Category Archives: Society

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.

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How to Approach a Woman – Even if She is a Whore

By Kendra Holliday | August 19, 2021

Embrace your erotic side

I know this is going to sound silly coming from a sex worker, but I’ve finally figured out why I find eager, impatient men to be so off-putting.

I get so many men contacting me who want to go from zero to anal in less than an hour.

My whole mission as a sex surrogate is to teach people how to build intimacy and be a good partner, and guess what?

Building intimacy takes time.

I have an extremely reasonable process in place, but all too often I find myself being pushed along like meat on a conveyer belt, ready to be gobbled up, instead of savored.

A man will contact me, and he’ll get super excited when he finds out that I offer all kinds of sexual exploration experiences. He’ll want to do them ALL RIGHT AWAY.

But I’ve learned that I need time to build a relationship with someone, in order to feel comfortable and for things to be authentic. Otherwise, I feel like I’m forced into a performance, and it leaves me feeling yucky afterward, and a relationship that was initiated with such promise and potential becomes tainted, and I have to cut it off in order to protect myself.

Kendra Holliday portraying vanilla. Photo by Stan Strembicki

Here are my biggest turns offs:
Pushiness/eagerness
Impatience
Stinginess
Immaturity
Entitlement

Here’s what turns me ON:
Patience
Maturity
An attitude of gratitude
A generous spirit

I find that the most rewarding encounters I have are with clients who have allowed me to set the pace for building intimacy. I have amazing relationships with clients I’ve been seeing for years. We’ve made so many fantasies come true together!

Here is how to spoil things quickly:
Contact me
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Push boundaries
Disregard feelings and safety

Here is how to create a lasting relationship with me:
Contact me
Be respectful
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment

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Toxic Masculinity from a Sex Worker Perspective

By Kendra Holliday | August 3, 2021

Trust me, I’m a wise witch!

I’m going to preface this with the following disclaimer: I’m a witchy, woo woo, sex worker goddess, and this brain dump is going to sound crazy. I’m fine with that, as I fully embrace my hormonal mood swings and non-traditional way of thinking. I live in a society with lots of self-imposed cages, and my motto is “Think outside the cage.”

So, hear me out, let it all sink in, and let me know what you think!

Toxic masculinity goes hand in hand with white supremacy, and it’s making me sick. It’s making A LOT of us sick.

I’ve been diving deep into history, addiction, psychology, science, and more, and I’ve connected some dots.

Centuries ago, people from Europe set out and explored the world. They invaded many areas and took them over. They brought disease, death, and disruption to the people already living there.

They set up elaborate exports and imports of toxic trade – sugar, tobacco, alcohol, and slavery. They brought oppressive religions and destructive concepts that were deadly and divisive.

They declared that people, plants, animals, and places were all possessions. They put up fences, walls, and demanded territorialism.

They sought to control everything, and lived with a scarcity mindset. They instilled and lived in fear. They were hungry for power imbalance. They felt they were anointed by God, and thus justified in all their actions.

These things represent male energy: fire, cars, guns, alcohol, nicotine, conquering, destruction.

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How I REALLY Feel About Unsolicited Cock Shots

By Kendra Holliday | June 19, 2021

Here we go again. I thought all my friends, lovers and clients knew, but since I just got ANOTHER ONE… 😫

I do NOT like receiving unsolicited cock shots.

I don’t care if I’m a sex worker.

I don’t care if you got carried away.

I don’t care if I’ve played with your cock.

I don’t care if I’ve had it in my mouth.

I don’t care if you are someone I’ve been fucking with for years, or are brand new and exciting.

I don’t care if you are Barack Obama. (Note: My point is, he would NEVER do that. Anthony Weiner, however, WOULD.)

If you send me a cock shot, it’s like a slap in the face, an instant turn off, and an online assault, and I will fine you $50 and demand an apology if you ever want to interact with me again.

It’s all about comfort and context, people.

Wait, no…MEN.

I challenge you to comment if you’ve never sent a cock shot, or wish to publicly apologize for sending a cock shot. Or feel completely justified in sending a cock shot.

So, without further ado…

Wanna know the quickest way NOT to get under my skirt?

Think dealbreaker, hard limit, red flag, turn OFF.

OK, besides wearing ugly footwear or torturing small mammals.

Send me an unsolicited cock shot.

Is this what men imagine their cock shot looks like?

My dick is a GOD!

or this?

My dick is seriously BAD ASS.

or this?

My penis is all-powerful!

Guys. Here is what it really looks like:

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A Woman for Sale

By Kendra Holliday | May 20, 2021

This is a guest post by my friend, mentor, and fellow sex worker, Erika Jones. It was originally published in her delightfully refreshing newsletter. You can visit her website to sign up for that, and more!

Erika Jones, of Ebony Body Works TV

“What made you do this kind of work”?

If I had a round of ammo for how many times I have heard this over the past 25 years, I could overthrow a small country with an army of stiletto wearing hookers.

I once felt like I had to respond with some tired cliché’ like: “It’s empowering” or “I like pleasing men”.

Then a few weeks ago, I was asked that dreaded question once again, and I had what some would call a moment of shear clarity and responded “Because I can“….It was so refreshing to say those words.

Contrary to popular belief, and what the media spews to the public, sex workers are no different than your average woman. They have children, a man, a home, bills, and sometimes a “regular” 9-5. They just so happen to be hookers on the side. And with the American population so quick to judge them, it’s imperative that Americans understand that a person isn’t defined by what they do for a living.

If a woman were a garbage lady, would that make her garbage? If she worked for the sewer company, does that make her shit? In the end, we all prostitute ourselves in some sort of way. Whether you model or dance the ballet, you are still using your body to make a profit. Back in pre-historic times, the men would show off their strengths and abilities to find wives and mates.

The women would come along and accept these men’s sexual requests in exchange for food, protection, companionship, and shelter. And this is where the idea of prostitution began… And they don’t call it the world’s oldest profession for nothing…

I think that most females get wrapped up in the whole label thing, and being called a hooker is the worst thing you can call her. But if you take all the sugar babies, kept women, and trophy wives and put them in one big room next to your top paid hookers, they all start to look the same…

Because they are!

Post Pandemic Playtime

By Kendra Holliday | March 26, 2021

Kendra Holliday, 2021

If you are reading this, CONGRATULATIONS!

You survived the pandemic!

2,757,473 around the world have not, 546,825 being in the United States. I don’t have to be accurate typing out those numbers, as they will continue to go up. We’re not quite out of the woods yet.

But what a time to be alive! We all have spring fever and, after being disrupted and on hold for a year, we’re ready to reconnect, and make things happen.

I’m fortunate to be one of the 12% of Missouri residents fully vaccinated right now, which means I can start seeing select clients in-person again next month.

I’ll start off seeing only one or two people in-person a week, as I ease back into things. I will give priority to the following:

  1. Those who read my Cowboy Ethics post.
  2. Those who read my How to Approach a Woman – Even if She is a Whore post.
  3. Those who follow my protocol. I have a screening system in place because it works.
  4. Those who have already established a relationship history with me.
  5. Those who are fully vaccinated.
  6. Those who pay ahead. When I say “deposits make me horny,” I mean that deposits offer a sense of security, which allows me to relax and better prepare for our time together.

If you contact me and mention the word “dollhouse,” I’ll know that you have read this post. 🙂

I try and help as many people as I can, but that isn’t always possible, due to finances, logistics, safety, rude behavior…make no mistake, I operate on mutual respect. Please don’t come at me sideways and expect good results. Not everyone is a good fit.

Oh, and one more thing – I’m not sure when Sex Positive St Louis will be up and running again – we’ve been pretty dormant. 2020 was our Ten Year Anniversary! And I don’t know when I’ll be hosting the next TBK Play Party, but if you have any venue suggestions, let me know! The first post-pandemic play party should be EPIC!

Let’s party!!!

Why Creative Sex is Better Than Straight Sex

By Kendra Holliday | February 18, 2021

Let me school you on creative sex…

Years ago, I went to a swinger party with an ex. There were six women at the party, and we all had lots of fun. But, to my surprise, when we were driving home, my ex lamented, “I only got to be with four of the women there.”

Huh??

That’s right – he was dissatisfied with only getting to stick his penis in four of the women’s vaginas that night. He was keeping score!

I’ve noticed other times where I’ve played with a man, and we’ve gotten naked, shared pleasure, had oral, but he left disappointed because he didn’t get to do ALL THE THINGS, i.e., stick his penis in my vagina and have intercourse.

I have clients who spend time with me, and instead of basking in female energy and pleasure, they get bummed if they don’t have an encounter that involves them having an 8 inch penis that remains hard for 45 minutes and drilling me bareback in four different positions.

In other words, they feel let down that they aren’t having sex like they see in mainstream porn.

Meanwhile, I’m having amazing, abundant sex with my partner of 12 years that is leaving us both extremely happy and fulfilled.

The Key to Good Sex!

You want to know why?

Because we are having CREATIVE SEX. We aren’t having straight sex!

Straight sex is what you see in mainstream porn. It is male centered. It’s penis focused. It’s vigorous and aggressive. It’s filmed for camera angles, and based around the male orgasm. It’s objectifying. It’s GOAL ORIENTED, which can set the stage for unrealistic expectations and A LOT of anxiety. And anxiety is terrible for arousal!

The women in straight porn are often uncomfortable – from the fake eyelashes and bleached hair and garter belts and heels, to the pussy pounding and loud vocalization and money shot in the eye.

Creative sex, on the other hand, is more about pleasure, skinship, being in the moment. It is about savoring the experience.

Straight men crave intimacy and connection, but they seek it out in a rigid way that can set them up for disappointment and failure. Moreover, it can be off putting or dissatisfying to their partners.

Creative sex is more egalitarian, and allows for more pleasure and orgasms for all parties involved.

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I Met Larry Flynt!

By Kendra Holliday | February 10, 2021

Larry Flynt and me! photo by Mike Estes

Ed Note: This was originally published June 29, 2012. Larry Flynt died today, Feb 10, 2021. What a legend. 🙁

Earlier this year, I was featured in Hustler magazine.

Hustler Hollywood store threw a party to celebrate, which was a lot of fun.

But that was NOTHING compared to what happened this week! Larry Flynt visited St. Louis and I got to meet him!

I asked one of my girlfriends to go with me. “You want to be seen with a hot chick, don’t you?” she commented drily. Well, yeah!!!

With her white power suit and mirror shades, she looked like my bodyguard – a super sexy Charlie’s Angels type bodyguard.

We walked up to the store and were greeted by a bearded man handing out postcards. Upon first glance, the slick marketing material looked like it was made by Hustler, but upon closer inspection, it proved to be anti-porn literature!

Every year millions of men and women become addicted to porn. Millions let their lust control them. ‘Lust’ is having sexual or pornographic thoughts about another person.

In the book of Matthew, Jesus says if you LOOK at a woman with LUST you’ve already committed Adultery in your heart.

In the book of James, the Bible says that if you break only one commandment, you’re guilty of ALL of them. Breaking God’s law is called sin. Sin leads to death…

So clever of them to try and make people feel guilty for coming to an adult toy store.

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Can Women Get Ruined From Too Much Sex?

By Kendra Holliday | January 17, 2021

Dear Kendra,

A recent tweet of yours got me thinking. Someone asked about the number of sex partners and someone answered, “Why does it matter?”

Well, the average guy like myself, ignorant to the female body, thinks men can have sex with a thousand females and have no physical change to the penis, but if a woman has sex with a bunch of partners, her vagina becomes stretched out or damaged in some way.

As I get older and wiser, this seems like a really stupid believe. Can women have sex with many partners without physical change? Could you explain how the female body really works and educate us cavemen?

My reply:

Sexy hipsters

Sexy hipsters

Every body is different, so some women have very tight vaginas to begin with that slowly become looser over time, kids or no kids, sex partners or not.

How many kids you have makes a difference. So can how much you use your vagina. OR it makes no difference! What if she has c-sections, for instance?

What if she fucks guys with HUGE dicks?

What if she’s a porn star? I’ve heard of porn stars doing anal scenes for five years who sustain damage. Then there is Belladonna who takes really good care of her body and exercises muscles most of us aren’t even aware of!

A woman can do Kegel exercises and tighten PC muscles and make things better.

I’ve asked several guys how different pussies compare – guys who have been with total sluts, women who have had NO kids or four kids, and they say it all feels the same. I think that is their honest answer.

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End of 2020 Reflections

By Kendra Holliday | December 25, 2020

Click to enlarge

If there is one word that summarizes this year for me, it would be “disrupted.”

As of March 2020, everything broke apart and turned upside down.

In normal years, I offer consultations and intimacy sessions, host play parties, and am co-leader for Sex Positive St. Louis, a not-for-profit org that was founded in 2010.

I listened to a podcast where they talked about “All That 2020 Has Taken From Us.”

Here’s my list, what’s yours?

Things 2020 Took From Me:

Gather around for a sex-positive storytime!

80% of my income (thank goodness for a few good men who have kept safely in touch this year)

My 20 year old cat – he died of a sudden brain tumor in Feb.

Sex Positive St Louis events – our annual clothing optional spring fling, our naked pool party, Fleshtivus, our 10 year anniversary celebration.

My birthday trip.

Our summer vacation.

My 19 year old cat – she died of mouth cancer last month.

My childhood home – I helped my dad move into an assisted living apartment and sell his home. We got rid of almost everything.

Most of my dad’s brain – his dementia has gotten so much worse the past few weeks.

My mental health – I’ve had a few breakdowns and bad days, but I’m feeling okay right now. Going to revisit my Sanity Plan next week!

The most frustrating thing I’ve had to deal with this year is impatient men who push my boundaries. They contact me, I state my protocol, and they immediately start to push my boundaries, whining about masks, trying to get as much of my time, energy and expertise as they can for as cheap as possible.

It’s a constant cycle of eager acolytes who contact me – I try to teach them how to light the candles, and they want to just rush in and burn down the church. It feels so disrespectful and is exhausting.

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What Happens to Sex When Your Partner is Ill?

By Kendra Holliday | November 11, 2020

Ivanyi, Lovers, 1909

Ivanyi, Lovers, 1909

In the past three weeks, I’ve had three men approach me for a consultation about a problem they’ve been dealing with for longer than I can fathom: their wife is chronically ill, and they haven’t had sex in years. They’ve cared for her, support and love her, would never leave her, but they are frustrated. Drained.  They aren’t getting their needs met. They feel guilty. When I ask if they feel resentful, they immediately say no, but…

What should they do?

What would YOU do?

Are you partnered with someone who is ill?

Are you ill and partnered?

Are you getting your physical and emotional needs met?

Is your partner getting their physical and emotional needs met?

Are you monogamous or polyamorous?

How do you cope?

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Trump: The Biggest Cockblocker of All Time

By Kendra Holliday | August 2, 2020

Masked up and ready

Since March, I’ve been contacted by countless men seeking intimacy.

In order to keep my loved ones safe, I’ve had to change my entire business model. I’ve met with about four clients a week for online talking consultations, which is all well and good, but that’s not what they really want.

They want SKIN TIME. They want hands on intimacy and practice. They want PLAY TIME. They want in-person SEXY TIME.

If I were to have booked as many sessions as I wanted, I could have scheduled five a week, which amounts to 400 sessions.

Instead, I had to be very careful and screen extra vigilantly, and insist on wearing masks, which a lot of people resisted.

I ended up trying seven masked sessions since March.

Three of those sessions felt safe and good. Four of those sessions did not feel safe and good.

I felt much more comfortable with the men who were as conscientious as I am; the men, who, if I had asked to ditch our masks, would have said, “NO WAY.” Those men were doctors. Those men were scientists. These men had a disabled family member. Those men had cowboy ethics. They cared more about other’s health and well-being than their penis and pleasure.

I felt anxious with the men who were cavalier, who rolled their eyes and chuckled when I asked them to wash their hands. They thought the virus was “no big deal.” If I would have suggested taking off masks (and condoms, for that matter!) they would have gladly done so.

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Local and National Mental Health Support

By Kendra Holliday | June 23, 2020

I know this isn’t a sexy topic, but during this pandemic I’ve been getting lots of inquiries from desperately sad people. Some are suicidal.

I’m not a licensed therapist. My specialty is sex, not suicide. But I truly care about your health and happiness, and I’ve struggled with mental health my entire life, and have been suicidal myself.

Please browse this Links page under counseling for St Louis mental health professionals.

In addition, here are other resources:

National:

National Suicide Prevention Hotline

A free, 24-hour hotline available to anyone in suicidal crisis or emotional distress. Your call will be routed to the nearest crisis center to you. 1-800-273-TALK (8255)

National Hopeline Network 

Hopeline provides support with trained counselors through this national hotline to prevent suicide. 1-800-442-HOPE(4673)

Crisis Text Line

Crisis Text Line serves anyone, in any type of crisis, providing access to free, 24/7 support and information via a medium people already use and trust: text. Text, “HOME” to 741741

Trans Lifeline

Trans Lifeline is a grassroots hotline and microgrants 501(c)(3) non-profit organization offering direct emotional and financial support to trans people in crisis – for the trans community, by the trans community. 877-565-8860  https://www.translifeline.org/

Substance Abuse and Mental Health Services Administration

SAMHSA’s National Helpline is a free, confidential, 24/7, 365-day-a-year treatment referral and information service (in English and Spanish) for individuals and families facing mental and/or substance use disorders. 1-800-662-HELP (4357) https://www.samhsa.gov/find-help/national-helpline

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COVID Kendra?

By Kendra Holliday | May 19, 2020

Flirting with the Angel of Death…

Sigh…I would make the most beautiful vector. 💃😚

I’ve been keeping a list of people who have been wanting to share intimate space with me since mid-March, and it’s currently at 40 folks. These are just the ones who have been screened and verified! 😇🤓

Can you imagine if I went ahead and booked all of those sessions? Move over, Typhoid Mary – COVID Kendra would give you a run for your money! (Speaking of money, this is about ~$10,000 of income I’ve missed out on.) 💸

Typhoid Mary was famous for her peach ice cream – mine is over here melting! 🍨😝

It’s been super frustrating getting loads of inquiries from people who are seeking play parties, group sex, erotic encounters. I have to keep telling them now is not the right time to act on such fantasies.

Right now, we need to hunker down with our sexually creative and adventurous fantasies and come up with some future goals – beef up our “Fuck it List” (as opposed to Bucket List). And it pains me when someone who has been in contact with me for months or even years, emails me now, declaring that they are FINALLY ready to move forward with addressing their sexual issue. I’m sorry, but the timing is off.  It’s like being an unpaid DJ taking song requests from people wearing earplugs. And then when I offer them the option of meeting online, they inform me that they lack the funds, the privacy, etc. Stifling and frustrating for everyone involved!

My hands are tied…

I promised everyone I would get in touch with them when I’m ready to start seeing clients in person again, and gosh is that a mind-bending waiting game. The devil is in the details… 👺📝
What are the best resources for me with guidelines on how to keep my clients safe? I guess I need to research CDC guidelines for massage therapists.
For now, I’ll keep blowing you kisses from a safe distance!

You gotta blow hard

“Help Me Get Laid!”

By Kendra Holliday | May 6, 2020

Hello! Do I know you?

The other day, I asked my friends for advice on how to deal with all the men who contact me looking for sex. I told them:

Since I’m so out there as a sex-positive activist and everyone knows I’m in touch with my sexuality, I get a lot of man contacting me requesting female energy/sex. I tell them that is a service I offer. With some of them, they are agreeable to my way of doing things, but others can’t or don’t want to pay for intimacy services, which is totally cool. It means we want different things, and they can go look somewhere else.

But here’s where it gets tricky. Some move on, but some dig in and ask me for a bunch of free dating advice (I offer consults as a service as well), or, even worse, they plead with me to help them find women to have sex with for free. This baffles me – are they asking me how to date? Do they think I have a closet full of sexy women to go to and pull one out and give to them?

Men: How do you find women who want to have sex with you?

Women: Where are you? Why are you hiding? They can’t find you. Are you wanting to have sex with men? Are you picky, or will you get with almost anyone who asks?

I give them a couple quick suggestions and resources, and then usually I just have to stop replying to their messages.

To be clear, some of the men are entitled and lazy, but others have additional challenges such as anxiety, autism, disability, or social awkwardness.

Below, I’m going to share with you my suggestions, as well as advice from my friends. One female friend even wrote a guest post about it – you can read it here.

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I was gonna say Casper but yes this ⬇️ https://t.co/wlKs9eh4X6

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omg she scared the 💩 out of me, ha! That’s what I get for stepping out on her 💃🏼😱😳😝 https://t.co/VCjPKoT37Y

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The movie The Notebook is the worst. Also, I match the movie. 😳🤢😬😝 https://t.co/5eJmOk1lKy

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Surprise ran into my most elusive sibling today at CVS! 🦌😮 I was buying some vitamin D. 😁 https://t.co/rUqEawwtMw