Humiliating Sissy Stories

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Humiliating Sissy Stories

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by SissyTwinkleToes
on Dec 24, 2019




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Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life.
8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...


I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...


Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried.
She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...


My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...


It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...


Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her.
The e-mail read:
"Hello, sissy slut,
I have decided I wish to go...


To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real.
I've spen...


My wife/Mistress, Heather and I had over the years developed a large repetoire of ways of playing together, with me, of course, always in a submissive role. One of our favorites was her as Mommy and me as her obedient little sissy boy. What a delightful combination of humiliation and safety it created in me.
However, as frequently was the case, she had deci...


I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...


Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it.
Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...


He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...


I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...


I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...


Chapter Three: More Fun and a Deeper Push into a Reality.
[10:15pm]
My phone rings, I look to see who is calling me and I see it is Master Camron. I dutifully answer the call, "Hello, Master, sissy Chantel at your service."
"Hey sissy, I need you tomorrow morning, that will not be a problem I suppose?" He asks.
I reply, "Oh no sir working afternoons or...


After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing.
A wave of awareness swept over me as I sudde...


I faded in and out of consciousness.
My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...


Here is the third installment of a story of loving spouses, the husband a sissy submissive to his Mistress/Mommy. She has invited over a girlfriend to witness and perhaps participate in his humiliation and degradation. At the end of Part II, the women were on the couch and the little sissy was on the floor. He obeys his wife's command to beg.
*
"Oh, please...


A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy.
*****
Chapter One: The Journey Starts.
Well another night and here I sit dressed in m...


I spent a tension filled week on edge. I was easily distracted from even the simplest of tasks as the memories of my adventures in the parking lot with Those People continued to haunt me. I fluctuated between arousal and disgust as visions of my performance played over in my dreams both waking and while a sleep. I had become nerve rattled, jumping at every s...


Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

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Story Tags Portal humiliation and sissy
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See all models online at LitWebcams
The sexual adventures of a submissive sissy.
Sissy has a fourth threesome with bondage and beating.
Miss Sarah's party finally gets underway.
The summer Christmas party gets a little out of hand.
Sissy has a second threesome involving rimming and piss.
Husband cuckolded side by side with his wife.
Michelle's long night continues, but he learns her lesson.
Markus pursues Shireen. Darius fully embraces sissy slavery.
All contents © Copyright 1996-2022. Literotica is a registered trademark.

How many of you sissies enjoy slathering on that smooth, creamy, lipstick. For some of you that is your absolute FAVORITE part of getting all femmed up.
While so many girls and sissy girls clamor over the 50 shades of grey…THIS sissy falls over 50 shades of RED. This is what she had to say about her red lipstick:
I really love putting on and wearing women’s lipstick. It feels so smooth and sexy on my lips. The way is glides across them creating a slippery, shiny coating. It can never be a light shade, it always has to be a dark slutty color. The kind that stains my lips when I’m wearing it so I might not be able to hide it the next day.
To be a man wearing tons of bright red lipstick is embarrassing and exhilarating. But the feeling of it on my lips, the smell, the taste. Makes my heart pound in my chest.
The latest one, a color called “Tempt” is long-lasting, but also has some lip plumper in it. It makes my lips tingle as they become more pouty and the color sets into my skin.
Mistress Lillith loves making me put on tons and tons of it, making me ask repeatedly for more and more until I can not take it anymore. Then she makes me add more still.
I love that she is turning me into a helpless sissy lipstick addict for her amusement. I can’t resist the feeling when she tells me to “put on LOTS more” .
I fear my future as a lipstick slut, but I also can’t help but love the idea of having constantly red and shiny lips for everyone to see what a naughty little lipstick slut I have become for Mistress Lillith.
That was a lot of femininity to absorb and that shot in the arm toward the end helped me recover a little.
There’s of course another possibility–one that is deeply erotically humiliating–but I still suspect my gut instinct interpretation was correct.
My legs and chest feel different. Actually super weird is more apt.
It’s the strangest sensation but I swear I feel like my legs are wet all the time, like I’ve just gotten out of a pool. Does hair soak up moisture or something? Actually I think what’s happening is in the past when dry, the hairs protruded a bit and on contact with something they would trigger the nerve. Previously when getting out of water the hair would be weighed down by the weight of water and pressed flat against the skin, and wind or something else would trigger the nerve. Now without hair, any brush against the skin is triggering a sensation has historically been associated with wet hair and my mind is confusing the two. At least I think that’s the explanation but I’m not sure. I keep reaching down to brush water off my legs but they are dry and smooth. WHAT IS HAPPENING!?
The strangest, most surprising thing I still quite can’t get over though is my stomach. It’s like I don’t even recognize it. I look down but I’m still not quite convinced it’s my stomach and my belly button. I can hardly keep my hands off of it, feeling the smooth foreign skin over and over again.
For the first 18 hours a red bump appeared in place of every single hair that was ripped out.
Jessica assured me those would recede and they did.
I have smooth hairless skin from my neck down (okay, my arms still have some fine hair and i didn’t have my armpits waxed or my bikini line).
While my shoulders are a little broad, I don’t quite have the physique of a masculine male… Not many muscles anyway.
I’m acting and behaving girlier too : getting waxed, chatting about skin care with a pink haired girly girl, shopping for girly skin care products.
Something that’s kind of turning me on too is that the mantras feel different now. They feel … more effective and more real. Something about looking girly and doing girly things and having it repeated in my head is powerful.
It’s been a deep, erotic fantasy of mine for more than two decades to have hairless legs and a hairless chest. Always fantasized, never realized. That limit has just always been too far and out of reach. Until now.
My legs, chest and boobs look so much better too.
It’s amazing what can happen when all the sissy puzzle pieces fall into place.
One of the exciting things about being on sissy diaries and being exposed – is that it’s permanent. There was a time that I would take things down if asked nicely, but not anymore. You asked for exposure – and that is what you get exposure.
Now, we get to learn about Sissy Diane. We will be getting to know her together as we start HER sissy exposure journey, but – any sissy that wants to play in the sissy spotlight, is FUN by my standards.
Roy Bourne is from Tavistock, Devon in the UK. Sissy Diane is her true identity. I always view the masculine name as the mask – with the sissy name being your TRUE self. It is interesting to me how many sissies are married to someone that doesn’t know, or acknowledge or accept their sissy lifestyles. In this instance, Sissy Diane says, her wife doesn’t know. 
“I have hidden away for years as a closet sissy I am on Internet.
I want to be exposed by you so I cannot comeback and remove my exposure.
I love dressing and wearing make up. I am also into bdsm
I love bondage . Impact play . Forced feminisation .
I love sucking cocks and receiving anal which I have done a fair bit in past with fellow sissies and crossdressers .
I am totally submissive and a total bottom man.
Secrets I hide nobody really knows what I have done or do regards crossdressing at all other than people I have spoken to on various sissy sites i.e. Tumblr twitter etc.
I get a thrill from seeing my pics on internet .”
The internet is forever Diane. Even when posts and pictures are removed there is no telling who saw or if someone right clicked and saved. There are archives that save these pages as well and so nothing is fully removed.
Its fascinating how many exposed sissies there are on the internet. They hide in plain sight and yet are rarely seen by those closest to them.
I’ve seen countless pictures of Phyllis Laday – she is a beautiful blonde sissy that looks FANTASTIC in red. You could never convince me that she was EVER a ‘Phil’ – There is not a bone in my body that would ever believe her to be Phil from Northern California.
She will always and forever be Phyllis Laday
The world needs to know of this Sassy, Slutty Sissy – Half would be in awe, the other half will be lining up to get their cocks sucked by her. Many truckers have wiped smeared lipstick off of their cocks from the cock gobbler, Phyllis Laday.
I’m a mature cross dressing sissy in Northern California that needs exposure. I try to pretend to be Phil a strait male in my vanilla life but the fact is I love to make myself pretty from head to toe and enjoy dating masculine men that are into sissies(can’t believe there are so many men into sissies) and having sex with them.
I started out by just posting a few pics of me on AOL and was amazed how many men commented on me and sent me phone numbers and emails and it excited me. There was one local guy I met in a chat room that wanted to meet me real time. I didn’t think I was gay at the time but thought it wouldn’t hurt to try it with a man one time…..wrong. To make a long story short I’ve kinda lost track on how many men have used me and I’ve become an excellent cock sucker and can even deep throat most men.
I’ve met men through craigslist ad, cross dressing and meet up sites.
One of my favorites is getting a hotel room near truck stop and dressing up like a slut and cruising and trying to get picked up by horny men.
I also love adult book stores with video arcades and glory holes.
This kinda scares me as people that know me wouldnt believe I such a faggot and has caused me to purge my things sometimes and try to be a man again but it doesn’t work. I was probably meant to be a Sissy as I have a very small cock and only one testicle and was never very good at pleasing a women anyway.
I’m married, she knows of my cross dressing and not supportive. She doesn’t know but suspects I may have been with men. We are friends, but our relationship is sexless as she is not a sexual person and I’m inadequate in the bedroom. A lot of this has to do with my brain being reprogrammed to my true self as a bottom sissy for men.
I feel I may have become totally gay now.
I want to tell her but not sure how.
Maybe, if Mistress Lillith keeps exposing me I may get caught and have no choice. Most people would be shocked to know I do this and it shocks me also. The exposure scares me but excites me too.
There is no turning back once I’m exposed and I’m starting to see my pics all over the internet so much that it now has me thinking of how I’m going to explain myself.
I love to expose my sissies. It brings them attention and excitement. When I post it on my blog, it is forever. Phyllis Laday knows this, accepts this and is ready to take the next steps into exposure.
She may purge, she may toss her wig and cut up her thongs. She may attempt to erase all trace – and yet, it will always be…RIGHT HERE. Front and center, just like a cocksucking attention whore sissy needs.
You may find that woman stunningly attractive. But you aren’t having images of wooing her. Are you? You aren’t picturing being that perfect man in her life. You would much rather walk up to her and strike up a conversation hoping that she notices your fresh set of nails you just had done earlier. You want her to ask you about your nails, ask you about the attire that you have on – did you get a new dress? Who did your hair today? That is a fantastic pair of shoes!
You want to have girlie girl conversations while looking and feeling like a girlie girl. You want to BE one of the girls.
This high that you get from wearing and looking like the perfect sissy – needs to be…permanent. That feeling that you get when women are asking about your mannerisms and about your clothing choices and about your overall sissy style, look and feel – needs to stay. Not just a ‘boring Friday night’ kind of feeling.
For Sissy Tara of Chicago , she is the epitome of what a sissy should be. Look at her poise, look at her grace. She takes time and actually walks the walk. She does live a double life. Wearing panties and thongs under her ‘man clothes’ during the work day and donning lipstick and playing with dildos at night.
On special occasions, she will get herself dolled up and go get profession photos done of herself. Living life as a sissy. Out in the open. Knowing that those pictures may not always stay a secret. Honestly, why keep them a secret? Sissy Tara is FANTASTIC and NEEDS THE SPOTLIGHT . She needs to put on her highest heels and scream from the roof tops that she is a fabulous sissy and loves
You can tell in the photos how fantastic she feels. She really…opened her self up…in a few of them as she bounced up and down on a bright red dildo.
Sissy Tara is probably one of the most genuine sissies that I have had the pleasure of speaking with, and now the pleasure is all mine to shine that spotlight on her and give her the exposure she so rightfully deserves.
She is around twitter, I know I’ve seen and retweeted her pictures in the past. If you see her pop up, retweet it. Show her off and expose her. There will be no hiding in the shadows, not any more and certainly not for this sexy and fun little sissy.
Spring is in full swing and before we know it…it will be summer! I always say that the summer is the season of the sissy.
Summer time is when you get to see the tiny little short
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