Jennifer Monroe & the Ladies Ch. 01

Jennifer Monroe & the Ladies -- Chapter one

Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisked Debbie by and led him to the foot of the bed. As they passed, the ladies continued talking and didn't seem to pay any attention to them, but in reality all eyes were on sissy Debbie, their new little sister. He was wearing a white tank top filled out with his favorite pink bra and medium sized breastforms, he was also naked from the waist down and felt very vulnerable as she paraded him past the ladies. At the foot of the bed was a step stool and Jennifer told him to get up on it. She grabbed his hips and positioned him so he was facing the center of the room.

"Ladies, if I may have your attention please, I would like to present to you my newest sissyboy. His name is Debbie. As has been the case in the past, he was discovered in the university library, then recruited and trained by my beautiful librarian wife and sissyboy Mistress, Wanda. She has an uncanny knack for spotting sissyboys, and has outdone herself yet again. I hope you will all tell her how grateful you are later on."

Even though he was somewhat petrified and had a "dear in the headlights" look about him, seeing all the ladies ogling him in their corduroy outfits made Debbie very horny, and as if on cue his sissy seven-inch dickie sprang to attention in seconds. That didn't go unnoticed, and the ladies giggled and pointed it out to each other.

Noticing what they were focusing on, Jennifer continued. "Yes Ladies, he's obviously a horny little fag too."

She smiled, grabbed his cock at its base and wiggled it around at them.

"And as a special treat, Wanda informed me that Debbie's pretty little penis is a virgin! Being a freshman, new to campus life and obviously a total wimp, Debbie's been forced to be a slut for some of the older boys at school. From what he's told Wanda his mouth and ass have been well used and he's discovered that he's an avid sperm whore, in fact he now seems to crave it. But as it turns out his little dickie has never been inside anyone.

I know, it's a bit hard to believe, but it means that one of us gets to deflower our little sister's pretty penis. Yes girls, someone here tonight is going to get a mouthful of virgin sperm. Now who might that be? You know, personally, I think it should be the girl with the biggest dick."

The room filled with laughter because they all knew no other girl came close to Jennifer's twelve-inch cock. They bickered like catty women for a few minutes, and Debbie was both shocked and turned on by how vulgar they were with each other. He didn't really know why but he loved bitchy women, especially dominant ones, and it didn't matter to him that this particular group of women happen to have dicks. In fact, the thought of a nasty mistress with a real cock instead of a dildo had been turning him on ever since he met Jennifer.

"Alright alright, you can stop your bitching girls, I already have a fair way to decide who gets the prize, and I think Debbie in particular will like it very much. As you were told earlier, our little Debbie has a corduroy fetish, that's the reason we're wearing these outfits. You can thank Wanda for that sissyboy.

Well, as it turns out he loves licking up sperm off of something corduroy. Wanda tells me that even though the boys at school treated him rough, once in a while they would give him a treat, and they called it "feeding the fag". It seems they would lay out a pair of corduroy trousers on a table, or bed, or wherever, then they would gather around the pants and jerk off, pumping their sperm all over the corduroys. And when they were done they made him lick up every drop, which he loved."

She started slowly stroking Debbie's boner. "Isn't that right dear? Go ahead and tell the ladies."

He looked at her and half whispered. "Yes Miss Jennifer."

"Yes what dear?"

"Yes Miss Jennifer, I really loved licking up their sperm."

"Well Debbie dear, how would you like it if all these lovely ladies were to cream a pair of corduroy jeans for you, would you like to lick that up too?"

His boner flexed in her hand. "Oh God yes, please Miss Jennifer, can I?"

She let go of his cock and picked up a pair of black corduroy pants from the bed. After shaking them out she held them up to his face. "Do you recognize these sissyboy?"

His eyes bulged. "Oh my yes, those are Mrs. Monroe's 'fuck the fag jeans', she wears them when she rapes my pooper. I'm not allowed to play with them, please Miss Jennifer, please put them away. Mrs. Monroe will get very angry if I get my sperm on them."

"Calm down dear."

She looked at the ladies with a smile. "Can my wife train a sissyboy or what?"

They nodded and returned her smile, obviously enjoying the show.

"No Debbie, your jizzum isn't going anywhere near my wife's pants, it never will you wimpy fag. However, what IS going to happen, is the ladies are going to do a "feed the fag" on her corduroy jeans. That means that you pantyboy, are going to lick up all our sperm from her trousers. And Daisy May, if there's one trace of sperm left on her jeans when you're done, I'll tell her you jerked off on them. I'm sure she'll love that."

She turned back to the ladies. "We're going to give my wife's jeans a good creaming together, and the first one who cums wins the prize. Does that sound fair to all of you?"

They all agreed it was, and Patty pulled up her jumper and started masturbating. "Knock it off Patricia, we'll all start at the same time.

Or, if you would all prefer, we could watch a show instead."

Jennifer started rubbing Debbie's boner and balls with his wife's corduroys, and that made him very nervous.

"We could guess how long it'll take me to make Debbie cream Wanda's jeans, and the winner gets the prize."

She stopped and gave Debbie a snotty smile.

"That is of course, after I bring my wife in, show her the jeans and watch her abuse the shit out of her disobedient fag for an hour or two."

She turned to the ladies. "Actually, I kind of like that idea, we could pair up and play with each other's clitties while we watched."

She started jerking him off with Wanda's pants. "What do you think fag, do you want me to make you pump your jizzum all over my wife's jeans?"

"No Miss Jennifer, please no, she'll cut my balls off. I'll be good, I'll be your whore and suck all the ladies' cocks, please don't make me cum on her trousers."

He was beginning to whine so she cut him off. "Shut up fag, and by the way, you're going to suck all the ladies' dicks tonight anyway, most likely more than once, so don't try to bargain with me you little slut."

She continued rubbing his boner with the jeans and he began to feel like he might cum, which scared the shit out of him.

"Well girls, which would you prefer, do you want to start out by giving the fag a treat, or watching him get some nasty abuse from Wanda?"

They glanced back and forth at each other for a few seconds before Marsha said. "Jennifer honey, you're getting an awful mean streak lately, I think you've been hanging around your wife too much."

That made them all chuckle.

"Why don't we keep it simple for tonight dear? That is of course, as long as the bitch behaves himself."

She looked Debbie straight in the eye. "But if he doesn't, then by all means let's bring in Wanda for some nasty fun. Hell, I think I'd like watching her cut off his sissy little balls, we could use a new soprano for our all fag choir."

They all giggled a bit, then in a more pleasant tone she asked. "Are you getting the picture bitchboy?"

He nodded sheepishly.

"That's a good boy. Now Jen, why don't you bring the fag fucking pants, or whatever they're called, over here and lay them out on the coffee table?"

Jennifer looked back at Debbie, let go of his dick and seemed very disappointed. About two seconds after she removed Wanda's corduroys from his cock, a small stream of milky white pre-cum oozed out of his pee-hole and ran down the front of his boner. They all notice it and got a little thrill. Jennifer hesitated, licked her lips and stared at the virgin sperm for a few seconds, then looked at the ladies with pleading eyes.

Marsha said. "Forget it Jen, you horny little slut. You didn't win yet, now get over here!"

She took one last look, then proceeded to lay out the corduroy jeans very neatly. When they had positioned themselves around the table, Jen told Debbie to kneel down and lay his face on the legs of the pants. Looking up, he watched Miss Jennifer unzip her trousers and pull out her huge cock, it looked very intimidating. He then watched all the others expose their dicks too, and he couldn't believe what was happening. He had his face lying on Mrs. Monroe's forbidden "fuck the fag" jeans, looking up at a half dozen horny cocks pointed straight at his face. He knew that one by one they were all going to pump his mouth full of sperm, and probably fuck his ass too. That both scared him a little and turned him on a lot. The thing that really put him in fag heaven though, was the fact that they were all dressed in corduroy.

In the middle of everything, he happened to look past Miss Jennifer and saw Mrs. Monroe leaning against the far wall of the basement. She was a tall attractive woman, about 6' tall and slender with shoulder length brown hair. Her face reminded him of the actress Wendy Malick and he guessed her and her husband were in their mid-thirties. She had her arms folded across her chest and a rather snotty smirk on her face. She was wearing a pair of brown mid-wale corduroy jeans with a thick black belt and a rough brown mid-wale corduroy work shirt. Out through the zipper of her pants stuck a huge strap on dildo, bigger than Jennifer's dick. He'd seen her in that outfit before, and he knew that if they let her she would rape the shit out of him all night long. Not just for the entertainment of the ladies either, she would really enjoy punishing him for playing with her jeans.

He didn't know if she ever screwed any of the ladies or not, and he found it ironic that in a room full of horny cocks she was the only one who wanted to act masculine. He flashed on a vision of her fucking Miss Jennifer's ass, and it made his little dickie twitch. When she realized he was looking at her she mouthed the words, "fuck you bitchboy", and he wasn't sure if she was trying to be mean or if she was telling him what she planned to do later on. But either way, she didn't look like she was playing games tonight, she looked genuinely pissed off. In fact, very pissed off.

His gaze was cut short by the sound of snapping fingers, and when he looked up at Miss Jennifer he wasn't sure which vision was sexier, hers or Mrs. Monroe's. She was short, 5' 6" or so and slender like Wanda, but she looked so powerful looming over him like a goddess. As she stroked her big beautiful boner sticking out through the open zipper of her wide-wale corduroy pantsuit, she looked like she was preparing it to give her sissyboy a good hard fucking.

"Are you with me Daisy May? The ladies are ready to get started, and stop worrying about my very pissed off wife. Yes, she wants to rape the shit out of your sissy ass, but she can't do that without my approval. And as long as you keep me and the ladies happy, she won't get it. So I suggest you keep your focus on making us a very happy group of ladies in every possible way, got it tinkerbell?"

She didn't wait for an answer. "Ready girls? First bitch to cream my wife's jeans gets to suck the virgin, on go. One, two, three, Go!"

Looking up at the ladies he couldn't believe what he was seeing. He was rubbing his face in his mistress's pants, looking at a half dozen corduroy clad ladies jerking off and pointing their cocks at his mistress's "fuck the fag" jeans. He was in corduroy fag heaven and licked his lips in anticipation. He knew Mrs. Monroe would punish him severely for the insult to her trousers, but it would be well worth it. As he thought about it he decided it was Jennifer who should be punished, it was all her doing, but he knew it would be him that suffers her wrath. It always was.

Sasha's moans brought him back to reality and the sight before him was one he would remember forever, one he hoped would be repeated very often. A moment later he heard a loud splat as a stream of thick creamy jizzum slapped hard onto Mrs. Monroe's corduroys. Some of it splashed up on his face, but he didn't have time to react before the second stream came squirting out of Sasha's big black mushroom. Half of that stream landed on his nose and lips, and by the time he got his tongue out to lick it, three or four more cum streams splattered onto the trousers. Some drops splashed on his face and hair but most of it formed wonderful rivers and puddles of thick gooey jizzum just inches in front of his face. His own cock had never been harder and was leaking a lot of pre-cum.

Sasha might have won the contest, but not by much. Her third stream was joined by about four or five more, they were all cumming and a chorus of moans filled the room. Debbie had to close his eyes as it was literally raining sperm for about 30 seconds. Almost all of their cream landed on the corduroy jeans, but a few stray streams found their way onto his lips and chin, as if someone was aiming for his mouth. As they collectively empty their ball sacks, they coated his mistress's corduroy jeans with a lake of creamy white sperm. Some of it was as thick as pudding, and formed thick glob islands in the middle of the cum puddle.

He licked his lips, opened his eyes and after briefly savoring the taste, lifted his head to view the pool of white jizzum coating the black corduroy pants. He gazed upon it like a man in a desert who just came upon an oasis. He heard the ladies congratulating Sasha as they squeezed out the last drops of cum from their mushrooms. Glancing up, he was hit in the face with several globs of sperm as they shook their dicks. After a minute they looked down at him and giggled a bit.

Jennifer chuckled. "Um, Daisy May, I don't think Wanda's going to be real happy with you when she sees those pants. Sorry fag, but it seems you're royally fucked. Well anyway, Sasha is the winner so give her cock a kiss and say thank you."

Sasha stuck her dick in Debbie's face and he did as told.

"Alright ladies, lets hurry up and sit for the show, before all that jizzum soaks into the trousers."

They sat quickly and Jennifer said. "Get to it you perverted little sperm whore, show the ladies what an obedient little cum puppy I have. Oh, I forgot."

She got up and went to the closet in a hurry, saying over her shoulder. "Lick it up bitch, right now."

Debbie was in Utopia and licked at the edges, wanting to go slow and savor it. He was on his hands and knees licking the jeans like a thirsty dog. The next thing he knew he felt Jennifer's greased fingers working their way in and out of his asshole. It hurt a bit, but he loved that feeling. She said something to the ladies about a tail, then he felt a stabbing pain shoot up is rectum as she shoved a large buttplug in his pooper. He winced and let out a squeal, but after a few seconds resumed licking. She had fitted his ass with a cute buttplug that has long strands of hair coming out the end forming a doggie's tail, and the ladies got a big kick out of it. Jennifer then sat in the chair and they all enjoyed watching their new fag puppy perform for them.

One of them said. "That's it Fifi, lick up all that filthy fag sperm like a good little doggie."

That was pretty much how the next twenty minutes went, with all the ladies taunting, insulting and humiliating him. They discussed all the different ways they were going to use and abuse him. Fucking his mouth and ass, cumming on him, pissing on him, tying him up and raping his ass with huge dildos, the list went on and on. It all filled his ears as he filled his mouth with their creamy cum, and he kept lapping at what seemed like a pint of jizzum splattered all over the trousers. The sperm tasted heavenly and his dickie twitched every time his tongue pushed through it and tasted her corduroys. He liked being their little fag puppy and loved all the humiliation that went along with it. He liked it so much in fact, that he hoped they were going to make him be their fuck puppy too. That idea turned him on so much that he forgot where he was, and as he licked he said out loud.

"Please fuck me ladies, fuck my ass, make me your whore, oh God please fuck me really hard!"

The ladies all went quiet for a moment, then suddenly began to whoop it up. They celebrated the fact that they owned a new little bitch, and they thanked Wanda for bringing them another horny fuck toy to play with for a while.

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At some point in the midst of all their fun, Debbie heard Jennifer in the background.

"No dear I'm sorry, I can't let you destroy the fag's rectum with that thing, it's too big. You'll have to wait til the ladies are done with him."

Wanda said something but he couldn't make out.

"You're pissed off, I get it. I know you want to fuck him really bad, we all do, but even I go last so I don't stretch the fag's asshole too wide and ruin a good fucking for the rest of the ladies, and that monster dildo is even bigger than me. That's not fair to the girls, it's not their fault the have little dicks."

She paused, then said with a mischievous smile. "Actually dear, I just remembered that I owe Lesley two dollars and I don't have it. You know what though? I bet she'd take a blow job instead, so please be a dear and go suck her cock for me."

She gave Lesley a smile and a quick wink.

"Lesley honey, my Wanda's going to suck your dick and make us even, OK?"

Wanda's scowl disappeared and she gave her husband a sly smile. "Please don't make me do that Jennifer, I'm not a whore."

"Oh stop it Wanda, somebody has to suck Lesley's cock and I'm busy, so be a good little cocksucker."

Wanda winked at Jennifer, dropped to her knees and took Lesley's six inches in her mouth. She was far too eager for someone being "forced" to do it. Lesley had seen this game played out many times before and she always played along. She wanted to make Jennifer happy of course, but more importantly, she did it because Wanda was a very good cocksucker.

The truth was that despite being a tough nasty bitch when training sissyboys, Wanda was in reality a bit submissive herself and loved sucking cock. Her and her husband Randy, otherwise known as Jennifer, were a happy and faithful couple. But Randy understood that the size of his cock made it difficult for her to suck it, so he occasionally indulged his wife by "forcing" her to suck other guy's smaller cocks. It was a selfless act of love, and she appreciated it very much. It was also part of the reason she enjoyed training a sissyboy to serve him whenever she spotted one.

After he had finished licking up the last of his sperm dinner, Debbie sat back on his heels and looked up at Miss Jennifer with a satisfied grin.

"All done sissyboy?"

He nodded.

"I don't think so faggot, a lot of jizzum has already soaked into my wife's pants, and that's totally unacceptable, now suck all the cum out of her trousers. I suggest you make sure they're sperm free Debbie dear, because when you're done I am going to give them to her for close inspection. And Tinkerbell, after the ladies and I are done fucking your bottom all night long, I'm going to turn over whatever's left of you to Wanda so she can have her own fun.