A Failure of Self Discipline

I heard the vicious hatred in my blackmailer's voice as she hissed her venom into my ear: "You're a slut and a whore, sandra, and just how much of one, you're going to learn right now."
Mistress Andrea, as she insisted I call her, rose and addressed the room: "Ladies and gentlemen,” she called out, “having sampled sandra's goods, several of you have asked whether her services can be purchased for your private sex parties. Well, I'm pleased to announce that sandra here has asked me to manage her in a brand new career in outcall sex services!

Sandra has begged me to pimp her out, so from now on, she'll be working parties and individual engagements on nights and weekends! She's particularly interested in s/m parties and glory-hole situations. Sandra will service women orally, but at her request, I’ll be keeping her sissy bits locked up in a chastity…while she still has them…so mostly, sandra will be of interest to the guys." I moaned in misery at what Mistress Andrea was doing to me. I hadn’t asked any such thing, but I didn't say anything - I couldn't - my mouth was full of cock.

This horror all started with a simple lapse of self-discipline, after a rough break-up. Though for years, in fact, since my teenage years, I’d been fascinated with feminization, I’d managed, mostly, to avoid it. Sure, like all boys, I’d snitched some lingerie from family and friends, and I’d masturbated to pornographic movies and pictures where I was imagining myself the actress, rather than the actor, but I’d mostly managed to keep my cravings in check. I did go through a few phases where I’d buy makeup, wear it around the house when I was alone, and I’d used some of my partner’s sex toys on my backdoor, but there was never anything that would show on the outside. I’d never shaved my legs, or worn full woman’s clothing, or plucked my eyebrows, or grown out my hair. I just lived a normal life, on the outside, with the career at the centre, and my relationships were normal, heterosexual ones.

But in my depression after my wife left me, I finally gave in, after the decades of denial, to the urge to explore my interests in feminization. Even then, I was cautious. I searched all over the internet for the right opportunity to indulge safely, finally finding one of the growing number of well publicized, public transformation salons catering to men who wanted to experience feminization. Figuring that a public business that advertised openly on the internet would be safe and discreet, I booked an appointment with a transformation salon downtown, for a four-hour feminizing makeover and beauty lesson.

Well, the experience was all I could have hoped for. My makeup artist, Jade, was friendly, attractive, and knew everything there was to know about making a guy look more feminine. She had great hands, and made applying everything a sensual experience. Between the cleansers, the lotions, the makeup, the prosthetics, and the clothes, after the four hours, I actually looked reasonably feminine, and attractive. I simply adored the feel and taste of the rich lipstick on my lips, and the way my long, manicured nails looked on the ends of my fingers. My eyebrows were just a bit thinner, but not so much it would be noticed at work. My calves felt tense in my heels, and it was a sexy tension I really loved. Of course, I still moved like a guy in a dress, and a somewhat bulky one, as I had to wear a long-sleeve blouse to conceal the hair on my arms, and two layers of pantyhose, to conceal my leg hair. And, of course my voice was all wrong. But, there was enough done to give me that first addictive thrill, and I had to have more. I booked two more lessons the same day, to teach me to make myself over, and to start learning feminine deportment.

For months, everything was great. Andrea, who owned the salon, started joining Jade in my lessons, helping me learn to be “sandra,” my femme self, while fitting it all in with my regular work life. Andrea really befriended me, and started coming over to my house to coach me in feminine behaviour at home. She not only finished my makeup lessons, she also taught me to keep my body hairless, to decorate my apartment in a more feminine manner, and to adopt a feminine voice. That last part was the hardest, but Andrea sat with me while I read her the text from women’s magazines, usually about “How to be a Tigress in Bed!” Andrea also motivated me to diet, and over time, she started inviting me to her home as well. About the only odd thing in that period was that though I wanted to quit smoking, Andrea insisted I continue, partly to help me take off that last ten pounds, but partly to remind me to hold my hands in a feminine way, and to think about my lipstick when I’d see it on the cigarette filter. She did change my brand though, and got me smoking long women’s cigarettes. She even increased the number I would usually smoke, and had me smoking one every half hour, even when at work. The few smokers outside thought it was odd, but when I said that I’d told my wife I had quit, so didn’t want any other cigarettes than my wife’s brand around the house, they just laughed it off.

Additional Reading:

Ready to start your training?

Submit your application today!


Mr. M

I have come to greatly appreciate the training that You and your Staff have provided to these girls and believe that the House will provide her the best possible training to be the kind of sissy I would like to… Read more “Mr. M”

Notify of
oldest most voted
Inline Feedbacks
View all comments