Appreciate What You Have

By Kendra Holliday | February 6, 2016

Have you worshiped your goddess today?

Have you worshiped your goddess today?

I’m a sex surrogate. That means I work intimately with people in addressing their sexual issues. In other words, I’m a fucking therapist! :)

I LOVE what I do, but it’s not all fun and games. I sift through a lot of painful baggage. It’s incredible what people have to endure! I do my best to feel for them, and WITH them. I want them to unpack that baggage, but it can be hard to accomplish in just a few hours – they’ve been gathering it for years. What a burden! I try to lighten their load, in a fun and loving way.

Here are some examples of what my clients are dealing with:

losing a wife suddenly

never having a partner

orgasming too quickly

inability to orgasm due to back surgery

inability to feel orgasm due to anhedonia

erectile dysfunction due to heavy emotional baggage

erectile dysfunction due to a million other things – 80% of ED is mental, 20% is physical

married but haven’t had intimacy in more than ten – or twenty – years

lack of intimacy


Why is Online Dating So Challenging?

By Kendra Holliday | January 31, 2016

A male friend of mine recently joined a few online dating sites. He set up a profile, and started contacting women. Instead of shooting them, “hi how r u” grunt messages, he made sure to use respectful language and demonstrate that he had read their profile.

He was dismayed to learn that most women never even bothered to reply back.

“How rude!” he exclaimed to me. He went on to explain his perspective as man trying to use online dating sites. His complaints were SO common to me. The vast majority of men find online dating to be a frustrating waste of time.

Why is this?

Please no cock shots

Please no cock shots

As a woman, I know what it’s like from a female perspective.

When I first join a dating site, even when I don’t have a picture posted, I get 20 emails from men in 20 minutes. And they keep pouring in, so many you can’t keep up with them.

If you have a nice profile with a pic and you’re attractive, then you get hundreds of messages a day! It’s nuts! I try to respond to every one, but it’s impossible. I give up.

I finally just respond to the ones who stood out. And then, feeling guilty and drained, I eventually delete my account.

It’s like a feeding frenzy. You feel a bit attacked and it can create smugness in the woman. She has all the power. The men come off as so plentiful and eager – desperate, even. And THAT is a turn off.

Some of them will hatefully insult you if they don’t get their way. That’s even MORE of a turn off.

If you think not replying to a message is rude, how about this? My friend Ruby Ryder shared this experience:

When a 59 year old man on OKCupid uses the words “lick pussy” in his second message, I can’t get to the block button fast enough. That was after I politely responded and told him we were not well suited, wishing him luck in his search. Sometimes internet dating is really disgusting.

This shit is epidemic and counterproductive.


WHY is it that way?

Because of society. Society pits male sexuality against female sexuality. In our society, men are taught to fuck and destroy. Women are taught to be passive and love. Male sexuality is plentiful and cheap. Female sexuality is scarce and valuable.

It makes no sense when we’re 50/50 of the population, right? But due to slut shaming and objectifying, female energy is turned into a valuable commodity, which creates resentment and imbalance.


Do You Know How to Make Women Feel Comfortable?

By Kendra Holliday | January 31, 2016

Scared and desperate. Photo by Steve Truesdell

Women deserve worship. Photo by Steve Truesdell

If you are a man who craves female energy – caressing soft skin, cuddling with a beautiful woman, inhaling her unique scent, sucking on supple breasts, touching beguiling pussy, being inside a hot, wet woman – the best way to enjoy ALL the priceless female treasures is to

make the woman feel comfortable.

Help her relax. Ensure that she feels secure in your presence. It’s best for the situation to unfold to the point where you can clearly tell she WANTS you to touch her. Err on the side of caution. Leave her wanting more. Read her body language. Listen to what she has to say. Treat her the way she wants to be treated.

If women are happy in our society, then men and children will follow suit. The happiness of women is KEY to a utopian society.

So many testosterone-driven men think about their penis first, and everything else second. This is immature, backwards thinking, and it won’t get you very far. A penis-first mentality leads to frustration and resentment.

Instead, try and replace that mindset with a “female energy first” way of thinking, and the effects will flow into your ego and penis, which means the woman will be pleased and satisfied, and so will you!

Let me give you a couple examples of what I’m talking about.

The other day, I hosted one of my TBK play parties. As a woman comfortable in her own skin, I quickly shed my leopard print dress

and was running around the party naked. Hey, it’s MY orgy, and I can run around naked if I want to!

I chatted up one of the male guests I didn’t know well in the hallway, complimenting him on his handsome hazel eyes, and learned about his passion as a painter. He was also nude, save a leather cock ring that prominently showcased his projectile penis.


Find Me at Naughti Gras

By Kendra Holliday | January 30, 2016

Here’s a kinky photo my photographer friend Stan took of my friends and me. You can see it at Naughti Gras this weekend:

Sexy submission

Sexy submission

I love the triangular dynamic happening in this shot – the dominant women, the submissive man. This was a dream come true for him! So much fun exploring the creative world of art and sex.

The Mad Scientist Lifestyle: 15 Ways to De-Borify Yourself

By Kendra Holliday | January 26, 2016

Live like a Mad Scientist & get laid!

I asked my friend RainMan to share some of his alternative lifestyle habits with The Beautiful Kind community; clearly he’s a man who thinks outside the cage. And it works – it gets him laid! Here is a peek into his weird world, in his own words:

“How many times have you been approached by, gone on a date with, or even married someone who is best described as Generic Humanoid #17?

The woman whose entire life is work, Facebook and fruity drinks with her girlfriends every Saturday night.

The man whose entire life is work, video games, and NFL Sunday Ticket.

The married couple whose twice-a-month sex life consists of the same two positions every time, carefully scheduled between episodes of Desperate Housewives and the ballgame.

Is it any wonder people trade in their spouses as often as their cars?

Kendra has had glimpses into the insanity that is my world, and she jokingly called it the “Mad Scientist” approach to living: doing things just to see if you can, changing your life around just because you can.

The crux of this is constantly challenging yourself. Rather than spending life coasting along, why not mix things up? Do something that forces your to consider life from a different perspective. Each time you do this you grow, even when you fail.

I’ve tried all of the following examples at one time or another. Some won’t be feasible depending on your specific circumstances (wife/husband, kids, disabilities, etc), but your options are only limited by your imagination.


His n Hers Vacation

By Kendra Holliday | January 15, 2016

Ahhh, this weather reminds me of the time my partner Matthew and I ran away to Key West Florida for a decadent getaway a few years ago! Here is a slice of how we do vacation:

My crystal ball says you will have an awesome time in St. Louis.

Make your vacation sexy and mysterious…

Wednesday night was my night. I got to call the shots, so we had dinner at Better Than Sex, a dessert restaurant swathed in our colors – burgundy and gold.

I had fun ordering for Matthew – he had the Tongue Bath, and I had the Peanut Butter Perversion. He drank an apple cider out of a pilsner glass dipped in caramel, and I had a tawny port rimmed with dripping chocolate.

When we got back to our place, I had my way with him.

I pretended I was a lesbian staying in the villa next door. I had partied with him all day with my girlfriends, and when they went out to hit the bars, I stayed back in order to sneak over to his place.

I didn’t want my girlfriends to know I was craving his dick, that I wanted to use him as a sperm donor so I could get pregnant and go back home and never see him again.

He was lying in bed, was just thinking about jerking off before falling asleep, when I entered his bedroom like a cougar on the prowl. He was completely surprised that I was seducing him, especially after all the male bashing jokes I had teased him with all day, but he was going with the flow and surrendering himself to me. I kissed him passionately and climbed on top of him. My sarong hiked up, exposing my strong, smooth thighs. I wasn’t wearing any underwear.

In the dim light I ground into his hard cock. I felt the heat through his boxers, and was desperate to get it inside me before he came to his senses and suggested a condom, or stopped me altogether. I pulled down his shorts, and it sprang loose, straining to be taken.

I took it.

I impaled myself on it, rode him hard, disgusted and turned on by his maleness. I couldn’t help but seize onto his beard and hairy chest.

He whispered that he was going to cum, giving me one last chance to avoid his potent load, but I clamped my thighs around him like a praying mantis seizing her hapless mate, and I sucked his climax up greedily into my womb.

As soon as I got what I wanted, I rolled off of him and passed out.


Cabin Advent Calendar

By Kendra Holliday | January 6, 2016

We disappear here.


Matthew and I go to the same 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 music playlist
old traditions
new ideas
sex-scented beard






The Mango Talk: Sex-Positive Conversations with Kids

By Kendra Holliday | December 29, 2015

Sex is like a mango

I wrote this post five years ago, when my daughter was ten. Now she is fifteen, and still working through her teenage hormones! Join us this Sunday, January 3 for a FREE Sex-Positive Parenting talk at The Ethical Society at 9:45am!

Being pregnant was an incredibly interesting experience.

Having a baby was cute, fun and exhausting.

Toddlerhood was my least favorite stage – I felt like a classical music lover at a speed metal concert.

The solid kid stage (4-9) was the best, and I thought I’d get to enjoy it for another year or two, as my daughter just turned 10.

After all, I didn’t start freaking out until I was 12, and I got my period when I was 13. My mom didn’t get hers until she was 14.

Girls are developing much eariler these days thanks to improved health and diet. Surprise! My daughter is tweening, and it’s giving me whiplash.

One night this summer, the hormone fairy snuck in and replaced my sweet child with this half-finished mutant version of myself.

She’s starting to develop. She’s insisting on training bras and sanitary napkins for just in case. She’s crying one second and laughing the next. Have you ever heard about how bitchy trans folks get when they have their hormone shots? My daughter is as dramatic as a drag queen downing diva cocktails.


Crashing the Party

By Kendra Holliday | December 27, 2015

This post recounts one of our most memorable New Year’s Eve, a few years ago…

Kendra Holliday, Party Slut Extraordinaire!

Kendra Holliday, Party Slut Extraordinaire!

“Did you remember the butt plug?” I asked Matthew as we drove down the icy road.

“DAMMIT!” he exclaimed and thumped the steering wheel. “I’m turning around.”

“No you’re NOT!” I crowed.

YESS, I wouldn’t have to be subjected to wearing a butt plug in the hotel room as he attended his meetings.

“That’s OK, I’m an Eagle Scout,” he drawled. “I’m sure I can rig something makeshift, like a toilet paper roll or something.”

“Fat chance!” I retorted, arms folded smugly. Then I added with a smirk, “Maybe you can pick one up in the hotel gift shop.”

We were headed to an exclusive New Year’s Eve bash at a swanky hotel in Kansas City. The person throwing it was a Major League Baseball Player … (ok, the person throwing it was his beautiful bulldog wife, OK, the person throwing it was Marcus the swanksexual party planner) …, and the baseball big shot needed a reason to spend a million dollars, so he decided to invite 500 of his closest friends to celebrate his fabulous life with him.

I am not one of his closest friends.

He doesn’t even know me. But my man was invited. And I was tagging along.

I was crashing the party.


HOT Nude Photos From The Cabin

By Kendra Holliday | December 22, 2015

Going back to the cabin in a couple weeks… looking at the pics from our visit earlier this year with great warmth and fondness… I’m ready for a break from all the madness!

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

Rustic and romantic!

We took this tasteful version of me wearing a vintage slip for facebook:

I can’t wait to take this slip off!

Then we took these classic nude photos for the blog.


Losing a Client

By Kendra Holliday | December 13, 2015

Kendra Holliday, operating on mutual respect since 2006

Kendra Holliday, operating on mutual respect since 2006

The other day, I came across this post on Cameryn Moore’s blog about death and sex work: When a Client Passes Away.

It gave me pause.

I’ve been a sex worker for almost 10 years, and a lot of my clients are older, and/or have disabilities. I’ve had clients disappear, but have never been confronted with a death.

I wondered what it would feel like to lose someone you have a professional, yet loving, intimate relationship with, that society may or may not approve of. Talk about complicated!

Unfortunately, I soon found out. Not even two weeks later, one of my client’s passed away unexpectedly. He was 35 years old with a severe disability. I was supposed to see him again Christmas week. It hit me harder than I thought.

M contacted me back in May with the following request:

“sexual surrogate for a quadriplegic disabled man”

M had Muscular Dystrophy, which, according to Mayo Clinic, “is a group of diseases that cause progressive weakness and loss of muscle mass.”

We had an initial consult via Skype. He had to use his tongue for typing. I teased him about it: “I can’t wait to see what else that tongue can do!”

I only spent a few hours with him total, but what special hours they were!

I had to travel to him, since he was so limited in mobility. He lived about an hour from St Louis.

Each session, he was sooo eager and excited! He didn’t get to explore his sexuality nearly as much as he would like to, so he was an apt pupil. We practiced kissing, oral, pleasuring a woman, and condom sex.

He’d be hard before I even entered the room – anticipation is half the fun! He trembled with excitement, and complimented me on my body – “you look good for your age.” Ha, thanks! :)

Since he couldn’t move his arms, we adapted a technique where he was able to get me off – “knuckle riding” – we lubed up his hand and I rode the back of it. His soft knuckles folded perfectly into my labia and clit, creating a sexy sensation that gave me tingles!

I taught him to relax his mouth while kissing, and suck my breasts in a way that I enjoyed. I boldly stood above him so he could get a good look at my pussy, and carefully lowered myself on his face so he could taste the bittersweet tang of sacred femininity, being sure not to dislodge the tracheotomy tube attached to the base of his throat. He wasn’t as fragile as I thought he was – I was able to climb all over him and experiment with different positions. He was able to feel giddy waves of pleasure, and orgasm without ejaculating.

Most men keep warm – testosterone is nature’s furnace – but the men I’ve been with who have Muscular Dystrophy are more like me – they get cold easily. So we would cuddle under blankets together and talk about plans and dreams. We would gaze into each other’s eyes. I would stroke him all over and press my soft body against his. He beamed with joy. He loved live music, his pets, and the beach. And most of all, he loved women!

I last heard from him on Dec 1. We were discussing our upcoming session the week of Christmas.


So You Want to be a Sex Worker…

By Kendra Holliday | December 13, 2015

Hello! Do I know you?

Hello! Do I know you?

I’m hosting a special SEX+STL event next month!

So You Want to be a Sex Worker…

When: Tuesday, Jan 5, 7-9pm

Where: private location

Cost: $20 per person

This event is screened and private and for women only.
(In order to attend a SEX+STL private event, you need to attend one of our public events or meet one of the leaders first.)

Interested in learning about sex work? How do you find clients? How do you stay safe? How do you keep healthy? How much do you charge? What kind of situations might you encounter? Where should you do it? What are the rules? All these questions and more will be honestly and frankly answered at this fascinating and rare opportunity. Be ready to take notes!

Kendra Holliday, a seasoned sex worker, will share tips and best practices for being a successful sex worker.

Practicing and former sex workers, and those curious or serious about trying sex work are welcome to attend.

RSVP to to request a spot.

$20/person. Bring a snack or drink if you’d like.

Topics covered include phone sex, dancing, escorting, erotic massage, surrogacy, dominatrix and more.

Come learn the secrets of The Sacred Prostitute!

You, too, can be a sacred prostitute goddess!

You, too, can be a sacred prostitute goddess!

Why I Love Inexperienced Men

By Kendra Holliday | December 10, 2015

One of the best parts of my job as a sacred prostitute is that I get to spend time with adult virgins. And every time I do, there is one less adult virgin in the world. :)

After a recent encounter, one of my former virgin clients shared this with me:

Porn has almost completely lost its luster for me. I find it vastly inferior to the memories of the experience I had with you in St. Louis, and those are just memories! All I have to do is think of you – of your smell, eating your pussy, kissing you, fucking you, feeling your weight against my body, intertwining my legs and arms with yours – and I am instantly aroused beyond anything porn can do for me. Frankly, now that I’ve had a taste of the real thing, it’s hard to see porn as anything other than a pale imitation of what sex is really like.

Yes I'm easy!

I love helping my fellow man.

This man and I would love to have another session, but logistics are challenging – finances and distance – he had to drive hours to make it happen, which I think is very brave and commital – Cowboy Ethics! Ride for the Brand!

By the way, inexperienced men tend to be some of the best pussy eaters! It’s TRUE. ESPECIALLY when they read and research in preparation for our sacred encounter – two great articles to read before you enter my bedroom chamber is “How to Eat My Pussy” and “What I Like and Don’t Like.”

That’s not the only reason I love inexperienced men. They’re more respectful and grateful. You get to teach them how to be good lovers. I wish I could get to them when they’re younger, before they’re warped by porn and misinformation, but society can’t handle that.

One of my clients is quite unique – he has sickle cell anemia, which is a rare blood disease.

Here is the initial request I received from him:

My name is Robert and I am 38 years old. I saw an article about your blog in the RFT. I’ve been reading your blog off and on since then. I’m learning a lot from your advice and the advice of others on your links column. The experience has really been enlightening. I hope you can enlighten me some more.

I have sickle cell anemia. It’s a blood disease that misshapes the blood cells and make them pretty much incapable of carrying oxygen through the body. Their odd shape can get them stuck in the bloodstream; it causes chronic excruciating pain that needs medical attention. It can be deadly in some cases. Eventually, the body’s organs become negatively affected.

I suffered a stroke when I was 17, my senior year in high school. I was diagnosed with kidney failure in 2002 and started dialysis in 2003.

Throughout my teens, I was really sick, so I relied on my parents to take care of me. This made me decide to stay away from any kind of personal relationships. A couple of months after my stroke, I declared myself asexual; I figured no woman would want to be in a relationship with someone who wasn’t totally healthy.

After the kidney failure diagnosis, I started dialysis in 2003. In the five years of dialysis, I had only one bout of severe pain. I owe it all to my changed lifestyle of eating better and exercising as much as I could tolerate.

The positives only got better from there. In the summer of 2007. I got on the transplant list. In 2008, I got a new kidney. I now have a clean bill of health.

Last year, I declared to myself that I would now seek out a relationship, and if the friendship turned into something more, I would see where it goes. I am healthy and confident enough that a love life would be sustainable for me.

My problem is that I’m still anemic. That’s never going away. I get fatigued easily. At this stage of my life, I’m wondering about sex. I don’t know how long I would last and what I could do.

I love my doctors, but they’re not sex therapists, so they can’t really help with this worry. If I’m in a relationship that involves intercourse, I need to ease myself into the act and last for as long as it takes for both of us to be satisfied. Can you help?

Waiting for your kind words with baited breath,

I was intrigued. Right away I did some research on sickle cell anemia and sex and found there isn’t much out there. You’re supposed to drink a lot of water to hydrate yourself, and men tend to have prolonged erections. Looks like we’d have to learn together!


My Bra Fitting

By Kendra Holliday | December 5, 2015

As Queen of my Realm, I have been blessed by many royal subjects, and one of them is my Lingerie Fairy. He is a Blue Collar Man of the House – he works hard, is married to a good woman, and takes care of his special needs grandson. He was featured in this post a couple years back!

Well, sometimes my friend H drops off lingerie for me on my front porch. Royal blue, peach, leopard print – the gifts tend to be classic sets – panties, bras, even stockings.

And sometimes, H is AKA Dorothy, a woman who loves playing dress up. Here is a recent, chestwarming story!


Such a classy brand and style!

Such a classy brand and style!

One of the things I have been wanting to do was have a proper bra fitting. Being the fact I am a male by gender and a cross dresser for life, this is not as easy as it may seem.

I have been wearing bras most of my life. I have an obsession with bras. I have over 100 bras in my collection, even after donating 50 bra’s for a Battered Woman Shelter.

I have asked at Department stores and have received discouraging messages. “I don’t know if we can do that here”. “You need to have the Men’s Department Measure you”.  The trouble is, I only want to experience what genetic woman experience to satisfy my female side.

I came across a story on one of the blogs that I read called Lingerie Briefs. The article was titled “Men Who Wear Bras: An Underserved Lingerie Market“.

In the article, it talks about men getting proper fittings. I found out by reading this story I have a better chance getting a proper fitting by going to smaller boutiques or a bra specialty shop. Now my search was on the right direction.

I found Ann’s Bra Shop by doing a local search. I sent an email asking if they would do proper bra fittings for men.

I received a reply several hours later they would do bra fitting for men. I exchanged several e-mails asking questions about locations in my area. I made an appointment for the store in O’Fallon Illinois.

Betty does the bra fittings at the stores on different days. My work days and the days she was there did not work out. Betty asked Courtney who works in the O’Fallon store if she had a problem doing fittings for men. Courtney stated she would be fine with tat. So my appointment was set!

I had talked to several friends including Kendra as to what to wear to my fitting. I was thinking of wearing my red Chantelle bra, red blouse and a touch of perfume to go with my look.


A Sex-Positive Gang Bang

By Kendra Holliday | December 4, 2015

SO. This week’s Savage Lovecast featured a woman calling in asking about a gang bang gone wrong. You can listen to it here, around the 30 minute mark. The good news is, she had two gang bang prior to the bad one that went GREAT, but the last one tanked. The reason: the men got too rude and selfish. Dan gave her great advice – have a gang bang buddy, and know who’s in the room! Below is my super amazing gang bang experience. I hope you take some ideas from it if you’re thinking about staging one for YOUR loved one (that includes YOU!) A loving shout out to the people who were involved in mine – they all made it so very special. It truly was a dream come true – it made for a VERY happy Holliday! 😉


Would you be nervous if you knew eight men were on their way over to fuck you all at once?

Would you be nervous if you were a man driving to a gang bang event, having never met some of the other guys, and this being a new experience for you?

Think about it for a minute.

I mean, gang bangs seem like a hot idea in fantasy, but how do they translate in reality?

Well, when you plan it right, they translate really fucking well.

Truth be told, I wasn’t nervous. I was excited. I was radiant.

This pic was taken after it was all over. Photos by David Wraith!

This pic was taken after it was all over. Photos by David Wraith!

Now, if I was about to do public speaking, I’d be nervous. If I was about to parallel park a car, I’d be nervous. If I was about to walk into a rich country club, I’d be nervous.

But this was natural for me, even though it was my first time trying such a thing. As you all well know, sexual acts are where I shine.

Here is me right before the guests arrived:

Kendra Holliday, Slut Extraordinaire!

Kendra Holliday, Slut Extraordinaire!

See? I’m making the OK sign. :)

I dressed up because all the guests were coming in suit and tie. Classy!


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Appreciate What You Have

Why is Online Dating So Challenging?

Find Me at Naughti Gras




So nice having a strong, capable, attentive man!


I did, and he lowered me back down on the bed, and it was like slipping back into the warm, silky sea.


I felt like a mermaid being plucked from the ocean by her tail. I yelped, "What are you doing?" "Relax," he said.


ALL evening he had his big, warm hands on me. At one point, he picked me up by my ankles to stretch me.