Dave's word was good. I spent the weekend watching TV. Football and old movies. All I normally got was cooking shows and old reruns of old soaps. For a few hours, I forgot that I was sitting watching TV in a frilly red baby doll. with matching knickers.

My first client was two guys who wanted a maid. I arrived and was told to change in the bedroom by a middle aged bald guy. When I got back downstairs, I saw the other man was younger and around 6f tall.

"Get us some beers bitch" said the tall guy.

This standalone story is my submission for the literotica Halloween contest, if you enjoy it, feel free to go over there and vote!
https://www.literotica.com/s/frat-house-feminization
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Chapter 3: Living My Truth

The suggestion floated through the room like a playful breeze, a whisper of mischief carried on clouds of pillows and bursts of laughter. “Let’s venture to the garden,” someone declared, stretching languidly like a contented cat basking in the afternoon sun. “The lake is simply enchanting at this hour.”

Over the next two weeks, Jennifer found herself watching James with a new, quiet intensity. It started from a place of care, a desire to monitor him after his breakdown, to take his emotional temperature and ensure he wasn’t spiralling again. But the more she watched, the more she noticed what they had both seen in the mirror that night.

The morning light filtered through the blinds, striping the empty half of the bed beside him. James groaned, reaching a hand out to the cool sheets where Jennifer should have been. Her flight to Singapore had left yesterday afternoon, and the silence in the apartment was a low hum he couldn’t quite ignore.

A text from her, sent from some airport lounge, glowed on his phone screen: Thinking of you. Go show Dr. Mercer your excellent progress! Xo.

He smiled, a little sadly. Excellent progress. Right.

Dr. Elias Mercer’s office smelled like lavender and antiseptic, a combination that somehow made the framed diagrams of mammary glands on the wall feel less intimidating. The silver-haired endocrinologist leaned forward in his chair, steepling his fingers as he studied James and Jennifer with warm, crinkled eyes.

“Let me start by saying,” Dr. Mercer began, “in fifteen years of helping transgender women lactate, I’ve never had a cisgender man walk into my office with this level of commitment. It’s… refreshing.”

Parents-to-be, James and Jennifer give serious consideration to an unorthodox parenting arrangement

Becoming Kara

The next few days passed like the last few. He had me on my knees at his beck and call. It was usually twice a day. Always with the plug buzzing away. God, it made me horney. A few times, he played with me after or before he blew his load, but I could never be sure. I was getting frustrated.

The next day my alarm went off at 6AM. I took a long soak in the bath. I was half looking forward and half dreading today. I won't lie the thought of dressing as a traditional maid was appealing. The dress I wore before was more of a costume. The dress today was the real thing.

Dawn and Diana – Our New Life – Part 5

By Kathi Jo Daniels

Chapter Eleven: Wine Tasting

Monday, November 29, 2004

We repeated our morning ritual of enthusiastic lovemaking. After showering together, I dressed as Dan, in a long-sleeved shirt, jeans, and sneakers.

Fate had a peculiar way of playing with young Alex's life, a 15-year-old boy whose curiosity often led him to the edge of societal norms. Growing up with an older sister, Emily, had its perks. He had always felt a strange fascination with her clothes, especially her school uniform. It was a peculiar attraction that he could never quite put into words, but it was a part of him that he couldn't ignore.

One fateful evening, after his sister had left for college and his parents had gone out to dinner, he found himself alone in the house. He tiptoed into Emily's room, the scent of her lingering in the air. He reached for the hangers, his heart racing, and pulled out her skirt and blazer. He had snuck into her room countless times before to try on her clothes, but tonight was different. He had decided to take it a step further.

With trembling hands, Alex donned the uniform, feeling the fabric caress his skin as he transformed. He applied a bit of her makeup, just enough to accentuate his features, and styled his hair to mimic hers. Looking in the mirror, he saw a reflection that was both thrilling and terrifying. He had become a vision of his sister, yet not quite. It was an image of femininity that he hadn't dared to explore before.

The door slammed open, and Alex's heart stopped as his parents stormed in. Their eyes widened in horror and disbelief, and the silence was shattered by his mother's scream. His father's face was red with rage as he bellowed, "What is the meaning of this?"

Alex stuttered an apology, but the damage was done. His parents couldn't comprehend his actions, and they were ashamed. In their eyes, he had crossed a line that could never be uncrossed. Without another word, his father dragged him out of the house, throwing him onto the cold pavement with nothing but the clothes on his back.

The night was unforgiving, and Alex was lost in a world that had just turned its back on him. He wandered the streets, his mind racing with thoughts of what his future might hold. As dawn began to break, he found refuge in a deserted alley, the harsh reality of his situation setting in. He was cold, hungry, and utterly alone.

I feel my suspenders stretch as I reach up to dust the top shelf in the library. The stool wobbles slightly and I am afraid I may fall. I can feel “Sir’s” eyes on me as I work. I am so self-conscious that he may see my knickers as I work.

My wife, Sharon, had just brought up an idea for how we can spice things up in the bedroom. She was talking about chastity play, where my dick is locked up and she is the keyholder. Now, I was a little skeptical of this at first; I mean, wouldn’t this technically be less sex for us? But she argued that it would build up horniness for me, leading to more passionate sex whenever I’m unlocked. So I agreed to trying it out, and she was ecstatic.

This story arose from a dream, it has no ending

The sound of shattering glass echoed through the alley, freezing the boy in his tracks. His heart hammered against his ribs as he pressed himself against the cold brick wall, barely daring to breathe. He shouldn’t have followed the man in the black coat. He should have stayed home, right where his mother had told him to. But curiosity had always been his weakness. And now, he’d seen something he couldn’t unsee.

Dawn Visits Kansas- Part 4

By Kathi Jo Daniels

Chapter Fifteen: Thursday
Thursday, October 07, 2004

Once again, I woke at sunrise with nothing to do. We got up, made the bed, undressed, and showered together. Some parts of our bodies were squeaky clean. Since we had no plans to see anyone else for the day, we did minimal makeup. I chose a blue and white golf outfit from Brenda’s Dress Shop. Diana selected a sleeveless floral dress.

Precious Time - Part 3

A Step Too Far?

by Suzie Dalkin

This was written without any idea where it was going. As a result, readers may find it funny or offensive – or neither – or both.

Edward Arley was a very organised young man. His parents were staid pillars of the community who for many years had run a successful estate agency business in Sutton Deering, an old market town about 50 miles north of London.

In a world much like our own, aside from the fact that werewomen walk amongst us, the squares struggle to uphold their binary social order. Their instrument of tyranny is the Office of Werewoman Registration, cog in a bureaucratic machine designed to keep werewomen in their place in the social pecking order. But hey, this is a transformation story, and things can… change!

Dan Becomes Dawn – Part 2

By Kathi Jo Daniels

Chapter Eight: Time for Work
Sunday, September 12, 2004

I woke Sunday morning, got up, made the bed, showered, shaved, and put on panties and a bra. After applying makeup, I chose an elbow-sleeve A-line dress in white with blue panels and shoulders with white sandals. Then my wig and finished with small hoop earrings. I packed everything, and put my suitcases by the bedroom door.

Taking my computer to the kitchen, I said, "Good morning, Roger. How are you today?"

rld and are forced to work together to survive and find out how to escape.

The truth is revealed?

Chapter 23 recap

I glance at Lorien again, his steady breathing filling the quiet room, and I feel a pang of guilt. He deserves to know. About Shade. About everything.

First thing in the morning, I tell myself firmly. I’ll tell him everything. I’ll tell him I want to be with him… and I’ll tell him about Shade.