How to Approach a Woman – Even if She is a Whore

By Kendra Holliday | May 27, 2020

Embrace your erotic side

I know this is going to sound silly coming from a sex worker, but I’ve finally figured out why I find eager, impatient men to be so off-putting.

I get so many men contacting me who want to go from zero to anal in less than an hour.

My whole mission as a sex surrogate is to teach people how to build intimacy and be a good partner, and guess what?

Building intimacy takes time.

I have an extremely reasonable process in place, but all too often I find myself being pushed along like meat on a conveyer belt, ready to be gobbled up, instead of savored.

A man will contact me, and he’ll get super excited when he finds out that I offer all kinds of sexual exploration experiences. He’ll want to do them ALL RIGHT AWAY.

But I’ve learned that I need time to build a relationship with someone, in order to feel comfortable and for things to be authentic. Otherwise, I feel like I’m forced into a performance, and it leaves me feeling yucky afterward, and a relationship that was initiated with such promise and potential becomes tainted, and I have to cut it off in order to protect myself.

Kendra Holliday portraying vanilla. Photo by Stan Strembicki

Here are my biggest turns offs:
Pushiness/eagerness
Impatience
Stinginess
Immaturity
Entitlement

Here’s what turns me ON:
Patience
Maturity
An attitude of gratitude
A generous spirit

I find that the most rewarding encounters I have are with clients who have allowed me to set the pace for building intimacy. I have amazing relationships with clients I’ve been seeing for years. We’ve made so many fantasies come true together!

Here is how to spoil things quickly:
Contact me
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Push boundaries
Disregard feelings and safety

Here is how to create a lasting relationship with me:
Contact me
Be respectful
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment

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No Shave May: Before & After Pics!

By Kendra Holliday | May 27, 2020

For about six weeks in 2012, which included the entire month of May, I did not shave anything on my body – legs, underarms, pubic area. (my recap video is here.)

This weekend, we had a shave party!

Let me show you the legs first. In this pic, I have one leg shaved – can you tell which one?

One of these legs is not like the other…

Let’s take a closer look:

Hairy leg closeup

I was glad to shave my calves – wearing skirts with hairy legs is fine. I loved feeling the breeze tickle the hair. But wearing pants or tights with hairy legs felt CREEPY and annoying.

Next, my crotch.

.

.

Just kidding.

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COVID Kendra?

By Kendra Holliday | May 19, 2020

Flirting with the Angel of Death…

Sigh…I would make the most beautiful vector. 💃😚

I’ve been keeping a list of people who have been wanting to share intimate space with me since mid-March, and it’s currently at 40 folks. These are just the ones who have been screened and verified! 😇🤓

Can you imagine if I went ahead and booked all of those sessions? Move over, Typhoid Mary – COVID Kendra would give you a run for your money! (Speaking of money, this is about ~$10,000 of income I’ve missed out on.) 💸

Typhoid Mary was famous for her peach ice cream – mine is over here melting! 🍨😝

It’s been super frustrating getting loads of inquiries from people who are seeking play parties, group sex, erotic encounters. I have to keep telling them now is not the right time to act on such fantasies.

Right now, we need to hunker down with our sexually creative and adventurous fantasies and come up with some future goals – beef up our “Fuck it List” (as opposed to Bucket List). And it pains me when someone who has been in contact with me for months or even years, emails me now, declaring that they are FINALLY ready to move forward with addressing their sexual issue. I’m sorry, but the timing is off.  It’s like being an unpaid DJ taking song requests from people wearing earplugs. And then when I offer them the option of meeting online, they inform me that they lack the funds, the privacy, etc. Stifling and frustrating for everyone involved!

My hands are tied…

I promised everyone I would get in touch with them when I’m ready to start seeing clients in person again, and gosh is that a mind-bending waiting game. The devil is in the details… 👺📝
What are the best resources for me with guidelines on how to keep my clients safe? I guess I need to research CDC guidelines for massage therapists.
For now, I’ll keep blowing you kisses from a safe distance!

You gotta blow hard

Earthworm Sex!

By Kendra Holliday | May 17, 2020

Guess what! My monogamy stint is officially OVER!

As mentioned in my COVID statement post, I’ve been monogamous with my partner of 12 years since mid-March. This is a big deal, because normally, I’m intimate with several people a month.

Earthworm sex!

Eventually, I’ll need to carefully venture back into the world of sharing physical space with others, and the best place to start is with my other partner, someone I’ve trusted for years. He’s been sheltering at his house, and hadn’t touched anyone for weeks. He even had an antibody test, which came back negative.

We decided on turning our reconnection into a fun experiment. We started by sitting across the room from each other wearing face masks, and having a detailed conversation on how our sexy time would go. We both confirmed our lack of symptoms and all the safety measures we’ve taken.

Next, we undressed, but kept our face masks on. Then, we thoroughly washed our hands and went to the bedroom.

I had a sheet down and some lube on hand.

Pretty

We laid down on the bed next to each other, but opposite. In other words, his head was down by my feet, and my head was by his feet. And we pressed our flesh together and touched each other all over.

We had earthworm sex! 🙂

Since he hadn’t touched anyone in weeks, it was especially delicious and electric for him – he got HIGH off my good energy, and I basked in his, as well!

We played with each other and shared orgasms, but really it was all the fun touching I liked best. Skinship! Gratitude!

Did we want to kiss and have our usual sexy time routine? Of course. But it was FUN to do something different, and it felt safer, which made us more comfortable and relaxed. And it was definitely an upgrade from phone and video chats. Improvise, adapt, and overcome!

And this was good practice for me, as I open up my intimacy channels next month. I recognize that my actions affect my partners. I’ll be selective and limiting the amount of people I share space with, which means I’ll need to adjust my rates and schedule. I’ll be setting up each session with different rituals and protocols – a conversation about what we’ve been up to, what would feel safe for us, and what we’d like to get out of the session. We must also agree to disclose any symptoms we experience in the days following our encounter.

I know you can’t trust everyone, but you can do your best to lay the groundwork for open and honest communication, and lead by example. If we don’t take some calculated risks, we’ll always be shutting ourselves off from others.

Creative sex for the win!

“Help Me Get Laid!”

By Kendra Holliday | May 6, 2020

Hello! Do I know you?

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.

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An Open Letter to Men Looking to Date Women

By Kendra Holliday | May 6, 2020

A guest post from my friend Gigi Spanks:

The goddess Demeter

To the Men Looking to Date Women,

As a woman in my late 30’s, I have encountered my fair share of thirsty men looking to get laid. I have spent countless hours with my female friends, lamenting over the horrible dates and bad sexual encounters we have endured. These experiences, which unfortunately are too many to count, have resulted in many of us pulling back from the dating world. We are still here, looking for sex partners and hungry for cock, but we are harder to find, more guarded, hiding in the shadows.

So, if you are one of the many men who are complaining that they can’t find women to date / fuck, please read on as I am here to share 5 things to help you be more successful in finding the relationship you want…

1.  YOU ARE THE COMMON DENOMINATOR…  If you find yourself in a situation where no one will date or have sex with you, it is important to recognize that YOU are the common denominator. You need to stop blaming other people (women) or the circumstances for your lack of partners. Ask yourself questions, such as, why aren’t people attracted to me? what behaviors do I exhibit that drive people away? What do I want? Knowing yourself is an important step in being successful at dating. In addition, you should identify what you want from a relationship before you put yourself out there (i.e. casual sex, kinky sex, long term partnership). In some cases, paying for the services of a counselor, life coach or relationship consultant can help you and save you lots of time and frustration down the road.

2. YOU ARE NOT ENTITLED TO PARTNERED SEX… Partnered sex is not just about YOU and getting your dick wet. Partnered sex is about you AND another person that is turned on by and enthusiastically consents to fucking you.  In short, no one is obligated to have sex with you. If you are looking only to please yourself and not do the work of finding / pleasing a compatible partner, solo sex or paying a sex worker for their time / skills may be for you (you read that right, I said PAY for sex.  You have to either put in the time to develop a connection or pay a sex worker, no one gets sex for free…)

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Sex-Positive Etiquette for Men: Discussion Recap

By Kendra Holliday | May 5, 2020

On January 27, 2019, my not-for-profit local community organization Sex Postive St. Louis held a Sex-Positive Etiquette for Men discussion at Shameless Grounds.

Here’s the event description:

This event is free and open to all SEX+STL members.

Men – do you wish we had more female members? (Note: as of right now we have more than 4300 members on our Meetup group. I’m guessing it’s ~ 60% men, 40% women.)

Do you wish women were as fired up to get some action as you are?

When you attend our clothing optional events, is it important to you that there’s a decent number of women there?

Do you want to touch and be intimate with women?

Do you ever wonder how to best approach women? Are you successful in your dating endeavors?

Join us as we discuss sex-positive etiquette for men. We’ll give some examples of how NOT to interact with women online, and constructive suggestions on what works better. If you have questions, we have answers!

Please come if you would like to be more successful dating and hooking up with women. Come if you are a woman and want to share your experiences and preferences. Come if you are a man who is successful dating women and have some insight to share. Let’s all learn together and create a truly sex-positive space for everyone!

The reason why we hosted this event is because our female members informed us that they were being contacted by male members with inappropriate messages.

We have a member harassment policy in place. In addition, I made this quick video reminding men that our group is not intended as a dating or hookup site.

Here are examples of approaches that can be perceived as inappropriate:

  • Sending members you don’t know a message that you’re looking for sex.
  • Attending a happy hour and asking the women there if they will kiss any random man on the street.
  • Posting on the discussion board that we should host a penis size contest and make sure there are sexy ladies on hand to judge it.

When women get bombarded with strong questions and messages like that, it turns them off and drives them away.

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Flirting Tips for Men

By Matthew | May 4, 2020

Dear Kendra,

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?

My reply:

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….

Matthew says:

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.

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Can Creepy Men Be Cured?

By Kendra Holliday | May 3, 2020

Dear Kendra, I don’t know about you, but I know a lot of creepy men. What makes a man creepy? Can creepy men be cured? Or, once a creep, always a creep? Have you ever met a creepy woman?

Kendra replies:

All right, readers, I want feedback from YOU – tell me about an encounter you had with a creepy guy. What made it creepy? What are the qualities of a creep? Can creeps be cured?

Photo by Tim Rulo

Photo by Tim Rulo

Here is what I have to say on the subject – I hope reader input will help shape my understanding of this unfortunate issue.

Being in the sex industry, I’ve met A LOT of creeps. Here is an example:

A few years ago, a man contacted me through this website. He wrote me a couple emails, then met me at an event I advertised – I was part of a sex fair that was open to the public. He seemed nice enough, and asked to meet me for coffee.

I said sure, so we met for coffee. At coffee, he asked me tons of questions and got this weird look in his eyes. He got excited from all the things I was sharing with him. He walked me to my car and asked if he could get in with me so he could ask me a question.

A huge red flag went up, but I said sure, BECAUSE I’M AN IDIOT. (Since then, I have tightened my security and have read The Gift of Fear, and consider it required reading for every woman.)

We sat in the car and he turned to me. “Can I kiss you?”

Disgusted and horrified, I sputtered no. I had NO interest in this guy. He was creepy. What made him think I wanted to make out with him? (Answer: I gave him the time of day. Other things that lead men to think you are interested in them: Eye contact. Smiling. Laughing at their jokes. Being polite. Being female.) At least he didn’t lunge at me.

He whined a bit, then took his leave. I’m very lucky nothing bad happened. I appreciate that he asked and respected my reaction. NEVER put yourself in a closed space with someone you’re unsure of.

Later, he showed up for one of my TBK get togethers. He circled the party, stared, and kept to himself. His behavior made me uncomfortable.

After that, he emailed me two or three times asking when I was going to have another get together.

I’ll tell you when: NEVER. Or if I do, it will be invite only.

It wasn’t just him that put a damper on the party for me – there were two other creepy guys there who drank too much and crossed some lines.

OK, so what made this particular guy creepy?

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My Personal COVID-19 Statement

By Kendra Holliday | May 2, 2020

Please no cock shots

(I know, I know, I should have posted this weeks ago! You’ll see why I didn’t below…)

I sure can’t tell what’s going on out there in the world, what with all the opinions and rumors clouding the facts, but I know we’re dealing with a pandemic, and that I live in St. Louis, MO, United States.

So because I can’t really trust government officials to have the intellect and priorities necessary to keep us safe, I have to rely on my inner compass and core team of trusted advisors.

With that said, I’ve decided not to engage in intimacy sessions the month of May 2020. I hope to resume intimacy sessions in June on a limited basis, but I need to see how the next few weeks play out first.

In the meantime, I’m available for online talking consults and sessions.

Why am I taking this stance?

Because even though meeting with people one-on-one is relatively low risk, the nature of what I do is extremely high risk. I’m very good at safer sex (I get tested quarterly and have never had an STI), but this is a whole different level of STI we’re dealing with – a Socially Transmitted Infection can easily be transmitted during sexy time.

I’ve been sexually monogamous with my partner of 12 years since around March 17. I haven’t been on this level of lockdown since I was married in my 20’s – HA!

I have another partner of six years I haven’t been intimate with for weeks. I’d like to get back with him at some point, and he takes priority over clients and random strangers.

Creepy bird lady

I take my partners health seriously. I know men are at higher risk of dying from COVID-19, but I don’t know what other factors make them more vulnerable – weight, heart conditions, blood pressure, lifestyle habits, blood type, age…

My mission is to help people improve their health and happiness, and my specialty is sex, intimacy, and relationships. I take that seriously. Out of respect for you and myself, I must err on the side of caution in this time of crisis. I KNOW this sounds silly, coming from a person who has had gang bangs and hosted orgies and engaged in crazy fetish work, but what can I say? I’m an ethical slut.

In March, I was blindsided like everyone and found myself paralyzed by fear and grief.

In April, I sat around for weeks, and decided that even though I’m not making money right now (thank goodness for savings and supporters of my mission!), I still needed to do SOMETHING, so I started donating my time here and there, helping others out.

This month, I’m going to shift into a more productive gear and work on some writing projects, creating content, and hosting online events for Sex Positive St. Louis. I’m going to figure out my business model going forward – rates, services, etc.

I’m extremely fortunate that I don’t know anyone personally who has tested positive for COVID-19, including my healthcare professional friends. But many of my friends have had loved ones affected.

How about you? How have you been coping during this unprecedented (at least in the last century) time? I mean, if this goes down like the pandemic of 1918, do you suppose an even bigger spike will hit us this fall/winter? We better be prepared! Hurry up with that testing and vaccine development!

No Shave May!

By Kendra Holliday | May 1, 2020

I did this video announcing my new project: No Shave May!

I already have a head start with it, see? My pubes are trying to bust their way out of my lace panties!

My pubic hair

I can’t get any of my lace panties to hold up these days. I’ve taken to hand washing and trying not to be too sexy for them.

I find the difference between guys who are into shaved heads and the guys who are into natural women fascinating. As a group, the shaved head guys came off as more entitled and disconnected, as if they owned every bald female head. Even though they claimed a woman with a shaved head was a sign of powerful confidence, they seemed to secretly get off on the humiliation factor.

The hairy armpit guys are more respectful and kind. I guess they are hippies after my own heart! These guys see hairy underarms as a badge of sensuality and supreme confidence.

I wonder how big my bush will get. I can’t remember the last time it was fully grown out. I’ll keep you posted on how my hair growth progresses!

Why I’m Scarier Than a Porn Star

By Kendra Holliday | April 26, 2020

This Chihuahua is scared of me

Ed Note: I wrote this back in 2011. Do you think things have improved since then?

I was talking with a friend about my constant struggle to be understood. He mused:

“You are caught between society’s fascination with sex and its horror of it. In a weird way, you’re more dangerous and threatening than a porn star. Porn stars, we believe, are actually motivated by a love of money and fame, which motivates the rest of us, and thus is socially acceptable. But you’re different.

You post pictures of yourselves being fisted because you like being fisted, and you want the rest of us to know about it. And that’s threatening, because – we are all haunted by sexual desire, by appetites that we are all constantly trying to control, and you pride yourself on someone who doesn’t limit her appetite at all… who completely indulges.

Your message is, to quote you, ‘You can have it all…’ you can indulge all your secret desires, completely, to excess, and suffer no consequences. People interpret that, emotionally, like someone saying, You can drink all you want, gallons of vodka a day, and still be fine! Somebody like that would be laughed at. But you’re scary, you’re emotionally dangerous,

Because most people don’t want to drink a bottle of vodka a day. But many people DO desire to have a lot more sex. And you’re indulging that desire, regularly, publicly, and it seems… threatening. Crazy. We’re supposed to have limits! We’re supposed to be responsible!

Let’s face it, you are not superficial, where most people prefer to keep things. You are very real.”

Hmm. And this is very interesting.

Let’s Play the Obscene Nipple Game!

By Kendra Holliday | April 7, 2020

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?

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My Top Sex-Positive Recommendations

By Kendra Holliday | March 3, 2020

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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Why Creative Sex is Better Than Straight Sex

By Kendra Holliday | March 1, 2020

Let me school you on creative sex…

Years ago, I went to a swinger party with an ex. There were six women at the party, and we all had lots of fun. But, to my surprise, when we were driving home, my ex lamented, “I only got to be with four of the women there.”

Huh??

That’s right – he was dissatisfied with only getting to stick his penis in four of the women’s vaginas that night. He was keeping score!

I’ve noticed other times where I’ve played with a man, and we’ve gotten naked, shared pleasure, had oral, but he left disappointed because he didn’t get to do ALL THE THINGS, i.e., stick his penis in my vagina and have intercourse.

I have clients who spend time with me, and instead of basking in female energy and pleasure, they get bummed if they don’t have an encounter that involves them having an 8 inch penis that remains hard for 45 minutes and drilling me bareback in four different positions.

In other words, they feel let down that they aren’t having sex like they see in mainstream porn.

Meanwhile, I’m having amazing, abundant sex with my partner of 11 years that is leaving us both extremely happy and fulfilled.

The Key to Good Sex!

You want to know why?

Because we are having CREATIVE SEX. We aren’t having straight sex!

Straight sex is what you see in mainstream porn. It is male centered. It’s penis focused. It’s vigorous and aggressive. It’s filmed for camera angles, and based around the male orgasm. It’s objectifying. It’s GOAL ORIENTED, which can set the stage for unrealistic expectations and A LOT of anxiety. And anxiety is terrible for arousal!

The women in straight porn are often uncomfortable – from the fake eyelashes and bleached hair and garter belts and heels, to the pussy pounding and loud vocalization and money shot in the eye.

Creative sex, on the other hand, is more about pleasure, skinship, being in the moment. It is about savoring the experience.

Straight men crave intimacy and connection, but they seek it out in a rigid way that can set them up for disappointment and failure. Moreover, it can be off putting or dissatisfying to their partners.

Creative sex is more egalitarian, and allows for more pleasure and orgasms for all parties involved.

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Earthworm Sex!

“Help Me Get Laid!”

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