Degraded Sissy free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
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 are dressed in mens clothes you are always wearing stockings or pantyhose with panties undeneath - a sissy should always be free of body hair, have its tie nails permanently painted and wear panties and omens hosiery 24/7. It should not own any men’s socks or underwear.

I cannot advise you whether you should go out and prostrate yourself at the feet of real men. You should certainly start practicing because I think you know, deep down, it’s where you will end up. It is a question of when, not if you will end up serving real men. Come what may, you are on an unavoidable course with your destiny.

You may not find it physically pleasant, but its what sissies are there to do.

When you have sucked you first cock, if you have not already done so, you will tell yourself you did not enjoy it. You feel disgusted with yourself. In a perverted way you will seek an temporarily find comfort in this, in that you tell you slf that this was merely a curiosity; that this confirms you are not gay.

But deep down you will know that it will not be the last time. You heaved passed the point of no return.

Eventually, you will find your made up face pressed into a pillow, maybe your hands shackled behind you, as real men, contemptuously fuck your arse as you are dressed in your girly clothes, with the remnants of your manhood locked away.

You will come to realise that your own cock is useless as a male tool, and its only real function is to be locked away to serve as an abject reminder of the man you failed to be and the woman you can never be.

A sissy should never again experience male orgasm. It can only experience orgasm vicariously through the climax of real men in its mouth and in its anus, but it is ultimately destined to eternal frustration.

When the man is finished, he will not thank you. He will just push your face into the pillow once again, as he gets up and gets dressed, leaving you lying limply, defeated, face down, aching, maybe bleeding, dressed like a woman, with his cumm seeping from inside you.

You have been fucked like a woman, but you are not a woman.

You are a failed man; a mincing, chastised, crossdressing sissy.

You will feel weak, pathetic, impotent, degraded.

You will lie there for a long time, contemplating what has happened. You will know that you are now a sissy faggot. No turning back. Perhaps that was never an option anyhow. But it will be a pivotal moment in your life.

Then you know you have arrived at the nadir of sexual existence. Your destiny.

Once you resign yourself to it, life will become a little easier.

Welcome to the rest of your life.

It is always good to see sissies playing with each other, for it emphasises their position at the bottom of the sexual food chain and that they can only ever be an equal to another sissy - everyone else is above their station.

They can never be a sexual partner to a real man or a real woman. Their job is to serve real men and real women as an animate sex toy when required - nothing more.

However, sissies playing together should NEVER be allowed to consummate that with a sexual climax. Sissies should be kept locked in secure chastity at all times, the eternal frustration is a perpetual reminder to them of inadequacy and failure. Since they have failed miserably to be men and can only seek to emulate, but never be, a woman, they should not be allowed to experience the sexual climaxes that men an women experience.

Sissies should be allowed to feel and taste the intimacy of kissing another sissy’s lipstick painted lips. They should be allowed caress each others stockinged legs. They should be able to feel the submissive denigration of oral and anal penetration. These are effective in reminding the sissy feminized, submissive and compromised position.

But the only contact that should ever be had with a sissy’s genitals is through a chastity device. In particular, the clunking of chastity devices against each other as sissies writhe around with each other in a heightened state of arousal, is a reminder that their arousal cannot be consummated with a climax and will remain unsatisfied. The consequent perpetual frustration is a metaphor for the frustration of never being able to be the man their wives and girlfriends once expected them to be, and never being able to be the beautiful woman they have long craved to be.

A true sissy must learn to savour whatever satisfaction it can from the journey, for it can never arrive at the destination.s


Listen, sweetie.

Once you start wearing makeup and stockings and high heels that thing becomes redundant, other than to remind you of the man you failed to be and the woman you crave to be, but can never be.

It needs to be permanently locked away.

Sissies are not entitled to have orgasms. These are for men and for women. You are neither.

You are emasculated, so you cannot be a man. You are feminised, but can only ever try to imitate a woman.

Sissies may sometimes be called upon to help men and women achieve their orgasms - orally or anally - and to clean up afterwards, but never to have an orgasm themselves.

A true sissy can only ever experience orgasm vicariously, though someone else, and needs to learn how to squeeze some kind of satisfaction out of that.

However, just as a sissy can never be a man or a woman, it is destined to eternal sexual frustration as well. Learn to make the most of the journey, precious, for you can never reach the destination.




This situation makes very clear to the sissy why its cock is redundant and locked away.

While it mixes around pathetically in stockings and high heels, the real man, firstly, screws the sissy’s wife to delirium, and then, sodomises the sissy until it is a limp, whimpering mess.

Before the sissy even has a chance to compose itself, it is pulled up, on to its stockinged knees and, with the real man’s semen still flowing from its behind. It is then forced to clean him and her orally.

The sissy is then left,whimpering in a corner, to contemplate its pathetic state at the bottom of the sexual food chain as its chastity cage remains locked, it sexual frustration never to be relieved.

Meanwhile, the real man pets with the sissy’s wife over a few drinks whilst occasionally laughing at, and humiliating the pathetic specimen.






Sweet Sissygurl

When I a dressed like this I just feel so intensely girly and aroused.

With the remnants of my masculinity securely and permanently locked in a chastity cage between my legs I will never again experience the release that, at least for a short while, allows me to want to take of my women’s clothes a nd feel like a man again.

I feel so malleable like this.

Once this guy has handcuffed me, groped me, humiliated me, emptied himself into my mouth or my loins, I will still not get to experience climax and the release that foes with it.

I will just lie here feeling even more girly, sissy and submissive than before. Where the unchastised transvestite will then climax, dress back into their men’s suit and return to their room, I will go back down to the hotel bar, humiliate myself, luxuriate in the feeling and look of my glossy stockinged legs, absorb the stares and the sniggers.

Eventually, another intoxicated businessman will come over and start to chat me up and seduce me. It doesn’t take much.

The next morning I have to change back into my suit and masquerade as a man again, but the the submissive sissy slut will still be there wanting more humiliation; more degradation.




This is soo frustrating. But a necessity if you want your gurl to stay plyable. Keeping her in chastity is a rule that’s not equal to Lock And Leave. She’ll get used to it and even worse, irretable. By teasing her like this at least once a week you reminds her of two things: who controlls her clitty and what she has given to you.

dominiqueq:

Ladies, when teasing and edging your gurl in the middle of a denial period to build up the denial dynamic to ‘slut delerium’ levels your gurl may become a little vocal, gags can be a necessity in such circumstances, I have found that penis gags often work best.

I’ll bet this feels so good!

It’s been 2 years since your little weenie has been out of its cage and erect.

Yes ., I can see this is ready to blow and you are really worked up or the most explosive orgasm you’ve ever had,

You’re nearly there .. I can sense it.

Tuff!

It’s not going to happen.

What do you think this is?

Men and women have orgasms.

But look at you,faggot!

Dressed up in stockings and heels and a bra,your face all painted like a girl.

You are clearly not a man, but with that thing between your legs, as pathetic as it is, you are not a woman either.

You are a sissy. A transvestite. You exist in the twilight zone between masculinity and femininity.

Sissies don’t get to have climaxes

.

Just as they failed to be the man they were meant to be, and can never be the woman they try to be, their sexual existence is Los one of unconsummated frustration.

So now the chastity cages goes back on.

You are, no doubt thinking why I took it off at all and teased your so cruelly.

Because I don’t want you to get too used to chasity. I want you to be able to remember, but no experiences the p,erasures that are denied you and to know the extent to which I ownandyh control you.

Now I’ll leave you tied up for a while longer to think about it.

But we’ve got the Fergusons coming round for dinner later, so you’ll have to get yourself made up and ready in your maids uniform to serve us


For many would be sissies this appears to be a dream lifestyle.

But be careful what you wish for.

Yes, you will, for the rest of your life enjoy the deligthtlful girlyness if being constantly dressed in stockings and panties and high heels nd frilly maids dresses.

And the notion of being permanently locked into a steel chastity belt is quire a turn on.

But the reality sets in sooner than you think.

After just a few weeks you start to realise that this is not a game. Every morning when you get up, you will dress up in women’s clothes - there are no others.

When you go out, it won’t be to amuse yourself, but rather to carry out chores for your aster and mistress - and it won’t be in men’s clothing, but always the ever present stockings and heels and servants uniform. Whenever anyone sees you, it will be crossdressed in a servile manner.

The stares, the whispers, the double takes will follow you for the rest of your life. No matter how good you get at make-up, people will always know you are a sissy, a transvestite..that devastating word “fag” will occasionally be cruelly whispered behind your back. You will learn to adjust, but you will never quite be able to switch off completely. There will ways be an element of humiliation. The laughs and derision will always strike home income way.

No matter how much people might become accustomed to seeing crossdressers and transsexuals, you will always be seen as something if a freak - a servile, mincing sissy. The lace and frills, tthe bows,the maids uniforms, the petticoats, the overwhelming presence of pink - it is not how real women or ever transsexuals or transvestites dress, The reactions may vary from contempt, to ridicule to pity, but they will never be anything that allows you any slf-respect.

You will not have a moment that belongs to you. You will be at the constant beck and call of your superior.

But what will brand itself on your consciousness more than anything else us the chastity belt.

You will learn to manage the frustration over time, but never to overcome it.

Even when you think the worst is over, there will be days where you lie there, painted, perfumed, in your maids dress, stilettos and stockings, fingering your charity belt just yearning for just a half-hour during which the remnants of your redundant manhood are pushed back between your legs inside a steel tube; during which you could touch yourself, and once again feel the satisfaction of sexual climax.

But you have resigned yourself to the knowledge that that can never again happen. That was your old life. It’s gone forever.

Sex, for you, is something that you experience vicariously through the services you dispense to others.

Yours is now a life if denial, frustration, submission, humiliation and self-loathing.

But it is what you thought you wanted.






This is what I wore to work one day last week. Do you think I’m being naughty?

Honestly, I think you’re being naughty not wearing it all time to work, boy

Darling, I understand that man sissies still have to go to work urging the day and pretend to be normal males, but a good sissy is always encased in, at least, stockings and panties at any time - whether under a business suit, or tradesman’s overalls or whatever. It is required, as a constant reminder that you are not a male, but a crossdressing sissy.



Feminised. Sodomised. Totally emasculated . Humiliated and degraded. Yet there is a strange sense of relief, an inner peace, that comes over you as surrender your pretensions to manhood and lie there, prostrate, limp and pathetic, in women’s stockings and high heels, whilst another man pumps your arse, emptying his men into your bowels. As devastating and soul-destroying as it may be, with surrender and defeat comes the relief that the pretence is over. You no longer have try to be something you are not, and never reall were.

Feminised.

Sodomised.

Totally emasculated .

Humiliated and degraded.

Yet there is a strange sense of relief, an inner peace, that comes over you as surrender your pretensions to manhood and lie there, prostrate, limp and pathetic, in women’s stockings and high heels, whilst another man pumps your arse, emptying his men into your bowels.

As devastating and soul-destroying as it may be, with surrender and defeat comes the relief that the pretence is over. You no longer have try to be something you are not, and never reall were.

It is now almost 12 years since my divorce, after which I threw out all my male underwear and socks.

I have worn panties and pantyhose or stockings almost 24/ 7 ever since.

In fact it is hard to imagine what my legs feel like without the sensation of being encased in sheer nylon,

The longest I am ever not in pantyhose or stockings is for 2 hours every 6 weeks when I get a full leg and body wax and 15 minutes each day when i take my shower. I change in to fresh hosiery every morning after I wake up and again when I get home.

But regardless of how much they have become a part of my everyday life, I am still aroused by the feeling of wearing them and the way they look on my legs.

I still love sitting in restaurants, cafes, cinemas, doctors’ surgeries etc. in my girl shorts caressing my stockinged legs for in full view of everyone. It is such a girly thing to do and just feels so good.

I am still incredibly aroused by the feel of sheer hosiery under my tailored male suit when I am at work.

There are many dimensions to being a transvestite sissy, but, to me, women’s hosiery us the mist quintessential and indispensable element.







Remember the day of your graduation?

Captain of the football team.

Top of your law and commerce years.

The hottest girlfriend on campus.

Now look at you!

Mincing around in high heels, stockings and make- up. A live-in transvestite sissy faggot performing menial chores and being an on-call cum bucket to a another man, and all his mates.

Your body completely shaved.

Your cock permanently locked away. You haven’t experienced an orgasm in years an never will again.

You done half you time in shackles on public display for others to ridicule and humiliate.

You can’t stop it.

You don’t even seem to want to .

You seem weirdly comfortable - even turned on- by it.

You are a bizarre emasculated, totally degraded transvestite slabs to another man.

What do you think the trophy girlfriend and your graduation class would think of you now?





Once this occurs you know straight away that the last frontier to your complete and total emasculation has been crossed - irreversibly.

You have been dressing for years but rationalised it away as a ‘harmless fetish’.

Over time, becauseof its association with the sexual arousal that accompanied your crossdresing, you started to be aroused of the feeling of shame and humiliation that was always there when you crossdressed..

You began to take greater risks - dressing partially and then fully and going out at night; then going to gay bars to be seen; then going to the mall in broad daylight; all the time dressing every more effeminately.

You needed a bigger and bigger hit each time and took increasingly bigger risks to achieve it. It was like an addictive d**g you couldn’t get off.

Eventually, you sucked you first cock. And then another. And another…

You weren’t gay. You weren’t queer. You weren’t a fag (although that word was always wafting around in the back of your mind as you felt the girlyness of being on your stockinged knees sucking off yet another guy.

It was just a bit of role play. Experimentation. Whatever the rationalisation.

Then one day you are in a hotel bar on a business trip.

You have dressed up in a ridiculously sissy satin pink maids outfit, white sheer stockings, pink stilettos, a diamanté collaran andbfrilly sissy panties.

You know it will attract attention. Bemusement. Derision.

But the the feel and look of the clothes and the magnetic, erotic allure of being seen dressed like that in a bar at a hotel at which you are staying proves irresistible.

You are out of town. No one will recognise you.

You have a wine in your room to work up the courage.

Suddenly you are mincing out of the elevator into a crowded hotel lobby.

The friction of your sheer white stockings brushing against eact other is and enormous rush, as they shimmer under the bright lights if the hotel lobby.

You feel your heels are clicking a hundred times louder than they actually are.

You feel that everyone is staring at you.

They probably are. Wasn’t that the point?

You walk into the bar and sit yourself on a stool demurely, caressing your stockinged knees suggestively, but nervously.

An hour later, youve have had a glass too many.

A guy in a suit, who has also had a glass or two too many comes over to chat you up.

You are intrigued but in control and decide to let the situation go through the motions.

Next he is caressing your stockinged knees and the your thighs, then his hand is working your swollen crutch as he thrusts his strong manly tongue down your throat.

You don’t enjoy the sensation of being kissed by a man or the scratching from his stubble, but it all makes you feel so delightfully submissive and girly.

There comes a pint where you realise you are not in control, but you let it go on (as if you have a choice by now, stupid sissy). After all you’ll just give him a blow job and he’ll go away happy.

Next you are in his hotel room.

Before you have a chance to drop to your knees and unzip his fly, he is holding both you hands behind you and forces you onto the bed, face down.

You feel helpless and pathetic. He is so much stronger than you…especially whilst you are in stilettos and dressed as you are.

Next you feel his pulsating manliness ripping into you behind,

It’s painful. It’s degrading. It’s not pleasant.

But somehow the helplessness and humiliation of your situation is intensely arousing, although your cock is locked away in a chastity device, which only enhances the humiliation and helplessness.

Ther is a kind of intense feeling of else if that comes with total surrender.

Next you feel his hot juices filling up inside of you.

You are in tears.

You feel so weak. So powerless.

You are just being used as a pathetic prop for another man’s sexual gratification and you have surrendered and are allowing it to happen.

It is devastating; debasing; emasculating.

Yet so ecstatically arousing. The ultimate girly experience.

As he finishes he pushes your face into the pillow and contemptuously exclaims that word: “faggot!”

Ther it is. What you have always been deluding yourself into believing that you are not.

You know he is right.

There is now no rationalisation that you can hide behind.

He does up his fly an leaves, as you lie there limply; motionless; pathetically. Unable to move a muscle but whimpering and sobbing like a girl.

You know that you have passed the point of no return.

You can no longer be a man. And you know you can not be a real woman.

Suddenly, puff! You are now a sissy. A fag. Forever.

Strangely the realisation fills you with self-loathing and arousal simultaneously. A sense of horror and ecstasy all at once. A paradox you have been graduating towards for some time.

You spend the rest of the night, lying there, face down, crying intermittently, wallowing in your girlyness, his cum,still inside you.

But you remain torn between the agony and the ecstasy.

You wonder where it all went wrong.

But deep inside you know that this is where you were always going to end up.

Sissy. Faggot. For life.






Curious: how many of you Ladies out there would love this to happen in her household?

You know Steve, don’t you sweetie? He’s one of the tradesman in the maintenance department at the company where pretend to be a man and people think you’re important. He’s just here to look after my needs that you can’t service. He tells me he has a little left over and he’s promised that if you get down on your stockinged knees and suck it out for him he won’t tell anyone at the firm about the the emasculated transvestite sissy you are, or that you have been locked in a chastity device for years.




Most men would find themselves strongly attracted to this image and this woman.

As a sissy - a transvestite - I am also very compellingly drawn to it - but in a very different way to real man.

A real man would want to have her.

I want to be her.

I want to look how she looks; to feel the sensations she feels; to exude the sexiness she exudes; to experience the sexual power combined, simultaneously, with the sexual vulnerability she exudes.

I know I can’t be her, of course. But by dressing like her, I can feel the soft, erotic friction she feels through her pantyhose when her legs rub against each other; I can feel the tightness she feels from her bra’s embrace; I can feel the warm caress of her short woollen dress; I can feel the sexy gait imposed by her boots; I smell the sweet scent of her perfume on my body; I can taste her lipstick painted on my lips.

I alo want to feel what she feels when surrenders herself to a man - or a woman.

I have been chaste for some years now and am constantly locked in a steel chastity belt, but one how I feel I can have her in a much more intimate way than any real man can.

I could never climax within her, but I share many of the thinks; she feels and experiences without even touching her or knowing her.

It is a feeling that does not consummate with the orgasmic rush of intercourse.

It is a constant tension and arousal that can never climax or be satisfied, but in many other ways can be far more fulfilling.

Do any of you other sissies, transvestites or crossdressers feel the same way?!

Same as Degraded Sissy Videos

4 years ago
  • 0
  • 51
  • 0

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
  • 0
  • 35
  • 0

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
  • 0
  • 35
  • 0

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
  • 0
  • 30
  • 0

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,...

3 years ago
  • 0
  • 49
  • 0

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
  • 0
  • 27
  • 0

Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
  • 0
  • 22
  • 0

Saturday Morning Sissy

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...

2 years ago
  • 0
  • 41
  • 0

Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
  • 0
  • 29
  • 0

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...

3 years ago
  • 0
  • 28
  • 0

The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
  • 0
  • 47
  • 0

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...

2 years ago
  • 0
  • 20
  • 0

Degraded Assets parts 3 and 4

"Degraded Assets" Part 3 of 6 - "On the outside" By Quiet Savage "In all the above exercises, and after every exercise, please remember to give unlimited praise to your dog. I always tell my pupils to bring the right hand down and scratch the dog's chest after every exercise. Dogs love this, and stay still with a benign expression on their faces as long as you like to continue it." - From "Dog Training My Way" by Barbara Woodhouse "Bunny! Bunny!" she hated him and his pet...

3 years ago
  • 0
  • 37
  • 0

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...

2 years ago
  • 0
  • 52
  • 0

I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
  • 0
  • 31
  • 0

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...

2 years ago
  • 0
  • 33
  • 0

My sisters their friends and me their sissy

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

4 years ago
  • 0
  • 42
  • 0

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
  • 0
  • 27
  • 0

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 ...

3 years ago
  • 0
  • 27
  • 0

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
  • 0
  • 26
  • 0

Curiosity Spanked the Sissy

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...

2 years ago
  • 0
  • 29
  • 0

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
  • 0
  • 26
  • 0

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
  • 0
  • 25
  • 0

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,...

2 years ago
  • 0
  • 35
  • 0

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...

4 years ago
  • 0
  • 39
  • 0

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...

2 years ago
  • 0
  • 33
  • 0

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
  • 0
  • 24
  • 0

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....

2 years ago
  • 0
  • 31
  • 0

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...

2 years ago
  • 0
  • 27
  • 0

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
  • 0
  • 22
  • 0

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
  • 0
  • 29
  • 0

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
  • 0
  • 28
  • 0

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
  • 0
  • 33
  • 0

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...

3 years ago
  • 0
  • 27
  • 0

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
  • 0
  • 32
  • 0

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
  • 0
  • 20
  • 0

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
  • 0
  • 34
  • 0

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
  • 0
  • 28
  • 0

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
  • 0
  • 52
  • 0

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
  • 0
  • 64
  • 0

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...

2 years ago
  • 0
  • 45
  • 0

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
  • 0
  • 32
  • 0

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,...

4 years ago
  • 0
  • 71
  • 0

Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
  • 0
  • 71
  • 0

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
  • 0
  • 42
  • 0

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
  • 0
  • 37
  • 0

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
  • 0
  • 24
  • 0

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...

3 years ago
  • 0
  • 62
  • 0

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...

2 years ago
  • 0
  • 84
  • 0

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
  • 0
  • 46
  • 0

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...

2 years ago
  • 0
  • 51
  • 0

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
  • 0
  • 48
  • 0

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
  • 0
  • 26
  • 0

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
  • 0
  • 57
  • 0

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...

4 years ago
  • 0
  • 53
  • 0

son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
  • 0
  • 24
  • 0

Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
  • 0
  • 23
  • 0

Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
  • 0
  • 28
  • 0

sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

Porn Trends