Category Archives: My Sex Life

The Task Master

By Kendra Holliday | December 4, 2017

Sometimes, my partner Matthew stops by my place for lunch. And by lunch, I mean eating my pussy and fucking the shit out of me.

I’ll be right in the middle of my day, getting shit done and on a roll, and then he picks me up and shakes me like a snow globe

My life as a snowglobe

I inevitably curl up in the soft blankies, all disheveled and exhausted and ready for a nap!

Obviously, it’s not good for me to be a lazy bitch. 🙁

The last time we had a power nooner, he stood up and dressed, and I did my usual “Lady of Leisure” routine of pulling the covers up over me.

“Oh no you don’t,” he said, tucking his shirt in and buckling his belt. “You’re getting up with me this time. You have to go to the store, so you’re leaving with me.”

Photo by Mike Estes of me impersonating Aileen Wuornos

I whined, I fussed, but he dragged me out of bed (literally – by the ankle) and I stumbled to the bathroom to check the damage.

Oh my fucking god, I looked like Aileen Wuornos.

I started brushing my hair and touching up my makeup, but he came up behind me and announced, “You have four minutes, and then you’re going out the door. It’s up to you on whether you’re wearing pants or not.”

CRAP! Fucking Task Master. It was COLD out, so I scrambled for my clothes and threw them on. I slipped back into the bathroom to make myself more presentable –

“Two minutes.”

UGH! I grabbed my phone, my bag, tried distracting him with aimless chatter…

“Out the door. Now.”

“Let me grab my keys!” I protested.

And then we were out in the harsh light of day.

“There,” he said, kissing me on the forehead, “Now go be productive, My Love.”

I hope I got the pecker tracks off my cheek!

South American Hunter

By Kendra Holliday | December 3, 2017

I knew this sexy 25 year old from out and about. I had chatted him up a few times very casually. I could tell he was a sexual person – he radiated vibrant energy like Ra the Sun God.

Intrigued, I sent him a message and dropped the C Bomb on him.

You know, the fact that I’m a cougar.

Cougar, By Saguaro National Park – Flickr, CC BY 2.0, https://commons.wikimedia.org/w/index.php?curid=31282822

His response? Instantly plugged in.

He knew the game. He responded:

I will be like a South American hunter casting his bow aside to commune with the big cats of the jungle…

I wrote him back:

Well I’d hang on to your spear if I was you – I have claws, you know. 😉

We made plans to rendezvous at his place one night. I told him I didn’t want to talk beforehand, I just wanted to get down to business, and then talk later. He was down with that – he told me he would take me at the door.

I hadn’t seen his face in months, but I was certain he’d be an amazing lover.

I turned on to his street, and the butterflies started flitting in my tummy.

I knocked on his door, and he opened it. I entered. I felt a little shy. I turned away from him and dropped my purse, and he embraced me from behind and started kissing my neck. We had never touched before.

(more…)

Turning Lemons into Lemonade

By Kendra Holliday | November 4, 2017

I was all set to try something new – hire a sex worker for my partner Matthew and me! I’ve been hired countless times myself, but it’s rare I’m on the other side of the equation. Bonus points: My sex worker friend is very different than me. I LOVE contrast! She’s dark, exotic, tall, leggy, busty – and lactates! Mmmm!

I sent her thoughts on what I was envisioning:

90 min session, with about 30 min just talking on the couch connecting, then going to the bedroom and undressing/kissing. You would be center of attention, sweet sensual worship vibe. I’m bi and we’re both very attracted to you. Matthew likes experiencing female energy, exploring a new body, touching and kissing, he loves oral, giving and receiving, but if you don’t want to do oral on him, that’s totally fine. I will definitely go down on him! 🙂 He would like to go down on you if that’s ok. I might sit back and watch, I get great pleasure watching. It would be super hot if he was having sex with me while kissing you. But if we all end up lying around and you being in the middle for a bit, then him being in the middle and us both kissing on him as he gets a handjob…. that is what we are thinking.

She loved the idea!

Photo by Stan Strembicki

We set a date and time. I was so excited to treat her the way I wish to be treated as a sex worker – regard her as an esteemed guest, like a queen, appreciate her rare gifts.

I prepared an envelope with cash – and a tip! – to present her when she arrived, so I wouldn’t forget at the end.

And then, 5 hours before the appointment, she canceled due to illness.

I was SOOOO bummed! Sigh. The more people involved, the harder it is to turn a fantasy into a reality.

But instead of pouting and watching a movie, I came up with Plan B. I was in the mood for something special and super hot!

(more…)

Beaver Cleaver

By Kendra Holliday | November 3, 2017

Thanks to a wildly creative partner, I have a really exciting sex life.

Going under the knife

Going under the knife

Whenever any of my lingerie or stockings gets to the point where it has holes, snags, runs, we like sending it off with a bang. Most of the time, he rips it off of me before having his way with me, but this time, he opted for a little bladeplay.

It was a quiet evening in. My hair was mussed, no makeup, was feeling very submissive and mellow.

(more…)

Robbing the Graveyard

By Kendra Holliday | August 27, 2017

This happened in 2009…I learned some very valuable lessons – the hard way. 🙁

By Rama (Own work) [CeCILL (http://www.cecill.info/licences/Licence_CeCILL_V2-en.html) or CC BY-SA 2.0 fr (http://creativecommons.org/licenses/by-sa/2.0/fr/deed.en)], via Wikimedia Commons

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.

(more…)

A Good Mindfuck

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.

Photo by Mike Estes

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.

A little takedown scene. Photo by Mike Estes

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?

She Let Him In

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.

Violated and shell shocked

“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.

(more…)

How to Eat My Pussy

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.

I love licking Lana!

I love licking!

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.

This was taken in a shady glen in the country

This was taken in a shady glen in the country

Ladies, how do YOU like your pussy licked?

 

Butterfly Threesome

By Kendra Holliday | July 3, 2017

Martin Johnson Heade [Public domain], via Wikimedia Commons

I have a dream girl named Steffy.

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.”

(more…)

I Can Make Your Sexy Wish Come True!

By Kendra Holliday | April 11, 2017

I’ve had this “I Dream of Jeannie” outfit for a few years.

Pretty

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.

Comfy PJs

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!

Like this.

And this.

So after teasing my partner like a matador does to a bull

(more…)

The Good, the Bad, and the Lovely

By Kendra Holliday | December 25, 2016

This chest makes an excellent tuffet

End of the year recap!

Who here is glad to be done with 2016?

WHO?

MEEEEE!

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!

Sun and moon book

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….

Ahhhh!

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?

(more…)

Grab Bag

By Kendra Holliday | November 23, 2016

Just reflecting on how much I get grabbed.

People can be handsy.

My, people can be handsy.

Most of the time I like it.

Surrender

SURRENDER

After all, I have lots of handles.

I have lots of handles

So many handles

Breasts, belly, hips… pussy.

Flesh

FLESH

Of course, I prefer to be grabbed consensually. Like this.

Mmmm

Mmmm

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?

Cabin Advent Calendar

By Kendra Holliday | November 13, 2016

THIS IS OUR NINTH YEAR AT THE CABIN!!!! HEADING THERE IN DECEMBER……….

We disappear here.

We disappear here.

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.

Cuddly like kittens!

Cuddly like kittens!

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:

Maker’s Mark
truck
drunk
gluttony
lust
orgasms
smoke
bourbon cake

hot tub
robes
fireplace
massage oil

Beard.

cum

country music
cabin music playlist
old traditions
new ideas
movies
Deadwood
heat
love
warmth
cock
sex-scented beard
fantasy
roleplay
escape
sleep
connection
spanking
squirm
scream
pain
tears
us
timeless

yes

yes

yes

..

.

HOT Nude Photos From The Cabin

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!

Rustic and romantic!

We took this tasteful version of me wearing a vintage slip for facebook:

I can’t wait to take this slip off!

Then we took these classic nude photos for the blog.

(more…)

Back to the Cabin!

By Kendra Holliday | November 12, 2016

We’ll be sitting in front of this in about 12 hours!

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…..

 

YouTube RSS

Archives

Twitter

TBK365

My daughter’s “Beanie Weenies” cooking assignment cracks me up for so many reasons. Step 4: “Wait til oil ‘shimmers… https://t.co/NNNwjfkjnk

TBK365

All Mother wants for Christmas is her 2 front teeth 🤓🙁 https://t.co/PZr6iwHxSR

TBK365

A shot of my bookshelves. What titles stand out to you? Anything you’ve read or want to read? 🤓📕 https://t.co/LszneoRt6o

TBK365

❤️ https://t.co/AjJieiF0In