By Kendra Holliday | August 27, 2017
Category Archives: My Sex Life
This happened in 2009…I learned some very valuable lessons – the hard way. 🙁I have to admit, I get a kick out of the fact that my partner Matthew is three years younger than me. Still, I have a thing for old men – as long as they have good hygiene and don’t wear old man cologne!
I told Matthew I was flirting with a 76 yr old fellow, and he commented wryly, “There you go, robbing the graveyard.”
Of course that prompted me to take it up a notch, so I found a cute 92 yr old man and sweetly charmed him. He asked me out on a date, and I accepted.
Leonard was born in 1916. Last year he lost his dear wife of 60 years. It’s not the first time I’ve dated a widower.
He’s legally blind, has a hearing aid, and uses a cane. Of course I drove.
I passed a couple people in motorized carts as I walked down the senior living center hallway. I knocked on his door wearing a pretty dress, and he answered wearing a summer suit and tie. I LOVE when a man dresses up for a date. It shows respect.
I asked, “Where’s your cane?”
He dismissed it gruffly with the wave of his hand. “I’m not taking it!”
It was a good excuse for us to hold hands. We were holding hands as we walked into the restaurant. I wonder if people thought I was his granddaughter.
He told me sweetly, “It is a real honor to be on a date with the likes of you. I feel real proud.”
I said coyly, “Is that a snap button shirt, Leonard?”
He said, “Why, yes it is. I find them easy to get on and off.”
I clapped my hands. “I LOVE snap button shirts! Can I unsnap it tonight?”
That cracked him UP. He blushed and said sure.
After dinner we went back to his place. I’ve never partied in a retirement community, so that was a new experience for me.
By Kendra Holliday | August 23, 2017
The other day I tweeted about how I loved a good mindfuck, and a few people asked me what I meant.
A mindfuck can mean many things. It can be finding out the 22 year old Swedish woman you’ve been having cybersex with is actually a 43 year old man from Alabama.
It can be finding out the knife blade your Dominant is running up and down your back as you’re strapped facedown is actually a wooden skewer.
But my favorite kind of mindfuck is one that really challenges me and pushes my limits. When I engage in BDSM activities, I’m more interested in the mental aspects than the physical. I’m not a masochist. I’m a sensualist. I use BDSM play to safely act out the things we’re not supposed to do in society.
We’re not supposed to hit people.
We’re not supposed to pee on people.
We’re not supposed to use people.
We’re not supposed to say hurtful things to people.
But all those primal id desires lurk under the surface. You can repress them, feel guilty about them, or you can use healthy outlets to exercise them. Some people work out, play video games, or leave rude comments anonymously on websites.
I prefer to “work the kinks out” in the bedroom.
Every once in a while, I like being treated like a worthless piece of shit, but it has to be on my own terms, and with someone I trust.
My loving partner is capable of flipping a switch and assuming the role of a hateful motherfucker. This man, who deeply respects me, can unleash some intense wrath on me that leaves me quaking in my boots. I love the moment when his eyes go cold and I feel genuine fear. It’s like riding a roller coaster – terribly exhilarating.
He’ll piss on me, drag me by my hair, use my holes, and tower over me and utter the most unspeakable things – things about my body, things about my past, things about my father and mother – all the things I feel most vulnerable about.
Why do I enjoy this? Because it’s a way of facing my fears. It makes me stronger. It challenges the truth. It penetrates me deeply. It’s incredibly personal and intimate – you can’t do that with just anyone.
I can use my safeword if it gets too intense, and after the scene he administers aftercare, babying me for hours. I love how he can be so fierce one moment and tender the next. I’m in awe of his emotional scope. The resolution is so satisfying – you don’t get that kind of closure in real life. The roleplaying heals old wounds – much better than putting a band-aid on them.
I suppose you need high self-esteem in order to successfully pull off this sort of edgeplay. I wouldn’t have been able to handle it in my 20’s, no way, I was too insecure and soft.
I wasn’t ready to face my fears. I wanted to avoid them. Not anymore.
I’m proud of my personal growth and empowerment.
What about you – what’s your idea of a mindfuck? Do you address your deepest fears?
By Kendra Holliday | July 26, 2017
Ed Note: This is a short story my 16 year old daughter wrote about a young virgin woman being coerced into sex. Nothing like this has happened to my daughter, but I was struck at how much it captured my first experience having sex with a man. I was 16; he was 24. Please be warned that this is an intense piece of writing. A good writer makes the reader FEEL.
“So, you like guys?” asks Tim, grinning, one eyebrow arched high above sky blue eyes.
“Why wouldn’t I?” Tiffany replies, suspicious of the upperclassman’s intentions.
“Well, I’ve never seen you kiss a guy,” he laughs, crow like, a short wheezing sound like a caw. “How would I know?”
“I like guys,” Tiffany insists, pulling up her bra strap. “Do I need to prove it to you?”
“Mm,” Tim purrs thoughtfully, an over articulated sound of dirty thought “Maybe.”
Maybe not, thinks Tiffany hotly, but she has been waiting so long for this. They both have. Tim, she knows, especially. It will be her first time. Tim has been more excited about it than she has, she’s certain, but she’s sure it will be wonderful. It has to be, right? That’s what he told her. His first time was, he said, and he has become very experienced. He’ll show her, he promised, and she knew he would. He’s great at sex, he wouldn’t lie about that. He’ll show her.
“Come on, baby,” Tim pulls her down across the bed by her bare shoulder, laying her across his lap as he reclines, stripped down to his underwear, ill fitting briefs too small.
She doesn’t know this was intentional, but he does. He knows how to present his package perfectly, and she’ll never be any the wiser. It’s not like she’s seen another guy’s penis before. She’ll love it. Tiffany’s name escapes his mind again, but it does not matter. He’ll never escape hers, and he loves it. It was meant to be.
Tiffany sits uncomfortably, finding herself frozen and small in Tim’s warm presence, his personality becoming overbearing and hot the longer she sits in the palm of his hand, undeniably becoming aware that maybe she doesn’t want to be here.
Tim strokes her hair, and she shudders, then tries to relax.
“Are you ready?” Tim asks, and Tiffany finds herself nodding, though her throat clogs, and she is unable to say otherwise.
By Kendra Holliday | July 17, 2017
|The more you know,
the more you grow.
Earlier I posted something on how to suck dick. Since women are more complex, I won’t pretend to know exactly what they all want. Some like more pressure, some like less direct stimulation, etc. But I do know what I want, so listen up! Take notes for our date…
“If her legs ain’t trembling like Bambi, you ain’t eatin’ it right.” – from this HILARIOUS video about eating pussy
1. Start at my head and slowly work your way down. Kiss me, pet me, stroke my hair. Delight in the curves and valleys of my breasts, my belly, my hips, my thighs. I usually like lying on my back to receive your oral worship.
2. Kiss the inside of my thighs. Inhale my scent. Lick up and down my slit.
3. Sure, tongue fuck me and all that good stuff. Then, focus on my clit. The key is the right speed and pressure. Don’t glue your mouth to it. Back up a little to give your tongue room to dance. Pretend you’re a cat lapping cream. Or, gently suck on my clit like it’s a teeny tiny dick – because it is! We all have the same parts down there, just different shapes and sizes!
4. Keep it steady, focus. If you get tired (it might take a few minutes, especially if we’re new to each other) take a breather and kiss on my thighs again, or play with some sex toys, buzzz. But get back to it when you’re ready! And feel free to ask if the pressure/speed is right. And don’t be offended if I offer a little guidance – good communication is key to great sexy time.
5. I like it even more if you put a finger or dildo inside me while you’re lickin’. You can move it slowly inside and out, or just rest it there. The sensation of having something inside is nice enough just on it’s own. I like to feel it when my muscles contract with the orgasm.
6. You’ll know I’m getting close when my legs tense up and I get quiet. And you’ll know when I cum cuz I’ll hyperventilate and erupt with some sexy or primal noise, and possibly grab your head. I might even cry, “You’re making me cum!!!” If we’re in church, I’ll just whisper to you that I’m cumming, so that you know what’s goin’ on, you sent me over the edge, yessss!
7. You can keep it up for a bit afterwards, I don’t go instantly sensitive. And usually after I cum I’m good n’ wet, it’s my fav foreplay, and I’m ready to fuck!
But first, I’ll give you a gold star.
Ladies, how do YOU like your pussy licked?
By Kendra Holliday | July 3, 2017
I call her my dream girl because every time I dream about something, she makes it come true!
Let me give you an example.
The other night she came over for a sweet and dirty little threesome with Matthew and me. We started out with some cocktails and conversation.
Then, we retired to the bedroom, which was bathed in a reddish, golden glow from the mood lighting decorating the walls.
I lounged on the bed as they stood before me. Steffy undergoes the most amazing transformation every time she stands next to big, hulking Matthew – she shrinks! She looks like a little girl, and she gets all giggly, too. She was wearing an adorable fuzzy pink vintage sweater, which made her appear even more feminine.
He circled her like a lion courting a lionness, the way a predator romances his prey, loving, respectful… and with great intent. He tilted her chin up, exposing her neck for him to nuzzle…
Overcome with excitement, I hopped up and wriggled between them and whispered, “I want a Butterfly Threesome.”
“What is that?” they asked.
“I want Matthew to be the body, and for us to be the wings on either side of him, and for him to go back and forth between us, until he finally cums inside Steffy.”
By Kendra Holliday | April 11, 2017
I’ve had this “I Dream of Jeannie” outfit for a few years.
I got it as a hand-me-down from a fancy woman who was downsizing her closet. It wasn’t my style at all (I hardly ever wear pants anymore!), but I loved how flowy and comfy it was – all sea foam green and billowing in the breeze.
I wore it with a white shirt to a concert in Forest Park, right after I got my hysterectomy in 2012. It’s like wearing PJ’s in public.
Now that it’s spring, I got it out to wear it again, and discovered the hanger it was on gave it unsightly yellow stains, so I couldn’t even donate it. It had to be trashed.
But I believe in trashing in style! Anytime I get a run in a stocking or something gets ruined, I don’t just wad it up and pitch it. I let it go out with a BANG!
So after teasing my partner like a matador does to a bull
By Kendra Holliday | December 25, 2016
End of the year recap!
Who here is glad to be done with 2016?
And I didn’t even have that bad of a year – I mainly watched other people’s loved one’s die and shitty world news and election travesty…
I can easily recall bad things, but if I think a little harder, I can conjure some really amazing memories this year –
Going to the cabin
Spending time with people who are no longer alive
Hosting fun events – Shameless Grounds, clothing optional pool party, sex worker workshops, sissy tea party, Fleshtivus!
Road trip with Sex Positive St Louis crew to Chicago CatalystCon
Tantra training in NYC!
A quick jaunt to Texas…
Fun with family – my daughter, partner, siblings and partners are still alive and well
New dishwasher, washing machine, and dryer – so many gifts and blessings thanks to my clients and loved ones
Another trip to NYC and the Poconos!
Lots and LOTS and LOTS of sexy time! Tantra, long distance clients visiting, devirginizing, fetish facilitation and roleplay realized….
And another year of good health – no serious illnesses or STIs, hooray!
And so many loved ones, a roof over my head, food in my belly.
Want to hear something funny?
By Kendra Holliday | November 23, 2016
Just reflecting on how much I get grabbed.
Most of the time I like it.
After all, I have lots of handles.
Breasts, belly, hips… pussy.
Of course, I prefer to be grabbed consensually. Like this.
That was a good night – Ladies Night. I was weak all the next day.
When was the last time you grabbed someone? Did you ask first? Was it consensual? Did it lead to good things?
By Kendra Holliday | November 13, 2016
THIS IS OUR NINTH YEAR AT THE CABIN!!!! HEADING THERE IN DECEMBER……….
I’ve had many couples ask me for the name/location of the cabin we go to. Drop me a line and I’ll hook you up! This cabin is rustic, no wifi, so it’s good to come prepared with food, drink, music speakers, ambient lighting, soft blankets and pillows – we prepare a list every year.
Matthew and I go to the same cabin every winter, and about two months prior, we start getting CABIN FEVER.
A couple days ago, he texted me: “I hope each morning, you’re opening the Cabin Advent Calendar in your head.”
I sure am! Do you want a peek inside? Open each little window and it will reveal:
cabin music playlist
By Kendra Holliday | November 12, 2016
Going back to the cabin next month… looking at the pics from our visit earlier this year with great warmth and fondness… I’m ready for a break from all the madness!
You better believe the pics are hot – we were in front of a roaring fire all weekend!
We took this tasteful version of me wearing a vintage slip for facebook:
Then we took these classic nude photos for the blog.
By Kendra Holliday | November 12, 2016
This is our sixth year going to The Cabin!
It’s our favorite yearly ritual – stealing away right between the holidays and giving ourselves the best gift – time for just the two of us.
For 72 hours, we’ll be living in our own private universe where time and the internet doesn’t exist. In between all the fucking and frolicking, we’ll stoke the fire and eat cake at 2am, watch a movie, float away in the hot womb of the jacuzzi, listen to music playlists that celebrate different aspects of our lives, sip Maker’s Mark hot toddies at 6am…
Previous years have been epic. Last year was a Beethoven theme. Other themes have been BDSM, Ginger, Videos, Western…
I think this year’s theme will be Game of Thrones…
He is my Sun and Stars… I am the moon of his life.
We’ll be far, far away, experiencing something new, and something positively familiar. We’ve had another whole year to strengthen our bond.
Funny how driving four hours from both our houses feels like coming home.
He wrote this note to me four years ago, and it still holds true:
We need a cabin for a weekend together,
undress beside the ashes of the fire.
Your white gown smells of burning leaves.
It’s cold outside but I penetrate you with heat.
I keep you with every inch of my soul.
I love you.
I hate you.
I AM over you, peering down upon you worn and wet.
Reverting to your fetal shape in a torrent of emotion.
I am the man who defines you.
You are the woman who adores me.
A Burgundy box of worthless treasure in priceless proportions.
I will soak the thorny stem I place on your grave.
I am over you, in ALL ways.
We, Dear Slut, are far from over…..
By Kendra Holliday | November 12, 2016
This was our seventh year at the cabin! Such a magical place to reconnect!
The drive there is always fun – we stop in small towns and look for weird and new things to explore. You know, like the world’s largest rocking chair.
One outpost has moonshine tastings – 12 different kinds! We got apple pie and egg nog flavor, which is amazing in root beer.
Cuba, MO has an Amish store where we bought the most amazing cinnamon rolls.
Finally, we arrived at the cabin in the woods, near a lake:
As soon as we got there, he built a fire and made us whiskey cocktails. In celebration, I threw my panties on the fire – I couldn’t help myself! They were kindof ugly anyway. No undies for the rest of the weekend! We mostly stayed in robes or were naked.
We brought loads of pillows and super soft blankets to snuggle up in by the fire. One of them is a fake fur pattern – made me feel like we were in a cave!
I loved stroking the fur, and then my soft tummy, sipping hot toddies and reading gorgeous books, the fire crackling and throwing warm light:
We had an amazingly hot roleplay scene in the hot tub (SEX+STL is giving a roleplay talk today!)
Here is the path leading to the hot tub:
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 11, 2016
This year was the fourth time we’ve been to the cabin, and it flew by faster than ever. The day after we returned I was really grumpy, suffering from cabin drop and feeling very put out that I had to take care of all the necessary duties and resposibilities instead of lying around all tied up in front of the fire sticking ginger up my ass.
Every year we enjoy all the favorite traditions (watching Westerns, building fires, stargazing, listening to Iron & Wine, wearing pajamas or nothing the entire time), but we also like to incorporate something new into our repertoire.
Lately I’ve been on a ginger kick. I love theme events, so I packed a bunch of ginger goodies: tea, men, liqueur, soda, and of course, the root itself.
I was determined to drink the entire bottle of The Big O (“there’s nothing fake about it” ) that weekend (we all have our goals), but I couldn’t quite get there. It started leaving a sickly sweet mossy film on my teeth that no amount of brushing could remove from my ginger-spiced psyche.
We also brought along this awesome vulva ornament our dear friend Rockabilly Girl gave us to hang above the fireplace:
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!