Curiosity Spanked The Sissy Finale free porn video

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You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I should pimp you out," she snickers at your round eyes. Despite the humiliation of this proposition your clit twitches. "I think she likes that idea," chuckles Mistress Penny. "Mmmmmm," muses Mistress Michele and you worry about future events! She places the panties over your face the hot wet crotch directly over your nose of course and you breath in the heavenly aroma. With your mouth gagged you have to breathe through your nose but truth be told you would have gladly breathed in her heavenly scent, sniffed at them like a randy bitch because you worship the ground she walks on. She tightens the panties around your face and this has the effect of amplifying the heavenly scent and pushing the dildo further down your throat. You wiggle in your bonds causing her to muse that perhaps you could take an even bigger cock! You can't help it your cock twitches and all the Mistresses laugh. Mistress Michele returns to her seat and having rucked up her skirt idly plays with her wet pussy. You watch mesmerized as a finger slips inside, then......WHAP. The stroke of a paddle lands on your exposed bottom, you scream around the dildo at the pain and at the same time watch a wicked smile creep onto Mistress Michele's face. The strokes then keep on coming, stroke after stroke until your exposed bottom is on fire. Because there are three of them they tag team meaning you get an endless supply of strokes. You breath raggedly through the panty gag intoxicating and frustrating yourself with the heady aroma of Mistress Michele's pussy, you sissy clit dripping profusely. It has to be over a hundred strokes before they stop and you are left a blubbering wreck. You have never felt your bottom so hot, but you realize the pain is only fleeting and now only a burning sensation lasts. You watch as Mistress Michele's eyes light up and more fingers disappear into her sopping wet pussy. "Oh the riding crop......now this is going to hurt," she snickers. You shudder at the thought and realize you are not going to survive the same kind of beating, fortunately Mistress Penny puts you out of your misery. "Now she is warmed up time for something a little more interesting, six strokes from each Mistress......care to join in Michele dear?" she queries. Getting up she states "Sure......but first....." She moves in front of you and removes both the panties and the dildo. You realize her intension is to have you worship her pussy but your face is level with her naval! "Mmmmm not going to work," she muses. Helpfully Mistress Penny provides a padded stool onto which she steps presenting her molten hot pussy for your attention. She leans in against you mashing her sopping pussy against your face and you long to stick out your tongue and taste her. Your senses reel and your clit twitches as you take the scent of her in......pure excitement is what you get......CRACK! The crop lands on your tenderized bottom and you scream girlishly into Mistress Michele's pussy. The pain is excruciating and you are glad you won't be getting as many as you did with the paddle. Taking hold of your hair Mistress Michele pulls your head back. "Eat me sissy!," She demands and you can see the unbridled lust in her eyes before she mashes you face against her pussy. Your tongue eagerly shoots out lapping at the syrupy pussy juices you find. You find her hot hard clit as....CRACK! the next stroke lands. Because you are worshipping your Mistresses pussy the pain is second thought so you endure the rest of your punishment only flinching when the strokes are overlaid. All too soon Mistress Penny states. "Your turn Michele dear." Fortunately you have been able to bring Mistress Michele to at least one orgasm. But it is a fact that did not escape Mistress Michele. "Only one orgasm.....tsk...tsk." Mistress Michele moves behind you and in turn Mistress Penny steps up onto the stool before you. However instead of presenting her pussy for you to worship she presents her bottom with the ribald remark. "Make sure you get that piggy tongue in deep sissy." You are then smothered by her ample bottom and you face is crushed against her puckered rosebud. As commanded your tongue snakes out and begins its worship.....at the same time...CRACK! The first of Mistress Michele's strokes lands, she seems to go out of her way to land all six strokes on other previous strokes much to your torment. Finally you are left an exhausted wreck on the horse as the Mistresses enjoy a glass of wine. "Serving ourselves is a pain in the arse....." muses Mistress Penny. "Besides I have a bone to pick with my pathetic husband.....talking about me on Fetlife....with another sissy indeed," she growls. You are unfastened from the horse and ordered to go and fetch Sissy Davina, Mistress Penny supplies the keys to unlock her sleep sack. You crawl from the room much to the Mistresses amusement as they admire their handy work on your bottom. In Sissy Davina's room you switch on the light and quickly move to the bed to unlock her. You can see the look of confusion and shock on her face. It seems there are so many questions she wants to ask. "Mistress Penny wants you." A look of fear crosses her face and her gaze flicks to the CCTV camera mounted in the corner of the room. She knows the only answers she is going to get are painful ones. Untied she sits and then stands giving you a chance to see what she is wearing. She has on a gossamer pink negligee that ends just above her crotch exposing her tiny clit locked tightly into a candy pink restrainer. On her hands and feet are pink mittens and bootees. Seeing she is ready you crawl from the room and she joins you on hands and knees. As you return to the living room you wonder what thoughts must be running through her head. You enter the living room and looking back see her eyes go round at the Mistress arrayed around the room. You know she has told you about Mistress Sarah and Mistress Jacky, how she was humiliated by them on numerous occasions....put Mistress Michele! This must have been a new and shocking development. "Stand Sissy Zelda....you are promoted to sissy maid again....." commanded Mistress Penny. "Now freshen our drinks," she orders. As you are topping up the drinks poor Sissy Davina is strapped to the horse you have just vacated. "So what is this about you blabbing about me on Fetlife!," Demands Mistress Penny. "Mistress Penny......I can explain," simpers Sissy Davina. "No you can't.......and did I say you could speak," storms Mistress Penny. Sissy Davina's head drops as she realizes she is in for a beating, however her tiny clit twitches. Sissy Davina is bound to the horse you have just so recently vacated and left to contemplate her fate as the Mistresses sip their wine and chat idly. You pity poor Davina but despite having a tender bum also envy her, her bound state. You also realize this is going to raise some interesting questions when next she messages you on Fetlife. The Mistresses all pick up a paddle and you realize all four Mistresses are going to be swatting her exposed bottom, will that mean even more strokes, you wince at the memory as her punishment begins. Because poor Davina is not gagged her girlish yelps are soon filling the room causing Mistress Penny to call a halt to the proceeding. "Enough!...I can't listen to her pathetic squeals any longer," she exclaims. She retrieves Mistress Michele's panties from the floor and proceeded to stuff them into Sissy Davina's mouth, you see her eyes pop open and wonder what she is thinking. You are truly envious now because she is tasting your Mistress! Mistress Penny seems to think this is not enough however because she gathers her own used panties and stuffs them into Sissy Davina's mouth. Not to be out done both Mistress Sarah and Jacky supply their used knickers as well. Soon poor Sissy Davina's cheeks are soon bulging as much as her eyes! There is no need to secure the soiled panties in place but Mistress Penny turns the screw of humiliation by pulling one of the Mistresses used stocking over her head laughing. "At least we don't have to see her pathetic tear stained face!" "Now let's start from the beginning," she states, eliciting a pathetic mewl from Sissy Davina. You then get to watch what you so recently have had done to you. At the end of the paddle spanking Sissy Davina's bottom is literally glowing bright red. Her breathing is wragged and no doubt she is extremely frustrated having had four Mistresses panties in her mouth for the whole experience. Indeed there is a puddle of sissy juice below her caged clit and you wonder how long it is since she last orgasmed! You thank your stars for your recent sissygasms but you also remember you paid the price. The Mistresses take a short break and you top up their glasses and then the riding crops are produced. Soon the strokes are landing thick and fast and despite the very large gag Sissy Davina's squeals fill the room. You see firsthand the vivid red stripes that quickly turn blue as the bruises blossom. Once again she is left a gibbering wreck as you were. "Untie her and take her upstairs to her room...." orders Mistress Penny looking at you. "Davina, put on something slutty......and pick something appropriate for your girlfriend," she winks. "Yes Mistress," you answer for the both of you. You make to crawl but Mistress Penny stops you. "No, off you go hand in hand like two girly girlfriends," snickers Mistress Penny. So humiliation blushing both your faces you head upstairs, wondering what further humiliations the Mistresses have in store for you. In her room Sissy Davina looks at you expectantly and you realize she needs you to remove the mittens before she can do anything. Once they are off she removes the negligee, booties and finally.....almost reluctantly removes the panty gag. She looks you up and down to gauge your size and then she produces what appears to be a cheerleaders outfit in a shiny metallic pink material. The short pleated skirt comes first, because it is Davina's outfit it is even shorter on you than it would be on her, not even covering your caged sissy clit and looking quite ridiculous, you blush realizing the humiliation you are going to get from this. The top of course barely covers your nipples! and is made from the same material. Across the front of your very flat chest are the words "Daddy's Gurl" picked out in gold sequins which makes you blush and you clit tingle. Sitting you down she applies makeup to your face and by the way she is lathering it on you can tell it is going to be very slutty, the finishing touch is a purple bob styled wig. When she has finished she allows you to turn to the mirror to admire your reflection. You gaze at a very....very slutty cheerleader as she slips on the pink frilly ankle socks and white glossy trainers. Having dressed you Davina turns to her own attire. She starts with a purple PVC corset and she elicits your help to get it extremely tight giving her an hour glass figure. She places two medium sized breast forms into the cups of the corset giving her an even sexier female appearance. She attaches black fish net stockings to the suspender straps and adjusts them until they are perfectly straight. Next she slips into a shiny purple sleeveless PVC dress that clings seductively to her new feminine figure and your clit tingles at the sight of her thrusting breasts and hips. She sits before the mirror and applies her makeup that is even more Vampish than yours....the lips so red and glossy. Her wig is black with long curls that cascade down her neck. To finish she straps six inch glossy black stiletto shoes on and totters to her feet before regaining her balance. After a little primping she takes your hand, smiles nervously at you and guides you back downstairs. In the living room more wine has been flowing and there are lots of ribald remarks about your attire and how much you could both make on the street. You both blush and her hand tightens in yours, your clit however betrays your excitement and twitches in frustration eliciting more ribald comments from the Mistresses. Fortunately Sissy Davina having a slightly lower hem line is spared this ignominy. "Well since we are going to pimp these two pathetic sissies out perhaps we should see their seductive dance moves," laughs Mistress Penny moving to the music tower . You shiver in fright, you are no good at dancing and definitely not erotic dancing, the pale face and look of shock shows you that Sissy Davina feels the same way. You are both cajoled into the centre of the room and the music begins. "...there aint nothing liiiike.....a little bit of bump and grind....." You start to sway your hips to the music but it is stilted and mechanical. Sissy Davina does not fair any better until she is inspired to grab your hips and grind her caged clit against your battered bottom which is both painful and humiliating. The Mistresses love this and urge her on to "Be the man," with lots of hysterical laughing. This helps Davina and she is soon swaying with the music. Four more tracks follow and still you barely manage to loosen up whilst Davina fairs a lot better but still appears quite pathetic to the Mistresses. "Well what do you think girls.....who is the best dancer," laughs Mistress Penny. All the Mistresses agree that Sissy Davina although still pathetic is better than Sissy Zelda. "Okay Sissy Davina, since you are the winner you get to choose....I will let you out of your cage and you can fuck Sissy Zelda's mouth or sissy pussy......what will it be?" You glance out of the corner of your eye at Sissy Davina's perplexed expression. Obviously she has not cum in a while and is probably wondering which way will make it last the longest. Impatiently Mistress Penny growls. "See what I mean girls all sissies are air heads, they can't even make a simple decision. Okay you will be fucking her sissy pussy........and she will be licking Mistress Michele's," she winked wickedly at you and then burst out laughing at your shocked expression. You will be worshipping Mistress Michele's pussy! It is the one thing in the world you truly adore and your clit twitches with excitement. Mistress Penny unlocks Sissy Davina and you hear her gasp with relief at the freedom, you wish you had the chance to do the same as you are ordered to kneel in the centre of the room. Sissy Davina moves behind you and you feel her hard cock at the entrance of your sissy pussy, at the same time Mistress Michele lays before you her legs spread wide her hot glistening pussy ready to be worshipped. "Okay Sissy Davina you may orgasm but you must ask Mistress Michele to do so....." ""Yes Mistress Penny," simpers Sissy Davina. "But you are not allowed to do orgasm until sissy Zelda has made Mistress Michele climax...," she snickers and you hear a gasp behind you. Looking into your eyes Mistress Michele quips. "You better make it fast to help your girlfriend because I don't think she can last too long.......how long has it been Sissy Davina?" "Two months Mistress Michele," she whimpers and you know she is going to struggle, fortunately you recently had your sissy pussy filled with a monster dildo so it is well lubricated and slightly looser than normal! You feel Davina's hard sissy clit slip into your sissy pussy and are surprised at how good it feels. Unlike the strap on sex you have had before this is so much better! Her clit is hot and throbbing and although it is not very big you still feel it. Almost in unison you both groan in pleasure causing a ripple of laughter from the Mistresses. She pulls out and then thrusts back in here breathing already fast and wragged, you revel in the pleasure of her thrusting clit but you moment of bliss is interrupted by Mistress Michele. "You better get on with it......I don't think your sissy friend is going to last more than a few strokes," she smirks. Reverently your tongue dips into her molten pussy and tastes her syrupy pussy juices sending you to submissive heaven and making your clit ache. You long to taste more of her juices but know you must help Sissy Davina. You find Mistresses hard nub of a clit and begin to play. You feel a shudder go through Mistress as you hit the right spot but you also hear a gasp and feel a shudder from Sissy Davina. Her thrusting pauses but Mistress Michele is having none of it. "Did I say you could stop!," She demands. "Please Mistress......I need to orgasm," she pleads. "Not until I have," she snickers at poor Davina's plight. Slowly Sissy Davina begins to thrust back into you and having heard her pleas you redouble your efforts to make Mistress Michele climax. Mistress is obviously turned on by having two sissies to torture because soon she is writhing on your questing tongue. Mistress announces her climax with a scream of pleasure and moments later....... "Please...oh please Mistress.....Please may I orgasm," pleads Sissy Davina. "I suppose you can now," laughs Mistress Michele. Sissy Davina announces her climax with a pathetic mewl that has all the Mistresses laughing uproariously. You feel her slip from your sissy pussy but realize she is still hard. "Your sissy girlfriend is in need of a cleanup," snickers Mistress Michele. You turn round to be presented with Sissy Davina's clit still hard and slick with your pussy juices and her sissy juice. You realize that you are going to have to taste both your juices and a blush of humiliation reddens your face. Tentatively you lick at the tip of her thrusting clit and are treated to her metallic sissy juice, there is a snicker from the Mistresses when you then suck on the head of sissy Davina's clit, tasting her and yourself this time. More eagerly and much to the amusement of the Mistresses you continue your ministrations. As you are doing so Mistress Sarah speaks. "Well I don't know about you girls but I am ready to party, how about we hit the town?" You are surprised as the other Mistresses including Mistress Michele agree....in fact she adds smiling wickedly at you. "Maybe we can pick up some real men." "What about the two sissies?" quips Mistress Jacky. "I will tuck them in for the night," smiles Mistress Penny mischievously. "You two upstairs and undress......I will be up soon," commands Mistress Penny. You stand taking Sissy Davina's hand and head upstairs, the taste of her is all you can think about which makes your sissy clit throb. Upstairs she helps you out of your clothes and you do the same for her. You so much want to speak to her but no you cannot because of the continuous surveillance. Sissy Davina cleans the makeup from your face and you do the same for her. Naked and pathetic you both stand awaiting Mistress Penny, when she arrives Mistress Michele is also with her. You note that Mistress Michele is carrying a bag, she moves to you and taking the key for your clit cage removes it. You sigh with the pleasure of the freedom and your tiny clit quickly hardens much to Mistress Michele's amusement, but you also wonder what wicked plan she has. Mistress Penny arranges the satin sleep sack open on the bed and gets you and Sissy Davina to lay on the bed on your sides facing each other almost touching. From the bag Mistress Michele produces a clear gel sheath. It is used for masturbation, smooth on the outside and ribbed inside. It is normally meant for one man sized cock so Mistress Michele easily slips it over both your clits pinning them together pleasurably. You both look into each other's eyes, you read lust on her face and realize she must be seeing the same. Involuntarily you move your hips and she does the same enjoying the pleasurable friction, eliciting a chuckle from both Mistresses. "They are going to frot each other senseless by the end of the night," snickers Mistress Penny. From the bag Mistress produces a pink ball gag, but it is not a normal gag. From the ball protrudes not one but two four inch penis gags. You realize it is meant to silence and secure two sissies together. Mistress Michele moves behind you and you feel the intrusion of one of the penis gags in your sissy pussy. She moves behind Sissy Davina and by the shocked expression on her face know exactly where the other one has been thrust. With a wicked grin on her face she pushes the penis gag into your mouth. The dark taste makes you realize exactly where it has been and when the other penis gag enters Sissy Davina's mouth her look tells you she understands exactly what Mistress Michele has done. Both of you wriggle at this humiliation causing the pleasurable friction of your sissy clits to further excite you both. Chuckling at your sissy thrusting Mistress Michele locks the gags in place. More items appear from the bag, two matching anal hooks and two matching bondage mittens. Each hook has a large four inch ball on one end a hook on the other. Once again your sissy pussy is invaded as the ball is slipped inside and the same is done to Sissy Davina. "Slips your hands around your girlfriends hips," whispers Mistress Michele into your ear. At the same time Mistress Penny whispers something into Sissy Davina's ear. She blushes and wriggles her arms inside yours and around your hips so that you are intertwined intimately. You both wriggle, pleasuring yourselves with you intimate contact. You do not know about Sissy Davina but you are very close to climaxing. You looking into her eyes and see by the lust there that she is also very close! In fact the pleasure you realize is unstoppable! So as the two Mistresses bind your hands into the bondage mittens and attach them to the anal hooks in each other's sissy pussies you both thrust with unbridled lust against each other. Fiendishly being attached to the others anal hooks means that any hand movement is transferred to the others sissy pussy. Sissy Davina squeals around the penis gag and you feel the hot splash of her sissy juice on your tender clit head and you too are sent into orgasmic bliss. Both your hearts beating like racehorses post climax, your breath fast and wragged you look up at your Mistresses nervously. Both of them are watching you hands on hips, a look of smug satisfaction on their faces. "What did I tell you and this is only the beginning of the night," snickers Mistress Penny to Mistress Michele. "Mmmm......they are going to drive each other insane by the end of the night," she quips. You are then both zipped into the sleeping sack and since it was only made for one it is very snug. Both Mistresses then work on the straps securely locking you in place and further mashing your bodies against each other. By the time the padlock is clicked in place at the collar you are both experiencing another orgasmic climax this time you marginally beat Sissy Davina to the orgasm. The light goes out and there is only the light from the doorway framing the two Mistresses. "Sweet dreams," murmurs Mistress Michele. "Sweet erotic bliss," chuckles Mistress Penny as the door closes. You are left in darkness your next sissy orgasm building.......

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One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
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Sissy gets a spanking

I see there are lots of CD spanking videos on this site. That reminds me of a couple i met many years ago. She was a dominate woman who loved to spank sissies. Her husband was a submissive sissy. I took her out to lunch and we just talked for quite a while in my car and she had me take my pants down so she could see my panties and i had on a garter belt and nylons that day. We agree that i would come to her place in a few weeks for a spanking. I went to her place and walked in and she told me...

4 years ago
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Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

3 years ago
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Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
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Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
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My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

3 years ago
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My Neighbour is a Sissy Finale

Danny gave me the keys to my chastity cage back a week later and to be honest I was a gibbering wreck, which he knew! He had a wicked grin when he handed over the keys. "Next time you get to be the Mistress...and I hope you will be very wicked," he winked. "Oh just you wait and see," I growled. Our next chance to meet came just over a month later. I waited in the living room for him to arrive. Black shiny thigh high boots, black fishnet stocking, new purple PVC hot pants in which...

4 years ago
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A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

2 years ago
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Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

4 years ago
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Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

4 years ago
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CDg Sissy Slut Cocksucker goes to local Adult Theater

I love dressing up whenever possible, which is not often enough. But, what I love even more is dressing up as a hot and wanton sissy slut cocksucker and then going to the local adult theater for some great XXX fun. I am not totally passable, but have been told my legs are fantastic and my ass is nice and tight with a hot tramp stamp just above my ass. Most guys say it's sexy as hell while they are fucking me. Fortunately, my wife had to go out of town for a few days and thereby giving...

3 years ago
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My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

3 years ago
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Sissy Spankings

I have had this fetish for wearing women's tights and knickers for most of my life and enjoy it all the more now I'm in my 60's.I developed a need to be punished for my behaviour and found that being spanked filled that need.I meet with several friends and enjoy spanking sessions with them .... I found I was not alone with my fetish so not only did I find an outlet for my fetish I met similar men with the same passion for tights and spanking.It is such a delight to mix with adults who share the...

4 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

2 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing
4 years ago
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My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

3 years ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

4 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

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