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michaeldelangel
1 week ago
Straight Male, 40
0 miles · London

My First Sissy

My First Sissy, Chapter 3

I learn a little more about Joe, and how far he is willing to follow Daddy's instructions.

That first night, after I’d watched Josie swallow my cum, we kissed as s(he) stroked my still-hard cock, until I told her Katie might wonder where I was if she woke up to find me gone. Josie looked up at me, still standing there in that schoolgirl outfit, now covered in saliva and cum. "Will you dream of me, Daddy?" s(he) said softly. "I don’t think there’s any way I could not princess," I said as I reached down and cares...

My First Sissy Chapter 1

The day I realised that my girlfriends brother looked sexier in lingerie than she did.

Before I tell you about the experience that changed my life forever, let me give you a little bit of background. My first girlfriend at university was called Katie. We got together in the first couple of months and were together for most of our time at uni. Although I was nervous the first time I met her family, we clicked straight away, and I regularly went back with Katie to her parent's place for weekends and holidays...

My First Sissy. Chapter 2

My girlfriends brother decides to show off a little more, and gets what (s)he asked for.

I barely made it through the rest of the night sitting there on the sofa next to Katie without going back upstairs and texting Joe again. I couldn’t stop thinking about how sexy he’d looked in that lingerie, and the thought that he might be up there now looking for another outfit to wear made my dick throb in my jeans. After a couple more hours of TV Katie yawned and told me she was tired, so we said our goodnights to her...

My First Sissy, Chapter 4

Josie comes to meet me in a hotel, and we finally give each other what we need

Over the next week, every single morning that I went into class, the only thing I could think about all day was getting home, locking my bedroom door, and video-calling Josie. Each night, she would show off a different outfit for me and tell me how badly she needed me inside her as I watched her fuck her little hole with the dildo I’d bought her. I’d tell her how to play with herself, how fast to go, how deep to go, and w...