Posts tagged sissy

My Pretty Sissy Boy – Femdom Phone Sex – Part 2

My Pretty Sissy Boy – Part 2 Running my hands soothingly up and down his arms and massaging his shoulders in readiness for the tension which was about to flare, I said: “Alexis, before I get you dressed in your beautiful girl clothes, there is just one thing that you have to do. Let me remove ALL of your body hair. It has to go.”…

Read More

My Pretty Sissy Boy – Femdom Phone Sex – Part 1

My Pretty Sissy Boy – Part 1 The atmosphere had been a little strange at home since I caught my stepbrother, Alexander – now named Alexis – wearing my panties. I only had to look at him at the breakfast table to make him blush scarlet and, as I held his gaze, I could visualise that beautiful, thick cock hardening in the silky panties I…

Read More

Panty Thief – Sissy Phone Sex – Part 2

Panty Thief – Part 2 Sitting him back down again, I slid the smooth black leather stiletto heels onto his stockinged feet. Telling him to stand up carefully, he took a couple of unsteady, excited steps towards my full-length mirror and then stood still to admire himself. With his long legs in those sheer stockings and the six inch stilettos, he did look absolutely beautiful….

Read More

Panty Thief – Sissy Phone Sex – Part 1

Panty Thief – Part 1 I had a complicated relationship with Alexander, my stepbrother. Suddenly introduced into each other’s lives when his father had married my mother, we were expected to behave like brother and sister. This was difficult at times since we found each other extremely attractive. Alexander was slender in build and, despite very different colouring, actually looked quite a bit like me….

Read More

Sissy Roleplay – Let’s Play Dress Up Part 1 – STE – A – 0009 – 07-11-23

Sissy Roleplay – Let’s Play Dress Up Part 1 – STE – A – 0009 – 07-11-23 Hey! I’m so glad you decided to come over today. I’m really excited to get to spend some time with you. I feel like it’s been so long since it was just us, you know? You look really nice today, too. I see you’re all dressed up! I…

Read More

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

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…

Read More

My Sissy’s Humiliation with TSA Part 2 – FAI-A-0001-6-19-2023

 My Sissy’s Humiliation with TSA Part 2 – FAI-A-0001-6-19-2023 To continue My Sissy’s Humiliation, we walk into a small white room that is only decorated with a bench along one wall, and 3 plastic chairs along the other.  The agents start asking Lexi all kinds of questions. I walk over to one of the chairs and sit back so I can watch the show.   Lexi…

Read More

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

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…

Read More