Sissy Maid Literotica

Sissy Maid Literotica
Tom Has some choices to make. A phone call. Sarah has been fucked for the first time. How will she react. A Black owned sissy maid greets her Owner's daughter. Second day of housework. Your Mommy Mistress catches you being naughty. and other exciting erotic stories at Literotica.com!
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... 47,723 Views 43 Favorites 4 ...
The sissy maid serves her mother's dinner guests. Conclusion Book 5 Wimp sissified, blackmailed & transformed for black masters. Sissy Jenny discovers Mistress Lizzy's for her. A sissy maid and apprentice dominatrix are punished. and other exciting erotic stories at Literotica.com!
A submissive sissy maid is humiliated and degraded by their Mistress as she prepares for a date with a handsome stranger, leading to a night of erotic degradation and kink. Read this Authoritarian, Transgender erotic story (2,355 words) - Free to read online.
Sabitha's Sissy Maid Pt. 01 A dominant lady fulfills her dream of having a sissy maid.
My character is a stupid sissy maid named Stella. Stella used to me a man, but got in some trouble, and had to sell himself to a group that turns men into obedient sissy servants. After extensive training, Scott and Kim purchased me, to become their sissy maid. This story has scenes of bondage, degradation, humiliation and forced feminization.
Mistress must discipline sissy with the cane and a soap-bar. and other exciting erotic stories at Literotica.com!
This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri... 101,940 Views 90 Favorites 8 Comments 5,821 Words www.literotica.com
Master clearly says, "Yes, Chantel, you were the most prepared sissy girl and gave the most thought and effort to the idea of living in a full time sissy slave position." My head was all spinning inside. I was so excited at the thought of becoming a sissy maid and slut. We began to talk about how things will unfold from here on.
Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel.
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2 days ago
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I truly want to be a "Billie", to watch my wife fuck other men with bigger cocks, eat their cum from her cunt after they leave, dress up in a sissy maid's outfit, and serve my wife and all her girlfriends when they get together to talk about their alpha studs and their cuckold hubbies. Please continue this story.
Jan 18, 2026
Jan 18, 2026
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.
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But yet, five and half hours of sleep was all that she was going to get that particular night. Someone was shaking her awake, and as she opened her eyes, she was a little s... 35,307 Views 3 Favorites 5,103 Words www.literotica.com Recruiting of a Sissy Maid Ch. 04 by Sissy_Chantel on Oct 11, 2017
1 day ago
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I awake to my first morning in my new sissy slave home and life as a sissy maid and slut. I get out of bed, stretch and strip nude for my enema and shower. My butthole still hurts from last night's gang rape session, but I won't protest, nor do I really wish too. In... 32,170 Views 17 Favorites 8,418 Words www.literotica.com
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... 47,723 Views 43 Favorites 4 ...
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Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day.
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As we all enter a small but purposeful eating area for us sissy girls, we first get a tray and a plate and mug or glass. The sissy maids who prepared our basic dinner have the food out for us. Today i... 8,325 Views 8 Favorites 3,772 Words www.literotica.com Becoming a Sissy Maid & Slut Vol. 04 by Sissy_Chantel on Sep 14, 2017
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... 47,723 Views 43 Favorites 4 Comments 4,022 Words www.literotica.com
Sissy training and variations A male sissy wearing a PVC maid dress A subset of feminization is "sissy training", wherein the dominant partner slowly trains the submissive in being a sissy over time, having them take on "ultra-feminine" behaviors and participate in feminine activities. [9]
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And in sissy mode, I'm not passable by any means, but im not an out of shape slob in a bra and panties. Over the years, we have tried several times to find the guy that will work for our lifestyle. While there were a few that worked out for a couple months, no one really stuck out.
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2 days ago
Loved this story,it is close to my life so 100% 5*but I have to agree with jupitercreek that the end was a bit hurried , I love french maid , cuckold stories wi…
I truly want to be a "Billie", to watch my wife fuck other men with bigger cocks, eat their cum from her cunt after they leave, dress up in a sissy maid's outfit, and serve my wife and all her girlfriends when they get together to talk about their alpha studs and their cuckold hubbies. Please continue this story.
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The maids brought up some basic gowns, ankle length, but made of silk. and some kitten heels that looked like slipers with a small heel for them to change into. The guests guided The two of them went down the hallways to the dressing room. Tom scanned the house again thinking to himself that he needs to understand Hannas true intentions.
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Husband told he'll serve wife & friend as secret sissy maid.
Sissy Maid cuckolding. How did I end up losing the use of my Julie's neat tidy pussy and only be good enough to clean it with my tongue. My wife knew I liked to cross-dress but Julie was never really happy about it and was certainly not a dominate person. I had spent many hours online looking at trying to get a Mistress to dominate me and force me to wear a chastity belt full time but to no ...
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With that, my life as a part-time sissy maid began in earnest. I started dusting near the door, working my way around the room and making sure I attended to every shelf, table and other dustable surface.
May 4, 2025
'Sissy-Maid school,' asked Sharon with a puzzled look on her face. 'Yes Sissy-Maid school', the tall lady replied, 'we are going to make it mandatory for all Sissies soon.'
At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, included a couple of vanilla pictures, and was rewarded a few days later with a response.
Sissy Maid Chastity. How did I end up losing the use of my Julie's neat tidy pussy and only be good enough to clean it with my tongue. My wife knew I liked to cross-dress but Julie was never really happy about it and was certainly not a dominate person. I had spent many hours online looking at trying to get a Mistress to dominate me and force me to wear a chastity belt full time but to no ...
Things evolved and it eventually ended up me serving as her sissy maid at home at times when the kids were over parents or friends house and serving as her personal sissy maid for fetish event.
A Sissy Maid is Born Ch. 01Storm realises his destiny is Mistress Arrabella.in BDSM Allyson's First BlowjobAllyson gives her first blowjob, the first of many.in < Page: 1 2 3 4 5 6 7 8 9 10 11 > Literotica Toy StoreAdult toy & dvd store with fast shipping and a great sexy selection Active Tags: sissy maid
We meet each other's parents. and other exciting erotic stories at Literotica.com!
I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...
Sam goes from husband to sissy maid. "Are you sure you want to do this? It's a wild ass fantasy. You're basically saying you want me to dominate you, feminize you and sleep with other men?" Lauren asked. "I mean if you put it like that, it's weird. And it doesn't sound right. But you wanted me to be honest!" I said in tears. I was having this conversation with my wife of 2 years Lauren. We've ...
2: The story begins as a wanting to be sissy, sissy maid and sissy slut story and develops into a deeper sissy maid and slut story with some exciting and hopeful emotional plot twists.
And one of the terms is that a good sissy maid always cleans up her messes." With that, she swiftly moved her hand toward Matt's face and shoved her cum-covered finger into his mouth.
Eve enjoys her new life as a model sissy! David now has some new rules to abide by. Victor's journey continues. Listen to me read your filthy confessions I got fucked at a 70's themed party and it changed my life. and other exciting erotic stories at Literotica.com!
Andy gets caught by his sister in her panties and it's fine.
How you carry yourself physically and your attitude as a maid--and especially as a sissy maid--should be muscle memory," A bead of sweat formed on Matt's temple, just as a drop of precum dribbled out of his cock.
My First Saturday and Sunday at 'The Agency.' and other exciting erotic stories at Literotica.com!
Sissy gets put in chastity and turned into a house maid.
Caught and made to serve as male escort and sissy maid.
I was wearing the slutty two-piece sissy maid outfit that April had laid out for me the night before. The black satin costume consisted of a lace trimmed halter top and a miniskirt featuring a dainty white apron.
The maid of honor, Karen, addressed me first among the maids. "Joyce, would you like to start with Evelyn's nylons?" "Yes!" I answered, perhaps a little too enthusiastically. Karen handed me the package of nylons and a pair of hosiery gloves. The exclusive Muratti stockings were the sheerest fabric that I had ever seen and they were so exciting ...
Story tags portal and other exciting erotic stories at Literotica.com!
The latex sissy maid has the time of her life.
Paul has a secret sissy maid fetish. He finds out he is not the only sissy maid in his town.
From Fuckbuddy to Sissy. Introduction: Just your 'usual' Friday evening. I knocked sharply on the door three times at exactly 5:00PM and waited patiently. I had made the mistake of knocking an extra time after a 5 minutes wait once, thinking she might not have heard me, and the resulting spanking had made sure I remembered that her time was more valuable than mine. Eventually she let me in ...
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