A Trans-Generational Transgender Story

After a long period Mary contacts Linda to tell a story and seek some advice. The story starts now. The advice can wait.

What a pleasure it was to hear from Mary. I don’t hear from Mary very frequently, not every week, every month or even every year. So when I get a message suggesting we have a Skype session I know something big must be up. Either she had something big to tell me or to ask me. As you will see it turned out to be a whole lot of both.

Mary is the person, a lifelong crossdresser who lost her wife to terminal illness shortly before both of them were to retire to Florida. Having been out to her wife but to no one else among family and friends, Mary felt her loss even more strongly than a husband feels for the loss of his wife. It was a two-fold loss.

Eventually with support from friends and counseling from her church she came to accept that life goes on. After a lot of soul-searching Mary went ahead with their retirement plan but with one change. When she snow-birded down to her new community she went all in. she decided to live full time as a woman No one would ever know she had a male side to her life. She had always been considered pretty passable and she pulled it off. “Besides it is nobody else’s business what I have between my legs,” she used to tell me.

The one complication was that when members of her family wanted to come to visit her in Florida they would expect to see her male side. They knew no other. She developed the practice of renting condos in the Orlando area when guests were coming. They were happy with that. They were happy with the explanation that her place was too small and the community was not a good one for the kids. Those were both true. They suspected that dad might have a girlfriend he was concerned about introducing to his kids. They never suspected he was the ‘girlfriend’.

Things started to change for Mary when one of her grandsons came to visit. The seventeen-year-old revealed his CD urges. Mary, the male version of Mary, proved to be surprisingly sympathetic and ‘managed to find’ a makeover service to allow the boy to explore himself. Male Mary even arranged for them to visit a nightclub she had ‘heard about’. It was called Parliament House.

That was several years ago. Life went on. Mary went back to being Mary and her grandson moved on first to college and then to the regular work force. They never talked about those days in Orlando. As far as Mary knew his experience in drag might have been a one-of.

That is they never did talk about it until Jason called out of the blue and asked about coming for a visit. They talked for a while. They agreed on a date. Jason hesitated a bit and then asked, “Is it okay if ‘Jazzy’ comes along?” Jazzy was the name the young CD had chosen for herself.

“You mean ‘Janie’?” replied Mary, referring to the name she claimed she had suggested for her.

No matter. They settled on a date that Mary would pick up Jason in Orlando. They would stay one night at a hotel in Orlando so Jazzy could ‘come out’. “If you are going to live at my place as a woman you are going to have to do it 24/7,” Mary had told Jason, “Can you do it? There is no backing out. I have a reputation to uphold.”

At this point the young man had no idea he was going to meet the female side of his grandfather’s character. OOPS, did I spoil the surprise? I don’t think so. You experienced readers of transgender literature will know what is coming. Or do you?

When the big week came, Mary rented a suite in a seen-better-days resort in Kissimmee, just south of Orlando. She spent most of an afternoon getting off her make –up, taking the polish off her fingernails and generally ‘butching’ up her look. It had been months since she had been in drab, she thought to herself. But it was worth it to see her favorite grandson and to help his progress toward passable femininity or was it going to be full womanhood, she wondered.

Jason’s flight was on-time. After a brief greeting—fist pump and a hug—the two were off to the baggage carousel where Mary was not surprised that the lad, now a young man, had come loaded with luggage. ‘Been there; done that,’ she thought to herself. She could not help but notice that Jason’s hair had grown long. He had it neatly tied back in a man bun.

During the drive to the hotel the two talked about family and about each other. Mary learned that Jason and his latest girlfriend had just split up. “We had some compatibility issues,” said Jason, “she couldn’t accept the person I was becoming.” He left it at that.

Mary didn’t pry deeper. She didn’t have to. Many a crossdresser, transsexual and transvestite have been down the same road. Some many times.

To slip in a nautical metaphor Mary learned that Jason was now sailing alone with time and space to explore uncharted waters. As grandpa had been so helpful the last time they were together Jason hoped that he would be a friendly observer and ship’s pilot on this new journey of discovery.

(Girls! He didn’t know the half of it! But he was soon going to find out.)

Fast forward to the hotel. Jason knew they were going to be stopping at a hotel. Grandpa after all wanted him to be Jazzy all the time at his place and no time like the present to start. But why the two-bedroom suite, each with its own bathroom and a kitchen that had been stocked with some beer, a bottle of wine and light snacks?

“You take the bags you need and get changed in that room,” grandpa said, “I’m going to read, get cleaned up and rest a bit in the other. I’ll close the door. We’ll probably be staying here overnight so grab yourself a beer if you want one.

“Thanks grandpa” said Jason little knowing that would be almost the last time he would be calling anyone ‘grandpa’.

As Mary was telling me this I was thinking how neat it would be to see it as a Broadway play. Perhaps Neil Simon would have written it to have a darkened stage except for two lighted rooms, one at each side of the stage. In each room would be a character, one much older than the other but each going through the same MTF transformation ritual, applying foundation, then makeup, putting on bra and padding, adding a padded panty, both deciding to wear a blouse and skirt, one’s quite a bit shorter than the other. Perhaps there would be a house band playing some gentle music before subtly slipping into playing something like I Enjoy Being a Girl for Mary or Man, I Feel Like a Woman for Jazzy.

Jason rather expertly brushed out his long hair and applied a bit of spray. Mary picked her favorite short gray wig. Each checked herself continuously in their mirrors. They are crossdressers after all and that’s what crossdressers do. If it were a Broadway play the director would have it timed so that the two, still independent of each other, were applying their jewelry in sequence with each other so to the audience it looked like the ritualistic performance it often is.

But this was real life. Mary was out of her bedroom, sitting on a couch/ sofa, casually sipping on her beer and reading a magazine when Jazzy made her appearance.

Mary knew what was coming—or at least she thought she did. For Jazzy seeing Mary was a total surprise.

“Grandpa, you didn’t have to do that for me!” exclaimed Jazzy.

“Jazzy, you are so beautiful,” exclaimed Mary. “You have been practicing! But this look isn’t just for you. Bring your beer and come sit down. I have a lot to tell you.” She patted the couch beside her but really she wanted the girl to sit opposite so she could admire her beauty. With her hair styled, her eyes sparkling, her lips a beautiful dark shade of red and just enough cleavage revealed it was obvious that Jazzy had gone from Crossdressing 101 to graduate school in only a few short years.

Mary told me that the old joke flitted through her mind: incest is okay so long as you keep it in the family. But seriously she determined right away to not get involved with this delicious young thing. I guess we can change our outward appearance but somewhere deep inside a bit of that male mentality may still be there.

Jazzy got her beer and sat down, not next to Mary but in the chair at the corner. It seems Jazzy wanted to look at Mary as much as Mary wanted to be looking at Jazzy.

“I’m so glad that you are not all, ‘you can’t do this; you are my grandpa.” Mary told Jazzy.

“Well I am shocked and surprised,” the younger gal replied, “however, once the initial shock wore off I see you are pretty cute and that is no amateur make-up job. But isn’t that skirt a little short for a woman of your age?”

“A woman of my age!” shot back Mary, “I’ll have you know that I am not a woman of my age. My femme identity is at least 15 years younger than your grandpa. Remember also that my name is Mary and you are not my granddaughter. You are my niece Linda, I mean Jazzy,” she smiled. “But yes the skirt is a little short. I’ll change into something more suitable for us to go out for a bite to eat. You must be starved. I’ll save this skirt for my next time at Walmart.” They both laughed.

“My gosh! Look at the time!” I said to myself, “I have to get this article to Angela. I’ll tell the rest of Mary’s story next month.”

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Tags: crossdressing, featured

Category: crossdressing