Linda’s Wonderful Week

I call them my “Wonderful Weeks.” I recently spend one in the Berkshire Mountains area of Massachusetts.

What is a wonderful week and how did they come to be?

For a crossdresser I’ll admit that I have a pretty enviable situation. Since a few months after we first met my now wife has known about my penchant for crossdressing. She has met Linda, She has gone to the theatre, golfing, shopping and many other activities with my femme self. She was a bit shocked when she learned that the costume I was wearing for that Halloween party was an important part of my identity that extended way beyond the bounds of Halloween. Luckily for me she accepted Linda as part of the person she had come to love. She even absorbed and accepted that it was an important part of my femme identity that as Linda I enjoyed the company of men and the validation I got when my sex appeal led to a man’s arousal.

As the years have passed we both have come to common realizations. She prefers my male mode for company and I feel somewhat constrained in trying to be Linda when I am with her. No matter how femme I might be dressed I found it difficult to not hold a door or a chair for her. When talking to others I am told I do a pretty fair job of feminizing my voice. However when talking with my wife no matter how pretty I look and feel my reflex is taking my voice into a deeper male baritone. It is/was disconcerting.

So we have come to an arrangement. From time to time I will take an afternoon or evening and go to a nearby city where I can dress as Linda, go out with friends and generally let off some steam. She worries a bit and always her parting words are “be careful.” Mine are “I love you.” We don’t ever talk about it but I’m pretty sure that her be careful means two things -– don’t get caught and practice safe sex.

However there is more. From time to time I will go on a solo vacation –- usually about a week at a time. During this vacation time I become Linda every day, all day.

Except for having to occasionally run a razor across my face I am en femme for everything I do. That is why I call them my “Wonderful Weeks.” Once I used the week to attend a Southern Comfort Conference in Ft. Lauderdale. However usually you will find me looking for a resort sometime during its low season but not during its snow season. Past vacations have seen me in the Poconos and Provincetown in May, Vancouver and Whistler in September, and Quebec City in October.

Picking off-season I am able to get some pretty good suites and very reasonable prices. Yes, suites. I insist on being able to cook my own meals. It is not that I am afraid for Linda to be in the hotel restaurant. I just prefer my own meals. I also really enjoy the experience of going through the local grocery store, peeking around to see if anyone is looking back at me, bending over to pick up a soup can on the lower shelf, knowing that my cleavage will get a little extra exposure. After dinner I like to hang around the resort lounge although that is not a great hunting ground as the resorts I favor cater mostly to families and couples without many singles around.

However a vacation alone can be pretty lonely so I usually look for company through a web service such as Craig’s List or occasionally FetLife.

OUCH! Girls, I can feels your sneers from here. How can I lower myself to use a low-brow dating service such as Craig’s List? We’ve all seen the ads of some guy with a fat hairy belly wearing bulging panties, garter belt and stockings with all kinds of runs in them. Those are the type of T girls that typify Craig’s List. Well, yes there are a lot of ads like that and I can only imagine what guys are responding to those ads or wonder if they are getting any responses at all. But more about that later.

Having decided to take a “Wonderful Week” in late September I then had to find a place to go. I used an on-line time share catalogue and found a pretty nice place in the point range I had available. Nearby would be woods with lots of hiking trails, golf courses, outlet shopping and a museum or two. The resort offered a large swimming pool, mini-golf, a movie theater and other amenities. The ad showed photos of a large and active night club. ‘Perfect,’ I thought so I booked a week.

Linda in the Berkshires.

Well, if I am going to be going down through the Hudson Valley why don’t I see if my friend Jan would be available for a game of golf, I thought to myself. Jan is a very good golfer and an interesting t-girl to be with. Of course she was up for a game and she invited a third, Lucille, to join us. My week in the Berkshires actually started on a Friday on a golf course in the Bronx. How was that? Well anyone who knows anything about playing golf on a public golf course in the New York City area knows that Jan, Lucille and I had plenty of time to chat. So much time that I had to bail out after the three hours it took to play the front nine. I wanted to get to my resort before dark. I barely made it.

After a stop along the way to refresh my make-up and relieve my bladder I somewhat nervously approached the resort check-in with an explanation of why my outward appearance did not match the name on the reservation or my official identification. The story was not needed. All I needed to say was “I’m Linda Jensen. The reservation is in the name of XXXX XXXXXXXXX and I was the companion ‘Ms. Jensen.’ For the rest of the check-in the clerk referred to me as Ms Jensen. Or was it Miss Jensen? I have some trouble with those New England accents. It had the added advantage that I was not pressed to sign up for presentations to buy more time share weeks, points or whatever they were selling there.

Once in my suite –- and what a wonderful suite it was -– I wasted little time setting up my computer and checking my e-mail. I was pretty sure what would be waiting for me. A few days earlier I had placed an ad on Craig’s List and the responses were coming in at a steady rate. For most I had written back that I was not interested in them as in fairness they had not responded with any understanding of my ad. However there were a couple that grabbed my attention and I was hoping to meet some time during my week.

The ad?

Those of you who peruse the Craig’s List casual encounter ads will notice some unusual things about my ad. My photos included my face and did not include my genitalia: unusual but it gets positive results. Also my suggested encounters were not so casual as to suggest I would settle for a ‘quickie’ or a ‘blow and go.’ The responses were plentiful and quick to come and took a fair bit of time to sort through, separating the trollers and exhibitionists from the genuine admirers

I’m not going to reveal any details about what happened during my dates. I’ll just say that I got to the Rockwell, I had my hike, I got treated to a nice dinner, attended a movie or part of it and generally enjoyed myself with a couple of very nice men.

I had one disappointing experience with a man showing up late, claiming he did not have time for the ‘date’ part of our meeting and generally being a very dull person. I have heard of a lot of born-women who have felt it best to ‘give the man what he wants’ just to get rid of him. I know what it feels like. I’ll just say it helps to be able to detach oneself emotionally from what is happening physically.

But now on to the more important events of the week. Living all my waking time as a woman meant I got to be out and mingle with others while grocery shopping, searching for yet another perfect outfit at a mall, even getting a leaky tire fixed while trying on clothes at the Goodwill store next door. I took advantage of the great weather to sit around the resort pool and I played mini-golf while a mother and children played near me. Did I have total acceptance? Perhaps others at the resort might have been more open to communication with another single woman but generally I was called ma’am when that was appropriate. My Linda credit card was always accepted without a second look. I even had gents stepping aside and holding doors for me.

As my wonderful week wound down it occurred to me that I have come a long way since the first hot, humid summer evening when I as Linda first ventured out on the streets of New York City, sweating as much from fear as from the humidity. I have come a long way but so has the society around me.

Thank you to everyone from the Stonewall drag queens to the transgender activists to movies like ‘To Wong Foo…..” to Jazz Jennings and yes even to Caitlin Jenner. So many have done so much to normalize our existence. I hope that when someone sees and reads me they will then be more comfortable and a little less threatened when they realize ‘that chick is a dude.’

Tags: crossdressing, featured, Out & About, passing

Category: Out & About, Transgender Body & Soul