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Sissy Stories

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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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Public Access — Part 7

What could a “girl’s weekend” hold for Stacey with Katie leading the way?

I appraised my disheveled appearance in the bathroom mirror. My skirt and cheer top were a cum-stained mess and the cum all over my face and neck had dried to a crusty layer. I had no idea how to care for the wig on my head that was also matted with cum,...

As we left Adam and Michael’s apartment, Morgan ordered an Uber. We didn’t speak a word to each other the entire way home. The night’s events swirled in my mind and I was having trouble even forming the right words, the right questions. I’m sure Morgan wa...

Public Access — Part 6

Stacey has graduated to the Ladies’ room. Will all of her dildo training and butt plugs prepare her for what comes next?

I left an absolute wreck. I only pulled on enough clothing so as not to arouse any suspicion should I encounter anyone on the way out of the building. At home I took a quick shower, releasing myself from my cage to properly clean up. After that first siss...

Neighbours - Chapter 35

Crissy starts to become famous

I woke with a smile, though the details of whatever dream I’d been having eluded me. Perhaps I was imagining things but as I looked over at Cheryl, just starting to stir, it felt like I could still taste her pussy on my lips. Cheryl seemed to wake with wa...

Neighbours - Chapter 33

Chris is still reeling from the day's events, but more is always coming

My sleep was unsettled and uneven and my mind was too full of what had happened to rest. When I finally gave up on attempting to sleep, I realised I was almost afraid to leave the room. I didn’t feel prepared for what awaited me out there. The house was s...