I wrote this one very quickly after watching the evening news and I think it has a different twist. I hope it is as kindly received as my first contribution.
Anne

CHERISHING MARY!
By
Anne Gray

“To love and to cherish,
As long as we both shall live?
I do.”

Life wasn’t fair, in fact sometimes it was downright hard to handle.

Mary and I had been married for just on thirty years and now I was looking at closets full of her clothes wondering what I would do without her.

At fifty-two I was alone because a stupid bastard had decided to drive home from a bar with a load on and T-boned Mary’s car. She never knew what hit her.

My tears had been shed until I thought none were left. The marriage had been productive but not with children; we were both too career orientated agreeing early that kids were not on the agenda. Naturally, that had upset both sets of parents but they were no longer around. After the funeral our circle of friends paid their condolences and went on with their own lives.

Between us Mary and I built a very profitable business but I lost interest without her. The negotiations for selling it had just wrapped up and I signed the contract a week ago. The proceeds, and the very large insurance settlement, meant there was more than enough money to keep me comfortable until I joined her again.

We had done everything together and shared everything. Well except for one thing I had never told my love. Why would I put my marriage in jeopardy for something locked away since she came into my life?

The two of us matched in more ways than one. I was just an inch or so taller except when she wore heels but I didn’t mind that she could look down at me. We were life partners and could give a damn about convention. The love we had was palpable.

After meeting and falling in love at university Mary and I married when we were both twenty-two. On the proverbial shoestring I gradually got a business idea off the ground and a year later Mary took over the selling part while I handled installations.

It got a bit rough at times but then things took off and by the time we were in our thirties Mary and I would arrive at the office each morning holding hands as husband and wife. After seven or eight hours as business partners, she guiding the large sales force and me supervising the crews, we left again the same way.

Early on we decided to fight the stress of developing the business by staying in good shape and joining a health club. One hour each weekday morning was spent there; consequently, even at fifty-two, there had been no middle age spread for either of us and our ideal weight was within a few pounds of each other.

Now, as I fingered the soft fabric of one of her dresses, I wondered how I could live with only memories. I had to keep part of Mary with me or lose my sanity.

Later that week I was again in one of the closets drinking in the oh so familiar scent of my wife. I had just finished a shower and padded, naked, back to the master bedroom to get dressed. I guess the subconscious took over and I found myself surrounded by her clothes.

Without even thinking I lifted one of Mary’s skirts off the rack and stepped into it. After sliding the silk lined tweed up to my waist I closed the back zip and fastened the button.

It was thirty-three years since I had last worn a skirt. That one was badly made and the wrong size, the result of a furtive grab at a thrift store. It looked so ridiculous I ended up purging everything in my collection. A few weeks later I met Mary.

This one was much nicer!

I hung it back up, grabbed my robe, and went down to the living room for a long think about what had just happened.

The experiments with cross dressing in my teens were something I could never really explain. I wasn’t gay but female clothes held some sort of attraction for me and felt right when I wore them. Balancing that was the fear of being found out. I had kept to my bedroom and the thought of going out dressed in public just never entered my head.

In the age before computers it was natural for me to think I was the only one to have such unnatural urges. After throwing out my meager collection, then meeting Mary, life became so busy and full of activity I was able to push that part of me into a tiny pocket in back of my head, there it had stayed, until now.

It was the early hours of the morning before I finally dragged myself up to bed to try and shut down my churning brain.

A few days later I just said the hell with it letting my business experience take over by making a ‘for and against’ list. That led to a ‘what needs to happen’ list and finally, after two weeks of research on the net, a ‘how to do it’ list.

The first item on each list was the same. Was it possible for Michael to pass as female?

Now was the time to find out then either work down the final list or shred them all.

First came a shave, including my sideburns, the rest of my very sparse blonde body hair could wait until after a decision was made. Then a shower before I stood beside our king sized bed where everything was laid out. Having watched Mary get dressed so often I called on those memories rather than the amateur fumblings of three decades ago.

One thing she had never needed to do was hide any equipment between her legs but I solved that problem with a panty girdle I’d found in the bottom of a drawer. Dark pantyhose covered the fact my legs were not shaved and then I picked up the bra.

Feeling a bit like a smart ass I had done up the small hooks and now slipped my arms through the straps pulling it down over my head to settle in place. The old standby, rolled up socks, went in the cups then the silk slip followed the bra down over my head.

After that I pulled on a long sleeved high necked sweater and, since it had started this whole thought process, the tweed skirt. Not only did everything seem to fit but it gave off the lingering scent of Mary. I think, even after dry cleaning, that would remain.

So far so good but I avoided looking in a mirror and would until everything was in place. The tweed jacket of the suit had four buttons down the front that pulled it in to fit around my waist.

The wig was not the colour of Mary’s hair; she had worn it to a company staff party a few years ago. But it was in her pageboy style and I settled it, by feel, on my head.

Using one of her small compact mirrors to apply some lipstick I nearly broke down and stopped to collect myself. I had last tasted that lipstick when I kissed her goodbye for the final time.

I didn’t bother with any other makeup. In the first place I wasn’t sure how to apply it and, in the second place, if everything else didn’t work, it wouldn’t help.

Shoes were a problem because my feet were a bit bigger than Mary’s but I managed to squeeze into a pair of black pumps with a two inch heel.

Now it was what they call the moment of truth.

The image in the full length mirror scared me because, as I turned back and forth looking at it, the female in the mirror matched my actions. True, the skirt was a bit baggy at the back and a pinch tight at the waist but the rest reflected a fifty year old, well dressed woman wearing Mary’s clothes.

I collapsed on the bed and cried. Cried for what I had lost and cried for what I had just found.

Chapter 2 —

A few days later I was flying across the country to San Francisco. As a businessman, after making a decision, I always moved deliberately to attain the desired result. Now I was going to work my way down the ‘how to do it’ list.

After checking in my hotel I phoned to confirm the appointment with the owner of a boutique called ‘Crossroads’. The Internet was an amazing resource and this place was highly recommended among the west coast transgender and transvestite community.

There were equally capable facilities close to home but, with what I had in mind, the fewer local contacts the better.

Clearing my wallet of any identification, I slipped a roll of bills in my pocket then walked the four or five blocks to the meeting with the owner, Gloria. She, or he I never did find out, was close to my age, which made things only slightly less embarrassing despite every effort to put me at ease.

Once in a private office my question was straightforward.

“I want to be able to pass occasionally as a women in my own age range. Can you help me do that and teach me what I need to know to carry it off? I don’t wish to attract attention, in fact, that is the last thing I want. This is to achieve the personal ability to satisfy a very real need.”

Gloria’s reaction was to remind me that I had agreed to pay for a one hour private consultation but, with my permission and at no additional cost, she would like to have one of her staff join us. I agreed and she left for a few moments returning with a man who was easily ten years younger than us.

“This is Tony and he is an expert, among other things, where hair is concerned. Please strip to your underpants and let him examine you.”

Fifteen minutes later he spoke for the first time.

“I would not recommend electrolysis for your beard; it could take at least a year of weekly treatments and I don’t think it necessary to go through that. It is quite light so starting with a close shave and a couple of tips we can provide, there is no reason why you should be concerned for periods over twelve hours or more before it would need attention.”

“Your body hair is no problem at all. Any readily available product, such as Nair, will work well. Just make sure you use a skin soother afterwards to avoid irritation. I must suggest, with respect, that at your age, you do not try shaving anything except your face. I can adjust your current haircut to be completely acceptable for a male yet one that, under a properly fitted wig, will be completely hidden.”

With that he left and Gloria spent the last of the hour not only assuring me I could pass but talking of breast forms, foundation garments and gaffs.

I paid for that hour and booked longer sessions for each of the next three days. That was the ultimate learning experience and I left with a new haircut and a great respect for their professionalism.

I flew home with a suitcase full of supplies, a seriously depleted roll of bills, and a direct e-mail address for Gloria who had agreed to reply to any problems or questions I ran into.

Our house was so full of memories I didn’t have the heart to sell it and yet could not have a female be seen going in and out without drawing unwelcome attention. This would be Michael’s home; my plan called for another and I decided on a condo’ apartment with a private entrance.

First though I had to practice and get comfortable with what had been learned on my trip. That could be done without leaving the house.

Tony had worked a little bit of magic with my eyebrows. Since I wore glasses but my female persona would wear contacts he had shaped them to look natural in either situation. The frame of the glasses covered up the slight feminine curve while I was Michael.

One of the things Gloria had insisted I buy was a pair of properly fitted shoes in my own size; they had two and a half inch heels and I was to begin wearing them immediately around the house. At the start thirty minutes was all I could handle but, gradually, worked up to longer periods without much discomfort.

For the first week or so I never even looked at Mary’s clothes. I wore the shoes and practiced the makeup techniques Gloria had shown me including wearing one of the wigs Tony fitted for me. The first few times I almost gave up because the look was nowhere close to what they achieved at the boutique.

“What am I doing wrong” was the gist of the message I e-mailed to Gloria with a head shot of my latest attempt?

The reply was concise. “Lighten up, you’re being too heavy handed!”

It worked and, with continued practice, I began to like what I saw in the mirror.

All of a sudden the makeup softened my features and blended into itself without leaving harsh contrasts in colour. Even the tiny wrinkles at the corners of my eyes were hardly noticeable. Eyebrow pencil darkened the arched blonde hairs to the same shade as the wig. That, along with a minimal amount of eye shadow and carefully applied lipstick in a muted shade of red, made my face undeniably feminine.

Pulling off the wig I cleaned my face; tomorrow would see the next item on the checklist scratched off. I didn’t need to check, it read:

Full dress rehearsal!

There was only one thought in my head the next day — Mary, please help me.

The body hair was gone without any problems, I had bathed using scented crystals and now, with the gaff and panties in place, was ready to get dressed.

Gloria had supplied and fitted the basic foundation garment. It was a one piece combination long line girdle and bra. There was a minimal amount of padding at the buttocks. I slipped my arms through the shoulder straps and then started to close the front zipper. Taking a deep breath I pulled it up past my waist to the top of the closure between the bra cups.

The tension only took about two inches off my waist but, as Gloria said, with the enhanced measurements around my chest and rear end, that was all that was needed. I popped in the breast forms, settling them in the cups the way I had been shown, then closed the satin flap to hide the zipper with several tiny hook and eye fastenings.

Very carefully I rolled the nylons up my legs and fastened the garters pulling them taut. I had practiced that before but could notice an almost sensual effect now the leg hair had gone. The satin slip literally slid over my head and in place with the bottom hem about four inches above my knees.

At this point I pulled on one of Mary’s silk kimonos and walked over to the dressing table. If this continued I would have to go out in public because I only had the one pair of shoes and not even slippers that fit, except Michael’s.

As I painted my fingernails it amazed me again how feminine such a simple thing made my hands look. When they were dry I worked at it until my makeup gave just the look I wanted then fitted the wig that was in Mary’s colour and combed it in place.

The pale green, long sleeved blouse buttoned in front and had a high collar with ruffles around the neck. More ruffles covered the buttons and were trimmed in dark green piping. The knee length A-line skirt was the same dark green and I tucked in the blouse then fastened the two inch wide belt snugly around my waist.

Slipping into the black pumps I added large button clip-on earrings that matched the skirt. Piercing my ears was not a decision I was ready to make yet. Eventually I might have to make another visit to Gloria for that and advice on how to handle the problem of my voice. Mary’s watch went on my left wrist and I took a hard look at the image in the full length mirror.

True, it was not Mary, but it was definitely a well dressed female who, if I passed her outside would not raise any questions in my mind.

I made a pot of tea and carried the tray though to the home theatre, setting it down on the side table next to Mary’s easy chair.

One of our favorite movies was already loaded and I made myself comfortable in the chair, even remembering to smooth my skirt as I sat down.

Slowly I removed the wedding band from my left hand and moved it over to my right. Mary’s rings slid on in its place. I dimmed the lights and thumbed the start button for the movie.

As the melody of the theme song filled the room I clasped my hands together in my lap so the rings were touching and whispered,

“Stay with me Mary and be part of me. Make it bearable for me - as time goes by!”