By Kendra Holliday | February 3, 2019
Category Archives: My Sex Life
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 | December 13, 2018
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 | December 13, 2018
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 | December 12, 2018
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 | 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.
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.