Why men find wooing so difficult

Unless you have been living under a rock your entire life, at some point you will of heard at least a hint of a whisper of the derp women face on a regular basis. And it is bad. It really is. Women have been self reporting on this on a consistent basis, but these reports regularly seem to get dismissed as exaggerations or women making a big deal out of little things and being dramatic.

Occasionally, a guy will get curious and go try a female profile before coming back wide eyed saying “Holy shiiiiiit they were NOT exaggerating in the slightest!!”

So why is it that men find wooing so hard?

Because they have never needed to before.

Throughout most of human history, women were second class citizens at best, if they were not property outright, to be transferred from father to husband. Marriages were mainly business arrangements and two people marrying for love or desire was unusual. When you could not own property, vote or have a job, you took the husband that came along and made do.

Women have been labeled “high strung ” and “hysterical ” throughout the ages, but if you were essentially living in solitary confinement with no job, money or options with some stranger you were married off to that probably didn’t even know what a clitoris was, is it any wonder women would occasionally go a little twitchy?

Those mouth breathing basement dwellers firing off the endless “heyyyy bb, wanna fuk??” emails that clog inboxes the world over would have had women back in the day, usually through arranged marriages. It didn’t matter your lack of social skills or game, you could get a companion. But now women can have jobs and own property and have options outside of getting a ring on the ringer and settling down to cooking and churning out babies. And men haven’t quite adapted to the new order of things yet.

I get that asking out someone is hard, and endless rejection starts to grate and wear down one’s self esteem after a while. But who exactly are you doing the asking to?

I have picked up my courage plenty of times and asked and gotten turned down flat. It stings. But you pick yourself up and ask someone else, hopefully under more successful circumstances. The *DIFFERENCE* is that men will overlook the rather obvious clues of “head down, no eye contact, walking away rapidly, a profile saying not interested, not single and not looking” and ask anyway, then get frustrated at their lack of progress. All women quickly get lumped into the “stuck up cunts” category, whereas if they had stopped thinking with their dick for 30 seconds they could of seen that the asking was futile as the woman is clearly saying “not interested, not going to happen.”

So for the first time in history, men actually have to woo women. And as it turns out, they tend to not be very good at it. They haven’t had much practice.

Lies we tell ourselves

We all have that voice. That nagging negative voice that never shuts up. That voice that keeps telling you how everyone is judging you, that they don’t like you, that they are thinking poorly of you. It can be so bad that simply walking down the street can be a miserable experience. Because certainly everyone is looking at your stupid outfit, your messed up hair and dirty shoes and thinking about what a dumb ugly loser you are.

Let me clue you in on a little secret my friends. No they aren’t.

That is your ego talking. How big is your ego that you think that people are busy thinking about you? That people are taking time out of their busy lives to even bother having you ever cross their mind? People are not judging your hair, outfit or face when you walk down the street because they never even get around to thinking about you in the first place.

Don’t believe me?

Try getting six inches cut off your hair and changing the color. Not even your best friend or husband notices. Ever had someone bemoan the “huge giant Mt. Everest sized zit” on their face that is ruining their entire day? A zit that with a magnifying glass, perfect vision and a finger helpfully pointing to the exact location you can maybe kinda see if you squint really hard? What you think is blindingly obvious about your personage is not even remotely noticeable to others around you.

People are not judging you because they never get around to thinking about you in the first place. And this realization was one of the most liberating realizations I have ever had in my entire life. I am completely free to be me. I do not have to live my life for others. The freedom and relaxation that I get to wallow in due to this revelation is an incredible feeling and I recommend it highly.

Once you realize that nobody is judging you or thinking about you, that the universe that is “You” never even blips across other people’s consciousness, you learn that the voice in your head is lying to you. That negative nagging voice in your head? It is full of shit. Kick it to the curb. The day I learned that voice was a liar was the day I was reborn. It was like struggling to walk in a heavy soaking wet winter coat that I suddenly realized I could take off and feel sunshine on my flesh. And I have been reveling in the sunshine ever since.

Be you. Be the true you. You are free. Nobody is judging you. Nobody is thinking about you. Go out and be the very best you that you can possibly be while you are on this planet. And tell that stupid lying voice in the back of your brain to suck your dick, it is certainly not doing you any favors.


But nobody reads anymore…

Nobody reads these days they say. Reading is a dying art. Everyone is on the computers, high tech, wired for sound, surfing on that digital highway. Who bothers with READING?!

Well, except for the small fact that all everyone is doing on computers is reading. Computers are words everywhere. You can’t get online and log into a website without being at least moderately literate.

Which is why getting messages riddled with text speak and abbreviations like “hru bb?” drive me right up a wall. There is no excuse. “Baby” is only 4 letters. What are you doing with your time that is so precious that you need to abbreviate it down to “bb?” Are you busy discovering the cure for cancer? Probably not. Add the damn “a” and “y.” Or when (and this has happened to me so many times that I lost count) someone messages you about something that is right on your profile and when you point out that the info is contained on your profile, they respond with “I don’t have *time* to read profiles.”

Um. Do you have ANY idea how someone that can’t be bothered to write to you in full sentences or read your profile comes across as someone that would be absolute crap in bed? If you can’t bother to spell out “How are you?”and just fling a “hru?” in my general direction you are not exactly coming across as someone who cares if I ever end up cumming or not.

Think about it. This is the message you are sending: “I can’t be bothered to read your profile, and I can’t take the time to use real words with you, but I promise I am going to rock your world!!”

I get it. I really do. You have taken the time and crafted out careful emails, thoughtful emails, put effort and energy into it, and you get back nothing. So you develop a severe case of “fuckititis” and just start slinging out the copy pasta. And that is when your chances go down from slim to none. When you put in zero effort in contacting someone, what you are really saying is “I need a body. Any body will do. As long as it is warm. YOU! You will do! How about it bb?” Your serving of copy pasta that you are flinging out to every person in a 100 mile radius? Not getting a lot of responses on it, are you?

You are going to say you are playing the odds. That you can’t be bothered with effort anymore and are just casting a wide net. *Something* will land it in. But think about it. The woman that can be wooed with an email reading “lookn fiiiine lil mama!! Wanna fuk? 3====D ” and is willing to meet up and part legs based on that well crafted Shakespearean sonnet would be so riddled with diseases that I wouldn’t risk touching her with a full body condom on. And I bet your wallet would be missing after she left.

You get out what you put in. And when you are just randomly flinging cold copy pasta at every warm body that comes into your view, you are not putting in very much. Think about it.

But hey, what do I know? Keep doing what works for you. If it is working so well for you, by all means keep it up….

I’m gonna give her a compliment. Bitches love compliments!

Your intentions are good. I get it. Here you are attracted to someone of the female persuasion. What to do about it? The ladies love being told they are hot. Chicks dig that sort of thing, am I right? So you do the logical thing: tell her just how sexy that ass happens to be.

You: “Damn, you are HOT!”

or “I love your eyes” (hair, lips, etc etc)

or “Your tits are the best tits I have ever seen!!”

Bitches love being told how attractive they are. This is a done deal. You sit by your inbox waiting for the responses that are due to come rolling in and you get…nada. Zip. Zilch. What could of gone wrong?

Let me break it down for you. Women get told they are hot on an almost daily basis. It is a useless compliment in the end. You are attracted to the meat envelope I happen to lugging around? Dandy. You like my body. A body that is 100% guaranteed to shift, fade and change. If the contact we have is you being one of many to admire my meat envelope, the honest truth is that it isn’t going to make much of an impression.

So how CAN you pay a compliment to a woman? Why do we make this stuff so HARD? You are just trying to be *nice* here!

As it turns out, even if a woman is posting pictures of their naked body all over the place online for the whole world to see, compliments of how nice her pussy appears to you isn’t going to make as much of an impact as you might think. Oh sure, there are some woman that crave being told how hot their tits are and stockpile up those compliments like Gollum craves that ring, but on the whole even kinky as fuck women are looking for something a little deeper than “nice ass!”

Instead, take the 30 seconds to read a profile. See what she is passionate about. See what excites her. She makes her own accessories? Tell her how good that hat she made looks. She is into animals and does rescue work? Tell her how inspiring you find that. She likes to read? As her what her favorite books are. I guarantee you will get more traction with that than with “daaaammn girl you are HOT!!”

Try it. Try approaching the people you are attracted to as a whole person, not just a series of appealing body parts. I guarantee you will have more success than your current methods…

Best of luck!

Do not blindly put your trust in Community Leaders

It is human nature, really. We love to idolize. We are so quick to hero worship, popping people up on pedestals at the slightest notice. The only thing we like more then elevating people is knocking them right back down.

When you first enter the Lifestyle, you will notice the “leaders” right away. People defer to them, they are seen everywhere, doing all the things, people hang on their every word, words that seem to carry more weight then the average kinkster’s words or thoughts. Look at their high status and how respected they are! Clearly these are people to idolize!

Yeah, I am going to call bullshit on that.

Let me tell you a little story about a “Community Leader” I met in my first few months of entering the Lifestyle.

He had written a book over twenty years ago and was still coasting on that fact. He was seen everywhere, he had opinions, ever so many opinions, that he would gladly share with you at length and in great detail. Here was a “Community Leader” in all it’s splendor.

When he focused on little ol me, I was both honored and humbled. What did this great Community Leader want with me?! He kept invited me out to lunches, ostensibly to lay on me all this great wisdom and knowledge he had at his disposal, but I couldn’t help but notice he wasn’t really giving me advice so much as talking about himself. Then he brought up mentoring me. How flattering such a Community Leader wanted to mentor me! What a great honor. Except I had not been looking for a mentor nor asked for one.
I made it to the 3rd lunch with this great leader, lunches he kept arranging and setting up. He seemed very eager to be a part of my life. It was on the third date he said “Well, I have a fetish for intelligence. You are very intelligent, it was how you made it to a third date.”

A date? Say what? He had never mentioned these lunches as being dates, not once. The only reason I had been showing up for them was because of how insistent he was in arranging them. My knuckle whitened on my fork as I sat there looking at a man with a good 30 years on me, a man who knew I was already in a relationship, a man so determined to set up repeated lunches and offer his…um…mentoring to me, and I saw no Community Leader.

I just saw a man. A man like any other. Human. Not special or worthy of some sort of elevation. I got through the lunch as politely as possible and then never spoke to him again.

Are there Community Leaders out there that sacrifice much and ask for little, that put their time and energy on the line, that are great examples to the rest of us? You bet your sweet ass there are. And they deserve our gratitude and appreciation. But just because someone has some higher visibility in our community does not mean their motives are somehow more pure. They are just as fallible as the rest of us. Be careful who you idolize, as idols can fumble…

Keep it kinky my friends,

Presenting “Learn how to lick: Oral Sex 101″ at the SF Citadel

On Tuesday Nov 25th from 8 to 10 pm I am presenting my Oral Sex class “Learn how to lick” at the SF Citadel 181 Eddy St San Francisco CA. $15 in advance, $20 at the door.

Love downstairs action? Are you a fan of oral but want to to increase your skills? Afraid you suck at sucking? This is the class for you! Rain DeGrey, fan of all things oral, proudly presents “Oral Sex 101: Learn how to lick.”

Tips and techniques, covering positions, safer sex and conquering deep-throat, this class has it all. Both male and female oral sex techniques will be covered, and there will be live demos of the concepts covered.
Come prepared to learn in a fun, non-threatening environment.
This is a pansexual class open to all genders and orientations, everyone is welcome!

Rain DeGrey is a writer, educator, rigger and fetish model and has been presenting classes for the past 6 years. She is extremely passionate about the lifestyle and considers education and serving the community an important part of what being “kinky” is all about. Demystifying and encouraging the joys of BDSM is the main motto she lives by and puts into practice daily.


Education at The Citadel

Education at The Citadel

False facades and the damage done

I have done it, you have done it, we all have done it. Whether it is sprucing up for a job interview, hiding the tattoos for a family reunion or putting your very best persona for that first date, we have all donned that false mask for a situation or two.

I used to all the time. Suppress who you are, watch your tongue, be polite. Hide the demon that lurks inside. Don’t talk about this, repress that. Dress nice, put a hat over that mohawk, take out that piercing. I spent years trying to be someone I was not. Not anymore. There was no more liberating moment in my life then the day I decided to be true to myself and stop hiding behind that false facade.

How many of you have gone on that date pretending to be a completely different person then who you actually are? Pretending to like sports, or a certain TV show, switching political affiliations, completely failing to mention your love of kink when in real life you are the complete opposite of everything you are projecting into that mask?

What is your secret plan, trick them into falling for you and once they have become habituated to having you in their life letting the mask slip? Wait until you have been dating a year before bringing out the flogger and finally admitting that you can not stand their favorite movie? What a disservice to the both of you. What a waste of both of your time. We are only given a limited time on this planet, why are you going to waste your time pretending you are something that you are not?

I refuse. I will not. The day I finally was able to let that false mask slip down and be the real true me was the day I was reborn. I will not give a minute of my precious time pretending to someone that I am not. I am not saying this realization is a free pass to be an asshole, being true to who you are does not give you the right to be a dick to everyone around you. But I will no longer invest a single precious second of my limited time in wearing false masks in an attempt to somehow please others around me. You can never please everyone around you, it is impossible and you will wear yourself out trying to do so.

If someone can not accept who I am, if someone finds me unpleasant and distasteful in some way, GOOD. I would much rather be honest and true to who I am and allow others to decide whether or not they want to interact with me, the real me. The effort and energy required in keeping up that false mask is draining and I one for one refuse to engage in it anymore.

If the only way you can get off is getting sodomized with a carrot while dressed in a bunny suit, you make that clear on the first date as opposed to lingering by the produce section at the grocery store heaving wistful sighs when you go shopping with your partner.

You CAN do it. I believe in you. Be true to you. Do not live your life for others. It is draining and ultimately futile. And if carrots are what works for you, wear that bunny outfit with pride!

Keep it kinky my friends,

Fantasy is always better than reality

When I was eight years old my mother found me in front of the linen closet at around midnight removing a pillow case from one of the higher shelves.

“Now Rain,” she said “What are you doing getting another pillow case? You already have one on your pillow. It is very late. You should be asleep!”

I looked up at her with my big blue eyes and replied, “I am getting a pillowcase to put over my head so that I can imagine that the bad men have kidnapped me.”

That’s right. I was live acting out abduction fantasies at the age of eight. Don’t judge. My mother, bless her hippie heart, didn’t judge either. “Ok Rain, we can go back to bed, you can put the pillowcase over your head and then you can tell me what happens.” My mother has always been very new age and accepting. I am sure she thought me talking it over would be very therapeutic. We walked back to my bedroom, I put the pillowcase over my head, my mother sat on the edge of the bed and I tried to say out loud what I had been thinking before I had been so rudely interrupted.

And a very interesting thing happened. It was no longer fun.Instead, it was bloody terrifying. Even though I knew it was only my mother at the end of the bed and not some scary bad guy, all the excitement had fled. It was just frightening. This was my very first realization of a sad truth: Fantasy is always better then reality.

In Fantasyland, nobody has bad breath or zits. There are no awkward pauses and everyone always says the right thing at the right time. Everything is in soft focus and smells amazing. I honestly hope you never get a fantasy fulfilled. Because I can guarantee you that it is not going to live up to what you are carrying around in your head.

Don’t believe me? Let me lay on you the story of the time that I was finally going to get that abduction fantasy that I had been dreaming of since I was eight. My Dom at the time knew just how much I had been fantasizing about it and finally decided to put it into action. He “abducted” me while wearing too short camouflage shorts with his long skinny legs sticking out like stork legs. It wasn’t how I had always dreamed it would be, but I can be flexible. We were going to make this work. He handcuffed me, wrapped up my mouth hole securely with a duct tape gag and we were off to a secret location for all sorts of deviant activities.

Except there was not enough room in the trunk to shove me into, so he had to put me in the passenger seat. It was ok. No worries. We could make this work. He thoughtfully seat belted in my handcuffed ass, as my hands were not good for the buckling, and then we were off to the abduction!

There were a fair of red lights on the way, and at one of the stops a man walked by in the crosswalk, made full eye contact with my duct taped and handcuffed ass less then 3 feet from him before picking up his pace and hurrying away, head down. Well. Reassuring to know if I was really being abducted that the world is full of good samaritans willing to get involved. I was already feeling any tingle of excitement of this scenario slowly deflating like an old ballon.

And then a few blocks later the car ran over a nail and got a flat tire.

My would be abductor had to get out of the car in his ridiculous shorts, attempting to change the tire as I languished in the passenger seat in my handcuffs and duct tape. It was, to put it mildly, a complete boner killer. The abduction was called off and I never attempted another one.

So, I repeat, I hope you never get your fantasies fulfilled. Whatever you are carrying in your head is not going to work out. Trust me. It is going to be inevitably disappointing in some way. Instead, enjoy and revel in the moment of what is happening directly in front of you. It doesn’t matter if they are not airbrushed and there are some awkward pauses, it will still be fun, and more importantly, real. Leave those fantasies in your noggin where they belong, where cars never get flat tires and abductors always wear long black pants.


It is harder for women


It is harder for women…

Being alone, bored and horny is a dangerous combination for anyone, male or female. The internet is an amazing resource that increases your interaction potential by staggering amounts that previous generations could not possibly begin to comprehend. It used to be you were largely limited by the available pool of pussy in your town or city. Now you can talk to people all over the world! And there is SO much pussy on the internet. Pussy that doesn’t seem to be wearing that much clothing, pussy that seems to be gagging for your cock, pussy that is just hanging around waiting for your Magic Peen to come by and grace it with your presence.

So you do the easiest thing in the world. You shoot out an email like “ u r hottt!” or “wanna fuk?” or “sexxy! can i cum over?” (These are all word for word emails that I have received over the years BTW) without taking the time to see if that pussy is even looking for fresh dick and are shocked, SHOCKED that the cock starved pussy dancing in front of your face doesn’t immediately take you up on your generous offer. So shocked that you start yelling at the pussy, calling it fat or ugly or fake or secretly a guy. (All things that have been said to me. Evidently I am actually an ugly fat guy. Fooled ya!!)

Let’s break down what went wrong. All you have succeeded in doing is pissing off the pussy and making it more cynical and guarded. A wave of low grade hostility spreads. The pussy is that much more unapproachable to the next email that comes along. They are tired of being hassled and yelled at. Nobody wins.

Look. I get being horny. Believe me, I do. While a guy will NEVER truly be understand what it is like to go through life as a woman, I am going to attempt to explain it a little. It is so much more risky for women to meet up with men online that words will never do it true justice, but I am going to do my best.

A woman risks pregnancy from a sexual encounter. This makes her much less likely to cheerfully jump on the eager cock that shows up perkily in her inbox all ready for action. While there are steps, from condoms to the pill to abortions, the risk of pregnancy in a sexual encounter make a woman less likely to spread it like peanut butter.

Even in this day and age, there is a double standard. If a guy gets a lot of action, he is a stud. If a woman wholeheartedly explores her sexuality, she is a slut and a whore. Knowing the judgment that comes with an active sexual life doesn’t make a woman super inclined to jump on your dick just because it is available.

And lastly, and most importantly, imagine that what you have to fuck is stronger then you and can overwhelm you at any time. Historically, the worst thing that ever happens to women is men. I am in no way saying that women do not murder and dish out domestic violence, but try and picture that what you have to put your dick in can overpower and rape you anytime it feels like. Imagine turning on the TV, reading the newspapers, and seeing endless accounts of men’s bodies being found in rivers and empty fields. Imagine knowing a huge percentage of your friends that have been raped and hassled in countless ways, and it happens all the time, everywhere you look. It would make you somewhat less likely to just run over and thrust your cock in that pussy just because it says “available and ready big boy!”

So yes, women are going to want to talk to you for more then one email. They are going to be reluctant to give out their phone number. They have a hell of a lot more to lose then you do, and their survival instinct over millennia of dealing with males doesn’t make them much inclined to jump in their car and drive over to your house just because you emailed them a photo of your dick.

If you don’t rush them, if you don’t insult them, if you take the time to actually read a profile and see if they are even looking fresh dick in their life, if you show interest in them as a person as a whole, I promise that your internet experience will be a lot more pleasant.


Just imagine…

Imagine having me for a sister-in-law and having NO idea who I am or what I do. Imagine thinking of me as your slightly odd, all black wearing, vegetarian sister-in-law from California, but having zero clue of the fervor and dedication of my entire life to all things kinky.

I met the boy when I was very young. We were both working at a book store and he picked me up in the philosophy section, where we bonded over a mutual distaste of Sartre’s “Being and Nothingness”. I moved in 3 weeks later and the rest is history. He has been with me for every step of my journey, never judging, always accepting and supportive of my life choices.

“Hey, I am actually kinky and want to explore that a bit.”


“Hey I am actually bisexual, no pansexual, and want to explore that a bit.”


“Hey I am actually kinky enough that I might want to try some fetish modeling, but don’t worry, I will never ever do any boy/girl stuff.”

“Actually, I am going to do some select boy/girl after all.’


“Hey I am actually poly and I want to explore that a bit.”


This isn’t to make it seem like he is a total passive pushover, far from it. He is a very strong and confident person. He just bought the ticket and is taking the ride. It takes a strong person to hang with me and the way I approach this journey called life.

We even ended up married and buying a house together, not that I stayed at the house 7 days a week or anything. I am much more of a feral cat as opposed to a lap dog, but whenever I came home I always felt welcome. We made it work. He never let his family know my…proclivities, as far as they knew I was just one of those wacky CA girls raised by hippies that was not down with the meat eating. They are clueless as to what exactly I get up to on the internet. Everything was all well and good until this week, when the in laws decided to come out and visit for the very first time. Bringing with them my 18 month old nephew.

I have never had a baby in my house before. My house seems to be a bristling trap full of bricks, sharp objects and glass spice containers placed way too low. I have hidden all things kinky. I think. But I am sure there is something I have forgotten. My dog also has managed to develop her very first UTI and has completely lost all bladder control. The hose house reeks of pee and my poor dog is in diapers. The in laws will be at my house for a full 9 days, while I pretend to not be kinky and have to come home faithfully every single night, dodging the dirty dog diapers and scattered children’s toys. I am quite certain the effort in maintaining a vanilla mask for such an extended period of time is going to make my kinky little head implode.

Wish me luck. I am going to need it.