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Feminizing Henry Part III

Henry's feminization enters another stage -- he kisses a man.
Several months passed. Henrietta was in a state of constant turmoil, switching between male and female identities many times during the day. He wanted to think of himself as a man, but it was so hard when Sally and Edwina kept mocking his masculinity and treating him like a silly sissy girl.

One day Henrietta awoke from dreams of frilly panties, pink cotton candy frocks, teddy bears, shiny stockings and kicky red high heels to find himself with a head buzzing with hypno-thoughts of bimbohood. The subliminal hypnosis tapes that his mother-in-law Edwina had made him listen to were slowly turning him into an empty-headed sissy who wanted nothing more than to dress in frilly things and serve a strong woman.

"Okay, sissy boy," Edwina said, opening the door to Henrietta’s boudoir. Edwina was especially imposing this morning: her voice was booming, and her huge breasts were spilling out of her tight, low-cut dress. She stood over Henrietta’s bed and said, "Time for your girly hormone injection."

Edwina rolled Henrietta over on his back and pulled his pink panties down, then stuck a needle in his jiggly sissy rump.

"Good!", she said, slapping Henrietta on his ass. "Another step on the girly road for you, sissy boy. Now, let's see how femmie you look today." She pulled him out of bed and marched him over to the dressing mirror, then took his nightie off and examined his budding breasts.

"My, my, honey," she said. "You've got more than a mouthful now, don't you?"

Henrietta blushed to see his cute little round breasts perking up like a teenage girl's. "Why, yes," he said. "They seem to be growing."

"And look at your ass," Edwina said. "We're going to have to buy you a bigger size in undies, dear, because your cheeks are bulging out of your panties. That ass of yours has definitely gotten bigger, hasn't it?"

"Yes," Henrietta said. "I think it has." Then, caught in one of the mood swings he had been having of late, he got teary-eyed. His lower lip quivered and he said, "W-what have you done! I used to be a man, and now ... now look what you've done!" He collapsed in tears on the bed, kicking his feet and pounding his fists on the pillow, sobbing in the high-pitched voice he had developed lately.

Edwina could barely contain her laughter. "Now, now," she said, patting Henrietta's bottom. "I know it's upsetting, but you can't fight it, honey. You were always a bit of a feminine man, and Sally and I have just brought that out all the way. You'll never be able to satisfy a woman again, so you should just give up and give in to us. You'll enjoy life more as a sissy anyway."

Just then Sally walked in. She was wearing her usual work outfit -- a skintight suit that showed every bit of her curvy figure, with a jacket that buttoned tight around her waist and showed plenty of cleavage, along with high heels that emphasized the insolent sway of her hips when she walked. She curled her lip when she saw Henrietta on the bed.

"What is that pansy doing on the bed, when he should be dressed in his maid's uniform and doing his duties?" she said. She picked up one of Henrietta's fashion magazines and gave him three quick, hard whacks on his exposed ass with it, raising red welts on his pretty white-pantied ass.

"Get to work," Sally said. "Start cleaning this place. I'm having a friend over for dinner tonight and you'd better be ready to serve us! When I get back from work this place had better be looking good, or you're in for some punishment, sissy!'

She walked out of the room, her big round buttocks straining against the fabric of her skirt, and Henrietta remembered when that sight used to arouse him. He looked down at his shrunken, limp sissyclit and realized he felt nothing, and tears came to his eyes again as he had to admit Edwina was right and he'd never be able to satisfy a woman again.

"Now, now, dear," Edwina said. "Don't get emotional again, sweety. You have too much work to do. You heard Sally, she's having a friend to dinner and she needs you to get this place looking perfect, and she needs you looking good, too. I'm sure we can find some nice ruffled panties and a clean maid's uniform for you to wear."

The thought of wearing a cute outfit made Henrietta smile, and he got straight off the bed and let Edwina dress him in a fresh pair of ruffled white panties, sheer white stockings, a stiff white petticoat, and a black maid's uniform. Edwina brushed his long blonde hair and tied it up in pigtails, and helped him put on his platform heels.

Henrietta spent the day cleaning the house from top to bottom. He dusted, washed, scrubbed, polished, and buffed everything, wearing his headphones and listening to his feminization hypno tapes. He minced about on his heels, feeling so girly and feminine that he could just burst sometimes, he really could.

When Sally came home she rolled her eyes and said, "My, what a complete sissy you are!" and she made Henrietta wait on her as she dressed, helping her to put on her panties and a sexy spangled gold dress, and even making Henrietta put her makeup on.

"This is a special guest," Sally said. "I want everything to be just right. I'm thinking he'll want to fuck me by the end of the night, and I don't want any screwups from you, pansy."

"Yes, mistress," Henrietta said.

Later, Edwina was in the kitchen making the dinner, Sally was sipping a glass of wine on the couch, and Henrietta was lighting the candles at the dinner table to add just the right romantic effect, when the doorbell rang.

Henrietta minced over to the door, his skirt flouncing with every step, and he opened the door and got the shock of his life. Standing there was his boss, the man who had fired him months earlier when the firm was cutting back. Joe Dugan was a broad-shouldered, muscular man with a square jaw and a permanent five o'clock shadow. He was a man's man, and the look on his face when he saw Henrietta was one of shock and scorn.

"Henry Fitzwinkle?" he said. "Is that you?"

"Uh, um, yes," Henrietta said, blushing deeply. "I, uh, well, it's a long story."

"I'm sure it is," Joe said, brushing by Henrietta on his way in the door. "I'm sure it is."

"Henrietta," Sally said, coming up to them. "You're not showing good training. Take Mr. Dugan's coat, please."

Henrietta blushed again, but he dutifully helped Joe to take his overcoat off. He noticed Joe's strong shoulder muscles rippling under his jacket, and he was shocked to feel something unfamiliar in his panties. It was -- OMG -- a bulge.

He turned away, hoping no one would notice his embarrassment, but it was too late -- Edwina had caught on.

“My, my,” she said, coming over to Henrietta, and lifting his skirt. “What have we here? I think our little sissy is excited about seeing Mr. Dugan.”

And there, to Henrietta’s eternal humiliation, was his teensy little penis standing straight up, its red helmet peeking over the top of his white ruffled panties.

He blushed in shame as Sally, Edwina, and Joe all laughed.

“I never knew he liked guys,” Joe said.

“I always knew he did,” Sally said. “He can’t satisfy a woman, because he’s a lot more interested in guys.”

“Really?” Joe said. “Well, let’s see about that.”

He strode over to Henrietta and grabbed him roughly by the shoulders, pulling him into a tight embrace. Before Henrietta knew what to do, Joe was kissing him! Henrietta tried to push against Joe to get away, but Joe was too strong. His mouth was greedy and insistent, and his tongue probed roughly inside Henrietta’s mouth. Henrietta felt a flush of heat all through his body, and the excitement was like an electric current running through him. He felt like a weak little girl in Joe’s strong grip, and although he had squirmed and tried to push away at first, all of a sudden he gave in and let Joe kiss him. His penis leaped in his panties, and as Joe’s hands moved around and cupped his ass, he moaned in pleasure. Joe moved one hand around to the front of Henrietta’s panties, and the sissy quivered involuntarily, shuddering with joy.

And then it stopped.

Joe broke off the kiss, pulled back with a smile on his face, and said, “Well, well, Sally, I think you’re right. Our little sissy boy has a thing for guys. Just look at how hard his little weeny is now.”

It was all too much. As Henrietta blushed crimson in shame, with the laughter of Joe and the women ringing in his ears, his sexual trigger was pulled and he had an orgasm, right in front of them all. He shuddered and spurted sissy cream all over his panties, and he let out an involuntary squeal of pleasure.

Now he knew he was truly a sissy.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Story copyright 2015 Janno Jones. All rights reserved.

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