Casey's Submissive Journey Pt. 07

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club.

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Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really good show. They'd been at it for a couple of hours but Karen had been preoccupied, she and her mentor Audrey had been kissing and petting in one of the bedrooms. Their red-hot relationship had cooled off significantly over the past few months. They still enjoyed making their husbands put on private queer shows for them on Wednesday nights, but their one on one sessions had dwindled off to a few times a month. There was no falling out, they just developed other interests in addition to the one they had in each other. Karen knew that Audrey had started seeing Delia, a new lady in the club, and in truth it really didn't bother her that much.

Audrey was young (twenty-seven to be exact) and she was a sexual dynamo, she was horny all the time. In fact she was as bad as a teenage boy in that respect, and quite frankly at thirty-eight with a husband Karen was happy for the reprieve. Their husbands, Casey and Jamie, still had fun amusing their wives on Wednesday nights and kept their Friday night crossdressing sessions religiously, but their relationship had cooled down too. Karen knew that they would always be connected by corduroy, their mutual fetish would forever bond them, but they too were enjoying a little variety with other sissyboys.

Karen vaguely remembered Betty from years ago and she knew her name was Betty something but she couldn't remember what it was. Betty Ann, Betty Sue, she wasn't sure. Although Karen didn't have any kids of her own, she did some volunteer work at the school years back and she remembered Betty from those days. If memory served, Betty was president of the PTA or something similar, and as soon as she recognized her she couldn't believe she was seeing her at the Lady's Club. She knew she wasn't a member but that really didn't mean much, the ladies occasionally invited guests to observe, so all it really meant was that she knew another member. She guessed Betty was just about the same age as her and she vainly thought she'd maintained herself better. She looked a lot less perky than Karen remembered, but she was still a pretty woman, and Karen had to admit there was a sudden attraction. Since she'd accepted her bisexuality, attractions to other women had been happening much more frequently.

Karen walked over, introduced herself and she reciprocated by calling herself Betty Jean, that immediately sounded familiar. She mentioned her volunteer days at the school and Betty remembered her right away, which pleased Karen a lot. She noticed that Betty's glass was empty, so she asked her what she was drinking and offered to get her another one. When she returned she sat next to her on the sofa and they shared some small talk, nothing special, just some general reminiscing and catching up. As they talked Karen noticed she was wearing a long blue wide-wale corduroy skirt and that made her chuckle inside. She bet her husband would love to wear it, or jerk off with it, or both. Being up close she got a good look at Betty's face and noticed it had lost all its youthful perkiness. Instead it had taken on the weary look that years of drinking can produce, which was unfortunate as she was still an attractive woman. They talked for a little while longer, and as they did she could tell Betty was checking her out from time to time too. She liked that. She informed Karen that shortly after the time they had known each other she got divorced and had been raising her son by herself ever since.

After they relaxed a bit, Karen decided that since they were both watching the boys put on a sex show there was no reason to beat around the bush. She pointed out Casey in his corduroy skirt and vest outfit. He was on his knees sucking Jamie's cock while another fag was giving his ass a good hard fucking. She explained how the club worked, and told her that if she wanted to be a member she needed a husband or boyfriend who was not only a submissive crossdresser, but willing to put on shows for the ladies. Betty nodded and listened politely but Karen got the feeling she already knew how things worked. Karen also pointed out that many of the ladies were bisexual, herself included, and there was a lot of woman to woman action available if that interested her. She took a sip of her drink and gave Karen a very obvious once over, a look that Karen thought showed interest, but then said flatly that she'd never had lesbo sex before. However, after a brief pause and another sip, and added.

"Although at this point, I'm not ruling anything out."

She then changed the subject by complimenting Karen on what a good little sissy whore her husband was. After that, there was a long pause as the two women sipped their drinks and watched the show. Karen thought the two of them had hit it off pretty well and didn't want to ruin anything by pushing it. So instead of trying to make any kind of move on her, she invited Betty Jean to come over one night and she would show her just how well trained her husband really was. She finished her drink and told her that if she ever needed any assistance training a fag-slave, she would be more than happy to help. Then deciding to take a chance she gave Betty a quick kiss on the cheek before she got up and said goodbye.

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The phone rang about 3:30 in the afternoon just as Karen finished on the elliptical, the caller ID said "unavailable" but she decided to answer it anyway.

"Hello."

"Hi Karen this is Betty Jean Dickman. We talked about six weeks ago at a Lady's Club meeting. It was at Maxi Montgomery's house on South Orange Avenue. Do you remember me?"

She sat on the bed. "Yes Betty, hi, I almost forgot about that, how are you?"

"Oh, I'm doing fine Karen, thank you for asking. I um, I was just kind of wondering if you still remembered the offer you made that night? I was thinking that maybe I might take you up on it if I can. That is, if the offer still stands. If not I'm sorry and please just forget it, it's just that..."

"Betty I do remember and the offer does indeed still stand, in fact I'm very glad you called, and even happier that you're interested. You are interested, right dear?"

"Well, yeah, I think it might be fun, and."

"And what Betty?"

"Well, I don't want to say too much on the phone, but I've been seeing someone who might be able to help me get in the club. However Karen, to be truthful, I have no idea where to start. Do you understand?"

"Yes Betty, I do indeed. Actually though, I have a question before we go any further, is it Betty or Betty Jean?"

"I go by Betty Jean, but Betty's fine too."

"Alright Betty Jean, are you available this evening?"

"Ah, yes. Actually Karen, tonight would be good for me."

"Good, I'm glad to hear that dear, why don't you come over around eight, we can have a drink, relax, and I can show you what I wanted to show you. After that we can talk for a bit, how does that sound?"

She chuckled nervously. "That sounds really good Karen, can I get your address?"

"Yes dear, it's 212 Highland Drive. You come in off Ridge Road and we're the second left. Got it?"

Yeah I got it. Actually I'm somewhat familiar with the area, I've been there a few times before. Alright, thank you Karen, I'll see you at eight."

"Oh wait dear, can I ask a favor of you?"

"Sure Karen, what is it?"

"Well, I know this is going to sound a little strange Betty Jean, but as I remember you were wearing a blue corduroy skirt that night, weren't you?"

"Ah, maybe, I do have a skirt like that. Wait, actually I think I was. Why?"

"Could you please wear it when you come over tonight?"

Another nervous chuckle. "Yeah, I guess I could, but why Karen?"

"It has to do with corduroy. Actually Betty Jean if you don't mind, I'd rather explain it to you when you get here. Could you please just do that for me?"

"I guess so, yeah OK Karen."

"Good, thank you, then I'll see you tonight, and Betty Jean I'm really really happy you called dear. See you later, bye-bye."

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When Casey arrived home at five after a long day's work, he found his pretty wife in the kitchen making an early dinner. She was dressed in a pair of chocolate brown mid-wale corduroy jeans, a beige mid-wale corduroy shirt and her brown corduroy ankle boots. He'd seen the outfit many times before, it's one of the outfits she wore when she was in the mood to fuck her fag. Without a word being said he knew his ass was in for a rough ride, the only question left was what did she want him to wear. Hearing him come in, she looked over her shoulder with a smile.

"Hi Casey, dinner will be ready in about 45 minutes, make yourself a drink and go in the bedroom, I've left something special on the bed. It's a brand-new outfit and I really like it, you're going to be such a cutie-pie tonight. And honey, I want you to be a really obedient sissyboy, do you understand?"

She giggled in that cute way of hers and he felt his cock begin to harden, she obviously had plans for him and he loved that she did. The last part of her statement was her way of telling him that there would be someone else involved, and that made everything even more exciting.

He came up behind her, wrapped his arms around her waist and kissed the back of her neck while humping his dick against her ass.

"Yes Mistress, can we start right here?"

She purred and giggled a bit, but then said firmly. "Don't start Casey, I'm very serious, I want you on your best behavior tonight, and that starts right now. Now go!"

The feeling of her corduroy outfit was driving him crazy with lust but her tone left no room for rebuttal. He sighed deeply.

"Yes Mistress, I'm going."

He made his drink and hurried off to find what girly surprises awaited him in the bedroom. Once inside, he smiled at the outfit laid out neatly on the bed, and immediately began to strip. First on was his red lacy bra and his breastforms, which was followed by a white long-sleeve ribbed-knit turtleneck blouse. He then picked up a red mid-wale corduroy skirt and vest outfit and rubbed it against his cheek. It felt wonderful and looked very Christmassy, like something well suited for a sexy female elf in Santa's workshop. Or then again, maybe a sissy elf who sucked all the other elves cocks and made them happy workers. The skirt was knee length, pleated and had no pockets, the only detailing was a light green mid-wale trim around the hem and edges of the vest.

After donning it he put on a red and black lacy garter belt, then sat on the bed and pulled up a pair of opaque green stockings. She obviously wanted him to look fancy, no boring pantyhose. For his feet she'd left out a pair of green mid-wale corduroy elf booties, they had red trim and curled up toes. He wondered where in the hell she found them, especially in his size. Finishing it all off was his strawberry blond wig and a set of silly reindeer antlers attached to a headband. Apparently Karen wanted him dressed for a private Christmas party in which he would be the entertainment, or she was just being a silly girl, and knowing her it was probably a little of both.

Casey took his time and savored the dressing experience, all the while wondering if he'd be whoring for a cock or a pussy. Either way it really didn't matter, what mattered was that Karen never stopped trying to turn him on. She was definitely getting something out of it too of course, after all he was being her slave and she freely had her lesbo affairs, but she never stopped trying to find new ways to excite him with crossdressing, humiliation and corduroy. Even though she couldn't really understand how the combination turned him on, she understood that it did, and she always found new ways to excite him with it. The fact that she loved him prevented her from providing the truly nasty end of the spectrum a disconnected Mistress could, but she found other ways to control him instead.

She repeatedly proved she understood his perverse desires better than anyone else ever could, and as a result Casey would never dream of disobeying her in any way. He would never risk pissing off the one person in the world who truly understood him, someone who understood him perhaps better than he understood himself. No matter what she had planned for the evening he knew he was going to love it, he would love it because his Mistress had planned it, it was that simple. He was hers, and he always wanted to be hers, in any way she wanted.

Once he was dressed he admired himself in the mirror for a while as he finished his drink. When Karen called he swished his fanny out to the dining room and they had a lovely supper. As they ate he fell more and more in to his sissy Debbie persona, and Karen helped by complimenting his girly appearance and providing some very dirty talk. She even described in great detail, a fantasy she had of her and Debbie being in a restaurant with a well-hung waiter. After their dinners arrived she requested that the waiter give Debbie's meal some of the special house sauce, and the waiter was more than happy to comply. He unzipped his corduroy pants, pulled out his big hard boner and jerked off a huge load of creamy jizzum all over Debbie's food. She then ordered Debbie to eat. About halfway through dinner she requested a different waiter unzip his corduroys and do the same, and of course she insisted that Debbie finish ever bite of his meal and lick his plate clean. When they were done, she realized she'd forgotten her purse and made a deal with the waiters to have Debbie suck them off in lieu of payment. Needless to say, Debbie ate his meal with a raging boner tenting his pretty skirt.

When dinner was over she instructed him to clean up, make them both drinks and meet her on the sofa in the living room. He did as told quickly. When he arrived with the drinks Karen was sitting back very relaxed, and she looked extremely sexy in her corduroy outfit. As he handed her a drink she noticed that his skirt looked like a circus tent and chuckled. The television had a video playing of a Mistress fucking the shit out of her fag. It was one of his favorites, and he knew it was another clue as to what she had in mind for the evening. He obediently stood in front of her awaiting instructions, and after humiliating her sissy elf for a few minutes she told him to sit on the couch.

"Tonight Debbie dear, we're going to have a visitor, her name is Betty Jean Dickman and I've invited her over to observe what a well-trained fag-slave you are, so you better be on your best fucking behavior tonight bitchboy. Got it?"

Mistress Karen was coming out in full force, and he loved it.

"Yes Mistress of course, I will behave."

"I mean it fag, God help you if you embarrass me while she's here."

She told him how they met at the club while watching him suck Jamie's cock, then further explained that she liked Betty a lot and wanted to help her join the club. She was also thinking about letting Betty use Debbie to help her train her fag. Without anything else being said Debbie immediately knew two things, Karen wanted to get into Betty Jean's pants, and he loved the idea of being used as a tool for fag training. She told him Betty would be arriving around eight but she wouldn't be summoning him until nine or nine-thirty. During that time he was to give himself an enema and get cleaned out, she didn't want any messes while he was on display for her friend. Then pointing at his tented skirt she instructed him to put on panties to keep it under control. She gave him a few minutes to finish his drink, then ordered him on his knees and told him kiss her crotch. As he did she gave him a few final instructions, then sent him on his way. A few minutes later, while filling the enema bag in the master bathroom, he heard the doorbell ring, and that brought a big smile to his face.

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When Karen opened the door, she liked what she saw. Betty was wearing a light brown trench coat that came to mid-calf, it was smartly styled and done in a wide-wale corduroy fabric that looked very soft. Karen liked the idea that Betty picked up on her reference to corduroy and was trying to be accommodating, it showed a genuine interest on her part. Her long full bodied brown hair was lying neatly on her shoulders in a very attractive way, and Karen had to resist the urge to caress it.

"Your hair looks lovely Betty Jean."

She smiled. "Thank you, I go to Maria's over in Willow Grove, I like her and she does a really nice job. Here Karen, I brought a bottle of Scotch, I think that's what you were drinking at the club. I didn't know what brand so I just took a chance."

"Thanks Betty Jean, that was very thoughtful, please come in dear."

Once Betty was inside, Karen put down the bottle on the end table and stood in front of her. She looked nervous.

"I really like that coat, it's very beautiful, may I touch it?"

Betty was a bit surprised by Karen's immediate invasion of her space, but she kind of liked it too.

"Ah, yeah, sure go ahead."

Without breaking eye contact, Karen caressed her upper arm and Betty knew right then that her suspicions were correct, Karen was definitely trying to seduce her. She had somewhat expected it so it wasn't a big surprise, but even though it turned her on and she was seriously considering taking a walk on the wild side in the future, she had no intentions of following through with any of that tonight. Karen was in fact trying to make inroads with her, but she was also thinking about how much her coat would turn Casey on, and debating whether or not to ask her to put it on again later.

Betty Jean broke eye contact while loosening the belt of her coat and Karen took it as a hint to retreat a bit. As she took a step back, Betty removed her coat revealing the powder blue wide-wale corduroy skirt Karen had asked her to wear, and it was accompanied by a matching blazer.

She said timidly. "I think this is the outfit you wanted me to wear, isn't it?"

"Yes Betty Jean, it is, thank you so much, it looks very nice on you."

She ran her fingers up and down the lapel of her blazer, the addition of the jacket was a very nice bonus.

"I like the blazer too, I don't believe you had it on that night."

She released her lapel, then picked up the bottle.

"Why don't you have a seat on the sofa and get comfortable? I'll go make us a drink."

Betty was expecting some sort of explanation regarding corduroy but quickly realized none was coming, so she took a seat. Karen left and when she returned with the drinks she settled in on the sofa too. Betty then surprised her a bit with her boldness.

"That's an interesting outfit Karen, it fits you well, but isn't it a bit butch?"

Karen looked down at her attire, smiled and decided to just plunge in.

"Yes Betty Jean I guess it is kind of butch, but in a little while I'm going to strap on a big dildo and fuck my sissy husband in the ass, so it's appropriate."

She took a sip and checked out Betty's reaction. Her face registered a small shock but nothing major, then she looked at her lap. Karen was emboldened by her lack of surprise.

"You see Betty Jean, when Casey, or Debbie, is all girlied up and getting fucked, he likes his Mistress to be a tough bitch, so this outfit is my way of adding to that persona. Besides, when I make him suck cock he loves doing it when the guy's dick is sticking out through the fly of his corduroys. So, I stick my cock out of my pants too."