Casey's Submissive Journey Pt. 03

Angie & Debbie (Fag Night) Part One

Audrey was dressed in a pair of tight black mid-wale corduroy jeans and had an 18" dildo sticking out through the fly of her pants. She laughed maniacally and grabbed Casey's balls.

"I own you sissyboy. First I'm gonna yank on your sissy balls til you beg for mercy, then I'm gonna fuck your sissy ass with my big cock."

"How does that sound Casey."

"Casey"

"Casey, wake up."

"Come on honey it's 10 o'clock wake up."

He opened his eyes and saw his wife Karen standing over him, his limp penis was sticking out through the fly of his corduroy shorts and she was pulling on it, she sounded a little annoyed.

His head hurt.

He suddenly realized where he was, lying on his back on their bed. Through the fog of last night's alcohol he vaguely remembered jerking off with his best friend Jamie's corduroy pants. He gave a quick look around but the trousers were nowhere to be seen. Karen was still wearing her red corduroy jeans from the night before but now had on pink t-shirt. Parts of what happened the day before with Audrey and Jamie started coming back, but it was all very hazy. He lifted himself up on his elbows and looked at Karen with bloodshot eyes.

"Get up and take a shower. I'm going out for a while, I'll be back around one, we'll talk things over when I get back."

Her tone wasn't nasty but it wasn't pleasant either, she was obviously not happy. She let go of his penis and walked out, and even with his hangover he couldn't help staring at her corduroy covered ass. He had to piss, and when he slid his ass off the bed he was suddenly hit with a bolt of pain straight up his rectum. His asshole was sore as hell and the memory of Karen fucking him with her big dildo came flooding back. As much as it hurt though, those memories made his limp penis begin to harden.

After taking a piss, Casey got in the shower and let the water run over his face for a minute. He tried to remember all of what happened yesterday with his neighbors, and last night with Karen. He remembered being tied up, Karen and Audrey jerking him off, and they had a lot to say about something. What was it now? Something about a Lady's Club with faggot husbands, that's right, Fag Night orgies and Homo Hubby Nights. Then he remembered about Jamie's corduroys. Karen and Audrey took away all his girly clothes and they wanted him to jerk off with Jamie's corduroy pants. Then the memory of Jamie in full drag came rushing through. Angie, that was the name. Angie looked so fucking good in Casey's sailor dress, and as crazy as the thought was, his buddy in drag was sexy as hell.

He now had a boner and was waking up. His mind flashed on the vision of Angie licking up his sperm off the black corduroy jeans. He started to lather himself up, then suddenly remembered finding out that Audrey and Karen have been having sex, and the picture of them making out popped into his head. He also remembered fighting with Audrey when she said she owned him. There was so much that happened he was having a hard time wrapping his mind around all of it. However, his thoughts kept returning to Angie in the corduroy dress, and he began stroking his boner with a soapy hand.

He fantasized for a bit but reality came crashing in when he reached back and rubbed the soap against his asshole. He actually gave out a small yelp, and the memory of Karen raping him played out in his mind. Her big dildo hurt so fucking good, and he remembered how well she played the mean Mistress role. He always liked having a sore anus after being fucked, it was a pleasant reminder of his submission, but judging from the way his asshole felt he guessed he'd be remembering last night's fucking for long while.

He wanted to cum but remembered that his wardrobe was now in Audrey's closet, so he had no girly corduroy clothes to jerk off with. He thought about masturbating with his soapy hand, but then remembered he jerked off with Jamie's pants before he passed out. He managed to break through the man-pants barrier last night and he figured he could do it again today. He would much rather stroke his dick with corduroy anyway, so he decided to wait and find his buddy's pants.

He got out of the shower, dried off and put his shorts back on with a fresh t-shirt, he intentionally wore no underwear. He searched the bedroom for Jamie's trousers, and not finding them, he wandered through the house trying to figure out what she did with them. Reaching the other side of the house he heard the washing machine running and put two and two together. He wasn't happy about that, but then he suddenly remembered the corduroy bath robe Karen had given him the night before. He went back to the bedroom closet, but it wasn't there, and after a few minutes of searching he gave up. He also discovered that all of Karen's corduroys were gone too, so apparently Audrey wasn't lying yesterday and the girls were serious about this man-pants thing. Not thrilled with the idea of using his corduroy shorts, he resigned himself to the fact that he had no corduroys to jerk off with. So instead he decided to have something to eat and check in with a couple of porno sites he liked on the computer. After an hour, he remembered that Jamie's pants were in the washing machine and checked to see if they were done. They were. So he put them all in the dryer, hoping they would be done before Karen got home. He spent the next hour with his attention being divided between crossdressing porno pictures and his memories of the previous day, and no matter which way his mind went, it kept his boner as hard as a rock.

Around 12:30 he checked on Jamie's pants and decided they needed another fifteen minutes. He hoped if Karen came home a little late, he might have enough time to get in a quick stroking with his buddy's green corduroy jeans. Ten minutes later he heard the back door open and his hopes were dashed, Karen was home. Quickly shutting down the computer, he slipped into the Den and put on the TV. Karen passed by and went in the bedroom without even saying hello, and when she emerged Casey's poor aching boner wanted to rip right through his shorts. She was wearing a long, brown, mid-wale corduroy skirt. It was a pleated A-line, and he hadn't seen it in a long time. It was the first item of corduroy clothing she bought after finding out about his fetish almost fifteen years before. Casey loved it, not only because it was a great skirt, but because it was the first corduroy thing she bought specifically to turn him on. For many years she wore it often, but over time less and less. Then she started wearing it only on special occasions, or any time she really wanted to get him horny, because she knew it would always give him a boner. It was paired with a plum colored ribbed velour blouse that she bought many years ago. The ribs of the blouse were wide and Karen thought they looked kind of like a wide-wale corduroy, she thought he might like that, and she was right. Beneath she wore a pair of brown knee high suede boots.

They stared at each other for a moment, and they both smiled like a couple of teenagers getting ready to make out, just like they always did when she wore that outfit. He got up and hugged her and they kissed for several minutes. He told her how sexy she looked several times as he caressed her, and he hoped his boner was going to find relief either in her pussy or with her skirt, but Karen had other plans. Wearing the outfit was Audrey's idea, and it was meant as nothing but a tease. She let him go for a few minutes, getting himself all worked up, then gently pushed him away.

"I see you put Jamie's trousers in the dryer, I think they're done and I want to fold them before they get wrinkled. I tell you what Casey, go make us a couple of drinks and we'll meet back here in a few minutes, OK?"

She gave him a quick kiss and gently bit on his lower lip, something she did when she was really in the mood, then walked off to the laundry room. He got very excited. The outfit, the kiss, her wanting drinks early in the day, all of it told him he was about to get very lucky. She didn't seem pissed off about last night and he guessed she was still turned on from yesterday. He went and made the drinks and when he returned she was sitting on the sofa, folding Jamie's corduroys. Something about seeing his pretty wife in her sexy outfit fondling his best friend's pants made him horny as hell. He handed her a drink and sat in the chair. She laid the green corduroy jeans across her lap and took a sip of her drink. He sat and soaked in the whole picture. Then clearing her throat she spoke in the voice of a teacher correcting a student, pleasant but firm.

"You know Casey, I'm a little pissed off at you right now, you were supposed to lick my pussy last night, but you passed out and left me very horny."

He took a sip. "Yeah I know Karen I'm sorry, you fucked me really hard last night. Don't get me wrong, I'm not complaining or anything, but you just wiped me out."

He gave her a boyish playful grin. "I tell you what though dear, if you want, I'd be happy to crawl under your skirt and make it up to you right now."

She smiled. "That's alright Casey, it'll be taken care of a little later."

He was so horny he didn't realize she wasn't talking about him. "Well then honey, how about maybe letting me have a little fun with your skirt."

She said nothing, her smile disappeared and she went back to folding Jamie's pants.

He sensed her change in mood. "What's the matter Karen?"

She continued to smooth out the trousers for a few seconds, then stopped abruptly.

"Didn't you hear what Audrey told you yesterday? Don't you remember why all your girly clothes are gone and we are sitting here with a pile of Jamie's pants? Did you really think we were just kidding around?"

She paused and looked down at her lap. "I'm sorry Casey, but I'm very disappointed, you said last night that you were going to give this a try, or don't you remember that?"

He was a bit stunned and thought for a minute. "I do remember Karen, but I wasn't sure if it was real or not, I thought you guys were just playing around. I'm sorry."

"Well it was very real Casey." She sighed.

"Then this morning I come in the bedroom to find your penis sticking out of your shorts, and sperm stains over Jamie's trousers. What was I supposed to tell Audrey if she saw your jizzum all over her husband's pants and you haven't even sucked his dick yet? It felt like a slap in the face." She took a sip of her drink and resumed folding the trousers.

He took a long sip himself and thought for a couple of minutes. He realized he had a real problem on his hands, Karen was obviously very serious about all of this stuff. It also sunk into him that there would be no compromise, either he was going to try things her way or there would be a lot of bad blood in the house. He remembered Audrey saying, "don't make her choose between you and me Casey, because you'll lose", and he suddenly feared she might be right. He weighed it all in his mind as he watched her folding Jamie's pants, and she looked so fucking sexy doing it.

He sat up straight and after wincing he said. "Alright Karen I'm sorry, I'll try and take this more seriously, but you're going to have to help me. I mean, I'm trying to figure out what you want me to do, and at the same time you know I have a big problem with Audrey."

He sighed. "Look, I want to make you happy, but I just don't want to get screwed over in the process, understand?"

She stopped folding, then looked at him with a smile. "Yes Casey I do understand, but I think you're forgetting about all the fun you'll be having with Angie. Just remember, you're going to be getting a lot out of this too. I don't know about you getting screwed over, but I know there is a horny tinkerbell next door who is dying to screw you in a sissy corduroy dress."

She let those words hang in the air and she took a sip, maintaining eye contact the whole time. No one spoke for a minute, then Casey broke the silence.

"Can I ask you a question Karen?"

"Of course you can, Casey."

"If I'm only allowed to cum with Jamie's pants, and only when you say so, then why are you wearing that skirt? You know damn well it makes me horny as hell."

She almost giggled, put her drink down and picked up the next pair of trousers to fold. "Yes Casey, I do know what this skirt does to you, and I wore it specifically for that reason. You see dear, I'm teasing your little dickey, and Audrey and I are going to be doing a lot of that in the future."

She paused to fold.

"In fact, over the next three months we'll probably end up having a little contest to see who can give you the most boners."

He stared at her blankly.

"You see Casey, we want you horny all the time, the hornier you are the more you'll want to jerk off with Jamie's corduroys, and in order to play with his pants you need to suck his dick. Hopefully, at some point your brain will make a connection between having corduroy fun and sucking Jamie's dick in his man pants, that's what we're looking for."

They stared at each and Karen didn't flinch. After a long moment she saw a resigned look come over Casey's face. He took a deep breath. "Alright Karen you win, I'll give it a try, but honey I'm horny as hell and I need to cum, can I at least jerk off with the corduroy bathrobe? Please?"

She was extremely happy, but for some reason she didn't want him see that, and maintained an authoritative tone. "No Casey, I'm not letting you have the robe back until I can trust you better. I'm sorry to make it sound that way but it's just the way it is. Besides, I'd think at this point you'd want to save your boners for your all-night fag party with Angie tonight."

His eyes bulged. "Wait, you mean that was for real? I thought that was just more of Audrey's bullshit."

"No Casey it's very real, and it's all set up. We're having dinner with the Hendricks tonight and afterwards Audrey and I will return here to spend the night. Debbie and Angie will stay at their house."

He took a sip and thought for a moment. At first the idea of Audrey spending the night in his bed with his wife sent a pang of jealousy through him, but he rationalized that it was just woman to woman sex so he had nothing to worry about. He also was having a hard time stifling his child-like excitement at the prospect of spending a night with Angie.

He cleared his throat. "Um, are you going to get something for me to wear, how is this going to work?"

She finished smoothing out the black corduroy jeans he came all over yesterday.

"Relax Debbie dear, all your girly stuff is in Jamie's closet, so you can get dressed later. Besides, I have a feeling Angie's looking forward to helping you get dressed, you can stay the way you are for now."

She called him over to the sofa, and they spent the rest of the afternoon making out like teenagers. She teased him unmercifully with her skirt and Jamie's pants, describing all kinds of different ways she was going to use them to make him cum once his training days were over. He could tell she was getting a little turned on too, and she enjoyed him feeling up her tits. At six o'clock she put a stop to everything and they went next door. Casey still had a rock-hard boner that his shorts did little to hide, but his heart was racing with anticipation so he really didn't care.

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

Audrey answered the door and she didn't help his boner situation one bit. She was dressed in a pair of black, high-waisted dress pants and a matching bolero jacket that came to her waist. Both pieces were done in a very plush wide-wale corduroy that looked like it would be heaven to touch. The trousers were belted, had slash pockets, and large cuffs. The Jacket had long sleeves, lapels, and a collar, but no pockets. Underneath she wore a dark pink, ribbed knit blouse that strained to contain her large breasts. Her beautiful red hair was wild and free, cascading down over her shoulders, and she was wearing a pair of red strappy heels. She looks fucking gorgeous and she knew it.

They obviously had no intentions of easing into anything, because when he looked past Audrey he saw Angie already dressed in full drag. He was wearing a pretty red, mid-wale corduroy dress. It had a full pleated skirt that came to mid-calf, short sleeves, a collar, and a cute white corduroy bow on the small breast pocket. It was a casual frock, but a little too formal for a house dress. On his hands he wore a pair of pretty, white, fine-wale corduroy dress gloves. They came about two inches above the wrist and had lace trim with small red bows at the top. They went well with his floppy, white, summer beach hat that also had a bow on its red sash.

Apparently, Angie liked bows.

Below he wore a pair of white tights and red corduroy Toms wedges. With his make-up again looking perfect and his shoulder length blond wig, he looked even prettier than his wife. In fact, all the girls looked wonderful, and he suddenly felt out of place.

Audrey invited them in and after a minute of small talk they sat at the table. She was a pretty good cook and prepared a lovely Italian meal. From the minute he walked in Audrey had been suspiciously civil toward him, on the verge of being nice, but not quite. At times she would put her nose in the air and stared him down, but she always finished it off with an amused smile. The message seemed to be that she was tolerating him for now, but she wasn't done with him.

"Not by a long shot." He vaguely remembered those being the words she used yesterday.

They ate dinner and Casey couldn't keep his eyes off Angie, who for his part was being very shy. The girls did all the talking, passing looks and giggles at each other as they noticed Casey eyeballing Angie. Audrey's dinner was very good, but it took forever. When it was finally over, she told her husband to take Casey into the den and watch a little TV while the girls made coffee. He obeyed.

Casey stood looking at some of the sports memorabilia on the wall, and Angie put something on the TV. A minute later Angie walked over and stood right in front of him. Their faces were only a foot apart and Casey could feel his heart pounding in his chest. Angie reached forward took Casey's hands and they stared into each other's eyes for a moment. He looked so fucking gorgeous that Casey was having a hard time believing it was actually his best friend in that pretty dress. Then without realizing it, desperately trying to say something, Casey said the right thing.

"It just hit me Angie, ever since yesterday I've been trying to think why you look so familiar. I hope you don't mind me saying it, but you look a lot like Patrick Swayze in that movie, To Wong Foo, thanks for everything Julie Newmar. I don't know if you've ever seen it."

Angie's eyes bulged, he smiled and his whole face lit up.

"Oh my god, I can't believe you just said that Debbie, I fucking loved that movie! And Vida has always been sort of a role model of mine. I mean don't get me wrong, Wesley and John were admirable, but Patrick's Vida was just fucking gorgeous! Thank you Debbie, you just made my whole day, I can't wait to"... he put his gloved hands on each side of Casey's face and gently but firmly kissed him.

Casey melted.

The realization that he was swapping tongues with his next-door buddy did cause some confusion, but it didn't last long. Within seconds he let himself be swept away by this beautiful lady, and for the first time in his life he let himself think of a fag as a she rather than a he in a dress. He slid his arms around her waist and brought more passion to the kiss. Finally, after a minute they separated and stared into each other's eyes again.