By Kendra Holliday | May 6, 2022
Category Archives: My Sex Life
The other day, a friend I’ve known for years texted me out of the blue:
“Hi Kendra! After years of celibacy, I’m finally having sex again! He’s amazing. We want to experience many things together, can you give me advice on hiring a sex worker for a threesome?”
I was so excited for my friend! I let her know about these sites they could explore together, as well as searching twitter using keywords, such as #STL #GFE #datestl, (be sure and click on “latest” tab at the top):
I told her that if a couple is looking to hire a sex worker, it’s better for the woman to initiate contact, as that shows the worker she’s involved in the process and not being “dragged along.” I advised her to read the website instructions, and expect to be screened and pay a deposit.
By Kendra Holliday | January 2, 2022
Here are some of the silly “projects” I’ve done in the past:
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 | 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 | March 1, 2021
Ed Note: This post details my personal experiences with sexual trauma.
I’ve been with hundreds, if not thousands, of sexual partners. Some have been AMAZING, and most have been good. A few have been BAD, and a few have been ugly.
To be clear, I’m an experienced professional, and based on what my partner is seeking, I try my best to deliver. Some men want an entertaining diversion, a frolicsome romp into the realm of female energy. Some men want to learn how to be good lovers. Some men want validation and healing.
I usually use a soft, sexy voice to instruct and redirect: “Gentle, please. Oh yes, I like that.” Sometimes, I choose to endure irritating groping, or I’ll grimace my way through a dry fingerbanging, the man treating my vagina like a chainsaw he’s priming. Occasionally, I’ll exclaim “ouch!” or a stern “No!” if, for instance, he’s trying to stick it in without a condom, but for the most part, I don’t want to spoil the moment or damage his confidence.
All that said, here are three times I straight up screamed during sexy time:
1. Years ago, I was on a date with a man. He was going down on me. I was lying there, relaxed and feeling good, when all of a sudden, he bit down hard on my clit!
I screamed! WTF?!
I gasped, “Why did you do that?!”
He replied, “The last woman I was with liked when I did that.”
Are there any women reading this who like having their clit chomped on? I’m sure some do, but most DO NOT. Always err on the side of caution when experimenting with sensation. Ask for preferences. Go slow. Start with less pressure or sensation and watch for body language and feedback.
I never went near this man again. I associated him with distrust and pain.
2. In 2018, I was going through a rough time, so I was distracted and my defenses were down. I agreed to let a young man from Indiana visit me for a session. I had screened him with a phone call, and he had given off some weird vibes. Normally, I never agree to be intimate with someone sight unseen, but like I said, I was in a bad place and grieving a loss, so I gave less fucks.
As the man drove hours to St Louis, I felt mounting dread. I had asked him what he was into, and he replied ominously, “You’ll know when I get there.”
I was so nervous by the time he knocked on my door. I took a deep breath, and opened the door.
By Kendra Holliday | November 19, 2020
Let’s get this cleared up right off the bat: Do you wanna know what it feels like to be penetrated non-consensually?
LIKE YOUR SOUL IS DYING.
So don’t do that. DON’T penetrate other people non-consensually. I can’t believe I have to state the obvious. COME ON, PEOPLE.
Now, let’s move on to how it feels to be vaginally penetrated when you are into it, turned on, etc.
I posed the question on fb and twitter, and got responses from several curious men, but only one from a woman! My friend, Bianca:
“Being penetrated vaginally feels like a void is being filled. Like the right jigsaw piece is in place. Like warm candy. So good you roll your eyes up with pleasure.”
Let me elaborate.
It’s like tucking into this gooey, decadent, absolutely delicious dessert, all sweet and salty and creamy.
It’s like you have a throbbing headache, and someone slips you morphine. Hot, throbbing morphine, for your hot, aching pussy.
It feels like a drug that will save your life.
It feels completely base and primal, like you want to fuck the earth and fill your womb.
It feels the way a spring crop looks, all those new green shoots pushing up through the moist, fertile black soil.
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.
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.
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!
By Kendra Holliday | September 26, 2019
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….
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.
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.
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!
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.
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.
By Kendra Holliday | July 3, 2019
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.
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,
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!
By Kendra Holliday | February 3, 2019
Ed Note: This a guest post by my good friend, Gigi Spanks!
I have always been a shy and reserved individual. I grew up in a conservative household where girls were expected to be polite and behave, and there was virtually no talk about sex. After my first sex ed class in 5th grade, my mom sat me down to watch a National Geographic episode about sex. The only thing my father ever said was, as I was on my way to college, “You better not get pregnant until you have your own health insurance.” Needless to say, I had no language or skills to know or ask for what I needed as a sexual being.
My first orgasms were exercise-induced and I had no idea what they were aside from an exquisitely pleasurable sensation that flooded through my body. I saw porn for the first time on TV while on a school trip to Europe, and that is how I learned to masturbate. In high school, I had a few fumbling relationships with boys, but we didn’t get past second base. I remember one particularly frustrating encounter in which I was trying to coyly hint that my high school boyfriend should move things along and grab my tits, but apparently we weren’t on the same wavelength because when I said “Go for it,” he paused and said, “But I don’t have a condom.”
It wasn’t until I met my future darling husband (DH) in college that my sexuality began to blossom. He knew how to make me cum and taught me many things. Our first time having intercourse was amazing and an experience I will always remember. Despite all of his love and encouragement, the conservative attitude with which I was brought up persisted and limited a lot of the activities in which I was willing to participate.
Things started to change when we found out one of our friends was a boudoir photographer. She took amazing pictures of women… I dragged my feet on going because I was overweight and had body image issues, I would go when I had lost some weight.
When I found out I was pregnant with my first child, I thought, I better go now, I will never look as good after I have kids. So I went and had one of the best days of my life. I got a make over, dressed in sexy lingerie and was treated like a princess – I felt sexy as fuck. When DH came by later that day to help select the images my feelings were confirmed as I watched his jaw hit the floor. For the first time in my life I felt absolutely beautiful!
Six months after our son was born, DH approached me about attending a play party hosted by The Beautiful Kind. I agreed with a little apprehension, as the most risqué thing we had ever done was go to the strip club and walk through the Red Light District of Amsterdam.
We decided to start out easy with a happy hour hosted by Sex Positive St. Louis, so we could meet hostess Kendra Holliday and some of the other individuals we might meet at the party. I am usually very awkward at social events, but everyone was so welcoming and friendly! We had such a great time, we decided to attend Kendra’s party.
By Kendra Holliday | October 24, 2018
Ed Note: I’m so glad I captured the first time my partner Matthew and I made love…this was first published in Nov 2008. Celebrating 10 years of love!
We are sitting on the couch where we had our first Cuddle Movie night six months ago. Soft music is playing, a candle is lit. We’ve spent the past couple hours talking, updating his online dating profile, catching up. We are terrific friends, but I want more than that. I sit close to him, but really I want to crawl right inside him – I can’t get close enough.
I watch his every move hungrily and shyly – I pay attention to how his great hairy arm flexes as he cuts into a tight, round pluot streaked with red and orange with a paring knife. He balances a slice on the end of the knife, looks me in the eye, and offers it to me.
I reach to take it, think again, lower my hand, and allow him to insert the knife inside my open and waiting mouth.
“Careful,” he whispers as the fruit slides off the blade. I bite down on the sweet, firm flesh.
He switches to hand feeding me, and his fingers touch my lips. I feel like a baby bird – at least, inside I’m clamoring, frenetic…
He finishes feeding me, sets aside the plate, and puts a paw on my neck and kneads it.
“You’ve got a knot,” he murmurs. “Come down here,” he gestures to the floor in front of him, and I kneel facing away from him. He rubs his rough hands together rapidly to generate heat. I close my eyes as he lays those hot hands on my neck…the back of my head…and works my kinks out.
He takes one of my braids and slides off the band, then loosens it. My hair spills silky through his fingers, falls loose down my back…he undoes the other. My head tingles at the gentle ministration.
Love washes over me.
I can’t stand it anymore. Even though I am nervous, I stand up, face him, take a deep, shuddering breath, and climb onto his lap. I straddle him like a horse. I almost expect him to shove me away, it’s like a dream, too good to be true, but he allows me melt into him…
By Kendra Holliday | September 8, 2018
I meekly knocked on his door.
He opened it. He was huge, imposing. He intimidated me with his silent strength. He had gleaming curls and his cheeks were rough. He was like a great big bear, so powerful. He gazed down at me.
Wordlessly, he ushered me in.
I did not know it, but he was a King.
He drew me a bath. He brought me his robe to wear. I replaced my worn cloak with his clean robe. I swam in it, the hem brushed the ground.
As the bath filled, he sat me on his lap and listened to me tell him of the places I had been that day.
I was so tired, so grateful.
He held my hand as I eased into the hot, fragrant water. Melting, I soaked away all my worries.
When I was ready, he stood me up and draped my wet body, and led me to his bed.
I slipped the robe off and slid gratefully into the bed. It was piled high with soft bedding, and smelled of spices and herbs. I snuggled down and effortlessly drifted off to sleep. He left me to rest.
I was awoken by him getting into bed with me. My body prickled at his nearness. I could smell him.
He pressed his body up against me, and put his big arms around me. He pulled me into him. He breathed in my ear. I shivered.
He caressed my curves. He kissed my breast. He worshiped me.
He said, in low, measured tones:
By Kendra Holliday | July 14, 2018
Last week, I posted about a fantasy I wanted to make happen in real life with Matthew and Lana.
Today, I detail how things really went down. You be the judge – which is hotter, the fantasy, or the reality?
First of all, my fantasy included cum play and cream pies, which involves risky behavior. All parties need to trust each other and get tested.
So, we did.
The day of our date, Lana texted us the good news about her test results:
Now we were ready to make it happen! We were all SO excited – the fantasy matched each of our desires perfectly. Anticipation served as foreplay all day – all week, really.
The evening started with us chatting over drinks and catching up. Matthew warned her that he hadn’t been inside a pussy for 21 days, and hadn’t busted a nut in three days, so things could get crazy fast.
Sure, we were throwing down, but we were doing so in style. Candles were lit, and romantic Brahms played in the background
I wore a neutral, mesh teddy that accentuated my curves and nipples. She wore a short little black teddy with pink lip prints all over it.
He started things off by cuffing my hands behind my back. I tried resisting just for fun, but it was like slicing into soft butter with a sword – no contest. He had me locked down firm, then gave me a sweet kiss on my quivering lips, and tied the small, silver key to one of the strings hanging off the teddy’s neck. Then, he sat me down on a small tan tuffet at the foot of the bed, fashioned from a folded blanket. I was out of the way, and in position. He murmured, “Sit. Watch. I’ll be back.” I obeyed, like a well-behaved puppy expecting a treat. She stared at our exchange, wide-eyed.
Then, he turned his attention towards her. She stood there, looking up at him expectantly. He kissed her, hands roaming over her body, caressing her breasts through the gauzy fabric of her teddy. He spun her around and kissed her neck and shoulders. She moaned slightly as he pressed his swollen cock against her soft panties. He pulled her lingerie off, caressing her now exposed nipples, kissing her neck hungrily until she almost came. He stopped short of her explosion….
By Kendra Holliday | July 13, 2018
The other night, I witnessed my friend Lana have her first MFM (Male/Female/Male).
I sat in a chair at the foot of the bed, fully dressed, wrapped in a soft blanket, goblet in hand.
I felt like this:
She, on the other hand, was naked and blindfolded on the bed, being worked over by two muscular, horny men. She looked so gorgeous and vulnerable in the warm, dim glow of the bedroom chamber.
I pretended that I called for them and that this was my entertainment of choice for the evening – to watch a lady-in-waiting get stripped of her gown, used, and impregnated.