Nancy’s Sissy Training

So this is the story of how I began my sissy journey… 

Thinking back in my life… I’ve always had the qualities of a sissy… I used to prefer being with girls (as friends), and doing more “girl” things. I remember being a young boy, 5 years old, and wishing I could wake up as a girl. I wanted to wear pretty dresses, high heels, have long hair. 

When I entered my teens, and I started developing body hair and facial hair, I hated it, I wish I didn’t have it. In secret, i would often wear my mother’s clothes, I’d try on bras, panties, dresses, heels, I absolutely loved it! I remember most a beautiful black satin women’s blouse – it was my favourite!

The feel of satin against my skin, was amazing. That’s when my craving to be a sissy began. I would read sissy erotica online, I don’t know how I first came across it, but it opened my mind. Stories of failed men, who were embracing becoming sissies. Men who were coerced but secretly loved being transformed into sissies, who were renamed and committed to serving their masters. Even stories of men becoming full time sissies and going to the extremes of taking female hormones! 

I was fascinated by these stories, it drove my desire to find a Master or Daddy to help push me in my sissy journey. With the motivation of avoiding punishment in being exposed! As I’ve got older, I had not yet found the right person for that.. until I met Daddy! I’m so excited to begin my sissy journey with him!

panties for sissy


The day has finally arrived! The day I meet my Daddy. We met online, and he is visiting my home for the first time to start my sissification training. He has given me a beautiful new name – Nancy. 



He gave me strict orders on how I should look for his arrival. I was to wear panties, tights, leather trousers, a satin blouse, and some heels. I put on the panties – the satin felt amazing against my sissy clitty and got me excited. I slid the sexy tights up my legs, I loved the feel of it against my skin. I then got the satin and lace bra, and satin blouse, which made me instantly look even more femme (yet very clearly still a sissy male), if that was possible. I put on the leather trousers, which with the heels on, made my entire outfit look perfect for a sissy’s first time. 

Daddy wanted his sissy to have a few finishing touches. I put on a Pearl necklace and Pearl earrings. Then I got the bright red lipstick and applied it to my lips. I looked like a total sissy. I was getting butterflies just thinking about it. I was so anxious – as to let Daddy in I would have to use a hallway I share with neighbours – which could get me caught and exposed as a sissy before I’ve even started!! But I wanted to please my Daddy so that he could progress me in my training as a sissy, so I obeyed and trusted him. 

He arrived on time, as planned with some bags. I let him in, we quickly made it into my flat, before anyone could see the complete sissy I was. He asked “Give your Daddy a kiss Nancy”, and we had a passionate kiss. I got Daddy a drink, and we sat down and got to know each other for a bit. It was at this point, Daddy suggested we do a sissy photoshoot. I am eager to please, so I agree. Daddy gets me to stand in all sorts of poses, showing off the sissy outfit I’m wearing, and how pathetic a male I am. He even gets me to take a photo holding my passport photo next to my face.. 

Daddy then explains to me, that I am committed to becoming a total sissy. And he believes I will achieve my sissy dreams, but he keeps photos, just as some motivation for the sissy to follow orders and continuing in her sissy journey. So that a sissy will work its hardest through fear of being exposed. So that the sissy will obey all orders. 

I wonder to myself – what on Earth have I signed up for?! But I try and shake myself back into reality. Daddy has those photos now – I have to carry on with my sissy journey now regardless. But also – I’ve always wanted to become a sissy! This is exactly the kind of motivation I need to prevent me from chickening out again. 

Daddy and Nancy become more relaxed around each other, and Daddy orders her to give him a blowjob. Daddy talks to Nancy and explains to her his preferred way for her to give blowjobs, as she does it, training her. He also starts taking more photos of her for his private gallery. 

Read the next chapter to find out what’s in store for Nancy next! 

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