Sissy Training Stories: Learn, Grow, and Transform

Sissy Training Stories: Learn, Grow, and Transform

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Here’re 6 sissy training stories for you:)

A NEW LIFE

It was nearly 7 o’clock PM, and I was running late. I had gotten held up at work, and there was no way I could tell them exactly why I had to be home by a certain time.

Sissy Training Stories

How could I begin to tell them that my Mistress would be expecting me home at exactly seven in order to receive my night’s instructions? Not only would I sound pathetic, but I would be disgraced forever in my co-worker’s eyes.

I pulled into the carport and raced to my apartment. I had roughly fifteen minutes to be prepared for her. I opened the first of the four drawers of lingerie and girlie things that I had been instructed to acquire over the last year. I pulled out the full body, fishnet bodystocking and then stepped back and began to undress.

My male persona was systematically pulled off as I removed my tie, my white long sleeve shirt and my trousers. I do, of course, wear panties on a daily basis, per Mistress Purr’s instructions.

My work panties are always to be full cut and thick with ruffles and bows so as to make my ass look fuller and to create odd bulges in places that men would not have such lumps causing those around me to question what exactly is happening under my clothes. Thus far, no one has noticed, or at least hasn’t had the guts to ask.

I pulled my frilly pink and white panties off and sat on the bed as I began to slide the fishnet body stocking up my long, hairless legs. Being completely hairless was a stipulation of her keeping my secret to herself. I was allowed to keep my eyebrows but have to have them shaped regularly.

She also required that I grow my own hair out naturally, and it is now just below my shoulders and I am forced to wear it in a ponytail at work.

The bodystocking was crotchless and my…clit she calls it…slid through the hole as I pulled the rest of the suit up over my body. I’m not in the best of shape, but the black fishnet somehow masks that a little despite it clinging to every curve of my body. Or maybe I just hope that it does that. I stood and pulled the mesh suit around, making sure it was situated on my body properly.

Once I was happy with the result I reached back into the drawers for the pink and black panties with the bows on the sides that had long ribbons that fell down my long legs. The pink and black outfit I had been told to wear tonight was something that she called sissy chic.

Classy black mixed with sissy pink that flashed like lighting against the dark black. I caught myself wiggling my hips as I slid the panties up my legs and past my thighs.

Mistress told me I would end up acting girlie in ways I’d never have considered, and it seems she was right.

My gyrating accomplished the task of fitting the tight satin and lace panties to my ass, and I shook my head just a bit to clear the wave of sissy silliness that seemed to be trying to overcome my senses.

I returned the drawers and opened the second from the top. Inside was a steel boned corset as black as the night. It was something I had come to love as much as I hated it. It pulled my ample waist into an hourglass shape and pushed my chest upwards, allowing my plump A cup breasts to rest squarely on top of the corset giving me a very obvious set of titties, as she called them.

I had to learn to lace the device myself, as she was not available to lace it for me at all times. So I had been made to find lacing tutorials online and learn how to pull myself into it to the utmost. Sexy curves are what the world wants to see, she told me, so now I take about ten minutes to properly adjust the laces and pull my male body into the form of a buxom girl.

I hook the laces to the doorknob and step back which helps keep it all tight as I pull and adjust the laces from top to bottom and allow myself to be squished in the middle in order to become a more presentable sissy toy.

With the corset pulled tight as I can make it myself, I looked at the clock and saw I had about five minutes before I had to be ready for Mistress Sally’s call on Skype. I rushed back to the top drawer and pulled out a pair of black, opaque thigh high stockings with pink, lace tops and little black bows in front and pink seams down the back.

I sat on the bed once more and pulled the stockings up slowly as I had been shown. The stocking tops were then flattened and pulled up high enough for the garters that dangled from my corset to grab hold and keep them in place.

I knew I didn’t have enough time to do my make up properly, so I focused on being dressed and prayed that she would understand my delay. I went into my closet and pulled out the pink stiletto high heels with the ankle straps that had optional locks if she ever decided to really put me in a fix during my travels for work or one of my visits to her house for a weekend.

Heels, stockings, garters, panties corset and body stocking all in place. I was having a difficult time taking breaths, and one of these days I’ll remember to put my heels on before my corset. It’s nearly impossible to buckle the ankle straps when you can’t bend over easily. Sissy basics, but I still mess that part up almost every time.

My nipples rubbed across the fishnet across my chest and poked through the holes now and then. It was intensely frustrating, as Mistress had gone to great lengths to make sure my nipples became super sensitive and particularly perky, too, which makes work difficult when those little things decide to get excited as they brush against my shirt.

I thought that if I were to arrive on Skype dressed and with my nipples adorned with those harsh, metal alligator style clamps already in place that she may have some mercy on me for not having the makeup done. While I dread the metal teeth biting into my soft, sensitive nipples, it was well worth it if it meant she would continue to keep my secret and not punish me too severely.

I reached into the lowest drawer and saw all the torture/pleasure devices I had been made to buy. Nipple clamps, collars and leashes, various sizes of ball gags and dildos.

This was a treasure chest filled with leather, silicone, plastic and fur, and to be honest, it made me horny every time I opened it. I saw exactly what I wanted and grabbed the clamps with black puff balls that hung from little chains from the clamps themselves.

I pinched the ends of the clamps that opened like clothes pins, and settled the ends over my right nipple. I let the metal bite down into the midway point of my nipple and heard myself gasp out lout. That told me they were in the right place and I duplicated the effort on my left nipple. The puff balls dangled in front of my body and swayed back and forth as I walked through my apartment.

It was seven o’clock. I sat the my laptop and brushed my long brown hair into a pair of pigtails that popped up from the upper sides of my head and fell on each side of my face, framing it perfectly.

The pink hair ties completed the matching outfit and I heard the now ominous sound of Skype as Mistress called. I took a breath knowing full well she would not be happy with me out of makeup, but not answering was not an option, and would garner far more wrath that I was willing to risk.

As I grabbed the mouse and moved the cursor to the accept call button, I started to think to myself about just how I got here. How did I, a grown man, end up being the Barbie doll for a woman who loved little more than turning men into entertainment for not only herself, but for the entertainment of the world wide web as well? How did I get myself into this mess?

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