By Kendra Holliday | January 31, 2018
Category Archives: My Sex Life
Do you know the term “New Relationship Energy“? It’s popular in polyamory circles, and describes that giddy infatuation feeling when you’re dating someone new. It’s like a drug!
My daughter is experiencing it now as she’s dating a new boy. They are so crazy about each other! It’s so nice to find someone who is your champion, someone who makes you feel emotionally supported and loved – someone who gets you, despite all your idiosyncrasies.
I’m about to head out for my 10th cabin getaway with my partner Matthew. As I sit and reflect on how crazy we still are about each other after all these years (a record for me!), I appreciate how our connection has evolved into Old Relationship Energy. (Read this great list of ways to keep the spark in your relationship. And if you’re more monogamous-minded, do check out Esther Perel’s work on how to sustain a happy and healthy marriage.)
I remember the first year or two we were together, we had to have sex at least twice a day. If we were lying in bed together, he would be hard. We would have threesomes and foursomes all the time. It’s not like that anymore, but we still feel passion, deep connection, and mad respect for each other. We don’t have sex as often as we used to, but it’s still realllllly good.
Here is how we have maintained a decade of great emotional and physical fulfillment, despite all the challenges we’ve faced:
We chose not to live together or combine our families. We have our own space and don’t have to go to family therapy!
- We didn’t get married. Been there, done that!
- We keep our finances separate.
- We maintain independence and autonomy.
- We share many core values, but are two very different people with different interests, so while we do some things together, we have no problem traveling solo or supporting each other’s endeavors.
- The time we spend together is quality time. We carve out date nights and little adventures. Novelty is exciting!
- We realize that a healthy relationship is give and give. I’ll never forget how he took care of me during my times of need, and I’m always thinking of ways to reciprocate.
- We do relationship check-ins as needed.
- We allow each other freedom to be romantic and sexual with other people. Every time we experience another person’s energy, it gives us a libido boost.
So, basically, we’ve rejected all the typical trappings of a long term relationship that can cause stress and resentment to build. People used to ask us, “When are you getting serious?”
Maybe I should have replied, “When are you getting playful?”
It’s much more fun to think – and play – outside the cage!
By Kendra Holliday | January 18, 2018
My friend has been 30+ days sober, and he’s been drinking a lot of tea. So have I!
So he asked if I wanted to join him for tea at the London Tea Room sometime, and I said YES, I would love to, but how about if he came over to my place for tea, and I would serve him tea topless?
He said he has never had tea served that way before, and thought it was a grand idea!
I figured this would be a good precursor to my London trip in March. 😉
When he came over, I greeted him at the door wearing this:
(Spoiler alert: he did not cover me with his cum. He covered himself with his cum. With my help.)
I took off the shirt to reveal this cute lingerie
By Kendra Holliday | December 23, 2017
After our spontaneous threesome the other night, I was SO eager for the three of us to get together again! I’m so greedy! I want more more MORE!
Lana came over, and we sat on the back porch and talked over cocktails, relaxing and catching up.
After a while, he asked her if she was down to play that night, and she said yes!
I love her hazel eyes, her bountiful hair, and pert nose. I’m a sucker for pert noses! She has such animated facial expressions, and tells such funny stories. I love her mannerisms. Very mischievous eyes. Also, she has an extremely smooth butt. It’s like really cute butter.
This time, he drew a bubble bath for two! We both easily fit in the tub. He gave us our girl time to sit and talk. He checked in on us, brought us drinks, it was wonderful!
Then we sat on the couch for a while to cool down, the two of us naked with towels.
He led us up to the bedroom, which was bathed in the golden glow of a small, bedside lamp. The king-size bed was adorned with chocolate brown sheets. Mood music played softly in the background.
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 Matthew | December 22, 2017
Ed Note: Here is Matthew’s perspective of the sexy story I posted earlier this week! Another first date success story from the pages of polyamory…
Having been acquainted with this woman for almost a decade, I was happy she contacted me after her recent relationship ended. Here’s how it transpired….
“I need your help,” she blurted.
Aside from seeing her a couple times out and about, that’s the first message I received from her in more than year. I wasn’t quite sure if she needed help moving, or help with her taxes, or maybe some direct pressure on a wound?!
“Okay, but I’m gonna need more details here,” I replied.
“I need someone…”
“Go on,” I encouraged.
“Okay…I need a fuck buddy. Does that even exist? Is that weird?”
“Now we’re getting somewhere. Yes, it exists, and it is absolutely NOT weird!”
The conversation went on from there with me reassuring her that everything she wanted was totally acceptable. I asked her if she had a preference as far as type of person. Male? Female? Brown, white, yellow, big, small, old, young?
“No. I’m really not picky. I just want someone to hang out with, experience some culture, have some drinks, and have sex with no guilt, no drama and no real expectations. Knowing you….I figured you might know where to look.”
To which I replied, “Sounds perfect. How about I start with looking in the mirror?”
“I’m totally interested!” she exclaimed.
Yes!! I’ve always been attracted to her, and received great feedback from her to my flirtatious cues in the past. Now, the timing was finally right. She was well aware of my relationship status, yet still contacted me. That is a major factor in my choosing to see women for anything more than a platonic connection.
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
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.”
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 –
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!
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.
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.
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!
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!
By Kendra Holliday | November 3, 2017
Thanks to a wildly creative partner, I have a really exciting sex life.
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.
By Kendra Holliday | August 27, 2017
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