My New Profile Pic

By Kendra Holliday | February 6, 2015

Background story to my new profile pic on this site, twitter, and facebook:

On Holliday!

On Holliday!

I know it’s blurry and raw, but it perfectly captures my spontaneous, happy, natural, sex-positive essence, right down to the little sparkling gem over my heart! You can even glimpse a bit of underarm hair, which a lot of men L O V E.

In other words, I’m freshly fucked!

Here is how the gem looked before I got naked. We were having a fancy dinner:

* Sparkle! *

* Sparkle! *

The night these photos were taken was a special night – a kinky client from out of town had an unusual request. He was in town for business, and he booked a fancy suite in a luxury hotel with grand marble floors and the smell of gingerbread wafting through the opulent corridors – it was December and they had a huge gingerbread house with sugar glass windows and a roof dripping with white icing, constructed in the lobby by a team of chefs.

While he was out for dinner with clients, he invited me to use his room – with my man. He wanted to come back from dinner and find his bed used, the scent of sex lingering.

I was VERY happy to oblige!

Here are some other pics from the evening:




Should I See a Sex Worker?

By Kendra Holliday | February 1, 2015

Remember reader Creideiki who posted about his first time with a sex worker? Here are some thoughts he wanted to share with other men pondering the idea:


Victoria's Secret

Mmm, Victoria’s Secret lingerie

Recently a male friend of Creideiki’s lamented:

“I am coming up on nine years without sex and it’s eating away at my self esteem, and making me suspect that women regard me with a basic contempt, at least romantically. Pretty much the last time I had successful sexual intercourse, my daughter was conceived. There have been a few unsuccessful attempts during those years, but I prefer not to think about that.

So the question is – what do I do about this? I’ve tried dating and that hasn’t worked out. I’m no good at picking up women, and prostitutes are out because I have no way of confirming they are doing so of their own free will.

I’d like to change the situation but have no clue how to do so except to continue my flailing dating life. Suggestions are welcome.”

Creideiki sent him the following message:

Hey Friend, I used to be in a similar boat and thought prostitutes were out. But when I started researching it, I learned a lot about the industry – and a lot about myself.

I can teach you the ropes if this is a route you want to take, but before you decide, I would encourage you to answer the questions below for yourself.

1. Why do you want to have sex? I realize the instinctive answer to this question is most likely, “well, DUH!” I was in a good place mentally, but my sex drive was getting very strong and I just felt like it was way past time for relief. For me, though, the full answer was more complex. I felt like I had literally forgotten how to have sex, and had forgotten how it felt to be with a woman. Plus I was, frankly, petrified of going into a sexual situation with a girlfriend after such a long layoff and not remembering what to do. I wanted to experience sex again, while my health and some of my youth remained.

2. How much do you want to spend? I developed a budget for seeing sex workers. No, seriously. My criteria was that I would spend money on sexual companionship only after all of my other financial obligations were taken care of. That included bills with aggressive paydown of debt, putting budgeted money in my two savings accounts, and paying for my aboveboard activities such as (legit) dating and dancing. I set up my life deliberately to live below my means, so that I would have financial flexibility, and that gives me financial space to see providers. In my area the going rate for an hour with an escort is $200, and for the so-called “elite” escorts their rates can be $500 or more. That’s substantial money, even on my very good income.

3. What are your ethics for this? In the U.S., paying for sex is illegal in 49 states, so the sex industry ends up being a very gray unregulated free market, unlike in other countries, such as this openly advertised “Babes of London” escort service in England. When I was researching seeing a provider, I found that there were providers who were independent, and in the sex industry of their own free will. Streetwalkers were never considered, and I eliminated the so-called “Asian Massage Parlors” from consideration because of human trafficking concerns. Rachel, my first, and so far, only provider, is an independent woman who chose to go into sex work after working in the corporate world. For me, if they are in it of their own volition, especially if they have other career choices, that rests well with my ethics, and I see no ethical dilemma in paying for their services. Almost invariably, it’s the women who are 30 years old and older who fit this profile.


myLAB Box – Safe is Sexy!

By Kendra Holliday | January 25, 2015

As a promiscuous sex worker and educator who has had the pleasure of hundreds of sexual partners, I get tested for STI’s on a regular basis. I’ve tried all kinds of options – my private doctor, Planned Parenthood, county health clinics… (I’ve compiled a list of local resources on the SEX+STL Links page, under “Sexual Health”.) Some are cheap and take two weeks to get results, some are pricey but fast, some are creepy and judgmental.

Well guess what? I just added a new, very cool sex-positive option!

It’s called myLAB Box.   TA DA!

myLAB Box allows you to test yourself at home!

myLAB Box allows you to test yourself at home!

It’s like a pre-party in a box! HA!

Before you jump into your next orgy or TBK Party, you should read this very practical guide on STDs by Mark Manson, and make plans to get tested.

I just tried out myLAB Box, and it was great!

After reading this scary article that St. Louis ranks highest in the nation for cases of chlamydia and gonorrhea, I thought that would be a good package to purchase. At $80, that’s about $40 per test – not bad!

Here’s how it worked for me:

1. I went on the website and ordered my tests.

Reading is sexy!

Reading is sexy!

2. I got myLAB Box kit delivered via UPS, straight away and right to my front door.

3. I spread the kit out on my table and carefully read all the instructions. The instructions were easy to follow and it only took five minutes to collect the sample.

4. I washed my hands and collected my sample in the bathroom – one vaginal swab for both the tests. (You can even turn it into a medical roleplay scene, hee hee!)

5. They provide you with the correct shipping stuff to return it easily – a biohazard bag, box, lab form, even a ready-to-mail UPS pouch.

6. I dropped my package off at UPS (you can arrange for pickup as well).

7. Within the week, I got an email that my test results were ready to be viewed online.


My Daughter and Me

By Kendra Holliday | January 25, 2015

This is a picture of my daughter and me, from half her life ago:

My daughter and me

My daughter and me

She was 7 in this picture. Now she’s 14!



She is slightly bigger than me. I never imagined that! Taller, bigger boobs, feet, etc. But we’re still pretty close in size, and share clothes.

We also share a super intimate, platonic relationship. She’s my top priority. We’re both proud of each other, and we’re both moody and crazy women. We share an unconditional love; accepting each other for who we are.

She is fine with me being a super slut goddess, and I am fine with her being a panromantic graysexual.

So last weekend, when I needed to attend a SEX+STL roleplay talk at Shameless Grounds, I told her I was going to the talk and would be back in a couple hours.

She immediately piped up, “Oh can I go?”

She’s geeky and loves roleplay.

I said, “You don’t understand. This is SEX roleplay talk.”

She snorted. “Of course I understand. Why wouldn’t it be about sex if it was one of your events? I’m curious about these things and I think I can handle it.”

Unconvinced but open to the idea, I negotiated, “If you go, do you agree that will let me know if you are uncomfortable at any time and would like to leave? And do you agree that we can talk openly about it afterward?”


Cabin 2015

By Kendra Holliday | January 18, 2015

This was our seventh year at the cabin! Such a magical place to reconnect!

The drive there is always fun – we stop in small towns and look for weird and new things to explore. You know, like the world’s largest rocking chair.

One outpost has moonshine tastings – 12 different kinds! We got apple pie and egg nog flavor, which is amazing in root beer.

Cuba, MO has an Amish store where we bought the most amazing cinnamon rolls.

Finally, we arrived at the cabin in the woods, near a lake:

Cabin in the woods!

Cabin in the woods!

As soon as we got there, he built a fire and made us whiskey cocktails. In celebration, I threw my panties on the fire – I couldn’t help myself! They were kindof ugly anyway. No undies for the rest of the weekend! We mostly stayed in robes or were naked.

We brought loads of pillows and super soft blankets to snuggle up in by the fire. One of them is a fake fur pattern – made me feel like we were in a cave!

I loved stroking the fur, and then my soft tummy, sipping hot toddies and reading gorgeous books, the fire crackling and throwing warm light:

Soft blankets, soft tummy

Soft blankets, soft tummy

We had an amazingly hot roleplay scene in the hot tub (SEX+STL is giving a roleplay talk today!)

Here is the path leading to the hot tub:


Cabin Advent Calendar

By Kendra Holliday | January 9, 2015

We disappear here.


Matthew and I go to the cabin every winter, and about two months prior, we start getting CABIN FEVER.

A couple days ago, he texted me: “I hope each morning, you’re opening the Cabin Advent Calendar in your head.”

I sure am! Do you want a peek inside? Open each little window and it will reveal:

Maker’s Mark
bourbon cake
hot tub
massage oil



country music
cabin playlist – example!
old traditions
new ideas
sex-scented beard






Back to the Cabin!

By Kendra Holliday | January 8, 2015

We’ll be sitting in front of this in about 12 hours!

This is our sixth year going to The Cabin!

It’s our favorite yearly ritual – stealing away right between the holidays and giving ourselves the best gift – time for just the two of us.

For 72 hours, we’ll be living in our own private universe where time and the internet doesn’t exist. In between all the fucking and frolicking, we’ll stoke the fire and eat cake at 2am, watch a movie, float away in the hot womb of the jacuzzi, listen to music playlists that celebrate different aspects of our lives, sip Maker’s Mark hot toddies at 6am…

Previous years have been epic. Last year was a Beethoven theme. Other themes have been BDSM, Ginger, Videos, Western…

I think this year’s theme will be Game of Thrones…

He is my Sun and Stars… I am the moon of his life.

We’ll be far, far away, experiencing something new, and something positively familiar. We’ve had another whole year to strengthen our bond.

Funny how driving four hours from both our houses feels like coming home.

He wrote this note to me four years ago, and it still holds true:

We need a cabin for a weekend together,
undress beside the ashes of the fire.
Your white gown smells of burning leaves.
It’s cold outside but I penetrate you with heat.
I keep you with every inch of my soul.
I love you.
I hate you.
I AM over you, peering down upon you worn and wet.
Reverting to your fetal shape in a torrent of emotion.
I am the man who defines you.
You are the woman who adores me.
A Burgundy box of worthless treasure in priceless proportions.
I will soak the thorny stem I place on your grave.
I am over you, in ALL ways.
We, Dear Slut, are far from over…..


Adventures with Ginger at the Cabin

By Kendra Holliday | January 8, 2015

This year was the fourth time we’ve been to the cabin, and it flew by faster than ever. The day after we returned I was really grumpy, suffering from cabin drop and feeling very put out that I had to take care of all the necessary duties and resposibilities instead of lying around all tied up in front of the fire sticking ginger up my ass.

Excuse me?

Every year we enjoy all the favorite traditions (watching Westerns, building fires, stargazing, listening to Iron & Wine, wearing pajamas or nothing the entire time), but we also like to incorporate something new into our repertoire.

Lately I’ve been on a ginger kick. I love theme events, so I packed a bunch of ginger goodies: tea, men, liqueur, soda, and of course, the root itself.

I was determined to drink the entire bottle of The Big O (“there’s nothing fake about it” ) that weekend (we all have our goals), but I couldn’t quite get there. It started leaving a sickly sweet mossy film on my teeth that no amount of brushing could remove from my ginger-spiced psyche.

We also brought along this awesome vulva ornament our dear friend Rockabilly Girl gave us to hang above the fireplace:


Cabin Reprise

By Kendra Holliday | January 7, 2015

Another incredible weekend at the cabin.

The cabin is under new ownership now, so they made some nice minor improvements, such as new furniture, bedding, and this sign:

Ha ha

Ha ha

…unless you have a sex blog.

We had a fire going ALL WEEKEND, which apparently is as bad for you as smoking cigarettes, godammit. I guess it’s a good thing I don’t have a wood burning fireplace at my house.



Here’s a pic of me in the hot tub from a previous year:


HOT Nude Photos From The Cabin

By Kendra Holliday | January 7, 2015

You better believe the pics are hot – we were in front of a roaring fire all weekend!

Rustic and romantic!

We took this grandma version of me wearing a vintage slip for facebook and twitter:

I can’t wait to take this slip off!

Then we took these classic nude photos for the blog.


Sex at Dawn: The Prehistoric Origins of Modern Sexuality

By Kendra Holliday | January 5, 2015

Sex at Dawn, paperback cover

Last winter, Matthew and I were at our romantic cabin getaway. We had just fucked and were lounging in front of the fireplace, sipping cocktails contentedly. The cabin closest to us was occupied by a couple also trying to get away from it all. Unfortunately, they weren’t quite succeeding.

They were having a big fight.

Doors slammed. Amidst the commotion, we heard the woman scream, “You fucked someone else last night – I’m not stupid ya know!”

We looked at each other with raised eyebrows.

I drawled, “I’m glad the fact that you fucked someone else last week isn’t ruining OUR vacation.”

“Yeah no shit!” he agreed with a swig of his drink.

We toasted each other.

More drama floated through the trees our way. “I’m leaving!” the man cried, got in the car and drove off. He came back a few minutes later, knocking on the door. “Let me in!” he begged.

I rolled my eyes and joked, “Do you think we should go over there and offer them some relationship advice?”

“Fuck no!” he grunted. “Let them get their own damn copy of Sex at Dawn.”

He was talking about the book, Sex at Dawn: The Prehistoric Origins of Modern Sexuality.


My Last Sessions of the Year

By Kendra Holliday | January 1, 2015

Reflecting on the past

Reflecting on the past

As a sex worker and sex surrogate, I’ve met with a lot of amazing men, women, and couples this past year, in VERY intimate settings.

I have SO many fascinating stories, but can’t freely share them due to confidentiality.

I can tell you that I’m seeing a big disconnect between men and women.

The men are overheated and eager with testosterone. The women are cool and reserved with estrogen.

A lot of the men I work with are frustrated with all the erotic teasing that goes on in our society – watching burlesque shows, fruitless attempts at online dating, binging on porn, falling into the neutered Nice Guy role.

They get rebuffed by dozens of women, and they come to me, horny and keyed up.

I try to teach them how to build intimacy and accept themselves for who they are, but they just want to FUCK ALREADY.

Let me tell you – eager is not sexy. You have to go slow to go fast. In order to make progress in your quest for self-improvement, you have to be patient and make an effort.

The next time you are with someone, consider the 12 Stages of Intimacy. Read about them here. It’s important to build a foundation so that the intimacy you share is more meaningful and fulfilling.

Which brings me to the last two sessions I had this year. They were both on the same day.


Parents Keeping Their Kinky Play Private

By Kendra Holliday | December 27, 2014

Wild G Vibe from CalExotics - high quality and worthwhile!

Wild G Vibe from CalExotics – high quality and worthwhile!

Dear Kendra,

Thanks to the opening of an adult boutique in our area featuring incredibly helpful staff, my wife and I recently started experimenting with S&M and bought some new regular toys as well. As a result, we now have a few whips, a prostate stimulator, a rabbit vibrator and a few other goodies hidden in our closet in a place where, we hope, our teenager will never find them.

When my folks passed away ten years ago, my brother’s wife came across a box of videos and toys when we were cleaning out their house, which caused a bit of embarrassment in the “more than we needed to know” way.

Do you have any suggestions as to how we can avoid this happening to our kid down the road? My main concern about our toys in question has to do with the S&M aspect, something that even mature adults might find a bit disturbing.

I’m thinking a note on the outside of our toybag to the extent that “If you are finding this bag it is because: a- You are snooping; or b- Something has happened to the two of us. If you are snooping- PUT THIS BAG BACK WHERE YOU FOUND IT- we can talk about its contents and answer any question you have if you wish to do so. If something happened to us, please dispose of this bag without opening it. It contains items that we enjoyed during our intimate private times together and, as such, wish them to remain private.”

Dear Reader,

Why hide such beauty?

Why hide such beauty?

I’m of the mindset that toys are nothing to be ashamed of – I keep mine out in a display case. When my daughter was 7, we had a talk about sex toys and she was glad to know grownups get to have toys! She has been raised to understand sex is to be explored and enjoyed and can be playful.

How do you feel about your parents having a sex life? Are you glad they did, or would you rather never know the evidence of such? Well guess what? YOU are evidence of their sex life! Was the discovery of the toys a bit embarrassing, or mortifying? In the grand scheme of things, was it a big deal? Not trying to dismiss your feelings on this highly personal matter, just offering an objective perspective.

That said, if you have a different mindset in that your bedroom activities are private and kept separate from other aspects of your life, then your approach is a great one! I love the idea of you stashing the toys with a note that offers a chance to discuss or dispose – it gives the finder options. The wording of your note is sweet and positive, very thoughtful of you!

There is this option for hiding personal items: The Sneaky Sack. It’s a bag that is easily disguised under hanging clothes. That way, you can keep your sex life safely in the closet.

Sex-Positive? Or Sex-Sensitive?

By Kendra Holliday | December 27, 2014



I have to admit, as a feminist and sex-positive activist, sometimes I get tired of hearing people spout off the words “privilege,” “narrative,” and “agency”.

And don’t even get me started with the whole “trigger warning” babying.

If you are on the internet, you will run into triggering things.

If you are living in real life, you will encounter triggering things.

Right now, one of my triggering things is driving in cars. I got in a minor car accident the other day, and it has haunted me a bit.

It left me feeling weak and vulnerable, and I’ve had to make a concerted effort to rebuild my strength.

You can’t let little things chip away at your armor – words like “tranny” and “faggot” and “slut” should not ruin your day.

I get “people first” language, but if you take issue with so many everyday words and slang, you are not cultivating a sex-positive culture. You are fostering a sex-sensitive culture, and that culture is weak and fragmenting.

For instance, the other day I used the word “weird” in conversation, and someone called me on it. I had to circle back and explain that I meant “odd, unusual,” and not “a freak who should be shunned.”

I don’t want to live in a world where we have to walk on eggshells and speak academically. I don’t want to clinically discuss penises and vulvas. I want to talk cock n’ pussy!

My advice: Grow a thicker skin. Be patient with others. Educate respectfully. Don’t take things so personally. Learn how to process quickly and move on.


How I Met My Partner

By Kendra Holliday | December 25, 2014

Such a good feeling.

Such a good feeling.

I’ve had many women ask me how I met my partner Matthew. How did I find a man who is confident, dominant,  sexy, funny, smart, and can be a stern dick OR a tender lover – AND know the time and the place to assume such opposite-end-of-the-spectrum roles!

Most men can only be a nice guy OR an asshole. It takes special talent to be both.


He knows what a woman wants – she wants it ALL. She wants to be treated like royalty, AND a slut. She wants comfort, AND freedom. (Psst, isn’t that what men want, too?)

Someone even joked that HE’S the new unicorn – a man who is OK with his woman doing her own thing, aka fucking other guys.

I truly have the best of both worlds – I’m in a committed, secure relationship, but enjoy the privilege of doing what I want with my own body. Most women who commit to a man (or woman, for that matter!) turn over the keys to their freedom.

And I tell you what – Matthew’s willingness to go with the crazy flow has worked out well for him – instead of pushing me away or the relationship imploding, we’ve both had some AMAZING experiences as King and Queen of TBK.

So how did I meet such an amazing man? We tell family members we met through a mutual friend, which is true, but the REAL story is more complicated than that. But of course! It HAS to be interesting to be a part of my world. Here is the scoop. I’ll try to be as succinct as possible.


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