Things That Have Been Up My Ass

By Kendra Holliday | September 26, 2019

My butt has seen better days.

My butt has seen better days.

Stop and think – how many things have been up your butt?

I have to admit, I’m just not that into the anal. It doesn’t occur to me on a regular basis. I’m much more oral and vagina-centric. So the things that have been up my butt have been few and far between. And the experiences have been good, bad, and ugly.

Here’s a quick-n-dirty list:

– Poo. EVERYONE has had poo in their butt. I hate poo. Poo is gross. Poo stinks. I don’t like smelling it, and I sure as hell don’t want other people smelling it. I’ve been using Poo-Pourri, and it works pretty well. Not that I spray it up my butt. You’re supposed to spray it in the toilet before you have a seat.

– Pink vibrating beads. I had an AmaZing experience with these. You can read about it here.

– Flexi Felix anal beads. You can read about that cute toy here.

– Bendybeads. I wouldn’t recommend these for beginners, but they are nice and sturdy, made of safe, smooth silicone. It’s fun to slowly pull them out as you’re having an orgassssmmm….

Bendybeads

Bendybeads

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Top 10 Things That Have Been in My Vagina

By Kendra Holliday | September 26, 2019

I thought this would be a good topic to follow the vaginal penetration post.

A few years ago, the Riverfront Times published an article titled Top Ten Things That Have Been in The Beautiful Kind’s Vagina: NSFW. I was SO honored. I’m pretty sure no other woman has that distinction. The article is by now out of date, so I’m going to offer my own, more accurate version. GOD my vagina has been good to me! Holy shit I’ve had a lot of people and things in my vagina! (For context, click here to see what my pussy looks like – the glorious gateway to my vagina!)

10. Tapio, my wooden dildo. One of my favorite sex toys. My lovely super smooth dildo glows like a tiger’s eye and smells like cedar. Very warm and inviting. He is the most living inanimate object I’ve ever fucked.

Tapio wooden dildo

Tapio wooden dildo

9. An abortionist. I seriously can’t imagine what life would be like right now if I hadn’t gotten an abortion in 2007. It was a sucky situation and a difficult decision to make, but I am infinitely grateful I had the legal option to exercise my right to choose.

I love contrast.

I love contrast.

8. Big black cock. I’m sorry, but even if the cock isn’t technically “big” (and lord knows I’m not a size queen!), it still sounds better to say it that way. I’ve had the pleasure of fucking several handsome black men. Here is one of them.

7. Hitachi Magic Wand Attachment. OMG I LOVE THIS THING! I use the Hitachi Magic Wand every day, but every once in a while, I add the attachment. It fits over the head and inserts perfectly snug. I lube it up and it’s like a benevolent alien tentacle bathing me in white light, inside and out. It’s gripping and intense and when I cum, it hurts so good! My vagina grabs on tight and doesn’t want to let go. I yelp when I pull it out after my rockin’ session, phew!

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10 Worst Things That Have Been in My Vagina

By Kendra Holliday | September 25, 2019

You know what’s awesome? It was much easier writing the list of Top 10 Things That Have Been in My Vagina. My positive sexual experiences far outweigh my negative, and shine warmly in my head, eclipsing the dark, gross shitty stuff.

That’s because I have not let the negative things define me. I have overcome them, and defined my sexuality on my own terms. Each of the things below sucked bad, but they all made me a stronger person as a result.

Look, I’m not much into trigger warnings – I kinda figure if you’re alive and on the internet, you’re going to run into some raw dog shit. But I’ll go ahead and let you know that the list gets progressively worse. A yeast infection is a walk in the park compared to some of the hell that follows.

I need to go to bed.

UGH. Give my pussy a break!!!

10. Yeast. I’m glad to say I have a hardy vagina – some women I know have to deal with chronic yeast or bladder infections. For the most part, mine can endure all kinds of crazy activity and then go on about its business. I have had a few yeast infections though, and itchy, pissed off vaginas are no fun! They’re actually pretty gross. It’s cool modern medicine has evolved such that you just need to pop one pill orally and be done with it, as opposed to seven days of injecting applications of messy creams up there.

9. Bad bacteria. I’ve had two nasty, disgusting bacterial vag infections in my life, and they both developed from the same hot tub. It was a nice, clean swinger hot tub in West County, and I’ve been in all kinds of hot tubs and lakes with no problem, and no one else who was in the tub had an issue, so it must’ve been a bad reaction with my personal chemistry. I smelled like rotting fish down there. Had to go to the doctor for medicine, good grief! Needless to say, I stopped hot tubbing with that couple, even though they were nice. I had gross associations with them, like when you eat a can of sauerkraut and then throw up afterward.

8. A really big dick. I’ve been with all sizes of dicks. I prefer average size – 5-7 inches when erect. I dated one guy for a while with an 8-inch-dick. It wasn’t ideal for me. Then one day, I slept with a man who had a 9-inch-dick – talk about a world of hurt! IT SUCKED. I wasn’t into it AT ALL. I grimaced my way through it and avoided him after that, which made me feel gross.

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What to Do in St Louis (Besides Me)

By Kendra Holliday | September 5, 2019

I’ve been having lots of national speakers (Joan Price! Marty Klein!), friends, and esteemed clients travel to St Louis to see ME or attend conferences, events or fulfill prestigious speaking engagements, and they often ask me what St Louis has going on.

Well, let me tell you – there’s A LOT going on between the legs of The Arch!

Lady Lascivious Liberty! BE FREE!!!!

Lady Lascivious Liberty! BE FREE!!!!

From the honorary sex-positive Ambassador and Queen Whore Madame of St Louis, here are my suggestions!

The City Museum downtown is the MUST SEE place in St Louis. TRUST ME AND EVERYONE ELSE AND GO THERE. You can climb around and explore so many levels – from the rooftop to the underground caves! Listen to my friend Max talk about the interactive features of this hardcore unique museum. Kids love this place, and so do adults. (Pssst, there are nooks and crannies for getting injured, or a little nookie with your sweetheart if you’re lucky!) Seriously, I love taking people there. Every time I explain it to them on the way there, they say, “yeah we have something like that in our city”, and then when they get there, they shit their pants and I feel crazyproudsmug. 🙂

Shameless Grounds is a rare gem – we are SO happy to have it! It’s a sex-positive community space and coffee shop. The food is really good! They host so many great events and have a sex library! (Psst – look for the wall of beautiful vulvas backlit above the bookshelves 😉 ) Be sure and check out their calendar while you’re in town, and while you’re at it, check out SEX+STL calendar, too. We cross pollinate all the time, and the entire community benefits!

Joan Price and me at Shameless Grounds!

Joan Price and me at Shameless Grounds!

And while you’re in the neighborhood, go pay your respects to the Anheuser-Busch Clydesdales. Not only are they spectacular beasts, but they offer better hospitality than most people — free beer!

If you have a car (public transportation is NOT the best in St Louis, but now we have Uber and Lyft!), drive around the city and marvel at all the green and red – so many trees and brick buildings. Beautiful architecture. There’s even a documentary on St Louis BRICKS by my friend Bill Streeter!

HOLY SHIT – did you know that most of our attractions in beautiful Forest Park are FREE?! You just have to be aware of $Parking$, incidentals, and Special Exhibits.

If you like art, you better get your ass to our incredible Art Museum. Be sure and say hi to my boyfriend (he may or may not practice Responsible Hedonism…):

I just want to climb on him!

I just want to climb on him! But omg I better not.

When I used to strip on the East side back when I was 19, I would often be driving to “work”, feeling a sense of dread, then I would declare a silent scream FUCK IT, and bust a U-turn and spend the day at the glorious Art Museum instead. One placed sucked my soul, the other place nourished it…

I like taking different people to the museum and pretending it’s a giant Art Mart, and we get to pick one thing out of each gallery. I’ll say in a loud voice, “Where are the price tags on these things?!”

But whatever you do, DON’T TOUCH ANYTHING in the museum, unless maybe a toilet seat. Otherwise, the security guard stationed next to every piece of art will cut you.

The History Museum is nice, if you’re into that kind of thing. They had a fun Prohibition exhibit a while back, as well as one on Lingerie throughout the decades. And Little Black Dresses! And toys! They have a great marble selection in their gift shop! I have a lot of them in my bedroom…

I took this pic at the History Museum!

I'm ready to see you!

I’m ready to see you!

And if you like history, The Campbell House Museum downtown is splendid.

Our ZOO is one of the best. Every year, they update a section so it is better for the animals, and fun for all us gawkers. One of these days, they will get around to the lions and tigers and bears, oh my!

Grrrrrrrrr!

Grrrrrrrrr!

Get your geek on at the Science Center. They’ve featured some really fun exhibits in the past, like Bodyworlds, Dr Who, and Sherlock Holmes.

If you fancy gorgeous gardens, visit our Botanical Garden. I’ve been to gardens in other countries, and this one rivals all of them. This is one of those places I go when I want to have a ME date.

Iris Garden at MoBot

Iris Garden at MoBot

Beautiful Tower Grove Park is right next door, and has the most variety of trees in the city.

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My Sanity Plan

By Kendra Holliday | August 21, 2019

The past couple years, I’ve struggled with mental health issues.

Here is why:

  1. Menopause – I have severe symptoms. It’s like going through puberty again, ugh!
  2. Alcohol addiction – I was stress drinking, which was making things much worse.
  3. Genetics – my family is prone to mental illness.
  4. Life stressors – my aging parents, my daughter moved out, sensitivity to my client’s baggage and trauma.

I go through periods where I can’t function, and it SUCKS!

I’m glad to say I’ve been enjoying a few good weeks, phew! I made this video to show myself for when I am down again:

My therapist Dr. Diane Sanford wrote a book called Stress Less Live Better: 5 Simple Steps to Ease Anxiety, Worry, and Self-Criticism. In it, she speaks of the teachings of Buddha: “To end suffering, we must retrain our minds to be aware and allow whatever happens without trying to cling to pleasure or avoid pain.”

Ahhh, that’s interesting. I’m practically allergic to suffering, especially the suffering of others, so how can I cope with it better?

I created a Sanity Plan. My Sanity Plan is a living document I update or refer to whenever necessary. My friend Metta May has a similar setup – she calls it H.E.L.P. – Hoes Enjoyin’ Living Plan! Maybe something like it will help you, too. After all, most of us are dealing with our share of stress, and it can get overwhelming. We need all the balance we can get! Depression, anxiety, and addiction are ravaging our country – shit is WAY out of whack!

Here are the key components of my Sanity Plan:

I list the things that are causing me stress/bumming me out.

Next, I list some good ol’ gratitude. What are the good things in my life?

For instance, if I’m getting frustrated with catty women, I think about all the good women in my life.

Or if I’m annoyed with men who are a pain in the ass, I review all the good men I know.

I think about things to look forward to – I have a couple trips planned this year, to Colorado and Florida, yay!

I remember the causes I support – making a difference and giving back helps me feel better.

Then, I’ll review my list of tools for finding balance and feeling better.

My self-care list includes supplements I’m taking, books, podcasts, types of therapy, exercise, music, massage, LEGOs, my meditation app, and of course, SEX!

The good things in life can be small and simple. Here is an example:

It’s so nice to be feeling good right now! The better I feel, the more I can be of service to others.

What does YOUR Sanity Plan entail? If you’d like help creating one, you can book a consult with me. Or, we can just talk about sex, that’s always fun!

 

Toxic Masculinity from a Sex Worker Perspective

By Kendra Holliday | August 16, 2019

Trust me, I’m a wise witch!

I’m going to preface this with the following disclaimer: I’m a witchy, woo woo, sex worker goddess, and this brain dump is going to sound crazy. I’m fine with that, as I fully embrace my hormonal mood swings and non-traditional way of thinking. I live in a society with lots of self-imposed cages, and my motto is “Think outside the cage.”

So, hear me out, let it all sink in, and let me know what you think!

Toxic masculinity goes hand in hand with white supremacy, and it’s making me sick. It’s making A LOT of us sick.

I’ve been diving deep into history, addiction, psychology, science, and more, and I’ve connected some dots.

Centuries ago, people from Europe set out and explored the world. They invaded many areas and took them over. They brought disease, death, and disruption to the people already living there.

They set up elaborate exports and imports of toxic trade – sugar, tobacco, alcohol, and slavery. They brought oppressive religions and destructive concepts that were deadly and divisive.

They declared that people, plants, animals, and places were all possessions. They put up fences, walls, and demanded territorialism.

They sought to control everything, and lived with a scarcity mindset. They instilled and lived in fear. They were hungry for power imbalance. They felt they were anointed by God, and thus justified in all their actions.

These things represent male energy: fire, cars, guns, alcohol, nicotine, conquering, destruction.

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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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Why I Love Inexperienced Men

By Kendra Holliday | July 3, 2019

One of the best parts of my job as a sacred prostitute is that I get to spend time with adult virgins. And every time I do, there is one less adult virgin in the world. 🙂

After a recent encounter, one of my former virgin clients shared this with me:

Porn has almost completely lost its luster for me. I find it vastly inferior to the memories of the experience I had with you in St. Louis, and those are just memories! All I have to do is think of you – of your smell, eating your pussy, kissing you, fucking you, feeling your weight against my body, intertwining my legs and arms with yours – and I am instantly aroused beyond anything porn can do for me. Frankly, now that I’ve had a taste of the real thing, it’s hard to see porn as anything other than a pale imitation of what sex is really like.

Yes I'm easy!

I love helping my fellow man.

This man and I would love to have another session, but logistics are challenging – finances and distance – he had to drive hours to make it happen, which I think is very brave and commital – Cowboy Ethics! Ride for the Brand!

By the way, inexperienced men tend to be some of the best pussy eaters! It’s TRUE. ESPECIALLY when they read and research in preparation for our sacred encounter – two great articles to read before you enter my bedroom chamber is “How to Eat My Pussy” and “What I Like and Don’t Like.”

That’s not the only reason I love inexperienced men. They’re more respectful and grateful. You get to teach them how to be good lovers. I wish I could get to them when they’re younger, before they’re warped by porn and misinformation, but society can’t handle that.

One of my clients is quite unique – he has sickle cell anemia, which is a rare blood disease.

Here is the initial request I received from him:

My name is Robert and I am 38 years old. I saw an article about your blog in the RFT. I’ve been reading your blog off and on since then. I’m learning a lot from your advice and the advice of others on your links column. The experience has really been enlightening. I hope you can enlighten me some more.

I have sickle cell anemia. It’s a blood disease that misshapes the blood cells and make them pretty much incapable of carrying oxygen through the body. Their odd shape can get them stuck in the bloodstream; it causes chronic excruciating pain that needs medical attention. It can be deadly in some cases. Eventually, the body’s organs become negatively affected.

I suffered a stroke when I was 17, my senior year in high school. I was diagnosed with kidney failure in 2002 and started dialysis in 2003.

Throughout my teens, I was really sick, so I relied on my parents to take care of me. This made me decide to stay away from any kind of personal relationships. A couple of months after my stroke, I declared myself asexual; I figured no woman would want to be in a relationship with someone who wasn’t totally healthy.

After the kidney failure diagnosis, I started dialysis in 2003. In the five years of dialysis, I had only one bout of severe pain. I owe it all to my changed lifestyle of eating better and exercising as much as I could tolerate.

The positives only got better from there. In the summer of 2007. I got on the transplant list. In 2008, I got a new kidney. I now have a clean bill of health.

Last year, I declared to myself that I would now seek out a relationship, and if the friendship turned into something more, I would see where it goes. I am healthy and confident enough that a love life would be sustainable for me.

My problem is that I’m still anemic. That’s never going away. I get fatigued easily. At this stage of my life, I’m wondering about sex. I don’t know how long I would last and what I could do.

I love my doctors, but they’re not sex therapists, so they can’t really help with this worry. If I’m in a relationship that involves intercourse, I need to ease myself into the act and last for as long as it takes for both of us to be satisfied. Can you help?

Waiting for your kind words with baited breath,
Robert

I was intrigued. Right away I did some research on sickle cell anemia and sex and found there isn’t much out there. You’re supposed to drink a lot of water to hydrate yourself, and men tend to have prolonged erections. Looks like we’d have to learn together!

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Does Your Vagina Stink?

By Kendra Holliday | June 15, 2019

Ed Note: My friend posted this on facebook the other day:

“So anyone who is close to me knows that I have some very strong opinions about the way modern society portrays the female genitals. One aspect of that topic is ‘cleanliness’, or the idea that the female anatomy is somehow naturally ‘dirty’ or ‘smelly’ and therefore women need products to help ‘correct’ the problem.

I found this Summer’s Eve ad in a magazine today and I almost screamed.

This is not OK.

This is not OK.

Don’t forget your ‘V’ this valentines day’???

Fuck you, Summer’s Eve. Fuck you for building an industry around making women feel terrible about their bodies and their sexuality, and for pushing ideas and products that are actually counterproductive to vaginal health. And fuck you for implying that I need to go ‘wash my gross vagina’ before I let someone near it this Valentines Day. I invite anyone to share this who is tired of being told they need to douse their genitals in floral perfume to be considered worthy of attraction or physical affection.”

So, I’m sharing it.

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Up Skirt

By Kendra Holliday | June 9, 2019

Took this pic spontaneously the other day – just bent over and snapped a turtle’s eye view real quick. You can tell it’s unplanned because my undies don’t match – silly red Christmas theme with Scotties. Christmas in June!

I love this dress.

LOOK.

Let’s Play the Obscene Nipple Game!

By Kendra Holliday | May 31, 2019

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 First Time Not Committing Adultery

By Kendra Holliday | May 24, 2019

Ed Note: This is a guest post by Jem.

I was married for twelve years. For almost all the time we were together, everything was good. Almost.

About eight years after we got married, my husband forced himself on me. We were getting into bed, we were both sober, I had no idea what he was going to do. He held me face down. We’d played at this sort of thing before.

This wasn’t playing.

I shouted at him to stop. He’d never done anything like that before. Not even close.

I got dressed, left and went straight over to see a friend. He was a lawyer. It was about eleven at night, he could see I’d been crying. I told him what had happened, and at first he thought I wanted him to report a rape. I just wanted a place to stay and a friend to talk to.

My husband didn’t rape me. He betrayed my trust, didn’t respect my wishes, was clearly on some sort of power trip. He never did anything like it before or since. He was deeply ashamed by what he did, and had a harder time forgiving himself than I did.

My friend and I talked for hours. We ended up talking about sex and the law. At some point he said that adultery was when a man and a woman had consensual, penetrative sex. Nothing else counts. We had fun coming up with things that weren’t adultery: blowjobs, gay sex, buggering a sheep, being tied up and having five guys come over you … not adultery. Grounds for divorce, but not adultery.

I stayed the night in his spare room. He gave me a T-shirt to sleep in. It was about three in the morning by this point. I lay in bed, and decided about a dozen times that I would go next door. I didn’t.

We met up at a coffee shop about a week later because he wanted to know how I was. We didn’t buy coffee, we decided to go back to my place and drink coffee there. We sat on my sofa, talked, I told him how grateful I was for his support. How everything was better with my husband, now. It was, we’d talked and he was guilty and sorry. At some point, my friend put his hand on my leg. He had to get back to work, he said.

I’ve just got no idea who made the first move. We kissed, we stopped kissing and looked at each other and I said ‘oh no’. We joked about this later. We both knew at the coffee shop that this would happen. We didn’t plan it, but put it this way: I was wearing matching underwear. Then we were kissing again and I think I was the one who lifted up my top, but that might have been him. He pulled up my bra and sucked on my nipple so hard it probably should have hurt. It didn’t. Then he really, really had to get back to work.

The first time we didn’t commit adultery was three days later.

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Lingerie and Henna!

By Kendra Holliday | May 17, 2019

I got new undies from Victoria’s Secret from a friend, and henna from another friend! Too bad it’s so faded here, it only lasts about two weeks:

Victoria’s Secret

Here’s a colorful pair!

Poke my dots!

Ahhhh they’re radioactive! 😉

Image with colors reversed

 

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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