Short and erotic story how feminization began for one lucky man-sissy
When Henry Fitzwinkle married Sally Blunt he knew she was a strong woman. She already had her
law degree, and she carried herself like the aggressive three-sport star she had been in high school.
In college she had been an all-star volleyball player, and with her blonde hair and muscular body she
looked like a Nordic goddess.
Henry was a small man, and when he saw this goddess walking down the aisle toward him in her
wedding dress, her cleavage spilling out, he actually felt a tingle of fear. She looked so big and
buxom, and he wondered if he’d be able to satisfy her.
Their wedding night he found out he couldn’t. She was insatiable, and she attacked him like a wild
animal. He did the best he could, but after a few hours he felt like a deflated balloon, and he couldn’t
get his poor exhausted dick to stand up at all.
“We’ll have to do something about that,” Sally said. “I could go for another five hours, sweety, so
you’ll have to be a good little hubby and cooperate.”
Henry assured her it was just a temporary problem, but it wasn’t. Every night of their honeymoon
Sally wanted more sex, and she quickly wore him out. She tried all her feminine wiles, but Henry
couldn’t get it up, and she got to the point that she was angry with him.
“What kind of a man are you?” she said. “I’ve kept my body toned and tight, I work out every day, I
wear the sexiest clothes, and you can’t get it up? I hope you’re not a pansy like my father.” Sally’s
father was president of a line of women’s clothing stores, and he was a well-known crossdresser who
had been feminized by his wife, Sally’s formidable mother. He wore panties and lacy dresses at
home, and was completely under the thumb of Edwina, Sally’s mother. “My mother hasn’t had sex
with him in years,” Sally said. “She told me he’s nothing but a panty-wearing sissy nowadays.”
Henry assured her he would not turn out like her father. He embarked on a program of weight
training, vitamin supplements, and even Viagra, but after a few months of this he still couldn’t keep up
with Sally. Her sexual appetite was voracious. He was walking around like a zombie in the daytime,
exhausted all the time with Sally’s demands. Sally started showing her impatience with him in public,
making remarks about him being a “pansy” and not man enough for her.
They went through a period in which Sally threw herself into her work, taking out her sexual
frustration in the courtroom, and it paid off, careerwise. She won some big cases, and was on track to
be named partner in her law firm in record time.
Lawyers can’t ever be satisfied for long, though, and Sally found that she had a need to dominate
Henry, since he couldn’t dominate her. Their marriage turned into a war, with Sally seeking to control
Henry in everything, and he resisting her.
Then one day Sally poured out her frustration to her mother. At lunch in a swanky restaurant, she told
her mother of Henry’s sexual failings, his meek personality, and her frustration with him.
“Oh, he’s just like your father,” Edwina said. “He’s a closet pansy. He probably wishes he could wear
your panties. Have you found him rooting around in your lingerie drawer?”
“Well,” Sally said. “I haven’t caught him doing it, but there are times when I’ve suspected it. He’s been
red-faced a few times when I’ve come in the bedroom after he’s been there for awhile.”
“I knew it,” Edwina said. “A panty wearing man is the first step to a pansy man. He just needs a little
push, dear. You leave it to me … I’ll have him turned into a frilly pansy before you know it.”
“But why would I want that?” Sally said. “I want a man who can satisfy me.”
“Well, it’s a lot of fun to dominate a man,” Edwina said. “It’s fun to make them into little lap dogs who
will do whatever you ask. After all, you don’t want him objecting when you spend all his money, do
you? And a fully-trained pansy husband is a great help around the house, doing chores and so forth.
Plus, they won’t object, poor little dears, when you find a real man to satisfy you. They’ll be happy just
to stand by and serve you when you’re finished.”
Sally had to admit that sounded like fun, so she agreed to her mother’s plan.
The next weekend Sally took Henry to lunch at her mother’s mansion. They were alone, because
Sally’s father was at his clothing store, and the maid had the day off. They had a lunch with plenty of
wine, and they all had a great time laughing and giggling. After lunch was cleared away, Edwina said,
“Henry, I want to take Sally clothes shopping. We’ll be gone a few hours. You just stay here and
make yourself comfortable.”
“Sure,” Henry said.
“Oh, by the way,” Edwina said. “There’s something you could fix for me. My husband is not the
handyman type, but I bet you are. My lingerie drawer is stuck shut, and it’s driving me crazy. Do you
think you could fix it? I know a big, strong man like you could do it.”
“Uh, okay,” Henry said. “Sure. I’ll do it.”
The trap was set.
Edwina and Sally went out, and Henry went upstairs to Edwina’s bedroom. He quickly found her
lingerie drawer, and jiggled it awhile till he got it to open. Inside was a treasure trove of frilly
underthings, in a rainbow of colors. He was feeling tipsy and uninhibited, so he picked up a pair of
lacy pink panties with cute little white bows on the rear. They looked so soft and delightful that he
couldn’t resist trying them on. In a moment he had taken off his pants and underwear, and pulled on
the lacy panties.
They fit him like a glove, and his dick stiffened immediately. A rush of blood went to his head, and he
thought he was going to pass out in ecstasy. Before long he was prancing around looking at himself
in the full-length mirror in Edwina’s bedroom. He felt so free and feminine, and he struck poses like a
pinup girl, pouting his lips and sticking his ass up in the air.
His dick was throbbing by this point, pushing against the smooth fabric of the panties, stretching the
fabric tight. He began to play with himself, caressing his stiff rod through the panties ever so softly,
letting the womanly feelings flood through his body, which turned him on even more. Before long he
was stroking his hard cock through the teeny tiny little panties, making flirty faces at himself in the
mirror, feeling his body flush with excitement, building to a peak.
And what a peak it was. He stroked faster and faster, squeezing his cheeks together in the panties
and reveling in the delicious feel of the soft, silky fabric on his hard cock, and moaning with pleasure.
By now he was pumping harder, and the red tip of his stiff cock had peeked out of the elastic band at
the top of the panties, and he grabbed it and stroked harder and then —
he exploded in a gusher of hot cum, spraying it all over the front of the panties, and even showering
drops of it on the rug. He quivered and shook as the massive orgasm worked through his body, and
he screamed like a girl.
“Oh my God,” he said, in a high, girly voice. “I never had an orgasm like that before! That was
And that’s when he heard a noise behind him. He turned to see Edwina and Sally giggling and
pointing at him.
“My God, he looks like such a pansy,” Sally said, roaring with laughter.
“Oh, dear, don’t be harsh,” Edwina said, giggling. “I think he’s very cute. He has a cute little ass,
Henry was red-faced with shame, made worse by the sticky gobs of cum all over the panties, in full
view of Edwina and Sally.
“Look at all that cum, mother,” Sally said. “It’s obvious he likes wearing those panties.”
“Oh, yes, I can see that,” Edwina said. “Our little Henry likes to look like a girl.”
“I can explain,” Henry said.
“No you can’t,” Edwina said. “There’s no explanation for this except that you’re a girly man. You like
wearing those panties, don’t you? Well, I say we go all the way and make you a frilly sissy, because
that’s what you really are.”
“Now listen,” Henry said. “You have it all wrong.”
“No we don’t,” Sally said. “I married a sissy, it’s obvious to me now. Well, the only thing to do is to
complete your transformation, Henrietta.”
Henry knew he was whipped. He couldn’t explain away what he’d done, and the sight of those two
formidable women laughing at him had him shaking with fear. He knew that if he didn’t do what they
said, they’d make his life miserable. He simply stood there, tears rolling down his cheeks.
“Aw, look at him,” Sally said. “He’s crying, poor dear.”
“Well, he’ll feel better after we put some makeup and clothes on him,” Edwina said. “You know, he
looks exactly the same size as my husband. I’ve got a whole closet of girly clothes we could try on
And they set to work. By the time that afternoon was finished, Henrietta had been transformed into a
mincing, petticoated sissy who obeyed his two mistresses like a lap dog.
And he was never happier.