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 14, 2018
In my last post, I told you about a twisted, romantic fantasy I had, and how we were going to act it out in real life with Lana. Today, I am posting the fantasy. Next week, I will post how it played out in real life. How did it match up? How was it different? Which is better – the fantasy, or the reality?
Here is what I have in mind for us to do tonight.
You set the scene, and get me situated. I’m kneeling on the bedroom floor, naked, hands cuffed behind my back. Normally, I’m very much involved in our powerfully charged sex acts, but not tonight. Restrained, I can only quietly observe what is about to transpire.
Then, I watch you seduce beautiful Lana, standing there, kissing, hands roaming. The room is dimly lit, it’s romantic, you’re focused on her, I’m a fly on the wall.
Next, I imagine you in bed together, a sheet over you, seeing your big, bristling, muscular shoulders and chest compared to her smaller frame.
Her hair is all wild, you’re lying there kissing. You do whatever slow foreplay, oral or whatever, but I imagine you sucking on her breast as she gently tugs on your cock.
She wants it.
Your cock is STRAINING and finally you can’t wait any longer, and with a gentle growl, you push her legs apart with your thigh. You have to be inside her.
Now is the time.
You push and coax your way in, she readily receives you, she’s so hot and soft, finally you two are plugged in, skin to skin, snug. You’ve already made her cum, so that is not the goal here. Sure she can enjoy it, but this is for you, so you can finally fill her with cum and mark her, after knowing her for more than a decade. You’ve been biding your time, waiting for the right moment, but who would have known the right moment would involve the love your life being witness to this sacred act?
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 | July 7, 2018
So, we’ve been dating this sweet ‘n sexy couple for the past year or so.
It’s been very slow going because we’re all so busy. We finally realized we had to carve out time with each other in order to have special dates, so one week I went out with the husband, and Matthew had a date with the wife a couple nights later.
Let me tell you about my date first – he was such a gentleman!
I wore a pretty, silky jade dress. I felt a little nervous! I was excited to finally have a chance to talk and bond with him in an intimate manner. We had sex once before, months ago, but it was a totally different feel – anonymous and clandestine, with no words exchanged. So even though I had a sneak preview of his prowess, tonight felt brand new.
He came to my door and knocked, presenting me with a bottle of wine and a bouquet of lettuce greens from his garden! He complimented me on my dress and opened the car door for me.
We went to The Fountain on Locust for drinks and dinner. He knew right where he was going, and I didn’t have to worry about a thing!
This was our first chance to enjoy one-on-one quality time with each other. He made me feel so special. I was in a delicate, feminine mood that night. He asked me questions and listened thoughtfully as I babbled away about all kinds of things. He had such a confident, gentle demeanor.
The Fountain served us AMAZING ice cream martinis, which we kept sampling throughout dinner. Our server was amazing and added some electric energy to the atmosphere. His intensity made me blush when he took our drink orders. I love the decor, too – all blue and gold, art deco.
When we got back to my place, he went to pour two glasses of wine for us. When he returned, he found me wearing only lingerie – I couldn’t wait to slip my dress off!
By Kendra Holliday | July 2, 2018
Since you asked… here is a list of some of my favorite things:
Cash, of course!
Wouldn’t it be awesome if the gas, water and electric companies offered gift certificates? What would be more loving than gifting someone with a hot bath, a home cooked meal, or cooling down/heating up?
Amazon gc – send gift certificates to email@example.com – I looooove books so much! And they sell pretty much everything else.
GiftRocket online gift card – versatile and easy!
Whole Foods gc – or Trader Joe’s, Global Foods, Dierberg’s, Schnucks local grocery stores. I don’t eat factory farm mammals or birds, but I do eat seafood, veggies, fruit….I love ethnic food like sushi, Indian, Vietnamese, Ethiopian
A donation to
Planned Parenthood – because I believe in accessible health care.
Worldwide Fistula Fund – The Worldwide Fistula Fund is an incubator, funder, and promoter of innovative solutions to improve global women’s reproductive health.
Etsy gc – support artists!
Target gc – I’m a sucker
Flowers – I like when flowers last more like a week as opposed to three days, so the hardier ones are better, though I do like roses and fleeting exotic flowers like orchids. My favorite color rose is the peachy one with blush tones. I don’t like pink as much and I can’t stand the smell of cloying lilies, too funeral home. I keep my flowers in my dining room, which has green walls and lots of colorful jewel tones. Daisies, carnations, sunflowers are great. Did I mention I like colorful?
Soft Surroundings gc – I looove soft clothes and blankets!
Earthbound gc – hippie fashion!
Shoes – size 7, no sandals
Mystic Valley gc – for my witchy things!
Cheryl’s Herbs gc – more healing magical opportunities! I got a scent there called Goddess…
Shameless Grounds gc – one of my favorite places in St Louis!
Godiva milk chocolate and truffle assortments
DeBrand is even finer, but is based in Fort Wayne IN and worth a goddamn road trip!
Merb’s milk chocolate covered strawberries is local and scrumptious
Soaprocks – these are so cool!
Demeter – they sell so many fun scents, some of my favs are New Leaf, Firefly, Grapefruit Tea, Sushi, Silvery Pekoe, New Zealand, Pipe Tobacco, Leather…
Black Phoenix Alchemy Lab – just look at this website!! I have a scent called Bewitched…
FLOAT gc – I love FLOAT, it’s like being in the womb, getting a massage without being touched. You should try it, too!
Massage – my baby sis is my massage therapist, she is excellent! You can sponsor a massage for me, or book one for yourself! She’s located in South City. If I know you in real life, I’m happy to refer you.
Victoria’s Secret – I tend to wear L, depending on the style and brand, 36B. My body is average (5′ 4″, 140 lbs) but my mind is extraordinary! I don’t like thongs or g-strings. I prefer timeless and VINTAGE looks over trendy – black, bright colors, jewel tones
Liquor – Bombay Sapphire / Beefeater / Tanqueray gin, Maker’s Mark whisky, bourbon galore, Ketel One / Grey Goose / Belvedere / Sobieski vodka, Kraken rum, American Honey, peach brandy, Chardonnay, champagne, or any other premium liquor brand you want me to experience
I also like coffee, tea, and Kombucha.
How about you? What are some of your favorite things?
By Kendra Holliday | June 27, 2018
|Who’s Afraid of the Big, Bad Breast?
(ok, not really big, and not really bad!)
“Boobies are not Nazis!” my daughter exclaimed, when I told her about the woman in New Jersey who crusaded for the right to sunbathe topless and lost her bid after an appeals panel ruled breasts as violating “the public’s moral sensibilities.”
If female breasts threaten society’s morals, does that mean the people they are attached to are a threat as well?
When I posted this story on facebook, a woman sadly commented: “Laws are made for the people, not by the people. This truth is an unfortunate circumstance. Because women tend to have more fat cells and the presence of mammary glands in their breasts, we cannot enjoy the same freedoms as men.”
Meanwhile, my friend posted this status on facebook the other day:
“pet peeve: when parents force their toddler daughters to wear a bikini top at the beach. It’s the last time she’s not breaking any laws. Let her be.”
One of MY big pet peeves is the fact that men are allowed to go topless in most of the United States, but women are subject to arrest.
Why is this?
A possible theory on why women aren’t allowed to go topless: because erect female nipples are a symbol of sexual arousal and readiness, which freaks men out. Even wearing no bra can be an issue.
A guy friend of mine asserts that it’s the female areola that is the problem, not the nipple itself.
By Kendra Holliday | June 23, 2018
As you probably know, I’m not a size queen. I’m a fan of average size penises. Bigger dicks can limit options!
So when a company a while back asked me if I would try out a penis extender device, I passed. It was too Frankenweenie for me.
But recently, I learned of another product that can be used with big dicks – The Bumper! The Bumper is good for those who are plumper – down there.
Here is some info from the website:
When it comes to sex and relationships we know you’ve probably heard and seen it all. That’s why we would like to throw something new your way- the Bumper from Perfect Fit.
The Bumper is the first-ever adult product that cushions deep thrusts during intercourse, providing an opportunity for more passionate sex without restraint to put it simply…. more cushin for the pushin’.
Comprised of ultra-soft material and made of a two-part system: The Bumper™ Thrust Buffer™ and the Donut Buffer. Either one can be used independently or together to create a thick and protective cushion for when the thrusts get deep-absorbing some of the bumping and providing the sensation of maximum depth for the penis.
I’ll be honest – I was VERY skeptical. It looked unwieldy and impractical, not very sexy. Here’s what it looks like out of the box:
But I was intrigued, so I decided to give it a test drive.
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 Matthew | June 17, 2018
Ed Note: This is a guest post by my partner, Matthew. He is the father of two children.
A couple of weeks ago, I started hearing the yearly buzz of “Father’s Day” gifts, salutations and tributes. I started thinking a bit more in depth on the subject of Fatherhood and what it means to me.
Being a Father is synonymous to me with being a man. I hear so many people speak of “men” they know or have connections with and then start divulging details about these people.
I know women who demand flowers from their husbands as a way of apologizing for an act of relationship treason.
I know women who are dating “men” right now, but speak of nothing but their shortcomings.
I know of “men” whose wives have gotten up and walked away from them while they were eating her pussy.
I know of “men” who don’t make an effort to spend time with their children.
I know of “men” who can’t separate business from pleasure and vice versa.
I know of “men” who are so weak themselves, that they show their “strength” by preying on the eager and ignorant.
I know women who have settled for a “man”.
I know of “men” who live in their mother’s basement.
I know of “men” who can’t dress themselves.
I am sure you know plenty of “men” like this as well.
If a man has children, they are his number one priority.
By Kendra Holliday | June 8, 2018
So many men are sick from toxic masculinity in our society. They have to be very manly, which involves taking care of business, being in charge, hiding feelings, and burying their feminine side.
Yet, they crave a place where they can surrender to a strong, sexually confident woman and be awash in female energy and power exchange. They want to be cared for. They want youthful female energy. They want mature female energy.
So they contact me requesting help with exploring their sexuality, but then proceed to railroad me and call the porn shots and trample all over the sensual process and fuck it up. So frustrating!
Here’s a Dan Savage podcast where a man wants to know how to get his vanilla wife to like domming and pegging him. Go to the 8:35 mark and listen.
Dan points out that for some women, this can feel more like work than fun, so he suggests backing things up. For a woman not used to being sexually dominant, a good place for her to start is to think about what she wants right now and demanding it.
But what if what she wants right now is a cup of tea? Will that disappoint her partner? Will taking small steps like this lead them to a place where they both feel fulfillment?
I get a lot of men who tell me, “I want to please you.”
But then, when I tell them what I want, they steer things back to what THEY have in mind.
If you want me to peg you, piss on you, sit on your face, objectify you, humiliate you, rub your naked body while you talk on the phone, that’s totally fine! You’re hiring me to perform a service, and I am happy to oblige. I have so much fun being creative sexually! I like taking care of you.
But don’t get it twisted. Are you doing this for you, or are you doing this for me?
Prepping for a session takes work, so not only are you paying for the time we are mentally and physically engaged, but you are paying for the hour before and after. I have to dress up in uncomfortable lingerie and heels and get into the right head space. I have to clean up afterward.
If you REALLY want to please me, here are some ideas:
By Kendra Holliday | June 6, 2018
In my experience, sex partners are few and far between. When I do find a partner, relationship drama soon kicks in, and that tarnishes the fun in having sex. I’ve always wanted more sex with more women without all the hassle – a life of sexual freedom and openness, and the joy that comes with it. But alas, it always eludes me.
I appreciate your blog and lifestyle, and I’d like to live a sex life similar to yours. I want to enjoy a sex life with an abundance of attractive women, with a consenting partner, in a way that good partners come towards me without all the games.
I’ve always felt that the key to living the life you want is your mentality or perspective about it. And so my question to you is, what is the mindset of one who lives this sort of life, or the spiritual perspective? What kinds of thoughts prohibit one from living the life? What is the secret to living an abundant sex life?
There is one main thing keeping people from celebrating their sexuality in a free and fun manner – FEAR.
If there’s one thing I’ve learned from traveling to other countries, it’s that USA is a very fearful country. We are rife with anxiety and depression, due to all the limitations we impose upon ourselves. And yet, we tout ourselves as a free country.
HA. Very funny. Nice try.
I highly recommend you read The Bonobo Way by Dr Susan Block.
And Decoding Your Kink by Galen Fous MTP.
And, it looks like some of my other book recommendations have helped people! See this heartening note from a reader:
“You and I could probably agree on very little…I’m a Conservative Christian male, in a monogamous relationship with my wife, and I was a virgin until I was married.
And yet, my wife and I have had intimacy issues for many many years. I stumbled onto your site and, at after seeing your Top Sex-Positive Recommendations post, started reading Robert Glover’s book ‘No More Mr. Nice Guy!’. I thought I was going to see my picture in the pages of that book. Almost everything in that book described me perfectly.
Then, also at your suggestion, I started reading ‘Open Her’ by Karen Brody. Not finished with this yet, but again I’m seeing eye-opening revelations.
My relationship with my wife is improving, but I have miles to go before I truly overcome my ‘Nice Guy Syndrome’. I just wanted to thank you for listing these reading materials on your site. You don’t make $ from this, but I can tell that you are truly interested in helping people resolve whatever sexual-relational problems they may have.”
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 | May 26, 2018
When my daughter was 7 years old, a boy kissed her hand on a dare. She confided to me, “It was the most enjoyable moment of my life.”
Now she is 17, and identifies as asexual. She doesn’t feel sexually attracted to other people, but she yearns for romance. She wants to hold hands, cuddle, and be intimate with someone special.
I’m thrilled to tell you she went on her first date the other night! They held hands!
I asked how their date went, and she gushed to me, “It was AMAZING. Not only were the events we attended awesome, but he was super sweet. He put his arm around me during the movie, and we held hands twice and he is so very kind all the time. God, I adore him, he made it so amazing.”
He’s like a young George RR Martin, they’re so cute and nerdy together.
I’m SO happy with this new development. She tends to brim over with teenage angst and melancholy, so it’s wonderful picking her up from school and she’s smiling so hard, her face hurts. The rush of happy hormones and feeling connected to someone special to her is better than any pill she could take!
I asked if he is her boyfriend, and she said she didn’t know, but she would ask him. She has ups and downs, and frets over being too direct with him.
I reminded her that she is probably advanced in the realm of communication, and needs to be patient with others and teach them how to be open and honest. I also let her know that the wonder is part of the fun of the early stages of a relationship – infatuation is a trip, and you should let it last as long as you can! After that, you get into attachment, feeling the person is a safe haven, then anxious when they are not around, then finally, secure (if the relationship is healthy.)
That’s where I’ve been with my partner Matthew for the past six years or so. We can’t go back to the infatuated stage with each other, but since we are polyamorous, we can feel secure while flirting with other people and enjoying novel experiences.
Anyway, my daughter shared her list of curated date ideas with me and gave me permission to share them with you. I think they’re so cute! She made most of them up, and collected some from the internet. I want to do a lot of them, how about you?
By Kendra Holliday | May 23, 2018
You have bad breath.
I’ll prove it to you:
1. Grab some floss. If you don’t have easy access to any, you have bad breath FOR SURE.
2. Floss a few of your teeth.
3. Sniff the floss. This is what your breath smells like.
Any food that is caught between your teeth and left there simply rots, right in your face. That’s why it’s important to floss daily – you don’t want a graveyard in your mouth.
The reason why I’m posting about this topic is because I run a sex worker group, and one of the most common complaints I hear from the women (besides clients being stingy) are johns with bad breath. It’s really hard to give the Girlfriend Experience when your partner smells like he ate a shit sandwich.
Conversely, I was at a Whore Happy Hour and one of the men complimented me on my teeth, saying the women he knew were sweet, but many had meth mouth and smoked. So I guess my nice grill is a good selling point, if you will.
SO, if you want others to enjoy kissing you, here are some easy tips on keeping your breath fresh n’ clean:
1. Brush your teeth twice a day. This is also good for your gums.
2. Floss daily. As they say, you only have to floss the teeth you want to keep! Glide is a good brand if you have crowded teeth and normal floss shreds.
3. Go to the dentist for routine cleaning twice a year. I don’t have dental insurance, but I still make this happen. A cleaning costs me about $150. Consider it skull maintenance.
4. Avoid coffee or smoking, but if you do indulge, rinse with water or brush your teeth afterward.
5. HYDRATE. Drink lots of water.
6. Eat more fruits and veggies, less meat. High protein diets are the worst for creating bad bacteria fumes as it decomposes.
7. Chew on parsley and mint! Eat your garnish at dinner, grow mint in your backyard and rejoice in the natural freshening powers of chlorophyll! Just watch out afterward for green stuff stuck in your teeth!
8. Listerine may actually do more harm than good because it contains alcohol and dries the mouth, which the bacteria tend to like. I use SmartMouth, it’s great! It shorts out the bacteria’s ability to breakdown and produce sulphides in your mouth.
9. Keep the mouth moist (god I hate that word) with sugar-free gum or mints. I always chew a piece of gum ten minutes before a date.
10. Tongue scraping is good. You can buy a scraper, but I just use a spoon every couple days or so. It’s crazy what can accumulate on the back of your tongue, it gets all thick and white, eww!
You can read more about halitosis here.
Do you have any fresh breath tips or bad breath horror stories to share? If you had bad breath, would you want someone to tell you?