Playing the Virgin

By Kendra Holliday | July 2, 2016

Guess who is the opposite of a virgin?


Guess who loves the land of make believe?

Yes, Mister Rogers. But also,


And Matthew is my magical play partner. I’ve been with men in the past who were uncomfortable just having phone sex, but luckily for me, this man is down to roleplay an entire evening.

This vintage sheer gown inspired me, and away we went into fantasy land!

You, too, can be a sacred prostitute goddess!

You, too, can be a young virgin with the right imagination!

I was housesitting at a beautiful Victorian home, so it was the perfect setting for our fantasy.

We came up with it together – I was a 22 yr old sheltered, homeschooled girl named Katie. He was 36, and I had met him a few years ago at some homeschooling conference where he gave a presentation for grad school. I ran into him at some small town festival that day, and since my parents were out of town on a church trip, I invited him to come over that evening to hang out.

I had a crush on him and was hoping to make out, but had never done anything beyond first base. So I put on the costume, and he left the house, waited a moment, and then knocked on the front door.

From that moment on, he was the older, experienced man, and I was the shy girl who had no idea what she was getting herself into…


The Sex Spectrum

By Kendra Holliday | June 26, 2016

Kendra Holliday portraying vanilla. Photo by Stan Strembicki

Kendra Holliday portraying vanilla. Photo by Stan Strembicki

I’ve come up with the following Sex Spectrum – do you agree with it? Where do you fall? Where do(es) your partner(s) fall?

Repressed – thinks sex is distasteful, doesn’t recognize any fetishes or fantasies, thinks genitals are ugly, doesn’t masturbate, is uncomfortable with erogenous zones, could easily do without intimacy or sex, is pretty much offended by everything

Vanilla – holding, cuddling, standard sex positions, passionate lovemaking, oral, watching porn, monogamy, mutual masturbation, traditional gender roles, basic sex toys, sex in the bedroom/kitchen/basement work bench/backyard/hotel

Kinky – anal play (male or female), bondage using silk ties and scarves, teacher/secretary/cop fantasy roleplaying, exploring bisexuality, watching hardcore porn, taking pics/filming, female ejaculation, threesomes/foursomes/orgies, advanced sex toys, cross dressing, pegging, sex in a restaurant/elevator/public place, exploring basic fetishes (foot, hair, latex, lingerie, etc.)

Kendra Holliday portraying Perverted

Kendra Holliday portraying Perverted

Perverted – face slapping, rape and incest fantasy roleplaying, gang bangs, bondage involving rope, facefucking, watersports, forced bi/cuckolding/chastity, humiliation and objectification, public sex (with an audience), fisting, double penetration, pegging, crazy sex toys (ball gags, big dongs, strapons), sex in church/graveyard, exploring more unusual fetishes (unwashed, period, amputees, etc.)

Fucked Up – edgeplay (bukkake, bloodplay, bladeplay, gunplay, breathplay, needleplay, electro, caging, necrophilia), gimp masks, body bags, CBT (cock n ball torture), masturbating in a bible, mutilation, sex in a morgue, sex with a real student/relative/prisoner, exploring extreme fetishes (shit, bestiality, vomit, pedophilia)

Does this look about right? For instance, do you think anal falls under Vanilla or Kinky? I first wrote this six years ago, and now that I’ve revisited it, I’ve moved a lot of activities up a notch. For instance, three years ago I considered gang bangs “Fucked Up.” Now, I view them as “Perverted.”

Also, I should state for the record that I don’t think any of these terms are derogative per se. It’s when you start harming yourself or others where I start to draw the line. And basically, the more taboo something is in our society, the more Perverted/Fucked Up it is. And the taboo twist is what makes it so hot! (For further reading, I suggest the book Arousal: The Secret Logic of Sexual Fantasies.)

Personally, I consider myself mostly Kinky, moderately Perverted, with a dash of Fucked Up. And of course I LOVE me some Vanilla! How about you? I’d prefer if most people fell somewhere between Vanilla and Perverted.

The Story Behind My K Necklace

By Kendra Holliday | June 19, 2016

You may have noticed that I always wear a signature piece – my K necklace.

My signature piece K pendant

My signature piece K pendant

I know several people who wear signature pieces – my mentor Barbara Carrellas wears a dragonfly, my Tantra colleague Shaft wears a unicorn, and sex educator Mollena wears her slave collar.

I never take it off, even when I’m wearing other necklaces. The reason why is because it is like my wedding ring, or my BDSM collar.

My partner Matthew gifted it to me back in 2009 (we’ve been together since 2008). It started out as a joke.  Years ago, when we started exploring BDSM, we discovered a lot of comical Dom profiles on FetLife, so we decided to create a parody account featuring a Core Dominant named KAPSLOK. (If you’re a member of FetLife, you can see KAPSLOK’s profile here.) He’s SO Dom, not only does he capitalize his name, but he just keeps the CAPS LOCK key on for EVERYTHING.

“KAPSLOK” “collared” me with a little plastic K that came from a gumball machine. I wore that for a while, until it broke.

You may recall the time I left my travel mug at Matthew’s house, and what he did with it (he filled it with piss!) Well, a couple months later, I left it there again. Ohh nooo, what was he going to put in it this time – shit??

When he handed the mug to me, I cringed, but he had a tender demeanor, which threw me off.

“Open it,” he suggested softly.

Tentatively, I unscrewed the lid, and discovered treasure nestled in tissue paper inside.


Love Like an Ocean: Diving Deep into Polyamory

By Kendra Holliday | June 19, 2016

Like an ocean, love can be
expansive and fluid

Ed Note: This article was orginally published in July 2011 on BlogHer.

My partner and I have the perfect relationship. For us, anyway. We’ve been together for eight years. We’re not married, but are in a long-term relationship. We do not live together, preferring to keep our households, finances, and families separate. Autonomy suits us well.

To top it all off, we are polyamorous; meaning, our relationship is open, allowing us to experience intimate relationships with other people, such as dating, loving, and exploring sexually. Sometimes we do it together; other times, separately.

We don’t fight. We have amazing chemistry and enjoy an incredibly satisfying sex life. We can’t get enough of each other. Our relationship is based on mutual worship and respect, and our number one rule when it comes to dating other people is they need to respect both of us.

Before I knew of polyamory, I thought I was defective and unfit to be in a relationship. After years of disappointing my partners, a series of men who enjoyed playing with the girlfriends I brought home, but freaked at the mere mention of another “sausage in the room,” I resigned myself to remaining single.

Then I met Matthew, who was recently divorced from his wife of ten years. What started out as a happy, traditional monogamous union with Matthew left his wife stifled and miserable. Determined not to repeat those same mistakes again, he took a leap and partnered with me, a renegade female who was in charge of her sexuality and knew what she wanted.

Honoring my atypical outlook on life, Matthew told me he would not hold me to a standard he was not willing to hold himself. So here we are four years later: a polyamorous couple in a sea of monogamy.

Our nation is one of serial monogamy. Polyamory applies the same concept of loving more than one person in a lifetime, the only difference being that these relationships overlap in the case of polyamory, because life is too short.


The Father, The Son, and The Wholly Man

By Matthew | June 18, 2016

“Fatherhood” by Viktor Mikhaylovich Vasnetsov

Ed Note: This is a guest post by my partner, Matthew. He is the father of two children.

A couple of weeks ago, I started hearing the yearly buzz of “Father’s Day” gifts, salutations and tributes.  I started thinking a bit more in depth on the subject of Fatherhood and what it means to me.

Being a Father is synonymous to me with being a man. I hear so many people speak of “men” they know or have connections with and then start divulging details about these people.

I know women who demand flowers from their husbands as a way of apologizing for an act of relationship treason.

I know women who are dating “men” right now, but speak of nothing but their shortcomings.

I know of “men” whose wives have gotten up and walked away from them while they were eating her pussy.

I know of “men” who don’t make an effort to spend time with their children.

I know of “men” who can’t separate business from pleasure and vice versa.

I know of “men” who are so weak themselves, that they show their “strength” by preying on the eager and ignorant.

I know women who have settled for a “man”.

I know of “men” who live in their mother’s basement.

I know of “men” who can’t dress themselves.

I am sure you know plenty of “men” like this as well.

If a man has children, they are his number one priority.


Yoni Eggs

By Kendra Holliday | June 17, 2016

Click on this pic to view eggs actual size

Click on this pic to view eggs actual size

I found out about yoni eggs by happenstance at a party, when I met a vivacious woman named Dailia. A while back, Dailia had hosted an event featuring a woman from Harlem named Makeda Voletta, aka Queen Lioness. Makeda leads workshops all over the country, featuring topics such as sensual strength training and sacred yoni eggs.

Dailia was hopping around the kitchen bragging about the yoni egg she was wearing.

I looked for an amulet or something, but she laughed.

“You can’t SEE her. She’s inside me.”

OH. DUH. Yoni = female genital region – vulva, clitoris, vagina, etc.

“So what is its purpose?” I asked.

She gushed, “She helps me stay grounded, empowered, tight, toned, stimulated, CONNECTED.”

My eyes widened. I had to find out more.

Read Makeda’s Yoni Egg Basics overview.



By Kendra Holliday | June 17, 2016

I’ve had my yoni eggs for almost three years now. I’ve had them since before my hysterectomy.

I’ve futzed around with them off and on over the months, not really committing to them, just experimenting.

(Before you read any further, make sure you read my post yesterday all about yoni eggs so you know what the hell I’m talking about.)

It was a dark and stormy night...

It was a dark and stormy night…

One night, I had an intense phone conversation with my partner Matthew. Hectic life was getting in the way of our relationship and we weren’t feeling connected. The talk left me feeling agitated and upset. Exhausted, I went to sleep feeling like a smelly, wrung out dishrag.

At 3:40, I woke to great thunder and lightning. The tumultuous storm rattled the windows. I fretted and tried relaxing.

I drank a glass of wine.

I stuck my tiger’s eye yoni egg inside me – I wanted something inside. It was soo cold going in.

I frantically masturbated. When I came, I screamed. Then I cried hard, and fell back asleep. I had weird dreams, but don’t really remember them.

I woke to the alarm feeling dreary and drab, not refreshed.

My body clenched the egg tight, it didn’t want to let it go. I had to push it out, and when I did, it was really hot, and some ejaculate came with it.

More tears – this time from my pussy. More release.


Waking a Sleeping Bear

By Kendra Holliday | June 9, 2016

Time to cool down...

Time to cool down…

It’s 7am. I slip into his house.

Matthew has a note waiting for me at the door, along with an empty glass:


I strip. I fill his glass, and enter the dark, cool cave that is his bedroom.

I whisper, “Good morning, My Bear King,” and hand him the glass.

He groans, takes a long pull off the water, then hands it back to me. I set it down, and though he’s still drowsy, as if out of instinct he pulls me up by the hips to straddle his face.

And then he eats.

He licks, kisses, nibbles, all the while sounding like a bear quietly raiding a campground…



His big paws roam up my soft body, catching breasts and curves. Every once in a while he clamps down with his strong fingers like a cobra, injecting poison into the nerves in the small of my back.

My thighs press down on his ears. I tremble and sway.

I cum on his face, and then kiss his well-used and pungent mouth.

He pushes me down and says, “Rub your pussy juices on it.”

I rub up and down on his hard cock – I SO want it to slip inside me, but I avoid the head, just coating the shaft in my juices…

I slither down his wide and hairy torso and suck it hungrily, and as he cums, he seizes me and growls, “SLUT…FUCKING SLUT….”


A Most Interesting Plane Ride

By Kendra Holliday | June 9, 2016

As I prepare for my flight to NYC for Tantra training, I was reminded of one of the most interesting plane rides I’ve ever had – and keep in mind I’m a member of the Mile High Club, so that’s saying something.

Going places!

Going places!

I was flying home from Los Angeles to St. Louis, and a pretty young woman sat down next to me.

She noticed my book and asked, “Excuse me, but what are you reading?”

I told her it was about werewolf prostitutes. I could tell this vivacious minx thought I was a regular mom, so that perked her right up, and gave her a sign that I might be cool.

Turns out she was a 24 yr old stripper from LA on her way to visit one of her sugar daddies in St. Louis, a Porsche-driving, 30 something in the Central West End.

She drank three vodkas on the plane and opened up to me about all the coke parties, working as a receptionist at an escort service, her great love of weed, fucking her roommate/best friend’s boyfriend (“He started it!”), and all the wild parties she attended in Hollywood Hills. She had a thing for dark complected men, and cheerfully ranked her top 10 lovers for me.

As she twirled her tousled brown hair and fiddled with her Tiffany necklace, she recited with rolling eyes, a wicked grin, and shrugging shoulders, “The guy I’m seeing in St. Louis is #3. Marco is #2, he’s the best in bed EVER, and Miguel is #1, he keeps breaking my heart, but I hang up on his ass and that slays him… Dylan is #5, he drives a Hummer. I had my first threesome with oh, what’s his name, well he’s #7 anyway…”

HA! So I was sitting next to a witch, one of those women who dances with the devil in the pale moonlight, an “It” girl, a seductress. Heck, she got up to use the bathroom and a guy sitting on the plane took one look at her and asked for her phone number!


My Body Modifications

By Kendra Holliday | June 4, 2016

Me in 3rd grade

Me in 3rd grade

This is a picture of me from the 3rd grade. Looking at it, it’s hard to believe I was molested – I mean, wouldn’t those ginormous nerd goggles be repellent enough, not to mention the shitty haircut and goofy fashion?

Then again, my opportunistic molester was pretty homely too, and wasn’t very picky. I daresay he had bad taste in children.

But this ugly child grew up to be a gorgeous goddess. Here are some steps I took in my maturity makeover:

Braces – My parents could only afford braces for one of their five kids, so they chose my sister. That means I made it to adulthood with one of my front teeth jutting out. In grade school, kids would come up to me all the time and inform me, “You have a crooked tooth.” LIKE I DIDN’T KNOW. I was self-conscious about smiling, so I scowled a lot.

Finally, when I was married and DINK (double income, no kids), I took the plunge and got Invisalign braces. I’M SO GLAD I DID IT. It was worth every penny (how many pennies are in $4000? oh never mind). Now I wear a retainer at night whenever I feel like it, which is about half the time. I’ve only broken it once. Flossing is so much easier.

Heart zapped – In 2000 I birthed my daughter vaginally – hooray! I didn’t want an epidural or a c-section, but I sure did freak out and request the epidural as soon as my labor pains kicked in for real.

My doctor took it upon herself to give me an episiotomy (a surgical cut in the muscular area between the vagina and the anus), which took a long time to heal. But further north, the pregnancy took other tolls on my body – my heart.

It had trouble keeping up with the extra blood flow and work involved with carrying another person around inside me for months, so it started to misfire. I developed SVT – Supraventricular tachycardia. My heart would sometimes race 300 beats a minute, which was inconvenient and scary. The solution was a procedure where they snake a laser up through your groin to your heart and zap the naughty part and kill it. So my heart has a scar.

The procedure cured my condition, but that zap also signaled the end of my marriage. I woke up from the procedure and everything changed in my life. My heart was fixed and broken, all at once.


Why Whores Are My Heroes, by Annie Sprinkle

By Kendra Holliday | June 3, 2016

One of my favorite goddess sheroes, Annie Sprinkle, posted about why whores are her heroes on facebook.

A few hours later, not only was the post deleted, but she was kicked off facebook for three days for celebrating the sacred beauty of sex work!

Ah well, you can do a google search for images of her and enjoy her words below.

Have a lovely International Whores Day everyone!


Whores have good senses of humor.
Whores challenge sexual mores.
Whores are playful.
Whores are tough.
Whores have careers based on giving pleasure.
Whores are creative.
Whores are adventurous and dare to live dangerously.
Whores teach people how to be better lovers.
Whores are multi-cultured and multi-gendered.
Whores give excellent advice and help people with their personal problems.
Whores have fun.
Whores wear exciting clothes.
Whores have patience and tolerance for people that other people could never manage to put up with.
Whores make lonely people less lonely.
Whores are independent.
Whores teach people how to have safer sex.
Whores are a tradition.
Whores are hot and hip.
Whores are free spirits.
Whores relieve millions of people of unwanted stress and tension.
Whores heal.
Whores endure in the face of fierce prejudice.
Whores make good money.
Whores always have a job.
Whores are sexy and erotic.
Whores have special talents other people just don’t have. Not everyone has what it takes to be a whore.
Whores are interesting people with lots of exciting life stories.
Whores get laid a lot.
Whores help people explore their sexual desires.
Whores explore their own sexual desires.
Whores are not afraid of sex.
Whores hustle.
Whores sparkle.
Whores are entertaining.
Whores have the guts to wear very big wigs.
Whores are not ashamed to be naked.
Whores help people.
Whores make their own hours.
Whores are rebelling against the absurd, patriarchal, sex-negative laws against their profession and are fighting for the legal right to receive financial compensation for their valuable work.

Do you have what it takes to be a whore?

Can Women Get Ruined From Too Much Sex?

By Kendra Holliday | May 19, 2016

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.


Want a Tantra Goddess in the Midwest?

By Kendra Holliday | May 11, 2016

Urban Tantra by Barbara Carrellas

Urban Tantra by Barbara Carrellas

For years, men, women, and couples have been asking me if there are any Tantra teachers in the Midwest. I knew of one in Kansas City, but she disappeared a few years ago. It looks like there are one or two active goddesses in the Chicago area.

I’ve dabbled in it – reading books like Urban Tantra, browsing websites and watching videos, but am by no means an expert.

So over the years I’ve put the word out to the local community seeking tantra experts. I found one man who was willing to speak to my group Sex Positive St Louis, but he canceled two hours before the talk, so I had to wing it!

I talked about my experiences with yoni eggs, energy orgasms, extended orgasms, kundalini, and more.

The Sacred Prostitute

The Sacred Prostitute

Recently, we found another man in St Louis named StarDancer who was willing to talk about his energy body work to the group. Hearing him speak really inspired me to investigate the Tantra realm further.

I had a revelation – I want to bring Tantra from a female perspective to St Louis! I already do sex surrogate work as a sacred prostitute, so this seemed a natural step in my career as a sexuality expert.

I found out that Barbara Carrellas is offering a Tantra training workshop in New York City June 10-16. Thanks to some generous sponsors who believe in my mission, I AM GOING. I’m SO excited! It will be my first time in New York City. I can’t wait for an invigorating change of scenery and for my universe to expand!

Barbara was featured on Strange Sex demonstrating her full body energy orgasm technique, aka “thinking off” for a group of scientists. She’s the real deal!

Here is more info – Barbara’s intro on the program

More about the program

Details about registering for the program

More info on Barbara Carrellas – she’s a certified sexologist who has worked with the likes of Annie Sprinkle teaching Sacred Sex techniques! She’s very inclusive and positive in her teachings – more practical and modern than woo woo, she revels in, teases, and plays with traditional Tantra, all while honoring Tantra’s rich spiritual tradition of connection. She teaches all over the world, so it’s nice having a class offered in the U.S.

I’m excited to bring what I learn back to St. Louis. Thank you for believing in me and helping expand our collective sexual universe!

Sex work can be a beautiful thing.

Sex work can be a beautiful thing.


My Favorite Sex Toys for Men

By Kendra Holliday | May 7, 2016

The other day someone saw my sex toy curio and remarked, “You sure have a lot of toys for women in there.”



Well DUH.

My partner has a lot of toys at his house, too, more of the male and BDSM stuff.

Here are some of my favorite male toys – I recommend these all the time:

Tenga Flip Hole – My partner Matthew reviewed this a while back. I like it better than the Fleshlight. I have to say, he wrote that review five years ago, and he still has that thing and uses it from time to time! It holds up well. Personally, I think it’s really hot watching a guy jack with a toy. Sometimes I’ll look that stuff up on porn sites. It’s interesting how quiet men are when being stimulated, but when they cum, they make sexy noises that turn me on.

Tenga Egg!

Tenga Egg!

Tenga Egg – Women have their yoni eggs; men get Tenga eggs! These are so much fun! While the Flip Hole above is meant to be used again and again, the Tenga Eggs are cheaper and more disposable (though you can use than more than once if you want to). I keep a basket of them by my bed – they come in several designs.  I like experimenting with different men – some find the sensation to be spectacular. Some cum fast, some find it feels weird. One of the guys I tried it on was uncircumcised, and he wasn’t that impressed with it.

Cock rings – you can get a set of three silicone rings for less than $10. These are good to have around for backup, or just to switch things up a little. They restrict the blood flow from leaving the penis, so you get a harder, longer lasting erection. Don’t leave one on for more than 20 minutes, though – you don’t want to do any dick damage.


Baby Toy or Adult Toy? You Be The Judge

By Kendra Holliday | May 1, 2016

So one day I posted a video on my YouTube channel showing off the difference between two vibrators and how they sounded. It got yanked for being inappropriate, due to the fact that I held an adult toy in my hand for less than 30 seconds. I duplicated the video here, only this time I used kid toys in place of the adult toys. This time it was considered appropriate, and got to stay.

That got me to thinking about baby toys vs. adult toys. (By they way, when my daughter was seven-years-old and found my sex toy stash, she exclaimed, “I’m so glad grownups get toys, too!” Such a healthy response!)  Below is a series of toys. Can you guess which is intended for babies, and which are for adults?

Baby toy or adult toy?


Baby toy or adult toy?


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Always admired him and found his Gilda Radner love story so poignant.


A lot of my clients would like this NSFW tumblr: Women spanking men. Lots of CFNM, attention/humiliation


This is how I got into counseling - I had so many people asking for advice