Mom Punishes My Sissy Cock free porn video

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Story about a sissy boy who is punished by his mother for being such a pervert.
Note from Pussyboy – this is the story that was the inspiration for my video and picture gallery session with the same title.
Mom Punishes My Sissy Cock
Why did I feel such pleasure when my mom humiliated me like she did? It was a question I had asked myself many times before and here I was asking it again as I stood before her naked, hands behind my back, my cock hard as a rock in anticipation of the punishment she was about to give me. Did I secretly like being sexually punished and humiliated like this?

'You snivelling little pervert!' my mother said contemptuously. 'Look at you! That pathetic little clitty cock of yours would never satisfy a REAL woman.'

She had sat back in the armchair hurling verbal abuse at me for over ten minutes. I was 31 years old, but since having my divorce and living back at home, Mom had taken control of my sexual desires and she knew my every weakness, desire and perversion.

She had never been a classically attractive woman, even when younger. And now she was in her 60s, she really looked her age. But to me she was beautiful and no more so as she had got older. Her laughter lines, the age spots on her hands, her big breasts that sagged and flopped all around and her delicious and prominent shaved pussy and her fat, fleshy cunt lips -- I loved all of her just as she was.

Today I had come home from the office and found her dressed in a black slip with a deep lace hem and trim abound her bust. Underneath she wore matching suspender belt, shear black panties and fully fashioned tan nylon stockings with high stiletto heels, but no bra, her ample breasts were loose to simply fill the lace cups of the lacy slip. I could see her nipples harden beneath the flimsy material.

She had instructed me to get undressed and buck naked in front of her there and then. I knew I was going to receive some sexual punishment and if I endured it, my reward would be to be allowed to adore and worship her body afterwards.

Now she leant forward and slapped my swelling erection hard with her hand.

'Pathetic!' she announced again. 'How many times have I told you not to look at pictures of other women on the internet when I'm not here? Tell me!'

Again I felt her hand lash out and hit my growing erection.

'I'm, I'm...sorry mom,' I said stammering.

'Sorry isn't good enough son,' she said. 'You keep doing it. I'm going to have to teach you lesson.'

'I know mommy,' I said looking down guiltily at my feet.

'A regular spanking is too good for you. You still haven't learnt not to leer at pictures of other women when you've got a perfectly good mom to take care of all your needs. So I'm going to have to teach you a REAL lesson this time aren't I? You need a COCK SPANKING'

'Yes mommy'

'I'm going to have to punish that girlie sized CLITTY COCK of yours -- make it very sore so you can't play with yourself when your mommy isn't looking.'

Her hand slapped my penis again. 'You're hurting it mom!' I yelled.

'Of course I'm hurting it you silly little boy! That's the idea and Mommy knows how to make you feel like a very small boy doesn't she?' she said with a thin smile. 'If you think you're too big for a punishment from your mom, think again my boy! Put your hands on your head!'

I did as I was told and she took hold of my balls. She dug her blood red manicured nails into the folds of my scrotum. I visibly winced and cried out.

She laughed. 'No good you making a fuss son, you're only getting what you deserve.'

Tears welled in my eyes as she rolled the loose skin on scrotum in her fingers and dug her nails in again. It wasn't the discomfort, it was the humiliation of being ridiculed in this way and us both knowing I actually loved the shame she made me feel.

'Pervert! That's what you are,' she said now digging her nails into my hardness. 'You are a pathetic mommy-loving pervert! And this nasty mommy of yours is going to show you what happens to pathetic little pussy-obsessed boys like you. They get punished! Do you hear?'

'Yes mom,' I said meekly, feeling more and more uncomfortable by the second, knowing my punishment was about to come. “Give me the punishment that I deserve.”

Beside her chair was a little table. On it were all the instruments she would use to punish my cock. She reached for the wooden ruler. Still clasping my balls in one hand, she brought the ruler down hard on my erection.

Swack! And again. Swack! Again and again she brought the ruler down hard on my rigid penis and dug her nails into my scrotum.

'Tell me what your mommy loves,' she asked as she hit me down there again. 'How can you make her happy?'

'Mommy likes her pussy licked.'

'That's right son, she does. Are you going to go down on your knees and lick your old mom's pussy?'

'Yes mom, yes...you know I love to serve you that way every day.'

'And are you going to be mommy's little toilet helper? You know mommy can't hold her wee wee like she used to.'

It was a question she needn't ask. My pussy licking pleasure was always heightened when she squirted her piss straight into my mouth. Being made to drink her piss was the ultimate humiliation -- or so I thought.

'Yes mom...'

'Yes mom? YES MOM?' she yelled. 'Pervert, pervert, pervert! Tell me what you are!

'I'm a piss drinking pervert,' I said, tears now beginning to tumble down my cheeks.

'Yes you are you pathetic little slut!' Mom said with angry yet lustful eyes, lashing out with the ruler on my erection again, bringing it down as hard a she could. I cried out. I cried in pain and in love. Pre-cum splashed onto her stocking clad knee.

'Oh that's disgusting, your clitty cock is leaking!' she said turning and put the ruler down on the little table. Picking up the pinwheel she said 'You're going to pay for making that mess on my stockings.'

This cunning device had a little wheel with pointed edges set in a plastic handle. Mom clasped my testicles again and ran the wheel over my hard cock. I wriggled and instinctively brought my hands down to stop her.

'HANDS ON YOUR HEAD!' She shouted as she brought the wheel onto my ball sac. The sharp little points of the wheel dug into the tender flesh.

'Please mom, no...please don't, you're hurting my cock.'

'Shut up!' she snapped and continued to punish me there. 'You have such a pathetic little girl sissy clitty cock. I've seen babies with bigger ones than yours! Let's see if we can make it get any bigger with the help of the clothes pins.'

She took a handful of wooden clothes pins from the little table. Placing them in her silky lap, one by one she placed them onto the skin of my scrotum. I squirmed with discomfort as she placed twenty in total, arranging them so that they formed two neat rows all along my cock and balls.

'Lie down on the floor because now your cock punishment really begins!'

I obediently went and lay down, hands passively by my side, my erection standing proud with a line of clothes pinss on my balls.

She stood up and took a small whip from the collection on the table. It had short, thin strands of rubber and she had made it herself from old windscreen wipers. I knew what was coming next – a COCK WHIPPING.

She lingered for a moment, standing directly over my head so I could clearly see her fleshy fat pussy lips through the shear black lace panties under her slip, the mommy twat lips that I knew I would soon be licking. I could see the gusset was soaking wet. Then without warning she brought the rubber whip down on my cock and balls. I yelled out, but this only incensed her.

'You will not wank yourself off looking at pictures of other women you little pervert. Understand?'

'Yes...mom...yes...' I said trying to cover my sissy cock and balls from the onslaught.'

'GET YOUR HANDS AWAY PUSSYBOY, I’M GOING TO WHIP THAT COCK!' she shouted. 'PERVERT, PERVERT, PERVERT! I'LL SHOW YOU WHAT HAPPENS TO A FILTHY PUSSY LOVING SLUT LIKE YOU!'

The whip came down and down and down, the blows expertly placed as the ends of the rubber lashed the tender flesh of my hard exposed cock and caught the two lines of clothes pins on my cock and balls. I was now sobbing openly, not because of stinging sensation in my penis, but because I knew I wanted her to treat me like this. I wanted to be hurt and humiliated by my own cruel mother, this was what I needed so badly because perversely it made me so very happy.

She stopped and stood up straight, towering over me. 'And don't think I don't know what pictures you've been looking at! If loving your mom's pussy wasn't enough of nasty, deviant thing to do, you've been looking at women with cum dribbling out of their pussies. My sissy faggot pussyboy son wants to eat creampies from freshly fucked cunts!'

How did she know? I thought I'd managed to hide it from her on the computer. It was all too pathetically true, I had been fantasising for some time now about licking another man's cum from her pussy and wanking over them when she was out.

'Do you think your mom is too old and too unattractive to be fucked by another man?' she asked.

'No mom, I don't...'

'Well you'd be right son. Mommy can hardly feel your stupid little cock inside her pussy it's so tiny. So while you are out at work, your mom has to have sex with real men. Men with man-sized cocks, not girlie sized ones like your pathetic little dick. Men with big black thick cocks that can REALLY satisfy a woman like me.'

She lashed out with the whip again and I started to cry again. 'Yes mom....'

'Men with big and hairy balls that a woman can feel slapping up against her as they fuck her. Men who've got lots of hot sperm they can pump deep inside of your mommy's old pussy.'

I looked up at her aghast. What was she telling me?

'Yes son, I know all about your perverted little fantasy so mommy's got a nice creamy treat for you today,' she said grinning wickedly as she raised her slip and hooked her thumbs into her black lace panties. Slowly she peeled them down to just above her stocking tops. Then she put her fingers under the gusset and showed me what was there...a big blob of congealed spermy cock cream oozing from her pussy.

'Get on your knees my little sperm eating slut!'

I struggled to get up, my cock and balls aching from the harsh treatment they'd just received by her hand, the clothes pins unnaturally tugging on my scrotum to make it feel uncomfortable.

On my knees, I was eye level with her pussy and the heavily soiled lace panties.

She pulled the hem of the slip up so that I could clearly see her pussy and then reached down to grab her pussy lips to pull her cunt wide open so the fuck slop started to drip out of her freshly fucked twat, then she said 'So son, you'd better get licking...you don’t want to waste any of that fresh cock cream.'

I stared at the fuck mess left by another man, thick dollops of sperm that had dribbled out of her pussy onto her pussy lips and her panties. Could I do it? Could I make my fantasy reality?

Moving my head forward I took in the smell, the very familiar smell of her pussy, which was now tainted by that of another man. Then I opened my mouth and went to tentatively lick the spunk. She didn't wait for me to perform.

Instead she started laughing as she roughly pushed my head into her cunt and the wet panties, then smeared the sticky goo all over my face -- over my lips, under my nose and in my eyes. I could not felt more humiliated by her.

Grabbing a handful of my hair she pulled me away and pushed her panties down, taking them off. Then she sat in the chair, legs wide apart, fully exposing her pussy, evidence of her lover's cum all over her prominent pussy lips. Kneeling still, I moved forward to her pussy and gingerly kissed her inner thighs above the stocking tops -- something I always did at her insistence as a mark of respect.

Then she said, 'Just stop right there son. Look long and hard at my pussy. That was well and truly fucked just half an hour before you came home. A nigger buck, with a big black, fat eight-inch cock took me. And as you're going to find out, he's a really good cummer too. His sperm is really thick and creamy and he regularly pumps hard it into this hot, sex starved pussy you so love to lick.

'So son, time to show mommy how much you really love her and to you put your nasty...dirty...and sick little fantasy into practice. Lick my pussy clean! Lick HIS cum out of my mommy cunt you little sperm slut -- every last little drop!'

I buried my head into the wetness of her pussy and I tasted him. His sperm which had a taste I'd never experienced before, all mixed up with her scent and taste. It was a heady cocktail. My cock and balls ached from the clothes pins, my cock and balls sore and tingling from the whipping as I lovingly scooped out spunk with my lips and tongue. 'Deeper slut!' she commanded. 'Get your tongue right inside my fuck hole.'

Doing as I was told, I pushed my face hard into her pussy, stretching my tongue as far as it would go inside of her, deeply humiliated by the experience. Suddenly she grabbed my hair, pulled me up sharply and then slapped my face.

'Do it properly and gently, I'm still sore there.'

She roughly pushed me back down again and I continued with my sordid task of cleaning his sperm more thoroughly and slowly.

After a while I heard her breathing quicken and l licked more vigorously, my tongue now focused on her clitoris. I glanced up at her, my magnificent, powerful and domineering mom who I wanted to please so much and could see her eyes had closed, a contented smile on her lips.

I was happy because I had made her happy and I licked and licked for all I was worth when suddenly her orgasm exploded. Mom let out a load groan and her body shook from head to toe. This was probably the most powerful orgasm I had ever seen her have.

She grabbed my hair again, my cue to stop licking her and she just held me there, my face pushed hard against her shaved pussy, my mouth open at her lips. And then it came in a hot torrent. Laughing to herself, she let a stream of hot piss spurt straight into my mouth. I swallowed as much as I could, gulping the fountain, a fountain that never seemed to end. When the flow of piss finally became a trickle and then ceased she grabbed my hair again, pulling me away.

Looking down at me she smiled. 'Time to show your mommy what you can do, stand up! Hands on your head!'

I got to my feet and standing in front of her; she slowly began to pull off the clothes pins one by one. In my concentration to please her, my tiny cock had gone limp.

'Look at you!' she said with a sneer. 'You can't even keep it up you pathetic little pervert! Ashamed were you, ashamed of having to lick another man's cum from your mommy's pussy? A real man's cum? Put you hands behind your back!'

While they had been attached to my cock and balls, there had been discomfort, but as she roughly removed the pegs, so they became ultra sensitive. Every yank on a pin made me cry out aloud as the contracted skin sought to regain its shape. But in spite of the pain, my cock was growing rigid again -- just as she knew it would. With the last one off, she cupped her hands around my cock and balls and rubbed then. I cried out again and very loudly.

'Oh, you poor little baby, let mommy kiss it better.'

She moved forward to sit on the edge of the chair and guided my painful cock into her mouth. At first her saliva and tongue soothed my aching and sore penis, even if her hands still made me wince with pain at her touch. But then she suddenly bit my hard cock. Not enough to damage me in any way, but sufficient for me to feel it. She continued to roughly chew on my hardness and my foreskin like a piece of old fuck meat.

I could take it no more; uncontrollably and spontaneously I shot my load into her mouth, filling it with my hot sperm. Without further ado, she stood up and planted her lips on mine. She gave me a long and deep kiss, depositing my own fuck slop into my mouth. When she pulled away again, she simply said, 'Swallow your sperm you little slut. Swallow ALL OF IT!'

The deed done, we retired upstairs to her bedroom. Still naked I lay beside her on the bed. She pulled down one of the straps of her slip to expose one of her beautiful breasts. Pulling me to her nipple, I suckled her milk bag tits and proceeded to cry my eyes out in joy and happiness. I really liked being my mom’s sissy pussyboy bitchcunt slut.
The end

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

1 year ago
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Sissy spit roast sleep over

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

1 year ago
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Landlady punishes David

It was with considerable trepidation that David walked up the garden of this neat suburban semidetached house and knocked on the door. In all his 22 years he had never lived away from his home or away from his mother and elder sister. Now, having moved on promotion with his company he was about to meet his new landlady at his lodgings arranged by his company. She opened the door and David was met by an imposing lady in her mid forties, she stood very straight, wearing a blouse which strained at...

2 years ago
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The SissyMaster

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

2 years ago
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The Sissy App

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

3 years ago
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A Sissy called Jezebel Part VIII

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

2 years ago
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Adult Sissy Little Girl World

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

4 years ago
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Forever Her Sissy Chapter 6

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

1 year ago
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Training Sissy Michelle

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

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

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

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

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

2 years ago
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Good Sissy Girl

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

3 years ago
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Sissy School Part 3

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

2 years ago
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Sissy tasks

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

4 years ago
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She Found a Sissy

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

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 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 School Part 4

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...

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