Madame Jenoix

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"Which is where you come in. Some of our friends like to fuck little girls like you in the ass, which can prove problematic. Even girls who are being blackmailed often balk at anal. Luckily," Mistress pushed her hands up inside Jenny's dress, found her nipples and started tweaking them with her long nails. "You are a filthy, dirty whore who loves being fucked in the ass, which makes you perfect. So you are going to be used in the way that all sluts like you should."

Mistress pinched Jenny's nipples, causing Jenny to squeal like a girl in pleasure.

"As I've already said though, first of all you are to be punished and tested. You are going to get up, lift up your dress and pull down your panties. You'll need to get used to that anyway, exposing your ass for use is going to be a common theme for you. Do it now."

Jenny reluctantly stood up as Mistress removed her hands from Jenny's dress, then even more reluctantly lifted her dress at the back and pulled down her pretty knickers. Even this felt good; the soft, frilled silky panties stroked her private place and then ran down her stockings, a terribly thrilling sensation.

She pulled them down to her knees, then followed Mistress's prompts and bent over her lap, with her little backside lifted high up into the air completely exposed.

Headmistress ran her hands over her peachy white ass, loving the quivering little girl over her knee completely submissive to her.

"Your lovely little backside is just delightful, but it can be improved with a nice rosy red glow I think. Squeal and whimper as much as you like, my secretary loves listening to sluts being punished."

Without warning, the Headmistress lifted her hand and brought it down again hard against the sissy girl's cheeks. Not stopping to pause, she spanked her again and again, raining blows down on the soft flesh of the sissy. Jenny, at first too shocked, didn't make a noise for the first few seconds until the fifth or sixth slap on her ass before she started squealing and wriggling in the Headmistress lap. Each time she wriggled her little caged clitty felt some of the Headmistress skirt rub against it causing delight as she had her sissy pussy punished.

"That's a good girl, make lots of squeals for mistress." the Headmistress said, spanking her again and again. "And now you can just whimper for me. Stand up and present your clitty to me."

Jenny quickly stood, not wanting another spanking. Lifting her dress up, Jenny presented herself to Mistress, leaving her pink panties round her ankles.

"Good girl. I do like well-behaved little sluts who do what they are told. Now then we come to our next little test. For this you'll need a blindfold at first, we wouldn't want to scare you would we. So let me just put this on you."

The Headmistress turned Jenny's head to fasten the blindfold over her eyes, preventing her from seeing anything except the inside of the pink satin material over her eyes. The Headmistress then clicked the intercom and said "Miss Jones, now please."

There was a short pause and then Jenny heard the secretary come in, her beautiful long heels clicking along the floor. Jenny was immediately embarrassed to be seen by another young pretty woman who had already made her disgust known.

"You were right about this little faggot then, guess she'll provide some entertainment at least. Okay, you can come in now."

Jenny wasn't sure who Miss Jones was talking to, but she heard another set of footsteps enter the room. They walked over to Jenny and stopped in front of her.

"Now is that any way to greet our guest Jenny? Do you want another spanking or are you going to say hello properly? Now, down on your knees, open your mouth and unzip his trousers."

Jenny's mouth dropped open at this point regardless, not quite believing what she had said. Did Headmistress want him to suck a real cock? Her answer came very quickly.

"Open your mouth and start gobbling that cock before I get angry!"

Jenny quickly knelt down in front of the unknown man and, with trembling fingers, slowly undid the buttons on his trousers. She could feel his cock hardening under her fingers, and reached her red painted fingernails inside, fishing around before grasping his hard, throbbing penis and pulling it out. Jenny could sense the warm flesh in front of her face, and gradually moved her mouth forwards, red lips sliding apart, tongue slipping out to lick her lips as she approached the head.

She took the head of the cock smoothly in to her mouth, tongue sliding underneath it and running along the soft skin. He took control at that point, taking hold of the back of Jenny's head and pushed his cock into her. Jenny resisted a little, but he allowed no resistance as he forced his large manhood into her face.

At this point Jenny heard the Headmistress at her ear, "Mmm good sissy, suck that cock for me. Enjoy as he fucks your mouth, taste his cum as you pleasure him. This is going to be your life from now on, dressed as a slut, sucking cock and drinking lots and lots of hot sticky cum. If you are good I'll reward you with my strap-on later, I know how much you love taking big hard cock in your ass. Madame Jenoix told me all about you and the things she did with your delightful young body. Fancy getting caught in stolen girls clothes and masturbating in a cupboard, you belong to me now. I hope you are enjoying that rock hard penis; I can see your first client is enjoying you. You are going to get your first taste very soon."

Jenny felt the man grasp her head more firmly and speed up, fucking her mouth harder and forcing his cock deep in to her mouth, almost causing her to gag. Headmistress slid her hand up Jenny's skirt, and expertly removed the clit cage that the sissy had been wearing for so long now. Her little clitty suddenly jumped after being released, and Jenny moaned as she felt Headmistress take hold of her and started stroking. Headmistress could see how excited Jenny was and, noting how close the man fucking her face was to cumming in her mouth, she grasped Jenny's clitty and started tugging her quickly.

Her other hand pushed down inside Jenny's pretty dress and started flicking her nipples, causing Jenny to start making cute little squeaking noises as she was pleasured.

"That's it my sweet, enjoy the cock, feel how good it feels when you please me. I love watching you taking nice big cocks in your mouth, and when you make me happy I'll play with you. After you drink his hot cum down, I'll let you shoot your cum on my shoes and then you can lick my heels clean as Madame Jenoix fucks your ass with her strap-on. Yes that's it, suck him hard, lick his balls, and enjoy the soft, silky feel of your pretty pink dress against your skin. Oh you are so cute and pretty, you look so sweet with your slutty make up and princess dress. You are going to be made to take cock in every possible way. Here it comes!"

Jenny felt a change in the rhythm of the man fucking her face just before he stopped and shot all his cum into her mouth. Hot, juicy ribbons of salty jism spasmed into Jenny's mouth, filling it quickly as she used her tongue to entice all she could out.

Jenny couldn't believe how good it felt to be used like this, especially with Mistress playing with her nipples and clit at the same time. She sucked and sucked at the still hard cock in her mouth, listening to the owner groaning as Jenny greedily took it all in to her mouth. The cock was pulled from her mouth, swinging as it came out before slapping back against Jenny's face.

Mistress giggled at this, then said "Oh Jenny you are such a little whore. Now open wide for us, we want to see all the cum in your mouth."

Jenny heard a few quiet clicks, which sounded awfully like a camera...

"Good girl, now swirl it around your mouth and tell us how much you love all that cum before swallowing it all down. Then you'll get to cum yourself."

Jenny ran her tongue around her mouth, pushing the mass of jism around and around, flicking it up and letting it run down her tongue to the back of her throat. As it dribbled back, she gulped the first lot down, and felt Mistress flick her nipple, causing a rush of pleasure as the cum went down her throat. Again and again she gulped more of the cum down, each time Mistress flicking and playing with her nipples and clit to pleasure her and help her associate drinking cum with physical enjoyment.

Eventually it was all gone, and Headmistress gave one final pinch to each nipple causing Jenny to squeal again.

"Filthy whore, covered in cum and dressed like a slut. Lift up your dress and jerk your little clit for us, I want your sissy cream all over My beautiful shoes."

Jenny pulled up the front of her dress and started playing with herself furiously, finally released from the bondage that had stopped her for so long. She felt the tip of Mistress's shoe tap the end of her clitty, and just as she was about to cum her blindfold was ripped off. Still tugging away, she squeaked loudly as she came, and in that fabulous moment of orgasming all over her Headmistress's shoe she saw her audience at last.

Not only was she being watched by Headmistress and Miss Jones the secretary, but the wonderful cock she been sucking belonged to her English teacher! Madame Jenoix had also entered the room, and was standing next to Miss Jones having her breasts fondled as she filmed Jenny's humiliation. She smiled at Jenny as she zoomed in on her cum-stained face. Headmistress lifted her shoe up to Jenny's mouth and pushed the cum covered leather hard into the sissy's mouth.

"Lick it up whore. Not so nice being on the other side of the camera is it? I hope you enjoy eating your cum from my shoe, you'll be getting a lot more very soon."

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12 Comments
AnonymousAnonymousover 2 years ago

Absolutely brilliant! It just kept getting hornier and hornier. I've worn female clothes before, and peeped at girls, but would have loved to have been caught and made a proper sissy like this.

AnonymousAnonymousalmost 6 years ago

This is still my favorite story on Literotica. Probably on the Internet.

AnonymousAnonymousabout 8 years ago

Keep adding chapters, great story.

davinedavineover 10 years ago
Hot.

Well written and very sexy. Made me wet.

AnonymousAnonymousabout 13 years ago
Why?

Why the fuck cant that happen to my sissy ass! I need a mistress just like that!

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