Sissy Crossdresser Roleplay – Mommy’s Sissy Crossdresser – NAT – A – 0016 – 6-12-23 – Part 1


What happens when Mommy finds her son trying on her panties? Does she get upset? Or does she encourage her son to try on more of her clothes? You’ll find out when you read this sissy crossdresser roleplay!


It’s just me and my young son living at home together. 

You usually get home from school about an hour before I get home from work. I get home, hug you, and start making dinner for us. I texted you earlier today that I was probably going to work for an extra hour, so you could have a little snack before I get home. Thankfully though, I ended up leaving work on time. When I got home, I expected to see you on the couch watching TV or playing video games as usual. But you weren’t. The house was oddly quiet. I quickly walk to your room to check on you and see the door is cracked open. I look through the crack and can’t believe my eyes. 

My son is wearing nothing but MY PANTIES!

At first, I expected to catch you jerking off in my panties. It would have been awkward, but masturbation is something I knew I would naturally have to deal with as the mother of a boy. However, that doesn’t seem to be what’s going on here…  It seems like you enjoy wearing my panties. You start flirting with yourself in the mirror, and I see your entire personality change. I continue to watch as you practice doing girly things like blowing kisses, giggling, & twirling your hair in your fingers. I’m stunned at what I see.

Could my son be a sissy? 

Could I be so lucky?! I love my son very much, but I always wished that I also had a daughter to do girly things with. Could my son be the one who makes that dream come true for me? I have to find out! I push the door open the rest of the way, walking into your room. You jump and turn around to see me staring at the panties you took from my dirty laundry to wear. “Mommy?! Oh NO! Please don’t look, Mommy! I’m sorry! I promise I won’t wear your panties ever again!” “Why?” I respond, “Don’t you like wearing Mommy’s panties? You looked like you were enjoying yourself.”

Embarrassed, you admit you love wearing my panties.

You confess that you love wearing them so much, you wish you could wear them all the time! At first, you thought I was mad, but I look very pleased by your answer. If you want to try wearing other girly clothes, you shyly nod your head. I walk out of your bedroom, telling you to follow me. Nervously, you ask if you’re in trouble. I turn around and take you by the hand, staring deep into your eyes. I brush your bangs out of your face and say “No sweetie, you’re not in trouble. We’re going to Mommy’s room to find more pretty clothes for you to wear!” Then I kiss you on the forehead before leading you to my bedroom.



I have a passion for writing naughty stories, and I hope you enjoy them as much as I do. Don’t miss Part Two of this stepdad virgin age play! If you need to finish the story now, 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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