An Interview with Rachel, Crossdresser

By Kendra Holliday | June 19, 2014 at 8:15 am

I'm just a sweet transvestite...

I’m just a sweet transvestite…

Last night I saw the musical Billy Elliot. In it, a boy experiments with wearing female clothes. I was interested to see older men in the audience show visible discomfort/disgust at the concept. It’s crazy how men dressing in women’s clothing is still so taboo in our society.

Meet Rachel, a 48-year-old man who is getting more and more in touch with his/her feminine side…

What is your sexual orientation?

I’m attracted to women. But being trans can blur what it means to be hetero or ‘normal’. Bi or lesbian? It’s a weird sensation being two genders at times.

How long have you fantasized about CD?

Since I was about 6 years old. I can remember having a Spiderman comic book that also had Wasp Woman and Black Widow in it. I liked Spiderman a lot, but I always wanted to be the Black Widow in her tight black outfit.

I also had very vivid dreams about being able to ‘wear’ a girls body. In the dream I would be a girl until I heard someone coming and I would change back instantly. After that there were only a few instances of trying on pantyhose. I mostly buried all desire to crossdress until about 7 years ago.

Are you married?

Yes. I have been married for 20 years to my one and only love. She has had a difficult time adjusting, I’m trying my best to be sensitive to her feelings while also true to myself.


My Teen Daughter is Repulsed by Cocks

By Kendra Holliday | June 15, 2014 at 8:28 pm

Sigh. Stupid dick pics

Sigh. Stupid dick pics

A while back I shared my stance on unsolicited cock shots.

I really don’t like them.

Some women don’t mind them. Some women even welcome them. In fact, you can feel free to send your cock shots to this website for review.

I’d prefer that over you sending them to my 13-year-old daughter.

Seriously, you guys are ruining dicks for her.

She’s been surfing the internet for almost four years now, and four times she has received unsolicited cock shots.

Each time, it’s like a disgusting slap in the face for her, and each time, she feels more repulsed by men and their junk.

The unsolicited cock shots have occurred to her in chat rooms, where she identified as a female and had a picture of a guinea pig as her avatar.


The Father, The Son, and The Wholly Man

By Matthew | June 15, 2014 at 5:00 am

“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.


Fisting Demo June 13!

By Kendra Holliday | June 4, 2014 at 9:00 am

Fistful of Dollars!

Fistful of Dollars!

I’m doing my FIRST EVER FISTING DEMO June 13. You can read more details and find out how to RSVP here.

I’ve only been fisted three times in my life, and I figured hey, now would be a good time to do it in front of a crowd of people. It’s always good to stretch your boundaries, right?

Actually, I was hoping someone else would volunteer, but the woman I asked to do it had to pass, because her female partner wasn’t comfortable with “the male gaze.” Personally, I’m fine with the male gaze and male energy, as long as it’s on my terms, which is why I want the crowd to be gender balanced for the comfort of everyone present. The men don’t want to be surrounded by men, and the women don’t want to be outnumbered by men.

Anyway, since I was going to be doing it with a new partner, and I haven’t done it since my hysterectomy, I figured it would be a good idea to get a practice run in before the demo.

OMG it was so intense and worthwhile!

And now, I can say I’ve been fisted four times in my life.

We had it planned for a Sunday afternoon. I had been looking forward to it for weeks, but the day before, I discovered an ingrown hair down there, closer to my taint, and the blemish bugged the hell out of me! It’s like getting a zit right before a photo shoot. Oh well, at least it happened now instead of at the big event.


Sexy Massage

By Kendra Holliday | May 31, 2014 at 5:11 pm

Touch me.

Touch me.

I came out of the shower wrapped in a towel and laid down on the bed. As soon as I did, Matthew recalled the time I pretended to be a massage therapist who had my way with him.

With the flip of a switch, he transformed into a man I didn’t know, who was giving a massage to a woman he did not know.

He put his big, warm, rough hands on my back and leaned down to ask, “How long are you in town for?”

“What?” I said, momentarily confused, but then I caught on. “Oh, until Sunday.”

“Are you here for business or pleasure?” he murmured as his hands swept down my back.

“A little of both,” I sighed with a tingle.

The towel covered my ass. He rubbed my arms, my neck, my lower back. “How did you hear about me?”

I replied somewhat shyly, “My girlfriend recommended you. She said you offer select clients a little bit more.”


New Sex Worker in Town!

By Kendra Holliday | May 22, 2014 at 5:52 pm

Sex workers just wanna have FUN!

Sex workers just wanna have FUN!

This is a guest post by my friend who just started doing sex work. I’ve been her mentor of sorts. It’s satisfying watching her evolve – I’ve coached many women, but none have jumped on it the way she has. I gotta say, I appreciate having a reliable, sane, sex-positive woman to recommend to my clients!

“Since my divorce a few years ago, I’ve been exploring my sexuality and part of that exploration has been attending sex-positive events and meeting people who choose to live open and honestly like Kendra.

As I read her blog, books that were recommended, and exposed myself to more sexual opportunities, I became open to things I’d have never dreamed of in my previous vanilla life.

When I saw Kendra’s event, “So You Want to Be a Sex Worker,” I thought it sounded like an interesting evening away from the doldrums of winter and also a way to take my mind off the fact that I’d been without adequate employment for months with no relief in sight. I did not go that evening intending to ever follow through with becoming a sex worker. After all, sex workers typically look like Pamela Anderson right? I’m no Pamela; I’m your typical middle-aged woman whose body isn’t what it was in my younger glory days but still has sexy soft curves.

I entered Kendra’s cozy little house; it was filled to the brim with about ten curious, confident women of all shapes and ages. I felt an immediate connection with the warm femininity that oozed from the room as we sipped wine, ate spicy hummus and listened to Kendra tell us about the experiences she shares with her clients and how the business end of it works. She encouraged us to take notes, ask questions, and if we felt so inclined to think about pursuing sex work as a viable financial opportunity.

My wheels began to turn as Kendra explained that most of her clients want experiences with sexy women who are competent communicators and confident lovers who want to make them feel special. I thought, “Wait, I’m all of those things!”

When I expressed concern about my not being a Baywatch babe, she assured us that there were clients with all kinds of sexual tastes and that some men actually preferred curvy mom types. I, along with a few others, later created personal flyers touting our “specialties” complete with photos giving a sneak peek of our body types. Kendra so kindly passes them to clients when she sees a compatible fit. Soon after, she told me that she’d met a nice professional man who had expressed his desire to hire someone who had a lot of the same attributes that I possess.


How Do I Enjoy Anal Sex?

By Kendra Holliday | May 21, 2014 at 5:15 am

Dear Kendra,

My guy is an ass man. Which is great because he loves my ass. What’s not so great is that he also loves to fuck my ass. I do not enjoy anal sex, but it’s something I would like to be able to do happily for him. We do it twice a year, but I know he’d like it more even if he isn’t actively asking for it more. The reason he isn’t actively asking is because he knows I don’t enjoy it, which is a turn off for him. There are two things I’d like your advice on.

First, I really want to be a good partner for him and give him great anal sex, but that seems to require that I enjoy it. Though I willingly give it, the act itself is so unpleasant for me that I tend to go silent during it, which is a big, obvious difference from my usually vocal self and a huge clue that I’m not enjoying myself the way he would like. Frankly, when I’m quiet I’m just trying to keep it together (“relax, relax, breath, don’t breath too fast, relax, relax, etc”). We’re trying some things to make it more enjoyable/tolerable for me: he always makes me cum first, I enjoy it when he rims me, pot (helped me with the last guy, haven’t tried it here yet), I’ve used a vibe during (did nothing to help), him using fingers first (almost as weird/uncomfortable feeling as the real thing), and yes we use tons of lube. But at the end of the day, do I just have to buck up and moan for him?

Second, he believes that everyone is equally capable of enjoying anal sex. Therefore, I should be able to enjoy it as much as all the porn stars do in all the anal porn he watches. I do not believe this is true at all, and when he says things like this I get the impression that he thinks I’m simply not trying hard enough to enjoy it; which is bullshit and makes me feel like he doesn’t appreciate the fact that anal sex is highly uncomfortable for me and I’m basically doing it just to be a good partner (it certainly doesn’t do anything for me). It’s like “Duh! Of course I would like to enjoy it, right now it sucks!” Who’s right, is anal sex for everybody or can it simply not be for somebody?

Anal sex is really his only non-vanilla desire when it comes to sex, and he’s been so good about accommodating my kinks/desires that I hate that I can’t seem to give him exactly what he wants in this one arena. This isn’t threatening our relationship at all, it’s just highly disappointing when it comes up. I know that anal is something you’ve “struggled” with as well, so I hoped you’d have some advice for me.


Virgin Territory: How to be Someone’s First Sexual Experience

By Kendra Holliday | May 19, 2014 at 9:00 am

Like a virgin – Hey!

My friend RainMan called me up one day and made a surprising announcement: “I’ve just been nominated by my friends to help a virgin learn about sex!”

“WOW congrats!” I exclaimed.

“Are you kidding?” he replied, “I can’t decide if this is a blessing or a curse! The fate of her sexual history is in my hands!”

“Good point,” I agreed. “You should always leave a person better than you found them. This is serious business.”

We discussed a gameplan, and off he went to…explore virgin territory.

He is 27, she is 24. They met at a party. Here is his story.

RainMan’s Tips for Happy Virgin Sex

Earlier this year, I had a rather unexpected opportunity come my way: being a virgin’s first. This would be my first time with a virgin. Kendra was kind enough to act as a sounding board for my thoughts and concerns, and I thought I’d put together a little guide for anyone else who might find themselves in a similar situation.



By Kendra Holliday | May 17, 2014 at 7:41 am

Blurred lines

Blurred lines

The threesome was such a surprise.

Matthew and I had been flirting with an old friend of mine for a few months now – she and I went to high school together, drifted apart, and had renewed our friendship this past year.

We’ll call her Andromeda – a golden goddess who exuded sexuality.

A married golden goddess.

For months now she had been telling us about how she and her husband were incompatible in bed – she had a higher drive. She liked being dominated, and he had no clue.

Andromeda was frustrated. Counseling wasn’t helping, and she felt trapped due to finances, kids, family… so she finally decided to cope the way a lot of people in the same situation do – by cheating.

We had hung out with her a few times and enjoyed the flirty sexual tension, but weren’t sure where to take it. She decided for us. She pointedly told us she wanted to spend an evening with us. She told her husband she was going out with girlfriends, but instead came over to our house in a breezy summer dress, bearing a bottle of whiskey and a big smile.

We STILL weren’t sure what to expect, but decided we were down with whatever unfolded.


Sex at Dawn: The Prehistoric Origins of Modern Sexuality

By Kendra Holliday | May 15, 2014 at 6:45 am

Sex at Dawn, paperback cover

Last winter, Matthew and I were at our romantic cabin getaway. We had just fucked and were lounging in front of the fireplace, sipping cocktails contentedly. The cabin closest to us was occupied by a couple also trying to get away from it all. Unfortunately, they weren’t quite succeeding.

They were having a big fight.

Doors slammed. Amidst the commotion, we heard the woman scream, “You fucked someone else last night – I’m not stupid ya know!”

We looked at each other with raised eyebrows.

I drawled, “I’m glad the fact that you fucked someone else last week isn’t ruining OUR vacation.”

“Yeah no shit!” he agreed with a swig of his drink.

We toasted each other.

More drama floated through the trees our way. “I’m leaving!” the man cried, got in the car and drove off. He came back a few minutes later, knocking on the door. “Let me in!” he begged.

I rolled my eyes and joked, “Do you think we should go over there and offer them some relationship advice?”

“Fuck no!” he grunted. “Let them get their own damn copy of Sex at Dawn.”

He was talking about the book, Sex at Dawn: The Prehistoric Origins of Modern Sexuality.


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Now I'm finally home and have a moment to reply to emails but I'm a total fucking pumpkin and am so tired! 😔💭💤


My mom & me at sis's book signing tonight @ St. Louis style shop on Cherokee!


From Prohibition exhibit at History Museum in St. Louis


From Prohibition exhibit at History Museum in St. Louis