Cucumber Yoni Cleanse

By Kendra Holliday | August 31, 2014

DIY cucumber dildo!

DIY cucumber dildo!

First, the grapefruit. Now, the cucumber…

What do you think a vagina smells and tastes like? Bittersweet? Sour? Pungent? Musky? Earthy? Oysters?

Mine smells and tastes different all the time. I’ve heard a vagina compared to a tidal pool, which sounds about right. It’s a woman’s own little eco-system and pleasure cove.

I posted about how to keep your vagina tasty and date-ready here.

I learned about cucumber yoni cleanse on this secret sacred yoni egg goddess group I belong to on fb.

Here is a page about it. An excerpt from the Eco-Goddess Temple:

“The New Whole Foods Encyclopedia, by Rebecca Wood, confirms that cucumbers are considered nurturing to the bladder, spleen, large intestines and lungs. It is a cold food that treats hot conditions and helps resolve toxins. A cucumber contains more than 90 percent water. Cucumbers are a food that tends to restore normal health because of its ability to cleanse and purify the blood and gradually alter the excretory process to restore normal body functions. Cucumbers contain a digestive enzyme, erepsin, that breaks down protein, cleanses the intestines and helps expel intestinal parasites.”

The other night I tried it, and it was better than I imagined!

I thought it would be goofy and awkward, but it turned into a sexy little loving date with myself.


A Pain in the Ass

By Kendra Holliday | August 28, 2014

Give your ass some TLC!

Give your ass some TLC!

The other day, I posted the following on fb and twitter:

You know that move in porn where the guy grabs a woman by her ass cheeks, and spreads them apart as wide as he can? Yeah, don’t do that.

I had someone do that to me recently, and it gave me a slight tear and hurt!

But then, I got mixed comments from it – turns out some women LOVE that move, and some women HATE it. Just goes to show you, communicating with your lover is key!

In addition, the post prompted a woman to send me the following unusual message:

“Dear Kendra,

Almost every time my husband and I have sex, I end up with the dreaded, painful, “butt crack split” I don’t know how else to describe it. It would normally happen if a guy ripped your ass cheeks apart during doggie, but I get it all the time!! With no butt cheek pulling!! HELP! It is painfully inconvenient! I put A&D on it, bag balm, anything I can think of, but it still happens. I love sex and can’t get enough of my husband, but this is getting ridiculous!! It hurts!! thank you in advance for any tips you can lend me! Is this common?”

I have to admit, I had never heard of anything like this before, but I’ll bet it’s common enough, and people are just too embarrassed to mention it!

I replied to her:

How long has this been going on? What positions do you try? Where do you have sex? Bedding? Do you have sensitive skin in other places? Is it the lube you’re using? How often do you have sex? Have you had past perineum trauma from childbirth or anything? Do you get hemorrhoids? There has to be some solution to stop this from happening.


What’s With Picky Orgasms?

By Kendra Holliday | August 27, 2014

Dear Kendra,

I’m 18, in college, and Female-to-Male transgendered. I have had three male sexual partners in the last eight months or so. Of the three, TWO have claimed that a handjob or blowjob WILL NOT DO, and absolutely NOTHING but penetration will get them off, and in the case of one of the guys, even that wasn’t enough, and he had to turn to his own hand.

However, on your site and elsewhere, I see tales of guys that can get off with ease using various methods beyond penetration.

So what gives? These guys are 20 and 21, respectively, shouldn’t they be rarin’ to go? What on earth is going on that penetration is the only thing that seems to get them off?

My reply:

It’s unusual that you ran into two men in a row who require penetration to get off. I think it’s a fluke. They probably both used penetration in their early masturbation routine and have become dependent on that way.

I’ve been with a couple guys recently who needed to take over and finish with their own hand. It didn’t bother me, as one was new and the other often finishes that way, but can just as easily get off other ways.

I think everyone should experiment solo and with partners to expand their menu if possible, but hey, at least they know what works! I have a few girlfriends who can ONLY get off via clit stimulation with a vibrator. Some of their partners are bothered by that, but they aren’t, and that’s what matters. They know their body and what they like.

What about you all – can you only get off one way? Can you only get off solo but not with a partner? Does it bother you if your partner can only get off one way? Do you think it’s important to train yourself to get off in many different ways? Have you ever been surprised at an atypical orgasm? Do you find a difference in how you respond when engaging in casual sex vs long-term partner sex?

What’s your favorite way to get off? Mine is lying back, relaxing, and having my pussy worshiped with an experienced tongue.

PS: Have you seen those videos where a woman gets off using a door? Never would’ve thought of that!

I blow, therefore I am Goddess.

Oral sex is the #1 way to send your man into ecstasy. It feels incredible and few men can resist the opportunity for their cock to be worshipped and loved. Best of all, his deep gratitude is bound to pay off considerably later on when he eagerly returns the favor. Here is a breakdown on how to give a great blowjob, TBK style.

Great conversation topic

Before you put your mouth to good use, ask him what he likes so you know what to lay on thick and what to avoid. Does he like his balls licked? Teeth? Lots of suction? Strong head stimulation? Slow or fast? You can have this conversation over dinner or while sitting on the couch watching TV, but be prepared to stop what you are doing so you can practice. OR employ tech foreplay and do it over IM or text during the day so you can prime his pump for when you see each other that evening.

Tease him

Take the tease trail. For example, start by kissing your most fortunate test subject, then slowly head south, kissing and licking his nipples, chest, belly, thighs, balls, shaft, then finally make your way to his cock head.

Once you’re there, open your damn mouth. I keep hearing from both men and women about these women with small mouths who can’t get the job done. Despite what you might think, my mouth isn’t that big, and I can stuff something substantial in it. Though I can’t fit a soda can in it like I saw one woman do. That’s impressive. If you have TMJ/jaw issues, do the best you can and supplement with edible lube/hands.


Vanilla Night

By Kendra Holliday | August 17, 2014

Pretty please?

Pretty please?

You know how some people have a kinky night, where they bring out the fuzzy handcuffs and the whip cream in order to spice things up?

Well, every once in awhile – like, every three or four months – Matthew and I have a Vanilla Night.

We’re so used to fucking around with our kinky friends and enjoying extraordinary encounters, that we enjoy the challenge of switching gears and trying our damndest to be normal.

We even give ourselves normal names on these nights. Instead of Matthew and Kendra, we’re “Randall and Michelle.”

We’re monogamous, married eleven years, and he is pussy whipped and I’m a bitch.

Instead of me washing the dishes while he steps outside for a drink and a smoke, he cooks dinner AND does the dishes. I don’t say please or thank you.

Instead of talking about a porn clip or the upcoming pirate orgy, we discuss what we should get our friends Roger and Stacie for their big Chicago wedding, and if we should attend the baseball game while we’re in town. I tell him I’d rather go shopping and that he better not have more than two beers because he has to watch his carbs.


Local Couple Tries Grapefruit Trick!

By Kendra Holliday | August 12, 2014

Have you heard of the grapefruit trick?

I read this review from a woman who tried it and was intrigued. I love grapefruit, and my man loves blowjobs!

I asked him if he wanted to try it and he flat out said NO.

“Why not??” I exclaimed.

“I have a Tenga and a Fleshlight. Plus, I don’t like mixing food and sex.”

Fair enough. So much for getting my daily dose of Vitamin C (as in Cum!)

My friends tried it, though! Here is their experience:

Grapefruit trick!

Grapefruit trick!

“I watched with anticipation as she cut the grapefruit. I’ve had no experience with Fleshlights or any other sort of masturbatory vaginas, so I thought,  ‘This could be interesting!’

I lay back on the floor of my kitchen, towel beneath me as she stripped down to arouse me (and keep the citrus off her dress). She began by teasing me with her mouth, my penis coming to attention the flood the pleasure rushing to my head. My eyes were closed because the instructions called for the recipient to be blindfolded because the procedure was supposed to be a surprise.

Suddenly in the midst of the warmup came the main attraction. She slipped the fleshy citrus donut over my cock and squeezed it while continuing her ministrations. There were moments where I felt as though I were inside a Vagina Dentata, a soft, pocket purse of flesh with a hungry mouth at the other end.

And then there were other moments I was a dude with a piece of fruit on his dick.

I was thinking about Led Zeppelin’s “Lemon Song“: “Squeeze my lemon ’til the juice runs down my leg’, as it was a messy affair.

She sucked and licked while squeezing the grapefruit around me. “Slurp! Slush! Squish!”  My eyes rolled back in my head. Back and forth my mind went, between Toothed Pussy and Fruit Cock, the pleasure rising from the base of my balls, rising then holding, not going anywhere.

I had peaked and the  awareness of the cool sticky juice running my leg took over, and I asked her to stop. I didn’t want her to waste her time. I wasn’t going to cum this way. My lust had only taken me so far, what I really wanted was to be buried inside her listening to her moans of pleasure, something I couldn’t do covered in citric acid.

For hygienic purposes , I jumped in the shower and rinsed off, then met her in the bedroom where the games began in earnest! Orgasms for everyone!

Overall, I would have say I had more fun being smeared with Nutella. It’s messy, but the attention I get is greater than grapefruit. There’s nothing a grapefruit can compare to when someone is excellently working the shaft during a first rate blow job.

I would give it a 4 out of 10 as orgasmic tool. Worth trying, but sort of ‘Meh’ in the end.”

Tools and Tips for Women Seeking Orgasms

By Kendra Holliday | August 11, 2014

Are you a woman who hasn’t had an orgasm in a few years? How about ever?

Want to expand your orgasmic repertoire?

Here you go. Read this post by Joan Price. Then, watch this.

Betty Dodson has been a pioneer of female orgasm for over 40 years. She’s 85 now, and while she tends to rub some people the wrong way, I have to admit she is on to something!

She’s known for her book Sex for One, as well as being a champion for the vulva and clitoris.

A few years ago, she had an advice column in Bust magazine, and I was dismayed at some of her replies. She seemed very dismissive of women masturbating outside the box and seemed to be on her way out, introducing her sidekick, Carlin Ross.

But then earlier this year, she caught my attention by pissing off a bunch of politically correct people at CatalystCon East. She joked about grabbing someone’s ass and fucking a dog or something, and people were outraged.

So that got me interested in her again, and then I heard her piece on the RISK! podcast and that was great. And then I read Jenny Block’s account of a group masturbation workshop hosted by Betty. Mark my words – we’re totally going to do something like that in St. Louis in the near future!

So I’m back to being a Betty fan (just like how Dan Savage won me over again by being bold and owning up to past foibles, while still sticking to his guns.)

My friend who is in her 40’s and newly dating just discovered the Hitachi Magic Wand. She CROWED about how she doesn’t NEED a man now! The wand helps her take the physical edge off when her hormones are raging, and allows her to take her time finding her next partner, one who is well-suited for her.

So, yeah. Click around this blog post and discover some new tools and tips. I love learning something sexy and new everyday!

And spreading the good word!

Getting to Know Each Other

By Kendra Holliday | August 10, 2014



Matthew sends me a challenge via email:

“You are to seduce me soon… Entice me like you would someone you are fucking for the first time…Again. Take Control. Show me you want it and you won’t stop until you get it.”

It’s a challenge all right! It’s difficult to make the first move on someone who is so dominant in your life. Someone you know so well in one way, but not others. Someone you’ve known for years and take the comfort and familiarity for granted.

I’m up for it.

“I’m ‘that guy’ from okcupid,” he tells me. OH I get it. We’re pretending like it’s our first date.

The day of our date, I get a message on okcupid from him telling me that he’s looking forward to our date, and that he’ll pick me up at 6:30. I message him back in kind.

We have dinner at a sushi restaurant and have a fucking blast. The waitress Ling loves us. Sake and beer flows, we eat Hot Mama rolls, and get to know each other.

Throughout the evening, we ask each other questions as if we don’t already know the answers, and we actually learn new things. For all of you in long term relationships, you should totally try this!


Male Sex Workers for Women

By Kendra Holliday | August 10, 2014

A perverted gentleman.

A perfect gentleman.

The other day I received this message:


I was wondering if you could offer advise on how to get started or if its even plausible to do what you do but as a male instead of a female?”

First of all, I offer consultations for this type of thing. You can check out my website for more info.

Second, the answer is yes, it’s possible to be a male sex worker for women. You can apply to be a Cowboy 4 Angels, a service that offers straight male escorts for women.

From the website: “Cowboys need to be very attractive, dedicated to a top level of fitness, presentable, well-groomed, stylish, charming and desirable. Cowboys need to be confident but not arrogant, yet savvy. All need to be emotionally mature, stable and possess a genuine respect for women.”

Read this interesting article inspired by the television show “Hung” on male sex workers representing all kinds of niche markets – black men serving as “bulls” for parties, men hired for cuckolding fantasies, strippers and more. If you’re going to be a sex worker, figure out what your specialty is – working with people with disabilities? G-spot orgasms? Tantra? Massage?

Here’s an article featuring a man in Australia, where prostitution is legal. He seems to have a handle on what women want – to be pampered, worshiped, made to feel special, and oral. Lots of oral sex.

If you want to be a successful male sex worker, in addition to looks, brains, and personality, you need to be compassionate, confident, sexy, mature, intuitive, a great listener, and able to read body language. The focus should be on the woman – not your penis. You also need to be able to see the beauty in your clients, no matter how old, fat, or annoying she is. You need to be good with condoms.

What other qualities would be important for a male sex worker who is seeking female clientele?


Mating in Captivity

By Kendra Holliday | August 9, 2014

Mating in Captivity, by Esther Perel

Mating in Captivity, by Esther Perel

Mating in Captivity is a great resource for anyone who is unhappy in their traditional, monogamous marriage.

The author and therapist Esther Perel notes that her husband is also a therapist, but he works with people who are refugees and have been tortured and have PTSD. She says her husband deals with pain, and she deals with pleasure. I say she’s also dealing with pain, just on a different level. And yes, pain and pleasure are intimately connected. Both make us feel ALIVE.

How do we get more pleasure in our lives, and less pain? Ultimately, we are in control of our lives, and can make choices that will lead us to a happier, healthier place. These choices can be difficult, and take a lot of work. They take courage and strength.

I was counseling a couple recently who have been married for over 40 years. Their relationship is spectacularly dysfunctional. I gave them real advice on how to change things (as opposed to a pep talk), and it fell on deaf, stubborn ears. Neither of them want to make the first move. They don’t want to leave their comfort zone, even though it has pot holes and bear traps. So frustrating.

Esther very patiently takes an entire book to break down what we all want – we want EVERYTHING. We want adventure, security, passion, love, independence, to be appreciated and desired, comfort, happiness… and guess what?

It’s really difficult balancing all of those things, especially if you are counting on one person to fulfill all of your physical and emotional needs. Most people cannot have everything. And if it is your goal to have everything, it’s really challenging finding the right balance.

For instance, Esther gave some couples some pretty hardcore advice. Going beyond the usual tips of scheduling dates on a regular basis and cute relationship exercises, she suggested one couple get divorced, but still live together. She advised another couple to live in separate homes.

You can wallow in the known and complain about it and let resentment build, or you can take a risk and make real changes. Sometimes happiness is handed to us, but more often than not, it takes hard work and courage to obtain.


Henna on Heavenly Bodies

By Kendra Holliday | August 5, 2014

I’m FINALLY posting a follow up to this henna post a while back. My sister inspired me! (Scroll down to see what I mean!)

Here is some amazing henna artwork by Jeanjoel from a couple years ago. I love having milky pale skin and a blank canvas for artists to work on…

Henna drying

Henna drying

It’s so relaxing to lie there and be still, feeling the paintbrush tickle.



Don’t you love my little willow tree pubic hair in this shot?


Cuffed and Stuffed

By Kendra Holliday | August 3, 2014

I had another wild-n-crazy roleplay date with my friends Capn Marrrk and Bianca. They always do such a good job of creating an elaborate scenario and are so clever with costumes and props! For example, there was the time we pretended to be two sisters disciplined by a military instructor…

This time, I was playing the prisoner, Bianca was playing “Mama” the police officer, and Capn was the mean Prison Warden.

They kicked it off with a letter that announced I was up for a parole hearing:

Parole hearing notice

Parole hearing notice

I showed up with my orange prison costume on hand so I could change when I got there. Truth be told, I had a terrible day and was stressed and overwhelmed. I didn’t feel like an elaborate roleplay scene. I felt like vegging on the couch and whining and being coddled.

But when I got there, I discovered they were already dressed up and in character! She was wearing a tight, sexy blue police uniform, and he was wearing a brown suit and police sunglasses. Both had their arms crossed and looked STERN. They meant business!

Right away they addressed me as Prisoner #23049 and escorted me upstairs to change. OK, here we go!

As soon as I was in my jumpsuit, they cuffed me and led me to the chair for interrogation.



The Warden asked me all kinds of probing questions and grilled me. He made me state why I should be allowed early release, my plans on the outside, etc.

He informed me that if I wanted to get out of prison, I had to do whatever they say, including being their sex slave! They both were very serious and weren’t going to let me off easy.


30 Shades of Great Erotica

By Kendra Holliday | August 3, 2014

Everyone is bitching about how terrible 50 Shades of Grey is. I’m no exception.

Yes, it sucks.

So where can you find GOOD erotica – the kind that will jump start a million libidos and celebrate kinky creativity?

Writing is not easy, but based on all the incredibly shitty erotica out there, it must be especially hard to craft this genre. You have to use the right words and flow to elicit feelings of arousal, rather than cringing. It’s a delicate balance. Plus, it can be pretty subjective. Some people hate the word “cunt,” while others can’t stand the term “nether lips.”

I asked friends and readers for their recommendations, and came up with this extensive list of 30 Shades of Great! Thank you to everyone who contributed!

Are you ready to check one of these out?

Are you ready to check one of these out?

1. Sleeping Beauty Trilogy – this one was mentioned the most. You should probably check it out.

2.Literotica – Hit and miss, but LOTS to explore. My favorite category is Incest/Taboo.

3. Lady Chatterly’s Lover

4. Anais Nin – I remember being so shocked and turned on reading the scene where a group of men pin down a woman and let a big, shaggy dog lick her pussy. I also got really disturbed and turned on reading about the man who found a freshly drowned body and had his way with it.

5. The Story of O - female submission galore

6. Rachel Kramer Bussel – The Big Book of Orgasms

7. Exit to Eden – more Anne Rice BDSM

8. Genesis Deflowered - the Bible is already salacious enough, but this author fleshes out some scenes…

9. My Secret Garden – published the year I was born! These fantasies are timeless…

10. Forbidden Flowers – encore to Secret Garden

11. Kushiel’s Legacy series by Jacqueline Carey – I’ve read this, it’s pretty good. Hell, you know it’s good when you remember certain scenes and incorporate them into your own fantasies – the one that stands out to me is when the slave girl is in the great hall and is presented to a Lord as a gift, and his Lady watches him take the slave girl on the table…

12. Whip Smart – memoir of a college student working as a dominatrix


Fuckation Recap!

By Kendra Holliday | August 2, 2014

This chest makes an excellent tuffet

This chest makes an excellent tuffet

Like true responsible hedonists, we planned our fuckation perfectly – his kids were out of town, my kid was with her dad, we requested time off work and didn’t schedule anything. We took care of our shit so we could have as much fun as we wanted, guilt-free and carefree!

Rare is the day where you can wake up and lounge, knowing you have ZERO obligations for the next 24 hours. You can do whatever you want, WHOever you want, and today I wanted to spend all day in bed with my man.

In preparation for our dream come true, we had a rollicking night out on the town, bar and museum hopping.



History Museum

History Museum

Liberty for All!

Liberty for All!


Powerful Touch

By Kendra Holliday | July 20, 2014

I love to explore.

I love to explore.

So this sex surrogate work I do is hugely important, and I really and truly love it.

When I am engaged with someone and riding the waves of passion, I feel it in my core – in my heart and in my cunt – even if I am only giving the pleasure. I feed off the energy, it’s circular and ALIVE. It’s simultaneously relaxing and energizing.

I am honored to share intimacy with good people. I love mentoring and teaching others about sexuality and themselves.

I spend time with SO many interesting folks. They’re so diverse, but they are all keenly interested in a common goal: healthy human connection.

From the Middle Eastern Muslim man whose arranged marriage failed, to the man with a serious muscle disease who was told he would die by the age of 20, to the Catholic man who puked the first time he had sex, to the 44-year-old man who hasn’t had sex yet, to the man who was molested by a family member and can’t orgasm when other people are present, to the Asperger’s man who is clueless about courtship and body language…the list goes on and on.

After a recent sweet cock worship session, a client reported back to me:

“I felt giddy and somewhat euphoric and more energetic than usual the rest of the day — almost to the point of downplaying it so that others wouldn’t notice anything different about me today.  And it’s more than I can justify on the basis of a conscious memory of the fun I had.  It’s more like I had to stop and think about why I was feeling this way.  It’s almost like I’m feeling the effect of pheromones, or a spike in oxytocin from all the touching, or a spike in testosterone resulting from the whole thing — maybe arousal combined with touching — it’s like I’ve been mildly drugged, definitely enough to be noticeable.”

Look at all the articles and studies out there about how healing human touch is, not just for premature babies, but for humans of all ages.

We need to touch each other more often.

My friend has a cuddle club that meets once a week. They all get together and talk about science or watch a television show in a cuddly, consensual fashion.

There are many types of touch – healing, nurturing, soothing, caring, sensual, erotic, intense – do you know the difference?

The other day I was touching an inexperienced man with erotic intent – trailing my fingers gently all over his body, tuned into his male energy, slowly heading toward his erogenous zones. He was used to massage and other therapies, but this felt different to him. He said my caresses made him tingle all over and flush with pleasure. So nice that the feeling can linger, and carry over into other parts of our lives.

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Sure, St Louis has high STI ratings, but let's keep a clear head on this topic.


Seriously?? C'mon, people!


Like Kinder eggs and cigars, not heroin or poison dart frogs.


Not at his request, but because I have a slight thrill for smuggling illegal things that are completely silly to be illegal.