My Pretty Sissy Boy – Part 1

The sissy training of my panty thief continues . . .

The atmosphere had been a little strange at home since I had caught my stepbrother, Alexander – now named Alexis – wearing my panties. I only had to look at him at the breakfast table to make him blush scarlet and, as I held his gaze, I could visualise that beautiful, thick cock hardening in the silky panties I had instructed him to wear.

Much as I loved tormenting him, I was pleased with my sissy creation. After he had fled from my room when I caught him that first time, he had returned my purple panties and bra to me the next evening, beautifully laundered and with a brand new pair of sheer, black stockings to replace the ones he’d worn. He had also given me the most beautiful and enormous bunch of flowers with a handwritten note saying, “Thank you for making my wildest dreams come true!”

The subtext of this, of course, was “Please don’t tell anyone!” I was still touched, however, and so I had purchased a couple of pairs of silky-soft, pink satin panties for him online at Victoria’s Secret. I left them on his bed with a note of my own saying, “You are to wear these panties under your clothes at all times. Never take them off. I will be checking.”

Alexis had passed all my sudden spot checks.

I slid my fingertips down the back of his tight pants to make sure I could feel that telltale silk. I even walked into the bathroom while he was showering, not to look at him particularly, but simply to check that my good boy had been wearing them and only took them off so he could wash. I did not speak to him during these cursory inspections. It was my perfect right to check on my sissy as I saw fit. He tried to keep his eyes modestly cast down and I tried not to catch his gaze, but occasionally we would glance at each other and burst briefly into grins of excitement.

Alexis was not aware of this, but I was secretly planning to take him to the next level. I wanted to parade my sissy in public. Full make-up and female clothes. Perhaps introduce him to some special friends . . . I was just waiting until we could be alone so that I could prepare him properly.

One afternoon, we came home to find a note from our parents.

“Gone away for a couple of nights. Look after each other.” Since his father had married my mother, this was fairly typical. Passionately wrapped up in each other, they had no idea about the simmering tension which was building between me and Alexis.

“Right, darling – get your ass upstairs, I’m going to get you dressed. We’re going out!”

“Seriously?! said Alexis, “What – you mean in your clothes?” “Yes, darling, I do.” “But first we need to shave you.”

We ran up the stairs together to the bathroom. I watched carefully as my blossoming sissy shaved that darkening stubble as closely from his face as he possibly could. Then I applied a thick layer of moisturiser to his eager face to soften his skin and, hooking my fingers into the front of his pants, I led him to my bedroom.

“Take off all your clothes except your panties. No boy clothes allowed now.” Obediently, Alexis stripped.

I looked approvingly at his silky, hot pink satin panties.

I ignored his hardening dick. There would be plenty of time for that later. I had some very specific plans.

I sat him down at my dressing table and tied up his shoulder-length hair. “OK, beautiful, I’m going to make up your face. I’m going to make you look like a real girl.” Nervously, Alexis glanced down at the vast array of palettes and pots of colour which I had laid out with all my brushes. But I knew he was excited. So was I. My sissy would be a work of art.

I worked quickly and with concentration as I smoothed primer, then foundation, into his skin – using different shades to contour his face by creating shadows and highlights which emphasised his bone structure. Why was I taking such care to create a beautiful dollface which would only be ruined later? All I can say is I got a kick out of it.

I lined his big, green eyes with black eyeliner and then got to work with my eyeshadow palette – blending shades of deep chocolate and charcoal to create a sultry, smoky eye. Then I added a set of feathery false lashes to his upper lids, followed by layer after layer of mascara.

He sat obediently and with total trust as I lined his full lips with a deep pink lip pencil and then filled them in with hot pink lipstick. I blended carefully. Then I took my large powder brush and swept on plenty of shimmering peach-pink blush by Nars in a gorgeous shade called “Orgasm”. I knew this would be prophetic.

Finally, I added lashings of lipgloss.

“Look in the mirror, gorgeous – you’re done!” Alexis gazed at himself in wonderment. Facially, he was perfect. Utterly feminine. With his wide shoulders and lean, slender body, the effect was runway model.

Except for one thing . . . his body hair. It wasn’t too bad – his hair was dark and it was reasonably fine but still . . . it was hair. Body hair. Boy hair. Masculine. It had to go.


I hope you enjoyed Part 1.

Here’s Part 2.

If you would love to hear me read the whole story, my audio is available from the Temple store.

In case you missed it, here’s my first story about my pretty sissy boy:

Georgina Catches A Panty Thief

Love, Georgina


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