I have kept from sharing too much of my story because I have been trying to maintain a degree of anonymity and am completely aware of how revealing anything on the internet can easily lead back to you and very easily unintentionally out you to ... well ... anyone paying attention or seeking information about you.
Now, I am not really out to anyone except my wife and it is in deference to her that I have stayed in the closet, as it were. Not being more open and honest about this aspect of my life long ago is perhaps one of the very few regrets in my life and things I would likely change if given the opportunity.
That being said, given the current circumstances, I find it necessary to share a little about myself because I am in some serious need of some advice/encouragement/assistance from you fine ladies (both GGs and CDs alike).
Like many here that have shared, my crossdressing started during my adolescence. I tried on a pair of my mother's pantyhose that were drying hanging over the shower door and found them to be sensual in a way I never expected. From there I tried on, in secret, other pieces of clothing in my mother's and sister's wardrobes and found the experience wholly engulfing.
When I went off to college, I expanded my wardrobe from the few items I had nicked from my mother and sister and made a few excursions (mostly walks around campus or drives in the wee hours). My hobby stayed a secret and hidden from everyone I knew, including my college roommates.
After college I lived on my own and my girly things moved with me. Staying mostly in a box in the closet, I occasionally dressed in the privacy of my apartment, but for the few years immediately following college, I never ventured beyond my apartment.
This was in the early days of the internet and information was not as readily available as it is now. At the time I thought I was weird and couldn't figure out what was going on within my head. I knew I wasn't a woman trapped in a man's body. I liked my male parts and had no intention of ever pursuing SRS or going full time. My first full on excursion in public with people that knew me was at Halloween.
My oldest friend in the world had just come out to me as gay and had invited me to a Halloween party a friend of his threw every year. At that time, much like now, the general public conflated crossdressing and gender-bending with sexuality. I wanted to show my friend just how much his being gay made no difference to me in our friendship and I wanted to finally get OUT! So I dressed up and completely surprised my friend. The night was a total success.
I didn't go out again for a few years. Again it was at Halloween. This time with a female friend of mine. She and I swapped genders for the night. This time, my friend did my makeup and it was the first time that I looked in the mirror and didn't see myself, but saw a completely different side of me. We went to her bar where she worked and I sat at the end of the bar drinking wine and chatting with the bartender. It was a safe environment. The staff all knew me and enjoyed my costume. It was a good night. I got hit on by some frat guys from the other end of the bar and some girls I helped that were having car trouble were completely convinced I was just another girl until after I had helped them (one of them said to me, "When I saw you coming outside to help I thought, 'Who is this chick and what does she think she can do that I haven't already done. You look great!'"
That night convinced me that I wanted to go out a lot more! My own internet research on gender identity had convinced me that this aspect of my life may be outside of "normal" but it didn't make me gay and it didn't make me a transsexual. Exactly what I was I wasn't sure, but I knew that I enjoyed the transformation and the escapism of being "her."
Over the next few years, I reached out to others online. I swapped a few emails and met one CD from Ohio while she was in town on business. I met with a small group of transgals for a Gurls Night Out at a bar in a nearby town. It was with them that I decided I didn't much care for going out with other gurls. There is something to be said about safety in numbers, but I felt that it was as much of a detriment as a positive to be out in public with others as far as passing and blending. At 5'10", I am over 6' in heels. On my own, being a tall girl with slightly masculine features (short fat fingers, a small adam's apple, larger feet, straighter hips, etc) might go unnoticed or raise the slightest question, but in a group of five or six others with similar features or even those that just look like a dude in a dress (bless their hearts), well.... it's just the easiest way to get clocked.
So again, I stayed to myself and only went out for late night drives/walks or to the movies.
The year before I met my wife, I went to a Halloween party at another friend's house (not my gay friend from years earlier). My friend and I came up with the idea over drinks the week before (yes, I totally directed that conversation and allowed myself to be convinced to do it). Like the first time, it was a smashing success. I totally passed and floored all of my closest friends at the party. It was an amazing night. I felt so free being out and among my friends dressed. I never wanted it to end.
The next year, my wife and I were dating when Halloween rolled around and we decided to go dressed as the gender bending pimp and ho (again, I let her convince me to do it). We had a lot of fun, but although my wife knew I had done it before, she didn't know how many other Halloweens I had dressed up or how much crossdressing was ingrained in my life.
I never came out to her. We went out for two other Halloweens with me dressed. After the last one I think she knew I enjoyed it maybe a little too much, but neither of us said anything about it.
Everything stayed in the closet for several years after the last time. I had gained a stupid amount of weight and didn't fit in anything I owned and didn't feel comfortable in my own skin in either male or female modes.
Then about two and a half years ago, I had lost a good deal of weight and was getting back in shape. We owned a small store in a fairly rural community. I had the opening shift on Halloween and decided it would be the perfect opportunity to go to "work" dressed. I woke up early, showered, shaved and started getting dressed. I was entirely dressed, makeup done and was doing my nails when my wife came into the bathroom and was horrified by my appearance and what I planned to do.
I thought my marriage was over. My wife was hysterical. It all came out. I told her how I had enjoyed crossdressing for years and that the numerous times we had gone out together on Halloween had been small slices of Heaven for me. I told her I wasn't gay and that this didn't change who I was inside or who the man she had know for ten years. As those of you that have gone through similar experiences know, she was floored. I can't keep a secret (especially from her) to save my life, but somehow I had kept this hidden for ten years. She felt wholly betrayed. It took several tense days for her to come to grips with it.
By coming to grips with it, I mean she didn't leave me or kick me out. She talked to her girlfriend (shared my secret with her girlfriend which I didn't learn until more than a year later) and we talked. We came to the understanding that any dressing I did would be at her direction and with her approval and that it would never be in public.
So that's how we've managed the past few years. It hasn't exactly been a DADT as my dressing has been at home when she wanted it and she has been incorporating it into the bedroom. But she has been hot and cold about it. Periodically resenting my dressing. Often telling me that it makes her feel like less of a woman or that she's not enough woman for me. Those discussions are usually pretty uncomfortable, but necessary. For the most part, it's been there, but we don't talk about it.
In the last year we moved from the rural town we were living in when I was discovered after we lost the store to the economy. Part of why she was so mortified that Halloween morning was that she said she knew the people in the community and that my dressing at the store would have caused her a great deal of discomfort and embarrassment. This last Halloween I suggested dressing up to take our kids trick or treating since we now lived in a larger town and we weren't as integrated in the community. She nixed the idea saying that she thought it would embarrass our boys (none of the children know). I didn't argue, but was a little disappointed.
So next weekend we are leaving the kids with my parents for an overnight visit (my parents occasionally take the kids overnight to give us an extended date night) and my wife suggested that instead of doing the usual things we do on these overnights that we get a hotel room and bring "her" with us. My wife has even suggested we take "her" out in public. She did say that out in public may not be much more than taking a long drive around town because she may not be up to going in anyplace, but she wants to experiment with going out.
And so this is the freak out.
In every instance I went out before, except the first Halloween with my gay friend, I had long hair that I just styled. I have since cut it short and for our playtime at home have used a wig that is in serious need of care before it could be seen in public and passable. My wardrobe is all fairly risque and not really ready for primetime outing. Although my makeup skills are reasonable, I haven't had to do it with the intent of being out in public in years. I am a nervous wreck. I feel like I did before the first time I went out. I worry about passing. I worry about what I'm going to wear. I worry about my wig. I am quite literally freaking out a little.
She said something about us going to buy an outfit for me to wear that night, but I don't know if she wanted to do that this week, or do it that afternoon after we leave the kids with my parents. We haven't really discussed it much, which I know we need to do, but I don't want to rock the boat too much. This is my chance to get out and now I don't know how ready I am to do it.
So.... here's where you all come in.....
What's a Saturday night at the Black Crowne like? I know Friday nights are particularly trans-friendly, but what goes on Saturday nights? Are there any businesses (shopping and restaurants specifically) in the Broomfield/Boulder area where you have had a particularly positive experience dressed? I know most retail shops are reasonably trans-friendly and that as long as one acts like a lady, just about anyplace is "safe" but I'm looking for places that you felt more welcome than others.
I'm considering asking if she would be okay with me going to Ulta or Macy's or someplace similar for a makeover for the night. Any recommendations for places in North Denver/Broomfield/Boulder?
I love my wife dearly and love that she is willing to take this HUGE step and am super terrified of blowing it and/or it being a miserable time. I could really use a few suggestions.
Wow... I really unloaded there. I guess that has all been pent up for a long time. Sorry, ladies. I'm not trying to burden you all with my woes. Feel free to skipping to the last few paragraphs. That's really where the crux of the matter is.
Thanks!