I’m a sissy and I know it

Is something I hope my sissy would say proudly back to anyone trying to make her feel less than, when she’s dressed.

My first experience in kink with feminization was encountered as most things are in this realm, with a healthy dose of humiliation and degradation rooted in a lot of bad porn. It was a request by a most auspicious businessman and I remember his email and Forbes-esque picture quite clearly. It went something like this…

“Hi Mistress, I am looking to be brutally talked down to and made to feel like less than a man. Please dress me up in a big frilly dress, panties, and a wig and tell me how much you hate me.”

Simple enough and it was his time and his money so I granted his requested. It didn’t take long into a mid-spat to the face that I genuinely felt…contrition. The session ended and afterward I dug deeper into the online world of forced feminization. I was strangely surprised by all I learned and just how stark the difference, at least, to me between forced femme and sissification.

I had ‘forced’ a guy into a crude feminine box for 90 minutes in a pair of ill-fitting hot pink shoes, a tight and gaudy, over the top babydoll dress, lacy bloomers and berated him with insults that could make even the most confident of men rattle inside.

But, something had been lacking…and it was missing from the entire session. It was my own desire.

As I had understood it the terms forced feminization and sissification were synonymous however I was noticing a clear distinction between the two in my own interpretation. Both are mostly psychological. In my opinion feminization is about being more like a woman, where sissification is being less of a man. When you factor in the ‘forced’ aspect, that changes the context. Now one is being forced to be more like a woman and usually when anything is forced there’s a hollowness that comes with it. When it’s a punishment it’s understood that it will have to be forced because generally no one likes to be corrected, let alone if it involves pain.

Even the most masochistic kinkster has something they don’t enjoy that must at times be forced on them if consented. I realized I didn’t want to force anyone to dress as what I deemed the superior of gender. I wanted a doll of my own to play with. If anything it should be a honor to don some of our attire and get a glimpse into the wonderful world of womanhood. When you take that high-heeled step closer into our world it is inevitable that a guy would take one step further away from manhood in the process but a balance can be maintained, like a tug of war. This can be as temporary or as long-lasting as they (or you) like.I had a wanting now.A wanting for a real sissy of my own…

Over the years I have encountered many other submissives who requested forced feminization, whom I obliged but my heart wasn’t in it. I pushed my wanting to the back burner of my fetish list as I had a buffet of other delights to take in as often as I liked but it was always in my mind. When I met Puppy and he confessed he’d always wanted to be dressed up like a woman I jumped at the opportunity.

He showed me a laughable picture of him dressed up for a previous girlfriend but it was very basic. I wasn’t sure what he had in mind considering he’d been exposed to a never-ending stream of porn that mimicked the session I had orchestrated years earlier. But I knew this time it would be different. I didn’t ask his input, I didn’t care to get his twisted ideas about how this was going to go so I simply asked what I normally ask…

“Do you trust me?”

“Yes, of course Mistress,” he replied just as I had thought he would.

A few days later I dolled up only half of his face with lipstick, eye shadow, and blush. When he was allowed to view himself in the mirror he was simply captivated by what was reflected back. That was all I needed for a green light as I sat up at night fantasizing how I was going to turn him into the sissy of my dreams. Since that day I have designed a five stage, four year sissification training program for him. We will do this in conjunction with his regular submissive training. It is involved and has become something we both crave, eagerly anticipate, and are committed to.

I bet you’re wondering what kind of sissy I was aching for?

Let me introduce you to my lovely creation called ‘Josy’.

Josy is a petite, slender build of a girly-girl. And even though she’s far away at the moment she is still in my service. Josy lives a reverse 1950s style lifestyle with me when we are together. She always tries to look her absolute best in mostly swing style dresses, fetches me a well balanced dinner for when I arrive home after a day of her prancing around cleaning in her uniform. Josy is learning how to give sensual foot rubs, while being a good listener. Her future training will include perfecting her future Femdom wife’s favorite cocktail. And I love taking my girl to attend drive-ins, sexually training her for my, and those fortunate few’s, pleasure, but most of all I just love dressing her up. She knows that her life’s fulfillment is being at my side, I am just not sure she realized mine was being at hers too.

I can’t thank Josy enough for all that she has fulfilled in my little Mistress heart. She’s the girl I’ve always dreamed of and I hope she’ll continue to grace me with her slutty, pretty, slightly-bratty presence for as long as I want.

I am so lucky to have found a sissy of my own.