Shopping Sissy Slave – Turning a Sissy Fail Into a Sissy Win!


Hello, my sexy perverts! Today, Mistress and her sissy slave are back! When we last checked in with them, Mistress had given her sissy slave some rules regarding his appearance and then evaluated his feminization progress.  And although he had done some things on his own, it was overall a sissy fail. So, today he is going to be our shopping sissy slave to turn this sissy fail into a sissy win!  You may recall:



The Sissy Appearance Rules:


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.

You will shop for most of these items together with your Mistress who will approve the purchase.

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


A Sissy Fail


First, I conducted a review of his closet and dresser drawers.  The sissy lingerie situation was bleak.  I found a drawer full of very unattractive panties, control-top pantyhose, and one random bra.  The panties were from a multi-pack of pastel-color briefs and were the fullest coverage panties I had ever seen. The panty drawer was definitely a Sissy Fail.

The closet was a bit better.  I did find a beautiful black cocktail dress and a pair of subtly sparkly black kitten heel slingback mules.  An outfit that sissy slave put together himself.   The closet was a very minimal Sissy Pass!

And finally, we needed to do something about his joyless skincare routine.  It seemed pretty effective but not very much fun.  And of course, we should replace all of his makeup that I threw away.  I would definitely be doing a lot of shopping with my sissy slave!



You Need Several Looks


So, my sissy slave, we know what you are to wear when you are at home and at work.  But I want you to have several looks for when we go out.  One for brunch and going out with the girls.  And another that is more elegant for going out in the evening. The last one is a sexy club look that you already have.

Finding your sissy style is going to take patience and time.  And will cost money.  But in the process, you’ll discover so much about yourself.  You’ll get to know what styles you like wearing and what makes you the most comfortable.  All of that may already be inside you.  We just have to find it. 

We could shop online for these outfits but it’s important to try a lot of things on, especially at first.  Shopping with my sissy slave made the most sense.  And speaking of trying things on, we need to take your measurements before we go so we will know what sizes to start with.  

Since you’re in your tiny g-string that you’re required to wear at home, I’ll measure you now.  We’ll start with your waist, your bust, and your hips.  It’s a little different than measuring for men’s clothes.  And if I decide that you need any padding, like breast forms, butt padding, etc we’ll need to measure you again.  


Shopping With Her Sissy Slave at the Expensive Mall


We’ll be starting this exciting process together tomorrow.  Bright and early we’ll meet with a personal shopper that I arranged for you at Nordstrom.  I think it’s important to begin at a department store to have the largest variety of brands, styles, and sizes available to us. Yes, I know that Nordstrom is at the “expensive” mall.  But you can afford it.  And besides, that’s where all the good shoe stores are!

It’s also where Victoria’s Secret is – a store you desperately need.  You need new pretty panties, a few bras, and some silky stockings.  And we’ll also go to Sephora where I’ve scheduled a makeover for you!  We need an expert to figure out which products are right for you and what shades and types of makeup you should use.  They will also teach you how to use them.  



So, my sexy perverts… Shopping with her sissy slave is going to be a very full day! I can’t wait to see what they buy…

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.