Cross Dressing and The Urge Behind It

It was only a few decades ago when I was conducting real time sessions, a segment of my clients were cross dressers. That was the general term of the day to describe straight men who love to dress up in women’s clothing.

These men came to me as a safe haven to be able to dress in frilly panty, wear makeup, pumps and a wig. These men were married and owned businesses.

It’s interesting to note that when they dressed up under my guidance and supervision in wig, makeup and female garment, there was not one drop of femininity oozing from them.

My cross dressing clients who came to me were masculine looking and in some cases over weight. The point I’m making is that putting on makeup or a piece of female garment to some of my clients was like relaxing or unwinding with a glass of martini. Looking pretty or even passably attractive was not the objective.

When they came to me, it was not to be transformed to total femaleness. This was merely a part time endeavor of escapism and a feeling of liberation. I feel it was a psychological transportation to a time of safeness, protection and love.

Perhaps for a brief time with me, they wanted to regress to a comfort zone or go back in time to their childhood where they felt the closeness and love of their mother. Maybe their choice of garment they loved to wear i.e. house coat and slippers, their mother’s favorite lipstick color or even hair style brought them closer to the memory and bosom of their mother.

These items of choice to wear as a means to connect to motherly love in my opinion were triggers to a stress free memory of nurturing.

I did have a handful of sissies and alpha males who wore women’s clothing purely for sexual and erotic gratification. Their motivation was definitely to look, behave and feel like a woman in every way possible.

They sought my guidance to be transformed, some for the long haul and some in part time increments. The training I provided for these individuals were tailored to the goals we discussed. Some of my sissy sub clients wanted not to be confined to their fantasy indoors. They wanted to actually look and pass for a female to venture out in public.

Looking attractive and feminine was important to confidently go out shopping alone or to a bar without being harassed or worse.

Even today cross-dressing or sissification is more open and less closeted, but there are some individuals who remain psychologically suppressed and are afraid to allow themselves to be who they truly are.

They require hand holding, guidance and my supervision.

Back then before the internet, when my cross dressing clients came to see me, I provided understanding, stern training and a nurturing hand that left them safe and secure.

When they left my play space they went back to their family, kids and business until the next time they felt an over-whelming itch that needed to be scratched.