Casey's Submissive Journey Pt. 02

She noticed he was staring at the bed. "Go take a good look Debbie, that's your corduroy future for the next three months. After tomorrow night, the only corduroys your sissy dick will be allowed to touch will be those right there."

The commanding tone of her voice sent a bit of a shiver down his back. She was beginning to sound a lot like Audrey, but coming from her he liked it. He moved closer to the bed and his eyes were drawn to a pair of green mid-wale jeans. He immediately remembered the day he saw Jamie wearing them because it was the first time he ever wanted to ask another guy if he could suck his dick. They were watching a football game together, like they always do, and Jamie wore those pants and a green corduroy work shirt, he almost looked like he was wearing a uniform. Right from the minute Jamie walked in a half drunk Casey couldn't keep his eyes off of him, and after a few more beers, it got awkward a couple of times when he caught Casey staring at his crotch instead of the game. But he didn't get pissed off, in fact as Casey remembered, he acted like he kind of enjoyed it.

Yes, he remembered that well, because he drank a lot of beer that day and got drunk enough that he almost asked Jamie if he could suck his dick. At one point, his heart was pounding like a jack hammer and the words were sitting on his lips, he was just an impulse away from saying them, but he chickened out. Later on that night Karen walked in on him jerking off with her green corduroy pants and sucking on one of their dildos, and the next day he was hung over and remorseful as hell. He was afraid to face Jamie for a few days, until it sunk into him that Jamie had no idea what he was thinking about that day. As he stood there looking at the green corduroy jeans it gave him an instant boner.

Then, as if reading his mind, Karen said. "Oh by the way, Jamie told me to tell you that he thinks you guys should start off with the green pants, he said you'd know what that meant."

Casey smirked and said he had no idea what he was talking about, but seeing his face turn red, she didn't believe him. Apparently Jamie noticed a lot more that day then he thought.

"Come over here Casey."

She sat up and spread her legs. Pulling his eyes away from the bed he moved closer to her and she motioned him to kneel down. Once on his knees, he put his hands on her thighs and felt up her corduroy clad legs. His face was only about a foot away from her dildo, and it looked even scarier up close. She took hold of it with her right hand and pretended to jerk it off while giving him a teasing smile.

"Do you like my dick Debbie, I asked Audrey to buy me one to use on you, and this is what she picked out."

For some reason that didn't surprise him at all.

"I like it a lot, but it IS awfully big, what do you think sissyboy? She mockingly wiggled it around right in front of his face. She was right, it was fucking huge. It was every bit of twelve inches long and at least two inches thick, and the crown of its mushroom was a lot wider.

"Yes Karen, it's VERY big, I'm thinking maybe too big."

She drooped her lower lip and gave him a sexy pout.

"Oh don't say that Debbie, I've been waiting all day to try it out. You like it when I use Robo-cock on you, and it's not much smaller than this."

Robo-cock was the dildo Casey liked to use when he was very horny, it was about ten inches long, a little slimmer, and it didn't have a big fat mushroom like this one. It got its name one night when they were both pretty drunk and being a little silly.

"I don't know Karen, it looks awfully big."

"Well I tell you what Debbie, I'll loosen you up with Robo-cock first, then I'll fuck you with...we need to come up with a name for my cock. Well anyway, come on fag, let's try it, it'll be fun."

He was genuinely leery of its size, but at the same time, listening to her talk that way was turning him on like crazy. She had never initiated an ass fucking before.

He smiled timidly. "OK Honey, we can give it a try."

"Call me Mistress Karen."

He looked at her blankly.

"I know you're not dressed up but I still want to be your Mistress. Besides you're wearing a girly robe, so that counts."

He was completely shocked by what he was hearing, but he loved it. "Yes Mistress Karen, will you please fuck me in the ass with your big dick?"

She smiled and her whole face lit up. "Well fag, maybe if you kiss it and beg me like a good little wimp".

She pointed it at his face. He hesitated for a moment, but seeing the enthusiastic look on her face he couldn't help himself. He started kissing it all over and begging her to give him a good hard fucking.

After a minute she shocked him again. "Shut up fag, that's enough begging, now suck my dick, I have something I want to tell you."

She was boggling his mind, and he was really starting to get into it. He struggled a bit but got it in his mouth and tried his best to give her a good blow job. He loved sucking dicks, even fake ones.

"OK Debbie, like I said, those pants on the bed, Jamie's pants, they are the only corduroys you're allowed to play with from now on. I'll let you keep the bathrobe and you can wear it around the house, but you're not allowed to jerk off with it. Also, you can't tell Audrey or Jamie about it, got it?"

He nodded as best he could with a mouthful of her dildo. There are seven pairs of corduroys on the bed, one for each day of the week. Once a day, if you want, you can jerk off. You can even kiss that day's pants while you're doing it, but you can't jerk off with them, and you can't cum on them either, do you understand?"

He stopped sucking. "Wait a minute, I thought you said they were the only corduroys I could jerk off with."

She gave him a dirty look. "Did I tell you to stop sucking fag?"

Her tone was sharper then he'd ever heard it before, so he put her dick back in his mouth.

She returned to a more pleasant tone. "As I was saying, if you want to jerk off with a pair of Jamie's pants, then you'll pick out a pair in the morning, and when you come home from work Jamie will be in the living room wearing them. Very simply, you'll unzip his pants, pull out his cock, and give him a blow job. He'll then go home and you'll be allowed to jerk off with his trousers. It's that simple fag, if you want to jerk off with his pants, you suck his cock first. He kept sucking on her dildo, but was now staring at her with disbelief. She just shrugged and gave him a mocking smile.

"Oh well fag, that's your life for the next three months, corduroy and cock, and if you want the former you need to suck the latter. Every time you swallow a load of Jamie's jizzum you'll get to pump a load of sperm on his pants, I think it's a very fair deal for a corduroy sissy like you."

She was enjoying it all a little too much as far as he was concerned, she was even chuckling at times, and he feared that Audrey might be rubbing off on her a little bit more than he liked.

She teased him for several more minutes, then said. "You know what Debbie dear, now that I look at it, my cock really is kinda big. I think maybe you should go give yourself an enema before we start, you know, just to make sure that my cock is the only thing that comes out of your little pooper when I'm done."

He pulled his mouth off the dildo and leaned back on his heels. He was absolutely stunned, he couldn't believe what he just heard and stared at her in awe. It wasn't the suggestion of the enema that shocked him, he often cleaned out his bowels before she fucked him with Robocock, but it was the fact that she made it. She knew what he did, it wasn't a secret, but he usually took care of it privately beforehand. Rarely did they ever even mention it, and here she was suggesting it without a hint of embarrassment.

"Um, OK Karen, I mean Mistress Karen."

"Go ahead Debbie, run along and be a good sissyboy. In fact, make us both another drink first, then go in and take care of business, I'll get the bed ready for my fuck bunny while you're gone."

He got up and did exactly as she instructed, and the whole time he was in the bathroom the anticipation and excitement grew. The more he thought about what already happened that day, and what he hoped was going to happen before the night was over, the hornier he got. It all felt like a dream, and he didn't want to wake up. By the time he finished cleaning himself out, he'd had a hundred fantasies about how she was going to fuck him, and each one was better than the one before it. He just wished he was dressed up, the robe was nice, but it was nothing like being in full drag.

Returning to the bedroom he found her sitting in the chair watching the homos fucking again. He noticed she'd changed things around on the bed, and he had to admit it looked well thought out, her initiative surprised him once more. She had brought in one of the big sofa cushions, positioned it in the middle of the bed and covered it with a few of Jamie's pants, it was obvious she wanted his ass sticking up in the air. A few feet in front of that she had stacked the two bed pillows and covered them with the rest Jamie's corduroys, topping it off with his green corduroy jeans laid out very neatly. He guessed that's what she had in mind for his face. The irony that her setup would make him a proverbial pillow biter was not lost on him, and he wondered if it was intentional.

She looked up at him with a bit of a crooked smile and he noticed her drink was almost empty. Karen was not what you would call a drinker, it didn't take much to get her drunk, and he guessed by then she was pretty well buzzed.

"Hey faggot, I mean Debbie the fag, did you clean out your little bottom for me Tinkerbell?" She giggled, and he knew he was right.

Part of him was afraid she might be too drunk to do it, another part thought it might loosen her up to do it better, and a third part was suddenly afraid of her getting too carried away when she had that fucking monster in his ass.

"Are you OK Karen?"

She finished the last of her drink, put down the glass and stood up, then got right in his face and said sharply. "That's Mistress Karen to you asshole, and don't you fucking question me."

There was just a hint of a slur, but her arrogance made her sound in full control. "Now get your faggot ass on the bed before I kick you in your sissy balls."

He was dumbfounded, no, fuck that, he was shocked to shit. Not sure how to react to her sudden demanding demeanor, he went over and sat on the bed. She followed right behind him, and as soon as he sat down she stuck her dildo in his face.

"Kiss it fag, kiss my fucking dick you little cocksucker."

He didn't argue, and as he kissed and licked her mushroom, he stared down the shaft at the red corduroy jeans he liked so much. Even though he knew very shortly his ass was going to get royally raped, the sight of her sexy corduroys and her display of pure bitchiness, gave him a raging boner.

"That's right Debbie, I said cocksucker, because that's what you are. We both know you want Jamie's dick in your mouth, you've been dreaming about it for a long time you fucking queerboy."

He guessed the alcohol was really kicking in, because her behavior was like nothing he'd ever seen before. She pushed him back a little, grabbed the base of her dildo and wiggled it around in his face.

"Well just remember this pantyboy, his dick isn't as big as mine, he may give you a good fucking, but when Mistress Karen is done with your ass you won't be able to walk for a fucking week." She chuckled. "You know what bitch, get up on the bed, I'm gonna rape your sissy ass right now."

He was horny as hell, and a little scared all at the same time, he had no idea what to expect from her anymore. He stood up and turned around, but before he could climb on the bed she said. "Take off the bathrobe bitch, I don't want it getting in the way."

He did, then got on the bed and positioned himself over the couch cushion. Looking down at the corduroy pants covering the cushion, he got a little excited knowing his boner was going to be humping Jamie's pants while he was getting fucked. He voluntarily laid himself over the cushion, stabbing his dick into his buddy's corduroys, and his face landed on Jamie's green corduroy jeans. He heard her moving around behind him, and then heard the sound of her cell phone camera.

"Reach back and spread your cheeks sissyboy."

"What are you doing Karen?"

"I'm taking pictures of my little tinkerbell, that's what I'm doing. I'm going to send Audrey some before and after pictures, she'll love it. Now spread your cheeks so I can get a good shot of your tight little boy-pussy before I fuck it. Trust me Debbie dear, it's not going to look like that when I'm done."

She took several more pictures before putting her cell phone down. "I've got Robocock all greased up, so keep those fanny cheeks spread nice and wide."

He felt her weight on the bed behind him, and without any fanfare she pressed the knob of the dildo against his asshole. He let go of his ass cheeks, tucked his hands under the pillows and pushed his face into Jamie's pants, anticipating what was coming. Without another word, she roughly popped his cherry and shoved about half the dildo up his rectum. His whole body tensed, he bit into Jamie's corduroys and let out a sissy squeal.

"What's the matter fag, did that hurt? I'm sorry, I didn't realize it would hurt. Let me pull it out and do it again, maybe it won't hurt this time."

She did exactly that, only this time she did it faster, harder and a little deeper. Debbie grunted, groaned and yelled stop into Jamie's pants several times, but in truth he was loving every minute of it. She ignored his protests and did it again, this time ramming the full ten inches up his ass. His cock was grinding into Jamie's corduroys as Karen pinned his ass to the sofa cushion like a bug stuck on a board with a pin.

After giving his rectum a minute to adjust, she said. "Time to loosen up your bottom bitchboy, and oh by the way, you better not leak any sperm on Jamie's pants, if you do there will be hell to pay with Audrey."

They both knew that was impossible, and he loved that she was really getting into it.

She pulled the dildo all the way out and roughly popped it back in, then rammed its full length right to the hilt, causing a few more sissy squeals. After waiting a few seconds, she started giving his ass a hard-slow fucking with about eight inches of Robocock. She continued reaming his rectum for about ten minutes, giving him no breaks, although occasionally she pulled it all the way out and painfully stabbing his asshole with it again, just to keep him on his toes. She was doing an excellent job and he wondered if she'd been coached by Audrey, her previous fuckings had never been this good. She continued raping his shitter, and just when he reached that point where the pain had dissipated and all that was left was the wonderful feeling of being fucked, she stopped and abruptly pulled the dildo out.

He let out a grunt, opened his eyes, and seeing Jamie's corduroys turned him on a lot. He rubbed his face all around them, actually cooing a little at the realization of what he was doing. His ass felt wonderful, it was stretched, empty and ready to be fucked again. He started humping his dick against his buddy's pants, and he was sure by now he was leaking jizzum all over them, and that gave him a perverse thrill. He heard the camera noise again, felt her fingers pry his ass cheeks apart, and he was totally blown away by how much she was getting into all of it.

"Stop fucking Jamie's pants tinkerbell, or I'll spank your fairy ass."

He was tempted to disobey and see how far she would go, but she was doing so well he didn't want to chance fucking things up, so he stopped. She snapped off a few more pictures and got up off the bed.

"If I were you Debbie dear, I'd be thinking about where I was going to buy a new rectum, because after I send these pictures to Audrey I'm going to use my big dick to destroy your little pooper. Yes Daisy May, I'm gonna fuck the living shit out of your boy pussy, you'll be so stretched you'll be shitting in your pants for a week."

Casey couldn't believe his ears, he was so fucking turned on he thought he was going to explode. He buried his face in the corduroys jeans again and started fucking Jamie's pants, and this time he didn't care if she beat his ass or not. After a few minutes he felt her weight on the bed behind him, and his heart started beating faster in anticipation.

She nudged his legs apart and positioned herself between them. "Better bite your buddy's man pants homo, cause here it comes."

Grabbing his hips, she pulled his ass back toward her and pressed the huge mushroom of her dildo into his bottom. He could feel it slip around between his cheeks before she found his boy-pussy, and he was grateful that she had greased it up good. She pushed the mushroom against his anus until it was stretched about half way and stopped, that caused a little squeal into the corduroys.

"Do you want me to go easy on your ass faggot?"

He nodded vigorously without removing his face from the pants.

"Well then sissyboy, you better beg me to fuck you really hard, maybe if you do a good job, I just might take it easy on you."

He was in fag heaven. "Please Mistress Karen rape me, please fuck me so hard I won't be able to walk, make me you bitch please Mistress, I need you to own my ass, please turn me into your fuck toy."

He went on like that for a few more minutes, and Karen was surprised by how much hearing it turned her on. The alcohol was helping with her courage, but hearing her sissy begging for it took it up a notch, now she felt like fucking his ass whether he wanted it or not. Finally she'd heard enough, and without any warning just roughly popped the mushroom all the way in.

He yelped loudly. "No-no-no please stop!"

She grabbed the back of his head and pushed his face into Jamie's pants, muffling his bitching. After a minute, he relaxed a little and she let go of his head. Putting her hands back on his hips, she pulled her big fat mushroom out and rammed it right back in again. That brought on another round of sissy squeals, but this time he kept his face in the corduroys, muffling himself.

"Are you liking my dick fag?"

She got no answer, so she pulled it out and popped it in again.

"Answer me fag, do you like my cock?"

He again squealed, but this time he nodded and she heard a faint, "uh-huh."

"Good, then I'll let you get to know it a little better."

She shoved it in about 8 inches in one thrust. He grunted loudly into the pants and at the same time thumped his feet up and down against the bed.

"Oh knock it off Daisy May, I haven't even started banging your ass yet and you already sound like a fucking pansy."

He was now convinced she'd been well coached by Audrey, that wasn't coming from his Karen. But he wasn't complaining, in fact, he loved every word. Unfortunately for him, Karen had played out her mentally rehearsed bitch act, so she decided to just get things moving. She pulled the dildo back a few inches and then buried it in her husband's ass. Debbie half screamed, half squealed into the corduroy pants, and his feet did the thumping thing even faster. He'd never had his rectum stretched that much before, and he thought her dick was going to come bursting through his belly button. She paused a few seconds to make sure she didn't hurt him, and when his carrying on didn't appear to be more than a sissy bitch act, she pulled it back about ten inches and sent it home again. That brought on more grunting and thumping, and after he calmed a bit his face turned sideways on the pants and she heard him say breathlessly, "no more, no more, no more."