A MAJOR MILESTONE or How I Got In To This In The First Place

From 2015/10/12 with a significant addition today 2017 05 09

Just for you Alex

Three years ago (update to Four years ago) September 30th 2012 was the first time I ever heard of crossdressing.  No kidding.  Until then I thought it was just guys joking around, comedy.  The Scottville Clown Band.  No idea at all.  Never looked in to it.  Never gave it a thought.

Three years ago (update to Four years ago) October 11th 2012 was the first time I ever crossdressed.

Three years ago (update to Four years ago) October 12th 2012 was the first time I ever went OUT enfemme.

It all happened only because………………………………………….

I was just looking for a photography studio to take some classy, tasteful, glamour photographs of my wife because she has really gotten herself in to shape. She needs to see herself as I see her. I stumbled upon an entirely different category of glamour photography for something I did not even know existed, crossdressing men! Some of the places that do it called it a “transformation”. I had never imagined this existed, it wasn’t even on my radar. But the funny thing is for some reason that seemed like something fun and exciting.

So I did some more searching and found that there are a LOT of places doing this “transformation” thing all over the world. I also found transformation places in Chicago, Milwaukee, Ohio, and even in Texas. The Texans are probably doing transformations from cowboy to cow girl but they probably use red holsters, pretty little .6 shooters, and a pink something.   (To the thousands of cow whatever readers: Please don’t send angry letters, I admit I might be wrong.) Not only are there a lot of transformation studios, there are also probably a hundred businesses throughout the US providing supplies to this “industry”. There are regular gatherings in larger cities and even nationally advertised conventions. I found support groups and places that host “Girls Night Out”. So there is a lot of stuff going on, all for guys dressed as women. Believe me that some of these guys, if they were women, would be HOT! But they are still guys. I had NO idea. I toyed with the idea of getting my picture taken. One thing was certain: If I was going to do anything it would have to be a secret from everyone but my wife and it would have to be somewhere else because there was nothing like this anywhere in Michigan. Also I would have a lot to lose if I was exposed because crossdressing could cost me my job, reputation, even my relationship with my family.

With those obstacles I just dropped it. I dropped the thought, only a little disappointed. Life went on as always, as usual, all gray, blue, black and brown in cotton and denim. Boring.

Until less than a month later and all but by accident………………………………

Now look at me!






First Time OUT Enfemme Just Four Years Ago
2017 05 09
Continued from A Major Milestone For Me Part A 2015 10 12
A long time in the making or I just forgot about a Blog entry completed and saved, but not published so long ago.

More background info:

I was a late bloomer, started later than most, if not all.  I didn’t dream about this all my life.  I found out about CDing accidentally.  I do this for fun.  I am happily married and told my SO about it before I started.  I keep no secrets from her.  I had it easy compared to most.

As I said, I was looking for a place to get glamor photos taken of my wife.  She is the most beautiful and amazing woman in the world to me.  She is not only a feminine wonder but also a pilot, rides motorcycle, races boats, has run a successful business, and since working for a company, makes them 2.5Million$ per year.  Smart, kind, faithful, beautiful, sexy, everything to me.  But to her, she sees flaws where there aren’t any.  So anyway I thought I she should get pictures to see how I see her.

I found a place.  Holland Photo Studios.  And Holland is just a short drive west of Grand Rapids.  The photos were AMAZING!  The poses, wardrobe, makeup, set, everything fabulous.  And the women were regular women, not models, who looked FANTASTIC!  So I thought a great find for her.  They have videos of the photoshoots.  I clicked on one…………………………………………………………………………………..…………………..


I couldn’t believe it!!!!!  THEY WERE GUYS!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

??And it looked like FUN!!!!!!!!!??????????????????!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Where did THAT come from????  I NEVER ever thought about crossdressing!????!!!!!!!!!!!!!!!!!?????!!!!!

I showed my wife and told her that it looked like fun.  The usual feminine look of “nutty man”.  And it ended right there.  WHY?

BECAUSE Holland Photo Studios was in Holland, Rotterdam, THE NETHERLANDS!  NOT Holland, Michigan.  It would have cost me $6000.00!!!!!  That is NOT being financially responsible.  I found that they called it a “transformation”.  I had not heard of this before so I Googled it and found that there are services like this, to one extent or another, scattered all over the civilized world.   And then gave up on the idea as too costly.  The nearest was quite a ways away, at least one that looked equally professional, TG Miss in Racine, Wisconsin.  (I eventually ended up going there and had the time of my life! But that’s another story.)

I travel for work.  There was a transformation service in one of the towns I regularly travel to.  About a month later I was in that town for work, the job finished early, my flight wasn’t out for two days, the rental car, hotel, meals, and flight were paid for.  And I would be getting paid while having the transformation.  I had not preplanned this.  I called them and asked if I could stop in and check them out for a future trip.  The response was kinda offputting.  “We don’t do walkins, but if you want to stop in and just check us out, then OK.  But I won’t be able to spend any time with you because I have a gal coming in for a transformation.”  So I mentally wrote that off.

An hour later they called and said that the scheduled transformation had cancelled.  Would I like to come in for a transformation?  OMG!  I was NOT NOTNOT that far yet.  But what the heck, it was never going to be cheaper.  So I went for it.  That day.Right then.Unplanned, sort of accidental.

She was busy arranging an event for the next evening, we got started late, she was able to do only one of the three makeup styles and one of the three outfits.  So she suggested we resume the next morning.  And so we did.  Then she let me spend the day trying on clothes!  She had a room the size of a two car garage full of clothes and I got to try on as many as I wanted!!!!

Mid afternoon she asked me what I was doing that evening, I had no plans.  So she suggested I join them for the event, an OUTing.

WHAT?!!!???  OMG!!!  I was NOT anywhere near that page yet.  But what the h311?Paid for so it would never be cheaper.  So she got me ready, loaded me in the minivan, and off we went!!!!  We went OUT right down main street.  I was in the whole kit.  Right through all the people, in to a club, and dancing.  As part of an entourage of six.For me a comforting perimeter.


Less than 24 hours after my first ever dressing, I was OUT enfemme in the general public.

This set the pattern for my CDing thereafter.  I always go OUT, don’t know anything to do with CDing other than dolling myself up and going OUT, like out walking around, the mall, restaurants, EVERYTHING.  And it just seems right.

I have always gone OUT.

Our Group routinely takes new gals for their first time OUT enfemme.  Find someone or a Group to help you.  In the right city and with the right people going to the right places, you will at first feel EXPOSED, VULNERABLE, SCARED, and then in an hour or so you will just feel like it is the most natural thing.  And exposed, vulnerable, nervous, happy.

I go OUT enfemme regularly.  I take three or four outfits and change every few hours during the day.  Last time I was OUT I tried on a few blazers right next to the racks in a few of the stores.  Tried on dresses, skirts, suits in the dressing rooms.  I found some GREAT buys!

This is SUCH FUN!

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Published by

Billie Anne Jean

I am just having FUN!