Cuckold and a sissy

Sissy Wendy heard the Master's car arrive. He desperately checked 
his appearance in the mirror. Yes, his long grey dress was correct, 
four inches above his plain black shoes, his full length white apron 
clean and correctly worn, straps over his shoulders, bow neatly tied 
on the waist.

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He dare not earn the displeasure of Master Edwards. The thought 
of that terrible thin, five foot cane in his massive hands, his huge 
six feet four frame raising it high over his shoulder, caused him to 

The elderly lady smiled as she saw the sissy trembling. "Answer 
the door to the Master, you useless slut." 

"Yes Madam Judy," sissy replied. "Is your maid's cap on correctly 
sissy?" He panicked and dashed to the mirror. Yes, his little white 
maid's cap was slightly askew ,he quickly perched it on her head 
making sure the ribbons at the back fell in a straight line down his 
long dark hair. "Oh is my cap on correctly Mistress Judy", she 
laughed and said "yes sissy, now answer the door, the Master will 
getting impatient." The front door bell gave a long ring, "oh no I 
must run to the door" the sissy cried. 

He dashed from the laundry room ,the long grey dress restricting 
his stride to his normal mincing steps ,Behind him he could hear 
Judy's derisive laughter at the pathetic sight he presented, a 
mincing sobbing sissy in tears for not answering the door bell 
sooner He minced sobbing to the door a pathetic feminised sissy. 

It had all started two years ago, his life of menial servitude and 
sexual frustration. 
Doctor Samantha, his beautiful wife of six months had said, 
"Darling, we have been invited for the weekend to my chairman's 
house. His name is Mr. John Edwards."

"Do we have to go, Samantha? You know I'm shy around people."

"Yes dear, I know you are shy, but you don't have a career since 
inheriting millions from your Aunt Jane, whereas I, darling, still 
have a career."
Smiling sweetly she had continued, "I'm sure you will assist little 
Samantha in her career at the medical research centre. "
Unable to refuse her he had quickly agreed, "Of course, Samantha, 
we must go."

"Thank you darling, I felt sure you would  understand."

The following weekend they drove to Master Edwards' huge 
isolated house set in a thousand acre park.  Arriving, he removed 
the luggage from the car, some what puzzled why Samantha had 
bought almost her entire wardrobe but had packed none of his 
clothes. Remarking on this to Samantha, she had replied 
laughingly, "I'm sure we will find something for you to wear 
darling, now ring the bell." Standing waiting for the door to be 
opened he was conscious of their difference in size. Samantha 
stood over six feet in her high heels, whereas he only stood five 
feet four. 

As the door opened and he saw Master Edwards for the first time 
he became even more conscious of his lack of stature. Standing 
there was a huge handsome man in his mid forties. Standing six 
feet four, Master Edwards towered over him. "Samantha darling 
how lovely to see you ," he had said in his deep masculine voice. 
Looking down with disdain at him he had said, "You, carry 
Samantha's cases in." Feeling humiliated to be 
spoken to in this manner in front of Samantha, he nevertheless 
quickly obeyed Master Edwards; such was the presence of this 
huge man he felt completely overawed. As soon as Samantha's 
luggage was in the house, Master Edwards slammed the 
door shut, and said "You, follow us to your room."

"Please, don't you mean mine and Samantha's room?" he had 

"Don't you ever contradict me!" Master Edwards thundered. 
Meekly he had followed Master Edwards and Samantha down a 
long corridor then up four flights of stairs till they reached the top 
of this large house. Opening a small door Master Edwards said, 
"Get in there Sissy!"
He heard Samantha laughing as Master Edwards addressed him as 
Sissy. He obeyed the Master and stepped into the room; only it 
wasn't a room, it was a cell. It was only eight feet by four feet, bare 
walls, a small barred window, an iron single bed, one upright chair, 
and a small wardrobe. He turned round to protest and saw 
Samantha passionately kissing Master Edwards. 

"What are you doing Samantha!?" he cried.

She released her hold of Master Edwards and said, "Meet my lover 
Sissy."  Towering over him, she said, "Thomas and I have been 
lovers for years. I only married you so Thomas and I could control 
the millions you inherited." Laughing, she added ,"And now you 
are here, you have no relations, no friends, no occupation, so no 
one will miss you Sissy."

"I wont stay here, you can't make me." He saw Master Edwards 
clench his fist then he felt a crushing blow to his stomach, and then 
another blow to his jaw. He was knocked unconscious. When he 
came round he was lying on the iron bed completely naked, with 
Master Edwards and Samantha laughing at him.

He felt he had been unconscious for some time. Samantha said. 
"Yes dear, we gave you a small injection to keep you under while 
we prepared you for your new role in life. Oh don't worry, 
remember I am a trained doctor." 
"What have done to me, Samantha?"

She laughed and said, "Look in the wardrobe mirror, Sissy." She 
opened the wardrobe and he saw his reflection in the mirror. "Oh 
no, oh please, no, what have you done to me?" All his body hair 
had been removed, and he saw he now possessed two huge tits. 
Samantha laughed, saying, "You should be grateful Sissy, those tits 
are our company's latest development, completely realistic, and 
quite impossible to remove without surgery. You have a pair of tits 
size forty four DD, and you will find them just as heavy as real tits. 
I should know my tits are thirty six DD."

Master Edwards laughed and said, "She will need a large bra."

Samantha laughed, saying, "I wouldn't like to carry those around 
every day of my life."
Master Edwards stepped forward and picked up Sissy like a toy 
doll. Placing him onto his back on the bed, he lifted his legs high in 
the air, and stretched them wide open, his tiny two inch prick fully 
exposed .Samantha looked down at him. "We wanted you fully 
awake Wendy, oh yes, that's your new name Sissy Wendy, when 
we fitted you into this," bringing her hand from around her back 
she held it up in front of him.

"No, oh no, please, don't place me in that please."

"Yes!" she said, "You are going into it now!" It was a completely 
realistic vagina. 
Legs held wide apart by Master Edwards, Sissy Wendy was 
powerless to prevent Samantha as she smoothed a solvent into his 
crotch. As she placed solvent on the vagina, she explained to him 
how the vagina operated. "You see this tube inside, that's where 
your sissy prick will be placed, allowing you to piss, siting down of 
course, but I'm afraid though your little sissy prick will be able to 
become erect, you will not be able to use it, or even cum, but of 
course it won't be missed, as no woman would entertain a sissy's 
prick. " With a malicious smile she said, "Say goodbye to your 
sissy prick, Wendy." Laughing, Samantha placed his sissy prick 
into the tube, and pressed the vagina firmly home. 

She pressed the vagina firmly onto his scrotum for two minutes. 
Sissy Wendy sobbed and pleaded, "No please, no please, don't" as 
Samantha completed his emasculation. 

Master Edwards released Sissy Wendy. "Stand up sissy and look in 
the mirror," Sissy Wendy obeyed his new Master and looked at his 
reflection in the mirror. He emitted a pitiful scream as he saw his 
huge forty four tits and vagina. He fell sobbing to his knees.

Mistress Samantha threw back her head and roared with laughter as 
the sissy crawled to her, begging her to remove his tits and vagina. 
Master Edwards kicked sissy's arse and sent him sprawling onto his 
face; this caused Samantha to laugh even louder. Samantha then sat 
down on the bed , and Master Edwards placed the chair in front of 
Samantha, who said., "Sissy, bend over that chair with your sissy 
arse in the air."

Sissy placed himself over the chair his sissy arse high in the air. 
Then he felt his Master tying his ankles to the legs of the chair. 
Samantha then took his wrists and tied them to the front of the 
chair. He was completely helpless, he screamed as saw the master 
produce a long, thin five foot cane, and cried, "No, please, no 
please, no."
"Ten strokes, sissy" roared Master Edwards. 

Sissy Wendy, tears pouring down his face, pleaded with Samantha. 
"Please don't let him cane me." Samantha with feigned sympathy 
said "I know it will hurt, Wendy, but it's for your own good. You 
have to learn obedience. Now be a brave girlie, Wendy."

"N oooooooo oh nooooooo,noooooo." His screams rang through 
the room at the first 
slice of the cane. "Nooooooo, no more, noooooooo!" Master 
Edwards continued to slash down on Sissy Wendy's raised arse. 

"Only four more Wendy, be a brave girlie," said a smiling 
Samantha. Sissy was almost unconscious; the pain was unbearable. 

Still the Master continued to raise the cane high over his massive 
muscular body, bringing it whistling down from over his shoulder 
onto the screaming sissy's naked arse. Then it was over. Ten 
strokes of the cane. Sissy Wendy was released from the chair and 
collapsed onto the floor, broken, sobbing, at his Master's feet. Then 
he heard Samantha say, "Come along Wendy into your panties."
He looked up and saw Samantha, was standing over him holding a 
pair of pink nylon panties. She said, "Aren't they pretty Sissy 
Wendy. Pretty pink nylon panties, with lovely pink frills, real sissy 
panties for a real sissy like you." She smiled down at him, then her 
manner changed. "Into them now, sissy, get your arse into these 
panties !"

Master Edwards roared, "You heard Madam, get your arse into 
those panties, or do you need more obedience training?"

"Noooooo oh nooooooo," sissy screamed as he saw the Master 
raise the cane, and he crawled to Madam Samantha, saying, "Please 
put me into my panties, Madam."

Samantha held the panties open by the elastic waist band. "Come 
along then my little sweetie, into your pretty pink panties, like a 
good sissy, you don't want your sissy bottom spanked again by 
Master Edwards."

"No Madam," sobbed Sissy Wendy and he stepped into the panties. 
Samantha pulled the panties up over his waist. "There, Wendy, you 
have your first pretty panties on," she said, "Now a new pink bra, 
pretty suspender belt and black nylon stockings, pretty waist 
petticoat with a frilly pink hem." Soon sissy was fully attired in his 
pink frilly undies. Samantha then placed a black wig on his head. 
Standing back, she burst out laughing as she looked at the 
completely feminised sissy, sobbing in front of her. "To think a few 
hours ago you were a man!" Master Edwards joined in her 
laughter. "Now put her into her uniform, Samantha."

Laughing, Samantha said, "Yes, I agree Thomas, its time to 
introduce her to her new vocation." Laughing in Sissy's face, she 
said, "I say vocation, Wendy, as it is not employment, as you won't 
be paid." Samantha, then moving to the wardrobe, took out a long 
grey plain dress and passed it to Sissy Wendy saying, "Put it on, 

As soon as Sissy put on the grey dress Samantha passed him an 
apron. It was of the type worn by scullery maids in the nineteenth 
century. It was the full length of his dress with straps over the 
shoulders, and waist straps tied in a large bow at the rear of his 
waist. she placed him into it, showing him how it was to be worn.
Then she produced a maid's cap of the same period, white with 
long ribbons tied under his chin, and further ribbons which hung 
down the back. She then fitted him into a pair of plain flat black 
shoes with ankle straps. Master Edwards and Madam Samantha 
with laughter at the pathetic humiliated sissy, dressed in the 
manner of a nineteenth century scullery maid, the lowest servant in 
a household.

The Master said, "You will be dressed in that manner every day of 
your life. You will rise at five o clock every morning to light the 
fires in every room when required, you will make breakfast and 
serve it, you will clean every room until it is spotless. You will 
spend hours in the laundry room washing clothes by hand, you will 
then hang them out to dry on the clothes line, and then you will 
iron them perfectly. You will curtsey to each person you meet." 
Glowering at the pathetic sissy he continued, "When awaiting 
orders you will stand demurely with your hands clasped in front of 
you. Your head will be bowed.".

Samantha added, "If not required, you will retire to your room at 
four o' clock, put on your night-dress, then present yourself to us 
ready for bed, whereupon you will be locked in your room and the 
light switched off. Four o clock in the afternoon is quite late 
enough for a sissy maid to be up."
She laughed! "Not quite the future you had planned Wendy, is it? 
You thought to spend a life of luxury; instead you will spend a life 
of menial servitude. "She mentally hugged herself. She had hated 
this sissy for years, she had lived with her mother in his Aunt's 
house, where her mother had served as a maid. This pathetic sissy 
and his Aunt had treated Samantha and her mother with total 
contempt. She had in spite of her poverty gained a good education, 
and received her doctorate, and joined Thomas Edwards' medical 
research company.

She had grown into a beautiful woman, inheriting her mother's 
Mediterranean looks. She 
and Thomas had become lovers, and she had lived with Thomas 
for two years. Then her mother had informed her that the sissy had 
inherited his Aunt's fortune and her mother, after years of menial 
service, had not only received nothing, but this pathetic sissy had 
dismissed her. Furious at his treatment of her mother, Samantha 
had bought her to live with her and Thomas. Samantha and her 
mother had planned their revenge on the sissy from that moment. 
The thought of him continuing to enjoy a life of luxury was more 
than either woman could stand.  It was her mother who had first 
said, "I would love to see the arrogant bastard reduced to the 
menial maid position I endured under him and his Aunt.

Samantha had seized on the idea, crying out, "Yes mother, what a 
wonderful punishment." Her mother had laughed, saying, "Yes, 
especially if we could have his money." Looking thoughtfully at 
her beautiful daughter, she said, "There is a way 
Samantha, marry the arrogant bastard."
Samantha had deliberately flirted with the sissy at a social function. 
The little sissy, flattered by the attentions of a strikingly beautiful 
woman, had played directly into her hands. Within six months they 
were married. The arrogant bastard had never recognised her as the 
gawky girl who had lived in the basement with his Aunt's maid. 

Looking at the sissy, dressed in his maid's uniform, she thought, "I 
had to suffer you lying in my bed, that tiny two inch prick in my 
fanny." But as she continued looking at him she reveled in a sense 
of pure sadistic pleasure; she and her mother would make the sissy 
suffer for the rest of his life. She was bought out of her thoughts as 
she heard Master Edwards say, "Stand in the corner, assume the 
demure position." Sissy Wendy obeyed instantly, hands clasped on 
his apron, head bowed. But he could see Master Edwards strip 
naked, revealing his huge muscular body. 

Samantha laughing, took off her dress, and stood in front of him 
dressed only in a white lacy bra, white thong nylon panties, a white 
suspender belt strained down her tanned thighs to her black nylon 
stockings. She was wearing four inch high stiletto heeled 
white shoes. With a mocking smile at Sissy Wendy, she placed her 
hand on the Master's eight prick and began to fondle it. 

He let out a groan as his huge prick became erect. It grew in her 
hand to ten inches, with a two inch knob. She said, "Look, sissy, a 
real man's prick, not a tiny two inch sissy's prick." Samantha 
laughed as Sissy Wendy sobbed in the corner, still in his pathetic 
demure position. She pushed Master Edwards onto the bed, and 
still stroking his throbbing prick, leaned over him with her back to 
the sobbing sissy. She deliberately allowed Sissy Wendy to see her 
white nylon panties stretched taut across her tanned arse, 
her suspender belt straining down her thighs, her nylon covered 
legs splayed wide apart.

She heard Sissy Wendy's sobbing increase as she deliberately 
tormented him. The thought of her pathetic humiliated husband 
looking at her beautiful body dressed only in her sexy undies, while 
she fondled a real man's huge ten inch prick, excited her so much 
she felt herself cum into her panties. 

Sissy Wendy couldn't take his eyes off Samantha's white nylon 
panties, shapely nylon stocking clad legs, accentuated by her four 
inch high heels. Then she pulled the gusset of her thong panty to 
one side, showing him her dripping wet cunt. He let out a scream 
as she mounted the Master's huge swollen prick. He lay back on the 
bed, his eyes closed, as she rode up and down his huge throbbing 
prick, faster and faster. Sissy Wendy's tiny prick erected inside his 
false vagina; pre cum dripped into his pink panties. 

As Samantha rode the Master's huge prick, her cunt dripping wet, 
she looked at Sissy Wendy sobbing, with humiliation and complete 
frustration, as his sissy prick erected inside his vagina. She threw 
back her head and laughed. The vagina, she knew, was working 
just as she had designed it to, allowing an erection, allowing his pre 
cum, but never allowing the sissy release, a life time of menial 
servitude and total frustration inside his panties. She laughed as she 
saw the sobbing sissy standing in his demure position, humiliated 
and frustrated, a completely feminised sissy. She felt the Master's 
prick erupt inside her,  jets of his hot spunk filling her cunt. She 
screamed as her cum poured over his huge prick. Sissy Wendy was 
crying uncontrollably as he heard their screams of sexual 
satisfaction, knowing sexual relief was forever denied him inside 
the vagina. 

Samantha lay on top of her lover utterly and completely satisfied; 
never had she had such an orgasm,  She looked at the sissy crying, 
humiliated at seeing his beautiful wife riding Master Edward's 
huge throbbing prick, but also his complete frustration as his tiny 
sissy prick still erect inside his vagina but unable to cum. 

Samantha laughed as she felt the Master's prick grow soft inside 
her, and lifting herself off his body, allowed the sissy to see his 
Master's now limp prick. Sitting on the side of the bed with her 
stocking clad legs wide apart, she pulled the lips of her cunt wide 
apart so the pathetic, frustrated sissy could see that her gaping wet 
cunt was filled with his Masters spunk. 

As she and the Master roared with laughter at the sobbing cuckold 
sissy, the door opened and into the room walked Samantha's 
mother. She looked at the sobbing sissy in his nineteenth century 
maid's uniform, and with a cry of sheer delight shouted "Yes!" 
Sissy Wendy looked at the sixty year old lady who stood laughing 
at him, and recognised her as his Aunt's former maid. His 
humiliation increased as she said, "Yes, you sissy, it's me, the 
servant you treated with contempt, and I'm your new Mistress.
"Curtsey, you pathetic sissy, in my presence." She slapped him 
hard across his face. "You will learn to grovel at my feet, sissy." 
Samantha and the Master laughed, as Sissy Wendy curtsied in front 
of Samantha's mother. Mistress Judy said, "Crawl over here sissy, 
and kiss my and my feet." 

The room rang with laughter as Sissy Wendy crawled over to 
Mistress Judy and kissed her high heels. Samantha and Thomas 
dressed, still laughing as the sissy continued to kiss Samantha's 
mother's feet. "Isn't it time this maid was in bed?" asked Judy.

"Yes mommy, I'm sure its well past four o clock," replied 
Samantha. Looking down at Sissy Wendy kissing her feet, Judy 
said, "Put your pink night dress on now." Sissy Wendy undressed 
and stood naked in front of them. Judy roared with laughter as she 
saw his huge dangling tits, and false vagina. Pointing at his vagina 
she asked, "Is your sissy prick hard in there, Sissy?"

He cried as he confessed, "Yes Mistress, I can't cum, oooooo 
pleeeeese help me Mistress, make Samantha take it off 

Judy placed her hand on his vagina, and asked, "You mean take 
this off, sissy?" She could feel his pre cum leaking into her hand. 
Turning to Samantha she said, "In the future this girl needs to wear 
a panty liner" 

Samantha, placing her hand on Sissy Wendy's vagina. laughed as 
she felt his pre cum. "Yes, I agree mommy. Tomorrow sissy, we 
will issue you with a packet of panty 
liners; can't have you walking round in constant wet panties."

Judy threw his pink nylon night-dress at him. "Get ready for bed, 
Sissy, it's five o clock, long past your bed time. Sissy put on his 
pink nylon night-dress. "Now get into bed where you belong,"  said 
Judy. Then she picked up the long thin cane, and said, "Lift up 
your night-dress, I have waited years to do this, bend over." Sissy 
lifted up his night dress, revealing his caned striped arse. He 
screamed as Judy bought the cane down onto his arse. "Yes, oh this 
feels wonderful," she screamed, as she bought the cane lashing 
down time after time onto Sissy's arse, she was creaming into her 

Finally she stopped. Years of being treated with contempt by this 
screaming sissy had gone into every lash of the cane. As she smiled 
with satisfaction, panties soaked with her orgasm. she said, "Now 
get to bed you sissy bastard, you have got years of this ahead.". 

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