Casey's Submissive Journey Pt. 15

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Mistress Maxi - Part 4.
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Part 15 of the 15 part series

Updated 06/08/2023
Created 12/03/2017
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When he walked into the playroom he saw Robin sitting in one of the chairs drinking a beer. Sonya turned around and pointed to the other chair. "Sit puto."

Debbie did as told and his boner made a very obvious tent out of his skirt, it didn't bother him though because it matched Robin's pants. Sonya left without a word and Debbie picked up the drink on the table next to him, taking a big sip. They sat in silence for several minutes and Debbie like it when Robin started rubbing his boner though his pants as he ogled him. For his part Debbie couldn't keep his eyes off Robin's corduroy outfit, and the video of the guy jerking off kept playing over and over in his mind. He was now absolutely certain that Karen had arranged it, and he hoped he'd get to watch Robin jerk off just like the guy in the video. He also snuck a few peaks at Robin's face, and aside from liking the look of lust on it, he enjoyed the fact that he was a young prettyboy. He was obvious a sissyfag who just happened to dressed up masculine. Debbie guessed that if given a choice he'd much rather be in a dress.

You never see the face of the guy in the video, but judging from his hands Debbie guessed he was an older guy. And as much as he liked the video, he liked having a young pantyboy in the outfit instead. It was one of those rare times when reality was better than the fantasy.

It was kind of awkward with nothing being said, but the air was so charged with sexual electricity that nothing needed to be said. After about ten minutes Maxi appeared in the doorway with her arms folded across her chest, staring at the two of them as if they were naughty boys.

"How pathetic you fags are, you've got no balls whatsoever. I'm serious, between the two of you there are four completely useless testicles in this room."

She sighed deeply.

"Well anyway. Something's come up and I must attend to some business, in the mean time I want you to suck Robin's cock again. Now that you're done with dinner I'm sure he has a nice big load of jizzum for your dessert. I'll be back shortly, so get busy, you've got a lot more whoring to do before this evening is over."

She disappeared and Debbie wondered how many more times she planned on making him be a cock-whore. He'd already had a half dozen loads of sperm pumped in him and he was about to get another. He wasn't complaining though, he liked the idea of another rendezvous with Robin's corduroys.

Robin had a big smile on his face. "Get over here and suck my dick fag, I'm going to fuck your mouth all night long."

He was attempting to sound forceful but his voice confirmed Debbie's suspicions, he was a wimpy sissy. Debbie just stared at him.

"Move it fag, or I'll fuck you in the ass instead."

"Knock it off Robin, I'm twice your age and don't want to hear any more of your bullshit. Now if you get a better attitude I'd be happy to suck you off."

Robin was shocked and confused. "But, but you can't do that, I'm in charge. I'll tell Maxi and she'll make you be my bitch."

He was right of course, but Debbie wasn't going to let that be the end of it.

"Let me explain something to you wimp, you aren't even in the club yet. Before you ever get the chance to have me as your bitch, you'll be my bitch several times. Just because you lucked out today and are getting to be Maxi's fair haired boy, doesn't change the fact that you're low bitch on the totem pole once they vote your wife in. If I were you sissyboy, I'd be trying to make friends with the other fags real quick."

He looked like he wanted to say something but stayed quiet.

"You'll be Susan's bitch too faggot, very soon, getting your ass fucked just like me, and being young and pretty she'll want to do you a lot."

Actually, Debbie feared that if anyone was in danger of that it was him. Both Maxi and Susan seemed to have taken a shine to him, but he kept that to himself.

"You'll find out pretty soon Robin, that even though we may do whatever the ladies tell us to do, and sometimes that means being nasty to another fag, for the most part we all try to help each other out when we can."

Robin seemed to lose whatever bravado he had, and noticing the cameras it dawned on Debbie that he probably just fucked up a blow job scene for Karen, but he shrugged it off and hoped his wife would understand. He took a sip of his drink, put it down and knelt in front of Robin. He then smiled at him, and that seemed to relax him a bit. Debbie reached up and started rubbing his boner through his trousers. The feeling of the hard dick in the soft corduroys sent a jolt of excitement through him that went straight down to his own sissy penis.

He then spent several minutes feeling up Robin's outfit and rubbing his face all around his belly and lap. He didn't care about anything else, he just wanted to make love to Robin's corduroys. He spent most of his time humping his face against his boner, kissing and nibbling it through his pants. As he was enjoying his time in corduroy fag heaven his mind began to wander.

He decided to ask Karen if she would get matching outfits like Robin's for him and Jamie to wear on a Homo Hubby Night, maybe do it as a reward. He fantasized about them kissing and groping each other in those outfits for a long time, taking turns playing with each other's cocks though their pants and generally getting each other horny as hell. Then he pictured the girls ordering them to pull their cocks out and lay down on the bed in a sixty-nine. They would grope each other's corduroy covered asses and suck each other's cocks for a long time.

Debbie then had another weird thought in the middle of his fantasy, he often got weird ideas when he was horny. He thought about him and Jamie becoming a sperm recycling machine, a living circular jizzum pump. The sperm would be pumped out of Jamie's ball sack, down his throat and into his belly. Then it would go down into his ball sack and be pumped into Jamie's mouth, down his throat and into his belly and ball sack, just to be pumped back into Casey's mouth. They would keep sucking the jizzum out of each other's dicks just to pump it back into each other's mouths for hours. Maybe they could get a patent for being a perpetual motion jizzum recycler.

He knew it was a weird idea, but he was horny as hell.

In fact, Debbie made himself so horny with Robin's outfit that he wanted a mouthful of sperm, and he wanted it right away. He went straight into full cocksucking mode. He unzipped Robin's pants, pulled out his cock and immediately started jerking him of with his lips. His head was bobbing up and down in Robin's lap like he was possessed, faster and faster, and after only a few minutes Robin was moaning and stroking Debbie's shoulders. A few minutes after that he started pumping Debbie's mouth full of Jizzum just as Maxi walked through the door. Debbie stayed with him and managed to swallow his whole load balls to belly. When Robin collapsed in the chair after his orgasm, Debbie laid his face in his lap and rested. As he did he heard Maxi slowly clapping approval.

"Robin looks very pleased, I'd say you're a very good cocksucker Debbie dear. I'm beginning to like you as Susan's bitch more and more."

That wasn't exactly what Debbie wanted to hear, and he realized his corduroy obsession was causing him to dig his own grave.

She put on the TV and gave the fags a couple of minutes to rest, then said. "Alright Robin you've been a very good boy so far, and you'll be cumming at least one more time before the night is over, but for now you can go rest. Debbie, let Robin up."

Debbie sat back on his heels and watched Robin zip up his pants, and once again the sound made him feel like a cheap whore.

Robin looked at Maxi. "Go ahead dear, I'll be summoning for you on an hour or two."

He gave Debbie a snotty look that said, "I told you I own you", then he left.

"Sit up in the chair fag."

Debbie obeyed and asked if he could sip his drink, Maxi nodded. She then informed him that Susan would be in shortly to fuck him again. Sonya returned with a drink for her and they sat for a few minutes sipping their drinks in silence.

He didn't know what she was thinking about as she watched the financial report with the sound off, but he knew what was on his mind, a mixture of apprehension and horniness. The idea of being fucked by Susan was looming large. He knew he'd survived the last one unscathed, but with her huge cock he also knew his rectum would be in danger whenever she fucked him. No one's ass was designed to handle a monstrous cock like hers. But as he fretted over Susan's cock he also kept staring at Maxi's red corduroy trousers, they looked sexier than her blue ones. They were pleated, high-waisted, had slash pockets and cuffs. The fabric was a mid-wale, but a heavier mid-wale than the blue ones, and they looked wonderful. He couldn't stop fantasizing about rubbing his boner against them.

She suddenly turned and caught him staring at her pants. She looked slightly annoyed.

"Stop staring at my trousers fag, and look at me."

He did.

"I'm very pleased with your behavior so far Debbie, and Susan and I have been talking. We've decided that after your wife is done running her slow train on you, I'll be instructing Karen to send you around on a regular basis. If you continue to behave and play your cards right, you just might find yourself receiving a lot of corduroy rewards in the process. I have the means to make all your sissy little corduroy fantasies come true if I choose to, so just keep that in mind tinkerbell."

She stopped herself and chuckled.

"I just realized what that must've sounded like. Don't get the wrong idea fag, I'm not trying to steal you away from Karen, that won't be happening. You see dear, you have a pathetic little penis, so I have no use for you other than as a pussy licker and a whore for my Susan's dick. I just want you to know that I'm a very fair and rewarding mistress with deserving fags.

Besides, I must admit, I find this whole corduroy business rather amusing. The idea that someone could get sexually excited by corduroy is a little astounding, but I guess it just proves that perversion knows no limits. I'll also admit that I like the idea you're such a slave to your fetish, it makes you all the more easier to control.

So, what do you think fag, do you like the idea of being our whore?"

Casey wasn't exactly thrilled by the news. He liked the idea of getting to be Debbie when he was at Maxi's, and getting corduroy rewards certainly sounded good, but he wasn't sure his ass could handle a steady diet of Susan's monstrous cock. He was also afraid it would wipe him out so much he wouldn't be able to have sex with anyone else in between. But like anything else since Karen became his full-time Mistress, he'd just have to take in one step at a time.

Before Debbie could respond Susan walking in and sat on the hope chest, interrupting their conversation. She looked very happy and her new skirt was tenting in a way that told him she was very horny as well. He liked her new outfit and thought she looked very sexy, but her huge cock was making him anxious again. The skirt was long, full and made with a very plush wide-wale corduroy. It was dark pink, pleated, and had no pockets or detailing. On top, she was wearing a black halter top and a pink scarf made of a soft looking fine-wale corduroy. And even though the fabric of her skirt was heavy, her fourteen-inch tent pole pushed it out like it was tissue paper.

She had a drink and was sipping at it as Maxi explained what they were discussing. She seemed very enthusiastic about the idea of Debbie being their whore, and ogled him lecherously. She was having so much fun that at one point she bent over and kissed her corduroy covered mushroom, winking at him while she did. He knew it was meant as a mock and a taunt, but in truth, seeing her do it turned him on a lot. The fact that she did it with such ease convinced him that she could indeed suck her own cock, and that was something he would love to see. Susan's distraction got him off the hook from having to answer Maxi's question, for which Debbie was grateful, and she replaced it with one he didn't mind answering at all.

"Do you like Susan's outfit Debbie?"

"Yes Mistress very much, she looks very beautiful."

"She bought it last night at Lord and Taylor just so she could wear it for you fag, so you damn well better appreciate it."

"I do Mistress. Miss Susan you look lovely, thank you so much for even thinking about me, I hope I've brought you as much pleasure as you've given me."

Susan gave him a smile, raised her glass and puckered a kiss at him. By then he wasn't sure if she was mocking him or genuinely felt affection for him.

Maxi said. "If you'd like you can have a little fun with her skirt for a few minutes, but you'd better hurry because she'll be fucking you sissy ass very soon."

"Thank you Mistress, you are very kind."

He took a quick gulp of his drink, then scurried over and knelt in front of Susan. She sat back and let him rub his face all around the front of her skirt and kiss her tent pole for a bit, and Debbie loved every second, the fabric felt wonderful.

Suddenly she said, "Back off fag", then pulled her skirt up on her belly. Her cock was as hard as a rock and Debbie didn't need any instructions. He sucked her dick slowly and teasingly with a lot of moaning and licking. There was no hurry, he knew she had no intentions of cumming in his mouth, so he just tried to give her a very sexy sucking. It must have worked because after only a few minutes she pushed him back and told him to get on his feet. She stood too, and both fags took off their skirts. Maxi had laid out one of the day pillows at the end of the bed and Debbie wasn't sure how he was supposed drape himself over it. He looked at her puzzled.

"On your back fag, with your ass on the pillow, Susan wants to fuck you face to face."

He climbed on the bed and positioned himself as instructed, and Maxi threw several pairs of Susan's corduroy pants on his face and chest. "Here dear, you can play with them while Susan is having her fun."

Debbie started rubbing his face with a pair as he watched Susan grease up her cock right down to her balls, it was obvious she had every intention of shoving the whole thing in again. Maxi sat next to him on the bed, slowly ran her hand over his tits and said. "Time for you to be a good little bitch again Debbie, Susan even gave herself a little extra grease just for you."

Susan got between his legs, pressed her fat mushroom against his asshole, and Maxi said. "Now pucker up your boy-pussy and make my girl feel really good."

Susan wrapped her thumb and forefinger around the top of his ball sack and squeezed tightly, forcing his balls to stick straight up, then giving them an upward yank he lifted his ass a little. She smiled, puckered a kiss at him and said. "You're mine now baby-doll."

She shoved her mushroom in along with six inches of hard cock. Her fat knob popped his cherry without mercy and even though he was looser than before it still hurt like hell, but with her iron grip on his balls he could do nothing about it. She waited about ten seconds then pulled it out and popped it right back in again. Debbie stuffed her pants in his mouth and squealed.

Maxi said. "There-there baby, calm down, be a big girl for Susan."

She popped her mushroom in and out several more times while smiling and taunting him, and when he finally stopped squealing she let go of his balls and started fucking him with about ten inches. She settled into a slow steady pace and he could see the look of pleasure on her face. She was in no hurry, she was going to take her time. She was going to fuck him as long and deep as she could and love every minute of it.

After a few minutes Maxi said. "That's a good girl." Then began massaging his belly.

"Damn girl, I can feel your cock in his tummy, this bitch was made for you dear."

Debbie didn't like hearing that.

Susan began playing with Debbie's dick as she fucked him, and after a while he got hard. She then started jerking him off in earnest and it felt so good he started moaning. Hearing that, Maxi pulled the pants away from his face, grabbed the back of his neck and forced his face toward his cock, leaving it about six inches away. With Susan's fat cock preventing his asshole from clenching and her knob pounding his prostate, he had no control of his dick. She was pointing it right at his face and there was nothing he could do about it. Maxi ordered him to open his mouth and a minute later he emptied his ball sack in his mouth and all over his face.

When his dick stopped squirting and his face was covered with sperm Maxi let him lie back on the bed. Susan continued reaming his rectum, by then she was giving him a steady twelve inches. Maxi started scooping up globs of jizzum from his face and feeding it to him, making him lick her fingers clean after each scoop. She smiled, took her time and seemed thoroughly amused by what she was doing, like she was feeding a baby. Debbie was spent from his orgasm and losing his strength quickly from the raping, but even so, he enjoyed the attention Maxi was giving him. When she was finished, she wiped her fingers on a pair of Susan's pants and threw them over his face. Her voice lost it sweetness and she said.

"Go ahead dear, finish the bitch off."

Obeying his wife, Susan stuck a full twelve inches in him and just held it there for a minute until he relaxed. She then forced in another inch and Maxi shoved the pants in his mouth in response to his squealing. In the same manner as before, she worked her knob in and out for a while until his was taking a full thirteen inches without squealing, she then repeated the process until all fourteen inches are buried to the hilt. By then he was completely paralyzed, and for the next twenty minutes she fucked the shit out of him.

Lying on his back the feeling of her mushroom being in his belly was even more pronounced, and it was further enhanced when Maxi massaged it.

"I don't believe it dear, your cock is in the bitch's tummy, I don't know how you did it but I can feel it in there."

Susan stared at Debbie with a devilish look and just shrugged, she was focused on giving his ass every inch she could, and there was nothing he could do about it. His legs were perched on her shoulders and no longer had any strength. She finally started pounding his ass really hard while grunting and groaning, then squirted another huge load of jizzum deep in his belly. She collapses on top of him squeezing his balls a bit, but by then he couldn't move or even object, he was nothing but a rag doll.

Her face was just inches from his and he could feel her hot breath as she panted out the last of her orgasm. A few minutes later, after catching her breath, she kisses him passionately for a long time. He eventually mustered enough strength to reciprocate, but barely, he was totally paralyzed and her monstrous dick was still inside him. When she was done probing his mouth with her tongue she stood up, took a deep breath and slowly pulled her semi-hard sausage all the way out of his ass. It was followed by a long fart, which caused the ladies to chuckle.

They stood over him and discussed what to do next. Susan tried to talk Maxi into strapping on a really big dildo, but she declined, she said it wouldn't be worth it. Debbie was so paralyzed she wouldn't even get a squeal out of him, she would save that for another day. Eventually, without even a "how are you doing Debbie", the two ladies left. Susan went to the bathroom to clean up and Maxi simply walked out.

With great effort Debbie slid up the bed a little taking his ass off the pillow and remained motionless, trying to recuperate. His insides were thoroughly gutted and he had no feeling or control over his asshole, he could have been shitting all over the bed for all he knew, although he hoped that wasn't the case. Eventually Susan returned, smiled at him and put her skirt back on. And even though she had just cum for the third time and her dick was limp, her skirt still had a bulge in it. She looked completely satisfied, like the cat that just ate the canary. She bent over, kissed him and wiggled his limp little dickie around.

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