In sophomore year there was a new girl in school. There was nothing special about Mary. Well, that was what everyone else but me thought. I always felt she was special. Ok, so she was not beautiful. Cute perhaps in the girl-next-door way. Not one of the popular girls. While smart far from the top ten students in our class. Not an athlete. Actually, she was prone to various illnesses so she didn’t take PE and was she was away from school for a long time in after Christmas. Not a recluse either . Just one of the girls. But for some reason she was the girl of my dreams.

The laptop screen casts a blue pall over Caden's hands as he scrolls through endless grids of sports bras — women in mid-stride, frozen in athletic poses, all of them grinning with their hands on their hips like this is some kind of victory. His fingers hesitate over the trackpad. None of these are designed for someone who still lifts weights but needs to strap down what shouldn't be there in the first place.

“You gonna be much longer in there?” my flatmate asks as I apply the finishing touches to my make-up and give my ever-growing hair one final brush.

“Just a sec,” I reply. “Just got one last thing to do….” I smile as I reach into my medicine drawer and retrieve the two packets of pills that over the last two weeks have become beyond precious to me. The fact that one packet is labelled ‘progesterone’ and the other ‘oestrogen’ should be all you need to know why.

This is a story about a trans woman taking her first steps into the big bad world. ( not my usual sex stuff )

I looked out of the window of my small bedsit one last time as I steeled myself to face the world. I held my breath and nearly scrambled out of my front door and the main door. I forced myself not to run up the path. I had been watching to make sure my neighbours were not approaching or leaving. A few steps and I was on the street.

A week later. The alarm blares and Caden slams a palm down on it, the sharp sting of impact radiating up his wrist. He stares at the ceiling. Podcast day — out of town, he and Hale are both guests on the show. Keynote finalized. Twenty-eight days since the first flannel seam had scraped his neck raw.

Ambush, Myrtle Beach, South Carolina:
Daisy dances around on stage while Jessie plays the drums. The band decided to try something new tonight by letting Daisy be the frontwoman, since they were playing at one of the local gay clubs near the beach.

Caden wakes with his arms folded across his chest, fingers digging into his own ribs. A dull ache pulses beneath the skin — persistent, like the ghost of a bruise. He rolls onto his back and hisses as the sheets drag across his nipples, rough against skin that had turned traitor overnight. The pain isn't localized; it radiates outward in concentric circles, tightening with each breath. He presses the heel of his hand against his sternum, testing. The pressure sends a jolt down to his navel.

Cover art by Erin Halfelven
©2026, SammyC

The dial tone buzzes in his ear like a trapped wasp. Caden taps his fingers against the desk — once, twice — before the receptionist finally picks up. "First available is Thursday at two," she says, the words clipped. He books it without asking questions. The phone clicks back into its cradle with a finality that feels heavier than it should have. Petra's number glows on the screen beneath it, untouched. Data first. Then emotions.

Cover art by Erin Halfelven
©2026, SammyC

This is the start of a (currently) 3 part story, dealing with the world’s biggest sissy, the world’s biggest she stud, the greatest hookup ever written and (eventually) all that follows! If you want to read the rest of the night and stay informed of all the nights beyond, subscribe to my patreon:

https://www.patreon.com/c/SissyGirlSammi

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“Aww, poor you,” Sonia teases, making me roll my eyes as I fasten my tie. “Your summer of fun was always going to come to an end sooner or later, you knew that.”

“Yeah, ‘fun,’ ” I reply with a snort of laughter, though what I of course don’t want my sister to know is that this has already been one of the best summers of my life.

Rainbow Cactus Company, Virginia Beach, VA, USA
Jessie belts out some of their new songs as Daisy kept the beat going and have it flow right into the next song in their lineup. Two figures sit in the back of the club listening to the band play and watching as each member danced and play solo parts during the songs. The manager of the club, stood nearby with a few drag queens working that night.