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Spoil Your Sissy Spa Day!

Are you ready for your very first spa day, my pretty sissy? You know, you have been such a good, obedient little sissy daughter, I think you deserve it!  I made all of the arrangements and we are going to have such a wonderful time together, you and I.  Did I happen to mention that [...]

My Pretty Sissy Shopping Spree

Aw, my pretty sissy returns for the love, guidance and discipline that only your Mommy Mistress Courtney can provide.  Welcome home my pretty sissy.  Did you like the collegiate wardrobe I bought for you?  Such a grown up college girl sissy you’ve become!  My my, you sure do make your Mommy Mistress proud.  I love [...]

Growing Up Sissy, My Pretty Sissy

Hello my pretty sissy.  How is Mommy Mistress‘ little darling sissy today?  I hope you are having gloriously wonderful sissy day today.  Mommy Mistress picked up a few things for you while I was out shopping.  I hope you like them.  In the hope of making you feel a bit more grown up, I went [...]

My Pretty Sissy and The Feminine Rites of Passage

Welcome back my pretty sissy. As you recall from our last visit via the my pretty sissy blog, I was explaining why you may have felt the strong urge to not only be a sissy, but to act as a very young sissy, a little sissy girl, in fact. Now I know that [...]

My Pretty Sissy Post – Sissy Coming Out Party

Now that you have your sissy coming out party, my pretty sissy, I think that it’s time we really have that heart – to – heart Mistress Mother and sissy daughter talk. You are getting to be all grown up now and it’s time to put away all of the little girl things [...]

Oh The Sissy Places We Will Go, My Pretty Sissy!

My pretty sissy is all grown up now.  But we still have many milestones to cross and broomsticks to jump.  Your sissy Coming Out Party was just the beginning of your sissy journey as my sissy daughter.  Speaking of broom jumping, I just love the idea of you being all dressed in white like a [...]

My Pretty Sissy Will Graduate From Sissy Charm School With Flying Pink Colors!

Oh your Mommy Mistress is so excited about the idea of you being my pretty sissy debutante at your very own cotillion. I am wondering if there is any way that we could merge your “Coming Out Ball” with World Sissy Day, wouldn’t that be fun? I am envisioning a sissy celebration that [...]

My Pretty Sissy May Be Having A Coming Out Ball!

How is My Pretty Sissy today? Your Mommy Mistress has all kinds of sweet sissy fun waiting in the wings for my sissy daughter. I’m not going to unveil everything all at once. You know that your Mommy Mistress has to keep you en pointe, no? I don’t want you just [...]

Mommy Mistress Courtney Says Celebrate World Sissy Day on August, 16th

Hello My Pretty Sissy! Today I found out something really exciting for all of my pretty sissies. August 16th is World Sissy Day! Hip hip hooray! So, with World Sissy Day being less than a month away, we need to plan, girl! I would love to know what your thoughts [...]

Mommy Mistress Courtney May Have to Take You Over Her Knee, Pretty Sissy!

Welcome back My Pretty Sissy.  I know you are probably wondering what other ways your Mistress cum Mommy will do to shape and mold you into my perfect, pretty sissy.  There will be many changes.  The changes that I outline here are just the tip of the iceberg.  Since you are such a raging sissy, [...]