tagTransgender & CrossdressersCasey's Submissive Journey Pt. 09

Casey's Submissive Journey Pt. 09


A day With Dorothy -- Part One


The Players

Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen.

Karen -- Wife/Mistress to Casey and member of the Lady's Club.

Julian - Submissive closet sissyfag owned by Dorothy (Dottie)

Dottie -- Wife/Mistress to Julian and member of the Lady's Club.

Maxie -- President and founder of the Lady's Club.


Casey arrived at Dottie's house on Monday morning at 10:00 AM dressed in a pair of corduroy jeans and a plain white t-shirt, just as his wife Karen had instructed. After being insolent at Mistress Betty's house two weeks earlier, Karen became enraged and went into full mistress mode. She insisted he call her mistress at all times, and except for Friday nights he's been required to stay in his masculine homo hubby character 24/7, no crossdressing as Debbie. She even removed his feminine corduroy wardrobe so he couldn't masturbate with anything girly. When he's been allowed to jerk off with corduroy at all, it's only been with a pair of Jamie's pants. Jamie lives next door and is the husband of Karen's mentor Audrey, he's also Casey's sissy dress up partner. Audrey let Karen use him in Casey's training prior to her being accepted into the Lady's club.

Since the Betty incident, Karen also insisted that he suck Jamie's dick anytime Casey saw him wearing corduroy pants, no exceptions, and Jamie's been taking full advantage of the situation. He shows up at their house almost daily wearing corduroys. She did however throw him one bone. She allowed his weekly Friday night fag sessions with Angie (Jamie's fag persona) to continue as usual.

Most of the people privy to the situation suspected Karen was punishing her fag in such a grand fashion simply to make a name for herself among the ladies, but Casey knew different. Karen began her journey into the Mistress/Slave world to please Casey, she had very little interest in being dominant, she was by nature quite demure. Audrey seduced Karen into exploring her bisexual desires, and in so doing found out about Casey's sissy submissive side. She then groomed and goaded Karen into taking charge of her own sex life, and taking charge of her husband by his sissy balls, quite literally. It was no secret that Casey and Audrey didn't like each other, but he was willing to put up with her in order to be a sissy slave to the two mistresses, especially when he found out that Jamie was a corduroy loving crossdresser just like him.

One of the unforeseen aspects of their sexual games was the discovery that Karen really liked watching two guys having sex. Seeing Debbie and Angie having sissy sex was cute, but the first time she saw the boys dressed masculine and having sex, it turned her on like crazy. Audrey made them wear matching uniforms (in corduroy of course) and play out a prison scene for the girls to watch. Although Jamie was younger, he'd had a lot more guy to guy experience than Casey, so Audrey put him in charge, and the girls really enjoyed watching him fuck Casey's mouth and ass. Watching her husband be a bitch for Jamie's big ten-inch dick made her horny as hell. She also liked watching Audrey's collection of homosexual porn videos when the girls had sex, and at some point she decided it was something she really wanted to see a lot more of.

Casey suspected that Karen was using his disobedience at Betty's house as an excuse to push him further down the homo hubby road. He also guessed that her decision to lend him out to Mistress Dorothy for the day, was just another attempt to establish herself as a serious mistress. Mistresses lent their fags out quite often, but previously Karen had only lent him out to Audrey and Betty, two women she wanted to have sex with. As far as he knew she didn't have any sexual interest in Dottie.

Dottie's husband Julian answered the door with a warm smile and asked him in. Julian was in his mid-thirties which was about ten years younger than Dottie, she'd obviously robbed the cradle. He was a small petite fag who rather appropriately went by the girly name Julia. Today though he wasn't dressed like a sissy, he was wearing a pair of black mid-wale corduroy jeans with a red t-shirt tucked in. The pink letters on the shirt said, 'Suck it Bitch' with an arrow pointing down. He remembered Julian/Julia from the Lady's Club on both 'Fag Nights' and 'Homo Hubby Nights'. They had sucked each other's dicks before and Casey remembered that even though he was a small wimpy fag at 5'6'' and not much more than a hundred pounds, his dick was an impressive eight inches with a large handsome mushroom.

He was sure Julian must've fucked him in the ass on his initiation night, but Casey was so busy sucking dicks while being fucked that he couldn't remember who was fucking him at any particular time. Well, except for Jamie, Terry, or especially Brutus. At ten, eleven and thirteen inches you always knew when they shoved those monsters up your shitter. He also remembered Julian because he wore corduroy pants on Homo Hubby Night, and when he thought about it, he seemed to remember seeing him in a corduroy dress on one or two Fag Nights.

Julian gave him an obvious once over and he seemed to like what he saw. "Hi Casey, I'm really glad you came, Mistress is waiting for you in the den. Please follow me."

As Casey followed he kept his eyes on Julian's fanny, he had a natural sissy swish, it didn't seem forced at all.

Arriving at the den he saw his mistress for the day seated in an armchair filing her nails. She was talking to a pretty young black woman dressed in a pair of tan overalls and a solid red t-shirt. He recognized her from the Lady's Club, her name was Tina, and if he remembered correctly her husband's fag name was Kendra. The boys stood quietly while the ladies completely ignored them, and as they did Casey caught Julian leering at his crotch with a silly grin. Dottie had her hair up in curlers and her toenails looked like they had just been painted, it appeared she was getting dolled up to go out.

She was dressed in a very loose-fitting, orange, mid-wale corduroy house coat. It zipped all the way up the front, had two patch pockets and a large peter pan collar. Both the collar and pockets were done in a tacky black and tan leopard print. Casey was no fashion expert, but even to him it seemed rather gaudy. However, as he eyed the frock he had to admit, as gaudy as it was, he'd love to rub his boner against it and come all over it. By then it'd been three days since Karen let him jerk off, and he was feeling that way about anyone dressed in corduroy, man or woman. As he waited to be recognized he studied his new mistress. Her gum chewing and New York accent combined with the nails and curlers made him think of a bitchy Italian housewife at the beauty parlor in the 1960s.

After ten minutes or so, their conversation about a TV show Casey had never heard of came to an end. Tina slowly eyed Casey up and down, then wiggled her hand in a gesture meant to indicate a so-so rating.

"Is this Karen's bitch?"

"Yes dear, I'm doing Karen a favor today, and I'm hoping she's going to return the favor tonight" She winked at Tina and they both chuckled.

"Well girl, it looks like you've got a busy afternoon ahead of you, so I'll leave you to it. Give me a call tomorrow and let me know how your date went."

She got up and took a few steps then stopped and put her face right in front of Casey's. She gave him a hard stare and a sneer, then started rubbing the bulge in his pants. He had no idea what to do. The ladies generally didn't touch the dick of someone else's fag without permission. She kept doing it until Casey nervously blinked several times and swallow hard. She then started laughing and gave his dick a squeeze before walking out.

Without looking up, Dorothy continued filing her nails and said. "Sit on the sofa sissyboy."

Julian did as told, and without thinking Casey made the mistake of sitting next to him. She stopped filing and glared at Casey like he was a piece of shit. "What the fuck is your problem asshole?"

Immediately realizing his stupidity, he quickly knelt down in front of her.

Her eyes kept boring into his. "Now I know why Karen wants me to give your sissy balls a good hard slapping, you seem to be an insolent little jerk off. What's your girly name again shit for brains?"

"Debbie Mistress, my name is Debbie, and I am very sorry for not showing you the respect you deserve. I know it's not an excuse but I was distracted by Tina, I promise it won't be repeated."

"Well fag, you have no fucking idea how sorry you'll be if it is. And by the way, it's Mistress Tina to you turd."

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

She continued staring as if expecting more.

"I'm very happy my mistress decided to do you this favor, I'm happy she lent me to you for the day. I'll try my best to service you and your fag in any way I can, I'll try very hard not to disappoint you and embarrass her."

She gave him a very strange look.

"What are you talking about turd? She didn't do me any favors, if anything I'm doing her one. She called me up and asked me if I'd make you be a bitch for my Julian for a day, and she made three things very clear:

One: There was to be no girly stuff, this was to be a homo hubby afternoon.

Two: She gave me very broad leeway in how rough I can be with your sissy balls if you misbehave. So don't test me asshole.

And three: She wanted me to record all the sex between you two little homos. In fact, you're being recorded right now.

So you see asshole, I'm the one doing your Mistress a favor, and in return your pretty wife has agreed to go on a date. Tonight, after dinner and a few drinks, we're going to return here so I can show her the videos I made today, and I'm expecting she's be very grateful when I do. Too bad you won't be here for that. Julian on the other hand just might have a really fun day today, if he behaves himself. Not only will he spend all day using you as his fucktoy, but later on he just might get to lick your Mistress's pussy and watch us ladies have sex."

She looked at Julian and said sternly. "That is of course if my husband behaves himself."

The look on Julian's face made it obvious he'd received the message loud and clear.

Holding her hand up in front of her face she gave her nails a close-up look and seemed pleased by what she saw. She then gave Casey a dismissive wave. "Go kiss my husband's pants you little queer, from what Karen told me about corduroy I'm sure you can't wait to get your face in his lap. So go."

She was quite right of course, and Casey was between Julian's legs in an instant. He moaned loudly as he ran his hands all over Julian's pants and rubbed his face up and down the inside of his thighs. He was acting like a drooling pervert and he didn't care. The fact that Karen was making him be a whore for basically strangers turned him on like crazy, it freed up his inner slut.

There was also something about Dottie's femininity and beauty parlor good looks that he found very exciting. Her sassy Italian princess mannerisms and ball busting attitude was something right out of the Sopranos. It reeked of dominance, but not in the manner of a typical mistress. She was pure middle class bitchiness, ready for a cat fight at the drop of a hat. She seemed an odd fit to be married to a closet fag like Julian, especially since he wasn't very far in the closet anymore. Casey liked her so far, and was looking forward to seeing what kind of a Mistress she was.

She let him do his corduroy thing as she tended to her nails, and after a few minutes he rubbed his face up to Julian's hard bulge. Julian was very patient and seemed willing to let Casey have all the fun he wanted, he knew he'd be squirting in his mouth soon enough. In addition, the perverseness of Casey getting all horny for his pants excited him a little.

Without diverting her attention from her task, she said. "So tell me queer boy, why do you like corduroy and cock so much? Karen tells me you like to fuck her and lick her pussy so you're obviously not a full-fledged queer. What is it about corduroy that turns you into a cocksucker? Did somebody make you suck their dick in corduroy pants when you were a kid?"

Casey was so obsessed with Julian's pants that he unintentionally ignored her. She didn't like that. She carefully rose halfway out of her chair and gave him a swift kick in the ass.

"Don't you ever fucking ignore me asshole, I shove baseball bats up the ass of fags who do. I've done it before, just ask Julian."

Julian chuckled nervously and whispered. "She's not fooling around Casey, she means it." Casey wondered if he was speaking from firsthand experience.

He spoke into Julian's bulge. "No Mistress, I wasn't molested, I just love corduroy. The first time I jerked off it was with corduroy, and I've been turned on by it ever since. I love it whenever someone wears it for me, and if it happens to be a guy then I want to thank him by sucking his dick. Plus, if I make his penis feel really good when he's wearing it, chances are he'll wear it again." He resumed kissing Julian's bulge.

"It's got to be more than that. I've seen you on Fag Nights Daisy May and you loved being fucked in your boypussy. No man puts on girly clothes and takes it up the ass unless he's somewhat of a homo to begin with. I know, I married a fag, although I didn't know it at the time. It turns out my husband was abused by his teacher when he was a kid, he made Julian wear a girl's uniform and fucked him several times a week after school. Then after many years of therapy Julian realized the truth, he really liked dressing girly and being fucked right from the start. It wasn't the kind of thing a girl likes to find out about her husband, but I loved him, so I became his mistress, and I now supply his abuse. That's why my man is a fucking pantyboy, what's your story Tinkerbell?"

"I don't really have a story Mistress."

"Would you like me to get my paddle and play Ping-Pong with your sissy balls?"

He sighed deeply. "No Ma'am."

"Then look at me and answer the fucking question."

He pulled his face out of Julian's lap and turned to look at her, but she kept her focus on what she was doing.

"When I was about twelve I got silly one day and tried on one of my sister's dresses, mainly because it was corduroy. It turned me on so much that I jerked off on the spot, and I've loved wearing girly clothes ever since."

He started feeling up Julian's leg.

"I never had sex with a guy until after I was married. I got pretty drunk at a bachelor party one night, and when it was over my wife's old boyfriend talked me into going to his place to shoot pool. After we had a couple more drinks and he started telling me how horny he was and how much he'd love to have his cock sucked. Between my horniness and the booze my curiosity finally got the better of me I ended up sucking him off. Once he unzipped his pants and pulled out his dick I knew I was a goner, seeing it sticking out of his corduroys was too much for me to resist, I just couldn't stop myself. After I did it he told me he wasn't into dicks, he just liked having his cock sucked, but the truth was I really didn't care, I just loved doing it. From then on I started sucked his dick whenever he wanted it, and he always wore corduroys. That went on for a while, and then one night he said he wanted to try fucking me in the ass, and I couldn't bring myself to say no."

She had a bored look on her face and only glanced at him occasionally, but even with her sporadic attention he got the feeling she was genuinely interested in his story, which he thought was a bit odd.

"Even though there was no other woman involved, I began to feel a little guilty, like I was cheating on my wife. So one night when I was drunk I told her all about it, and instead of getting mad she shocked the shit out of me by insisting I suck his dick right in front of her, and a few night later I did. She even made me wear one of my dresses and act like a fag in front of him. She made a big deal out of humiliating me too, treating me like I was a dickless wimp. I probably should have gotten angry and refused to do it, but the truth was it turned me on so much I almost came right in my panties. From that day on she started humiliating me all the time, and I had to be her slave on a regular basis. She even had him come over to our apartment several more times to fuck my mouth and ass, and she always watched and laughed at me when he did it."

He paused.

"May I suck Julian's dick now Mistress?"

Julian liked hearing that.

"You can suck him in a minute fag, but first I have two more questions. Did she make you be a bitch for other guys? And why did your marriage break up?"

Before answering he heard Julian whimper, and when he looked up and saw him giving his wife a pleading look. His patients had obviously worn off and he was ready to for his blow job.

"Calm down Julian, you'll cum in his mouth when I say so, don't piss me off. Now answer my questions fag."

He said there were no other guys involved and explained that after a few months he found out that the dick that was fucking his ass was also fucking his wife's pussy, so they split up. Again, she seemed genuinely interested in his story and told him she wanted to hear more later.

"But for now you better suck my fag's penis before the little wimp starts crying. Go ahead homo, suck his dickie."

Casey really didn't feel like talking anyway and gladly unzipped her husband's trousers. He wasn't wearing any underwear and that helped when Casey pulled his boner out through the fly. Seeing it standing proud just inches from his face it looked just like Casey remembered it, eight inches tall with a nicely shaped mushroom. It was a handsome cock, and it made him wonder why so many guys with large handsome dicks end up being prancing nancies. His mouth started watering as the desire to suck cock overwhelmed him. That happened whenever he saw a dick sticking out through the zipper of a pair of corduroys. Seeing such a sight always removed the element of choice when it came to cocksucking. Very simply, Casey had to suck that cock. In fact, he'd even beg to suck it. Hell, at that point he'd even pay the guy to suck his dick. Such was the power of corduroy.

Sharing the same fetish Jamie was also ruled by that power, and being Jamie's wife and Mistress, Audrey knew how to wield that power over the both of them. In addition, seeing that Karen had requested Dorothy and Julian be dressed in corduroy made him believed his wife now really understood that power too.

His hand closed around the base of Julian's boner, holding it straight up and steady. He stuck out his tongue and started licking up and down the front of his cock, teasingly flicking it across his frenulum each time he passed it, which always triggered a moan in response. He snuck a quick peek at his new Mistress who was being very quiet, she was busy fussing with her nails and wasn't paying them the slightest bit of attention. That was OK with Casey though, at that point he was so horny to drain her husband's ball sack that he didn't need any supervision. He wrapped his lips around Julian's mushroom, took all of it in and let his mouth get used to its size. After a minute he pulled his mouth off with a slurpy pop and immediately began swabbing his mushroom. He even got playfully, trying to wiggle the tip of his tongue into Julian's pee hole. He continued to worship his knob for several minutes getting them both horny as hell. Julian was moaning almost constantly by then and Casey knew he wouldn't last long, he guessed his bitchy wife hadn't let him come in a week. But that was fine with Casey, it meant there'd be a nice big load of jizzum to swallow.

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