TBK through a GPT filter
By Kendra Holliday | May 13, 2023
Category Archives: Random Bullshit
By Kendra Holliday | May 13, 2023
My client typed this into ChatGPT about me: “Compose a poem about a great 50-year-old woman who sees clients in her own home.”
A woman of fifty, wise and bold,
With stories to tell and hearts to hold,
She welcomes all into her home,
Where comfort and kindness are freely shown.
Her clients come with weary hearts,
Seeking solace from life’s many parts,
And there she sits with gentle grace,
Listening with a warm embrace.
Her words are wise, her touch is kind,
A healing balm for troubled minds,
And when they leave, they feel renewed,
Their spirits lifted, their hearts imbued.
For many years she’s lived this way,
Serving others day by day,
And though the years have come and gone,
Her spirit shines, a radiant dawn.
So here’s to this great woman we praise,
Whose kindness touches many in countless ways,
May her home always be a haven of peace,
Where hearts are healed and troubles cease.
By Kendra Holliday | May 9, 2023
I have so many great things to share with you, but I’ve been so busy!
To make up for it, here is a pic my friend took of me in 2008 at a fun photo shoot (NSFW):
By Kendra Holliday | April 11, 2023
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’re forever 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:
By Kendra Holliday | February 28, 2023
I’m 50 years old! Here is my life trajectory so far:
1973: I’m born in North Dakota. Brrrr!
1974: My family moves to Dallas, Texas.
1975: Who the hell knows.
1976: My brother is born.
1977: Um, Elvis dies?
1978: My sister is born. My brother throws up. I remember my first dream; I’m kidnapped by Captain Hook and held hostage with Raggedy Ann and Andy. He cuts off my foot and it looks like SpaghettiOs.
1979: My family moves to St. Louis.
1980: My baby brother is born, and dies two days later. My mom tries to kill herself several times, and when that fails, she burns his name into the back of her hand with a soldering iron. She is never the same again. A very dark time.
1981: Life still sucks. My mom is a complete wreck.
1982: My brother is born. My grandmother dies.
1983: I get molested by an older, adopted brother. It SUCKS. I get sent to therapy, and I don’t know why. I think I’m being punished. I am a victim.
1984: I have my first lesbian encounter. It’s hot and naughty. I’m 11.
1985: My baby sister is born. I drop her on her head, but don’t kill her. Skeptical about god’s involvement, I become an atheist.
1986: I hit puberty and middle school, and lose all my artistic talent and confidence. My family is poor white trash, and I am branded a zitty nerd. It sucks.
1987: My mom keeps getting crazier and crazier. It makes me crazy, and I attempt suicide. I spend time in three different mental hospitals. I lose my virginity to a 24 year old creep with a mustache because he keeps badgering me and I finally give in. It sucks.
1988: My moms tries to kill herself again. I put pressure on her slashed, gaping arms as my dad calls the ambulance. She gets hospitalized a lot, and OD’s, and gets shock treatment. I fuck around and feel very confused. It sucks.
By Kendra Holliday | October 6, 2022
You know how they talk about baggage, being in the closet, etc.?
Everyone has baggage – daddy issues, mommy issues, family pain, abandonment issues, trust issues, inexperienced issues, break up trauma, secrets, shame, guilt, neglect, abuse, loss, betrayal, injury, fear, rejection…
I like to pretend our head is an attic, and our brain is an old fashioned trunk, crammed full of stuff we’ve collected from our travels.
Space is really tight, and the stuff is jammed in there.
So, I propose this exercise to my clients.
Find the key that opens the trunk.
Open that trunk up.
Now, take ALL the stuff out of it – toss it around the room.
Examine each article – is it a piece of clothing? Is it a toy? Is it wrinkled? Is it moldy? Does it still fit? Do you want to keep it?
Address and assess each item. Acknowledge why it’s in your trunk, and decide if it’s something you want to hang on to.
By Kendra Holliday | August 17, 2022
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.
Aug 16, 2022: Luvbites by Dr Tara: #47 The Truth About Sex Surrogate with Kendra Holliday
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 | August 8, 2022
Here’s how to get over your body image issues:
1. Do a nude photo session
2. Get naked in front of other people
Let me explain.
It’s been almost a year since my hysterectomy surgery. I’m all better, but I’ve noticed my body shifting and changing. I have scars on my tummy now, and fat has gathered around my middle. Sometimes I sit around and feel gross about it. I feel like my clothes are tight. I try eating better. I try being more active.
Last Saturday, I had two events on my calendar: a nude photoshoot with a girlfriend and photographer friend of mine, and a clothing optional pool party. Ugh, being naked around other people was the LAST thing I wanted to do. I yearned to hide under my covers in a comfy nightie instead, but I’m not one to flake out on people just because I’m not feeling it. I tend to push myself to follow through with things I’ve committed to, because it usually works out for the best.
At the photoshoot, I shared my body image concerns with Bianca and Stan. Bianca looked so beautiful and graceful. Stan assured me that I still looked mighty fine and not that much different from when he first started photographing me five years ago. I started to relax, and walked around the studio naked as if it was the most natural thing in the world, because it WAS.
By Kendra Holliday | August 3, 2022
Hey, everyone! Do you miss me?
I made a quick video letting you know what I’ve been doing this summer – unfortunately, it hasn’t been YOU. I’ve been getting screwed in a very different way. 🙂
By Kendra Holliday | April 9, 2022
I offer sex and relationship consulting, and I’m happy to say that I’ve been getting more women, LGBT folks, and couples these days. Historically, most of the people who have sought me out for my unique services have been men who crave female energy.
The Top 5 reasons why people contact me are, in this order:
1. He’s a married man in his 50’s or 60’s whose wife is not interested in sex (mismatched libido)
2. He/she/they have some sort of sexual issue they want to work through, such as inexperience, adult virginity, anxiety, trauma, disabilities, or orgasm/genital problems (Erectile Dysfunction is a common complaint – it can get complex when you heap social conditioning and anxiety on top of the natural aging process.)
3. He/she/they are interested in branching out sexually, either because they are in transition, in between relationships, single/divorced/widowed, not getting laid, or curious about alternative lifestyle options (non-monogamy, kink/BDSM, sex work, etc.)
4. He has a fetish and is ashamed/seeking understanding and validation (“Am I normal?!”) or an outlet
5. They want to meet me, and possibly rub me for good luck
My goal is to offer tools, connections, and non-traditional options so that the people seeking me out can reach their goal of becoming happier and healthier. My approach is unconventional, and I get referrals from licensed sex therapists. I’m pretty well connected and have a strong network. Sex is my specialty, which ties into work, family, personal – everything!
Here is a list of resources I most often recommend to my clients:
By Kendra Holliday | March 24, 2022
Just a quick update letting you know I’m feeling better. I’ll see clients in April, but I’ll be taking it slow and limiting interactions to talking or online appointments only, for now.
My new therapist told me she received these messages while meditating before our first session:
Amen to that!
By Kendra Holliday | December 16, 2021
Confession: My email inbox stocking is stuffed full of inquiries.
Right now, I have about 65 people waiting to hear from me, dating back two months. 🙁 I reply to as many as sweet souls as I can every day, in between sessions and other duties and obligations. (BTW: If you’re waiting for an email from me, check your spam folder. My domain name is blacklisted due to my web host allowing adult content.)
Ideally, I’d like to get back to people within 48 hours, but I’m just one person, and I often get sucked into my menopause mood swings and my dad’s illness – he has mid-stage dementia and I’m his primary care partner. I’ve learned that it is extremely draining to be someone’s quality-of-life support, someone’s seeing eye brain, someone’s backup human being. Even though he lives in assisted living, he depends on me for just about everything.
(As an aside, I’m astonished that I used to have FIVE creatures dependent on me – both my sick parents, my two old cats, and a daughter. All that is left is my dad. I swore to my mother on her death bed that I would take care of him, and I’ve assured him that I will be there for him, for as long as he needs me.)
So all this is to say, I try my best to help others in between my mental health issues and family duties. I’m eager to help people who understand and respect my process. 🙂
By Kendra Holliday | November 30, 2021
Since you asked… here is a list of some of my favorite things:
Wouldn’t it be great if the gas, water and electric companies offered gift certificates? What would be more loving than gifting someone with a hot bath, a home cooked meal, or cooling down/heating up?
Amazon gc – send gift certificates to firstname.lastname@example.org – I looooove books so much! And they sell pretty much everything else.
Whole Foods gc – or Trader Joe’s, Global Foods, Dierberg’s, Schnucks local grocery stores. I don’t eat factory farm mammals or birds, but I do eat veggies, fruit, local, seafood….I love ethnic food like sushi, Indian, Vietnamese, Ethiopian
A donation to
Planned Parenthood – because I believe in accessible health care.
Worldwide Fistula Fund – The Worldwide Fistula Fund is an incubator, funder, and promoter of innovative solutions to improve global women’s reproductive health.
Etsy gc – support artists!
Target gc – I’m a sucker
Flowers – I like when flowers last more like a week as opposed to three days, so the hardier ones are better, though I do like roses and fleeting exotic flowers like orchids. My favorite color rose is the peachy one with blush tones. I don’t like pink as much and I can’t stand the smell of cloying lilies, too funeral home. I keep my flowers in my dining room, which has green walls and lots of colorful jewel tones. Daisies, carnations, sunflowers are great. Did I mention I like colorful?
– I looove soft clothes and blankets!
Shameless Grounds gc – one of my favorite places in St Louis!
Godiva milk chocolate and truffle assortments
DeBrand is even finer, but is based in Fort Wayne IN and worth a goddamn road trip!
Merb’s milk chocolate covered strawberries is local and scrumptious
Soaprocks – these are so cool!
Demeter – they sell so many fun scents, some of my favs are New Leaf, Firefly, Grapefruit Tea, Sushi, Silvery Pekoe, New Zealand, Pipe Tobacco, Leather…
Black Phoenix Alchemy Lab – just look at this website!! I have a scent called Bewitched…
Massage – my baby sis is my massage therapist, she is excellent! You can sponsor a massage for me, or book one for yourself! She’s located in South City. If I know you in real life, I’m happy to refer you.
Victoria’s Secret – I tend to wear L, depending on the style and brand, 36B. My body is average (5′ 4″, 140 lbs) but my mind is extraordinary! I don’t like thongs or g-strings. I prefer timeless and vintage looks over trendy – black, bright colors, jewel tones
I like coffee, tea, and Kombucha.
I’m into oddities, whimsies, cute things, little things, toys…
How about you? What are some of your favorite things?
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.
Is this what men imagine their cock shot looks like?
Guys. Here is what it really looks like:
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:
See the Arch behind me? 😍 https://t.co/rzqNIczrEB
Covered myself (even my hair!) with Rhassoul clay. My skin feels as velvety as a hairless cat! 😮😻 https://t.co/jUvGvmiECN
Go here if you want to buy my dad’s stuff - dropped off a big box of antique radios, red model cars, etc. It pained… https://t.co/GOVfhx8rzt