By Kendra Holliday | August 22, 2022
Category Archives: Event
One of my favorite days of the year is our Sex Positive St Louis annual naked pool party. We’ve been having these for over ten years. It’s the crown jewel of the sunny season, the best way to enjoy a hot summer day.
It’s a private, screened event – we need to know the people attending, meaning they need to be established SEX+STL members, and by that I mean you need to be a part of the community, not just attend one or two events. This ensures a safer environment for those who attend. My C0-Leader David Wraith states the safety rules well: “No sexual activity. No touching without consent! No body-shaming! No slut-shaming! No sexism! No racism! No homophobia! No transphobia! No ableism! No hateration! No holleration!”
We actually refer to it as a “clothing optional” pool party, because we want guests to attend on their own terms. My sister attended our most recent one, and she told me, “I was invited to some other naked pool party, and their rule was: Nudity Required. That bugged me, like my body was meant to be on display for others, so I didn’t go. But when the rules are ‘clothing optional,’ it’s nicer, there’s less pressure, I have agency, which makes me feel fine about getting naked!”
Every year, I invite new people to attend. They act extremely intrigued, but most of them back out at the last minute, telling me they can’t do it. I’d love to know their reasons – are they self-conscious? Are they worried they’ll see someone they know? It’s too bad, because out of all the people who manage to overcome their fears and attend, not ONE person regretted it. EVERY person found it to be an overwhelmingly positive experience – for some, even life transforming.
It usually ends up being about 120 people, from all different backgrounds. (It can be a challenge for folks who have disabilities, because the pool is a 1/2 mile hike, a secret haven deep in the woods.)
Imagine 120 people of different genders, orientations, ages, body types, and ethnicities frolicking in this giant, spring-fed basin:
By Kendra Holliday | August 8, 2022
Here’s how to get over your body image issues:
1. Do a nude photo session
2. Get naked in front of other people
Let me explain.
It’s been almost a year since my hysterectomy surgery. I’m all better, but I’ve noticed my body shifting and changing. I have scars on my tummy now, and fat has gathered around my middle. Sometimes I sit around and feel gross about it. I feel like my clothes are tight. I try eating better. I try being more active.
Last Saturday, I had two events on my calendar: a nude photoshoot with a girlfriend and photographer friend of mine, and a clothing optional pool party. Ugh, being naked around other people was the LAST thing I wanted to do. I yearned to hide under my covers in a comfy nightie instead, but I’m not one to flake out on people just because I’m not feeling it. I tend to push myself to follow through with things I’ve committed to, because it usually works out for the best.
At the photoshoot, I shared my body image concerns with Bianca and Stan. Bianca looked so beautiful and graceful. Stan assured me that I still looked mighty fine and not that much different from when he first started photographing me five years ago. I started to relax, and walked around the studio naked as if it was the most natural thing in the world, because it WAS.
By Kendra Holliday | February 10, 2021
Ed Note: This was originally published June 29, 2012. Larry Flynt died today, Feb 10, 2021. What a legend. 🙁
Earlier this year, I was featured in Hustler magazine.
But that was NOTHING compared to what happened this week! Larry Flynt visited St. Louis and I got to meet him!
I asked one of my girlfriends to go with me. “You want to be seen with a hot chick, don’t you?” she commented drily. Well, yeah!!!
With her white power suit and mirror shades, she looked like my bodyguard – a super sexy Charlie’s Angels type bodyguard.
We walked up to the store and were greeted by a bearded man handing out postcards. Upon first glance, the slick marketing material looked like it was made by Hustler, but upon closer inspection, it proved to be anti-porn literature!
Every year millions of men and women become addicted to porn. Millions let their lust control them. ‘Lust’ is having sexual or pornographic thoughts about another person.
In the book of Matthew, Jesus says if you LOOK at a woman with LUST you’ve already committed Adultery in your heart.
In the book of James, the Bible says that if you break only one commandment, you’re guilty of ALL of them. Breaking God’s law is called sin. Sin leads to death…
So clever of them to try and make people feel guilty for coming to an adult toy store.
By Kendra Holliday | July 6, 2020
I get about 2-3 inquiries a week asking about play parties – when is my next one, if I know of any coming up, etc.
You all are brave to want to experience orgies in the middle of a country that is being torn asunder by a highly contagious pandemic! Masks off to you, my freaky friends!
Meanwhile, I’m over here sitting in pandemic limbo, trying my best to wait this crisis out. Events are on hold; I don’t even feel comfortable scheduling one-on-one intimacy sessions. ;(
That said, I have friends in St. Louis who are optimistically planning their own play party this October. They want it to be bi-male/trans friendly. They asked me for advice on how to host a successful play party.
First, you should review my party page – it has loads of good info, FAQ, and guidance.
Second, here is a checklist of things to keep in mind:
- Location. Hopefully, you live in house that is conducive for parties. I don’t – I live in a 1000 sq ft fairy cottage that can only host threesomes, foursomes, and the occasional gang bang. You want a classy, clean space that offers several stations for playtime. I’ve rented houses in the past, but that can be risky. My best bet has been a community member offering to host.
- Accessibility. Is your space accessible? I’m sorry to say I haven’t always considered this in the past. Regardless, you should state if it is or not.
- Allergies. State if any pets live at the location.
- Parking. How many people do you want to attend? 12? 50? 100? Make sure you include parking instructions in your party confirmation email.
- Screening. Do you have a sex-positive network? I keep an email party list that has about 600 people on it. Every time I schedule a party, I send out a bcc email to the list and keep track of who responds. I try and curate a good mix of people.
- Budget. Lots of supplies go into a party, so think about how much you want to charge for overhead. $50/person? If everyone pitches in, these nights can be unforgettable!
- Do you want to have it catered? I always check with Shameless Grounds first for catering.
- Drinks. Do you want wine and beer only? BYOB? Have ice and mixers on hand.
- Other drugs. If you don’t specify in your rules, people will take liberties.
- Privacy. Speaking of rules, most people attending play parties like to keep it private, so make sure and acknowledge confidentiality.
- Mood music. Hire a DJ or think about playlists/stereo setup.
- Good lighting. Adjustable, ambient lighting is nice. Most people like it dim. Real candles can be dangerous, so I use safe fake candles, light machines, lamps…
- Safer sex supplies. Be sure and have condoms and lube handy at every station. Other good items to have on hand are towels, sanitizer, mints, small trash cans, well-stocked bathrooms…
- Enough play stations. Do you have several beds? A massage table? A SYBIAN? Do you want to add an air mattress or two? Will this be a kinky party with spanking benches and crosses? Consider putting sheets on couches for easy cleanup.
- Theme? I LOOOVE party themes, but I try and make them reasonable for most people.
- Gender ratio. If you don’t carefully screen, you can easily end up with 40 single men attending. If your party goers love lots of female energy, consider allowing women to attend at a discount, or free if they volunteer to mingle with guests for a certain amount of time.
- Volunteers. Speaking of volunteers, enlist a few friends to help you set up, host, clean up.
- Icebreakers. People often arrive nervous, so think of icebreaker games or a demo to kick things off after people have had a chance to socialize for a couple hours. One time, we did a pussy parade, where every woman who wanted to could line up on a couch and show off their pussies. We had eight beautiful pussies lined up, and the guests slowly walked past to savor the view!
Here’s an example of the email I send out to potential guests, you can borrow language from it:
By Kendra Holliday | May 5, 2020
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.
By Kendra Holliday | January 1, 2019
One of the things people contact me the most about is my TBK Play Parties. I’ve held more than a dozen over the past few years, and I’d love to have more! If you know of a classy place within 45 minutes of St Louis that can hold 50-100 adults, let me know. I’ve rented from AirBnB and Vacation Rentals, but the best bet is someone in the community volunteering their home. So, let me know if throwing an orgy is one of your 2019 New Year’s Resolutions!
You can read FAQs and more on my Party page. If you’d like to be added to my party email list, email me answers to the questions listed on that page. With more than 600 people on my list, whenever I announce a new party, the spots fill pretty fast.
Here is what someone attending the last party shared with me about their experience:
“There was a couple in one of the side bedrooms making love with the door open. We walked by and saw them. Since the door was open, we stopped to watch because we love being voyeurs. The couple smiled and invited us in. We obliged and entered the room. The hallway light cast enough illumination to see them. The ambient lighting made the display all the more intimate.
They were engaged in a doggy-style position with a slow and steady pace. After watching for a couple of minutes, my wife Jasmine walked up to the woman and whispered softly in her ear. I could not hear what she was saying. I imagined in my head she was complimenting the beauty of her golden brown skin or her phenomenal smile she was displaying when she saw us watching them.
After Jasmine was finished whispering, I saw the smile again return along with an affirming nod followed with a verbal, ‘Yes you can.’
By Kendra Holliday | July 29, 2018
Years ago, I made it a point to post five blog entries a week.
Nowadays, I’m more prone to moving old posts to the top of the home page whenever the topic is requested or relevant. It’s pretty easy to do, since I have over 600 posts – some of them I forgot I even wrote!
But I keep wanting to write about new experiences – sharing is helpful for others, and it’s therapeutic for me. Life keeps zipping along in a blur! I still want to write about the medical-themed play party I hosted in March! It was such a mindfuck.
Here are some other topics on my list:
Wheel of Consent Training – shamans, witches, empaths, consent and power of touch, fruit, symbolism
The Pull of the Moon
Under Attack – SESTA FOSTA
It’s You. It’s Me.
Love, Sweat and Tears menopause documentary review
Recap of Tantra workshop
Reveling in my latest threesomes
Updates on my daughter, parents, struggle with booze
Last month, I gave a talk at The Ethical Society on Desire (they will post a recording of it online soon). The very next day, Huffington Post published an interview with me about the work I do, and it generated a LOT of interest! And then this morning, I presented a workshop on sex and disabilities at the AASECT Summer Institute at Washington University.
In between all of that, I’ve been seeing clients, some local, some from out of state. Every week is different, with its own set of challenges and rewards.
Oh, and one more thing – I’ve been experiencing psychotic episodes.
I’ve touched on this before – the past couple years have been intense with a shift in my hormones. It’s like I’m going through puberty again. I’m very sensitive, and when I get too stressed or overwhelmed, I have a breakdown. I lose touch with reality.
This has happened about six times in the past 18 months. I go from cranky and irritable to a full-blown maelstrom of emotions – all I can do is hang on and ride it out. It’s better to lean into it than to fight it.
By Kendra Holliday | June 22, 2018
You know you’re in a sex-positive environment when a woman can doze off nude on a day bed outdoors by herself, and not worry about anyone molesting her.
And, of course, at other times you can see a bunch of people fucking in every one of the beds, in all sorts of fun combinations. That’s also very sex-positive.
My week at Desire with the Life on the Swingset crew was better than I imagined it would be. And I have a pretty good imagination!
I was nervous and excited to travel all by myself to a couples only lifestyle resort in a different country. I only knew a few of the people who would be my naked neighbors for the week (out of 120 rooms, the Swingset had booked 88 of them – next year, they’re booking ALL of them!) But I was determined to embark on this adventure with a positive mindset – after all, what did I have to lose? Just my clothes!
As inspiration, I brought this book along with me on audio – it’s all about discovering your personal legend, and has great quotes such as, “There’s a language in the world that everyone understands – it is the language of Enthusiasm – of things accomplished with love and purpose, and part of a search for something believed in and desired.”
I highly recommend it!
When I arrived, Cooper gleefully greeted me naked, with an espresso martini in hand.
The staff served me a glass of sparkling wine and a cool towel to refresh myself from my travels. I would continue to drink sparkling wine for the rest of the week! And other cocktails, and sushi, and guacamole, and cake, and lord knows what else! Eat, drink, and be merry!
I made a name tag charm necklace (helpful when you aren’t wearing clothes!) – it’s my Twitter header.
— Kendra Holliday (@TBK365) November 9, 2015
After my necklace was made (festooned with love and good charms!) I stripped naked and joined the group. A super nice couple gave me a tour of the resort. It’s not very big, but it’s laid out in a meandering fashion, right on the beach. Speaking of, my room had an ocean view!
By Kendra Holliday | December 22, 2017
Continued from previous post…
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.
By Kendra Holliday | December 5, 2017
One of my goals is to get out of St Louis once a month for a change of scenery.
In 2017, I went to Iceland, New York, Kansas City, Indiana, Virginia, Rhode Island, Florida – and I even went crazy a few times! I’m so glad I finally got my mid-life crisis under control, PHEW!
Next up on my itinerary is a National Sex Ed Conference in New Jersey Dec 5-10 – I get to see Dr Ruth and Dr Elders in real life!
2018 is shaping up nicely – for our 10th cabinversary, we’re trying out a new cabin! It doesn’t have a hot tub, but it does have a wood burning fireplace, which is KEY.
I’ll be hitting KC again in Feb, and in March I’ll be presenting at Eroticon in LONDON!
It’s great timing, because the Top 100 Sex Bloggers of 2017 was just announced, and I’m #9 on the list!
My presentation is called Shocking the System: When Your True Life Tales Cross the Line.
By the time I’m finished telling my tales, people will either love me or hate me!
By Kendra Holliday | December 3, 2017
I haven’t hosted a TBK play party in MONTHS. 🙁 I can’t find the right venue within 45 minutes of St Louis! It has to be classy and spacious. If you have any suggestions, please let me know! (Psst I have found a great space for a Doctor/Nurse medical theme play party. Drop me a line if that is something you’d be interested in!)
In the meantime, my not-for-profit org Sex Positive St Louis is having its annual FLESHTIVUS event Dec 15. Here are details (you need to be a member of our Meetup group in order to view them). This is not a play party; it’s a clothing optional holiday party.
Besides that, I’ll be at Shameless Grounds TODAY, Dec 3, leading a Dating Safety talk at 2pm. These are our last events of the year. I have to admit, I’m getting frustrated with hosting events. We’ve organized over 700 since we kicked things off in 2010, and we have more than 3,500 members!
But attendance is down. Last month, we paid big bucks to bring in national speaker Ericka Hart, and only about 30 people came! I think we’re in a bad cycle – folks take for granted that we are here, so they don’t show up, and then we get discouraged and don’t feel inclined to organize more events. As you know, it takes a lot of time and energy. On top of that, as soon as I do bite the bullet and announce a new event, I cringe because I know several people won’t bother reading the instructions and will email me asking questions, which creates more work…
As you can see from this tweet, I’m not alone here (click to view images)…
— Kendra Holliday 😻 (@TBK365) December 3, 2017
The same sentiment can be said for Shameless Grounds – we’re SO LUCKY to have a sex-positive coffee shop in St Louis, but they are struggling. If you want access to great things, you have to support them. Otherwise, they will shrivel up and die on the vine.
Where is the passion?? I’m feeling burnout…
As I sit around and ponder my local dilemma, I have my sights set on other endeavors – I’m going places!
By Kendra Holliday | December 24, 2016
One of the funniest things that happened this year was the Whisper Orgy at CatalystCon last April in Chicago.
CatalystCon occurs once or twice a year, and provides a great platform for connecting and learning with other sex-positive people from around the country – and even the world.
I met Sigga Dogg, a delightful sex educator from Iceland!
One night, a play party was hosted in a large suite, and everyone was invited.
But first, I had to shower and get ready.
I LOOOVE showers like this! So fun for an exhibitionist. 🙂
There was a massage table set up, bondage, and a bedroom where a bisexual orgy was going down. I saw three men having sex and it looked like this:
Unfortunately, it got loud and there were some other hotel guests who caught wind of the party and tried crashing it. My partner Matthew stood in as doorman while our friends got frisky. Some guys tried pushing their way in, but Matthew barred the way.
Peeved, they reported our party to hotel management, which put a damper on things. In order not to interrupt the orgy taking place, they closed the bedroom door while they spoke to management, so that sex room ended up getting all stuffy and smelling like ass and lube.
Management warned us that if it got one more complaint, we would be kicked out of the hotel, so that freaked everyone out.
As we stood around trying to figure out what to do next, it was insisted that we be EXTREMELY quiet – nothing above a whisper.
So what did Matthew do? He put the Whisper Song on his phone very softly and walked around the suite playing it.
Keep in mind, this is a politically correct crowd and we had just spent a day discussing consent and gender roles, so it was especially funny this super sexist song was played.
Luckily, everyone was having too much fun to get upset about it.
I was amazed to see an entire room of people dancing and fucking enthusiastically and silently – it was like watching a YouTube video on mute!
Finally, the party got moved to a downstairs ballroom. Everyone dressed, gathered up their gear, and migrated. But by then, the spell was broken, and we headed to a tiki bar.
By Kendra Holliday | November 11, 2016
Another incredible weekend at the cabin.
The cabin is under new ownership now, so they made some nice minor improvements, such as new furniture, bedding, and this sign:
…unless you have a sex blog.
We had a fire going ALL WEEKEND, which apparently is as bad for you as smoking cigarettes, godammit. I guess it’s a good thing I don’t have a wood burning fireplace at my house.
Here’s a pic of me in the hot tub from a previous year:
By Kendra Holliday | November 6, 2016
I’m proud to say that the gang bang I had for my 40th birthday kicked off a tradition among my friends – orgies celebrating their 40th, 50th, etc. birthday! There have been several in the St. Louis region, featuring various fantasies and frivolity, sometimes before a fire, sometimes beneath the glow of a red light…
The thing is, you have to EARN an incredible orgy for your birthday – you can’t just dial it in. You need to spend years cultivating friendships with people who are in touch with their sexuality, and, more importantly, love and respect you.
My partner Matthew lovingly organized my gang bang, so it was only appropriate I return the favor by arranging a comparable 40th birthday celebration for him.
He helped make my fantasy of being surrounded by awesome male energy come true, so guess what? He wanted to be surrounded by awesome female energy!
We improved on the formula. This was not just a reverse gang bang, no ma’am.
This was going to be BETTER than that.
After making a list of who we would like to be present, I sent the following invitation to eight women:
Dear Women of High Esteem and Even Higher Regard,
I would be so honored if you could lend your sacred female energy to the celebration of My King’s 40th birthday celebration.
Please bring a robe to wear once inside. Cocktails will be served. Decadent catering by Shameless Grounds.
The premise: Women will lounge about in robes, chatting and bonding. The King will beckon us one by one back to his chamber for exclusive quality time, on each woman’s terms. Please know that you are not expected to do anything you do not want to do.
The evening will culminate with some group worship, with guest comfort level paramount. The goal is for everyone to be comfortable and well cared for.
With Sensual Respect and Reverence,
Queen Kendra of The Beautiful Kind
To our delight, EVERYONE responded with an enthusiastic YES!
By Kendra Holliday | August 14, 2016
The experience blew me away. I am a changed person.
I expected to soak up new energy in a new city, new ideas, new people, and learn about tantra. I’ve read a lot about it online, plus I read Barbara’s book Urban Tantra twice – yet I still didn’t have a proper grasp on it. I think tantra is like Burning Man – you have to immerse yourself in it in order to “get it.”
Well, I got all that and more – I met other sex workers, fetish models, dominatrix, tantrikas, and other specialists. I learned about marketing, BDSM, gender politics, and about other cultures.
That picture of Barbara on the right? That’s what the week was like – we were sparkling, ecstatic, and open-hearted.
My NYC escort for the week was my good friend Matthew Stillman, who was also attending the course. He’s like a brother to me – I was so lucky to spend the week with him – it was my first time to NYC and I was so intimidated! I couldn’t have been matched with a better soul – he’s lived in NYC his entire life and was an excellent guide.
We walked all over the place and took the subway!!! Columbia University, Central Park, Brooklyn Bridge… I reread A Tree Grows in Brooklyn on my trip, and found this slut-shaming passage still relevant, 70 years later: