BDSM Stories: The Crossdressing & Chastity Device Initiation

I arrive at the mansion nervous and anxious as to what may transpire. Three knocks on the heavy wooden door with my head bowed down as Mistress Danielle Blunt instructed. The door creaks open as a long, knee-high, stiletto-heeled black leather boot enters my vision.

My breath quickens as a perfectly manicured hand reaches under my throat and pulls my gaze up toward my Mistress, her red nails gently touching my face. I’m entranced by her eyes, looking down on me like the worthless boy I am. Mistress gestures for me to come inside.

I stand in the middle of the room and am told to strip while Mistress takes a seat on a heavy leather chair. I take off my clothes, revealing my slender, hairless frame with my soft hair falling to just above my shoulders. Mistress points her finger at me, gestures for me to come over to her. I oblige, crawling on all fours to the side of her chair.

Mistress places two soft leather gloves over her hands and places a pink chastity device on my small, flaccid penis. As the lock inscribed with M.B. clicks shut, she smiles looking deep into my eyes.

I’m bent over her knee, ten spanks on each butt cheek for her amusement. I feel a wet, soft finger enter my anus as Mistress opens me up to place a butt plug inside me. I sigh at the feeling of being filled, my prostate longing for the sense of being pressed again. The butt plug is attached to a thin black leather harness, which is locked onto my body.

I’m transferred over to a chair in front of a pink dresser. I sit and a wave of pleasure from the butt plug enters my body. Mistress stands behind me, pulling my head up and looking at me straight in the mirror. She caresses my facial features, commenting on how feminine my physique is and then commences applying light makeup.

Beginning with the foundation, followed by a heavy, dark eyeliner, false eyelashes, and bright pink lipstick… I’m being moulded and transformed in front of my very eyes.

Onto the crossdressing, Mistress places some pink latex panties on me, crotchless with a little hole at the front for my chastity device to poke through. I’m leaking pre-cum, so Mistress grabs some tissues and gently wipes off the pre-cum. With the same tissues, she has me blow my nose… small bits of pre-cum doting my newly manicured face.

I’m then placed into some black leather flared pants that go down well beyond my feet, along with a white silk shirt. Mistress places a pair of leather ankle boots with a 3-inch stiletto heel onto the floor, which I easily slide into.

I’m transformed into her new little sissy secretary. She’s holding me in limbo, playing with my gender fluidity, molding me into a very masculine look for a woman.

I enter her office, my heels clicking on the wooden floorboards. Mistress sits in her office chair, her curly black hair tied back neatly in a ponytail, her red lips poised as she taps her black stiletto boots on the floor. Her black leather pant suit rubs gently on the office chair.

I’m beckoned over and Mistress unzips my pants, exposing my chastity device. I’m leaking again, so she grabs some tissues and cleans up my pre-cum. She then hands me the tissues and instructs me to use them throughout the day to keep my lipstick in check.

Mistress then pushes her chair away from her desk and undoes her pants, exposing her beautiful bush and vagina. I’m beckoned down to begin using my tongue to provide oral pleasure to my Mistress as she continues to work. I swirl my tongue around her beautiful, sweet pussy as she lets out small moans of pleasure while gripping the back of my head with her hand.

Once finished, Mistress instructs me to use the tissues to wipe my face of her cum and scent. I’m leaking again, but this time Mistress grabs a disposable mask and wipes all the pre-cum on the inside of the mask. I’m beckoned out of the office and back into the public, putting on my mask and catching the train home… the scent in my mask a constant reminder of my session with Mistress Blunt.