Jennifer Monroe & the Ladies Ch. 01

Personally bitchboy, I don't think giving her a pair of sperm stained jeans will help your cause at all. So get to it fag."

He did as told and they both knew he was loving every minute of it. He wasn't even worried about the punishment he knew was coming, he suspected the night would be well worth it. As he sucked on the corduroys he suddenly felt fingers on his naked thigh. Someone was scooping up all the pre-cum dripping down his leg. He looked back over his shoulder and saw Sasha slowly licking her fingers clean. She was a pretty black girl, slender with large thick lips, and her make-up and blond wig made her look like she was about thirty. He suspected she was older than that though. She wore a yellow and black striped sweater over her medium sized titties, a burgundy, knee length, mid-wale corduroy skirt, seamed stockings and black pumps. She was very sexy, and the idea that she had a black cock under her corduroy skirt gave Debbie a boner in a matter of seconds. Seeing that, Sasha's smiled and she started playing with his sissy balls.

As he performed his task he shut his eyes and enjoyed the taste, he even purred a bit as he savored the feeling of the buttplug stretching his rectum and Sasha's experienced fingers diddling his balls. At one point however, Sasha gave his nuts a playful yank, and that caused him to open his eyes.

When he did he was looking right at Mrs. Monroe, and as Sasha slowly stroked his boner he watched his kneeling mistress suck Lesley's cock like a cheap whore. He'd never seen her do that before, and she certainly seemed to like what she was doing. It looked so strange to see her being submissive to a cock, especially when dressed in her tough bitch corduroy outfit, she was usually a very nasty fag fucker when dressed in that manly uniform.

He stared at the rough corduroy jeans she was wearing, and he remembered the day she caught him jerking off with them. She was so fucking furious that he shot his sperm all over her pants that she abused the shit out of his sorry ass for a week, but to him it was worth every minute. Although now, seeing her on her knees sucking Lesley's cock he had a sudden urge to cut a hole in her jeans and fuck her ass right through her corduroys. He'd never felt like that before. For the first time he saw Mrs. Monroe as a slutty bitch to fuck rather than a Mistress to worship, and fucking her in her manly corduroy uniform made it seem even more exciting. He toyed with the idea for a minute but quickly dismissed it, he knew he would never have the balls to stand up to her. His thoughts were interrupted by the voice of Jennifer.

"Sasha dear, you'd better suck your virgin before the bitch squirts all over the floor."

Sasha looked at the leaking pre-cum. "Oh shit Jen you're right, stand up bitch."

He complied and she gently pushed him back into and armchair. She positioned herself between his legs and smiling broadly as she stared at his boner, then licked the pre-cum from his mushroom.

"Come on Daisy May, time to give Sasha some sugar."

Debbie kept sucking on the pants and watched Sasha take his knob in her pretty mouth, then after a few seconds she started sliding her big black lips up and down his hard cock. He was in fucking heaven, but it was Sasha who was doing all the moaning. She was obviously loving every minute of having a virgin little white-boy dickie sliding between her hungry lips. He was sure it wouldn't be long before she was ramming her black cock in his tight white pussy, but for the moment he loved watching his sissy dick disappear into her pretty face.

He glanced down her back at the corduroy skirt covering her sexy round ass, and it was all getting to be too much. Part of him wanted to hump her ass and cum all over her skirt, yet another part wanted to lift her skirt and fuck her pooper. He wasn't sure why he was suddenly having all these boy thoughts. However Sasha's mouth distracted him, she was sucking an orgasm straight out of his ball sack, and the idea that he was actually going to cum in somebody's mouth sent him over the edge. He grunted loudly into the pants, which was music to Sasha's ears, she was dying for a mouthful of virgin fag sperm, and Debbie's tasty little dickie did not disappoint her.

His orgasm was very intense, and he couldn't believe he was actually cumming in Sasha's mouth. She moaned with pleasure as she gulped down each mouthful of jizzum and used her large lips to stroke out some more, she had obviously done this many times before. She massaged his sissy balls coaxing out every last drop of sperm, and Debbie squealed into his mouthful of corduroy, loving every second of it. Once his orgasm subsided and his ball sack was drained, his body went completely limp. She continued to savor the taste of his sissy dick until it turned into a limp little fag noodle.

She wasn't done with him though, and moved down to kiss and lick his girly balls. Looking down he could see the lust in her pretty eyes as she stared back up at him, and reality began to set in. He guessed she probably had boner under her corduroy skirt and was going to shove it up his ass very shortly.

Debbie had never seen a real black dick before, and the thought of being fucked by one was actually rather exciting. In fact, as he watched her lips nibbling on his balls he thought about the big black dicks he'd seen in the porno videos. Those thoughts made him so excited that he couldn't control himself, and he asked. "Sasha can I please suck your dick, will you please fuck me with your big black cock?"

The whole room went silent for a few seconds, then they all began to giggle like school girls, and Jennifer said. "Well that didn't take long. It looks like Sasha's magic mouth has struck again. Yes, I think our little sissyboy is in the right frame of mind. Shall we get started ladies?"

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They all chatted excitedly, and the primal lust in the room was so thick you could cut it with a knife.

Jennifer spoke. "Alright ladies calm down, I know it's been a while since we had a bitch to play with, but Wanda assures me that sissyboy here can go the distance. So there's no need to worry, no one will be left out, we'll all get ample use of both ends of our little bitch. And as we just saw Debbie is quite the sperm whore so none of our jizzum will go to waste.

Now, the way I see it we have three choices, because I don't want another fucking free for all orgy like the one that that ruined our last sissyboy. We can all cum in his mouth first, or we can begin by fucking his bottom. Or, if you prefer, we could fuck both ends at the same time if we do it in an orderly fashion."

As the ladies discussed the finer points of fucking their fag, Sasha got to her feet. She pulled up her skirt, grabbed her big black cock at its base and wiggled it around in front of him.

"Have you ever had dark meat sugar?"

He stared at it with lust, it was about ten inches long with a large perfectly shaped mushroom. It started out very dark at its base, but about halfway up it lightened into a tan color.

He shook his head slowly.

"I didn't think so fag. I bet a suburban white boy like you has never even seen a black dick before, have you sugar?"

"No miss Sasha, never."

"But you want it don't you Debbie? You wanna know what a real black cock feels like in your ass instead of these little white dicks, right fag?"

He nodded, licked his lips and just kept staring at it.

Jennifer stopped in mid-sentence. "What did you just say Sasha? I don't think I heard you right."

Without even looking back at her, Sasha said loudly. "That is, except for Miss Jennifer of course."

"That's better dear." She returned to her conversation.

Sasha leaned her face into Debbie's and whispered. "Don't you worry sugar, after these white ladies get done poking you with their little peckers, Sasha's gonna to teach you about big black cock, and what real fucking's all about."

She then gave Debbie a long passionate kiss, probing his mouth with her artful tongue, and Debbie reached up and grabbed her boner through her corduroy skirt. The feeling of a big cock wrapped in corduroy thrilled him to no end, and the thought that very shortly she would be shoving her huge dick up his pooper caused him to give a throaty moan into Sasha's mouth. He continued to stroke her cock through her corduroy skirt until she started moaning back, and after another minute she pulled his hand away, lifted her skirt and replaced his hand on her naked cock.

She resumed kissing him again and they stayed like that for several minutes until she went over the edge. Her boner swelled and pulsed in his hand right before he felt the warm pleasant feeling of Sasha's sperm splattering into his neck and all over his blouse. She was breathing hard through her nose and groaned with pleasure but never broke their kiss. She emptied her ball sack, coating his blouse, cock and balls with her warm fag sperm. Debbie continued to stroke her boner until it went limp and they broke their kiss. He reveled in the feeling that he could make her cum, he loved pleasuring ladies, whether they have a cock or a pussy didn't matter to him.

Pulling her face back slightly she looked into Debbie's eyes and said. "Oh sugar, that felt so fucking good!"

She reached down and scooped up a big glob of jizzum off of Debbie's tits, then with a big smile she shoved it in her mouth and licked her fingers clean. She then scooped up another glob and held her fingers in front of his face.

"Open up sugar, nothing tastes better than sweet girly sperm, especially when it's pumped out of Sasha's big ball sack, know what I mean sissyboy?"

He nodded, opened his mouth wide and eagerly stuck out his tongue. She chuckled. "Oh sissyboy, you really want Sasha's cum don't you you little bitch, well here you go sugar."

She wiped it on Debbie's tongue, and her thick cream just sat there as Debbie stared at her. "Well go ahead fag, you have my permission, eat it."

He swallowed it quickly, smiled at her and she held her fingers in front of his lips. "Very good my little fag puppy, now lick them clean."

After he did, she straightened up, smoothed out her skirt and put her hands on her hips. "Look at you Daisy may, you're a fucking mess, do you always sit around covered in another girl's jizzum?"

He slowly shook his head and she noticed his sperm coated dickie was half hard. "Well, what do you think fag, should I lick your sissy little cock clean? It is my mess after all, so I guess I should be the one to clean it up."

As she knelt down in front of him Jennifer said. "Don't even fucking think about it Sasha. You got your prize, you even got a hand job to hold you over, now it's time for the rest of us to start our party with the little bitch. Plus, I don't want him cumming again, he's getting way too many rewards too soon, he hasn't even earned anything yet. Now take Wanda's pants and wipe your sperm off the bitch, and do a good job, I'm going to put him in a dress for the rest of the night, and I want him clean to start with."

Sasha shrugged in resignation. "Whatever you say boss."

She picking up the corduroy jeans, which look spotless. "Hey Jen, didn't tinkerbell just lick these pants clean so Wanda wouldn't cut his balls off?"

"That's Debbie's problem Sasha, not yours, just clean the bitch up."

She said, "OK", and started mopping up her jizzum with the trousers. When she got to his cock, she spent a little extra time giving his dickie a good rubbing, and he seemed to like that a lot, but she quickly moved on when he started moaning.

When done, she asked. "What do you want me to do with these Jen?"

"Give them to my wife."

She then turned to Wanda, who was done sucking Lesley. "Sorry dear, I guess you're just going to have to punish your fag when we're done with his sissy ass."

She took the trousers from Sasha, gave Jennifer a kiss and said thank you. Then after giving Debbie a very nasty sneer, she said good night to all the ladies and left. Looking back at Sasha, Jennifer said. "Alright Sasha, bring the bitch over here, it's time for the party to start."

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Sasha led Debbie in front of Miss Jennifer and told him to kneel, then took a seat with the other ladies. Jennifer leaned forward in her chair, cupped her hand under his chin, lifted his face to hers and stared into his eyes.

"Now you listen to me Debbie dear, and listen good. You are about to become our Lady's Club bitch, do you understand what that means?"

He nodded slowly.

"That won't do faggot, answer me!"

"Yes Miss Jennifer, I'm your bitch, please make me your fuck toy please."

She glanced at the ladies and smiled with pride, it felt so good to have a pretty little bitchboy to play with again. She looking back at him. "Now faggot, I want to make sure you know what you are getting into, so listen up. I, your Miss Jennifer, and all the rest of the ladies are your queens. You, Debbie Dear, are a piece of cocksucking fag shit. Got it Daisy May pantyboy?"

"Yes Miss Jennifer, I do."

"Your queens have dressed themselves in these frumpy corduroy outfits as a favor to Mrs. Monroe, so you damn well better appreciate it bitchboy. From this moment on, you are here for no other reason than to worship your queens, in any fucking way you possibly can. Got it Dearie?"

"Yes Miss Jennifer."

"Until further notice, your only purpose in life is to worship their cocks. You're not here for pleasure, in fact you won't cum again unless I, your Miss Jennifer, say you can, and to make sure of it, your little dickie will be caged for the rest of the night."

She let go of his face and told him to stand, then reached over the arm of the chair and came up with chastity device. After spitting in the cock cage several times to lube it up, she grabbed his now limp penis in one hand and slid it on with the other, then locked it in place.

"That's right bitchboy, no more boners for you unless you earn them by being a good little whore." She then slapped his caged penis, causing him to yelp like a puppy.

She waited a moment for him to recover. "Are you ready to go on Daisy May?"

"Yes Ma'am, please."

"Alright then Debbie dear, you are going to use your hands, your face, your mouth, your pooper, or whatever other part of you the ladies want to service them. They will pump their jizzum in your mouth and ass, or maybe cum all over you instead, but whatever they do you will swallow every fucking drop of sperm that is ejaculated in this room from now on. Even if the ladies suck or fuck one another, they will either spit it in your mouth or you will shove your tongue up the lady's ass and suck the sperm out of her rectum. You will be pissed on, maybe even in your mouth, and you might receive a piss enema."

She paused. "Let me see, am I forgetting anything ladies?"

"Punishment." Lesley said.

"Yes dear, thanks for reminding me."

"If you at any time misbehave or refuse to do something, you will be spanked in front of everyone, and trust me Debbie dear it won't tickle. And if you continue to misbehave or you deliberately piss anyone off, you will be thrown out, never to return, not even to your mistress. Your opportunity to live out all your sissy corduroy fantasies will be history. Do you understand me sissyboy?"

He whispered. "Yes Miss Jennifer."

"Is that what you want, to be thrown out of a roomful of corduroy clad queens, to have your ultimate fantasy taken away?"

"God no Miss Jennifer, I'll be good, I'll do anything you want me to do, please let me be your bitch."

He knelt down and started kissing the bulge in her corduroy pants. "Please Miss Jennifer, let me be your whore, please let me worship the ladies' cocks, please don't send me away."

As he continued groveling she looked at the ladies with a smile. "What do you think girls, should we give the bitch a try or not?"

They all smiled at each other knowing Wanda had found them a really good fag slave this time. Not needing an answer, she ordered Debbie to his feet. "Alright fag, you're going to get one chance, and if you do a good job I just might appoint you the official Lady's Club Whore, would you like that dear?"

"Yes Miss Jennifer very much, can I suck your cock now?"

She chuckled. "Relax tinkerbell, your pretty little mouth will be sucking plenty of cock very soon, but first you need to get dressed and I have a lovely corduroy dress for you to wear tonight."

Wanda had told Jennifer that corduroy was the key to Debbie's submission and she intended to indulge his fetish as much as she could. She went to the closet and returned with a pretty brown wide-wale corduroy dress. It was knee length and looked very soft. The dress had a collar, long sleeves, an empire waist and it buttoned all the way down the front. Debbie fell in love with it right away and his cock tried to get a boner, but his cage wouldn't allow it. Holding the dress up in front of him Jennifer noticed his dilemma.

"Easy Debbie, you need to learn how to control that boner impulse or you're going to end up with a sore little dickie."

He knew what she meant because he'd been caged before, and he began to get the feeling that things might not be as much fun as he'd hoped. She saw the disillusionment in his face and started laughing. "What did you think you little turd licker? Did you think you were going to waltz in here, get a blow job and then have your fun with the ladies?"

They all began laughing and he felt very embarrassed.

"Put on your dress fag, and fix your wig.

She sat down. "Now stop the pouting and cheer up. If, and that's a big if, you drain every ball sack in the room to my satisfaction, I just might uncage your penis, would you like that tinkerbell?"

He nodded at her with big eyes.

"Well then lose the droopy face and pucker up those sissy lips, you have a half dozen horny cocks to suck, and you're going to start with mine. Since I'm the biggest girl and have to be the last one to fuck your boy-pussy, I'm going to be the first one to cum in your mouth. Understand Daisy May pantyboy?"

There was a sudden sharpness in her voice, and he didn't know if she was angry or it was just her masculine voice coming through a little, but whichever it was, it sounded like she was in no mood for any bullshit. He hurried into his dress and absolutely loved the way if felt on him. When he was finished, he dropped to his knees and started rubbing his face against the bulge in her corduroy pants. The feeling of her rock-hard boner in the soft corduroy fabric caused his penis to fight against his cage again. He looked up and her corduroy jacket was half open, exposing the tight ribbed knit tank top stretched over her lovely tits. Her pretty but serious face was looking back at him, and he couldn't believe that this lady, who could have a fucking harem of sissy slaves if she wanted, had actually dressed herself up in corduroy for a lowly turd like him. Her expression made him feel like she was waiting for something, and very soon it dawned on him what she wanted.

"Miss Jennifer, you have the most beautiful cock of all the ladies, it's even bigger than my mistress's dildos, you are truly a goddess and I want to worship you and your beautiful cock forever. Will you please fuck my pooper, oh God yes Miss Jennifer, please?"

He pressed his face hard into her corduroy bulge. "Please shove your huge cock up my girly ass and make me your bitch. I exist to serve you Miss Jennifer, please make me your personal fuck toy and let me bring you pleasure in any way I can. May I please suck your cock now, please my queen?"

She smiled a little. "Maybe fag, keep going."

"My mouth has two purposes my Mistress, one is to sing praises to you, and the other is to suck your cock. And thank you Miss Jennifer for wearing corduroy, you are very kind, you truly are a benevolent Mistress who takes pity on her whores. I will, and I want, to do absolutely anything you want me to do for your entertainment, anything my queen to show you how grateful I am to be your bitch."