My Daughter’s Date Ideas
By Kendra Holliday | April 22, 2023
Category Archives: Passion & Intimacy
By Kendra Holliday | April 22, 2023
So, I’m reposting my daughter’s super sweet list of date ideas, from 6 years ago.
Aren’t they so charming?
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. Gosh, I adore him, he made it so amazing.”
He’s like a young George RR Martin, they’re so cute and nerdy together.
I’m SO happy with this new development. She tends to brim over with teenage angst and melancholy, so it’s wonderful picking her up from school and she’s smiling so hard, her face hurts. The rush of happy hormones and feeling connected to someone special to her is better than any pill she could take!
I asked if he is her boyfriend, and she said she didn’t know, but she would ask him. She has ups and downs, and frets over being too direct with him.
I reminded her that she is probably advanced in the realm of communication, and needs to be patient with others and teach them how to be open and honest. I also let her know that the wonder is part of the fun of the early stages of a relationship – infatuation is a trip, and you should let it last as long as you can! After that, you get into attachment, feeling the person is a safe haven, then anxious when they are not around, then finally, secure (if the relationship is healthy.)
That’s where I’ve been with my partner Matthew for the past six years or so. We can’t go back to the infatuated stage with each other, but since we are polyamorous, we can feel secure while flirting with other people and enjoying novel experiences.
Anyway, my daughter shared her list of curated date ideas with me and gave me permission to share them with you. I think they’re so cute! She made most of them up, and collected some from the internet. I want to do a lot of them, how about you?
By Kendra Holliday | April 19, 2023
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 12 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 | March 17, 2023
Below is a list of relationship values. Which ones are important to you? Are you getting your emotional and physical needs met? What about your partner(s)?
Acts of service
Feeling heard. Do they listen? If they get distracted, do they follow up with what you were saying?
Willingness to compromise
Partner enjoys spending quality time with your loved ones/chosen family
Supporting each other’s personal growth/mission: reading what you write, listening to your music, your podcasts, supporting your continuing ed
Versatility within sex life
Sex with different people
By Kendra Holliday | March 15, 2023
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 | September 8, 2022
Ed Note: This was originally published Sept 23, 2012.
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 | May 6, 2022
The other day, a friend I’ve known for years texted me out of the blue:
“Hi Kendra! After years of celibacy, I’m finally having sex again! He’s amazing. We want to experience many things together, can you give me advice on hiring a sex worker for a threesome?”
I was so excited for my friend! I let her know about these sites they could explore together, as well as searching twitter using keywords, such as #STL #GFE #datestl, (be sure and click on “latest” tab at the top):
I told her that if a couple is looking to hire a sex worker, it’s better for the woman to initiate contact, as that shows the worker she’s involved in the process and not being “dragged along.” I advised her to read the website instructions, and expect to be screened and pay a deposit.
By Kendra Holliday | April 9, 2022
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, adult virginity, anxiety, trauma, disabilities, or orgasm/genital 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, in between relationships, single/divorced/widowed, not getting laid, or curious about alternative lifestyle options (non-monogamy, kink/BDSM, sex work, etc.)
4. He has a fetish and is ashamed/seeking understanding and validation (“Am I normal?!”) or 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 | August 19, 2021
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.
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 Kendra Holliday | January 26, 2021
Ed Note: From the archives. I look forward to working with clients again in a more normal way later this year!
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 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 | 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 | July 3, 2019
One of the best parts of my job as a sacred prostitute is that I get to spend time with adult virgins. And every time I do, there is one less adult virgin in the world. 🙂
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…)
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