Category Archives: Relationships

My Top Sex-Positive Recommendations

By Kendra Holliday | July 30, 2019

Kendra Holliday will help you work the kinks out!

I offer sex and relationship consulting, and I’m happy to say that I’ve been getting more women, LGBT folks, and couples these days. Historically, most of the people who have sought me out for my unique services have been men who crave female energy.

The Top 5 reasons why people contact me are, in this order:

1. He’s a married man in his 50’s or 60’s whose wife is not interested in sex (mismatched libido)

2. He/she/they have some sort of sexual issue they want to work through, such as inexperience, anxiety, or orgasm/penis problems (Erectile Dysfunction is a common complaint – it can get complex when you heap social conditioning and anxiety on top of the natural aging process.)

3. He/she/they are interested in branching out sexually, either because they are in transition, not getting laid, or curious about alternative lifestyle options (non-monogamy, BDSM, sex work, etc.)

4. He has a fetish and is ashamed/seeking an outlet

5. They want to meet me, and possibly rub me for good luck

———

My goal is to offer tools, connections, and non-traditional options so that the people seeking me out can reach their goal of becoming happier and healthier. My approach is unconventional, and I get referrals from licensed sex therapists. I’m pretty well connected and have a strong network. Sex is my specialty, which ties into work, family, personal – everything!

Here is a list of resources I most often recommend to my clients:

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A Polyamorous Formula That Works

By Kendra Holliday | July 23, 2019

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 eleven 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.

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5 Hardcore Relationship Exercises

By Kendra Holliday | June 13, 2019

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:

*Appreciation

*New Information

*Puzzles

*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. 🙂

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I Dated A Charming, Popular Sex Predator

By Kendra Holliday | May 3, 2019

OJ Simpson and his late wife, Nicole – a celebrity example of a charming, popular guy that is, ahem, problematic

Ed Note: This guest post by Lynn Beisner was originally published on RoleReboot. Lynn warns women to always trust their gut. Sometimes the guys we label as “creepy” aren’t sexual predators, they’re just insecure. In her experience, it’s the charming, popular guys who can be the most dangerous.

The recent discussion about creeps has been both encouraging and concerning for me. I am encouraged because I believe that we as women should give ourselves permission to avoid any person or situation for no reason other than that it feels wrong. I also am of the strong opinion that we as women have a duty to warn each other about potentially dangerous situations, which is what we are trying to do when we label a man as a creep. But using the label of creep as a way of warning our fellow women also causes me concern. I worry that we are confusing or conflating creeps with sexual predators. They are two very different creatures and what protects us from one does not protect us from the other.

I can explain the difference best by telling you about two men I have dated. Let me start by telling you about the sexual predator; I call him Mr. Popularity because he was one of the most well-liked men that I have ever known. We worked in the same office high-rise, and it seemed like anywhere on those 32 floors that we went, people knew and liked Mr. Popularity.

When we started dating, I became instantly and bizarrely more popular; it was as if my geekiness was cancelled out by my association with Mr. Popularity. Women suddenly wanted to talk to me—mostly about Mr. Popularity. He had dated other women in our building, and some of them struck up conversations, telling me how much fun they had with Mr. Popularity. One comment that was repeated by every woman was how much he had expanded their sexual boundaries. I suddenly seemed to show up on men’s radar as well once I started dating Mr. Popularity. Many would tell me something along the lines of: “You’ll have a lot of fun dating Mr. Popularity. He is a great guy. But you know that he never gets serious about anyone, right?” Then they would give me their phone numbers for when Mr. Popularity and I stopped dating.

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How Do I Exercise My Open Marriage?

By Kendra Holliday | March 23, 2019

Dear Kendra,

My wife and I recently decided to open our marriage. Unfortunately, I’ve run into a problem: women don’t seem to want to get involved with a man who is in an open marriage.

So far the three women who I’ve approached, although they admit being attracted to me and interested in the idea, have all given me some variation on the same objection: they’re worried about hurting my wife or causing harm to our relationship. These women know both my wife and me, and they aren’t willing to even acknowledge the possibility that talking to my wife could resolve their concerns.

I can’t help but find this fairly insulting. These women seem to be substituting their own judgment for mine and my wife’s, and telling us that, as much as we might think we’re ready for an open relationship, we will inevitably fall victim to jealousy and bitterness.

Now, I can understand that some women may not want to take any risk of being responsible for that, no matter what the people in the relationship might say, and maybe there’s nothing I can do to change those women’s minds.

But how can I best explain that they don’t have to worry about causing harm to our relationship—and that even if that happened, it wouldn’t be their fault—and how can I maximize the chances that they’ll overcome their feelings of unease and be willing to get involved?

My reply:

I asked a couple successful poly guy friends of mine for their 2 cents, and their combined answers added up to at least 2 bucks! Here is J’s take:

“Why not approach women who already identify as poly themselves and have other already established relationships? You can join a poly group in your town and mingle with like-minded people.

Of course I realize that’s a tough pill to swallow when you’ve already got what seems like three perfectly willing takers–if only it weren’t for their warped view of his wife, the mutual understandings they may have in their relationship …or what, on principle the sanctity of his marriage to her? Yeah, honestly I’d feel somewhat insulted by these assumptions of overreaching responsibility and risk too.

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A Date With a Gentleman

By Kendra Holliday | July 7, 2018

(This is not a pic of him, but of some random gentleman)

So, we’ve been dating this sweet ‘n sexy couple for the past year or so.

It’s been very slow going because we’re all so busy. We finally realized we had to carve out time with each other in order to have special dates, so one week I went out with the husband, and Matthew had a date with the wife a couple nights later.

Let me tell you about my date first – he was such a gentleman!

I wore a pretty, silky jade dress. I felt a little nervous! I was excited to finally have a chance to talk and bond with him in an intimate manner. We had sex once before, months ago, but it was a totally different feel – anonymous and clandestine, with no words exchanged. So even though I had a sneak preview of his prowess, tonight felt brand new.

He came to my door and knocked, presenting me with a bottle of wine and a bouquet of lettuce greens from his garden! He complimented me on my dress and opened the car door for me.

We went to The Fountain on Locust for drinks and dinner. He knew right where he was going, and I didn’t have to worry about a thing!

This was our first chance to enjoy one-on-one quality time with each other. He made me feel so special. I was in a delicate, feminine mood that night. He asked me questions and listened thoughtfully as I babbled away about all kinds of things. He had such a confident, gentle demeanor.

The Fountain served us AMAZING ice cream martinis, which we kept sampling throughout dinner. Our server was amazing and added some electric energy to the atmosphere. His intensity made me blush when he took our drink orders. I love the decor, too – all blue and gold, art deco.

When we got back to my place, he went to pour two glasses of wine for us. When he returned, he found me wearing only lingerie – I couldn’t wait to slip my dress off!

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The Father, The Son, and The Wholly Man

By Matthew | June 17, 2018

“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.

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Advice from Seasoned Polyfolk

By Kendra Holliday | April 21, 2018

Get it?!?!

This is a follow-up to the wonderful guest post I shared the other day from a woman new to polyamory struggling with her illogical, runaway emotions.

I’ve been there. See?

Things you should know when you’re new to polyamory:

It gets better.

Every person experimenting with poly who has contacted me in the middle of their biggest freakout reports back to me a week or two later that things are much better, and that the experience has brought them closer to their partner or others. That’s what polyamory is all about – connecting with others in ways that feel right to YOU.

The rigid rules of traditional society don’t work for a lot of people. It takes courage to try a different path. You may feel like your friends don’t understand, and afraid of what your family might think.

REPLACE THE FEAR WITH LOVE.

Imagine how Lewis and Clark felt as they blindly navigated their way out West. They forged the way for others, and now, we have San Francisco. OK, now imagine Lewis and Clark at Folsom Street Fair

TANGENT! (sorry, back on topic)

Sometimes – but not always – you’re not partnered with the right people. Just like other relationships (monogamy, work, family), the problem might be the dynamic. Don’t be so quick to blame polyamory OR yourself.

I feel like a poly pro, but I’ve been doing it for 10 years. Think about where you will be in 10 years. As for me, 10 years ago I was a nervous wreck; whether I was driving to dates or staying home while my partner was out with someone else, my stomach was in knots – NOT a very sexy feeling.

Advice from a woman who’s been doing it for more than three years and used to have jealous freakouts galore:

“My biggest advice would be this. Don’t ever try to feel NOT jealous. Feel it. Feel it deeply and express it. And then understand that your jealousy is not a call for your partner to change their behavior. One of the men I am dating never gets jealous, so I spent a lot of time hiding my own feelings from him in our early days. Another man I’m dating gets more jealous than me, but has learned to deal. I still get jealous, but it comes and then quickly leaves.”

Other gems:

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Married and Missing Something

By Kendra Holliday | April 12, 2018

Reading is sexy!

The other day a friend asked me, “As a sex worker, do you require married clients to have consent from their wives to see you?”

I replied, “Ha, no.”

You see, most of my clients are married men.

I practice ethical non-monogamy, but what they do is on them.

When they come to see me, I provide them with options, and then they can decide what is best for their situation. (See Dan Savage’s take on how cheating can be the lesser of two evils.)

Most of the married men I see LOVE their wives and feel intense loyalty and desire and want to remain married to them,

BUT

their wife has cut them off sex. 🙁

Oftentimes, the woman has two kids, fulfills her biological imperative, is battered by religious and social norms, hits menopause, and shuts sex down and assumes, due to lack of communication, that her unilateral decision is to be imposed on her husband, too.

Resentment builds on both sides.

Sexy mature me

SO many men complain that they have to initiate sex all the time. They don’t understand the difference between spontaneous desire (80% of men) and responsive desire (80% of women).

Due to higher levels of testosterone, most men wake up horny and walk around horny all day, and if they don’t scratch that itch, they go to sleep frustrated and horny, whereas most women need an erotic prompt to get horny, and the way men attempt to activate a woman is….not always effective. In fact, it can create the opposite effect and repel the woman.

On top of that, women won’t get naked in front of their partners because of body image issues. And they resist cuddling or touching, because that might lead to UGH sex, which is more like a chore than a reward.

It’s hard to be intimate when you cut off physical and emotional contact.

Sure men hire sex workers because they want to get blowjobs and fuck and cum,

BUT

ultimately, they want to bask in female energy and be accepted.

Female energy is PRICELESS.

It’s a sad, trapped cage we find ourselves in.

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Basking in the glow of male energy

Basking in the glow of male energy

The book King, Warrior, Magician, Lover: Rediscovering the Archetypes of the Mature Masculine explores the archetypes of the mature masculine. Men who act out, have temper tantrums or are violent – jerks, bullies, know-it-alls and thugs – haven’t reached their full potential.

Men aren’t allowed to fully mature in our society. There is no rite of passage. The spoiled little princes of the world have work to do if they aspire to be superior men – if they want to be King.

The author Robert Moore is a psychologist in Chicago, IL. You can read more about his theories and discoveries here.

So how do you become King? Here is the book that perfectly mirrors our relationship dynamic: The Way of the Superior Man by David Deida. I underlined the shit out of this book. There’s no way I can feature all the awesome points, so please get a copy for yourself if you’re interested in tapping in to what makes our relationship so explosively orgasmic and fulfilling.

My partner Matthew hasn’t read the book, but that’s ok – he’s living it.

Here’s the premise. In order to have a passionate relationship with someone, you need to adopt a feminine and masculine contrast. It doesn’t matter who possesses the masculine or feminine – you can be a masculine female/feminine male couple, or a masculine female/feminine female couple, etc. The author maintains that 80% of people lean one way or the other – they either want to be ravished or do the ravishing.

For the most part, Matthew does the ravishing and I greatly enjoy it, I soak it up like a slutty sponge. But every once in a while, we’ll turn the tables and I’ll ravish HIM, which is just as fun and exciting. If neither of us assumed the ravishing mode, things would be more even keel. And boring.

That’s what happens in so many relationships – after the thrill of new relationship energy dies down, we get lazy and slip out of Lover role and become Managers, Caregivers, and Roommates. Then we take our partner for granted and lose respect for them and the sex turns lukewarm and resentment sets in.

So many men complain to me about how their wife doesn’t want to have sex with them, which makes him feel hurt and rejected. The reason the wife is cold to him is because she doesn’t respect him. The reason she doesn’t respect him is because he has let her down.

David acknowledges that most men want to have sex with other women, even if they are in a sexually fulfilling relationship. He advises, “If you want to be with other women, make sure you are taking care of the woman you have.”

Check his stuff out on YouTube – here is an example:

This is one of the books I recommend most. Click here to view my list of Top Sex-Positive Recommendations.

Bonus link: The Art of Manliness

New to Polyamory: Have You Been Here?

By Kendra Holliday | April 6, 2018

Temporarily, anyway.

Ed  Note: I’ve had many woman exploring polyamory contact me lately expressing their gut-wrenching emotions surrounding sharing their partner. I asked one permission to share her story with others, as it will no doubt comfort those going through the same thing.

I started reading about polyamory a couple of years ago. It started out of curiosity, but on the backdrop of “Oh, I could never do that.”

As that backdrop fell away, I found that this kind of lifestyle made more and more sense to me. I’d never had a long term relationship, and the idea of appreciating connections on all levels really appealed to me.

I decided to try it out. I joined OKCupid, and I went on dates with a couple of guys who were in open marriages…nothing really panned out there. Then I exchanged messages with someone who was smart, interesting, and poly.

On our first date (in a coffee shop), we ended up talking for over two hours. We hit it off immediately, plus I found him incredibly attractive. There was a point in the date where we both looked at each other and seemed to both think, “This is going really well!”

We started seeing each other regularly. The sex was (is) mind-blowing. So was (is) our mental connection. Slowly and organically we realized: holy fuck, we’re in love.

We became a “couple”. We aren’t out as non-monogamous to many  people. Some of my friends know–they’ve known I identified as non-mono even before I met him–but discussing my relationship with my mono friends has proved…troubling. I have tried to cultivate more poly friends as resources, and the online communities have certainly been helpful.

He has had a lot more experience with polyamory than I have. As I grew closer with him, I started getting nervous because…he was still going out on dates and I didn’t want to. He was still having sex with play partners from his past, while I found myself turned off to my previous play partners. Sex with an intense emotional connection was the only kind of sex I craved, and these previous partners and I did not have that.
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Love Like an Ocean: Diving Deep into Polyamory

By Kendra Holliday | January 10, 2018

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 ten 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.

Sorry for bragging, but…

We don’t fight. We have amazing chemistry and enjoy an incredibly satisfying sex life. We have matching libidos and desire. 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.

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Arousal: The Secret Logic of Sexual Fantasies

By Kendra Holliday | December 29, 2017

Arousal: The Secret Logic of Sexual Fantasies, by Dr. Michael J. Bader

I’ve had the book Arousal: The Secret Logic of Sexual Fantasies on my shelf for a long time. It tempted me with its mysterious title and sexy cover (I LOVE oysters, and I LOVE my pearl, if you know what I mean).

Well, I finally dusted it off and read it, and it blew my mind, and I’ve been recommending it to people left and right ever since.

Here’s an intro concept from it that should provoke your thoughts:

“There’s a joke that says that when two people have sex, there are six people in bed: the two lovers and the parents of each of them.”

Is that creepy, true, or both? I hope you’re imagining group sex with your parents right now.

A sampling of the MANY interesting points brought up in this book:

– “Sexual excitement requires that we momentarily become selfish. There needs to be a tension between selfishness and caring, between using and pleasing your partner.”

Do you know what this means? Sometimes, when it comes to sex, you need to be ruthless. You need to let go and stop worrying so much about every little move and just focus on the pleasure. YOUR pleasure.

– The difference between guilt and shame: “Guilt involves beliefs that we are hurting others, while shame involves beliefs that we’re exposed and unworthy in the eyes of others.”

– “When people are aggressive or cruel in their sexual daydreams or practices, it is not because they are primarily sadistic but because they are trying to solve a problem.”

– Have you ever known a woman who is really bitchy toward her male partner? He’s such a nice guy, he tries so hard to cater to her wants and needs, yet she treats him like an annoying puppy? This book explains the reason behind that lopsided dynamic.

– Survivor guilt and unconscious parental jealousy is behind a lot of the issues we face with our parents. Have you ever wondered why someone would start drinking heavily when they became successful in their field? Or why some parents sabotage their kids and excessively criticize instead of support them in their endeavors? This book goes into the details behind those perplexing behaviors, and much more.

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Planned Threesome

By Kendra Holliday | December 23, 2017

After our spontaneous threesome the other night, I was SO eager for the three of us to get together again! I’m so greedy! I want more more MORE!

Lana came over, and we sat on the back porch and talked over cocktails, relaxing and catching up.

After a while, he asked her if she was down to play that night, and she said yes!

I love her hazel eyes, her bountiful hair, and pert nose. I’m a sucker for pert noses! She has such animated facial expressions, and tells such funny stories. I love her mannerisms. Very mischievous eyes. Also, she has an extremely smooth butt. It’s like really cute butter.

This time, he drew a bubble bath for two! We both easily fit in the tub. He gave us our girl time to sit and talk. He checked in on us, brought us drinks, it was wonderful!

Then we sat on the couch for a while to cool down, the two of us naked with towels.

He led us up to the bedroom, which was bathed in the golden glow of a small, bedside lamp. The king-size bed was adorned with chocolate brown sheets. Mood music played softly in the background.

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Spontaneous Threesome

By Kendra Holliday | December 22, 2017

Continued from previous post

Me getting spanked by Matthew! Photo by Mike Estes

We arrived at Hustler’s Taboo night.

Thankfully, we were mature enough not to let anything interfere with our great evening, which is a good thing, because it got better every second…

Taboo was crowded and full of activity. They have quite a bit of equipment – a rope suspension section, couches, spanking benches, St. Andrews Crosses. All were in use, but soon a spanking bench opened up, and we seized it.

I went first so she could watch and get used to the energy of the place. She had some BDSM experience, but nothing public.

I eagerly bent over the bench. I was wearing a sexy little business top and skirt. The skirt hem was asymmetrical, so when I walked or bent over, you could see where my lace stockings met my pale thighs.

He worked me over, grabbing my hair, spanking me, lavishing me with good, hard attention.

I got hot and ripped off my top and bra. Lana glanced around surprised. They allow nudity here!

It was so stimulating and exhilarating! I kept laughing and giggling.

He pinned my arms behind my back and instructed Lana to tend to my top as he tended to my bottom. This guy parked himself right in front of me and stared hard. Not a problem, but he was a little too close for our comfort, so Lana stood at my head, providing a barrier between us. I’m sure he didn’t mind her ass in his face.

We were buzzed and happy.

Next, it was her turn. She had been smacked on the ass during sex, but never had a spanking like this.

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