Trump: The Biggest Cockblocker of All Time

By Kendra Holliday | August 2, 2020

Masked up and ready

Since March, I’ve been contacted by countless men seeking intimacy.

In order to keep my loved ones safe, I’ve had to change my entire business model. I’ve met with about four clients a week for online talking consultations, which is all well and good, but that’s not what they really want.

They want SKIN TIME. They want hands on intimacy and practice. They want PLAY TIME. They want in-person SEXY TIME.

If I were to have booked as many sessions as I wanted, I could have scheduled five a week, which amounts to 400 sessions.

Instead, I had to be very careful and screen extra vigilantly, and insist on wearing masks, which a lot of people resisted.

I ended up trying seven masked sessions since March.

Three of those sessions felt safe and good. Four of those sessions did not feel safe and good.

I felt much more comfortable with the men who were as conscientious as I am; the men, who, if I had asked to ditch our masks, would have said, “NO WAY.” Those men were doctors. Those men were scientists. These men had a disabled family member. Those men had cowboy ethics. They cared more about other’s health and well-being than their penis and pleasure.

I felt anxious with the men who were cavalier, who rolled their eyes and chuckled when I asked them to wash their hands. They thought the virus was “no big deal.” If I would have suggested taking off masks (and condoms, for that matter!) they would have gladly done so.

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A Tale of Two Clients

By Kendra Holliday | August 1, 2020

Wear a mask!

I have two clients who have been wanting to see me for intimacy sessions since March. I told both of them that I would consider doing a masked session with them. Both are very nice, intelligent people.

Client #1 is a 32 yr old tradesman. I met him earlier this year. His response to my proposal is as follows:

“I’m personally not a fan of wearing masks so I’ll just wait until things get a little closer to normal or whenever you’re comfortable setting something up. 🙂

I would just like to throw out there that I don’t think not wearing a mask when with someone else necessarily means that someone doesn’t have good ethics.

From all the research I’ve done, I’ve concluded that wearing a mask has less than satisfactory results and that washing hands and keeping up with good hygiene practice has much more impact at keeping Covid at bay. Covid has been elevated to a sort of terrifying virus when it’s actually closer to the regular flu that happens every year with a little more power behind it.

I would have no problem being with someone who I know is practicing good self-care habits to actively prevent getting the flu and is strengthening their immune systems more than I would trust the effectiveness of a mask (which has to be a an N95 mask in order to protect against the virus particles. The Covid virus can easily slip through any other kind of cotton or fabric that’s being used as a mask.)

Just wanted to say that not all men who are choosing not to wear masks are synonymous with having low ethics. I’m trying to be as conscious and aware of the decisions I make and not just blindly follow everything the government tells me to believe about anything, including Covid.

Hopefully that comes across as sharing my perspective, as I’m not attempting to be divisive. 🙂

Client #2 is a 64 yr old scientist. I’ve been seeing him for years. He has opted for monthly phone sessions with me all this time, as opposed to seeing me in person. I showed him Client #1’s take on masks and Covid. His response is as follows:

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My Solo Tantra Awakening Ritual

By Kendra Holliday | July 31, 2020

Sacred stones and yoni eggs

Sacred stones and yoni eggs

Since I’ve been back from Tantra Training, I’ve practiced the Tantra Awakening Ritual with several of my friends and clients.

But get this – you can also perform the ritual solo!

To learn how, you can read Barbara Carrellas’s book Urban Tantra: Sacred Sex for the Twenty-first Century.

It’s actually super easy to do, but it helps to be coached through it your first time. I read Barbara’s book thrice before I went to her workshop, and it was only there that I was able to “get it,” with her walking me through it.

UPDATE: Now you can DOWNLOAD her 30 minute guided meditation here. Best $15 I’ve ever spent!

Tantra is like the City Museum in St Louis or House on the Rock in Wisconsin, or many other exotic and unique places in the world – it’s hard to explain it, you just have to experience it for yourself. And you can experience it WHENEVER YOU WANT, FOR FREE.

Tantra is about energy, being present, and opening yourself up to a deeper level of consciousness.

Awakening is rousing, getting in touch with parts of yourself you have buried or ignored. This can be spiritual, mental, or physical. So often we feel disconnected from our bodies, we’re so in our head thinking and worrying so much. REPLACE THE FEAR WITH LOVE.

Rituals are tools that help us focus our attention.

The first time I did the solo ritual, I was in a roomful of people, which might sound like an oxymoron, but we weren’t interacting physically with each other. We all lay supine on the floor separately, and Barbara encouraged us to breathe deeply, go with the flow, and make noise if we wanted to. Having other people’s energy present made it more intense – I heard heavy breathing, crying out, moaning, sobbing… I myself felt great tingling and waves of emotions, and then cried cathartic tears afterward.

Naturally, I wanted to try it at home by myself. Ideally, I’d like to schedule this self-care weekly. You can knock it out in 30 minutes, or you can turn it into a more elaborate ritual.

For my first solo ritual at home, I chose a planets and elements theme.

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Read Me: A Parental Primer for “The Talk”

By Kendra Holliday | July 7, 2020

Read Me: A Parental Primer for “The Talk”
Book by Lanae St. John

Ed Note: This is a guest post by an amazing member of the Sex Positive St. Louis community, Amy Van Slyke.

As a parent of two young children, I have spent hours agonizing over how to talk to them about sex. I mull over questions like, “When should I buy my daughter her first vibrator?” and, “How do I teach my son to be an attentive lover?”

I was not far into Read Me: A Parental Primer for The Talk, by Lanae St. John, DHS, CSC, ACS, “The Mama Sutra”, when I realized I had fallen into the trap that has snared so many parents before me… I was focused on the “how” instead of helping my kids develop a healthy understanding of, and attitude toward, sex.

First, I want to clarify that Read Me is not a step-by-step manual for parents about how or when to have “The Talk” with their kids. It is a guide for those who want to develop a safe, trusting, and open environment for ongoing conversations. Dr. St. John argues that our culture of shame and unwillingness to talk openly about sex condemns children to ignorance, misinformation and makes them vulnerable to abuse, STI, and unwanted pregnancy. She urges parents to take an active interest in helping their children develop a healthy sexuality since they cannot depend on others or institutional sex education to give kids the information they need. Through her use of research-based findings and personal anecdotes, The Mama Sutra, mother of two, provides parents with “The 5 building blocks” that they can use to navigate the awkward conversations about sex, and engage with children in an honest and constructive manner.

Communication, Consent, Respect, Pleasure, and Fantasy

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So You Want to Host a Play Party

By Kendra Holliday | July 6, 2020

Party in a box!

I get about 2-3 inquiries a week asking about play parties – when is my next one, if I know of any coming up, etc.

You all are brave to want to experience orgies in the middle of a country that is being torn asunder by a highly contagious pandemic! Masks off to you, my freaky friends!

Meanwhile, I’m over here sitting in pandemic limbo, trying my best to wait this crisis out. Events are on hold; I don’t even feel comfortable scheduling one-on-one intimacy sessions. ;(

That said, I have friends in St. Louis who are optimistically planning their own play party this October. They want it to be bi-male/trans friendly. They asked me for advice on how to host a successful play party.

First, you should review my party page – it has loads of good info, FAQ, and guidance.

Second, here is a checklist of things to keep in mind:

  • Location. Hopefully, you live in house that is conducive for parties. I don’t – I live in a 1000 sq ft fairy cottage that can only host threesomes, foursomes, and the occasional gang bang. You want a classy, clean space that offers several stations for playtime. I’ve rented houses in the past, but that can be risky. My best bet has been a community member offering to host.
  • Accessibility. Is your space accessible? I’m sorry to say I haven’t always considered this in the past. Regardless, you should state if it is or not.
  • Allergies. State if any pets live at the location.
  • Parking. How many people do you want to attend? 12? 50? 100? Make sure you include parking instructions in your party confirmation email.
  • Screening. Do you have a sex-positive network? I keep an email party list that has about 600 people on it. Every time I schedule a party, I send out a bcc email to the list and keep track of who responds. I try and curate a good mix of people.
  • Budget. Lots of supplies go into a party, so think about how much you want to charge for overhead. $50/person? If everyone pitches in, these nights can be unforgettable!
  • Do you want to have it catered? I always check with Shameless Grounds first for catering.
  • Drinks. Do you want wine and beer only? BYOB? Have ice and mixers on hand.
  • Other drugs. If you don’t specify in your rules, people will take liberties.
  • Privacy. Speaking of rules, most people attending play parties like to keep it private, so make sure and acknowledge confidentiality.
  • Mood music. Hire a DJ or think about playlists/stereo setup.
  • Good lighting. Adjustable, ambient lighting is nice. Most people like it dim. Real candles can be dangerous, so I use safe fake candles, light machines, lamps…
  • Safer sex supplies. Be sure and have condoms and lube handy at every station. Other good items to have on hand are towels, sanitizer, mints, small trash cans, well-stocked bathrooms…
  • Enough play stations. Do you have several beds? A massage table? A SYBIAN? Do you want to add an air mattress or two? Will this be a kinky party with spanking benches and crosses? Consider putting sheets on couches for easy cleanup.
  • Theme? I LOOOVE party themes, but I try and make them reasonable for most people.
  • Gender ratio. If you don’t carefully screen, you can easily end up with 40 single men attending. If your party goers love lots of female energy, consider allowing women to attend at a discount, or free if they volunteer to mingle with guests for a certain amount of time.
  • Volunteers. Speaking of volunteers, enlist a few friends to help you set up, host, clean up.
  • Icebreakers. People often arrive nervous, so think of icebreaker games or a demo to kick things off after people have had a chance to socialize for a couple hours. One time, we did a pussy parade, where every woman who wanted to could line up on a couch and show off their pussies. We had eight beautiful pussies lined up, and the guests slowly walked past to savor the view!

Here’s an example of the email I send out to potential guests, you can borrow language from it:

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Local and National Mental Health Support

By Kendra Holliday | June 23, 2020

I know this isn’t a sexy topic, but during this pandemic I’ve been getting lots of inquiries from desperately sad people. Some are suicidal.

I’m not a licensed therapist. My specialty is sex, not suicide. But I truly care about your health and happiness, and I’ve struggled with mental health my entire life, and have been suicidal myself.

Please browse this Links page under counseling for St Louis mental health professionals.

In addition, here are other resources:

National:

National Suicide Prevention Hotline

A free, 24-hour hotline available to anyone in suicidal crisis or emotional distress. Your call will be routed to the nearest crisis center to you. 1-800-273-TALK (8255)

National Hopeline Network 

Hopeline provides support with trained counselors through this national hotline to prevent suicide. 1-800-442-HOPE(4673)

Crisis Text Line

Crisis Text Line serves anyone, in any type of crisis, providing access to free, 24/7 support and information via a medium people already use and trust: text. Text, “HOME” to 741741

Trans Lifeline

Trans Lifeline is a grassroots hotline and microgrants 501(c)(3) non-profit organization offering direct emotional and financial support to trans people in crisis – for the trans community, by the trans community. 877-565-8860  https://www.translifeline.org/

Substance Abuse and Mental Health Services Administration

SAMHSA’s National Helpline is a free, confidential, 24/7, 365-day-a-year treatment referral and information service (in English and Spanish) for individuals and families facing mental and/or substance use disorders. 1-800-662-HELP (4357) https://www.samhsa.gov/find-help/national-helpline

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The Father, The Son, and The Wholly Man

By Matthew | June 21, 2020

“Fatherhood” by Viktor Mikhaylovich Vasnetsov

Ed Note: This is a guest post by my partner, Matthew. He is the father of two children.

A couple of weeks ago, I started hearing the yearly buzz of “Father’s Day” gifts, salutations and tributes.  I started thinking a bit more in depth on the subject of Fatherhood and what it means to me.

Being a Father is synonymous to me with being a man. I hear so many people speak of “men” they know or have connections with and then start divulging details about these people.

I know women who demand flowers from their husbands as a way of apologizing for an act of relationship treason.

I know women who are dating “men” right now, but speak of nothing but their shortcomings.

I know of “men” whose wives have gotten up and walked away from them while they were eating her pussy.

I know of “men” who don’t make an effort to spend time with their children.

I know of “men” who can’t separate business from pleasure and vice versa.

I know of “men” who are so weak themselves, that they show their “strength” by preying on the eager and ignorant.

I know women who have settled for a “man”.

I know of “men” who live in their mother’s basement.

I know of “men” who can’t dress themselves.

I am sure you know plenty of “men” like this as well.

If a man has children, they are his number one priority.

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How to Approach a Woman – Even if She is a Whore

By Kendra Holliday | May 27, 2020

Embrace your erotic side

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.

Kendra Holliday portraying vanilla. Photo by Stan Strembicki

Here are my biggest turns offs:
Pushiness/eagerness
Impatience
Stinginess
Immaturity
Entitlement

Here’s what turns me ON:
Patience
Maturity
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:
Contact me
Complain about my policies
Grumble about my rates
Try to penetrate orifices immediately
Push boundaries
Disregard feelings and safety

Here is how to create a lasting relationship with me:
Contact me
Be respectful
Respect my process
Be generous and value my time
Truly appreciate my openness and female energy
Savor the present moment

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No Shave May: Before & After Pics!

By Kendra Holliday | May 27, 2020

For about six weeks in 2012, which included the entire month of May, I did not shave anything on my body – legs, underarms, pubic area. (my recap video is here.)

This weekend, we had a shave party!

Let me show you the legs first. In this pic, I have one leg shaved – can you tell which one?

One of these legs is not like the other…

Let’s take a closer look:

Hairy leg closeup

I was glad to shave my calves – wearing skirts with hairy legs is fine. I loved feeling the breeze tickle the hair. But wearing pants or tights with hairy legs felt CREEPY and annoying.

Next, my crotch.

.

.

Just kidding.

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COVID Kendra?

By Kendra Holliday | May 19, 2020

Flirting with the Angel of Death…

Sigh…I would make the most beautiful vector. 💃😚

I’ve been keeping a list of people who have been wanting to share intimate space with me since mid-March, and it’s currently at 40 folks. These are just the ones who have been screened and verified! 😇🤓

Can you imagine if I went ahead and booked all of those sessions? Move over, Typhoid Mary – COVID Kendra would give you a run for your money! (Speaking of money, this is about ~$10,000 of income I’ve missed out on.) 💸

Typhoid Mary was famous for her peach ice cream – mine is over here melting! 🍨😝

It’s been super frustrating getting loads of inquiries from people who are seeking play parties, group sex, erotic encounters. I have to keep telling them now is not the right time to act on such fantasies.

Right now, we need to hunker down with our sexually creative and adventurous fantasies and come up with some future goals – beef up our “Fuck it List” (as opposed to Bucket List). And it pains me when someone who has been in contact with me for months or even years, emails me now, declaring that they are FINALLY ready to move forward with addressing their sexual issue. I’m sorry, but the timing is off.  It’s like being an unpaid DJ taking song requests from people wearing earplugs. And then when I offer them the option of meeting online, they inform me that they lack the funds, the privacy, etc. Stifling and frustrating for everyone involved!

My hands are tied…

I promised everyone I would get in touch with them when I’m ready to start seeing clients in person again, and gosh is that a mind-bending waiting game. The devil is in the details… 👺📝
What are the best resources for me with guidelines on how to keep my clients safe? I guess I need to research CDC guidelines for massage therapists.
For now, I’ll keep blowing you kisses from a safe distance!

You gotta blow hard

Earthworm Sex!

By Kendra Holliday | May 17, 2020

Guess what! My monogamy stint is officially OVER!

As mentioned in my COVID statement post, I’ve been monogamous with my partner of 12 years since mid-March. This is a big deal, because normally, I’m intimate with several people a month.

Earthworm sex!

Eventually, I’ll need to carefully venture back into the world of sharing physical space with others, and the best place to start is with my other partner, someone I’ve trusted for years. He’s been sheltering at his house, and hadn’t touched anyone for weeks. He even had an antibody test, which came back negative.

We decided on turning our reconnection into a fun experiment. We started by sitting across the room from each other wearing face masks, and having a detailed conversation on how our sexy time would go. We both confirmed our lack of symptoms and all the safety measures we’ve taken.

Next, we undressed, but kept our face masks on. Then, we thoroughly washed our hands and went to the bedroom.

I had a sheet down and some lube on hand.

Pretty

We laid down on the bed next to each other, but opposite. In other words, his head was down by my feet, and my head was by his feet. And we pressed our flesh together and touched each other all over.

We had earthworm sex! 🙂

Since he hadn’t touched anyone in weeks, it was especially delicious and electric for him – he got HIGH off my good energy, and I basked in his, as well!

We played with each other and shared orgasms, but really it was all the fun touching I liked best. Skinship! Gratitude!

Did we want to kiss and have our usual sexy time routine? Of course. But it was FUN to do something different, and it felt safer, which made us more comfortable and relaxed. And it was definitely an upgrade from phone and video chats. Improvise, adapt, and overcome!

And this was good practice for me, as I open up my intimacy channels next month. I recognize that my actions affect my partners. I’ll be selective and limiting the amount of people I share space with, which means I’ll need to adjust my rates and schedule. I’ll be setting up each session with different rituals and protocols – a conversation about what we’ve been up to, what would feel safe for us, and what we’d like to get out of the session. We must also agree to disclose any symptoms we experience in the days following our encounter.

I know you can’t trust everyone, but you can do your best to lay the groundwork for open and honest communication, and lead by example. If we don’t take some calculated risks, we’ll always be shutting ourselves off from others.

Creative sex for the win!

“Help Me Get Laid!”

By Kendra Holliday | May 6, 2020

Hello! Do I know you?

The other day, I asked my friends for advice on how to deal with all the men who contact me looking for sex. I told them:

Since I’m so out there as a sex-positive activist and everyone knows I’m in touch with my sexuality, I get a lot of man contacting me requesting female energy/sex. I tell them that is a service I offer. With some of them, they are agreeable to my way of doing things, but others can’t or don’t want to pay for intimacy services, which is totally cool. It means we want different things, and they can go look somewhere else.

But here’s where it gets tricky. Some move on, but some dig in and ask me for a bunch of free dating advice (I offer consults as a service as well), or, even worse, they plead with me to help them find women to have sex with for free. This baffles me – are they asking me how to date? Do they think I have a closet full of sexy women to go to and pull one out and give to them?

Men: How do you find women who want to have sex with you?

Women: Where are you? Why are you hiding? They can’t find you. Are you wanting to have sex with men? Are you picky, or will you get with almost anyone who asks?

I give them a couple quick suggestions and resources, and then usually I just have to stop replying to their messages.

To be clear, some of the men are entitled and lazy, but others have additional challenges such as anxiety, autism, disability, or social awkwardness.

Below, I’m going to share with you my suggestions, as well as advice from my friends. One female friend even wrote a guest post about it – you can read it here.

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An Open Letter to Men Looking to Date Women

By Kendra Holliday | May 6, 2020

A guest post from my friend Gigi Spanks:

The goddess Demeter

To the Men Looking to Date Women,

As a woman in my late 30’s, I have encountered my fair share of thirsty men looking to get laid. I have spent countless hours with my female friends, lamenting over the horrible dates and bad sexual encounters we have endured. These experiences, which unfortunately are too many to count, have resulted in many of us pulling back from the dating world. We are still here, looking for sex partners and hungry for cock, but we are harder to find, more guarded, hiding in the shadows.

So, if you are one of the many men who are complaining that they can’t find women to date / fuck, please read on as I am here to share 5 things to help you be more successful in finding the relationship you want…

1.  YOU ARE THE COMMON DENOMINATOR…  If you find yourself in a situation where no one will date or have sex with you, it is important to recognize that YOU are the common denominator. You need to stop blaming other people (women) or the circumstances for your lack of partners. Ask yourself questions, such as, why aren’t people attracted to me? what behaviors do I exhibit that drive people away? What do I want? Knowing yourself is an important step in being successful at dating. In addition, you should identify what you want from a relationship before you put yourself out there (i.e. casual sex, kinky sex, long term partnership). In some cases, paying for the services of a counselor, life coach or relationship consultant can help you and save you lots of time and frustration down the road.

2. YOU ARE NOT ENTITLED TO PARTNERED SEX… Partnered sex is not just about YOU and getting your dick wet. Partnered sex is about you AND another person that is turned on by and enthusiastically consents to fucking you.  In short, no one is obligated to have sex with you. If you are looking only to please yourself and not do the work of finding / pleasing a compatible partner, solo sex or paying a sex worker for their time / skills may be for you (you read that right, I said PAY for sex.  You have to either put in the time to develop a connection or pay a sex worker, no one gets sex for free…)

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Sex-Positive Etiquette for Men: Discussion Recap

By Kendra Holliday | May 5, 2020

On January 27, 2019, my not-for-profit local community organization Sex Postive St. Louis held a Sex-Positive Etiquette for Men discussion at Shameless Grounds.

Here’s the event description:

This event is free and open to all SEX+STL members.

Men – do you wish we had more female members? (Note: as of right now we have more than 4300 members on our Meetup group. I’m guessing it’s ~ 60% men, 40% women.)

Do you wish women were as fired up to get some action as you are?

When you attend our clothing optional events, is it important to you that there’s a decent number of women there?

Do you want to touch and be intimate with women?

Do you ever wonder how to best approach women? Are you successful in your dating endeavors?

Join us as we discuss sex-positive etiquette for men. We’ll give some examples of how NOT to interact with women online, and constructive suggestions on what works better. If you have questions, we have answers!

Please come if you would like to be more successful dating and hooking up with women. Come if you are a woman and want to share your experiences and preferences. Come if you are a man who is successful dating women and have some insight to share. Let’s all learn together and create a truly sex-positive space for everyone!

The reason why we hosted this event is because our female members informed us that they were being contacted by male members with inappropriate messages.

We have a member harassment policy in place. In addition, I made this quick video reminding men that our group is not intended as a dating or hookup site.

Here are examples of approaches that can be perceived as inappropriate:

  • Sending members you don’t know a message that you’re looking for sex.
  • Attending a happy hour and asking the women there if they will kiss any random man on the street.
  • Posting on the discussion board that we should host a penis size contest and make sure there are sexy ladies on hand to judge it.

When women get bombarded with strong questions and messages like that, it turns them off and drives them away.

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Flirting Tips for Men

By Matthew | May 4, 2020

Dear Kendra,

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?

My reply:

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….

Matthew says:

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.

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