I'm A Sissy Princess free porn video

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Once upon a time, there was a very beautiful princess, who loved to dress up and wear her pretty gowns and pink frilly panties and prance around like a sissy girl. But the princess had to hide who she was, and dress in her guys clothes, and the thought of no one knowing who she really was, and that under the frilly panties was a big, solid cock, made her very excited. But she lived alone, and had no one to keep her in control and she would be very naughty, touching herself and making her throbbing cock spurt all over her pretty outfits.



But one day, a sexy mistress came to visit the princess while she was dressed in her boring guy's clothes. At first she tried to act like a normal guy, but the mistress knew what a prancing sissy she was inside and how naughty she'd been on her own and decided to teach her a lesson. "I know princess, that you've been a very bad sissy girl before I've been here, but I am a queen and I don't tolerate impudent little princess's" said the mistress. Princess looked shocked, and couldn't think of what to say, but her eyes followed the mistress's hands as they moved. Mistress took a box out of her bag and said to the princess "leave the room, take off those disgusting boy clothes and put on what's inside the box, now".



But the princess was scared and didn't know what was in the box and wouldn't move. Mistress knew she'd have to be punished if she didn't do what she was told so she grabbed the back of the princess's hair and pushed her head down, until she was bent over and made the sissy princess put her hands on her knees, while roughly pulling down the horribly boy's jeans and boxers until her ass was bare. And the mistress spanked her hard with an open palm on her ass, leaving a large red stinging hand print on the princess's ass cheeks.



Now the princess was more scared of the mistress than what was in the box, and apologised for not doing what she was told. Mistress pulled her boxers and jeans back up and handed her the box, "thank you, mistress" said the princess, as she nearly ran out of the room. She put the box on her bed and opened it to see what was inside and gasped. There was a pair of soft fishnet stockings with a seam in the back, a black lace frilly neglige with a pink silk ribbon at the bust, and a pair of matching pink satin frilly panties. She quickly took off all of her guys clothes until she was naked, and smiled and she pulled the stocking up over her legs, enjoying how soft they felt against her skin. The satin panties felt even better holding her now hard cock tight against her stomach, so it couldn't be seen when she slipped on the lace neglige. She decided she should wear her black heels to go with the outfit, to look like a proper princess, and with butterflies in her tummy wondering about what was going to happen, she went back out to present herself to her mistress.



"Not bad" said the mistress, and princess smiled, happy that the mistress was pleased with how she looked. "But not good either" scowled the mistress, and the smile fell from the princess's face as she looked down at her feet, feeling embarrassed and ashamed that mistress didn't think she was pretty, and there she was, standing dressed like a sissy slut! Princess looked up to see the mistress looking through her bag again and her eyes widened as she wondered what else was in there. "This will help" and mistress took out a long blonde curled wig and a lipstick, and walked towards her. Princess couldn't help but look the mistress up and down as she walked towards her, notcing how tight her black satin skirt was around her hips, and how hard her nipples looked under her thin red silk blouse. Mistress pulled her chin up facing her, and pulled the long blonde wig onto her head, fixing it in place and making the curls sit delicately around her face. She opened the lipstick and told her to open her mouth and pout her lips which she did immediately - she didn't want spanked that hard again, or worse! Mistress put on a thick layer of lipstick before closing it and putting it away in her bag, and turned around and looked the princess up and down.



"Much better you look very pretty, and very sexy now, stand with your hands behind your back, and your legs apart, so I can see you properly" said mistress, as she walked towards the princess, and kissed her hard on her lips smudging both of their lipstick. Mistress ran her fingers around the frilly lace edge of the straps and bust of princess's outfit, and then both of her hands slid down the sides, the feel of the lace rubbing against her skin made the princess hard, straining her satin panties. Mistress kept moving her hands lower until they were brushing up against princess's thigh just under the seam of the neglige, and then touching the edge of the pink satin panties. Her fingertips followed the frills of the panties, from the side of her thigh to between her legs and the princess squealed when she felt her fingers lightly run up the length of her cock.



Mistress pulled back her hand and walked around her, until she was standing behind the princess and started to do the same to the back of her outfit, hands running along the edges of her straps, and down her back until her hands were cupping her buttocks the lace rubbing against the satin panties. "I want you to bend over again, put your hands on your knees, but don't worry if you do everything I say, you won't get spanked again" and princess did exactly as she was told, not wanting to displease her mistress again! Mistress flicked back her neglige over her back, so her ass was exposed covered in pink satin, and started to rub her hands over her ass cheeks, then pulled the panties up tightly so that they were wedged into the crack of her ass pulling at them and rubbing her fingers over the tightly packed satin which excited princess so much she felt pre cum forming and wetten her panties. Mistress suddenly grabbed the sides of the panties and pulled them down to her knees and she saw the wet spot as she looked at the panties and smiled, putting her head between her legs and sucking the head of her cock between her lips wiping the cum off with her tongue. She stood up and kissed the princess, smearing the cum onto her tongue with hers as she kissed her hard, making even more of a mess of her pretty lipstick.



Mistress gripped her cock so tightly in one hand that she yelped with pain and surprise, and said "don't you dare cum before I let you, otherwise I will make sure that no one touches that cock for a month! Now, stand back up, hands behind your back again so you're not tempted to be a wuss and start touching that throbbing hard cock" and she stood up straight, even though her satin panties were still around her knees, and put her hands behind her back like she was told. Even though she could feel the hem of her neglige brushing over her cock which was standing to attention, she tried not to let it excite her too much. Mistress stayed on her knees and ran her hands up the back of her legs up the seam of her fish net stockings and screwed up her face, as princess's legs began to shake wondering what was wrong.



"These are not a princess's legs are they? When were they last shaved or waxed? I can feel your horrible bristly hairs poking at my finger, do you think thats what I want to feel when I run my hands over your long legs?" said mistress in a very harsh tone that made princess gulp as she tried to explain herself "I'm sorry mistress, I should have been preening myself properly, I'm very sorry, please let me fix this?" she begged. "Fine, if you can get rid of the hair and be back looking like I expect a princess to in 10 minutes, maybe I won't tell everyone what a sorry excuse for a sissy princess you are. But don't you dare pull those panties back up. Go then" and princess ran from the room into the bathroom, hurridly pulling off her shoes and stocking, struggling against the panties that were still restraining her at the knees.



She turned on the shower and started quickly lathering up her legs and shaving them, trying to hurry but knowing making a mistake would displease her mistress, and she would be scolded and punished for it. When she was sure she'd gotten it all she rinsed her legs off and dried them, making sure they were completely smooth she redressed in her stockings and shoes, and shuffled back through with her panties hanging below her knees now, threatening to fall down completely to her ankles.



Praying she made it in time she went back into the room, she walked too quickly and her panties fell to her ankles as she entered the room, but the mistress just sat there on the sofa and laughed at her making her blush and feel embarrassed. "Come back over to me so I can check your legs for myself" and princess went and stood in front of her, hands behind her back as she knew she should. Mistress ran her hands up the front of her legs and the feel of them on her newly shaved legs excited her again, and she struggled to make sure not a drop spilled from her swelling cock. "Turn around and bend over again for me" and princess knew what she had to do, bend over and put her hands on her knees, making sure to bend over at the waist to show her ass off for her mistress.



Mistress grabbed her waist with her hands and her wet tongue licked princess's balls and up her ass crack, circling around her hole before plunging her tongue inside, it was hard and wet and thursting inside princess's ass and she moaned loudly nearly screaming as mistress lapped at her ass, flicking up inside of her making her push back against the tongue wanting more. But mistress's soft tongue pulled out of her, "mmm your man pussy is nearly as soft as a real lady's, isn't it princess?", "yes mistress" she quickly replied, desperate to beg her to start fucking her properly with her tongue. Instead she felt a finger enter her and start to slide in and out, first one, then 2 and 3 fingers, spreading as they entered her ass making it wider and she moaned as she felt herself spread open, as her cheeks were pulled wide apart and then the hard wet tongue she wanted so much slid inside her again, hard and long fucking her so deep she couldn't bear it. She thought she'd cum from that alone if she didn't keep her control but mistress kept fucking her harder with her tongue while her ass was pulled wide apart and she gasped "please mistress, please let me cum".



"No, please mistress" she begged as the tongue was removed, and felt a sharp slap across her cheeks. "I told you not until I let you, and I'm not nearly done with you yet. I've barely started to inspect you and you want to cum already? Have you no control over that pathetic little cock of yours? I will have to teach you better manners, you should be begging to make me cum instead! Get on your knees and turn around". "Yes mistress, anything to please you mistress I will do for you, anything you say" she said as she turned around to see mistress sitting on the sofa, with her legs wide open she pulled up her tight satin skirt to expose her black lace panties which she pulled aside, exposing her gleaming wet pussy and she knew mistress was enjoying telling her what to do.



She tried to bend her head over to taste her mistress's pussy but she pulled the back of her shoulder straps and looked her in the face and said "I want you to thrust your tongue straight inside me and fuck me until the cum runs down into your mouth and bury your face into me so hard your lips taste like a proper woman's lips, and I will taste them to make sure you've done it properly. Do you understand?" princess nodded and said "yes mistress" then bowed her head down and used her tongue to fuck her mistress just as hard as her ass had been fucked, savouring the sweet taste of her cum as it rushed down her tongue and she tried to rub her face in it, making sure it covered her lips and her face. Mistress pulled her back up by her neglige and princess nearly resisted until she remembered what would happen to her and quickly snapped back up. Mistress ran her tongue around her lips, tasting them to make sure they were drenched with her cum before opening her mouth with her tongue, licking the cum up off her tongue them both tasting it as she kissed her so deeply.



Mistress laughed again and the princess blushed "you've made a complete mess of all that lipstick I so carefully put on you, what kind of gratitude is that? Go and fix yourself up" and she handed her the lipstick. Princess nearly tripped over the panties that were wrapped around her ankles and mistress roared with laughter, making princess go a deep scarlet with embarrassment. "Take those sissy panties off, clearly you don't know how to wear them properly you'll have to earn them back if you want them" Mistress said through her laughter, and princess took them off, and went and fixed her lipstick making her lips look bright red and still surrounded in cum. God she looked like such a dirty slut right now.



"Much better, do you feel like a princess now you've reapplied your makeup? Well you're good at licking pussy, but thats not all im going to make you lick, I want to make sure you're good at sucking everything. Come kneel in front of me again". Princess did as she was told and her eyes followed mistress's hands as they rumaged through her bag again and she wondered what else could be in there. Mistress pulled out a big thick dildo, or maybe a vibrator? Princess couldn't tell. "Tilt your head back and open your mouth, if you're really a good sissy princess you'll be able to take the whole length of this just like a real cock" and mistress rammed the dildo in her mouth, almost hitting the back of her throat and princess nearly gagged at how deep it was but managed to keep her mouth open. Mistress was fucking her mouth hard and making the toy go deeper in her mouth making princess want to gag and spit it out, but not daring to upset her mistress. "That's it, take the whole fucking cock and mess up your lipstick again, smearing it all over not caring how dirty your face looks, but you don't care do you as long as you can get cock in your mouth you dirty bitch" and princess was taken aback at the harsh language! but she knew she was her bitch, and she would always do whatever her mistress told her no matter how dirty it made her feel.



Princess nearly managed to take the whole dildo in her mouth and was nearly going to gag and not be able to go any futher when mistress started to pull it further out, letting her wrap her lips around and just such the end of it. She pulled it out and princess gasped for air "Well you sucked that cock like a pro princess, I bet you could suck a real one right down to the base couldn't you! Hope you made it nice and wet now did you?" and she could see the dildo was dripping with saliva soaking wet and was relieved. "lie on your back for me" and princess did as she was told, lay down on her back with her legs straight out below her, her cock still standing up and she didn't know how much longer she could hold on and hoped she would be allowed to cum soon before she exploded all over herself.



Mistress was kneeling beside her, and pulled her legs up opening them apart over her shoulders. "you'd better hope you soaked this cock or it will hurt when i fuck you with it" and started to push the dildo inside her ass, princess could feel it stretching her and moaned so loudly, thankfully it was soaking wet and could push inside without too much pain, but it hurt how much it was stretching her tight ass, she'd never had such a thick toy inside her. Mistress plunged it in deeper, thrusting it really hard and fast into her as she lowered her head, and started to suck on the tip of her cock and suck it inside her mouth inch by inch. "I want you to cum for me, all over my face and my tits" mistress said as she finally took off her silk blouse, exposing the black lace bra underneath which she started to undo. All princess could think was how she wanted to be filled up again, trying so hard to keep her cum inside so she could come on those tits, and just maybe, if she was very good, she would be allowed to lick them clean!.



Mistress picked up the toy, and used it to slide into her own pussy, pushing it in and out right in front of princess as she watched not sure if she was allowed to touch, so she kept her hands at her sides and watched the dildo being covered in her mistress's cum. The dildo was moving back towards her ass and she screamed as it was thrust hard inside her, and started fucking her fast and deep immediately and she squealed so much. Her mistress's tongue wrapping around her cock again, pulling it inside her mouth and she couldn't hold it in anymore. Her balls pulled tight and she shot into her mistresses mouth, spraying so hard, and so much cum all over her lips, her mistress still fucking her ass and rubbing her cock with her other hand pumping her cum all over her lips, and onto her neck and her tits.



"Oh my you have made such a mess of me! I'm glad you didn't do that all over my silk blouse or you would have been punished. But you still need to clean me up, I want you to lick up every drop from my tits and my neck, and keep it on your tongue, don't swallow any of it. Then you're going to move your head between my legs as I straddle your face and lick my pussy until I cum so hard on your face. I want you to taste both of them mixing in your mouth and then let me taste your tongue" and princess eagerly started licking it up. She had came so much! There was cum everywhere and she needed to lick all over her tits and her nipples, licking every inch to make sure she got it all, and keeping all that on her tongue while she lapped up the rest of it from her mistresses neck was so hard she nearly swallowed it down several times.



Once she was sure she had it all she moved onto her back, adjusting her head so it was right underneath her mistresses pussy and started to lick and suck on her clit, feeling her mistress grind down on her face pressing her pussy down hard, writhing and she licked her whole pussy, all around the lips and flicking her tongue over her clit faster until she felt her muscles tighten and start to spasm. As her mistress screamed out she felt the cum rushing out of her and made sure to lap it all up while rubbing her clit with her hand to keep her cumming, and she felt her spasm again, soaking her tongue so she had a mouth full of her own cum, and her mistresses.



Mistress pulled off of her face, and leaned down to kiss her as the cum mixed in their mouths, princess swallowing most of it down her throat and loving the taste of every drop of it. They kissed until every bit of cum had been swallowed and licked clean from their tongues and mistress leaned back still straddling her, her wet pussy was rubbing against her cock making it hard again. "You enjoyed obeying me didn't you sissy? You're still enjoying it now, I bet you want me to slide your cock inside me and ride you don't you? But you'll have to promise me something first". "Anything mistress, please I will promise you anything if you would let me please you like that" said princess. "You need to give yourself over to me, tell me you will be my sissy little bitch, and you will not only be my princess, but my slut, my bitch, my maid, my footstool if i want you to be, you must promise to do anything I tell you to do, and never question me but always please me, and try to please me harder, and take any punishement physical or otherwise I deem fit for you. Do you understand?"



"Fuck yes mistress, I will do everything you tell me to if you would only let me pleasure you when you want to and I will never question you". Mistress grinned "good sissy. Take me through to your bedroom then, and I will see what you deserve". Mistress picked up her bag which still looked full, and princess wondered what else could be in there! She practically skipped and pranced as she led mistress through to her bedroom. She was very happy to have her mistress to tell her when she was bad, and she would try and be a good princess from now and never be naughty again.

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SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

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. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 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. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

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...

1 year ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

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...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

2 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...

1 year ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

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...

1 year ago
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Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

2 years ago
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I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

1 year 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...

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