Curiosity Spanked The Sissy free porn video

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You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is that the reason you are here, to try something different to experience domination in a whole new way? As you stare at the house you wonder what you are going to say, how you are going to introduce yourself and your resolve falters.....you cannot do this! On impulse you step out of the car and walk up the garden path and without pause you knock on the door. "Why did I do that!...what am I going to do now?" a panicked voice screams in your head. You have little time to flee as the door is opened by what could only be Mistress Penny. Your eyes traverse her body as you fail to speak. She is wearing black shiny ankle boots, black leggings that cling tightly to her ample thighs and a deep red sweater that hugs her ample curves and barely contains her deliciously large tits. You notice she looks annoyed at your avaricious stare.. "I....I mean....I...." you stammer. "Yes can I help you?" she demands. "My name is Sissy Zelda," you blurt out your sissy name and then turn bright red realising what you have done.. "Really..." She cocks an eyebrow at you expecting more from you but she is obviously curious. "I am a friend of Sissy Maid Davina on Fetlife," you simper. A look of recognition crosses her face and a wicked grin lights her lips. She quickly seems to come to a conclusion. "Come in Sissy Zelda," she commands. You step inside and she closes the door. She stands looking at you as if waiting for something from you, you wrack your brains wondering what that can be. Her fists go to her hips and the wicked grin grows broader. "Well if you are a sissy you should obey the rules of my house, and sissies never ware male clothes....strip!" she commands. You obey immediately without thought and are soon naked but for your locked on chastity cage, the keys for which are still at home. "Mmmm what a tiny clit you have..." she snickers. You blush bright red and you clit throbs at the humiliating comment. "I think it's smaller than Davina's if that is possible......although it is a close run thing...." she giggled. "Still it is good to see the pathetic thing is locked away....do you have the key?" "No Mistress I left them at home," you whimper. "Never mind I don't need that tiny thing" with that she turns on her heels and moves into the house, you obediently follow. She moves to the living room and sits in a leather chair pointing to the floor before her. "I gather you are here to worship me," she smiles. "Yes Mistress" "Well Davina has told me nothing about you but I am sure you have the same pathetic perversions she has..." she sneers. At Davina's name you wonder where she is but your thoughts are interrupted by Mistress Penny. "Well I think we shall start with a few simple tasks and see where we go from there..." she states. "Take off my boots and massage my feet," she commands. You gladly reach down and take her right foot, there is a side zip in the boot and you lower this to allow the boot to slip from her foot. You take the soft pink pudgy foot in your hands and begin to delicately massage it. "Mmmm not bad sissy," she murmurs. Your heart leaps at the praise and you clit twitches. It is however the subtle scent of her feet that is also getting you excited, musky, it hits your nostrils stoking the fire of both humiliation and submission. Her feet are amazingly soft as they should be since Maid Davina pampers them every day. As you move to massage the other foot Mistress Penny picks up her phone and you wonder if she is going to take a picture of you. You wonder what Mistress Michele would think if she saw it and your heart skips a beat. Not for the first time you wonder why you are doing this?. "Hi Jacky, what are you up to at the moment?......." "Oh....Sarah is at your place and you're having some wine...." She looks down at you and winks. "Well guess what... One of my sissy hubbies pathetic sissy friends has just turned up on my doorstep just begging to be used and abuse....fancy coming over and joining in......" A cruel grin curled her lips at your shocked expression. "Yeah sure Sarah can come as well, the more the merrier..." she snickered. "Okay see you soon." She ended the call put down the phone and beamed wickedly at you. "Looks like you're going to be having more fun than you expected," she quipped. "Yes Mistress....thank you Mistress," you simper. "I suppose you're wondering where your pathetic friend is?" "Yes Mistress!" "Well she has been a bad girl spilling my wine, so she was sent to bed early....come let me show you," she commanded. You follow her on hands and knees, mesmerised by her ample swaying bottom in the skin tight skirts. She leads you upstairs and to a small bedroom. When she turns on the light the sissiness of the room is revealed. Baby pinks walls, candy pink dressing table with a girly stool before is and a girly wardrobe again candy pink. You eyes are drawn to the single girls bed, covered in a pink bedspread with multicoloured unicorns on it. Sissy Davina was laid on the bed and would have shielded her eyes against the glare but that she was tightly and snugly secured in a sleeping sack. It was baby pink satin, zippered all the way up the front and was secured at the neck with a pink heart shaped padlock. There were pink leather straps around her chest, waist, pinning her arms to her sides, above her knees and at the ankles. Gradually she managed to focus on Mistress and then her gaze moved to you and her eyes popped open in shock. You notice she is gagged with a pink dummy and bright pink hearts are painted on her cheeks. She blushes at your gaze realising what a pathetic sight she must be. Your clit twitches at the sight of her because you indeed have the same sissy sleep sack and know exactly what it means to be locked into it....sheer sissy bliss! "Hello dear, it seems one of your friends from Fetlife has popped round to worship me, and I thought she could say hello to you," she snickered. "Well say hello to Davina, sissy Zelda," she commands. "I....Hello." You wave from the doorway pathetically. "No, not like that, since you are good friends I'm sure you want to kiss," she prompts and you blush at the humiliation, as does Sissy Davina. You crawl to the bed and give Sissy Davina a peck on the cheek. "Oh come now, I'm pretty sure you two are VERY good friends....remove the gag and give her a proper kiss." She laughs turning the humiliation screw. You reach up and unbuckle the gag before pulling it from her mouth, as you do you see that is in fact a penis gag five inches long, the outer cover made to look like a dummy. "Give that to me." You hand the gag to Mistress and then lean in to kiss Sissy Davina. You have never kissed another man in this way and a shiver of humiliation slips down your spine. Davina must be thinking the same thing because she is bright red. Your clit is painfully rock hard in your cage and you wonder if Davina's is the same. Your lips touch and part, your tongues tentatively touch and then you taste her. As your tongues entwine you struggle to work out what she tastes of, and then it hits you and your eyes pop open, pussy juice, she tastes of pussy juice! You look straight into Davina's eyes to see a look of mirth there, she obviously understands what revelation you have just come to. You feel Mistress move behind you and then something is pressed against your sissy pussy...something penis like. You stop and turn your head to see Mistress Penny inserting the penis gag into you. "Did I say you could stop," she commands. Dutifully you go back to French kissing Davina as the five inch rubber penis slips inside your sissy pussy. It is too much for you as you have not been allowed to climax for two months. "Please stop Mistress...I'm going to cum," you gasp. "Well don't spill it, get your hand under there," she demands without missing a beat. You place your hand under your caged clit and go back to kissing Davina. Seconds later you are spurting your sissy juice into your hand as Mistress continues to pump the penis into you. As your climax subsides Mistress orders you to stop kissing Sissy Davina, you break the kiss and sit back looking at the puddle of sissy juice in your hand.. "Feed that to your friend," she snickers. Davina's eyes grow round at this further humiliation but a groan of pleasure escapes her lips and she wriggles around in her bondage. You move your hand above her mouth which opens like a bird waiting to be fed, you then dribble the sissy juice onto her tongue, finished she closes her mouth and obediently swallows. Your clit throbs painfully and you so much want to be Sissy Davina right now, she smiles happily at you.. "Here she needs her gag in before she goes to sleep." She winks at your shocked face. You know that this has been in your sissy pussy, and was now going back in Sissy Davina's mouth for her to taste for the rest of the night.. "Wont it be nice Sissy Zelda, Sissy Davina will not only be able to taste your sissy juice all night, she will also be able to taste your sissy pussy!" she laughed uproariously. Despite having just climaxed your clit throbs painfully hard, you gaze into Sissy Davina's eyes as you re-insert the gag and see the look of humiliation, frustration.....and lust! It heartens you to know she is enjoying this just as much as you. You have just fastened the gag in place when the door bell rings. "That will be the girls, get down there and let them in," commands Mistress Penny. You crawl downstairs conscious of the time it takes you to get there and also worrying that it may not be her guests but someone else...the pizza guy!! To your relief it is Mistresses two friends, Mistress Sarah and Mistress Jacky, the relief is short lived. "There you are faggot!" demands one. "We have been waiting ages," growls the other bringing the riding crop she is carrying down brutally hard on your exposed bottom but she does not stop with one and beats you six more times before they waltz off to the living room, Mistress Penny arrives shortly after.. "Mmm it seems we have a dilemma, I was not expecting guests and the maid is somewhat tied up..." the two Mistresses snicker. "Wait I know..." Mistress Penny disappears and returns brandishing a small piece of lace. "Stand Sissy Zelda." She then ties a very small and frilly apron around your waist. It is so small it barely covers your stomach. It has the effect of making you look even more pathetic than if you were naked. You blush profusely and your clit twitches which causes a round of ribald comments about the tiny size of it making you blush even more, and unfortunately making it quiver even more with the verbal humiliation! "You are now promoted to Sissy Maid...and will now be able to stand in your Mistresses presence," she commands. "You will serve Mistress Jacky..." You curtsy to the plump Mistress who acknowledges her name. She is slightly shorter than you and very curvy. Her hair is dark brown and pulled into a tight bun with a pony tail at the back, her makeup is severe and she has a sadistic smile which lets you know you are in trouble. She has on shiny black knee high boots, into which black tights are tucked. Her skirt is also black, skin tight and short showing off her ample charms, it appears to be rubber! On top she has on a skin tight black jumper that once again curves around her ample bust.. "....and Mistress Sarah." Once again you curtsy, she is a blonde bombshell. Curvy in all the right places put not overly fat. She has on six inch red stiletto shoes, black sheer stocking. You know they are stocking because although the grey pencil skirt she is wearing descends to her knees you can see the outline of the suspender clasps. She has on a startlingly while blouse that has frills at collar and wrists and barely contains her ample breasts. The sight of all three plump Mistresses has you trembling with equal measures of fear and anticipation.. "Now go and fetch the wine from the Kitchen....you will also prepare some nibbles," commands Mistress Penny. Once the wine was flowing and the nibbles were well and truly demolished the three women look at you with greedy lustful eyes, you shiver at the thought of what they are going to do to you.. "I think it's play time sissy," snickers Mistress Jacky and with that they all start to undress. Mistress Jacky is quickly down to a match frilly black bra and tonga panty set which is also quickly removed in her haste to use you. However you attention is drawn to Mistress Sarah and the corset she is wearing, it is dark purple satin heavily boned. Your love of tight corsetry has you drooling at the sight of her. She unclips the stocking and lasciviously roles them down her legs, watching your avaricious stare as she does. To your dismay Mistress Penny helps her out of the corset and soon she is completely naked. You have never seen so much flesh in one place and wonder if you are going to drown in it.. "First off I think the girls need to relax." With that Mistress Penny produced a leather bag and began to pull sex toys from it. "Come here sissy, time to change role, sissy maid to sex toy......" she snickered. "Open wide." She thrusts a ball gag into your mouth but it is not just a ball gag because protruding from the front is a ten inch fat dildo. It is so thick and long that it strains your neck once Mistress Penny has secured it in place. She takes what appears to be strap on next and gets you to step into it before securing it above your tiny locked up clit. The size difference is not lost on Mistress Penny. "No wonder you're a sissy with a clit that size, maybe you should be in a female chastity belt after all it is smaller than my clit." They all laugh and you blush bright red. The humiliating remarks however get you throbbing hard much to their amusement. "Look the bitches clit is getting hard and still not showing." More uproarious laughter much to your shame. With the second strap on in place Mistress orders you to lie on your back in the centre of the room. You do so reluctantly because you know that pretty soon theses two meaty Mistresses are going to be bouncing up and down on you! Mistress Sarah is the first to step into place, she places a foot either side of your head and you are met with the glorious up skirt view. Her meaty thighs are so thick that at the moment you cannot see her pussy. She kneels and you are encased in soft flesh but at the same time she widens her stance and you are greeted with the first sight of her pussy. The lips are passion swollen and you can see the shine of syrupy pussy juices on them. Your mouth waters and your clit twitches, you wish that it was your tongue and not the dildo that would be entering that molten furnace. She reaches round and positions the dildo at her pussy lips lowering herself slightly as she does to allowing the head to pop inside. You marvel at how the monster dildo stretches those lips and watch a bead of syrupy pussy juice appear and then role down the dildo, she sighs with pleasure. She slowly lowers herself and you watch mesmerized as the dildo slips inside her. It is so terribly erotic and frustrating to watch this spectacle from such close quarters, your clit is throbbing fit to burst! She completely lowers herself onto your face and you quickly draw in breath through your nose, this breath is of course scented with her dark crack which sends a thrill of humiliation down your spine to your painfully throbbing clit. She stays there and you realize she is going to take you to the edge of suffocation. You want to panic but at that point her pussy juice seeps into your mouth filling your senses with the taste of her, you are in heaven. Soon reality kicks in as your lungs start to burn, you start to shudder under her and dearly want to push her off but your submissive nature forbids this. Judging the moment perfectly she lifts her bottom and you gratefully draw in air through your nose. Such is your need for oxygen that you also draw in a little air around the gag which seems to amplify the taste of her pussy juice much to your frustration. All the while you can hear the uproarious laughter of all three Mistresses at your plight. You feel the weight of Mistress Jacky on your lower body and realize she must have mounted the second dildo. Mistress Sarah raises higher and you watch as her pussy grips the dildo and pussy juice slicks the length of it. She then lowers herself again this time forcing the pussy juice to flood copiously into your mouth, you gulp it down like a starving wretch. The two Mistresses slowly begin to hump the dildos faster and you realize all you are is a toy, which causes your clit to drip uselessly much to your humiliation. Soon Mistress Sarah is slamming her pussy onto your face as she reaches her climax, you hear snatches of her orgasmic screams and then she shudders before completely engulfing you in her flesh again. Mistress Jacky is humping your thighs so much so that your clit is starting to ache at the pounding. Your breath however soon starts to run out and you begin to shudder. This seems to have the desired effect with Mistress Jacky because her tempo increases. Dimly you realize you have to make her climax so you thrust your hips up hard to meet her thrusts, fucking her with the dildo! Mercifully she climaxes just as you are starting to see stars. Mistress Sarah lifts off you and the dildo and you draw in breath that is still erotically scented by Mistress Sarah. Mistress Jacky shudders and rests and then she too extricates herself from the dildo. You lie still, dazed, it feels like you have run a marathon and your whole body aches.. "Well it seems you make an excellent sex toy...." laughed Mistress Penny. "But I don't remember giving you permission to fuck Mistress Jacky. Indeed being a sissy I didn't think you had the ability," she snickered. You blush profusely and then even deeper at Mistress Jacky's ribald comment. "It must have been the strap on......did it made her feel manly....not that she is in any way manly!" she snickered. You squirm at their humiliating remarks but cannot defend yourself with the ball gag still in place. "We shall have to think of a suitable punishment later...." mused Mistress Penny. "But for now I need you sissy tongue worshipping my pussy," she growls. The two Mistresses remove the dildos and to your excitement Mistress Sarah dons one of them. "Mmm lots of pussy juices just right for where it's going," she giggles. You shiver at the thought of that monster fucking your sissy pussy, but still your clit twitches. Shakily you move between Mistress Penny's legs. She has hiked up her skirt in preparation for you adoration and you can see the darker damp patch on her satin pink knickers. As you draw closer you get the scent of her hot damp pussy and your mouth waters. Your tongue slides across the satin and you get only a hint of Mistresses pussy, you want more. Although the satin knickers are soft you want to lick the even softer pussy lips beneath. Although the subtle taste is there you want more of that rich nectar. Mistress is also eager for you to lick her as she bids you to remove her damp knickers which you do so eagerly. As you return to your ministrations her pussy lips part stickily in eager anticipation of the touch of your tongue. You lap lavishly bottom to top drinking in her syrupy pussy juices and find the hard nub of her clit. You play with it causing her to squirm and moan. You know she is desperately close so you concentrate on bringing her to climax which she does with a scream mashing your face between her thighs. Knowing the hard nub will be sensitive now your tongue moves lower lapping up the juices you have just created with gusto, your tongue even finds its way to her puckered hole and she shuffles to give you better access. "I knew she would be an ass licker," she growls to the other Mistresses. It is as you are worshiping this dark place that you feel the weight of the dildo in your own crease. You shiver knowing you are going to be fucked by this monster that feels so heavy......and so hot! Mistress Sarah moves back and you feel the tip trail down until it is at your pussy lips. You pause in your ministrations awaiting the painful penetration. "Did I say stop sissy!" commands Mistress Penny. You return to licking Mistress Penny's dark hole as the pressure builds against your pussy. A dull ache spreads from the area which soon becomes pain and you want to move but your submissive nature causes you to stay. There is a sharp pain as the head pops inside and you yelp. "I think she likes it," chuckles Mistress Sarah. You certainly do not as it is quite painful but you know you will be getting more, your clit twitches much to your embarrassment and their amusement! "See what I mean......she is a sissy whore," snickers Mistress Sarah pointing out your reaction to being fucked by this monster. She then begins to slowly slide the dildo into you until you felt a pang of further pain, it seemed it would go no further in.. "Only half in..." quipped Mistress Sarah. "Take a deep breath." You can hear the sadistic glee in her voice. With that she wiggled the dildo backwards and forwards and with a pop of pain it slid completely inside. You have never felt so full......so used before! You blush at the humiliation of being taken like a girl but of course it feeds your sissy nature and excites you at the same time. Mistress Sarah leaves the dildo buried deep inside you and does not move allowing you to again return your attention to Mistress Penny. You find her hard nub of a clit again and begin to play. This time the climax is much longer in the making but when it comes it is far stronger than the first and has her grinding her pussy into your face painfully. As her climax subsides your attention is focused back on the dildo and its inactivity. You itch to have it fuck you despite the pain you know will come. You wiggle your ass suggestively and elicit a laugh from Mistress Sarah. "I think the bitch wants something," she quips. You feel the dildo slowly slide from your pussy and fight to hold it in, you are now so accustomed to the feel of it. She slides it back in and there is once again the sharp pain mid way in. It slides out again, and as it slides back you push back to meet it and there is no pain. So you split your attention between lapping at Mistress Penny's pussy and humping the monster dildo. Pretty soon you feel your own climax rising. "Mistress may I cum.....please?" you beg. "So soon after your last........I didn't think you had it in you!" she chuckles. You blush at the remark but this comment also fuels the fire of your climax." "Yes Mistress......Please may I," you beg getting closer by the second. "You may do so after you have brought me to climax!" she commands much to your dismay. You find her hot hard nub and work hard to pleasure her, as it is her climax beats yours by only a few seconds as her screams are subsiding yours begin. Of course you catch your sissy juices in your hand and much to the amusement of the others Mistresses raise your hand to your lips. Mistress Sara of course turns the screw by first making you beg to drink your own sissy juice and then slowly savoring every tongue full! Having just climaxed the order to clean the dildo is less than appealing but much to your surprise and shame you clit twitches back to life, a fact noticed by the Mistresses. "Yep a real perverted sissy this one," muses Mistress Jacky. Mistress Penny looks at her watch and tuts. "My, my how time flies when one is having fun.....our last guest will be here soon....." she muses. "And we still have to see about your punishment for fucking a Mistress and climaxing before me." You want to argue the last point.....in fact the first point was not your fault but you know it is futile. You are made to bring out a bondage horse and once positioned in the centre of the room are ordered over it. The Mistresses tie you painfully to it so that you cannot move a muscle. Then the second dildo still slick with Mistress Jacky's drying pussy juices is pushed against your lips. you open allowing it to enter but know there is no way all ten inches are going inside. Mistress Sarah has other plans and continues to push it further in. Your eyes pop open and you try to protest but to your surprise it slips into your throat. It appears the position you are strapped to the horse means the dildo could go in much like a sword swallower swallowing a sword!. "Quite the sissy cock swallower," giggled Mistress Sarah picking up on your thoughts. The dildo is pushed fully home until the fake rubber balls squash stickily against your chin. To turn the screw she slides the dildo around until the sticky balls are against your nose and your every breath is scented with pussy juice. As they are preparing to start the punishment the doorbell rings. "Damn both sissies tied up, guess I will have to answer that myself," quips Mistress Penny. This you guess is the last guest, your mind runs wild as to who it could be, another Mistress.....a Master perhaps. Tied as you are you realize he would have free reign to fuck either your pussy or mouth, you shudder at the thought. When Mistress Penny returns the person trailing her turns out to be someone you least expected! Mistress Michele sways into the room a wicked smile on her lips. "Oh my, Has my little girl been bad?" She smirks. She sways across the room and you eagerly follow her with your gaze until she sits directly in front of you. "I see you have been having fun dear.....but you have been cheating on me...." she scolds. She laughs at the crestfallen look on your face and not for the first time you wonder what did exactly drive you here! "It would seem the subliminal hypno tapes worked far better than I expected....." she giggled. To your relief you realize that this was her plan all along but your relief is short lived. "Still that does not allow you to get away with two sissygasms...." she growls. "Ladies do your worst.....I think she needs to learn a lesson," she growls. "No wait...." And she steps out of her knickers......

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Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. 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 Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

3 years ago
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Peter is Spanked by his Wife and Mother

It was inevitable really. I was never going to be able to hide the fact indefinitely from Jackie that even though I am 25 years old and we had been married for three years my Mother has continued to spank me. Mum insisted I tell her so when I was getting undressed one night after a spanking Jackie, my beautiful but easily riled 24 year old wife asked “what happened to you? That is one red bottom.”  I had in my mind that maybe Jackie would tell my Mother to stopspanking me and being spanked...

Spanking
2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 39
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Orgasm Control and the Sissy

Orgasm control, also known as ‘edging,’ ‘peaking,’ and ‘surfing’, is used to keep your partner sexually aroused for an extended period of time without reaching orgasm. The goal is to provide a more intense experience in the end because of the period of sexual frustration. Serious orgasm control is much more than just physical manipulation – there is an emotional and psychological aspect to it. From this sissy’s point of view, the most important factor of orgasm control is the psychological...

4 years ago
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Orgasm Control and the Sissy

Orgasm control, also known as "edging," "peaking," and "surfing", is used to keep your partner sexually aroused for an extended period of time without reaching orgasm. The goal is to provide a more intense experience in the end because of the period of sexual frustration.Serious orgasm control is much more than just physical manipulation - there is an emotional and psychological aspect to it. From this sissy's point of view, the most important factor of orgasm control is the psychological...

2 years ago
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Theater sissy

This is a true story. No exaggeration, no BS. Hope you enjoy it.My ex girlfriend Tori and I had lived together for sometime. Our schedules were such that we had one day off together and one day off alone. I loved our together days but my alone days were porn days. And I LOOOVE porn.I would grab my case of beer, pack of smokes, a towel and head for the computer room. I would look up pics, vids, hop in and out of chat rooms. The whole nine. I was really getting into crossdresser vids at this...

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