By Kendra Holliday | July 17, 2017
Category Archives: Passion & Intimacy
|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 | February 10, 2017
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 16, 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 four years or so. We can’t ever 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 | 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 7, 2016
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 | 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?
By Kendra Holliday | November 12, 2016
Going back to the cabin next month… looking at the pics from our visit earlier this year with great warmth and fondness… I’m ready for a break from all the madness!
You better believe the pics are hot – we were in front of a roaring fire all weekend!
We took this tasteful version of me wearing a vintage slip for facebook:
Then we took these classic nude photos for the blog.
By Kendra Holliday | November 12, 2016
This is our sixth year going to The Cabin!
It’s our favorite yearly ritual – stealing away right between the holidays and giving ourselves the best gift – time for just the two of us.
For 72 hours, we’ll be living in our own private universe where time and the internet doesn’t exist. In between all the fucking and frolicking, we’ll stoke the fire and eat cake at 2am, watch a movie, float away in the hot womb of the jacuzzi, listen to music playlists that celebrate different aspects of our lives, sip Maker’s Mark hot toddies at 6am…
Previous years have been epic. Last year was a Beethoven theme. Other themes have been BDSM, Ginger, Videos, Western…
I think this year’s theme will be Game of Thrones…
He is my Sun and Stars… I am the moon of his life.
We’ll be far, far away, experiencing something new, and something positively familiar. We’ve had another whole year to strengthen our bond.
Funny how driving four hours from both our houses feels like coming home.
He wrote this note to me four years ago, and it still holds true:
We need a cabin for a weekend together,
undress beside the ashes of the fire.
Your white gown smells of burning leaves.
It’s cold outside but I penetrate you with heat.
I keep you with every inch of my soul.
I love you.
I hate you.
I AM over you, peering down upon you worn and wet.
Reverting to your fetal shape in a torrent of emotion.
I am the man who defines you.
You are the woman who adores me.
A Burgundy box of worthless treasure in priceless proportions.
I will soak the thorny stem I place on your grave.
I am over you, in ALL ways.
We, Dear Slut, are far from over…..
By Kendra Holliday | November 11, 2016
Another incredible weekend at the cabin.
The cabin is under new ownership now, so they made some nice minor improvements, such as new furniture, bedding, and this sign:
…unless you have a sex blog.
We had a fire going ALL WEEKEND, which apparently is as bad for you as smoking cigarettes, godammit. I guess it’s a good thing I don’t have a wood burning fireplace at my house.
Here’s a pic of me in the hot tub from a previous year:
By Kendra Holliday | October 3, 2016
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 | August 24, 2016
Last week I lost another client. (Please read this previous post about losing a client before proceeding.)
He wasn’t just a client – he was a friend and lover, too.
D and I first met over two years ago – his doctor referred him to me after it was determined he would outlive his initial diagnosis of dying young. Now, it looked like he could expect to make it to middle age. With that startling revelation, he was able to consider pursuing adult activities beyond getting his college degree – sex. A relationship.
But he was behind all of his peers in dating experience, so he needed to seek ways to catch up.
Drastic, unconventional ways. Beyond OK Cupid.
So, we met for a couple of consultations and built rapport. Because of his breathing machine, D was difficult to understand, and he didn’t have the muscle strength to move as much, but his eyes – oh his eyes were so incredibly expressive. I spent many hours gazing into those beautiful, warm eyes.
He used a motorized wheelchair and had a hospital bed. His medical condition kept him feeling cold all the time, so his bedroom would be really warm. I felt bad removing his cozy blankets, but the excitement and passion we shared provided a different type of warmth. Even his cologne smelled warm, like a clean, masculine fire.
At the beginning of each session, D would ask a sex question, such as, “I saw this in porn – is it really like that?” or “Is female ejaculation real?” and we would come up with different themes to explore. We had such fun and educational sessions!
We kissed as best we could around the breathing tube. His body was solid, so I was able to climb around him pretty easily. Still, I always made sure he wasn’t just enduring something or have pain interfere with pleasure.
By Kendra Holliday | July 31, 2016
My friend Mitchell Tepper, Ph.D., MPH is working on a documentary project featuring injured soldiers and their sexuality. It’s called Making Love After Making War, and they are raising funds for the film. Of course I donated to this important cause, and wanted to let you know about it.
There are six days left of the campaign – won’t you please consider contributing sometime this week? Or help spread the word?
I met Dr. Mitchell Tepper last summer at an AASECT Summer Institute that focused on sexuality and disabilities. Mitchell, who has lived with a spinal cord injury for over 30 years, knows firsthand what it is like to live with a permanent disability, and he is passionate about teaching others how to make the most out of their unique situation. He is a husband, father, and sex educator. He’s also brilliant, ambitious, and one of the most positive people I know.
So, yeah, I believe in his work and want to support this project however I can.
Please take a look at the Indiegogo campaign and find out more. Thank you!
By Matthew | July 10, 2016
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 8, 2016
Oral sex worship 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 appreciated 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 logistical foreplay over email or text during the day so you can prime his pump for when you see each other that evening.
Take the tease trail. Start by kissing your most fortunate manly test subject on the mouth, temples, ears, neck, then slowly head south, kissing and licking his nipples, chest, belly – skip the dick! – thighs, balls, shaft, then finally make your way to his cock head. Murmur body-positive compliments along the way.
Once you’re there, open your damn mouth. I keep hearing from both men and women about these women with small mouths full of teeth. 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/spit/hands. Use your mouth at the head of the cock, and slick hands lower down/the base.