What is the Right Approach for You?

A big event in many crossdressers’ lives is the venture out of the closet and in to a ‘mainstream’ location such as a major shopping mall. Surely few are going to pass in front of everyone’s eyes. So what is the right approach? Linda has always ascribed to the idea of toning down and try to blend in. Recently she spent the day with Lisa, a t-girl who makes no attempt to blend in to the crowd. Lisa seems to flaunt her difference. ‘Vive la différénce,’ as they say in France. It gave Linda pause to think ‘what is the right approach?’

Crossdressing generally starts as a private and ‘closeted’ activity. Eventually many crossdressers want to spread their wings to find fulfillment beyond the closet. Some seek out and join support groups. Some go further and seek enjoyment in going to so-called — t-friendly nightclubs and social groups. Some like to get even more fully out of the closet and partake in typically ‘straight’ activities such as going to theatre, to restaurants and to the mall. That brings me to my question of the month: What is the right thing for us to do when we go in to the straight world? Blend to fit in or flaunt the difference?

I must admit to being a ‘blender.’ However recently I met up with a ‘flaunter.’ We spent a day together in Ocala, Florida going to church, to lunch in an Applebee’s Restaurant and to a mall. We were a study in contrast. However, my friend Lisa, the ‘flaunter’ gave me a lot to think about.

I first came to know Lisa through an ad she placed on CraigsList.com. The website is one of the largest and most popular classified ad websites on the Internet. I use it a lot to sell and buy sports equipment and general services. I also use it as a dating site when, as Linda, I want to find companionship during my travels.

This particular trip I was going to be in Ocala, Florida. Following my practice I drafted an ad to announce my availability. Then I looked over the M4T and T4M ads to see what the locals were saying. That is where I came across Lisa. She was a T looking for M. Her ad was the epitome of truth in advertising.

Those of you who are familiar with Craig’s List will know that a lot of the ads in the Casual Encounters and Miscellaneous Romance sections are pretty cruddy. Most are poorly written and contain bad photos with heads cut off or obliterated. Hers was different. She had some nice photos showing her seated, wearing a nice short skirt. It read:

I am a cute, sexy, bi-sexual TS/TG. I am 62 yrs young and I want to find my soul mate. I want a nice person who is looking for a TS like me to be their lover, french maid and bedroom whore. I am single, clean, DDF and want to meet a person who is the same. I like dating but…. I am not looking for hook ups or one night stands. If you want to get to know me and you are looking for the same type of relationship or would like to ask me out for dinner and/or drinks email me with “I am the one for you” in the subject line so I know you are real. I am willing to relocate for the right person.

The photos were taken from an angle above her head which shows she knows what she is doing with a camera. There were no deer-in-the-headlight shots for her, no shots bringing unwanted attention to her neck or belly. She also smiled a big smile. I had to shake my head at her age. The photos suggested no such age and my experience is that any girl admitting to an age over 50 was really draining a lot of water out of the dating pool. A lady friend of mine had once said that all women seem to have a ‘Best before 45’ label tattooed on their forehead.

I think you’ll agree that Lisa set fairly high criteria for the man she was seeking but admitted to enjoying going to great lengths to please him. I thought except for the age and the French maid part that’s the ad I should be placing. I wrote to Lisa to tell her I enjoyed her ad. That started an exchange of messages as we got to know each other better.

Lisa turned out to be Lisa Snow originally from the Chicago area and now relocated to Florida to enjoy her approaching retirement in warmer weather. We discovered our parallel lives, starting from our early childhood experiences through the erotic teen years to the denial years of our 20s to rediscovery as our years and travel opportunities advanced. I got the impression that she enjoyed male companionship and intimacy the same way I did, not so much to satisfy a craving for penis but more for the internal sense of validation that a male’s arousal gave us.

I was due to have a pretty full weekend in Ocala but we agreed to meet on Sunday to attend her church and then go to lunch. A male admirer would be joining us for lunch.

I chose my outfit for the day very carefully. I wanted to be a bit dressy for church but modest enough for lunch at Applebee’s and down enough for a trip through the mall if that is where the afternoon took us. Can I still give the admirer a flash of cleavage? Why not? I decided on a plain brown below the knee length skirt, a solid black V-neck blouse and (ugh) flat shoes. At almost six feet tall I knew I could not expose even more height. I chose modest earrings and a simple necklace to compliment the clothes.

I arrived before Lisa at her church, a Metropolitan Community Church and waited outside. She arrived soon after. We said hello and headed inside. Lisa was wearing essentially the same style of outfit she was wearing in her photos — a very short flared miniskirt, a jacket and quite high heels. ‘Okay,’ I thought, ‘this will not be too out of line at a MCC. They accept everybody. What about lunch and the mall? She may really turn on the admirer but she will certainly bring a lot of attention.’

As I expected Lisa and I were very well accepted at the church. She was new to the area and so new to the church but she had already made a lot of friends in the small congregation.

About noon we made our way to Applebee’s where we met up with George. He was as charming as expected, a great host and in ways he had a life also parallel to Lisa. At least both had recently moved from northern climes to the Ocala area. When we were seated we weren’t drawing any particular attention to ourselves but I could see that as Lisa made her two trips to the ladies room a lot of heads were turning. For some reason tall girls in high heels and lacy miniskirts draw a lot of attention in an Applebee’s on a Sunday afternoon. On her returns Lisa did not seem at all fazed by the attention she had garnered.

Our lunch ended. Lisa and I thanked George for his generosity and made our way to the nearby Paddock Mall. I had an idea that I could convince Lisa to buy some outfits that were, in my view, more body appropriate and situation appropriate. It is safe to say that Lisa was the only person in the mall wearing high heels and a lace miniskirt. There may have been a tiny young tween somewhere in the mall wearing a similar outfit but we didn’t see her. I had the idea to show her a dress or skirt and blouse outfit with more length and an empire or princess waistline to de-emphasize the waistline would be a great change.

“How about this?” I asked while holding up a nice summery dress.

“Not my style,” came the response.

“Or this?”

“No.”

We quickly came to an impasse as Lisa made it clear that she was only interested in wearing the ‘sexy’ style of clothing she had on even if that meant drawing a lot of attention to herself.

“Look, I’m tall and I’m big,” she said, “I’m going to be noticed whatever I wear so I might as well wear the clothing that I enjoy.”

I couldn’t argue with that. So we walked through the mall. It had been a long time since I had felt so much attention coming my way. Lisa proved to be a great model for this new role of attention getter. She kept looking straight ahead, not shirking and not making or avoiding eye contact. ‘I am what I am. I  — we — belong here. Get over it!’ That pretty well summed up what seemed to be her attitude. “My God! Let’s get out of here,” was my unspoken attitude.

Neither of us had a lot of money to spend so we did retreat from the mall. We went next door to the largest Goodwill Store I’ve ever seen. There we were more in our respective elements. Lisa found plenty of her style of skirt that other women had discarded; shoes as well. I found lots of dresses and skirts in more subdued styles and colors. At Goodwill there is usually something for everyone.

The only problem with Goodwill was that they didn’t have a lot of try-on rooms and those they had were impossibly small for me and probably for all the other plus size women who seem to frequent this chain.

In the end Lisa and I parted, she to her home and I to my hotel. We have kept in touch only a little since that time. But I have thought of that Sunday a lot. I started the day convinced I could introduce Lisa to some new styles. I ended up learning a new sense of freedom and empowerment from her: “I am what I am. Get over it!”

Tags: crossdressing, featured, passing

Category: Transgender Body & Soul, Transgender Opinion