“Maybe it’s in the Genes, After All”

Last month 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 had gone so far as to put on a short skirt and dance to Man, I feel like a Woman. Now, he confessed, he wanted to see what it was like to do a complete transformation.  Martin agreed to help Jason and to not tell anyone.

“But you’re telling me,” I reminded Martin who was very much Mary as we sat in her Florida room enjoying some cool drinks.

“That doesn’t count. I can trust you and I know if you write about this you will change our names to protect the innocent.”

When we left them Martin had suggested to Jason that the only way to find out how deep was his interest in wearing women’s clothes was to go all the way. They determined to find a business in Orlando that could do a makeover for Jason. Martin (Mary) knew exactly where to go but he wanted Jason to do the discovery.

Home and to the Internet they went. Martin’s heart was racing. He felt like going to his closet to pull out the small ‘Mary’ suitcase he had ready for the trip back to his retirement community. He resisted. Instead he got beers for each of them and suggested that Jason log on to the computer and start searching. Martin felt as if he was back being a scout leader teaching map and compass: he knew where he wanted the young man to go but it was up to Jason to find it.

Jason proved to be pretty adept with the search engine. Without any prompting he typed in ‘crossdressing services in Orlando’. It occurred to Mary this was not the first time Jason had gone down this path.

Many of you will know that with a query like ‘crossdressing services in Orlando’ all kinds of suggestions are going to come back from Google.

“Bingo,” thought Mary. Near the top of the first page was his target.  He played it coy. “Wow! Look at all of those choices,” said Martin, “who would have thought it?”

“I know,” Jason replied, “I was looking here a few days ago and this is pretty much what I found. What is with that Glamor Boutique? They are not even located in Orlando.”

“Well they are well positioned and they probably do a lot of on-line business in this area.” He could have also mentioned that the positioning is based on the number of ‘hits’ they are getting from his computer.

Jason went on, “I didn’t know where to turn so this is when I decided to confide in you.”

“It is probably also when you discovered how expensive it could be,” chided Martin as he playfully patted Jason on the back.

Ignoring the dig and  Jason said, “I think I want to try this Trading Faces.”  He was pointing to the third entry on the page of search results:

Welcome – Trading Faces, Crossdresser & Transgender Makeover
tradingfacesorlando.com/?
Beauty Makeover, Male to Female, Crossdresser and Transgender, Orlando Florida.

Martin smiled. That had been his first choice, too. He had never met her but he’d heard great things about Josett, the owner. She seemed to be one who really cared about her clients.

“Well it is near the top of the search list so that must mean something. Let’s look at the website.” After a few clicks and a bit of reading and looking at the photos the two were satisfied that they should contact Trading Faces. “Why do you like it,” Martin remembers asking Jason.

“In the photos everyone is smiling, they are on a first name basis and we know what services we’ll get. And the makeover photos look as if they were taken in somebody’s home, not just in some cold studio.”

Martin was impressed with Jason’s perception, “you should send an e-mail right now. They say it might take a few days to hear back.”

It did take two days to be exact during which time Martin and Jason talked more than they had in the previous few weeks. It seemed as if a floodgate of emotion had opened for Jason. Telling his grandfather about his feelings and about the guilt associated with his crossdressing urges went a long way to relieving those feelings.  Martin played the wise counsellor, helping Jason to bring out his feelings while keeping his own in check.

The initial reply from Trading Faces was a bit of a surprise but it set the tone for the rest of the relationship. Martin had expected a form reply with a ‘you can have an appointment at such and such a time and please bring cash; we don’t take credit cards’.  Instead Jason received a lengthy reply that asked as many questions as it gave information. For instance, Josett, the owner, wanted to know what Jason was seeking to get out of the experience. “That makes a lot of sense,” said Martin, “say you are going there expecting to dress more to get a bigger sexual thrill she is probably not going to accept you as a client.”

Jason responded to the e-mail frankly saying that he had been ‘experimenting’ with lingerie for some time but had never seen himself in a full female image. He was looking for that experience and wanted her help to get it just right. He wanted to know if ‘crossdressing’ was his ‘thing’ or not. I didn’t know they still use that expression, mused Martin.

Josett agreed to see Jason. She sent a detailed set of questions about what he would be bringing and was there anything she could buy in advance for him. She asked for his sizes. He knew very little other than his bra size (36c) and panties (5) but he had those already. Martin suggested to Jason that they could pick up some inexpensive items at WalMart, that it was primarily hair and makeup that needed her help.

Eventually it was agreed that the two would meet Josett for a talk at a restaurant near her house and if all went well she would take over Jason for two hours. She warned them that it might take longer “because I like to talk” but she would only charge for the two hours.

Exactly at the agreed time Martin and Jason met Josett at a small Italian restaurant in Davenport, just outside Orlando. They talked and the more they talked the two men become more at ease with Josett and Jason came to realize that he was not alone in his desires.  In the end it was agreed that Josett would take Jason for his makeover and Martin said he would come by to pick him up two hours later. “Better make it four hours. I think this young person is going to take more time,” said Josett with a smile.

“I’ll be there at five,” agreed Martin.

On the way to her studio Josett and Jason stopped at a drug store to pick up his first cosmetics. “You can’t really buy cosmetics without first seeing a person’s complexion and skin tones,” explained Josett.  Jason was uneasy at first but became relaxed even as Josett used various testers on the back of his hand.  Getting excited, Jason ventured that he wanted to buy a very bright cherry red lipstick but Josett cautioned that he might want to go for a more subdued, natural look. “Save that hooker look for Halloween,” she said, “or maybe for a drag show.” She winked as Jason blushed.

I could write thousands of words on how Josett transformed Jason not so much by doing the work but by showing him how to do it for himself.  I was reminded of the saying about teaching a man to fish you feed him for a lifetime. They tried several looks from ‘girl next door’ to someone ready for a night on the town. Jason had natural beautiful long hair that he usually kept tightly tied back. Josett conditioned and styled his hair, blow drying it to give it a wave and body. She brought his hairline forward and across his forehead.

When Josett first led Jason to a mirror there was a long period of silence. Jason’s jaw dropped and his eyes started to tear up. “I would never have thought I could look like this,” he marveled, “I’ve waited a long time to see this.”

More make up looks and more outfits followed. Josett got Jason try a couple of her loaner wigs. “You don’t need a wig but just see the different looks you can get,” she said. For each look Josett would use Jason’s camera to take some photos so Martin could see all the results. “I don’t take any photos with my camera,” Josett had warned, if you want photos bring the camera yourself and take it away with you. That way you know I won’t be using or misusing your image.”

Just as they were getting to the glamour shots Martin arrived. Josett answered the door and led him to the studio room. “Oh, excuse me,” he said when he saw Jason, “I was expecting someone else.”

“Grandpa, it’s me.”

“Oh MY GOD! I would never have known. If I wasn’t 65 and a blood relative I’d be pretty hot for you right now.” Martin had spent the better part of his life involved in male-to-female transformations but it still took him by surprise how gorgeous his own grandson looked right there.  “How do you feel?” he asked.

“It’s strange. I look in the mirror and I look at the photos she’s taking but it’s hard to realize that is me.”

Josett finished up the last touches before the three sat and chatted for a while. Jason was effusive in his thanks and so was Martin.

“What are you going to do now?” asked Josett.

“I guess that is up to Jason,” said Martin. “I think he knows now what he looks like as a woman. That’s what he wanted to do. Probably he just wants to get changed and get home.” Martin’s heart was pounding as he spoke. That is not what he wanted to have happen but he knew it had to be Jason’s call.

“Grandpa, seeing as I’m all made up and we have these clothes would you mind if I stayed in character a little longer?”

“Sure, no problem,” said Martin, “Well there is one problem. We’re going to have to give you a new name. How about we call you Jane or Janie?”

“That’s a little old fashioned. You might as well call me ‘Mary’ or ‘Linda’.

“Ouch,” Martin thought to himself.

(“Ouch,” I exclaimed as Mary told me the story.)

“Okay you pick,” Martin continued.

“I like Jasmine or Jazzy.”

“Jazzy it is,” agreed Martin, “Let’s settle up and then we’ve got a few stops to make before we get home.”

“I’m going to take this young lady shopping for some more outfits and then out to dinner,” said a smiling Martin, “and then we might continue on for a night on the town.”

“I’m game,” said a happy Jason as he tried to effect as feminine a voice as possible.

Just then Mary’s phone rang. She got up to answer it. She was right back. “Linda, it’s Jason. We’re probably going to be a long time. We’ll get together at the club later and I’ll tell you all about it.”

Good to her word, that evening Mary told me all about their night on the town and Jason (Jazzy’s) surprising decision. Check back in four weeks and I’ll fill you in.

Linda’s final note: For those who want to check it out and haven’t yet done so the Trading faces URL is www.tradingfacesorlando.com 

Tags: crossdressing, featured, makeovers, transformation, Transgender

Category: Transgender Fun & Entertainment