©2018 Hailey Heartless. Vancouver, British Columbia.

September 24, 2018

October 10: Making Love to a Trans Woman at The Art of Loving

Do you have a trans girlfriend? Do you have a crush on a trans woman? Perhaps you're just curious about how intimacy would work with a trans woman. 

Trans women's intimacy is often mystified and influenced b...

August 9, 2018

Image Description: Bright pink glossy lips peek out through a hole in baby pink paper. Credit: Ian Dooley/Unsplash 

I recently received the following message into my DMs on Twitter:

Image Text: I'm a trans woman who is trying to get into sissy play. I've been pretty clos...

July 17, 2018

Hello my beautifuls 

I'm planning a reddit AMA on Saturday at 1pm Vancouver Time to talk about my recent orchiectomy. I'm also happy to answer questions about my life and work in general. When the AMA is finalized I'll post more details here as well as on Twitter . I'll...

March 6, 2018

It seems it's common for women tops to start as bottoms, and I guess that's sort of understandable. Women in the kink community are often just assumed to be submissive, and often we just find our way into the community in a submissive role. As we play more, we start to...

March 6, 2018

A Dom on reddit recently shared a situation they were anxious about. They had a play partner who had a fetish for paying tribute (based on how well the top performed) and this partner wanted a weekend of total power exchange. The play partner also said that they had no...

November 1, 2017

This was my response

The time I ordered a meatball with pickles and mayonnaise because I was craving a hamburger. Kidding! (not about the sub, that actually happened, just about the lame sub pun)

I don't normally talk about play, I strongly believe in confidentiality, bu...

October 30, 2017

She walks into my dungeon. The lights are on high and the walls, traditionally adorned with toys and mirrors, are covered with curtains. The Saint Andrew's Cross still occupies it's space in the center, and the exam table is still in the corner, but the spanking bench...

September 25, 2017

So, you've accepted you're naturally a submissive, and you've finally made the leap onto fetlife. It doesn't matter if you're a man, a woman, or another gender, what matters is that you've made your account and you're going to find your Domme. After browsing and contri...

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...

July 7, 2017

When I started branching out as a sex positive activist, one of the first workshops I took was on polyamory. I didn't know at the time, but the workshop ended up being very heavily focused on how couples could pull out of the driveway of monogamy and enter the streets...

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Upcoming Events: October 2018

September 24, 2018

Forced Fem Belongs to Trans Women

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