Naked at Our Age: Talking Out Loud About Senior Sex

By Kendra Holliday | August 11, 2015

“Can I borrow that book when you’re done reading it?”

I can’t tell you how many people asked me that question as I carried Naked at Our Age: Talking Out Loud About Senior Sex, by Joan Price around with me for weeks.

I absolutely adore Joan Price. She is a passionate advocate of living life to its fullest. She teaches ageless sexuality and doesn’t hold back when it comes to sharing tips for living a more fulfilling, sensual life. She boldly pushes past societal barriers, and she does so in a loving, accepting, joyfully positive manner.

Thank goodness SOMEONE is talking about senior sexuality, because guess what? Not everyone is obssessed with young, inexperienced hardbodies.

My friend David Wraith is attracted to older women.

My partner Matthew is into older women. He loves how in touch with their bodies they are. “They know what they want.”

This guy I just met was into women in their 40’s when he was 20, and now that he’s 40, is into women in their 60’s. He craves the seasoned softness of their flesh.

Even my 15-year-old asexual daughter expressed interest in learning about senior sexuality – “I think it’s good for seniors to be having sex,” she said matter-of-factly, “but I don’t really want to watch it.”

Naked at Our Age, by Joan Price

“Oh for goodness sake! You don’t want to watch ANYONE having sex!” I exclaimed with a laugh.

“True,” she agreed.

Here’s the thing – I have huge respect and admiration for people older than me. I’m 42. I’ve always been attracted to little old men. In fact, I have a huge crush on my partner’s grandfather, a wiry pistol in his 80’s who could probably hogtie you with barbed wire before you even had a chance to cry “Grandpa.”

My oldest sexual partner was 92 years old, He hadn’t had sex for more than 20 years, and he assumed his parts would still work. They didn’t. His penis had vanished from years of neglect.

The saying is true: USE IT OR LOSE IT.

I watched a documentary on Anna Nicole Smith and everyone interviewed in it talked about how disgusting it was that she married a man 63 years older than her. I find that judgmental attitude distasteful.


Wearing His Clothes

By Kendra Holliday | August 10, 2015

Have you seen this project by Hana Pesut?

She photographs couples before and after switching clothes:

Photo project by Hana Pesut

Kelly and Tim. Photo project by Hana Pesut

You can see many more on her website.

My partner Matthew showed it to me, and said, “We should do this!”

Trouble is, he’s 6′ 4″ and weighs 320 lbs. I’m 5′ 4″ and weigh 130 lbs. If he puts on any of my clothes, I’m not getting them back in wearable condition. Unless he uses my sundress as a bandana or something.

So for the sake of my wardrobe, I decided to do the project solo.

Here is me in my clothes:

I weigh a size 8

I weigh a size 8


Care for a Mint? No, REALLY.

By Kendra Holliday | August 9, 2015

Going places!


Guess what?

You have bad breath.

I’ll prove it to you:

1. Grab some floss. If you don’t have easy access to any, you have bad breath FOR SURE.

2. Floss a few of your teeth.

3. Sniff the floss. This is what your breath smells like.

Any food that is caught between your teeth and left there simply rots, right in your face. That’s why it’s important to floss daily – you don’t want a graveyard in your mouth.

The reason why I’m posting about this topic is because I run a sex worker group, and one of the most common complaints I hear from the women (besides clients being stingy) are johns with bad breath. It’s really hard to give the Girlfriend Experience when your partner smells like he ate a shit sandwich.

Conversely, I was at a Whore Happy Hour and one of the men complimented me on my teeth, saying the women he knew were sweet, but many had meth mouth and smoked. So I guess my nice grill is a good selling point, if you will.

SO, if you want others to enjoy kissing you, here are some easy tips on keeping your breath fresh n’ clean:

1. Brush your teeth twice a day. This is also good for your gums.

2. Floss daily. As they say, you only have to floss the teeth you want to keep! Glide is a good brand if you have crowded teeth and normal floss shreds.

3. Go to the dentist for routine cleaning twice a year. I don’t have dental insurance, but I still make this happen. A cleaning costs me about $150. Consider it skull maintenance.

4. Avoid coffee or smoking, but if you do indulge, rinse with water or brush your teeth afterward.

5. HYDRATE. Drink lots of water.

6. Eat more fruits and veggies, less meat. High protein diets are the worst for creating bad bacteria fumes as it decomposes.

7. Chew on parsley and mint! Eat your garnish at dinner, grow mint in your backyard and rejoice in the natural freshening powers of chlorophyll! Just watch out afterward for green stuff stuck in your teeth!

8. Listerine may actually do more harm than good because it contains alcohol and dries the mouth, which the bacteria tend to like. I use SmartMouth, it’s great! It shorts out the bacteria’s ability to breakdown and produce sulphides in your mouth.

9. Keep the mouth moist (god I hate that word) with sugar-free gum or mints. I always chew a piece of gum ten minutes before a date.

10. Tongue scraping is good. You can buy a scraper, but I just use a spoon every couple days or so. It’s crazy what can accumulate on the back of your tongue, it gets all thick and white, eww!

You can read more about halitosis here.

Do you have any fresh breath tips or bad breath horror stories to share? If you had bad breath, would you want someone to tell you?

Junk in Your Trunk

By Kendra Holliday | July 30, 2015

You know how they talk about baggage, being in the closet, etc.?

Everyone has baggage – daddy issues, mommy issues, family pain, abandonment issues, trust issues, inexperienced issues, break up trauma, secrets, shame, guilt, neglect, abuse, loss, betrayal, injury, fear, rejection…

I like to pretend our head is an attic, and our brain is an old fashioned trunk, crammed full of stuff we’ve collected from our travels.

What's in your trunk?

What’s in your trunk?

Space is really tight, and the stuff is jammed in there.

So, I propose this exercise to my clients.

Find the key that opens the trunk.

A skeleton key, for the skeletons in your closet

A skeleton key, for the skeletons in your closet

Open that trunk up.

Now, take ALL the stuff out of it – toss it around the room.

Examine each article – is it a piece of clothing? Is it a toy? Is it wrinkled? Is it moldy? Does it still fit? Do you want to keep it?

Address and assess each item. Acknowledge why it’s in your trunk, and decide if it’s something you want to hang on to.


A Polyamorous Formula That Works

By Kendra Holliday | July 30, 2015

I love to explore.

I love to explore.

(For some background on polyamory, please read my article Love Like An Ocean: Diving Deep Into Polyamory.)

My partner and I have been together for more than seven years.

We first met July 2007, at a friend’s wedding. We are in a long-term, committed open relationship. We started our relationship open. We don’t live together – we keep our families, homes, and finances separate. We see each other about 2 or 3 times a week. We are open to countless possibilities when it comes to sharing intimacy with other people. We deeply enjoy and appreciate our non-traditional relationship.

But it certainly isn’t a reckless free-for-all. In order to keep it healthy and drama-free, we constantly communicate with each other to ensure ways we can exercise our freedom while operating on mutual respect.

Outlined below is an arrangement that works for us.

It can be difficult balancing everything, but this is how we prioritize:

1. Kids

2. Careers

3. Our relationship

4. The people we are dating/close relationships

5. Social/volunteer/misc.

Sometimes we will date a person or couple once or twice, or just for a weekend when they come visit. Sometimes we will date a person or couple for a few months or longer. Usually lives change and shift so much that we ebb and flow into things naturally. It feels very fluid. We can date other people solo, or together.


On Giving, Boundaries, and Mutual Respect

By Kendra Holliday | July 16, 2015

According to this excellent and insightful psychology book by Adam Grant, there are Givers, Matchers, and Takers.

The other day I interviewed my daughter about her relationship with me. I asked her, “What is a quality you admire in me?” She replied, “You’re very giving, but you make sure people give back in return.”

In other words, I am not The Giving Tree.



Ha, ha! But seriously - nope.

Ha, ha! But seriously – nope.

I will help as much as I can, but I will not be used. I have boundaries, policies, and standards in place. I operate on mutual respect.

It amazes me how some people have no problem following my rules, and others just push push push my boundaries. Pushing boundaries = creepy. See Charlie Glickman’s explanation of this.

In our society, men are taught to be entitled to whatever they want, which conveniently matches up to the role women are assigned – to say yes and serve everyone selflessly.

Some people will hit me up for free advice on email or text. I’m happy to offer a quick suggestion, but I’m not a sheep in the meadow, just standing around for you to help yourself to a valuable snack.

Um, excuse me?

Um, excuse me?

My milk of human kindness is not endless and free. If it was, I’d dry up and keel over (not to mention homeless), and what good would I be then?


A Tribute From My King

By Kendra Holliday | July 16, 2015

Such a good feeling.

Such a good feeling.

I found these words of devotion from My King tucked away in a treasure chest. I’m not sure when he wrote this tribute, but seven years later, we’re still going strong…

“You are the absolute Love of my life.
You’ve been here for what I see to be the most unique and freeing segment my life’s timeline.
You’ve contributed immensely to the happiness and satisfaction that dominates my life.
I love learning; and through you, around you, next to you, because of you, with you,
I’ve become a much more intelligent man in countless, yet priceless ways.
With all five of my senses,
through four chambers of my heart,
in three dimensions.
Two puzzle pieces,
you are my number One.

– Matthew

MORE Epic Play Party!!!

By Kendra Holliday | July 15, 2015

Okay, so you know how I host play parties, right?

I’ve had some good ones, such as the one on Valentine’s Day weekend last year, and the one in April. I called that one epic, but the one last weekend was even MORE epic!

Epic: “a legendary work of art”

I’m SO proud that I pulled it off. I’ve hosted over ten of these parties, and they don’t get any easier. They’re SOO much work, and I don’t even break even. A labor of love, for sure!

In fact, this one will be my last for a while. I’m looking for someone I trust to take over TBK party organizing so I can focus on other projects. If I can find someone, you can expect the next one to happen in the fall.

I couldn’t do it without my core group of volunteers – the inner circle. And my partner, who doesn’t even like big party public sex. He’s an invaluable, supportive manager. And the party guests – they bring so much great energy and enthusiasm!

We had skinny dipping, a spanking bench, a girl pile, an orgy or two, and a gang bang! We even had naked fishing at 3am!

Let me run you through it.

We rented a big, secluded house in the country, on a lake. GORGEOUS.

The theme of the party was “Beach! BDSM! Bisexuality! Bingo!”

The only thing that was mandatory was the beach; all the others were optional. :)

The two big rules were CONSENT, and NO DROWNING.

Here I am, taking balloons out to the mailbox:

Let's party!!!

Let’s party!!!

Our friends catered the party – so delicious! Kebobs, fruit, veggies… gotta keep your energy levels up!

Guests started showing up at 7pm, wearing beach attire, and quickly stripped down and got in the lake.


Her Gang Bang

By Kendra Holliday | July 15, 2015

Ed Note: Here is my friend’s account of her gang bang experience at my last party!

A gangbang. Many, many cocks vying for the chance to penetrate my dripping pussy. This is the fantasy often discussed between myself and my partner during our one-on-one sexy time. It’s one of those things you watch in porn, think about while getting yourself off with a vibrator – but never really considered as a real-life possibility.

My partner and I have been participants in The Beautiful Kind parties hosted by the lovely Kendra Holliday since last October. The first time, we were merely observers – I had a little trepidation about asking others if they would like to play, and he was generally focused on making sure I was comfortable and happy.

I was thrilled to be involved in my first “girl pile”, however. I took from this party the satisfying memory of being in the middle of a pile of beautiful women, touching and tasting and teasing…

Our second party involved much more participation – both he and I played with other couples and individuals; I even left an impression (literally), which was mentioned at the end of Ms. Kendra’s post recap.

This summer, I’ve been working on my confidence, my health and my body; embracing all that life has to offer and getting rid of the things in my life holding me back from true freedom and happiness.

As the invite and updates about the next party rolled in, the idea to fulfill another fantasy started to take root. I asked my partner if he would be OK with me potentially getting fucked by a group of guys – he of course said yes; a more open-minded and supportive partner you would be hard-pressed to find.

I emailed Kendra asking if a gangbang at an upcoming party would be acceptable. She seemed more than happy to help me fulfill a fantasy and offered to help make it happen at the next party.


My Life Milestones

By Kendra Holliday | July 14, 2015

I’m 42 years old. Here is my life trajectory so far:

1973: I’m born in North Dakota. Brrrr!

My birthday suit, aka my first nude photoshoot

My birthday suit, aka my first nude photoshoot

1974: My family moves to Dallas, Texas.

1975: Who the hell knows.

1976: My brother is born.

1977: Um, Elvis dies?

Drinking the blood of Elvis

Drinking the blood of Elvis

1978: My sister is born. My brother throws up. I remember my first dream; I’m kidnapped by Captain Hook and held hostage with Raggedy Ann and Andy. He cuts off my foot and it looks like SpaghettiOs.

1979: My family moves to St. Louis.

1980: My baby brother is born, and dies two days later. My mom tries to kill herself several times, and when that fails, she burns his name into the back of her hand with a soldering iron. She is never the same again. A very dark time.

1981: Life still sucks. My mom is a complete wreck.

1982: My brother is born. My grandmother dies.

1983: I get molested by an older, adopted brother. It SUCKS. I get sent to therapy, and I don’t know why. I think I’m being punished. I am a victim.

1984: I have my first lesbian encounter. It’s hot and naughty. I’m 11.

1985: My baby sister is born. I drop her on her head, but don’t kill her. Skeptical about god’s involvement, I become an atheist.

1986: I hit puberty and middle school, and lose all my artistic talent and confidence. My family is poor white trash, and I am branded a zitty nerd. It sucks.

1987: My mom keeps getting crazier and crazier. It makes me crazy, and I attempt suicide. I spend time in three different mental hospitals. I lose my virginity to a 24 year old creep with a mustache because he keeps badgering me and I finally give in. It sucks.

1988: My moms tries to kill herself again. I put pressure on her slashed, gaping arms as my dad calls the ambulance. She gets hospitalized a lot, and OD’s, and gets shock treatment. I fuck around and feel very confused. It sucks.


Are You Afraid to Come Out as Sex-Positive?

By Kendra Holliday | July 6, 2015

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

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

A lot of my friends have to hide their involvement in my group, Sex Positive St Louis, from their friends and family.

A lot of my friends have two facebook accounts – one for their regular self, and one for their naughty self.

Look, I get keeping your private life separate from work – your job is a professional space, and your personal life has no bearing on your work performance. (I wish the company that fired me five years ago realized that!)

But friends and family – they LOVE you. And wouldn’t it be nice if they could accept you for who you are? Accept that you think sex is natural and fun. Accept that you have multiple sex partners. Accept that you do sex work. Accept that you write erotica or have a sex blog. Accept that you attend sex-positive events.

Why can’t they accept those parts of you? Are they old-fashioned? Conservative? Religious? Judgmental? Jealous?

Would they rather you be boring? Miserable? Ordinary?

And if you want to keep that side of yourself private from most people, that is totally fine – but DON’T live in fear that they might find out. Don’t let that keep you from attending a sex-positive event or exploring your sexuality.

If you have a friend or family member you’re afraid of learning the sexual side of you, why? What’s the worst that can happen? They’ll hate you? Disown you? Shame you? Shun you? You’ll hurt them? You’ll have to deal with the fallout? You’ll get sued?

Guess what? If you are a grown person, you are allowed to make your own choices and be yourself, as long as you’re not hurting other people.


My First Time With A Whore – Amsterdam Style

By Kendra Holliday | July 5, 2015

Ed Note: My friend A. Crane was in Europe a couple years ago, and decided to try something new…

I went for a stroll in Amsterdam’s Red Light District in search of a little titillation. I was a man in my late 20’s and had been traveling solo in Europe for the past two months.

By this time it seemed that every woman I passed on the street was the most beautiful creature I’d ever laid eyes upon. That, combined with my essentially abstaining from sex for several months, plus the lack of privacy in which I might masturbate, was making me feel pent up, and I found myself toying with the heretofore unconsidered notion of hiring a prostitute.

I wandered until I found the notorious red light district. I remembered reading that the Oudekerk (old church) is surrounded by brothels, and those were the first I found.

Directly across the street from the old church was a row of windows with red lights above them. Behind each of these windows was an overweight woman, most of whom were of African descent. Now, I sometimes find myself attracted to black girls, but not as a rule, and I am almost never attracted to heavy-set women.

I shook my head as I passed the last window. “Is this what all the fuss is about? There’s hardly anyone around.”

Well, that must have been the Baltic Avenue of brothels, because after a little more wandering, I found Park Place, if not Boardwalk. Some of these girls were simply gorgeous, and most were damned sexy, AND scantily clad, adding to their allure. As I walked back to the hostel, I found myself quite hot and bothered indeed.

I now found myself with two dilemmas. Should I get high in Amsterdam? And should I pay a woman cash for sex? Let’s consider the second question first.


My Big Adventure! Seattle and Alaska

By Kendra Holliday | June 26, 2015

Going places!

Going places!

I’m BACK! It’s so good to be home! And ready to start a new chapter! Boy, do I have plans for you! Let me know if you have plans for ME!

I’m now available for consulting and surrogacy sessions during the day, evenings, and weekends – when I’m not planning amazing events, making dreams come true, or organizing new religions, ha! More on that soon…

We started our summer off right with four days in Seattle, and six in Alaska – both places new to me! I love exploring new things.

And now I get to cross two more states off my list – I have 17 more to go!

In Seattle, we stayed within walking distance of the Space Needle.

Space Needle!

Space Needle!

I went to Archie McPhee! And got my daughter all kinds of goodies, including Fortune Teller Cards and an Emergency Self-Esteem Kit.

On a friend’s recommendation, we ate at Shiro’s Sushi and had geoduck – do you know what a geoduck looks like? Giant, muscular phallic clam. It was chewy goodness!

Try some geoduck!

Try some geoduck!

We also saw a pretty femalesque clam at the Seattle Aquarium:

Pretty clam

Pretty clam

We went bar hopping, and ended up at Pony, a gay dive bar:

Pony, gay dive bar!

Pony, gay dive bar!

And he surprised me with a Speakeasy!

Yes I'm easy!

Yes I’m easy!


The Father, The Son, and The Wholly Man

By Matthew | June 21, 2015

“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.


I Quit My Day Job

By Kendra Holliday | June 7, 2015

Queen of my Life!

Queen of my Life!

For the past four years, I’ve been working a day job and scheduling consultations in the evenings and on the weekends. I also have a daughter and organize events for Sex Positive St. Louis.

This packed schedule meant I had no time for myself, and hardly any time to spend with friends and lovers.

As an introvert, this got to be stressful. I wanted to do it all!

Whenever anyone would ask to make plans, I’d gasp, “I’m so busy!”

Well, that is changing NOW. Here on out, I’m replacing the phrase, “I’m so busy!” with, “I’m so fulfilled!”

Something had to give, and that something was my day job.

I remember how grateful I was to get that job – I was going through a really hard time. They gave me a chance. I appreciated that they respected my personal life and knew I would keep it separate from my professional time there.

The work was interesting and offered a steady paycheck and health insurance, but office politics and other petty matters were wearing me down. My most productive hours were spent pushing papers and sitting on my butt. I want MORE out of life than that! I felt like I had outgrown my role there.

After months of contemplation and discussion with my partner Matthew, I decided to push past the fear and take the leap – heart racing, I put in my notice.

I did it for my health, and to be more available to my daughter. I also did it for the sake of my passion and mission.

Have you ever heard that phrase, “Better to live hand-to-mouth than 9 to 5”? It means it’s better to release yourself to the wild than remain in a self-imposed cage. And you know what my motto is:



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