Mary and Jazzy Have a Talk

This story started about five years ago.

Mary, a lifelong crossdressing snowbird, lives six months of the year full time en femme in a 55+ deed restricted fun loving community in Florida. When family are coming to visit she rents a place in the Orlando area, ‘goes butch’ for a while and everyone has a good time.

Then one time Mary’s visiting grandson, Jason, comes out to his grandfather that he thinks he is trans and could grandpa help him explore. You would think that a teenager coming out to his grandfather that he wished to explore and experiment with his interest in crossdressing would be a story filled with conflict and confusion. It wasn’t. Mary masquerading as her male self arranged for Jazzy — still known then as Jason –- to have a makeover, to buy some wardrobe and to enjoy an evening at a popular Orlando gay resort called Parliament House. Then Jason packed up and went home. The young lad and his grandfather saw each other frequently over the next five years but never talked about the ‘Jazzy week’. Was that a ‘one-of’, Mary often thought but she never asked.

Skip to present. Out of the blue Jason wants to make a return visit to grandpa and tells him via email that he wants to visit as ‘Jazzy’, his chosen femme name. Mary says okay but it must be Jazzy 24/7. Then she decides to arrange for Jazzy to stay with her in her retirement community. But you guessed it. If she is going to do that Mary must be planning to come out to Jazzy, something she had never done with anyone in her family except of course her late wife. It’s a big step for Jazzy and a bigger step for Mary. Mary fretted for weeks over how her Jazzy might react to meeting Mary.

The time finally arrives. Mary goes butch and picks up Jason at the Orlando airport. They go to a rented apartment where Jason can properly transform to Jazzy. You all read that a few weeks ago, eh? It took Jason/Jazzy about half an hour to do the transformation, not bad time, really. Mary was ready for her.

As Jazzy stepped out of her room she was wearing a knee-length pink pencil skirt, white blouse and cream colored 1 inch heels. Her honey blonde hair had been brushed out and then pulled back into a ponytail tied high on her head. She expected to see her grandfather in his customary golf shirt and shorts but instead was greeted by Mary wearing a Carolina blue sheath dress with a starburst waist by Ivanka Trump ($21.95 at Ross Dress for Less), black flats, necklace and earrings ($4.95 each from the Treasure collection at Goodwill). Her grey wig was also pulled back and held by a hair clip.

“Grandpa, you didn’t have to do that for me!” exclaimed Jazzy. “I appreciate the gesture, but I know you accept me as I am.”

“Let’s each grab a beer and sit down,” replied Mary. “ There is so much I want to tell you.” As any crossdresser knows it is a really big deal to come out to anyone, particularly to anyone in the family. The path goes only in one direction. There is never any walking it back. Once out you do not fit back in the closet.

Mary had weighed the consequences. She knew Jazzy would be t-friendly but would she be friendly to a t-grandpa? Kids, even ones now in their 20’s, hold some strong ideals about their parents and grandparents. Mary’s mind was quickly put at ease on that score.

 “Grandpa you don’t have to do that for me,” repeated Jazzy. “Wow, you look good for a gal of your age.”

Mary replied, “I’m not a gal of my age and I’m not your grandpa at least not for the rest of the time you are here. I am your Aunt Mary, you are my niece and don’t you forget it! Come sit down. Here is that beer. We are going to have a talk.”

So it was that for the first time in many years Mary laid out her life story for another to hear. In some ways the story was similar to Jazzy’s. There was a curiosity, an experimental try-on, a feeling of arousal, a release. Then you know how it goes: more experimental try-ons, more stimuli and the same response. Pavlov’s dogs could not have done it better themselves and soon just the thought of putting on women’s clothing was enough to be that stimulus. I guess we would call it ‘arousal’.

Of course, you know the drill as the years pass. For Mary the need to dress and go out gets stronger. She wants to keep her ‘Mary’ life secret from others to save possible embarrassment for herself and her family. That went on for many years and would have continued to her dying days if Jason had not come out to her as Jazzy.

Neither Mary nor Jazzy felt she should have been born a female, that her body didn’t match her mind. If you asked them probably both would have said, ‘I just like the way I feel and I want to feel the way I like.’

Years ago when Jazzy was created Mary had wanted to tell Jazzy her story but just didn’t know how to do it. Then came the unexpected visit. It was time to tell she decided.

What do two t-gals from the same family but separated by two generations talk about when they meet for the first time?

According to Mary it was pretty well everything. Mary wanted Jazzy to tell her what had been going on in her life for the last five years. Jazzy wanted Mary to tell her life story over the last . . . well let’s just say the last few decades.

Mary was surprised at how good it felt to unload her story to Jazzy. It was like a tremendous burden being lifted from her shoulders, she told me. Mary had not had a close confidante since the passing of her wife. Now she felt she was gaining one in Jazzy. Needless to say, there were some personal memories that the older could not tell the younger. Mary got the feeling that Jazzy, too, might be holding back.

Mary was glad that her initial lessons had paid off well. Jazzy was attractive and very passable. They were supposed to be going out to dinner but one beer led to another and soon Mary was suggesting getting in touch with Uber Eats. ‘Let me get it,’ said Jazzy as she quickly and expertly ordered an array of Chinese foods which was fine with Mary.

The two continued their conversation. When the food order arrived, the driver seemed none the wiser that he wasn’t delivering to two attractive ladies. He even made a bit of a pass at Jazzy. She dismissed him with a smile. Mary noticed the attraction Jazzy had generated. She would ask Jazzy about it later.

The two t-girls/grandpa and grandson aunt and niece — take your pick — quickly arranged the table, set out the food dishes and settled into a bit of an overdue meal. That did not break their conversation. They had so much catching up and learning about each other to do.

They continued talking through the dinner and the bottle of wine that went with it. They talked more over after dinner drinks. Not every subject revolved around transgender issues. They both have interests in flying and sailing as well as photography and years ago Mary had passed on her stamp collection to a keen young Jason. “It is there but probably hasn’t been touched in five or six years,” Jazzy reported.

Mary was starting to feel a little ‘liberated’ and she was sure Jazzy was, too. The conversation did return to the TG world when one of them wondered if anyone else in the family was TG. The most likely candidate, they decided, was a cousin named Timothy, not Tim — “Timothy”.   He was everyone’s first choice when the question was asked ‘what guy in the family would make the prettiest woman?’ A second candidate for likely TG was Timothy’s sister Rachel, they agreed. Taller and huskier than Timothy she favored jeans and tees with feminist slogans over skirts and dresses and she was the only one in the family to play a sport called rugby.

“Can I ask you a personal question?” Jazzy asked Mary.

“Yes, you MAY.”

“Sorry, MAY I ask,” Jazzy said and then paused . . . “Has a man ever hit on you?”

Mary was a bit taken aback. She did not expect things to get so personal so quickly and she did not want to go into those details of her life. However, a lifetime of experience had told her that when people ask such a personal question it is often because of something in their own lives they want to discuss. She turned the question back. “What a question to ask an old gal. Why? Have you been hit on?”

“You know I have. It happened the first time we were out years ago and you saw that Uber driver. He would have gladly taken his payment in trade.”

“I thought he was just buttering you up for a bigger tip but as far as being hit on yes it comes with the territory when you are a t-girl out on the town. So many guys will just assume we are real sluts, that we are after only one thing. Does it bother you? You do have control. When you say no it means no.”

“I know that and I have never had someone come on stronger than I wanted. Sometimes I liked the attention and sometimes I get a real charge out of pleasing a man.”

“Really?” asked Mary with a bit of surprise.

“Really. I hoped you would know what is going on. I’ll meet a cute guy. He looks and acts straight but he wants to go to bed with me. If everything is right I’ll agree and we make out. It’s not that I’m turned on by him or his equipment, but I enjoy the idea that I am feminine enough to turn on this otherwise straight guy. It is empowering.”

Mary paused in her telling of the story. “That’s exactly what you say, don’t you Linda?”

“I guess I do,” I replied, “so what did you tell her?”

“I didn’t tell her anything. I continued to ask and support her. She told me that she was a bit confused about her sexuality because she enjoyed pleasing men but didn’t feel any need for those men to please her. She said she often felt like faking an orgasm. I told her she had reached the highest level of womanhood,” Mary laughed as she told me.

Mary also said Jazzy reported no trouble taking up sexual relations with her girlfriend after a night out on the town.

“I bet she found that strange,” I commented to Mary.

“She says she did at first find it strange to be going out and hooking up with a man one night and being with a girlfriend the next.” responded Mary.

‘One mind, one body: two worlds,’ I commented.

They talked longer into the night before Jazzy asked Mary one more question. “what makes an admirer admire us,” asked Jazzy. “They often have wives and girlfriends. What is it in us that turns them on?”

“I don’t really know,” answered Mary, “but I’m sure my friend Linda will know. I’ll ask her.” And that is what she did.

My answer: I don’t know for sure but I’ll try to find out. THIS IS WHERE YOU COME IN. DEAR READERS. DO YOU HAVE ANY INSIGHTS ABOUT WHAT MAKES AN ADMIRER ADMIRE? Please share them with me. I have set up a special email address. Write me with your thoughts. Are you an admirer who likes t-gals? Tell me why? Are you a t-girl who has gained some insight along the way? Tell me. All is as confidential as you want it to be. Write me at lindajen@hotmail.com. Put Admirers in the subject line. I’ll bring together the results and report to all.

Thank you for reading.

Tags: crossdressing, featured

Category: crossdressing, Transgender Fun & Entertainment