By Kendra Holliday | May 27, 2020
Category Archives: Passion & Intimacy
I know this is going to sound silly coming from a sex worker, but I’ve finally figured out why I find eager, impatient men to be so off-putting.
I get so many men contacting me who want to go from zero to anal in less than an hour.
My whole mission as a sex surrogate is to teach people how to build intimacy and be a good partner, and guess what?
Building intimacy takes time.
I have an extremely reasonable process in place, but all too often I find myself being pushed along like meat on a conveyer belt, ready to be gobbled up, instead of savored.
A man will contact me, and he’ll get super excited when he finds out that I offer all kinds of sexual exploration experiences. He’ll want to do them ALL RIGHT AWAY.
But I’ve learned that I need time to build a relationship with someone, in order to feel comfortable and for things to be authentic. Otherwise, I feel like I’m forced into a performance, and it leaves me feeling yucky afterward, and a relationship that was initiated with such promise and potential becomes tainted, and I have to cut it off in order to protect myself.
Here are my biggest turns offs:
Here’s what turns me ON:
An attitude of gratitude
A generous spirit
I find that the most rewarding encounters I have are with clients who have allowed me to set the pace for building intimacy. I have amazing relationships with clients I’ve been seeing for years. We’ve made so many fantasies come true together!
Here is how to spoil things quickly:
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Disregard feelings and safety
Here is how to create a lasting relationship with me:
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment
By Matthew | May 4, 2020
I love to flirt, and women seem to enjoy flirting back. The casual fun flirting is a blast, and I enjoy it. But I never know if they want to move from fun flirting to something more serious.
I’ve tried a few times to make the change to serious flirting, and found out I was wrong, and screwed up friendships. So for the past few years, I just automatically default to “it’s just for fun” and don’t even try to “make a move.”
So I guess what I’m asking is – is there any good indication that a woman is interested in moving the flirting from “just for fun” to something with more intent? What Are Best Practices for Men Flirting With Women?
I’m going to turn this one over to Matthew! Now, this is a man who is not into tricking or manipulating other people.
He takes “master pickup artists” and picks them up and tosses them in the dumpster.
He practices open and honest communication.
He doesn’t have a GQ model body, but he has the confidence of Zeus.
He realizes that not every woman wants to be with him, and HE’S OK WITH THAT. He’s only interested in being with women who are genuinely into him. Somehow, he manages to play the situation so that he KNOWS the woman is desperate to get to his cock. At least, that’s how he played me. For months. The bastard! Sigh, I’m hooked.
Take it away, Matthew….
This is a great question and I am going to address it on a number of levels. Specifically to your question, first and foremost what comes to mind is an encounter I had with a woman some time ago.
By Kendra Holliday | March 3, 2020
I offer sex and relationship consulting, and I’m happy to say that I’ve been getting more women, LGBT folks, and couples these days. Historically, most of the people who have sought me out for my unique services have been men who crave female energy.
The Top 5 reasons why people contact me are, in this order:
1. He’s a married man in his 50’s or 60’s whose wife is not interested in sex (mismatched libido)
2. He/she/they have some sort of sexual issue they want to work through, such as inexperience, anxiety, or orgasm/penis problems (Erectile Dysfunction is a common complaint – it can get complex when you heap social conditioning and anxiety on top of the natural aging process.)
3. He/she/they are interested in branching out sexually, either because they are in transition, not getting laid, or curious about alternative lifestyle options (non-monogamy, BDSM, sex work, etc.)
4. He has a fetish and is ashamed/seeking an outlet
5. They want to meet me, and possibly rub me for good luck
My goal is to offer tools, connections, and non-traditional options so that the people seeking me out can reach their goal of becoming happier and healthier. My approach is unconventional, and I get referrals from licensed sex therapists. I’m pretty well connected and have a strong network. Sex is my specialty, which ties into work, family, personal – everything!
Here is a list of resources I most often recommend to my clients:
By Kendra Holliday | March 1, 2020
Years ago, I went to a swinger party with an ex. There were six women at the party, and we all had lots of fun. But, to my surprise, when we were driving home, my ex lamented, “I only got to be with four of the women there.”
That’s right – he was dissatisfied with only getting to stick his penis in four of the women’s vaginas that night. He was keeping score!
I’ve noticed other times where I’ve played with a man, and we’ve gotten naked, shared pleasure, had oral, but he left disappointed because he didn’t get to do ALL THE THINGS, i.e., stick his penis in my vagina and have intercourse.
I have clients who spend time with me, and instead of basking in female energy and pleasure, they get bummed if they don’t have an encounter that involves them having an 8 inch penis that remains hard for 45 minutes and drilling me bareback in four different positions.
In other words, they feel let down that they aren’t having sex like they see in mainstream porn.
Meanwhile, I’m having amazing, abundant sex with my partner of 11 years that is leaving us both extremely happy and fulfilled.
You want to know why?
Because we are having CREATIVE SEX. We aren’t having straight sex!
Straight sex is what you see in mainstream porn. It is male centered. It’s penis focused. It’s vigorous and aggressive. It’s filmed for camera angles, and based around the male orgasm. It’s objectifying. It’s GOAL ORIENTED, which can set the stage for unrealistic expectations and A LOT of anxiety. And anxiety is terrible for arousal!
The women in straight porn are often uncomfortable – from the fake eyelashes and bleached hair and garter belts and heels, to the pussy pounding and loud vocalization and money shot in the eye.
Creative sex, on the other hand, is more about pleasure, skinship, being in the moment. It is about savoring the experience.
Straight men crave intimacy and connection, but they seek it out in a rigid way that can set them up for disappointment and failure. Moreover, it can be off putting or dissatisfying to their partners.
Creative sex is more egalitarian, and allows for more pleasure and orgasms for all parties involved.
By Kendra Holliday | November 6, 2019
My friend Joan Price introduced me to Galen Fous MTP, the author of this book, and right away I could see why – he’s a Dominant father in his 60’s living on the west coast, and I am a submissive mother in my 40’s living in the Midwest, but we have SO much in common!
We’re both completely out and open about our kinky and creative sexualities. We both went through hell and almost lost everything when we came out with our stories (his outing was forced by his ex; mine was more my choice). We both persevered and are now fully integrated and have a career in the field of sexuality.
Galen’s book is called Decoding Your Kink: Guide to Explore Share and Enjoy Your Wildest Sexual Desires.
As I read his book, I was amazed at how much it mirrored my thoughts on sex and our unhealthy society.
We both subscribe to the King and Queen archetype, and to the beauty of rituals. Galen points out that rituals are tools that help us focus our attention. Natural and innate, rituals are all around us – seasons, rhythms, holidays…
By Kendra Holliday | October 23, 2019
THIS ARTICLE really inspired me. A therapist shared about how men try to be close with their partner through sex, and how being rejected, or even having to always initiate sex, can be so discouraging and disheartening.
Here’s the thing – someone up in the sky is playing a big joke on us, and they’re using our social construct and hormones as trickery!
Most men of all ages experience spontaneous desire – they wake up feeling horny and activated, and walk around all day seeing sexy things and feeling inspired. This is due to their higher testosterone level, and the fact that society paves the way for men to go after what they want.
Women, on the other hand, have responsive desire. They are trained to hold back, be demure, and once they are introduced to an erotic situation, then they start to feel aroused. Women also need to feel safe and comfortable in order to relax into full arousal.
Of course, these are gross generalizations and a very binary approach, but for the sake of concision, I’m not going to spend a lot of time qualifying language, but you get the gist.
Men are pretty much ready to rock much of the time, and women are more reticent. They need more stars to align for them to be open to sexy time.
So, what do we do about this? We make concerted efforts to shake things up!
First of all, we need to recognize that HORMONES ARE REAL. They influence our moods and health in ways we don’t realize.
Second, we need to change the social construct. It’s impossible to overhaul the entire system, but we as individuals can make a difference on a local level.
By Kendra Holliday | July 3, 2019
After a recent encounter, one of my former virgin clients shared this with me:
Porn has almost completely lost its luster for me. I find it vastly inferior to the memories of the experience I had with you in St. Louis, and those are just memories! All I have to do is think of you – of your smell, eating your pussy, kissing you, fucking you, feeling your weight against my body, intertwining my legs and arms with yours – and I am instantly aroused beyond anything porn can do for me. Frankly, now that I’ve had a taste of the real thing, it’s hard to see porn as anything other than a pale imitation of what sex is really like.
This man and I would love to have another session, but logistics are challenging – finances and distance – he had to drive hours to make it happen, which I think is very brave and commital – Cowboy Ethics! Ride for the Brand!
By the way, inexperienced men tend to be some of the best pussy eaters! It’s TRUE. ESPECIALLY when they read and research in preparation for our sacred encounter – two great articles to read before you enter my bedroom chamber is “How to Eat My Pussy” and “What I Like and Don’t Like.”
That’s not the only reason I love inexperienced men. They’re more respectful and grateful. You get to teach them how to be good lovers. I wish I could get to them when they’re younger, before they’re warped by porn and misinformation, but society can’t handle that.
One of my clients is quite unique – he has sickle cell anemia, which is a rare blood disease.
Here is the initial request I received from him:
My name is Robert and I am 38 years old. I saw an article about your blog in the RFT. I’ve been reading your blog off and on since then. I’m learning a lot from your advice and the advice of others on your links column. The experience has really been enlightening. I hope you can enlighten me some more.
I have sickle cell anemia. It’s a blood disease that misshapes the blood cells and make them pretty much incapable of carrying oxygen through the body. Their odd shape can get them stuck in the bloodstream; it causes chronic excruciating pain that needs medical attention. It can be deadly in some cases. Eventually, the body’s organs become negatively affected.
I suffered a stroke when I was 17, my senior year in high school. I was diagnosed with kidney failure in 2002 and started dialysis in 2003.
Throughout my teens, I was really sick, so I relied on my parents to take care of me. This made me decide to stay away from any kind of personal relationships. A couple of months after my stroke, I declared myself asexual; I figured no woman would want to be in a relationship with someone who wasn’t totally healthy.
After the kidney failure diagnosis, I started dialysis in 2003. In the five years of dialysis, I had only one bout of severe pain. I owe it all to my changed lifestyle of eating better and exercising as much as I could tolerate.
The positives only got better from there. In the summer of 2007. I got on the transplant list. In 2008, I got a new kidney. I now have a clean bill of health.
Last year, I declared to myself that I would now seek out a relationship, and if the friendship turned into something more, I would see where it goes. I am healthy and confident enough that a love life would be sustainable for me.
My problem is that I’m still anemic. That’s never going away. I get fatigued easily. At this stage of my life, I’m wondering about sex. I don’t know how long I would last and what I could do.
I love my doctors, but they’re not sex therapists, so they can’t really help with this worry. If I’m in a relationship that involves intercourse, I need to ease myself into the act and last for as long as it takes for both of us to be satisfied. Can you help?
Waiting for your kind words with baited breath,
I was intrigued. Right away I did some research on sickle cell anemia and sex and found there isn’t much out there. You’re supposed to drink a lot of water to hydrate yourself, and men tend to have prolonged erections. Looks like we’d have to learn together!
By Kendra Holliday | May 24, 2019
Ed Note: This is a guest post by Jem.
I was married for twelve years. For almost all the time we were together, everything was good. Almost.
About eight years after we got married, my husband forced himself on me. We were getting into bed, we were both sober, I had no idea what he was going to do. He held me face down. We’d played at this sort of thing before.
This wasn’t playing.
I shouted at him to stop. He’d never done anything like that before. Not even close.
I got dressed, left and went straight over to see a friend. He was a lawyer. It was about eleven at night, he could see I’d been crying. I told him what had happened, and at first he thought I wanted him to report a rape. I just wanted a place to stay and a friend to talk to.
My husband didn’t rape me. He betrayed my trust, didn’t respect my wishes, was clearly on some sort of power trip. He never did anything like it before or since. He was deeply ashamed by what he did, and had a harder time forgiving himself than I did.
My friend and I talked for hours. We ended up talking about sex and the law. At some point he said that adultery was when a man and a woman had consensual, penetrative sex. Nothing else counts. We had fun coming up with things that weren’t adultery: blowjobs, gay sex, buggering a sheep, being tied up and having five guys come over you … not adultery. Grounds for divorce, but not adultery.
I stayed the night in his spare room. He gave me a T-shirt to sleep in. It was about three in the morning by this point. I lay in bed, and decided about a dozen times that I would go next door. I didn’t.
We met up at a coffee shop about a week later because he wanted to know how I was. We didn’t buy coffee, we decided to go back to my place and drink coffee there. We sat on my sofa, talked, I told him how grateful I was for his support. How everything was better with my husband, now. It was, we’d talked and he was guilty and sorry. At some point, my friend put his hand on my leg. He had to get back to work, he said.
I’ve just got no idea who made the first move. We kissed, we stopped kissing and looked at each other and I said ‘oh no’. We joked about this later. We both knew at the coffee shop that this would happen. We didn’t plan it, but put it this way: I was wearing matching underwear. Then we were kissing again and I think I was the one who lifted up my top, but that might have been him. He pulled up my bra and sucked on my nipple so hard it probably should have hurt. It didn’t. Then he really, really had to get back to work.
The first time we didn’t commit adultery was three days later.
By Kendra Holliday | March 23, 2019
My wife and I recently decided to open our marriage. Unfortunately, I’ve run into a problem: women don’t seem to want to get involved with a man who is in an open marriage.
So far the three women who I’ve approached, although they admit being attracted to me and interested in the idea, have all given me some variation on the same objection: they’re worried about hurting my wife or causing harm to our relationship. These women know both my wife and me, and they aren’t willing to even acknowledge the possibility that talking to my wife could resolve their concerns.
I can’t help but find this fairly insulting. These women seem to be substituting their own judgment for mine and my wife’s, and telling us that, as much as we might think we’re ready for an open relationship, we will inevitably fall victim to jealousy and bitterness.
Now, I can understand that some women may not want to take any risk of being responsible for that, no matter what the people in the relationship might say, and maybe there’s nothing I can do to change those women’s minds.
But how can I best explain that they don’t have to worry about causing harm to our relationship—and that even if that happened, it wouldn’t be their fault—and how can I maximize the chances that they’ll overcome their feelings of unease and be willing to get involved?
I asked a couple successful poly guy friends of mine for their 2 cents, and their combined answers added up to at least 2 bucks! Here is J’s take:
“Why not approach women who already identify as poly themselves and have other already established relationships? You can join a poly group in your town and mingle with like-minded people.
Of course I realize that’s a tough pill to swallow when you’ve already got what seems like three perfectly willing takers–if only it weren’t for their warped view of his wife, the mutual understandings they may have in their relationship …or what, on principle the sanctity of his marriage to her? Yeah, honestly I’d feel somewhat insulted by these assumptions of overreaching responsibility and risk too.
By Kendra Holliday | March 17, 2019
A friend of mine is not a fan of hardcore porn. I asked him to tell me what kind of porn he enjoyed, and he wrote me this letter. Enjoy!
I realized, after a lifetime of looking at porn, that I don’t like almost all of it. It’s grotty, unpleasant, populated by people I don’t want to talk to, let alone fuck, and the more extreme the porn makers become, to stand out from their competitors, the more they turn me off, both because of the scenario presented (I don’t want to rage-fuck someone in a basement) and because of the tragedies inherent in the production.
Young women with too much makeup and plastic surgery don’t turn me on, they make me sad and wonder about where their parents are.
But I recently came across some porn that seems designed specifically to appeal to people like me — which I would define as oversexed, heterosexual white males. It’s made by X-Art, and is the Platonic Ideal of Vanilla Porn. Looking at it (which I’ve done a lot) made me think a lot about the kind of porn-fantasy it presents, and why its so appealing.
A typical X-Art vid features a young woman, with a body unaugmented by wear, surgery or (too much) makeup. The setting is a high end apartment (many of the vids seem to be shot in the same LA loft) that might be the home of a protagonist in a Hollywood film. The man is attractive, but not the focus at all… there are a number of videos in which you rarely even see the man’s head. Everybody is young and perfect; hairless, both metaphorically and literally.
The music is different than typical porn. Many vids start with a cool, indie sounding pop song, the kind of thing attractive people might listen to in their excellent apartments, and then they fade out in favor of “natural” sounds. No wocka-wocka bass line to constantly say PORN. (more…)
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 23, 2018
Last Saturday was the night of the Super Moon, the one time of year when the full moon would be closest to Earth.
We had spent the day hopping from friend to party to friend to parade, drinking and being merry – it was a full day. It was a LOT of day!
It was a great day.
After the craziness of a busy festival in Soulard, we chilled at our friend Shine’s house. It was a stark contrast to the packed street party that was jammed with people, bright lights, and HEAT – Shine’s house was cool, dim, and surrounded by resting plants. It was just the four of us.
She mentioned that the night before, she had been to Monks Mound to celebrate the moon. Monks Mound is in Cahokia Mounds, across the river in Collinsville, IL. Monks Mound is the largest human-made mound in the country. She spoke of how powerful it was to be so close to the moon, fog in the valleys, the energy of all the people who had once been there…. 20,000 people lived there, making it larger than London in 1250 AD.
After a raucous family dinner, we made our way over to Illinois. The surrounding area was a little eerie – rundown homes, race track, landfill, liquor stores, ghost towns – a lot of buried dreams.
It was dark. We parked near the mound. Technically the place was closed, but it felt like a free country and we meant no harm, so we ventured out into the moon-drenched surrounding meadowscape.
I was barefoot, wearing a soft, flowing moon dress. We held hands and walked toward the looming mound. No one was around.
Up the first level we went, then the second. Finally, we were at the top. (more…)
By Kendra Holliday | September 2, 2018
I adore cute little old men, so when one contacted me online asking for a date, I happily agreed.
We met in the dim, red, richly appointed lobby of a luxury hotel. We were both a little nervous. I had no idea what he looked like.
I was relieved when one of the anonymous men standing around broke away from the faceless crowd and warmly approached me. I got instant good vibes from him.
He resembled an Orville. He was small and neatly groomed, very dapper in his three piece suit, right down to his silver tie pin and cuff links. With my elegant black dress and pearl necklace, we made a smart looking couple.
He ordered me a glass of wine, which I sipped politely as we got to know each other on a velvet sofa in a cozy corner.
He was from out of town. He summered in Cape Cod and wintered in Florida, having a home in both places, as well as one in Virginia.
He had a wife of 45 years who was a good woman, but never touched him, not even holding hands while they watched a movie, lest he get the notion that this basic physical contact would lead to something more. She had no interest in intimacy or sex – she found it distasteful and unnecessary – and expected him to follow suit.
Trouble was, he was a human being. Humans NEED physical contact. Which is why he sought me out.
A lot of people think whores are homewreckers, when actually the opposite is true. They do a great service keeping marriages together.
Many straight men NEED to sip from the cup of feminine energy just as they need to breathe and eat. If their wife cuts them off, they will look for intimacy elsewhere, or suffer miserably.
By Kendra Holliday | September 1, 2018
Would you like to know your asshole better? How about someone you love’s asshole? Do you wish you could stick things in it in a way that feels intensely amazing, but are not sure how?
Anal is one of the sex acts I get asked about the most, mainly from women who fear it, and men who want to explore it. To that, anal expert Tristan Taormino chirps, “What’s up, chickenbutt?” OK, not really. Instead, she makes videos.
For the newbie set, I recommend Tristan’s initial video on the subject, Expert Guide to Anal Sex.
For those who want to take it to the next level, there is the newly released Expert Guide to Advanced Anal Sex.
Tristan Taormino’s Expert Guide to Advanced Anal Sex stars Nina Hartley, Bobbi Starr, Kylie Ireland, Adrianna Nicole, Mr. Marcus, James Deen, Danny Wylde, Christian, with special appearance by Sinnamon Love and Tyler Knight.
Note: Bobbi Starr was so charming and special, I had to go look her up. She reminded me of a friend of mine, proof that she nailed the “girl next door” schtick. Bobbi talks about how she only does anal for work because she can prep properly; apparently, sex at home is more spontaneous. It’s so cute hearing a porn star admit she’s self-conscious about making a mess!
First things first: This video is SO respectful.
AND educational. Which might make you think it’s not sexy or worth jerking off to. But it totally is! Tristan manages to include so much information into this video that you can easily flip between learning about how to give an enema to sitting back and getting erotically lost in an intense scene for three hours.
|This is a picture of my butt,
which I felt was appropriate
for this review
I hope I watched it all – it went on and on, it’s packed with scenes and info. I dunno, there might be some hidden butt plugs I missed.
Watching this video reinforced my respect for porn stars. They are such good, giving, game athletes. So refreshing to see people explore their sexuality in a shame-free zone. So many people are so secretive about their sex life and act like it’s a private activity that should be conducted behind closed doors, like going to the bathroom, so it felt very open-hearted for these performers to keep the door open for us on their backdoor activity.
These are professionals who want you to try this at home.
I love the conversations with the stars before they commence to fucking. There is more eye contact and kissing than you would expect for anal. Watching them kiss is what is personally hottest for me.
The actors have real chemistry and connection, they smile, appear relaxed, I get the impression they are friends in real life.
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!