's one of the silliest things I've ever heard. I mean satin, silk or even leather I can see, but corduroy for God's sake, that just pathetic." She chuckled.

"However she tells me you're an exceptionally good fag slave when there's corduroy involved, and for whatever reason, it turns you into a cock whore. So I decided, what the hell? If corduroy makes you be a good little bitchboy for my Susan, then I'm all for it."

She paused and then her voice sharpened a bit.

"However, if you give me one iota of trouble sissyboy, I'll make all the corduroy disappear just like that."

She snapped her fingers.

"Then I'll have you tied to a bed and let my Susan rape your bottom all night long. Do we understand each other faggot?"

"Yes mistress, thank you, you are extremely kind."

He meant it too. He got the feeling she wasn't normally this accommodating with other fags, and it made him feel special.

"You damn well better thank me bitchboy, and you better not make me regret my generosity. Now, it's time for you to fix yourself up for Susan, I certainly don't want her looking at that all night."

She looked him up and down with a smirk of disapproval, then shook her head and texted Sonya. She arrived quickly.

"Take Debbie to the dressing room and stay with him until he's finished, then bring him to the playroom. And Sonya, be nice."

She stood up and walked out, and Casey kept his eyes glued to her corduroy covered ass. Even at her age it still swished with grace and a lot of sex appeal. As she disappeared through the door his eyes moved to Sonya, and despite Maxi's words her demeanor hadn't changed a bit.

"Come on maricón, follow me."

He followed her down a hall and they arrived at a large dressing room that had its own bathroom. Maxi's house was absolutely beautiful. Sonya sat in a chair and played with her smartphone while Casey made his transformation into Debbie. After dressing he went in the bathroom and applied his make-up. He wasn't really good at it but he had been taught some basics. He must have taken longer to fix his face than Sonya had expected, because when he looked up he saw her standing in the mirror behind him. Her arms were folded across her chest and the disgusted look on her face summed up her feelings quite clearly, but then she did something that shock the shit out of him.

"Wait a minute puto."

She grabbed his shoulders, turned him around and shook her head in disgust. Then grabbing the eyeliner from his hand she spent the next fifteen minutes redoing his make-up. Twice during her work she shook her head and said. "Fucking maricón." It was the only thing she said the whole time.

When finished, she looked at him with a mixture of pride and disgust, then said. "Let's go puto, you've got a lot of whoring to do for my boss's fag."

She led him down the hall and up a set of stairs to the playroom. He was both embarrassed and excited to be in full drag and swishing his ass around in a strange place, it made him feel both vulnerable and sexy.

The Playroom was large, about twenty foot by forty foot, and well-lit from the morning sun. At the far end of the room was a pair of sliding glass doors that opened to a second-floor balcony, and the rose-colored curtains were open giving way to a beautiful view of the rear gardens. Being a gated estate they obviously weren't concerned about anyone looking in. On the far wall in front of the sliding doors was a king size bed with a beautiful tufted headboard. It was covered with a blue and pink checkered corduroy bedspread, and the four large day-pillows were covered with matching shams. Maxi would later explain that all the corduroy involved was her gift to Karen, letting her know that she forgave her and believed her slight was unintentional. She was quite sure that in the future Karen would be sure to offer Debbie's ass to her before any of the other ladies.