Sissy Crossdresser Roleplay – Mommy’s Sissy Crossdresser – NAT – A – 0016 – 6-12-23 – Part 2

I just knew you’d be back to see Mommy’s sweet boy becomes her sissy girl! Enjoy Part 2 of this sissy crossdresser roleplay!

We enter my bedroom together.

I sit down on the edge of my bed, crossing my legs.  Then I tell you to do a spin and model those panties for me. I want you to pretend you’re a girl and twirl for me! Your eyes light up, spinning around on your toes. “Very good! Do you want to try on the matching bra that goes with Mommy’s panties?” Eagerly you say yes, and I instruct you to dig the bra out of the hamper. You slip your arms through the holes of my pink, satin bra. Then you turn around for me to clip the bra together for you. Stepping away from me, I tell you to go look at yourself in the mirror. 

You love what you see!

You’re giggle and pose in the mirror as you did before- making cute faces and blowing little kisses at yourself. You stick out your butt and push up your bra to make your “boobs” look bigger. I watch you, studying your movements. I was worried you were going to change your mind once we got the bra on you, but you love that even more! Pretending you have a nice pair of breasts like me makes you incredibly happy. I’ve never seen such joy in your eyes before! It makes me want to push you even further. There’s one thing I want you to do that will make me believe you’ll be the sissy crossdresser I want.  

“You’re such a pretty girl, aren’t you sweetie?” 

This is the first test. Will you be upset that I just called you a pretty GIRL? With the biggest grin on your face, you say in your highest, girliest-sounding voice, “Yes Mommy, I’m a pretty girl!” Then you twirl about in front of the mirror some more. Wow! You LOVED being called a pretty girl! Maybe you are a sissy girl Mommy wants… I’m going to find out. I walk up to you and hug you from behind, kissing you on top of your head. “There’s just one thing we need to fix,” I say. 

Curiously, you inspect yourself in the mirror. 

You look yourself up & down. What could Mommy want to fix? I reach down and gently tap your penis. It’s still sitting in the front of your panties, creating a bulge that shouldn’t be there. “This. This is what we need to fix. It should be smooth in the front if you’re a girl. Don’t you want to be Mommy’s pretty little girl?” “Yes mommy!” you say. I can hear in your voice you desperately want to become my pretty little girl. I instruct you to carefully tuck your penis between your legs. Looking at how smooth you are in those panties, you’re amazed how something so simple makes you look like a real girl! I tell you how beautiful you are, and i’m so happy that you’re my little sissy!


I have a passion for writing naughty stories, and I hope you enjoy them as much as I do. If you enjoyed Part Two of this stepdad virgin age play and want more, listen to me read my filthy story to you in my sexy voice, and get extra-spicy details in my audio!

If you love erotic stories like this one, check out my other blogs!

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