By Kendra Holliday | August 23, 2021
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).
By Kendra Holliday | August 19, 2021
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.
Here are my biggest turns offs:
Here’s what turns me ON:
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:
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Disregard feelings and safety
Here is how to create a lasting relationship with me:
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment
By Kendra Holliday | August 3, 2021
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.
By Kendra Holliday | July 22, 2021
Three is my magic number.
I was born 3-23-73.
I’m really good at threesomes. 🙂
I have sacred feminine triangles all over my body – my hairy underarms and pubic hair represents one; my breasts and belly represent another.
I find that my life is best balanced when I’m nurturing these three things:
Professional career – represented by my site Be Open and Honest
Personal life – represented by this blog!
Philanthropic endeavors – represented by Sex Positive St. Louis, my all-volunteer community organization
Sometimes, things get out of whack, and my personal life suffers, or my volunteer efforts lag, but I’ve found that the best way to keep things balanced is to ENFORCE MY BOUNDARIES.
I know my boundaries, but they are always being pushed by other people and forces, and it’s exhausting! They don’t mean to do it, but that’s life as a sex worker whose motto is: NEVER BORED.
Here are some examples of my boundaries:
- I always use condoms with intercourse. I don’t let random men rub their penis on my vulva.
- I don’t receive anal. It’s not an erogenous zone for me. But I’ll gladly give it! 😉
- I do things on my own terms. If someone contacts me and wants to work with me but doesn’t want to follow my guidelines, then I don’t work with them. I have my protocol in place for a reason.
It’s funny, but I find that the more I put out there, the more some people expect. For instance, I post a Panty of the Day pic on Twitter, and I’ll have men send me Direct Messages asking for more free pics.
By Kendra Holliday | July 11, 2021
Disclaimer: I wrote this a long time ago, and it never seemed to fit the vibe of this blog, so I’ve never published it here, or anywhere. It ALMOST made it in BUST magazine, but they chose an essay about male strippers instead.
I was in a very different place 20+ years ago, but since I mentioned it in the post yesterday about Jobs I Have Had, I decided to follow up with this.
Do you know, strippers in 2021 still make the same amount of money I made in 1991?!
I had this gig was when I was 19 (I’m 48 now). I was pretty much trapped in a bad spot – kicked out of my house, no money, no car, dead end job.
I didn’t know what to do. So one day, a girlfriend and I decided to check out the strip clubs on the East Side. I called a place at random, and asked if they hired girls who had no boobs and couldn’t dance. She said sure, gave me directions, and told me to come in for an “interview.”
So I saved up money for a down payment on the cheapest car I could find, and we drove over there.
It was SO frightening entering that place. It was like a haunted house, but it was in the afternoon, and the building sat on a gravel parking lot in Washington Park like an overgrown mobile home. It was called Mainstreet.
Quaking, my friend and I entered. It was really dark, and we had to go up some stairs. There was a bouncer at the door, a 6’6″ black man named Humphrey who directed us to the bartender, who was in charge. She was very tan, busty, and abrupt, and our “interview” consisted of us being taken back to the dressing room, and being told to lift our shirts. I guess she was checking for scars, or a hairy chest or something.
We filled out an application (the whole purpose being to get in writing that you’re 18), and we were hired.
I gave my employer two weeks notice, and soon it was my first day to report to the strip club. I was SOO nervous, because guess what?
I was on my own.
My friend chickened out. (It’s almost unheard of for a woman to just walk into a strip joint out of the blue and get a job there. Women usually wind up there because a friend they party with or relative works there.)
My first day was TERRIFYING. I was paired up with a sweet-n-stupid girl with bleach blond curls and pink lipstick named “Sassy,” who took one look at me and gave me the name “Glamour.” Can you believe that was my stage name?? Isn’t it SO Seven Dwarfs?
She lent me high heels, and for the first time in my life, I got up on a stage and took my clothes off in front of a bunch of strange men 20 years older than me. Can you imagine doing that right now? Can you imagine doing that as a teenager?
We hustled the guys all day, and I went home feeling very dirty and exhausted. And that’s the way I felt for next nine months. I was in my prime and desired by many, but absolutely LOATHED myself.
The strip club I worked at was owned by a nasty man in his 50’s named Tom Venezia, and his 25 yr old son, Milan Venezia. They were SLEAZY all right, and were involved in all kinds of illegal activity, and had loads of money. Milan thought he was hot stuff, so did his dad. They would pick the hardest, bitchiest princess girls and SHARE them, and of course the “chosen ones” thought they were something else, too. They’d run the bar, like the one who hired me.
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.
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?
Guys. Here is what it really looks like:
By Kendra Holliday | June 17, 2021
I LOOOVE podcasts. Do you listen to any? I hear that only 1 in 5 people do. They’re SUCH a wealth of information, community and connection.
Below are podcasts I’ve been featured on – the most recent is at the top.
May 26, 2021: DriveThru HR: Exploring Intimacy, Sex and Work with Kendra Holliday
October 25, 2019: Experience 50: I Apologize with Kendra Holliday
January 14, 2019: About Sex with Angela Skurtu: Sex Positive St Louis with David and Kendra
July 8, 2018: Ethical Society of St. Louis: When You Wish Upon a Star: What We All Truly Desire
August 20, 2017: About Sex with Angela Skurtu: Thorn and her Mother Kendra Holliday – Asexuality, Raising a Child to be Sex Positive – A Teen’s Perspective
August 2, 2017: Family Affairs: Sex-Positive Parenting, featuring Sex Worker Kendra Holliday and her 16 year old daughter!
July 23, 2017: About Sex with Angela Skurtu: Sex Surrogate Kendra Holliday and her partner Matthew discuss Polyamory, Masculinity, and anything Kinky
July 16, 2017: About Sex with Sex Therapist Angela Skurtu: Sex Surrogacy with Kendra Holliday and her partner Matthew
April 25, 2017: 057: BDSM: Shame, Humiliation, & Funnel Cakes
I had so much fun discussing creative sex play and humiliation with host Ben Robbins.
This one followed up an interview we did a month earlier.
March 25, 2017: 054: Escorting, Specialty Fetish and Non-Traditional Sex Therapy
Ah yes, good times!
January 6, 2017: Euphoric Epiphany, Hosted by Victoria
Strangers podcast was by far the most popular one, where I talk about Sex Surrogacy.
April, 2016: Sexistential (this was one of the best interviews and it’s no longer freely available; you have to be a Patreon member.)
Host Lea Thau visited me at my home. It was a nice change having a microphone stuck in my face instead of a penis, LOL!
March 28, 2011: Interview with Sex is Fun, all about my painful coming out process as a sex-positive activist.
October, 2010. Another interview about my coming out, this time with Life on the Swingset, right as it was happening.
October, 2010. This one is all about anal! with Life on the Swingset. I love how Cooper Beckett was celebrating pegging back before it was all the rage!
Those are all the ones I remember. I’ll keep this post updated with any new interviews. I’d love to have my own podcast, but I know how much time and energy it takes.
What are your favorite sex or human interest podcasts? Are there any you’d like to see me featured on?
I like Guys We Fucked, RISK!, Savage Lovecast, The Intimate Lifestyle, HiPPiE WiTCH, and Death, Sex and Money. One I just learned about is The Manwhore Podcast – he recently conducted an interview with an erotic massage sex worker as he received a happy ending! Another one new to me is The Mental Illness Happy Hour – the host often covers sexual shame and secret fantasies. It gets pretty deep. Check out the survey section on his website!
By Kendra Holliday | June 15, 2021
Below is a list of relationship value items. Which ones are important to you? Are you getting your emotional and physical needs met? What about your partner(s)?
Acts of service
Feeling heard. Do they listen? If they get distracted, do they follow up with what you were saying?
Willingness to compromise
Partner enjoys spending quality time with your loved ones/chosen family
Supporting each other’s personal growth/mission: reading what you write, listening to your music, your podcasts, supporting your continuing ed
Versatility within sex life
Sex with different people
By Kendra Holliday | June 3, 2021
My man likes the sexy dresses, fishnet stockings and all that, but what he loves most is the casual, natural look.
Jeans and a tank top, no bra:
Stripped down just a little bit more:
These boy shorts say: life . energy . intelligence
What attire do you find sexiest?
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!
“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!
By Kendra Holliday | May 2, 2021
Years ago, I used to write sex toy reviews all the time, but after a while, it got old, so I stopped doing it.
But now, I have good, NEW reasons to write reviews – I’m now a Tenga affiliate! Tenga is one of my favorite toy companies – I’ve been singing their praises for years, and they keep coming up with new and exciting designs and promotions.
This was a great month to sign up, as it’s May Masturbation Challenge! #doitinmay
This month-long celebration dovetails nicely into my running project of keeping track of how many orgasms I have this year – as of right now, I’ve had 167 so far in 2021. 🙂
(BTW, I personally prefer using the words “self pleasure” and “pleasure tools” for the words “masturbation” and “sex toys.”)
Tenga almost makes me wish I had a penis! But they also have great toys for clits, too! Like this super silky textured, sushi-inspired design, iroha+ TORI. It reminds me of a vibrating tongue!
Being an affiliate has many perks, including getting to try out brand new designs. One that will be available in the US later this year is called the Tenga Aero Cobalt Ring.
Doesn’t it resemble an air freshener?! It’s such a high tech, ingenious design. It comes in two versions – Cobalt and Silver. Cobalt offers more suction, Silver is more spiral sensation:
By Kendra Holliday | April 23, 2021
This week I had one of my yearly photoshoots with one of my favorite people, Stan Strembicki!
We’ve been doing about two shoots a year since 2007 maybe? Sometimes solo, sometimes with friends, sometimes as a group. Mostly in his studio, but sometimes in the woods, in abandoned buildings…
But one thing is for sure – I’m always NAKED.
Many of the photos on this blog are by Stan. He took my Coming Out photos in 2010! This was one of those:
By Kendra Holliday | March 26, 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:
- Those who read my Cowboy Ethics post.
- Those who read my How to Approach a Woman – Even if She is a Whore post.
- Those who follow my protocol. I have a screening system in place because it works.
- Those who have already established a relationship history with me.
- Those who are fully vaccinated.
- 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!
By Kendra Holliday | March 13, 2021
First of all, if it weren’t for the pandemic, this would’ve been a public event! I asked my friend Andy if he’d do a demo in the future, and he said YES!
So stay tuned for that, and in the meantime, read and see LOTS OF PICS showing how one goes about capturing a gorgeous 3D likeness of their genitals!
It all started with me posting on twitter:
Can anyone recommend a good vulva casting kit? Any tips? I don’t want it looking super raggedy and rotty. I can’t believe I’m almost 50 years old and have never had my vulva immortalized in this way, when it has brought me such pleasure and $power$. I’ve been looking up options and think it’s so funny some are called “Adult Vagina Molds” – I definitely DO NOT want a replica of “the muscular tube leading from the external genitals to the cervix of the uterus in women and most female mammals.”
My friend Andy from Shameless Grounds sent me a message:
If you’d like tips/instruction/help with doing a vulva casting, I have a fair bit of practice with casting, and I have the equipment to do a pretty high quality amateur casting (vacuum chamber to remove bubbles from the casting agent, mold release, etc.). I haven’t done a vulva casting before, but I have a pretty good idea of how to go about it to get a nice casting done..
If it comes out nicely, I will bask in the glow of having immortalized a powerful bit of feminine energy.
Isn’t that sweet?! You’ll be interested to know that Andy is quite the crafty, kinky handyman. He builds floggers, human cages, crosses – he even helps friends safely hang their sex swings!
He explained the process to me:
If you’re comfortable, Covid-wise, being in the same room with me for about an hour wearing masks, and being within 6 feet for about 15 minutes, we can do it.
You’ll want a relatively smooth and hairless vulva on the casting day. Pubic hair up higher is fine, as long as it’s not in the “casting zone”. Hair doesn’t “cast”; it gets embedded into the casting medium, and would likely get pulled out when the cast is removed. It also messes up the casting impression.
Shave your vulva 2-3 days ahead to give your skin a chance to recover from any shaving irritation before we slather goop on it.
Rub some coconut oil or similar vulva-safe oil on just prior to casting. It will protect your skin and make the casting come off super easy.
And just so you know what to expect for the actual casting, we’ll have you lift your hips and lower back up on a pillow. You’ll be stuck like that for about 10-15 minutes for an alginate casting.
We’ll mix the alginate with some warm water. I just “glop” that mixture on to your vulva, making sure we don’t have any bubbles in it, and making sure we cover everything about 1/2″ thick in the glop. While it’s still gloppy, I’ll pat some loose cotton fiber on top of it, and then put a layer of plaster bandages over the top of that. The cotton fiber binds the delicate alginate to the sturdy plaster – making the whole thing hold together better than just alginate alone. Then everything sets up for about 5 or 6 minutes, and it’s ready to remove. It takes about 15 minutes from mixing to cleanup.
I’ll take the fresh mold home with me, and make a casting from it. The casting can be either plaster or resin, and it needs to dry overnight. The next day we see how it came out, and do any little touchups that might be needed. And that’s it. You’re casting should be complete and ready to give to you a few days from when we met.
I’ll bring everything needed. I just need access to warm tap water, and a comfy place where you can lie back and elevate your hips for a few minutes. We’ll put a plastic trash bag under you to catch any drips or spills, but other than that, it’s not too messy.
Once the alginate gets mixed, it sets up fast, and I need to get it on you within 3 or 4 minutes. Once I start, my hands will be full of glop.
First, he practiced on a plaster vulva that was already on display in the shop (there are several you can see, made by a local artist). Wouldn’t it make a marvelous night light?
Then he practiced on a real woman – his wife. Just think – when I first posted about this, Andy had never done a vulva cast – now look at him – he’s on a roll!
The morning of our vulva casting, I took a walk, and noticed how ALIVE my pussy felt – I was all tingling and turned on! Clearly, I was eager to indulge my exhibitionist side with a trusted friend.
By Kendra Holliday | March 11, 2021
Lately, I’ve taken to calling sex toys “pleasure tools,” as it seems a more accurate description.
As you probably know, I offer sex-positive consultations, in which I offer feedback and suggestions for a healthier, happier life. Of course all of my oftentimes unconventional advice is take it or leave it, but I always feel pleased when a person actually takes my advice and DOES THE WORK, i.e., reads the books, listens to the podcasts, and procures the pleasure tools I recommend.
One such man is a lumberjack up in New England. We’ve been enjoying monthly online sessions during the pandemic. He’s looked into my mentors Joan Price and Barbara Carrellas, and has even signed up for classes and expanded his pleasure tool collection. Honestly, he’s shared as many resources with me as I have with him. My favorite relationships are the kind where we learn and grow together. (If you aren’t able to book sessions with me, you can always get free ideas from reading this blog or following me on twitter.)
He saw a review of Aneros prostate massagers on here and decided to get one. Not long after that, he upgraded to a vibrating version called Vice 2. He reported such stunning sensations, I asked him to write a guest post review of it. Here it is!
“I first learned of Aneros from Kendra. I had shared with her during one of our online sessions that I sometimes felt a wonderful tingling sensation around my anus as I felt myself leading up to climax. Not very macho sounding, but true all the same. She suggested I read a blog post that her partner had written about the Aneros. So I did and I followed a link to the Aneros website.
(I want to take a moment to say that if you are not hiring Kendra for some online fun and sexy conversation, you are missing out!)
I didn’t buy one right away, as I didn’t think it was right for me – the only times I’ve ever had something up my ass was during a medical procedure or that one time I got a lingam massage. The Tantrica offered to massage my prostate and I said I was willing to give it a try. I didn’t really enjoy it, through no fault on her part; she was great. The lingam massage overall was amazing, just not that anal penetration part. I figured that sort of thing wasn’t for me.
One thing from the Aneros website that did catch my eye was the therapeutic side of their products and since I’m in my mid-fifties and on Flomax (tamsulosin) for my prostate, I kept thinking about it. One thing about Flomax is that as a side effect it can dry up your semen and that, my friends, SUCKS. Not being able to actually ejaculate while still orgasming is very unsatisfying for me. So I decided to purchase one to see if it would help. I ordered the Helix SYN Trident.