By Kendra Holliday | April 13, 2022
Category Archives: Relationships
A few years ago, I attended Woodhull Sexual Freedom Summit in the Washington, D.C. area. Several authors were featured, including Elizabeth Anne Wood, Ph.D. She read an excerpt from her book, Bound: A Daughter, a Domme, and an End-of-Life Story.
I was instantly intrigued, as I’m a bit obsessed with sex and death – I’m both horny AND morbid. I had never heard of a story like this – a daughter being supportive of her mom’s kinky sex life?! Come again?
I’d like to say I couldn’t wait to read it, but it turns out I DID wait to read it – when I got home, I put it on my shelf of sex books and there it sat, for months. So many books, so little time.
But I finally had more time to catch up on my reading, thanks to a serious mental breakdown I had in February. I took time off from seeing clients (I’m a sex worker who does Pro Domme, fetish and surrogate work), and was able to tend to myself.
I’m glad I read it when I did – it was published just a few weeks before my own mom died in 2019, which allowed me to relate to what the author shared so much more.
By Kendra Holliday | April 9, 2022
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, adult virginity, anxiety, trauma, disabilities, or orgasm/genital 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, in between relationships, single/divorced/widowed, not getting laid, or curious about alternative lifestyle options (non-monogamy, kink/BDSM, sex work, etc.)
4. He has a fetish and is ashamed/seeking understanding and validation (“Am I normal?!”) or 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:
By Kendra Holliday | January 5, 2022
(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 thirteen 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:
3. Our relationship
4. The people we are dating/close relationships
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.
By Kendra Holliday | June 15, 2021
Below is a list of relationship value items. Which ones are important to you? Are you getting your emotional and physical needs met? What about your partner(s)?
Acts of service
Feeling heard. Do they listen? If they get distracted, do they follow up with what you were saying?
Willingness to compromise
Partner enjoys spending quality time with your loved ones/chosen family
Supporting each other’s personal growth/mission: reading what you write, listening to your music, your podcasts, supporting your continuing ed
Versatility within sex life
Sex with different people
By Kendra Holliday | June 3, 2021
My man likes the sexy dresses, fishnet stockings and all that, but what he loves most is the casual, natural look.
Jeans and a tank top, no bra:
Stripped down just a little bit more:
These boy shorts say: life . energy . intelligence
What attire do you find sexiest?
By Matthew | June 21, 2020
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.
By Kendra Holliday | May 6, 2020
The other day, I asked my friends for advice on how to deal with all the men who contact me looking for sex. I told them:
Since I’m so out there as a sex-positive activist and everyone knows I’m in touch with my sexuality, I get a lot of man contacting me requesting female energy/sex. I tell them that is a service I offer. With some of them, they are agreeable to my way of doing things, but others can’t or don’t want to pay for intimacy services, which is totally cool. It means we want different things, and they can go look somewhere else.
But here’s where it gets tricky. Some move on, but some dig in and ask me for a bunch of free dating advice (I offer consults as a service as well), or, even worse, they plead with me to help them find women to have sex with for free. This baffles me – are they asking me how to date? Do they think I have a closet full of sexy women to go to and pull one out and give to them?
Men: How do you find women who want to have sex with you?
Women: Where are you? Why are you hiding? They can’t find you. Are you wanting to have sex with men? Are you picky, or will you get with almost anyone who asks?
I give them a couple quick suggestions and resources, and then usually I just have to stop replying to their messages.
To be clear, some of the men are entitled and lazy, but others have additional challenges such as anxiety, autism, disability, or social awkwardness.
Below, I’m going to share with you my suggestions, as well as advice from my friends. One female friend even wrote a guest post about it – you can read it here.
By Matthew | May 4, 2020
I love to flirt, and women seem to enjoy flirting back. The casual fun flirting is a blast, and I enjoy it. But I never know if they want to move from fun flirting to something more serious.
I’ve tried a few times to make the change to serious flirting, and found out I was wrong, and screwed up friendships. So for the past few years, I just automatically default to “it’s just for fun” and don’t even try to “make a move.”
So I guess what I’m asking is – is there any good indication that a woman is interested in moving the flirting from “just for fun” to something with more intent? What Are Best Practices for Men Flirting With Women?
I’m going to turn this one over to Matthew! Now, this is a man who is not into tricking or manipulating other people.
He takes “master pickup artists” and picks them up and tosses them in the dumpster.
He practices open and honest communication.
He doesn’t have a GQ model body, but he has the confidence of Zeus.
He realizes that not every woman wants to be with him, and HE’S OK WITH THAT. He’s only interested in being with women who are genuinely into him. Somehow, he manages to play the situation so that he KNOWS the woman is desperate to get to his cock. At least, that’s how he played me. For months. The bastard! Sigh, I’m hooked.
Take it away, Matthew….
This is a great question and I am going to address it on a number of levels. Specifically to your question, first and foremost what comes to mind is an encounter I had with a woman some time ago.
By Kendra Holliday | February 4, 2020
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:
*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. 🙂
By Kendra Holliday | November 5, 2019
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.
By Kendra Holliday | October 20, 2019
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,
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.
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,
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.
By Kendra Holliday | May 3, 2019
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.
By Kendra Holliday | March 23, 2019
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?
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.
By Kendra Holliday | July 7, 2018
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!
By Kendra Holliday | April 21, 2018
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.”