Orgasm Count 2021

By Kendra Holliday | January 2, 2022

Let us all pray for a healthy sex life

Here are some of the silly “projects” I’ve done in the past:

Fetish of the Day

Panty of the Week

No Shave May

Shaving My Head

Collecting and Reviewing Sex Toys

Graphing My Orgasm

Nun Striptease (when you click on the link, select “Latest” tab for best results)

Hosting TBK play parties and other specialty events such as Topless Tarot, Crossdresser Tea Party, gang bangs, CFNM, pegging/blow job/fisting/squirting demos…

Sometimes, I look back at my archives and can’t believe I’ve done some of this stuff! Some of it makes me cringe, but most of it makes me feel extremely proud.

In 2021, I counted my orgasms. It wasn’t a contest or a challenge, I was just curious. I’m usually satisfied with one or two orgasms per encounter, whether that’s with others involved, or solo.

Here is the tally:

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No Room at the Inn

By Kendra Holliday | December 16, 2021

A very happy and shiny Kendra Holliday

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. 🙂

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A Few of My Favorite Things

By Kendra Holliday | November 30, 2021

Nuru Mermaid

Nuru Mermaid

Since you asked… here is a list of some of my favorite things:

Cash, of course!

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 kendra@thebeautifulkind.com – 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.

or

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?

Soft blankets, soft tummy

Soft blankets, soft tummy

– 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!

Fruit from heaven

Fruit from heaven

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?

The Casting Couch

By Kendra Holliday | November 13, 2021

Queen Bee, by Hot Octopuss

I have many wonderful clients. One of my favorites is an older gentleman. We’ve been exploring together since 2013!

He’s sweet, considerate, brilliant, generous, respectful, easy going…I love him!

He greatly admires strong, intelligent women – for REAL, he’s not just saying that like so many other men do. His actions match his words.

We usually meet twice a month, alternating between talk and touch sessions. He’s the person I did the Orgasm Experiment with, and he’s a big fan of creative sex.

Usually, our sessions involve me taking on the role of a bossy, demanding woman, such as a stepmother or teacher or nurse. But every once in a while, he tries to get outside his comfort zone and he assumes the power position, such as creepy boss “Mr. Jones.”

Recently, he suggested this roleplay to me:

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Toxic Masculinity from a Sex Worker Perspective

By Kendra Holliday | November 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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Happy Fisting Day!

By Kendra Holliday | October 21, 2021

I caught this exchange on a sex blog the other day:

“Is fisting painful?”

The sex blogger replied:

Two insidious suppositions haunt any discussion of fisting. First, that it will stretch out the vagina to cavern-like dimensions; and second, that it will hurt. Neither is true…

Remove the fist and the vagina does not hang open like the lips of a mouth-breather. It snaps back. Really. Maybe I should post some before and after photos some day?

In the comments, I volunteered to do an explicit photo series, because that’s what occurs to me when I catch wind of something sexually daring, unlike most people who read about it, nod with curiosity, and then go on about their business.

I enlisted my dear friend Rockabilly Girl to do the fisting, and Matthew to take pics.

Get this: I was featured in Hustler magazine earlier this year, and they asked if they could run this photo series. At first I was shocked at the idea, but then I decided it would be pretty fucking cool to rock the fisting in a national hardcore porn mag!

So they made everyone sign releases and submit photo ID’s, including Rockabilly Girl, whose fist is the only thing you see in the pics (until it goes in my vagina).

Then, after weeks of legal paperwork and emails back and forth, Hustler decided against running the pics after all. Too edgy.

But not for me! I think it’s natural, lovely, and intensely beautiful.

So here you go.

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Prostate Mama

By Kendra Holliday | October 17, 2021

I love giving prostate massages.

Setting the stage for prostate massage

I’ve done it many times, on my massage table, and on my bed.

Sometimes, the client requests it; sometimes, I suggest it.

It’s good for your health. It’s intense. It often elicits a different kind of release/orgasm.

For some, it can feel extremely pleasurable; for others, it can be more like a soul reboot.

The client arrives clean, meaning they have prepped for anal play by having an enema or emptying bowels. I always check on them when they show up, asking how they are feeling physically, and if they’re still in the mood/headspace for anal play. If they aren’t, we switch gears. If they are, we assume the position!

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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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Boundaries and Balance

By Kendra Holliday | July 22, 2021

SMILE!

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.

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My Year as a Stripper

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?!

Stripping.

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?

Me circa this era, in the great outdoors and not in a gross strip club

Me circa this era, in the great outdoors and not in a gross strip club

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.

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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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Kendra Holliday Podcast Interviews

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!

Relationship Value Items

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)?

Ah, the bliss of connection!

Loyalty
Stability
Feeling safe
Unconditional acceptance
Being appreciated
Commitment
Honesty
Respect
Reliability
Sharing resources
Acts of service
Trust
Vulnerability
Companionship
Quality time
Emotional intimacy
Open communication
Feeling heard. Do they listen? If they get distracted, do they follow up with what you were saying?
Authenticity
Privacy
Shared interests
Common values
Accommodating
Willingness to compromise
Flexibility
Appreciation
Independence
Alone time
Partner enjoys spending quality time with your loved ones/chosen family
Maintaining friendships
Supporting each other’s personal growth/mission: reading what you write, listening to your music, your podcasts, supporting your continuing ed

Red, white, and blue! We’re doing it for our country!

Physical intimacy
Being desired
Frequent sex
Experimentation/Adventure
Humor
Playfulness
Versatility within sex life
Sex with different people
Challenge
Stimulation
Change

His Favorite Lingerie

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:

Hanging out at home wearing jeans & tank top

Stripped down just a little bit more:

Live

These boy shorts say: life . energy . intelligence

What attire do you find sexiest?

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