Sissy Maid Cuckold Stories

Sissy Maid Cuckold Stories
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He becomes a maid and sex-slave for a dominant couple.
How I went from a loving husband and to a sissy for my wife.
How I became a sissy maid & slut to a Master, vol. 1 Ch. 1-3.
Nick started college in a school of his mother's choosing.
Married sissy in for the experience of her life.
My submission to a dominant couple continues.
A journey into sissy slut play then sissy lifestyle.
Candi's time as the party maid ends with a demonstration.
A son is forced to become his mother's own sissy maid.
Wimp sissified, blackmailed & transformed for black masters.
Chapter 2 of this Mistress wife, sissy husband, lifestyle.
Chantel finds sissy fantasy will become her sissy reality.
A sissy maid prepares to entertain his owners' guests.
Allyson gives her first blowjob, the first of many.
Chantel moves deeper in life as a sissy including slut work.
Wife's sexual frustration leads to her taking control.
To become a sissy maid and slut to a Master, Vol. 2 Ch. 4-6.
The beginning of of a sissy's recruitment.
My new sissy life to my Mistress wife grow more entrenched.
Sissy gets used by the inexperienced guests.
I begin my career in sissy pornography.
Jenny continues to prepare with Mistress's help.
Initiation turns out to be more than Andrew expected!
The sissy maid is getting prepared for her first day.
Sam suggests a way for Jean to cuckold her sissy more often.
Part 2 of Sissy Chantel's decline into a sissy lifestyle.
Sissy Jenny discovers Mistress Lizzy's for her.
Sissy maid Melody gets a surprise from her wife.
House sissy starts to take her role seriously!
The sissy maid serves her mother's dinner guests.
A good deed gets an unexpected reward.
To become a sissy maid & slut to a Master Vol. 3, Ch. 7-9.
Middle age subs fantasy girl becomes an extreme reality.
Part Three of Sissy Chantel's decline into a slut.
Sissy gets put in chastity and turned into a house maid.
Sissy gets fucked by Sarah's bull and learns about pain.
Sissy slut used for guests' entertainment.
Debroah finally agrees to dominate her husband.
Continuation of Sissy Chantel's decline into a slut's life.
Erin considers Michelle’s sissy cuckold arrangement.
More on my sissy journey, this is vol. 4 and will be Ch.10.
A cuckolding couple try it for the first time at home.
Oliver's father's humiliation continues.
Chantel moves on to contracted out maids work.
Sucking cock, public humiliation and a good butt fuck.
The house sissy continues her initiation!
More becoming a sissy maid & slut vol.13 chapter 22.
Part four of Sissy Chantel's decline into a sluts life.
Becoming a Sissy Maid & Slut, Vol.5, Chapter 11.
Sissy Chantel serves and services two Dominant men.
Becoming a sissy maid & slut, vol. 6, Chapter 12.
Chantel, Helen & Alan Celebrate her role as a transsexual.
Chantel, works as a classy t-girl escort now, lots of fun.
More, becoming a sissy maid & slut, vol.10 Chapter 17.
Tom caught cheating on wife. May not like wife’s solution.
A hot Hawaii Honeymoon and a future together.
Anna gets second chance. Is stripped and "reborn".
Oliver's father has some fun before work.
Some dressing and make-up and a three-way.
More becoming a sissy maid & slut, vol.11 Ch.18-19-20.
Chantel and Mikel are a couple in love, fun Christmas Party.
Part 6 of Sissy Chantel's journey into becoming a slut.
More becoming a sissy maid & slut, vol. 7 Chapter 13.
Mikel & Chan go a music concert and more.
Chantel arrives at The Jade Maid Club.
More becoming a sissy maid & slut, vol. 8 Chapter 14.
Chantel goes on a date and finds a new Beau.
Chantel lovingly tells Mikel what she wants.
Another Hookup with Master, Chantel's life begins to change.
Chantel has her big surgery, true love is shown.
Moving on with my life at 'The Agency'.
The Wedding and a very Special Night of Love Making.
Sissy Alice prepares for her master's return home.
Baroness Maria has many slaves. None are irreplaceable.
Chantel meets Jack and things are great between them.
More becoming a sissy maid & slut vol.14 ch.23
Domina moves forward in plan to take a lover.
A full shift to pull today and tonight.
A sissy maid and apprentice dominatrix are punished.
Domme gives him more than he bargained for, but just what he needed.
Jake returns home and is greeted by Sissy Alice.
High Heels, Butt Plug & New Schedule For Sissy.
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"... with nice partners. As I said, it is amazing role-playing in "Torment"... I gotta go, bye!" - you end your chat about new amazing RPG you played last (whole) night, put cellphone aside and return to your work. You don't notice that someone looked at you with interested.
Later, when a lot of people left, one of the colleagues approach...

Erin Ch. 15: A Perfect Sissy Cuckold
By Jonathan Quincy Graves
{Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story.
*
I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

Chapter Three: My sissy maid lifestyle becomes more set in reality.
Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Oscar could smell her vaginal juices from his proximity kneeling between her legs. Her delicious cunt beckoned his waiting mouth.
"I do need to warn you dear that I'm a squirter!" Bea cautioned. "Once my floodgates are opened its head for the high ground!"
"Let it pour!" Oscar replied as he buried his face deep between her thighs and tasted he sweet guim....

My wife and I was playing dress up, it's a game we usually play before sex. I dress her in a sexy outfit and then we make love. She has a vast wardrobe of sexy lingerie and other various items of clothing that I get to place around her very sexy body. I also have different types of underwear that I wear at these times such as thongs or other sexy briefs. Thi...

Part 2: Homecoming
Author's Note: These stories are completely true. My wife has helped me write these stories not only to share with the world, but to also help relive the past steamy sexual encounters she has partaken in.
On the week before I was coming home from my first deployment, my wife Mary told me she had a surprise for me when I came home. I kne...

{author- I tried to give my level best to all of you reader, if there is some mistakes I am sorry please give me feedback to improve my self, and also add some chapter to make it more interesting.}
Hai , I am Rachel
I am 19 year old, I used to see lot of porn and I want to try everything in sex, I became a sex addict and all I could able to think is sex, coc...

Now that my daughter was of age and her mother had enlisted her help to cuckold me she made a plan to include our son upon his return from college. Jason was 21 years old and Chrissy was 18. I really didn't think that Jason would be up for having his daddy suck his cock or offer his ass for the fucking. I guess we'll find out I thought as Friday approached a...

Mr. Sarun visits us and stays for a week, enjoying my wife's hospitality. – Rajesh
Author's note: This is a story of a cheating wife, of adultery, of cuckoldry and small penis humiliation. If that is not your thing, skip this story. And remember while adultery can be a great source of enjoyment in fantasy and erotica, in real life it damages souls and dest...

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked.
Oscar looke...

MMM's HotTub Party & Cuckolding ricki
MMM had not been back to Oregon for over 8 months and was anxious to spend some time with her best girlfriend Jill and her significant other Roger. Mary was sure that Roger had a crush on her and was anxious to take things a little farther if Jill approved and Mary made the opportunity occur.
MMM had been training her...

November is fast approaching which means NaNoWriMo season will soon be upon us. For those that don't know about it NaNoWriMo (National Novel Writing Month) is a creative writing challenge whereby a writer tries to write a 50,000+ word novel in the month of November. Our challenge here will be a different one but in the same spirit of encouraging writing and...

My wrists strained at the ropes that bound me to the chair. The vibrator taped to my cock was driving me mad while I watched my leather clad bride mount her lover's huge black cock. Angel smiled at me teasingly, knowing the pleasure and pain I was experiencing....
Suddenly I heard her key in the door I quickly turn off the magic wand, put it in the desk dra...

This the first installment of a series about an upscale couple and a black man.
*
My name is Wayne. I am a 56 years old executive in a prosperous publishing company, more precisely the CEO. My wife Beth is 45 years old. She is a university teacher and researcher. Her field of work is history, her specialty being the history of black people in America. She...

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax!
*****
Dominant girlfriend wants a black lover, deluded b...

Characters:
• Linda, hotwife, 33 years old, a tight & fit yoga instructor of Mediterranean Italian heritage with olive skin tone and long, luscious, brown hair, and curvaceous proportions. Linda has an insatiable sexual appetite, has always dreamed of a manly man, but learned only after marriage that her husband held cuckold and sissy tendencies. Loves her...

My wife, Mindy, had discovered my secret stash on interracial cuckold porn on the computer. Rather than getting mad we decided to explore the fantasy. With each new adventure my wife came closer and closer to being fucked by another man's cock. I knew I could stop it at any time and that was the danger of the game, the ability to stop and not doing so. Now s...

I've tried to categorise stories although some stories will inevitably cross multiple categories.What's next?
The Company
Gullible and Naive
Power, Exploitation and Blackmail
What's next?
The Company
Gullible and Naive
Power, Exploitation and Blackmail...

You must be at least eighteen years old to view this content. Are you over eighteen and willing to see adult content?

This is a continuation of the story of Becoming a Sissy Maid .
I couldn’t believe it, but I was starting to look forward to being Zoe, my maid alter ego. I found myself naturally keeping the house tidy throughout the week even in my normal male state. Cleaning was becoming second nature even though part of me thought that if I left the house messy enough my wife might demand an extra visit from Zoe.
Perhaps it was because my wife had been keeping me locked in my chastity cage for longer and longer and I had a lot of pent up sexual energy. I felt like I was able to release some of this energy into my dressing up as Zoe, even though it did feel like a long teasing session, especially when my wife rewarded Zoe by making out and caressing her body. My wife had also started demanding that I wear panties every day to be more in touch with Zoe so feeling my thongs holding down my caged penis and tickling my butthole made me constantly think about dressing up as a maid.
One day I finally built up the courage to talk to my wife and suggest that Zoe spends an extra day each week cleaning. I gave examples of all the chores that she could perform in that time such as mopping the house, reorganizing the pantries, cleaning all the house windows, etc and promised more Zoe would make her happy.
“Just can’t get enough of being my sissy maid, can you? Wow, Brad. I knew you would like it, but not this much,” she replied to my suggestion. “Alright, Zoe can come more often but only if you agree to a few caveats.”
I blushed a little at her calling out my enjoyment of being Zoe. “Alright, name it,” I tried to say as nonchalantly as I could.
“First, I want to hear you admit it. Say this, ‘I love being your sissy maid and doing everything my Mistress says’.”
Pretty easy first demand. I repeated her line as a smirk grew on her face.
“Good. Next, you have to agree to me expanding the toys I use with Zoe. If Zoe is going to be cleaning more often, then I’m going to hold her to a higher standard and may need new options to motivate her for her new role.” She crossed her arms and lifted an eyebrow as she listed her first requirement. Clearly she has been thinking about this herself.
“Ok, sure.” I wasn’t sure what toys she meant but it couldn’t be too bad – maybe a bigger butt plug or spanking with a bigger paddle? “What else?” I asked.
“Lastly, I like that you mentioned cleaning all the windows because they definitely need to be cleaned. However, once you get started I think you’ll notice that most of the dirt is on the outside of the windows. Zoe will be expected to clean the outside as well.”
My heart skip a beat. Outside? She wants me to clean outside?
She could tell I was panicking. “Or maybe you’re just not cut out for this whole maid thing and we should just stop. If you can’t clean some simple windows then you’re not of much use to me.”
Here I was asking to be her maid more often and she was suddenly threatening to take it away. I had no choice. She knows she has all the power and she’s choosing to humiliate me with it.
“Ok, fine. You know Zoe is a good girl and will do anything you say so of course she will clean the windows inside… and out.” I didn’t feel good about agreeing, but I couldn’t lose being Zoe.
“Exactly what I wanted to hear. Now I expect to see Zoe here in 15 minutes.” She shooed me away with her hands and I excitedly ran off to become Zoe. “And remember,” she shouted after me. “This was your idea, my little sissy.”
The way she said that unnerved me, but I didn’t care. I would get to be Zoe more often.
Becoming a Sissy Maid: Unlocking Hidden Desires is now available on Kindle and Paperback. Read the full story of Brad, Zoe and Melissa in this 13 chapter, 136 page book.
Hello Madame,
Yes I am a sissy crossdresser with a ardent love and desire to dress up in ultra pink nylon lingerie.
My dream came true in New York many years ago were i finally found a smal lingerie shop that were
friendly and helpfull in permitting me to purchase all my dreams directly in the store. Yes it was difficult
to find a place were i would feel free to purchase all my dream garments. It was very difficult to find a
place that was open minded and helpful to a sissy like me. At first I was very nervous and up tight
but desire to own pretty panties,bras, garter belts,corsets and night gowns was so strong that I overcame
my shyness. Hope this is not boring you, would love to continue in detail my true story. Shall i continue????
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