©2018 Hailey Heartless. Vancouver, British Columbia.

Your descent into forced womanhood: how it's going to happen.

August 11, 2017

You see my ads on an advertising board while looking for fun on the weekend. "Sissy training, not my thing," you say, but my blue eyes linger in your mind as you continue to browse.

 

A week has passed, you're looking for fun again, and you see my ad once more. You click on it for a laugh, and you're directed to my website. You look at my pics, shrug, and go watch Netflix. 

 

It's Saturday night, you're at home drinking alone. You turn on your PC, open your web browser and it's still on my website. You browse a bit, read some of my journal, and read about the various services I offer. "Endorphin ladder," you say in your head, "sounds interesting. I'm no sissy, but I'm curious about what she means." You've had a few drinks and you're feeling a bit bold, so send me an inquiry asking me about an endorphin high. 

 

Sunday afternoon I text you, "I'm available for sessions this afternoon but my next availability isn't until Thursday." You shake it off. 

 

Wednesday night, you're looking at TS porn. They're so beautiful. You come back to my website and look at my gallery. You send me a text, "are you still available tomorrow? I'd like to try the pain thing." You send a second, "I'm also into a bit of light humiliation." You go to bed. 

 

Over the next couple of days we arrange a Saturday session. As negotiations progress, it becomes clear to me that you're more interested in the humiliation than the pain.

 

You arrive at my dungeon on Saturday, clean, sober and nervous. "What am I doing?" You shake your head and open the door. 

 

I sitting on a spanking bench holding a cane. I direct you to come in. You kneel at my feet. As I begin explaining the rules and what I expect of you, I direct you to worship my body, pointing out all the places I want you to pay attention to. My feet, my calves, my thighs.... 

 

I stand you up, running my hands over your body, I size you up and determine the best way to begin your transformation. I put you in your outfit for the evening, I have a few to choose from. I attach you to a cross and begin work on your makeup. You're starting to look like a proper sissy... 

 

I extract your dirty thoughts using an array of tools and skills I've acquired from my years of lifestyle kink. You tell me all about what you like to do, why you visit girls from disreputable website, and why you deserve to be punished...

 

What happens next is a matter of what naughty thoughts I extract from you, but I assure you, I will test your ability as a sissy, and let you know what it means to be my little plaything.

 

Over the next week you think back about our encounter. You laugh at being put in a wig and a cute little outfit. Those thoughts turn to fantasies, those fantasies turn to cravings. You think about something I said, "if you keep coming back, you may eventually get a collar and you'll belong to me." You look at my number in your phone. This isn't a game, this is real. With each text message, each ad, and each visit to my website you're becoming more deeply entangled in my web. 

 

You're afraid. You send me texts, then don't respond to my replies. Do you need this? Do you want to become this? You know that you deserve to at least be punished for wasting my time. You pick up the phone and send me a booking confirmation so you can recieve your punishment. 

 

"I'm not a sissy," you tell yourself, "but I need to accept my punishment then break it off and tell her it's over. I'm not going to end up like that." You know it's a lie. It's already too late for you... 

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