Planned Threesome

You're going to have to click to get all the details.

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The Artist

In California, I hooked up with this artist guy who collected skulls.

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Spontaneous Threesome

We had a date planned with her in a few days, but simply could not wait!

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5 Hardcore Relationship Exercises

You better be brave if you want great relationships!

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First Poly Date Success Story!

She was curious about poly. He was happy to show her how it works.

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2-4-6-8, We Love to Masturbate!

When is the last time you pleasured yourself? I did this morning!

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Is There A Step Between Monogamy and Non-Monogamy?

By Kendra Holliday | April 23, 2014 at 5:30 am

Dear Kendra,

I’m at a place where I’m trying to figure out my true desire. Is there something like a step in between monogamy and non-monogamy? I tried both in the past (mono and poly), and both have advantages and disadvantages.

I like the freedom in poly, because it allows me to be more myself. Although I wonder if I need that freedom… I discovered some shallow drives behind that, so maybe I’m past that phase? I like that poly challenges me to grow as human being. I enjoy the intimacy and the different connections you can have with different people.

Although I don’t like that it is so much work! In mono I have to say I like the easiness that goes with it… you just “belong” to each other; the rules and expectations are firm. I also like the intimacy in mono, which is of a different quality than what I’ve found in poly.

I agree strongly with being honest with yourself and going for what you truly want, in relationships, and more so, in ALL aspects of your life. Not an easy thing to put into practice, by any means, but to walk down a path with strength and conviction, one should first know which path IS the right one for you. And there lies my question: how do you know?

My reply:

At first glance, I thought your question was akin to the concept of being “a little bit pregnant” – either you are or you aren’t monogamous.

But of course like everything else, there is a spectrum. (Have you ever heard of that Hollywood Free Pass Rule married monogamous couples often have, where they’re allowed one celebrity they can fuck if given the opportunity? Because they know deep down they harbor desires like that, and they figure it’s a safe game to play because it would never come true in a million years? Wouldn’t it be awesome if someone really got the chance to exercise their free pass? That would make a great TV show, talk about drama!)

On one end of the spectrum is monogamy – only being with one other partner. The other end is constantly being with multiple partners. (Where does serial monogamy fit on the spectrum?) But what about being monogamous for the most part, but realizing that every once in a while, over the course of several years, you will encounter someone you want to be with and want to go for it without sacrificing your wonderful relationship?

I love my fluid relationship as it is right now, where we’re dipping in and out of casual and more intimate encounters with friends and lovers on a pretty regular basis, but I could easily be in a relationship that was 90% monogamous, meaning I would be okay with only rarely getting with another person. I could NOT be in a relationship that was 100% monogamous. I need to exercise my right to be a human who craves novelty and unique experiences.

There are rules you could add on to your traditional relationship that would give you some wiggle room – you can only be with someone of the same gender, or only once in a blue moon, or your partner must be present, or only when you’re out of town on business, or only if you’re in Amsterdam, or only when your partner is in a coma – whatever setup works that doesn’t trigger mass destruction and the end of the world. I suggest you look into the books Opening Up, The Ethical Slut, and Sex at Dawn.

Are any of you readers monogamous-but-not, aka monogomish? How’s it working for you?

The Artist

By Kendra Holliday | April 12, 2014 at 8:07 am

The Artist looked like Jon Snow. (Photo from GQ)

The Artist looked like Jon Snow. (Photo from GQ)

When I was in California, I got inspired to do a freaked out photo shoot, so I asked my friend if she knew any photographers in town I could collaborate with.

“Actually, I do!” she said, and within moments I was connected to a local photographer/artist. I told him what I had in mind, and he didn’t bat an eye.

I showed up at his swank, art-filled house the next day, and was glad to discover that not only was he open-minded, but also sexy and cool. As in, hot. He looked like Jon Snow from Game of Thrones.

He was grubby from a day’s work – he wore a wifebeater under a shirt and some ripped up, paint stained jeans. His voice was gentle, his gaze unassuming.

I shook his hand, then asked with a gleam in my eye, “So how freaky can you get?”

Without flinching, he shot back, “How freaky can YOU get?

Freak showdown! YESSSS.

Then he showed me his human skull collection. WTF??? He even has an infant skull. I held it – it was weightless, like a puff pastry shell. He had a human leg in one of his closets, not to mention other various human bones lying around the house. Maybe they were the remains of previous models… ha ha.

He further impressed me by showing me a jar of his own semen that he collects and keeps on hand for painting impregnation, and then he wheeled out an antique dentist chair as I cheerfully stripped down in his backyard. He offered me the bear skull.


How Do I Conceive?

By Kendra Holliday | April 11, 2014 at 5:30 am

Dear Kendra,

I’ve been married to my wonderful husband for six years and we have a great house and great jobs. Life is great! There’s only one thing missing – we’ve been trying to have a baby for the past two years. Trying to get pregnant has almost become an obsession for me. It’s taken the fun out of sex. People give us all sorts of advice, from practical (recommending positions) to silly (place a rabbit figurine facing east in the bedroom). I hate to admit it, but I’m starting to get desperate. My gyno says things seem to be in working order. We’re saving up for invasive fertility treatments. I WANT A BABY! Why is it so hard??

My reply:

You know, I’ve had many obsessions in my life, and one of the most surprising ones to me was when I got obsessed with having a baby.

All my life I had no interest in breeding. As a kid, I remember shuddering with horror just thinking about childbirth. I saw my mom get ripped apart over and over – she was pregnant at least seven times, and the last birth, they yanked her bladder out with my baby sister. She’s had incontinence issues ever since.

Nevertheless, I fell in love with some guy and got hit by a maternal urge over pancakes, so we got married and decided to have a kid. We had been in a traditional vanilla monogamous relationship for over five years at that point.

I was shocked to discover that pregnancy was an elusive goal. I mean, what’s easier than throwing birth control out the window and fucking a lot? It took us two years and two rounds of Clomid, a fertility drug, to finally conceive our daughter. It got to the point where we dreaded sex and he resented me for pestering him for sperm deposits.


The #1 Way to Please Your Man: How to Give an Extraordinary Blowjob

By Kendra Holliday | April 5, 2014 at 5:15 am

I blow, therefore I am Goddess.


Oral sex is the #1 way to send your man into ecstasy. It feels incredible and few men can resist the opportunity for their cock to be worshipped and loved. Best of all, his deep gratitude is bound to pay off considerably later on when he eagerly returns the favor. Here is a breakdown on how to give a great blowjob, TBK style.

Great conversation topic

Before you put your mouth to good use, ask him what he likes so you know what to lay on thick and what to avoid. Does he like his balls licked? Teeth? Lots of suction? Strong head stimulation? Slow or fast? You can have this conversation over dinner or while sitting on the couch watching TV, but be prepared to stop what you are doing so you can practice. OR employ tech foreplay and do it over IM or text during the day so you can prime his pump for when you see each other that evening.

Tease him

Take the tease trail. For example, start by kissing your most fortunate test subject, then slowly head south, kissing and licking his nipples, chest, belly, thighs, balls, shaft, then finally make your way to his cock head.

Once you’re there, open your damn mouth. I keep hearing from both men and women about these women with small mouths who can’t get the job done. Despite what you might think, my mouth isn’t that big, and I can stuff something substantial in it. Though I can’t fit a soda can in it like I saw one woman do. That’s impressive. If you have TMJ/jaw issues, do the best you can and supplement with edible lube/hands.


The Bald Truth: Preying on Male Insecurity

By Kendra Holliday | April 1, 2014 at 3:45 am

Sexy bald man

I used to date a guy who took Propecia every day for years because he was terrified of balding.

I think he was worried he’d end up like Larry David, the bald asshole. He was already cultivating the really annoying personality. I wish he could have taken a pill for THAT!

He’d chide me for wearing makeup, for the shoes I wore, and was against vanity and materialism, so he was pretty embarrassed that he felt so compelled to take a pill to prevent balding. I’m glad he was aware of his hypocrisy – most people are not.

Luckily, he didn’t have any of the nasty side effects like current studies are trumpeting – erectile dysfunction, premature ejaculation, low libido. For the sake of his wife, I hope he’s still side-effect free, as they say the issues can be long-term.

Did you know there’s a website and hair loss radio show called The Bald Truth? It features stories such as:

Accidently Reversing Baldness in Mice Might Lead To Cure for Humans

Pick Up Artist Wayne Elise Advises Hair Loss Sufferers On Meeting Women

Beyond Facebook: The Future of Social Networking For The Hair Transplant Community Is Here

Apparently, there are a lot of men out there who are freaking out about their receding hairline. Is this as big an issue for men as breast size is for women?

The show’s host is Spencer David Kobren. He “is the Founder and President of the American Hair Loss Association, the nation’s foremost 501 c 3, non-profit organization dedicated to educating the public, healthcare professionals, and the mainstream media about the emotionally devastating, and life altering disease of hair loss.”

Life altering, yes, but a disease? I just don’t see what the big deal is about balding. I said that to my friend whose hair is thinning, and his reponse was, “OK Kendra, close your eyes. Now imagine YOU ARE BALDING.”


5 Hardcore Relationship Exercises

By Kendra Holliday | March 28, 2014 at 7:18 pm

David Wraith and me

David Wraith and me

Want a better sex life? Then start communicating better! Push past your comfort levels, people, and communicate FOR REAL.

Open, and honest. You gotta be vulnerable.

Here are some bold ideas to get the ball rolling (pick the right time and place to do these! Carve out some quality time, don’t attempt to knock it out on the way somewhere, unless it’s a road trip):

1. Institute relationship check-ins. Do as often as needed – daily, weekly, monthly… My partner and I do it about twice a year, when our schedules are especially stressful and it’s a challenge getting our physical and emotional needs met.

Have you heard of Daily Temperature Readings? It’s a concept that allows you to explore the following key points:


*New Information


*Complaints with recommendations

*Wishes, hope and dreams

Covering these points can help you find out if you’re on the same page, or even reading the same book!

2. Tell each other three things you don’t like about each other (or five, if you’ve known each other for more than two years. :)


In Praise of Hairy Underarms

By Kendra Holliday | March 24, 2014 at 5:30 am

I love my hairy underarms!

I love my hairy underarms. They’re like having two more pussies. Most days I’d rather have my underarms caressed than my nipples tweaked.

My body odor has been better since I stopped shaving under my arms. Interestingly, my partner Matthew’s underarms are almost completely hairless and he never has B.O.

Do you know any women who don’t shave under their arms? (I like the word “underarm” better than “armpit.”) Furry Girl and Sequoia Redd come to mind, but I keep discovering more and more women who flaunt their feminine fur with pride!

I’ve been experimenting with my YouTube channel, and was surprised that the clip that has received the biggest response was the one about my hairy underarms.

Here is one message I got from a huge hairy fan:


2-4-6-8, We Love to Masturbate!

By Kendra Holliday | March 16, 2014 at 1:20 pm

This post is an ode to masturbation! Masturbation is completely healthy and normal. Masturbation is a way of being in touch with your body. Masturbation is good for circulation and mood, as well as long-term sexual health. Masturbation is a safer sex practice!

There is nothing to be ashamed or guilty when it comes to masturbation.

Unfortunately, many people have religious or parental experiences growing up that negatively impact their sexuality. Take this instance from CapitalFun1:

For a long time I had carried great shame with masturbation and I experience strong feelings of self-loathing upon completion.  I equated it to being dirty, and I should be punished for it.  I connect this feeling to my youth when my mother came into my room as I had just finished masturbating, my pants at my knees.  I remember thanking god I had rolled off the side of my bed and threw my back-pack onto the bed in time and told her was looking for notes to help help me with my homework.  Upon seeing the wet-spot on my bed, I remember witnessing her put her finger in it and then smell it followed by a look of disappointment. This completely filled me with embarrassment and horror which  subconsciously hold to this day.


Let’s Play the Obscene Nipple Game!

By Kendra Holliday | March 15, 2014 at 7:00 am

Can you guess which nipples are allowed to be seen in public, posted on facebook, and are socially acceptable? Which nipples are to be feared and reviled? Which nipples should be jailed and punished by law? You be the judge! (All photos are from Wikimedia Commons unless otherwise noted).

Tip: Here is the definition of the word “obscene”:

1.offensive to morality or decency; indecent; depraved.
2.causing uncontrolled sexual desire.
3.abominable; disgusting; repulsive.

Here we go! First, let’s warm up with some very SFW (Safe For Work) pics of human mammals:

This is a woman from Afghanistan. Is this obscene?

This is a Victorian woman and man. Is this obscene?

This is a statue. Is this obscene?



By Kendra Holliday | March 10, 2014 at 6:51 pm

I’ve reached my ideal relationship goal.

A few years ago, when my partner would go on a date, I would lie in bed, heart pounding, unable to sleep until he called me when the date was over. I would imagine all kinds of scenarios, some hot, some scary, and would anxiously hold my breath as he recounted details of the date. As the story would flesh out, I would cautiously relax, but still be slightly wary.

Time and again, after each of these encounters, he would make me feel special and secure in our relationship. I also grew accustomed to the strange sensations.

Nowadays, I can sleep fine when he’s out on a date. I don’t have to be on a date myself, I can be doing my own thing, hanging with my daughter or a friend, or enjoying some alone time. This is a big accomplishment!

Whenever I start to feel jealousy or possessiveness creep in, I remind myself that my partner is not an object. I can’t put him in a closet when I’m not with him. He deserves as much happiness and exploration as I desire for myself.

Here is an example.

Last weekend, I took my daughter on a retreat four hours north of St. Louis. We spent the time frolicking in a tiny village, creating art, making music and friends.

Meanwhile, my partner had a date scheduled with a new woman, someone we both knew. She was in transition and wanted to find out what polyamory was all about. She approached us about it, asking how it all works. She came to the right people.

With her last boyfriend, she told him she was okay with him being with other women, as long as he let her know about it. Unfortunately, he couldn’t handle being truthful and cheated on her, despite her generous offer!

She knew she deserved better than that, so she decided to make the most of her fresh start.

They had their date. It went from 6pm until 10am that morning – EPIC!


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