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Sissy Stories

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Chrissie Chapter 4

Chrissie makes a deeper committment

My masters had wanted me to get an early start Saturday morning, so by 9:30am I was already in my maid’s uniform scrubbing the hallway baseboards while Rebecca and Karl relaxed in bed smoking a wake-up joint and watching cartoons. From my kneeling positio...

Neighbours - Chapter 56

Thanks to Liam, Crissy and Mallory get closer

I was barely recovering from our shared experience and was now eagerly searching Mallory’s face for clues about his decision. There seemed to be real torment at play. “I… I want to stay. I will just have to make a call…” he finally announced. “Oh, is some...

Becoming Anne - My Feminization Chapter 1

My wife discovers my need to be feminized and begins my makeover to Anne (series)

I walked into our bedroom. Jess, my wife sitting on the bed. Beside her were some of her sexy lacy underthings, items I had been wearing in secrecy. “Please don’t lie to me,” she said. “You have been dressing like a girl, using my clothes, haven’t you?” M...

Adventures in House Sitting — Part 1

A crossdressing sissy takes a two-week house-sitting opportunity to expand her horizons.

It was too good to be true. My daughter, who lived about three hours away, needed someone to house-sit for her for a couple of weeks. I was quasi-retired and able to do what work I did from “home” (read: anywhere I could get an internet connection). My wi...

Adventures With Eddy - Part 3

Eddy dresses me up, ties me down and turns me into a whore

As I woke up the next morning, the events of the past two days started to rush through my thoughts. I couldn’t believe all of the changes that had happened to me while being with my neighbor, Eddy. I was sixteen, and Eddy and I were tasked with spending o...

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