Part 4 — Jazzy Has a Date

The saga of Jason coming out to his, unknown to him, crossdressing grandfather has been played out here for s few months. Last month Jason had a makeover and decided his femme name was Jazzy. The story continues with a night out at a local hot spot.

“What is this place?” asked Jazzy as they pulled up to the old style motel with the huge parking lot. She was the passenger while her grandfather drove. They had been staying together in Orlando for the better part of a month but it was safe to say they had never been to this part of town.

Life can bring you some big, fast turns. Several days before a young man named Jason had told his grandfather, Martin, about his sexual obsession with wearing women’s lingerie, an obsession he had picked up after his grandmother had ‘outed’ her ex-husband’s past marital proclivity for lingerie. What Jason hadn’t been told and still didn’t know was that his grandfather had spent the better part of his adult life with a second identity he and all his friends in the TG world knew as Mary. In fact, when in his Florida retirement community, Mary is the identity neighbors recruit for their golf and card games, their talent shows and she is one of the girls most willing to hear their family stories.

But when Martin’s own family plans a visit in Florida he always insists that visit be in the Orlando area as ‘his place is too small,’ ‘young people aren’t allowed to stay’ or ‘you’ll all enjoy Orlando better.’ All of which is true but were outweighed by the desire to shield ‘Mary’ from his family and vice versa.

So it came to pass that when grandson Jason opened up to Martin about his fetish, Martin was very attentive and more sympathetic than perhaps the average American grandfather might be. Jason further confessed to his grandfather that he would like to see what it would be like to take it all the way and dress fully as a woman. Now with a little help from Grandpa and a lot of help from a transformation service called Trading Faces he was Jazzy, looking every bit like a young woman out for a night on the town, wearing a new little black dress, 2” heels, dangly earrings and a splash of perfume.

“Apparently this is the biggest gay club in Orlando with the best drag show in the South. I don’t know but that is what I was told,” fibbed Martin who as Mary was a frequent visitor on Friday and Saturday nights. “We’ll just get a drink, watch the action and maybe catch the first show,” said Martin as he pointed to a sign featuring the club’s Footlight Players.

Jazzy was all eyes, looking around to see the people and to see that they were not necessarily looking back at her. Jason had never been to a gay club but Jazzy immediately felt at ease. It helped that she noticed a few of the regular t-girls. Not by nature a vain person Jazzy still couldn’t help feeling that she compared well to the older girls.

Martin knew the Parliament House complex like the back of his hand but for this evening he would play the visiting tourist. The two toured the piano bar, looked in to the restaurant where they noticed another group of the regular t-girls having dinner. He resisted the temptation to say hello to Leah and the other girls he knew. They walked the patio and pool area and looked in at some of the back rooms serving as boutiques and small bars. Finally they settled in to the Piano Bar. Martin knew this to be a good spot as a set of doors opened directly to the Footlight Theatre where later there would be a drag show. Martin led Jazzy to two empty seats at the bar. “Are these free?” he asked the man seated next to them. Martin had recognized the man but there was no sign of recognition back, just a warm glance aimed toward Jazzy.

The man nodded and welcomed the two, “Hi, my name is Steve.” He gave Jazzy his hand and a big smile. He paid little attention to Martin, “I’m expecting someone but for now you are welcome to join me. I’m sure she’ll enjoy meeting you, too.”

Hi, I’m Marty. This is my friend, Jazzy. We just met outside. This is our first time here.” Martin replied.

Jazzy looked curiously at Martin. “Trust me,” he whispered to her, “for tonight let’s just be friends. Forget that father/daughter stuff.” Martin ordered beers for each of them. Soon the three, with Jazzy seated between Martin and Steve, were deep in conversation. Steve told them he was a visitor from out of town who liked coming to Parliament House for the show and to get to know the ‘special ladies’. Of course Martin knew that because as Mary he had several times been one of Steve’s special girls. For some reason Steve had not made the connection. So tonight they were strangers meeting for the first time and apparently both were ‘admirers’ who would be competing for the attention of the same girl.

Steve proved to be an attentive and considerate new friend. He shared his knowledge of the resort’s history and gave an authoritative account of the lives of the Footlight Players. He did not hesitate to buy a round of drinks for Jazzy and her friend. More than that, he freely shared details of his life in Florida, his work with sales and service of a medical support system. He described how his life on the road gave him plenty of opportunity to seek out what he called the most T-friendly bars in America.

“What are your favorite clubs?” he asked, assuming that Martin was also a well-travelled admirer. Martin could have used Mary’s experience to name a dozen T-friendly hangouts, sadly half of them now closed. Instead he took a different approach, “Listen, I’ve got a confession to make. We are not really here on a date. Jazzy is my granddaughter. She wanted to experience a walk on the wild side, as the old song goes, so here we are. I’m her protector.”

Jazzy blushed at her grandfather’s confession but also felt proud that he had so easily and naturally used ‘she’ instead of ‘he’ and Steve had so naturally seemed to accept that was the correct pronoun. As the three continued to chat Martin noticed Steve was turning more of his attention to Jazzy. Jazzy noticed it too but did not seem too uncomfortable with the attention.

In time, nature began to call. Jazzy excused herself to visit the ‘little boys’ room’. “Not tonight, dear,” Martin corrected her, “tonight you use the other door” and whispering in her ear “and be sure you sit.”

Jazzy smiled and patted her grandfather on the shoulder, “I’ll be right back.”

The two men sat quietly for a while. Then Steve broke the silence, “you know when I first saw you I thought you were just two tourists here for the show. No offence but I thought she might be your young trophy bride or maybe your escort. I shouldn’t be saying this to a grandfather but she is hot.”

Martin had to check himself from telling Steve he knew for a fact that Steve hit on all the visiting t-girls like that. Instead he played along, “you know that she’s a he,” Martin said quietly.

“Well after you had explained your relationship I had begun to have my suspicions but I wasn’t sure,” Steve replied. “I’ve never met a TG here with her grandfather. Usually their family don’t even know they exist. I think it is so great that you are here for her. How did that happen?”

“It’s a long story but in truth Jazzy is not even sure about the TG thing. She is really just trying this out. Today is her first day ever wearing a full feminine identity. Go easy on her. I don’t want to see her scared back in to the closet if being a girl is what she really wants to be.”

“You can count on me.”

Martin knew that to be true. As Mary he knew Steve to be one of the truly nice guys in the admirer crowd. He got it that each girl had her personal limits. He was known to be good in bed but also seemed to be very good about making a girl, any girl, feel good about herself. ‘I’m glad I texted Steve to tell him Mary would probably be here tonight,’ he thought to himself. ‘He’s just the kind of man Jazzy should meet. And I’m sure that after a few more minutes with Jazzy he’ll forget all about Mary’.

Jazzy returned, smiling and wearing a fresh coat of lipstick. Martin noticed that she had also refreshed her perfume. ‘I love that Georgio,’ thought Martin, ‘I’m going to have to arrange for her to leave it behind’.

In time the three made their way in to the Footlight Theater for the first show. Martin and Steve proved to be generous tippers. Martin would give Jazzy the dollar bills to take to the stage. “I want everyone to see the beautiful new girl,” he explained. Jazzy started to enjoy the perceived attention as she wiggled her way to the stage.

It was attention she got from Steve. He went to great lengths to tell her about each performer, all of whom he knew personally, some in the biblical sense. Jazzy was in turn impressed with the tough life but resilient personality many of the girls exhibited. One was a talented and celebrated performer by night, escaping from the much bullied life of an effeminate college boy by day.

As the first show ended the three made their way to the disco, now much busier than they had seen it before. Steve asked Jazzy and Martin to join him in a dance but Martin interjected, “you two go ahead. I’ve had a really long day. I’m going out to the car to lay my head back and relax. You have fun and Jazzy you know where to find me when you are ready to go home.” Turning to Steve, you take care of her, you hear.” It was more of a request than a threat.

“I’ll do my best,” replied Steve as he placed his arm around Jazzy’s waist. Jazzy looked at the hand on her hip but made no attempt to remove it or to move away.

‘This is going better than I thought it could’, Mary thought to herself as she headed to her car, ‘but maybe I should be annoyed that Steve has so easily forgotten about the missing Mary.’

A half hour later or maybe it was an hour Martin was wakened by a knock on his car misty window. Startled at first, he soon recognized Jazzy’s voice, “hey wake up and open up.” Just behind her, stood Steve.

“Hi girl, how’s it going?”

Jazzy continued, “Great! I guess you are really tired. I told Steve where we are staying and he says it is pretty well on his way home. He can drop me off if you want to leave.”

Privately this is what Martin had hoped would happen. This is why he’d chosen to tip off Steve to be at the club. He wanted Jazzy to get the ‘full-bodied flavor’ of being a woman and Steve would be one of the best to give it to her. He knew Steve loved his t-girls but just as much he loved making the girls feel good about themselves and that included respecting their limits. Martin knew from experience that Steve would not push Jazzy to do anything she did not want to do.

As Martin got ready to leave he spoke to Jazzy privately, “My ex used to do this for your mom. Here’s some mad money” he said while putting $40 in her hand, “put it away and keep it just in case you need to take a taxi home.”

“Thanks, Grandpa. You’re the best.”

I’m sorry I do not yet have a first person account of what happened between Jazzy and Steve the rest of the evening. Mary did say that it was early in the morning before Steve dropped Jazzy off, looking none the worse for the experience. Mary had asked Jazzy what happened but only got a brief “I’ll tell you later” as Jazzy finished a glass of milk and made her way to her room.

“Take off your makeup before you lie down,” Martin called out, “I don’t want stains on the pillow cases.”

It was just before noon when Jazzy, now back to Jason, emerged from his room.

“So tell me all about it,” I said to Mary as we dined together at the same Parliament House that had been the setting for her grandchild’s novice experience.

“Funny but that is what I said to her. I will tell you but it will have to wait. Here come the other girls. I can tell you that the evening was pivotal in helping Jason/Jazzy decide his/her future.”

Tags: featured, Jazzy, Linda Jensen

Category: Transgender Fun & Entertainment