Jason’s Transformation: One Small Step and One Giant Leap

Several weeks ago I introduced you to Mary, a life-long crossdresser, twice divorced and once widowed. She spends her winters in a retirement community in Florida where she is out to the community as Mary. However on the rare times when members of her family visit from up north she rents a condo in the Orlando area. She puts Mary away and becomes Martin, an image of her former self. As far as Mary/Martin knew, none of her family was aware of Mary.

That all changed when grandson Jason, came to spend a month with Martin. While watching a football game at a local sports bar Jason revealed that Martin’s ex-wife, his grandmother, once spilled the beans about Martin and their somewhat fetishistic love life. Jason went on to confess that he had followed grandpa’s lead and spent a lot of his teen years enjoying sexual pleasure while wearing bras and slips. (Yes, girls, Jason had feelings of guilt, too.)

Jason further confessed that he now wanted to ‘take his game to the next level’ as they say in sports. He was curious what it would be like to appear completely as a woman. With Martin’s subtle ‘you’ll never know unless you try’ in his ear Jason’s Internet research took him to an Orlando based business called Trading Faces.

Now, one appointment later, Jason has looked in the mirror, lost his breath and gasped at the vision he saw looking back at him.

With their time at Trading Faces concluded Martin found Jason reluctant to de-transform. “No problem,” said Martin, “we are ready for that.”

As they prepared to leave Trading Faces, Martin and Jason were glad they had heeded Josett’s advice to “bring something appropriate to wear as when we are finished Jason may not wish to shed his new appearance right away. He may want to try it out in public.” At first Jason had been skeptical but now he was glad they had followed her advice.

On the way to Clermont they had stopped at a WalMart and picked out a blouse, sandals and pair of girlish shorts Jason could wear if he felt so inclined and that Martin dearly hoped his grandson would want to wear. Now they were taking off the tags as Jason for the first time donned his own girlish outfit.

“I think Jason is no longer an appropriate name,” said Martin, “how would it be if I called you Jane?” he asked.

“It’s kind of old fashioned,” the grandson replied.

“Old fashioned?”

“Yes, it’s like Mary or Linda. No girls my age are called Jane,”

Ouch, Martin thought, “Jazzy, it is!”

(Ouch I thought when Mary told me the story.)

The two bade farewell to Josett and started the drive back to their rented condo. ‘Jazzy’ pulled down the visor mirror to admire herself.

“How do you feel?” asked Martin.

“It’s hard to describe. I’m always so aroused when I put on just a bit of lingerie but this feels more normal. My hair is different. The bra and boobs feel wonderful, I’m wearing makeup and my clothes look and feel different but underneath I still feel like me except maybe a little more awake. And where is my erection, if you know what I mean.”

“More awake?” Martin asked, ignoring for the time, the last comment.

“For a long time, since Sandi and I broke up I haven’t felt like doing anything, working, going out or anything.”

“I know,” interrupted Martin, “that is why I wanted you to come down here -– to see life goes on. And now how do you feel?”

“It’s not so much life going on as it is a new life beginning. I’ve felt so guilty about always masturbating when I put on my bra and panties. Now it makes sense.”

“Well, wait a minute,” advised Martin, “sex is sex but life goes on. You don’t feel like masturbating right now, do you?”

“No. As I said, I don’t even have an erection. I can’t believe it?”

“That’s good because I just had the car cleaned,” Martin joked. “I don’t know much about crossdressing,” he lied, “but we might be able to thank a guy named Pavlov for the explanation of why you don’t have an erection now when you are fully dressed.”

“Is he the guy who designed this tight thing Josett sold me to strap my balls in?”

“No, he’s the scientist who first showed something called a conditioned response. He used dogs to show that if you rang a bell just before you gave them food soon they would be salivating at the sound of the bell and not at the sight or smell of the food.”

“I don’t get the connection.”

‘Nobody ever does,’ thought Martin. He continued, “When you put on a bra and panties you knew you were going to masturbate and ejaculate so the thought of putting on bra and panties got you aroused. This time you knew you were in a situation where you couldn’t or wouldn’t be masturbating so you were able to block the conditioned response.”

“That makes some sense, I think”

“Listen Jason, I mean Jazzy, you are taking on a great responsibility now. You are projecting the image of a female in public. You have to respect that image and honor the woman you are representing. Make Jazzy proud to exist. Respect Jazzy and others will respect her, too.” Martin wasn’t sure where those words were coming from or how Jason would receive them but he was soon to find out. “I’ve got an idea,” Martin continued, “let’s go out tonight to dinner and to a club. We’ll be grandfather and granddaughter.”

“Could I do that?”

“You have nothing to fear but fear itself.”

“Why do old people keep saying that? But no,” said Jason, “let’s be father and daughter. I’ve always thought of you as being too young to be my grandpa anyway.”

Martin smiled. “Let’s get you something appropriate to wear this evening,” he said as he turned the car toward a nearby Beall’s Department Store.

It didn’t take Jason/Jazzy long to feel comfortable in Beall’s. He looked at other people but they were not looking back. At 5’ 6” Jason was short and slight for a man but fit right in with many of the women around them. Most of the time at Trading Faces Jazzy had been wearing a wig borrowed for the photo shoot but before they left Josett had fluffed out Jazzy’s hair and created a slight bang. No matter that her hips were a little smaller and her shoulders slightly wider, with her sideburns shaved up and eyebrows shaped Jazzy was every bit passable.

“Try not to look at people,” Martin advised, “women avoid eye contact, especially with men, I’m told.”

Jazzy took the advice and also the advice to take slightly smaller steps and slow down to look at things, touch fabrics, pick up purses and generally be more leisurely in the store. Martin wondered if he should lay off the advice for fear of outing himself but rightly figured Jazzy would attribute it to the wisdom that comes with the years.

“Would you like to wear a dress tonight?” Martin asked Jazzy as they arrived at the dress department.

“Oh my god, there are so many choices,” exclaimed Jazzy, already adopting the language of his/her female peers.

“Look around. Try on any that you like. We’ll buy two, just in case.”

“In case what?” asked Jazzy.

‘In case you want to go out again tomorrow’ thought Martin but he said, “just in case” and left it at that.

With a little prompting Jazzy picked out four dresses to try on. “Do you think they’ll let me try them on?” she asked.

“Look, you may feel a little awkward but for all they know you are a twenty-something young lady getting ready to return to college and your granddad or dad is helping you out with your shopping. I’ll walk with you over to the fitting room.”

Jazzy tried on her first dress and like all of us had a bit of trouble with the back zipper. She came out of her stall and asked Grandpa for help. “Why don’t you try pushing it up from below as far as you can and then reach back over your shoulders, pull up the fabric and grab the zipper from above?” suggested Martin.

“Hey Grandpa, you’re pretty good,” said Jazzy as the suggestion worked, “How do you know all this?”

“Oh, I’ve watched a lot of women get dressed to go home,” said Martin as they both laughed.

As Jazzy returned to the dressing room, Martin heard himself say it for the first of what would be many times, “Unbelievable, unbelievable but true.”

So it was that with Grandpa’s help Jazzy picked out two dresses, one a summery green and white print dress that Martin insisted she buy and the other a little black dress that he’d heard every girl should have in her wardrobe. Needless to say they also found a couple of skirts, a blouse and tank top that Jazzy just had to have. They toyed with the idea of buying a bikini for Jazzy to wear to the condo pool but Jazzy decided, with a touch of her groin, “maybe not just yet.”

“Now for some jewelry; I’m sure you’ll want to wear earrings.” Martin suggested, “And you’ll need panty hose and of course some of your own makeup to add to the starter kit Josett gave you.”

The two made a whirlwind tour of Bealls picking up items as quickly as Martin suggested them. As they entered the checkout line Jazzy asked, “what about shoes and will I need a purse?”

“Payless,” said Martin, “ah, I went to one of their stores with a friend a while back.” He tried to seem not too knowledgeable, “they seemed to have a pretty good selection of women’s shoes and purses. I noticed one of their stores just up the mall.” They made quick work of Payless as Jazzy easily found pairs of low and high heels and a conservative black purse that would ‘go with everything,’ they joked. Then Martin added to himself, “Unbelievable, unbelievable but true.”

So with Jazzy carrying many packages and Martin carrying a few more dollars on his credit card the two returned to the rented condo. The security guard at the gate with whom Martin liked to banter seemed not to notice that his young male companion had been replaced by a female one.

In the interest of time I’ll skip over the details of how they got ready to go out, how Jazzy had a minor crisis when, despite all the good intentions, an ill-timed ‘boner’ appeared under her new dress, how Martin suggested she go to the washroom to ‘take care of it’. Advice followed and while Jazzy calmed herself Martin made a few phone calls.

Shortly thereafter as Martin sat at his computer answering a few of his e-mails (and reading the latest on TGForum, no doubt) Jazzy appeared coming down the condo stairs wearing the new green and white print dress. “Unbelievable,” said Martin, “unbelievable but true.”

“What’s that Grandpa?”

“Oh it’s nothing. I was just thinking how unbelievably cute you look.”

“Thank you. I feel wonderful.”

‘If you only knew how unbelievable this is for me,’ Martin thought to himself.

Martin’s plan was for the two to go to a nearby Denny’s restaurant where the two had eaten several times in the preceding weeks. He had to assure Jazzy that everything would be okay and that she looked just right for the restaurant, that he was sure no one would recognize her.

“But what if your friend Catherine is working? She’ll know me,” protested Jazzy.

“Trust me on this one. There is little chance she would be serving us and if she did ask anything we’ll just say that Jason has gone home and his sister is now visiting. It will be fine.”

No sooner were they seated and the menus presented than Jazzy pointed to the menu cover and exclaimed, “Oh my god! That woman is wearing nearly the same dress!”

“Oh really? What a coincidence! See she has great taste, too.”

(Here I interject to say that Mary had remembered my personal experience with the same style of dress and the same menu photo. When she saw the dress in the store she had determined to give her grandchild the same great experience. –Linda)

However that was not the end of the coincidences. Their server was the same Catherine who had waited on them a couple of times and who enjoyed Martin’s banter. “Welcome back to Denny’s. My name is Catherine, as you know. Where is your grandson, this evening?” she asked casually while placing two water glasses on the table.

“Oh, he’s gone back north. Now it is his sister’s turn to visit. This is Jazzy.”

“Nice to meet you, Jazzy. What a cute name! Let me tell you that your brother is handsome despite his scruffy exterior but you have him all beat. You are gorgeous, darling!” She winked to Martin.

“Thank you,” Jazzy found it hard to get the words out. Martin just smiled a big smile. During that dinner ‘thank you’ was a phrase Jazzy said a lot: Thank you for not being mad about Grandma telling on you, thank you for understanding about me, thank you for getting me to Josett, thank you for helping me satisfy my curiosity and thank you for the dinner experience.

‘Unbelievable, but true,’ was a phrase Martin kept thinking to himself.

All through the meal Catherine kept returning to see how they were doing. She seemed to take great interest in Jazzy, “My, that’s a pretty dress. You know, you have your brother’s beautiful eyes. Where are you going to college? “ Jazzy had to wonder if she had been read or not. When asked, Martin just smiled, “maybe she’s just taking an interest in my friends. Enjoy the compliments.”

The two had only a couple of days left together so their talk ranged beyond questions of gender identity. What was Jason going to do when he got back home? Would he get back to work or back to his studies? Grandpa let it be known that he expected the status quo would not be an option. Jason agreed. He joked lamely about a “career as a drag queen; only joking!”

Martin laughed but inwardly felt some concern that Jazzy may have some trouble with his new-found identity. Again Martin thought to himself, ‘unbelievable, unbelievable but true.’

When Catherine presented the check for Martin to pay he said it out loud, “unbelievable, unbelievable but true.”

Jazzy looked somewhat quizzical but said nothing. Probably she assumed it was another compliment headed her way.

“Jazzy,” said Martin, “here’s a little suggestion. The dining took off most of your lipstick. Why don’t you go to the little girls’ room to freshen up and while you are there use the toilet. We have a bit of a drive ahead of us.”

“Now, you’re sounding like Mom,” said Jazzy.

“Remember to sit,” cautioned Martin as Jazzy started to get up.

“Just like Mom, she never liked dad or me spraying around the toilet. She always made us sit.”

“TMI,” joked Martin then he thought to himself, ‘unbelievable, unbelievable but true.’

Mary paused in her telling and looked reflectively out of her lanai toward the golf course beyond.

“Neat story,” I interjected, “but was Jazzy really so unbelievably beautiful?”

“That wasn’t it at all. Yes she was cute but what was unbelievable was all about me.”

“How so?”

“You and I are pretty much the same. We enjoy our femme lives and we enjoy each other’s company but we are pretty egocentric. We, at least I, enjoy my own femme image. I enjoy going shopping and trying on dresses. I enjoy being taken to dinner and I especially enjoy getting compliments on how good Mary looks.”

“True, true.”

“So it was unbelievable for me to be there watching Jazzy try on dresses, for me to be in boy-mode giving compliments to another TG and especially for me to be buying dinner for a TG while I was sitting there as a man. Then what made it even more unbelievable was that my date was also my grandson. It was unbelievable but true.”

“Life is strange,” I offered, “so what happened when you guys went to Parliament House?”

“Oh wait until you hear that,” Mary teased, “I’m saving the best part for last.”

“What do you mean wait? You are just starting to get to the good stuff,” I said mockingly. 

“We have a dinner reservation at the Country Club. It’s time to get changed. Come on. I’ll tell you all about it at dinner.”

It turned out Martin would only have a few hours to wonder what direction Jazzy’s life would take. That was the few hours they were to spend at Parliament House, Orlando’s largest gay resort/ entertainment complex. When they left Denny’s and after a quick stop at home for Jazzy to change in to a more club-appropriate outfit and brighten up her make up a bit that is where they headed.

“Do you think Catherine read me?” Jazzy asked.

“I guess we’ll never know,” smiled Martin, “how did you enjoy being there?”

“It was unbelievable,” said Jazzy with a wink.

“Unbelievable, but true,” replied Martin.

Tags: crossdressing, featured

Category: Transgender Fun & Entertainment