By Kendra Holliday | September 8, 2018
Category Archives: My Sex Life
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.
By Kendra Holliday | July 9, 2018
WARNING: WEBSITE VERY SLIPPERY TODAY. PROCEED WITH CAUTION.
I DON’T THINK I CAN WRITE THIS REVIEW WITHOUT USING ALL CAPS. (deep breath) OK, I’ll try. Here goes…
Remember this post: Matthew emailed me this porn clip featuring “nuru massage” and said.
“This is absolutely going to happen.”
It finally did.
Back then, we had no idea what this Nuru gel was all about. We wondered if it was a gimmick. Surely it wasn’t as fantastic and flawless as the website claimed:
“The nuru gel is made from deep seaweed (Nori) and is transparent, tasteless, odorless, extremely slippery and smooth.”
But hey – guess what?
It was amazing. Incredible. Exceeded expectations. It made for a very special evening. It’s like a spa workshop for couples. It was like an adult waterpark. It was JUST LIKE THE VIDEOS. Except I’m not a super hot Asian chick.
Here’s what you need to do:
That’s right, snatch up that boring ugly looking bottle. Don’t judge a book by its cover. Might as well get two while you’re at it, cuz you’ll want to do it again in a couple months. Or sooner if you get really turned on touching flesh like you’re a blind person who just got out of solitary confinement. Or like you’re a starving lion and your partner is a steakumm. Or like you’re an over-the-top hedonist sensualist at the Playboy mansion with a bottle of Viagra.
By Kendra Holliday | June 22, 2018
You know you’re in a sex-positive environment when a woman can doze off nude on a day bed outdoors by herself, and not worry about anyone molesting her.
And, of course, at other times you can see a bunch of people fucking in every one of the beds, in all sorts of fun combinations. That’s also very sex-positive.
My week at Desire with the Life on the Swingset crew was better than I imagined it would be. And I have a pretty good imagination!
I was nervous and excited to travel all by myself to a couples only lifestyle resort in a different country. I only knew a few of the people who would be my naked neighbors for the week (out of 120 rooms, the Swingset had booked 88 of them – next year, they’re booking ALL of them!) But I was determined to embark on this adventure with a positive mindset – after all, what did I have to lose? Just my clothes!
As inspiration, I brought this book along with me on audio – it’s all about discovering your personal legend, and has great quotes such as, “There’s a language in the world that everyone understands – it is the language of Enthusiasm – of things accomplished with love and purpose, and part of a search for something believed in and desired.”
I highly recommend it!
When I arrived, Cooper gleefully greeted me naked, with an espresso martini in hand.
The staff served me a glass of sparkling wine and a cool towel to refresh myself from my travels. I would continue to drink sparkling wine for the rest of the week! And other cocktails, and sushi, and guacamole, and cake, and lord knows what else! Eat, drink, and be merry!
I made a name tag charm necklace (helpful when you aren’t wearing clothes!) – it’s my Twitter header.
— Kendra Holliday (@TBK365) November 9, 2015
After my necklace was made (festooned with love and good charms!) I stripped naked and joined the group. A super nice couple gave me a tour of the resort. It’s not very big, but it’s laid out in a meandering fashion, right on the beach. Speaking of, my room had an ocean view!
By Kendra Holliday | June 2, 2018
This dress? I’m sick of it (but thankfully I’m NOT sick of David Wraith!)
It was a loud print, slinky number I got from H&M a few years ago for $30.
Here I am, getting spanked by a big man, back in 2009?
It got some holes in it that I couldn’t figure out how to repair, as the dress was such a wispy material. So one night, I decided it was time to retire it. I couldn’t donate it to Goodwill, so instead of tossing it in the trash (yawn!) I decided to enlist a straight man for some fun. I did the equivalent of waving a red flag at him:
By Kendra Holliday | January 31, 2018
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.