Whip Smart

By Kendra Holliday | August 23, 2021

Me playing Cruella de Vil

So, last month, I had a breakdown. I got really mentally and physically ill for a few days. I could barely function – my heart raced, my blood pressure was high, I was sobbing and puking, etc…

This wasn’t my first episode like this – I’ve had a few – due to menopause, hormones, overheating, stress, alcohol abuse, grief, family issues (my dad has dementia), burnout…

This time, I think what caused me to crash and burn was scheduling several intense sessions the week after I got back from vacation.

This is nothing against the lovely men I played with, or the scene topics, but I’ve found that some sessions affect me more than others.

My easy sessions involve surrogate work, TLC, sensual, playful topics.

The more challenging sessions for me these days involve more corporal, kinky, dark fantasies and roleplays. They’re a lot of fun, but they can be very draining, and sometimes it takes me a couple days to recover from the emotional hangover. It didn’t use to be that way – I used to move on quicker. That makes me wonder, is it worth it to me to do these types of sessions? Why do I feel more anxious before some sessions than with others?

I often hear from clients about a Dominatrix they were fond of, but the Domme retired “after a few months.” I wonder why that is? And how do some Dommes make it a decades-long career? Does it depend on their personality? (I’m an INFJ – I feel A LOT).

I decided to read Melissa Febos‘ book Whip Smart, her memoir about being a Dominatrix in NYC for three years. I was shocked and validated by what I read. I highly recommend you check it out.

Pondering my role as a powerful woman

One thing that’s been bothering me, is that men hire us to fulfill their fantasies, claiming they want to be submissive to women, or, that they “want to please us,” but sometimes, the scene devolves into a passive aggressive show of wills.

For example, the man might want to be restrained, but often expect the Domme to wear tight corsets, heels, etc. Yes, classic Domme attire is super hot and sexy, but let’s face it – it’s quite constraining!

When the men ask to worship our bodies, for us to sit on their face, they make out like it’s to give us pleasure, but I think it’s really more of a way for them to enjoy the ultimate feminine energy “surround sound” immersive experience. (Note: Some Dommes offer BDSM only, without sexual activity, whereas other sex workers offer a combination. It depends on what types of services and boundaries each individual offers.)

Sometimes, it feels like they really are siphoning off my energy, which should be okay, since it is renewable, but just like a phone battery, it needs time to recharge. And sometimes, it feels like they really do want to absorb me, even trade skins with me. Many of these men want to be ME when they grow up – or should I say, grow down?

Here’s what I mean by that – this is a quote from Melissa Febos’ book Whip Smart:

“So many sessions were based on a kind of inversion of misogyny, the subjugation of women reenacted by men on themselves. Our clients wanted to be dressed in women’s clothing and raped, molested, infantilized, humiliated, and physically abused. Did this kind of mimicry reinforce or subvert the power of these paradigms?”


“My client lived a kind of sexual samsara…”

Phew! Just reading about some of these scenes was exhausting!

After Melissa Febos, aka “Justine” as she was known in the dungeon, became sober, “work became miserable. I staggered through the sessions, wondering how it had ever seemed easy. The closeness of their bodies was excruciating. It was another kind of feeling skinned…If their powerlessness and shame were a bog that I had previously traversed untouched, I was now slipping. I could smell it – the brackish stink under me – on my hands and feet, in my hair when I woke up in the morning…”


On topping from the bottom, she wrote: “Clients who topped from the bottom specified little before the session began. They pretended to be a different kind of client. ‘Schoolmistress,’ they’d request, as if trusting that I would know all it entailed, which I did, just not down to the ordered of every last detail and inflection. I knew what ‘schoolmistress’ meant and what kind of makeup and stockings and pain they required. But still I would spend an hour having every movement of my tyrannical role dictated to me. It was maddening, like being asked to run sprints in a straitjacket. I knew what to do, I was good at knowing what to do, but they still whispered the answers to me…”

and then she went on to say:

“We were all topping from the bottom, it seemed. Both my clients and coworkers were designing their own humiliation. Freud said that there is no sadism without masochism. If there was ever a sadistic masochist, my client Jack was one. He was one of those clients who preyed on new hires – they were looking for victims, not masters. I met many men whose real pleasure seemed found in demanding torture methods more humiliating for their Domme than for them. Is it worse to be fisted as you fantasize, or to shove your arm up a strange man’s ass for money? To have your yarmulke shat in or have to shit in a yarmulke while a stranger watches?”


“Imagine reenacting the most painful traumas of people’s lives all day, becoming, one hour at a time, the embodiment of their obsessions, their sexual fixations; it would suck the life out of you…”

“Many sessions had started to feel like surgery without adequate anesthesia…”

So, yeah, phew. I’m not alone.

I’m trying to figure out what types of sessions I want to do, and who I should share intimate space with, for the sake of my mental and physical health. Or, how do I strengthen my energetic boundaries? Should I try and build a thicker skin? I’m not sure I could, even if I wanted to. I like being sensitive and caring and present. I feel like I’m doing this work for the right reasons. I think it can be very cathartic and healing. But at what cost? Is there a different way to approach this?

Hmm… lots to think about. Not to mention lots of emails and inquiries to reply to. Thank you so much for your patience and understanding as I sort this all out.

I love you.

Cruella back view


Matthew 2021-08-23 15:19:53

I love you, too.


Mike j 2021-08-23 23:35:14

I hear you Kendra. If you get uneasy before a certain type of session, maybe it’s time to rethink doing those sessions? I feel that you should get some enjoyment from what you do. If it becomes all work and no play for certain sessions, then maybe it’s time you only do the ones that don’t take so much out of you and are no longer any enjoyment to you. Maybe that sounds strange, but if I was asking for something from you that you no longer liked, I’d want you to tell me NO. To me, part of the enjoyment is knowing and feeling that you enjoyed it as well. Otherwise I’m not benefitting from your female energy in the give and take. “Turn about is fair play.” You’re the best, keep up the articles.


    Kendra Holliday 2021-08-24 00:36:58

    Thank you so much, Mike! I agree that spending time together should be mutually enjoyable/beneficial for all involved. 🙂


    Paul 2021-09-15 11:20:34

    I second what Mike J. wrote on August 23rd.


David Wraith 2021-08-24 03:32:13

I love you, too.


Sarina 2021-08-24 06:44:04

Well written. I love you!


Foxtail 2021-09-04 10:21:20

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Foxtail is an online community for the sex-positive. We serve the BDSM, Kink, and Fetish communities, but everyone is welcome to join our open, pro-sexploration community. We believe everyone is kinky. https://foxtailapp.com


Hector 2021-10-07 10:28:16

I got a breakdown recently. I watched a video on youtube that convinced me there is no God. Ever since, I’m depressed, because now I know that there is nothing after death.

I used to be an atheist in the past too (see my life story in my comment on the Life Milestones post), but, back then, I wasn’t that depressed about it. Now I’m disappointed, because I had really believed that there was a better place after death only to find out that this is not the case.


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