feminine sissy slave - submissive boyfriend

Feminine Sissy Slave

Well, my sexy perverts, last time we made it to the end of all the rules. I know it seemed like a lot but, as you know, your Mistress Roxie loves sexy rules for her sissy slave and finds them very arousing. Especially the sexy ones that involve chastity. I’m sure this is not a surprise to anyone!

The first order of business after learning the rules was, of course, evaluating the sissiness of my feminine sissy slave and how he complied with all of his “Rules For a Sissy.” As a reminder, these rules were and remain as follows:

- - Your attire and feminine sissy slave appearance will be entirely at the discretion of your Mistress and will most of the time reflect a feminine and sexy appearance

- - Although your Mistress has the final say in your daily look, you will be responsible for choosing an outfit that you believe will please her

- - Your default “outfit” at home will always be a micro thong/g-string. However, your Mistress will often add to or change this requirement with lingerie, clothing, shoes, makeup, hairstyles, etc.

- - You will shop for most of these items together with your Mistress who will approve the purchases

- - You will be responsible for learning what clothing, makeup, and hairstyles look good on you as a feminine sissy slave and will also please your Mistress. Your Mistress will help you with this by evaluating your current and ongoing looks and styles and providing you with ways you can improve

Is he a Sissy Pass or a Sissy Fail?

With some apprehension, we started the evaluation process immediately. As much as my subby boyfriend tried to be the best feminine sissy slave he possibly could be for his mistress, he had a lot to learn. He had been going it alone and really needed some help. At least to meet my standards. First, was a review of his closet and dresser drawers to find out if they’re a Sissy Pass or a Sissy Fail.

The Lingerie Situation Was Bleak

I found a drawer full of panties from Target. Of course, you could find decent panties at Target but these were not among those. These were from a multi-pack of pastel-colored briefs – the fullest coverage panties I had ever seen. I guess they made my feminine sissy slave feel pretty but we could do a lot better. Perhaps we could keep them as punishment panties. The panty drawer was definitely a Sissy Fail.

The stockings, bras, camisoles, etc situation was just as grim, if not more so. There was one pair of control top pantyhose that looked like they were sold crumpled in a plastic pouch. I looked at his toned abs and back to his control top hosiery and sighed. Yes, we did have a long way to go.

I also found a single bra (size 32 D) that he said belonged to an ex-girlfriend. There were no garters, no thigh highs, no bralettes, and no girly sleepwear. His lingerie collection was a Sissy Fail.

My Feminine Sissy Slave’s Closet Was Shocking!

I opened the large walk-in closet expecting it to be sparsely populated with work suits and workout clothes, which it was. Except for a bit of sparkle that caught my eye. When I looked closer I saw a beautiful black cocktail dress. It looked like it would fit him in a form-fitting but not tight kind of way. The fabric was sparkly in a subdued, tasteful way and the length looked like it would be about mid-thigh. And it had a flatteringly low neckline and long sleeves.

“Where did you get this dress?” I asked him. He looked at the floor and said that he bought it online and wore it to a Halloween party last year. Then I noticed a pair of subtly sparkly black kitten heel slingback mules. A really smart choice. “Did you put this together yourself?” I asked my feminine sissy slave. “I did. And I wore makeup and a nice wig too,” he responded proudly. There may be hope after all for my subby boyfriend. The closet was a very minimal Sissy Pass!

The last stop in our sissy inspection was my feminine sissy slave’s bathroom. He had a modest skincare routine that seemed pretty effective but not very much fun. More Dermatologist recommended and less Instagram Beauty Guru. We needed to find a middle ground there somewhere.

The Makeup Went Directly in the Trash!

He then showed me the little drawer of makeup he bought for the Halloween party. I scooped up all of those drug store items and dropped them in the trash. “You can afford better. We’ll buy more,” I said. My feminine sissy slave’s bathroom was a Sissy Fail but with a lot of potential.

So, my sexy perverts… what do you think our Mistress and her feminine sissy slave are going to do next? More importantly, can you believe that she threw away all of his makeup? And criticized his perfectly fine skincare routine? Let me know what you think in the comments below!

Totally Lost? Not sure what’s going on with all this domination and feminization of a sissy slave? Don’t worry! Head over to Part One: A Sissy Slave Boss and read from the beginning.