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Sissy Anal Training with Ms. Piper

Hugs and Kisses (and Spanks!)

So you want to please your Mistress Piper. What better way to please her than to give up control of your sissy fuck hole?

(For the record, I’m talking about your downstairs fuck hole and not that pretty little-lipsticked mouth!)

Anal training is an important part of becoming a sissy. Learning to use your ass to please a Mistress is a beautiful act of submission. See, as a sissy, you’re unable to please your Mistress the traditional way a man pleases her because your clitty makes a poor substitute for a cock. You have to learn other ways to please, and learning to be penetrated is one of those important ways to please your Mistress.

Giving up your ass (aka pussy) to your Mistress shows that you trust her.

Let’s face it, ass play can feel really good, or it can feel bad. You chose your Mistress for a reason, and one of those reasons is because you trust her to take care of your needs, so you don’t have to. Allowing me to guide you to the heights of anal masturbation shows that you do indeed trust me.

Learning to love getting fucked in the ass will take your feminization to new heights.

Men aren’t naturally built to be penetrated, women are. When you train your bottom to receive pleasure and bring satisfaction, you are embracing the feminine you. Transforming your ass into a sweet little pink pussy hole is like taking the express ramp to sissydom. It’s essential to feminization, so don’t cheat yourself or your Mistress out of this pleasure!

Are you ready to surrender that hiney to Mistress Piper, but not sure where to start? Invest in a small anal plug, and while you’re at it, grab a medium plug too. Then give me a call and let’s begin your anal training right away!


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We both know that’s merely a rhetorical question, don’t we, sissy? Of course, it is! It’s the same thing that always there…

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You are a sissy. As the name implies, you are effeminate, unmanly and, in general, a cream puff. But you remain “rough around the edges.” Too hairy, not graceful enough, poor comportment and you still smell like a man. How exactly do you intend to . . . → Read More: Sissy Beautiful to No End

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Sometimes You Need A Strict Mistress800-356-6169

Oh, sissy, you’ve been a very bad girl! You’ve been caught with your hand in your panties again, and you know good girls don’t play with their clitty without permission!

You try to hide your hard little sissy stick, but I don’t let you. I make you . . . → Read More: Is Your Bottom As Red As Your Face, Humiliated Sissy?

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I can practically feel spring coming. And you know that means I’m already planning for my sissies to get some nice pampering time at the spa. Well, if I’m gonna pamper your toes and get your fingernails done, I’m gonna go ahead and sign you up for . . . → Read More: Panties for Spring

Ms. Courtney Presents The Masturbation Interviews

The Masturbation Interviews

Hey, strokers! Have you heard about Mistress Courtney’s Masturbation Interviews? Sexy interviews with voluntary participants, sharing their masturbation experiences. Yes, even YOU can be interviewed, if you so choose. Read THIS for details on how you can have your masturbation story shared. Ms. Courtney loves hearing from you!

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Where You See Failure, I See a Sexy Sissy Opportunity

Hope you are ready to accept a change in status, young man! You see, primates like you and I separate ourselves into hierarchies. Sexual prowess, particularly for the man, is rewarded by moving up the ladder. Incompetence, particularly sexual ineptitude, is punishable by falling . . . → Read More: Sissy Opportunity