Casey's Submissive Journey Pt. 13

Mistress Maxine was enjoying his little show too, but for her own reasons. She made him beg for Robin's dick loud and clear, both in his mouth and ass, and she made him feel like a cheap little homo whore in a skirt. Although, she never got mean, in fact she spoke in an almost pleasant tone. She knew what she was making him say was true and she knew that he knew it too. She wasn't angry, she just enjoyed rubbing his nose in the fact that he was a dickless little wimp.

"Alright fag that's enough. Turn around Robin."

He did so quickly and his corduroy covered boner poked Debbie in the face. At that point he was so horny he didn't even wait for Maxi, he just unzipped Robin's pants, pulled out his boner and started jerking him off with his lips. Maxi laughed, she knew she had the faggot right where she wanted him. She even ignored the fact that he didn't ask before sucking Robin's cock, instead she let them enjoy themselves for a few minutes.

He heard the sound of a phone camera snapping off pictures and knew he was being a porn star again. He deciphered what Karen was doing the day before at Mistress Dorothy's house. His wife loved watching guys have sex with each other, so she decided to make her own queer porn videos, and she was going to make her husband be the star. She was sending him to every mistress in the club, one after another, and requesting that the ladies record him being a homo whore for their husbands. When she was done, with help from Audrey, she planned to edit all the clips into several videos for her enjoyment.

He wasn't overly thrilled with the idea, because other than today he wouldn't be allowed to dress or act like a sissy until he'd been a man bitch for everyone in the club, and maybe a few outsiders too. But by then Karen had taken complete control of their marriage, and his sissy balls as well, so there wasn't anything he could do about it. She was now his full-time mistress and she was taking her new role very seriously.

"Alright princess, that's enough. If you thought you were going to suck him off to save your sissy ass you were sorely mistaken. Now take his pants off."

Debbie pulled his mouth off Robin's cock, unbuttoned his trousers and slowly stripped them off. It was another act of humiliation by Maxi. Making him take the pants off the guy who was going to fuck him in the ass, and he imagined that at some point in the future Karen would really enjoy watching him do it.

"If you want Debbie dear, you can lay his trousers on the bed. That way you can rub your face in them while he fucks your sissy pooper."

He liked that, she was being nice.

Still on his knees he turned to face her, kissed her foot and said. "Thank you Mistress, you are very kind."

"I know I am bitch, now move it."

He laid the pants out neatly and knelt down in front of the bed. He then draped himself over them placing his face in the lap of the trousers. Robin must have liked the sight of his ass because he was behind him in an instant. Debbie felt his skirt being pushed on his back, then hands on his hips and something hard against his asshole.

"Wait Robin! Not yet."

Debbie felt something land on his back.

"Use this, I want you to loosen the bitch up, not make him bleed."

Debbie looked back over his shoulder and saw Robin greasing up his cock with some KY jelly. He turned back, buried his face in the pants and waited for what he knew was coming.

It didn't take long.

Without saying a word, Robin popped his mushroom into Debbie's ass and shoved it in about five or six inches. Debbie bit down on the pants and squealed a very un-manly squeal. Robin pulled it all the way out and shoved it back in again, this time right to the balls. Debbie kicked his feet against the floor and continued squealing into the pants. Robin remain still for a minute or so, boner buried to the hilt until Debbie calmed down. He then pulled it all the way out and buried it again, getting the same results. After that he just started fucking really hard, and he didn't seem the least bit concerned whether Debbie liked it or not. Maxi turned on the TV and raised the volume, apparently she wasn't interested in watching the faggots fuck.

Robin wasn't a very imaginative lover and just pounded Debbie's ass without stopping, but once he got past the pain of having his cherry popped, Debbie enjoyed the deep penis poking Robin was giving his rectum. He rubbed his face in the pants and replayed the two blow jobs in his mind as Robin pounded him like a jack hammer. About fifteen minutes later Robin's groans suddenly drowned out the TV, he shoved his dick in right to the balls and collapsed on Debbie's back. With Robin's weight pinning him to the bed he couldn't do anything, so he remained still and tried to relax. He felt a warm sensation deep in his bowels and assumed it was Robin's load, he usually didn't feel that unless a guy really came a ton.

As he laid there he thought. It must be nice to be 19 years-old, getting boner after boner and squirting a big load every time.

Then he smiled. The only thing better than that, is having that 19-year-old shoving his boners in you.

Robin moaned softly as he basked in his afterglow. Debbie rubbed his face in the pants and after a couple of minutes noticed Susan sitting on the cedar chest. When their eyes met she winked and gave him a big smile. She let Robin have a few more minutes of contentment before saying.

"OK sissyboy that's enough afterglow. You've been a good artist's assistant and prepared the canvass nicely, now it is time for the master to paint the picture. This sissy bitch needs a real fucking from a real dick, so you can go."

Debbie felt Robins cock slide out of his rectum leaving it with an empty feeling, and as the picture of Susan's boner flashed through his mind he wished Robin would put it back in. He'd ignored the reality of what was about to happen all day, and now a little panic was setting in.

Susan said. "Lift your face Debbie."

She then grabbed Robin's pants.

"Here sissyboy, put your trousers on and go take a break, you fuck pretty good for a little dick sissy."

Debbie had no idea what to do, and Maxi and Susan completely ignored him as they talked. She hadn't turned the television down and he could only make out parts of their conversation.

After a few minutes, Maxi finally said. "I'm going to ask you again Debbie. Did you clean yourself out today? Because Robin's penis looked a little dirty."

Seeing an opportunity to avoid Susan's dick, he seized it. "Yes Mistress I did, but I did a quick job, maybe I should do it again just to be safe."

Maxi laughed. "I told you dear, I knew the fag wasn't being truthful before. Just relax for a little while and I'll take care of it, it shouldn't take long. Come with me fag, and move it."

Debbie got up, pulled down his skirt and followed his Mistress into the bathroom.

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The bathroom was large and very fancy, and it was all set up for an enema. Something told him she planned on giving him one right from the start. There was a two-gallon enema bag hanging from a hook high on the wall between the shower and the toilet, and it looked full. She ordered Debbie to strip from the waist down and he complied.

Pointing at the shower she said. "Get in fag, let's go."

She then stuck a nozzle up his ass and released the latch, flooding his bowels quickly. After about 30 seconds he started begging for her to stop, and she did. She then let him run to the toilet and relieve himself. His bowels spewed out about a quart of liquid, and there was a slight burn in his rectum. She ordered him right back in the shower and repeated the process, only this time she made him take a little more. The third time she ordered his to stay standing when he ran to the toilet. She then walked over and stood right in front of him. He was holding his bloated belly and had a strained look on his face, which she found quite amusing.

He groaned. "Mistress may I please sit?"

"In a minute fag, first I have something to show you."

She lifted her blouse exposing her tits.

He wasn't expecting that.

They were nice looking breasts with large firm nipples, and even though there was a bit of a sag, for a woman her age he would have expected a lot more.

"Kiss them Debbie, and show me how much you like my titties, then you can relieve yourself."

He leaned forward and kissed her breasts, but kept his arms wrapped around his belly. His bowel situation had become acute. He loved that she was letting him kiss her boobies and suck on her nipples, he just wished his bowels weren't bursting while he did it. After a minute or so he begged to sit again, and seeing that he was on the edge of losing it, she let him. His ass cheeks barely hit the seat before his bowels flooded the toilet.

She stepped forward putting her trousers were right in his face, and when she did he couldn't help himself. He wrapped his arms around her and grabbed her ass while he rubbed his face around the front of her pants. The burn in his rectum made him groan loudly and they remained like until the burn faded to a tingle.

When she shoved the nozzle in the next time, he asked what she was pumping into him, but she simply replied. "None of your business fag."

She filled him up two more times before the bag was empty, stretching his insides in ways he never thought possible. That scared him a little at times, but Maxi seemed to know exactly what she was doing and her confidence and expertise kept him calm. She also appeared to enjoy her work a great deal, which he thought was a little odd. He didn't think she was the kind of woman who would enjoyed bathroom sex.

After forty-five minutes the bag was empty, Debbie's bowels were thoroughly cleaned out and his whole lower abdomen was tingling. He'd also sucked on her titties and kissed her corduroys a few times. So under normal circumstances he'd be a very happy camper. However, these were far from normal circumstances. He knew there was a horny fag out there with a fourteen-inch dick who couldn't wait to shove the whole thing up his ass.

Maxi ordered him to put his stockings and garter belt back on, but not his skirt. She told him to bring that with him. She actually sounded pleasant as she ushered him back into the empty play-room. She told him to fold his skirt up neatly, lay it on the chair and sit on it. There were two fresh drinks on the table between the chairs, a small one for Maxi and a large one for him. He guessed Sonya must have come by and he wondered if she heard him groaning. She told him it would be in his best interest to drink it down and get relaxed, but hearing that actually had the opposite effect. They sipped their drinks for a few minutes and watched the television.

Then, out of the blue, she said. "Drink up dear. I think I may have mentioned it before, but in case I didn't, I'll say it now. My Susan takes it easy on the fags she likes and fucks their bottoms gently, but with fags she doesn't like she just rapes the shit out of them. In your case Debbie dear, I watched her while you were sucking her dick, and I think she likes you a lot." That's all she said and turned her attention back to the TV.

Debbie was relieved to hear that and took a big gulp of his drink. Susan returned and sat on the hope chest. She was smiling like a kid in a candy shop as she stared at him, and her huge dick had turned her dress into the biggest boner tent he'd ever seen.

It was time, and he knew there'd be no escaping his fate.

Even though he was a little scared, to put it mildly, seeing Susan's pretty corduroy dress and knowing she wore it to turn him on excited him tremendously. He then looked at Maxi and thought the same thing about her pants. As he took another big sip, his eyes darted back and forth from one to the other, and in no time at all he had a raging boner.

Maxi said. "Judging from your dress dear, I take it you're ready to fuck your little sissy."

She then looked at Debbie's cock and chuckled.

"I wonder how long that sissy boner is going to last once you pop his cherry."

She was about to say something else but stopped herself and looked at Susan. "Shit! I forgot to lay your corduroys out on the bed."

She looked back at Debbie. "Don't get excited fag, she's not a pervert like you, but she's always liked corduroy and has several pairs of cords."

Maxi texted Sonya and told her to bring the stack of Susan's trousers from their bedroom, and Sonya did as instructed. When she returned Maxi told her to lay the pants out neatly on the bed and she complied. She wasn't the least bit phased by any of the weirdness, and the sight of Susan's tented dress didn't bother her at all. If anything, she looked a little bored, as if she'd seen it all before. She then asks if there would be anything else and Maxi told her no.

As she was leaving she stopped right in front of Debbie, spit on his dick, and said. "Fucking puto." She then shook her head and walked out. It was a very blatant gesture and he thought she should have been fired on the spot, but Maxi didn't seem to mind a bit. In fact, both ladies looked amused.

Maxi told Susan to stand in front of Debbie, and he immediately started kissing her mushroom through her dress. A few minutes later Susan lifted her dress and Debbie sucked her cock and played with her large set of testicles. Based on the huge load he swallowed earlier, he suspected she'd have a big set of balls to match her monstrous cock, and he was right. Her ball sack was the size of a softball and felt firm and full. He guessed he'd be getting another enema, only this time it would be hot sperm through a fourteen-inch nozzle.

Maxi went to the bed and stacked one day pillow on top of another, then laid a couple pairs of Susan's pants over them to soak up any pre-cum. She spaced another pillow out in front of those, and draped three pairs of trousers over it, that's where Debbie's face would be going. Debbie watched her getting Susan's fuck nest ready as he sucked her dick, and it both excited him a little, and scared him a lot. Maxi looked at him with a devilish smile.

"Come over here princess, it's time for you to be my husband's little fuck-bunny."