By Kendra Holliday | July 7, 2018
Category Archives: Passion & Intimacy
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 | 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?
The Way of the Superior Man: A Spiritual Guide to Mastering the Challenges of Women, Work, and Sexual Desire
By Kendra Holliday | April 9, 2018
The book King, Warrior, Magician, Lover: Rediscovering the Archetypes of the Mature Masculine explores the archetypes of the mature masculine. Men who act out, have temper tantrums or are violent – jerks, bullies, know-it-alls and thugs – haven’t reached their full potential.
Men aren’t allowed to fully mature in our society. There is no rite of passage. The spoiled little princes of the world have work to do if they aspire to be superior men – if they want to be King.
So how do you become King? Here is the book that perfectly mirrors our relationship dynamic: The Way of the Superior Man by David Deida. I underlined the shit out of this book. There’s no way I can feature all the awesome points, so please get a copy for yourself if you’re interested in tapping in to what makes our relationship so explosively orgasmic and fulfilling.
My partner Matthew hasn’t read the book, but that’s ok – he’s living it.
Here’s the premise. In order to have a passionate relationship with someone, you need to adopt a feminine and masculine contrast. It doesn’t matter who possesses the masculine or feminine – you can be a masculine female/feminine male couple, or a masculine female/feminine female couple, etc. The author maintains that 80% of people lean one way or the other – they either want to be ravished or do the ravishing.
For the most part, Matthew does the ravishing and I greatly enjoy it, I soak it up like a slutty sponge. But every once in a while, we’ll turn the tables and I’ll ravish HIM, which is just as fun and exciting. If neither of us assumed the ravishing mode, things would be more even keel. And boring.
That’s what happens in so many relationships – after the thrill of new relationship energy dies down, we get lazy and slip out of Lover role and become Managers, Caregivers, and Roommates. Then we take our partner for granted and lose respect for them and the sex turns lukewarm and resentment sets in.
So many men complain to me about how their wife doesn’t want to have sex with them, which makes him feel hurt and rejected. The reason the wife is cold to him is because she doesn’t respect him. The reason she doesn’t respect him is because he has let her down.
David acknowledges that most men want to have sex with other women, even if they are in a sexually fulfilling relationship. He advises, “If you want to be with other women, make sure you are taking care of the woman you have.”
Check his stuff out on YouTube – here is an example:
This is one of the books I recommend most. Click here to view my list of Top Sex-Positive Recommendations.
Bonus link: The Art of Manliness
By Kendra Holliday | February 23, 2018
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 | February 8, 2018
Book cover art
This topic matches my life philosophy perfectly, which is:
As long as you take care of your duties and obligations and are not hurting anyone, you can have as much fun and pleasure as you want.
Simple enough, right?
Barbara’s book is about sex, but it’s so much MORE than sex – like I always say, our sexuality is connected with everything else in our lives. If we can address our sexuality without fear or shame, it frees us up to enjoy other aspects of our lives more fully.
Barbara Carrellas is a little woo woo,
Barbara shares so many of the messages I spout, but she does so in such a loving, compassionate, patient manner. She does an excellent job explaining concepts that might be unfamiliar to the reader.
Therefore, it would greatly behoove you to read this book, as it will clarify and reinforce many truths about sex in a way that will make you feel safe and empowered.
For instance, she teaches the Something More Factor. No matter where you are when it comes to your own orgasms, whether you’ve never had one or have more than one a day – you can enjoy Something More, if you desire. You can have more orgasms, longer orgasms, deeper orgasms – and orgasms are one ticket to ecstasy and bliss. Having an orgasm creates similar brain waves as meditation. (more…)
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 | December 23, 2017
After our spontaneous threesome the other night, I was SO eager for the three of us to get together again! I’m so greedy! I want more more MORE!
Lana came over, and we sat on the back porch and talked over cocktails, relaxing and catching up.
After a while, he asked her if she was down to play that night, and she said yes!
I love her hazel eyes, her bountiful hair, and pert nose. I’m a sucker for pert noses! She has such animated facial expressions, and tells such funny stories. I love her mannerisms. Very mischievous eyes. Also, she has an extremely smooth butt. It’s like really cute butter.
This time, he drew a bubble bath for two! We both easily fit in the tub. He gave us our girl time to sit and talk. He checked in on us, brought us drinks, it was wonderful!
Then we sat on the couch for a while to cool down, the two of us naked with towels.
He led us up to the bedroom, which was bathed in the golden glow of a small, bedside lamp. The king-size bed was adorned with chocolate brown sheets. Mood music played softly in the background.
By Kendra Holliday | December 22, 2017
Continued from previous post…
We arrived at Hustler’s Taboo night.
Thankfully, we were mature enough not to let anything interfere with our great evening, which is a good thing, because it got better every second…
Taboo was crowded and full of activity. They have quite a bit of equipment – a rope suspension section, couches, spanking benches, St. Andrews Crosses. All were in use, but soon a spanking bench opened up, and we seized it.
I went first so she could watch and get used to the energy of the place. She had some BDSM experience, but nothing public.
I eagerly bent over the bench. I was wearing a sexy little business top and skirt. The skirt hem was asymmetrical, so when I walked or bent over, you could see where my lace stockings met my pale thighs.
He worked me over, grabbing my hair, spanking me, lavishing me with good, hard attention.
I got hot and ripped off my top and bra. Lana glanced around surprised. They allow nudity here!
It was so stimulating and exhilarating! I kept laughing and giggling.
He pinned my arms behind my back and instructed Lana to tend to my top as he tended to my bottom. This guy parked himself right in front of me and stared hard. Not a problem, but he was a little too close for our comfort, so Lana stood at my head, providing a barrier between us. I’m sure he didn’t mind her ass in his face.
We were buzzed and happy.
Next, it was her turn. She had been smacked on the ass during sex, but never had a spanking like this.
By Matthew | December 22, 2017
Ed Note: Here is Matthew’s perspective of the sexy story I posted earlier this week! Another first date success story from the pages of polyamory…
Having been acquainted with this woman for almost a decade, I was happy she contacted me after her recent relationship ended. Here’s how it transpired….
“I need your help,” she blurted.
Aside from seeing her a couple times out and about, that’s the first message I received from her in more than year. I wasn’t quite sure if she needed help moving, or help with her taxes, or maybe some direct pressure on a wound?!
“Okay, but I’m gonna need more details here,” I replied.
“I need someone…”
“Go on,” I encouraged.
“Okay…I need a fuck buddy. Does that even exist? Is that weird?”
“Now we’re getting somewhere. Yes, it exists, and it is absolutely NOT weird!”
The conversation went on from there with me reassuring her that everything she wanted was totally acceptable. I asked her if she had a preference as far as type of person. Male? Female? Brown, white, yellow, big, small, old, young?
“No. I’m really not picky. I just want someone to hang out with, experience some culture, have some drinks, and have sex with no guilt, no drama and no real expectations. Knowing you….I figured you might know where to look.”
To which I replied, “Sounds perfect. How about I start with looking in the mirror?”
“I’m totally interested!” she exclaimed.
Yes!! I’ve always been attracted to her, and received great feedback from her to my flirtatious cues in the past. Now, the timing was finally right. She was well aware of my relationship status, yet still contacted me. That is a major factor in my choosing to see women for anything more than a platonic connection.
By Matthew | November 1, 2017
There are a great many resources on giving oral sex. From videos and articles, books and blog posts, one can find all kinds of information on how to give great blowjobs and eat some fierce pussy. But what about being skilled at receiving it?
Huh? Yes, you read that right.
Oral sex should satisfy both the giver and receiver at the same time, albeit not necessarily in the same way, but satisfying nonetheless. In order to make that happen, the receiver needs to be as active, at least mentally, as the giver. You have to find out what your partner likes. How? Here are some thoughts from my partner, Matthew…
|You deserve oral worship.|
1. Be Assertive
This is a big one. Don’t be afraid talk to your partner. This may take some getting used to for both of you. Some people find it embarrassing or “not right” to talk about sex openly, let alone talk while having it. Tell your partner what you like about what they are doing. Let them know they are making you feel good! “That feels amazing!” or “Yes!! Right there!” are great places to start.
You can also fantasize with your partner through speech. If you know about a particular fantasy your partner has, or you have one of your own, try acting that out. Maybe she is your secretary or co-worker. Maybe he is that young stud you’ve been wanting to have your way with for a while. Roleplaying and fantasy are great ways to live out desires without the possible repercussions of actually doing them. The possibilities are endless, but you’ll never know any of them until you try.
Lastly, but certainly not in the least, if and when you have an orgasm, in the name of all that is good; vocalize it. “Yesssss!!!” “I’m Cumming!!!” “Holy Fucking Shit!” or whatever comes out. (On the subject of whatever comes out: Men – do not surprise your partner with a mouthful of cum. You must let them know you are about to release so they can control where it goes. Unless of course you’ve talked about it and know what your partner prefers.)
2. Be Active
This can happen in numerous ways. Of course you shouldn’t immediately jam your dick down their throat or suffocate them with your grinding pussy. Start with a slight push toward them. Pay attention to their reaction or ask them if they like that. If they do, then you can push or grind a bit more. You’ll eventually find a comfortable amount for both of you. Keep in mind, everyone is different in their preferences. Some people like their face smothered or their mouth fucked hard and they get great pleasure from it.
Try touching their head, shoulder, cheeks, or hair in different ways. Remember always start lightly and move to more intense sensations. If you find your partner enjoys their hair gripped and head controlled, do it. If you find your partner likes his face ground into and thighs clinched around his cheeks, do it. It will make is more pleasurable for them.
3. Be Adaptive
Don’t get get stuck receiving oral in the same place, at the same time, in the same way, for the same reason. Try new positions like standing or lying on your side. Different environments can offer amazing amounts of excitement. Of course you need to be very mindful of some environments (i.e. elevators, cars, public bathrooms, dressing rooms, parking garages, wooded areas, etc.), but great pleasure can be realized from short sessions of oral sex. It doesn’t always have to be done to orgasmic completion. After all, foreplay and build up are great pleasure paths.
Certainly this list of thoughts and suggestions is just that. Everyone is different and derives pleasure in different ways. However, not many people want to feel like what they are doing is not appreciated. If you keep that in mind, you can come up with many more ways to make oral sex an even more amazing part of your life.
Now, go forth, and receive head.
What are your oral sex tips?
By Kendra Holliday | July 17, 2017
|The more you know,
the more you grow.
Earlier I posted something on how to suck dick. Since women are more complex, I won’t pretend to know exactly what they all want. Some like more pressure, some like less direct stimulation, etc. But I do know what I want, so listen up! Take notes for our date…
“If her legs ain’t trembling like Bambi, you ain’t eatin’ it right.” – from this HILARIOUS video about eating pussy
1. Start at my head and slowly work your way down. Kiss me, pet me, stroke my hair. Delight in the curves and valleys of my breasts, my belly, my hips, my thighs. I usually like lying on my back to receive your oral worship.
2. Kiss the inside of my thighs. Inhale my scent. Lick up and down my slit.
3. Sure, tongue fuck me and all that good stuff. Then, focus on my clit. The key is the right speed and pressure. Don’t glue your mouth to it. Back up a little to give your tongue room to dance. Pretend you’re a cat lapping cream. Or, gently suck on my clit like it’s a teeny tiny dick – because it is! We all have the same parts down there, just different shapes and sizes!
4. Keep it steady, focus. If you get tired (it might take a few minutes, especially if we’re new to each other) take a breather and kiss on my thighs again, or play with some sex toys, buzzz. But get back to it when you’re ready! And feel free to ask if the pressure/speed is right. And don’t be offended if I offer a little guidance – good communication is key to great sexy time.
5. I like it even more if you put a finger or dildo inside me while you’re lickin’. You can move it slowly inside and out, or just rest it there. The sensation of having something inside is nice enough just on it’s own. I like to feel it when my muscles contract with the orgasm.
6. You’ll know I’m getting close when my legs tense up and I get quiet. And you’ll know when I cum cuz I’ll hyperventilate and erupt with some sexy or primal noise, and possibly grab your head. I might even cry, “You’re making me cum!!!” If we’re in church, I’ll just whisper to you that I’m cumming, so that you know what’s goin’ on, you sent me over the edge, yessss!
7. You can keep it up for a bit afterwards, I don’t go instantly sensitive. And usually after I cum I’m good n’ wet, it’s my fav foreplay, and I’m ready to fuck!
But first, I’ll give you a gold star.
Ladies, how do YOU like your pussy licked?
By Kendra Holliday | December 25, 2016
End of the year recap!
Who here is glad to be done with 2016?
And I didn’t even have that bad of a year – I mainly watched other people’s loved one’s die and shitty world news and election travesty…
I can easily recall bad things, but if I think a little harder, I can conjure some really amazing memories this year –
Going to the cabin
Spending time with people who are no longer alive
Hosting fun events – Shameless Grounds, clothing optional pool party, sex worker workshops, sissy tea party, Fleshtivus!
Road trip with Sex Positive St Louis crew to Chicago CatalystCon
Tantra training in NYC!
A quick jaunt to Texas…
Fun with family – my daughter, partner, siblings and partners are still alive and well
New dishwasher, washing machine, and dryer – so many gifts and blessings thanks to my clients and loved ones
Another trip to NYC and the Poconos!
Lots and LOTS and LOTS of sexy time! Tantra, long distance clients visiting, devirginizing, fetish facilitation and roleplay realized….
And another year of good health – no serious illnesses or STIs, hooray!
And so many loved ones, a roof over my head, food in my belly.
Want to hear something funny?
By Kendra Holliday | December 15, 2016
The other day, I had a session with a 30 yr old man who has never been intimate with another person. He was a blank slate – didn’t even have kissing experience.
A few hours before we met, I posed a question to my network:
What would you teach a sexually inexperienced person?
The responses were so excellent, I had to share!
Self-pleasure – knowing what feels good to you is helpful before engaging others.
Sex can be sacred or profane. Sex can be spiritual or playful.
Sex is adult playtime. If something embarrassing happens, laugh it off.
The best sex is messy. That’s why we have showers!
Practice good hygiene and health. Learn how to use condoms. Pee and wash up after sex.
COMMUNICATION. Communication with your partner is critical. Always check in with your partner, ask for feedback. LISTEN to your partner.
The importance of CONSENT.
By Kendra Holliday | December 2, 2016
Kyle took the train from Chicago.
All day he traveled, portable oxygen tank in tow.
He didn’t listen to podcasts or music. His mind was too occupied with thoughts of what was to come –
You see, Kyle was overcoming great obstacles in order to find answers and rediscover intimacy with another person through surrogate sessions with me. It had been seven years since he was last with a partner, and he was missing human touch terribly.
Why? Life took an unexpected turn from him.
I’m always fascinated by my client’s life stories, and his was especially interesting.
As a forensic anthropologist, Kyle traveled the world working on ancient civilizations and gravesites. He was fit, had a passport, and worked outdoors a lot, in all kinds of conditions. Destinations included South America, Australia. He was next scheduled for a project in Europe, and had his sights set on Asia.
Then one day, at a church in Mexico, disaster struck – literally. The team was digging in trenches, excavating an old sacred graveyard for relocation. Despite wearing a Hazmat suit and respirator, something went wrong when a 400 yr-old-bone was hit with a pickax. Bacteria exploded in the air, and invaded his lungs. He suffered serious pulmonary damage, and has been on oxygen 24/7 ever since.
A couple years after that, he was hit in the ass with colon cancer, and had to undergo risky surgery to remove 1/3 of his colon. The doctors warned him he might not survive the operation, due to his lung condition. They had to give him an epidural and twilight meds instead of general anesthesia!
Incredibly, he survived this double whammy.
Nowadays, Kyle is the same age as me (43) and lives with his parents on disability. He can no longer drive. He’s overweight and in poor health. His lifestyle went from adventurous globetrotting to being tethered to a tank in his bedroom, more or less homebound, living vicariously through the internet. He is an odd combination of extremely worldly and intelligent, and emotionally stunted and childlike.
We had our initial consult over Skype. I found out he’s quite kinky like me – into stockings, men and women, incest and rape fantasies, pegging… all that fun stuff! His sensitivity and shyness put me at ease, and we clicked.
By Kendra Holliday | November 23, 2016
Just reflecting on how much I get grabbed.
Most of the time I like it.
After all, I have lots of handles.
Breasts, belly, hips… pussy.
Of course, I prefer to be grabbed consensually. Like this.
That was a good night – Ladies Night. I was weak all the next day.
When was the last time you grabbed someone? Did you ask first? Was it consensual? Did it lead to good things?