A sissy as a Caricature of Womanhood

My second Mistress was a deep Female Supremacist and loved the fact that I shared the same sentiments.  She would constantly reinforce this imbalance through repeated efforts to crush my male ego until it no longer existed.

While she took over where my first Mistress had left off by taking me down the trail of forced feminization her thoughts and philosophies came from a different place.  She felt a man attempting to be a woman was insulting so her approach to sissies was to push things so far over the top that it wasn't like an attempt at womanhood, but an attempt at what no woman would ever be.  Just as a caricature greatly exaggerates the characteristics of a person, her choices for sissy clothing were ones that exaggerated the most feminine things but in a comical manner that didn't come close to passing for actual femininity.

Uncomfortable lingerie, extremely tight-fitting clothing, inappropriately bared flesh, tiny skirts that barely covered the genitals, boots and shoes that were uncomfortable and nearly impossible to walk in, shirts and tops that were too small so they barely covered my midsection, uncomfortable underwire bras that served no purpose since she wanted a flat chest.  Then she would take every fashion faux pas and use them all at once.  I would never pass as a woman and the goal was to be such a poor impersonation of womanhood that everyone, male or female would laugh.

Her appeal in doing this was to amuse herself when she would look at me and then relish the look of shame and discomfort on my face.

If I resisted in the slightest she would remind me that sissies were the lowest creature on the BDSM food chain and how they ranked below Dominant women, submissive women, and submissive men.