My Top Sex-Positive Recommendations
By Kendra Holliday | April 9, 2022
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 | March 24, 2022
Just a quick update letting you know I’m feeling better. I’ll see clients in April, but I’ll be taking it slow and limiting interactions to talking or online appointments only, for now.
My new therapist told me she received these messages while meditating before our first session:
Amen to that!
By Kendra Holliday | February 13, 2022
“Rehabilitation is care that can help you get back, keep, or improve abilities that you need for daily life. These abilities may be physical, mental, and/or cognitive (thinking and learning). You may have lost these abilities because of a disease or injury…” – MedlinePlus
I believe in being open and honest. I’m not in the business of lying to people. I’ve been telling everyone that I’ve been dealing with a family emergency, which is true – but this time, that family member is mostly ME.
I am not well. I am not fit for public consumption.
I can’t afford to check myself into a health spa in a beautiful location, but I can create my own care plan and rehabilitate at my beautiful little fairy cottage.
I wish I had the foresight to plan ahead and take the entire month of March or April off, but instead, I had an emergency happen, and now I have to be reactive, instead of proactive.
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 | January 2, 2022
Here are some of the silly “projects” I’ve done in the past:
Collecting and Reviewing Sex Toys
Nun Striptease (when you click on the link, select “Latest” tab for best results)
Hosting TBK play parties and other specialty events such as Topless Tarot, Crossdresser Tea Party, gang bangs, CFNM, pegging/blow job/fisting/squirting demos…
Sometimes, I look back at my archives and can’t believe I’ve done some of this stuff! Some of it makes me cringe, but most of it makes me feel extremely proud.
In 2021, I counted my orgasms. It wasn’t a contest or a challenge, I was just curious. I’m usually satisfied with one or two orgasms per encounter, whether that’s with others involved, or solo.
Here is the tally:
By Kendra Holliday | December 16, 2021
Confession: My email inbox stocking is stuffed full of inquiries.
Right now, I have about 65 people waiting to hear from me, dating back two months. 🙁 I reply to as many as sweet souls as I can every day, in between sessions and other duties and obligations. (BTW: If you’re waiting for an email from me, check your spam folder. My domain name is blacklisted due to my web host allowing adult content.)
Ideally, I’d like to get back to people within 48 hours, but I’m just one person, and I often get sucked into my menopause mood swings and my dad’s illness – he has mid-stage dementia and I’m his primary care partner. I’ve learned that it is extremely draining to be someone’s quality-of-life support, someone’s seeing eye brain, someone’s backup human being. Even though he lives in assisted living, he depends on me for just about everything.
(As an aside, I’m astonished that I used to have FIVE creatures dependent on me – both my sick parents, my two old cats, and a daughter. All that is left is my dad. I swore to my mother on her death bed that I would take care of him, and I’ve assured him that I will be there for him, for as long as he needs me.)
So all this is to say, I try my best to help others in between my mental health issues and family duties. I’m eager to help people who understand and respect my process. 🙂
By Kendra Holliday | November 30, 2021
Since you asked… here is a list of some of my favorite things:
Wouldn’t it be great if the gas, water and electric companies offered gift certificates? What would be more loving than gifting someone with a hot bath, a home cooked meal, or cooling down/heating up?
Amazon gc – send gift certificates to firstname.lastname@example.org – I looooove books so much! And they sell pretty much everything else.
Whole Foods gc – or Trader Joe’s, Global Foods, Dierberg’s, Schnucks local grocery stores. I don’t eat factory farm mammals or birds, but I do eat veggies, fruit, local, seafood….I love ethnic food like sushi, Indian, Vietnamese, Ethiopian
A donation to
Planned Parenthood – because I believe in accessible health care.
Worldwide Fistula Fund – The Worldwide Fistula Fund is an incubator, funder, and promoter of innovative solutions to improve global women’s reproductive health.
Etsy gc – support artists!
Target gc – I’m a sucker
Flowers – I like when flowers last more like a week as opposed to three days, so the hardier ones are better, though I do like roses and fleeting exotic flowers like orchids. My favorite color rose is the peachy one with blush tones. I don’t like pink as much and I can’t stand the smell of cloying lilies, too funeral home. I keep my flowers in my dining room, which has green walls and lots of colorful jewel tones. Daisies, carnations, sunflowers are great. Did I mention I like colorful?
– I looove soft clothes and blankets!
Shameless Grounds gc – one of my favorite places in St Louis!
Godiva milk chocolate and truffle assortments
DeBrand is even finer, but is based in Fort Wayne IN and worth a goddamn road trip!
Merb’s milk chocolate covered strawberries is local and scrumptious
Soaprocks – these are so cool!
Demeter – they sell so many fun scents, some of my favs are New Leaf, Firefly, Grapefruit Tea, Sushi, Silvery Pekoe, New Zealand, Pipe Tobacco, Leather…
Black Phoenix Alchemy Lab – just look at this website!! I have a scent called Bewitched…
Massage – my baby sis is my massage therapist, she is excellent! You can sponsor a massage for me, or book one for yourself! She’s located in South City. If I know you in real life, I’m happy to refer you.
Victoria’s Secret – I tend to wear L, depending on the style and brand, 36B. My body is average (5′ 4″, 140 lbs) but my mind is extraordinary! I don’t like thongs or g-strings. I prefer timeless and vintage looks over trendy – black, bright colors, jewel tones
I like coffee, tea, and Kombucha.
I’m into oddities, whimsies, cute things, little things, toys…
How about you? What are some of your favorite things?
By Kendra Holliday | November 13, 2021
I have many wonderful clients. One of my favorites is an older gentleman. We’ve been exploring together since 2013!
He’s sweet, considerate, brilliant, generous, respectful, easy going…I love him!
He greatly admires strong, intelligent women – for REAL, he’s not just saying that like so many other men do. His actions match his words.
We usually meet twice a month, alternating between talk and touch sessions. He’s the person I did the Orgasm Experiment with, and he’s a big fan of creative sex.
Usually, our sessions involve me taking on the role of a bossy, demanding woman, such as a stepmother or teacher or nurse. But every once in a while, he tries to get outside his comfort zone and he assumes the power position, such as creepy boss “Mr. Jones.”
Recently, he suggested this roleplay to me:
By Kendra Holliday | October 21, 2021
I caught this exchange on a sex blog the other day:
“Is fisting painful?”
The sex blogger replied:
Two insidious suppositions haunt any discussion of fisting. First, that it will stretch out the vagina to cavern-like dimensions; and second, that it will hurt. Neither is true…
Remove the fist and the vagina does not hang open like the lips of a mouth-breather. It snaps back. Really. Maybe I should post some before and after photos some day?
In the comments, I volunteered to do an explicit photo series, because that’s what occurs to me when I catch wind of something sexually daring, unlike most people who read about it, nod with curiosity, and then go on about their business.
I enlisted my dear friend Rockabilly Girl to do the fisting, and Matthew to take pics.
Get this: I was featured in Hustler magazine earlier this year, and they asked if they could run this photo series. At first I was shocked at the idea, but then I decided it would be pretty fucking cool to rock the fisting in a national hardcore porn mag!
So they made everyone sign releases and submit photo ID’s, including Rockabilly Girl, whose fist is the only thing you see in the pics (until it goes in my vagina).
Then, after weeks of legal paperwork and emails back and forth, Hustler decided against running the pics after all. Too edgy.
But not for me! I think it’s natural, lovely, and intensely beautiful.
So here you go.
By Kendra Holliday | October 17, 2021
I love giving prostate massages.
I’ve done it many times, on my massage table, and on my bed.
Sometimes, the client requests it; sometimes, I suggest it.
It’s good for your health. It’s intense. It often elicits a different kind of release/orgasm.
For some, it can feel extremely pleasurable; for others, it can be more like a soul reboot.
The client arrives clean, meaning they have prepped for anal play by having an enema or emptying bowels. I always check on them when they show up, asking how they are feeling physically, and if they’re still in the mood/headspace for anal play. If they aren’t, we switch gears. If they are, we assume the position!
By Kendra Holliday | August 23, 2021
So, last month, I had a breakdown. I got really mentally and physically ill for a few days. I could barely function – my heart raced, my blood pressure was high, I was sobbing and puking, etc…
This wasn’t my first episode like this – I’ve had a few – due to menopause, hormones, overheating, stress, alcohol abuse, grief, family issues (my dad has dementia), burnout…
This time, I think what caused me to crash and burn was scheduling several intense sessions the week after I got back from vacation.
This is nothing against the lovely men I played with, or the scene topics, but I’ve found that some sessions affect me more than others.
My easy sessions involve surrogate work, TLC, sensual, playful topics.
The more challenging sessions for me these days involve more corporal, kinky, dark fantasies and roleplays. They’re a lot of fun, but they can be very draining, and sometimes it takes me a couple days to recover from the emotional hangover. It didn’t use to be that way – I used to move on quicker. That makes me wonder, is it worth it to me to do these types of sessions? Why do I feel more anxious before some sessions than with others?
I often hear from clients about a Dominatrix they were fond of, but the Domme retired “after a few months.” I wonder why that is? And how do some Dommes make it a decades-long career? Does it depend on their personality? (I’m an INFJ – I feel A LOT).
I decided to read Melissa Febos‘ book Whip Smart, her memoir about being a Dominatrix in NYC for three years. I was shocked and validated by what I read. I highly recommend you check it out.
By Kendra Holliday | August 19, 2021
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.
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.
Here are my biggest turns offs:
Here’s what turns me ON:
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:
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Disregard feelings and safety
Here is how to create a lasting relationship with me:
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment
By Kendra Holliday | July 11, 2021
Disclaimer: I wrote this a long time ago, and it never seemed to fit the vibe of this blog, so I’ve never published it here, or anywhere. It ALMOST made it in BUST magazine, but they chose an essay about male strippers instead.
I was in a very different place 20+ years ago, but since I mentioned it in the post yesterday about Jobs I Have Had, I decided to follow up with this.
Do you know, strippers in 2021 still make the same amount of money I made in 1991?!
I had this gig was when I was 19 (I’m 48 now). I was pretty much trapped in a bad spot – kicked out of my house, no money, no car, dead end job.
I didn’t know what to do. So one day, a girlfriend and I decided to check out the strip clubs on the East Side. I called a place at random, and asked if they hired girls who had no boobs and couldn’t dance. She said sure, gave me directions, and told me to come in for an “interview.”
So I saved up money for a down payment on the cheapest car I could find, and we drove over there.
It was SO frightening entering that place. It was like a haunted house, but it was in the afternoon, and the building sat on a gravel parking lot in Washington Park like an overgrown mobile home. It was called Mainstreet.
Quaking, my friend and I entered. It was really dark, and we had to go up some stairs. There was a bouncer at the door, a 6’6″ black man named Humphrey who directed us to the bartender, who was in charge. She was very tan, busty, and abrupt, and our “interview” consisted of us being taken back to the dressing room, and being told to lift our shirts. I guess she was checking for scars, or a hairy chest or something.
We filled out an application (the whole purpose being to get in writing that you’re 18), and we were hired.
I gave my employer two weeks notice, and soon it was my first day to report to the strip club. I was SOO nervous, because guess what?
I was on my own.
My friend chickened out. (It’s almost unheard of for a woman to just walk into a strip joint out of the blue and get a job there. Women usually wind up there because a friend they party with or relative works there.)
My first day was TERRIFYING. I was paired up with a sweet-n-stupid girl with bleach blond curls and pink lipstick named “Sassy,” who took one look at me and gave me the name “Glamour.” Can you believe that was my stage name?? Isn’t it SO Seven Dwarfs?
She lent me high heels, and for the first time in my life, I got up on a stage and took my clothes off in front of a bunch of strange men 20 years older than me. Can you imagine doing that right now? Can you imagine doing that as a teenager?
We hustled the guys all day, and I went home feeling very dirty and exhausted. And that’s the way I felt for next nine months. I was in my prime and desired by many, but absolutely LOATHED myself.
The strip club I worked at was owned by a nasty man in his 50’s named Tom Venezia, and his 25 yr old son, Milan Venezia. They were SLEAZY all right, and were involved in all kinds of illegal activity, and had loads of money. Milan thought he was hot stuff, so did his dad. They would pick the hardest, bitchiest princess girls and SHARE them, and of course the “chosen ones” thought they were something else, too. They’d run the bar, like the one who hired me.
By Kendra Holliday | June 19, 2021
Here we go again. I thought all my friends, lovers and clients knew, but since I just got ANOTHER ONE… 😫
I do NOT like receiving unsolicited cock shots.
I don’t care if I’m a sex worker.
I don’t care if you got carried away.
I don’t care if I’ve played with your cock.
I don’t care if I’ve had it in my mouth.
I don’t care if you are someone I’ve been fucking with for years, or are brand new and exciting.
I don’t care if you are Barack Obama. (Note: My point is, he would NEVER do that. Anthony Weiner, however, WOULD.)
If you send me a cock shot, it’s like a slap in the face, an instant turn off, and an online assault, and I will fine you $50 and demand an apology if you ever want to interact with me again.
It’s all about comfort and context, people.
I challenge you to comment if you’ve never sent a cock shot, or wish to publicly apologize for sending a cock shot. Or feel completely justified in sending a cock shot.
So, without further ado…
Wanna know the quickest way NOT to get under my skirt?
Think dealbreaker, hard limit, red flag, turn OFF.
OK, besides wearing ugly footwear or torturing small mammals.
Is this what men imagine their cock shot looks like?
Guys. Here is what it really looks like:
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?
See the Arch behind me? 😍 https://t.co/rzqNIczrEB
Covered myself (even my hair!) with Rhassoul clay. My skin feels as velvety as a hairless cat! 😮😻 https://t.co/jUvGvmiECN
Go here if you want to buy my dad’s stuff - dropped off a big box of antique radios, red model cars, etc. It pained… https://t.co/GOVfhx8rzt