Cross Dressing
June 2023
This week during a rare visit to London, I visited Mistress Cara for the first time. I had been admiring her website and her gallery for a while, as well as her list of skills and interests which encompassed my own fantasies. By the time my visit was over, the experience had been all that I had hoped for.
When I arrived at Mistress Cara’s door, she greeted me dressed in line with the fantasy I had described in my initial email: her long, slim legs clad in sheer black tights, along with remarkably high heels and a shiny black dress. I followed her up the stairs to her dungeons.
Once settled and with the paperwork out of the way, Mistress sat in a high-backed red chair and insisted that I sit before her and share the full extent of my secret desires. I confessed my obsession for nylons, especially black tights; and my desire not just to see them, but to wear them myself. Mistress feigned shock and disbelief as I described my own transformation once dressed in my own black tights, heels, lacy top, and absurdly short pleated skirt. Once dressed up I became a filthy plaything, I explained; a wanton whore, to be used for any filthy and perverted purpose she desired.
Mistress demanded that I kneel before her and continue. I confessed my desire to be used by women and men alike. I yearned to worship a woman’s sensual body however she wished, kissing, licking, tasting, and swallowing whatever she demanded. Mistress accused me of being a greedy little tart; but she also knew there was more. She insisted I continue with a full confession.
On my knees before her, I revealed that I lusted to be put to work by Mistress satisfying strange men. When I was dressed up as a cheap tart, with a short skirt barely covering my nylon-covered ass and tottering in my high heels, I yearned to walk the street to draw customers, and then get down on my knees in dirty alleyways, sucking men’s cocks and swallowing their loads. Mistress inhaled sharply with feigned shock and disgust, and accused me again of being a filthy prostitute who was desperate to put my perverted self on show.
Mistress demanded that I strip down and change in front of her. I slipped into a pair of black tights, then added some neon pink opaque stockings on top. I added a stretchy, lacy black top and my short pleated skirt; then slipped my feet into black high heels to complete my outfit. Mistress had me turn for her, and observed that I could possibly draw some customers if I learned to bend and posture and show off my nyloned ass and legs. Then Mistress directed me into one of her dungeon bedrooms for my first test.
Mistress lay down on the bed and her voice became sharp. She insisted that I beg for the privilege of touching her slim legs in her sheer black tights. I pleaded desperately until she judged me to be earnest enough; then she insisted that I worship her legs, stroking and massaging them, kissing and licking my way from the pointed toe of each shoe to each of her nyloned thighs. I spent considerable time proving my devotion to Mistress’ legs this way, intoxicated by the luxury of touching her fine ballerina’s legs through the sheer black material.
Only once I had demonstrated my devotion to Mistress’ body did she then turn to the second test.
Mistress insisted that I kneel again before her, and produced bright red lipstick which she applied amply to my lips. Then, she selected a dildo from several she kept at the bedside; it was time for my training. First she gently slid the plastic cock side to side over my bright red lips and demanded that I open my mouth and lick the round head. Then she penetrated my lips, sharply demanding that I enthusiastically suck the cock she shoved back and forth, in and out of my whore mouth. Her voice was stern, and her eyes severe: “Suck that cock, you filthy little tart,” she demanded. “Suck it! You love it, don’t you? Don’t you?” Her face was close enough to mine that I could feel the spittle strike as she commanded me to continue sucking the hard plastic cock she worked in and out of me. “You can feel him swelling now, he’s going to cum. Get ready! You’re going to swallow every drop of his thick cum from his cock!” I obeyed every command she issued from her own bright red lips.
Eventually Mistress felt that I had done a sufficiently passable job that, if I begged, she would slide a finger over my straining cock trapped inside my tights. I again pleaded and promised to do anything, anything at all for her. Slipping the dildo back into my mouth with an order to “Suck!”, she reached under my skirt and outlined my cock with a finger, sliding it up and down over my black tights. It was not long before, the dildo still clamped between my bright red whore lips, I came in a huge gush, completing my degradation.
The session was everything I had imagined. I cannot recommend the experience highly enough. From Mistress Cara you can expect:
– poise, strength, and command; her tone can switch from indulgent to severe in a flash, and she issues orders expertly
– understanding and encouragement to fully express and inhabit your deep and secret desires
– well-equipped dungeons, with an extensive female wardrobe and fetish gear of all kinds
– experience and insight, to guide you even to places you might hesitate to share
– intuition, to anticipate your desires and push you to your very edge
– flashes of generosity, if truly deserved
My next trip to London will unquestionably feature a repeat visit to Mistress Cars’s dungeons – and maybe more than one.