The Patty Keene Story — Part 1

[Part 1] [Part 2] [Part 3]

“In the Beginning I Just Wanted to Feel Older”

I LOVE my job. I mean this one where I sit at a computer and recount stories that interesting people have told me about their interesting lives. On a pay scale of 1 to 10 it’s a zero but on an interest scale it’s a 10+.

Sometimes I wonder (a) whether I’m going to have an article to send to our tough-as-nails editor/publisher/copyreader Angela and sometimes (b) I can’t wait for my turn to roll around so I can send her someone’s interesting story and then I can’t wait for the readers’ reaction/non-reaction.

I was afraid this month was going to be an option (a) until I met Patty. She told me of her youthful first forays in to the TG world. She is a post-op TS and a very beautiful one at that. Except that when we met we were at the Coronation Ball of Toronto’s Imperial Court I never would have assumed her gender origins to be other than female. She was there with a male date and for some reason the two took a shine to me. We danced a lot together.

She and I also had a long chat. If I had read her story in a TG pulp fiction novel I would have assumed it was just that — TG pulp fiction. However this came to me direct from the horse’s mouth. I then did some research and yes, there is a boarding school of that name. It does have that motto and it did switch from an all-boys school to co-ed at the time she said. Other than that all I can say is that there beside me sat an attractive woman who claimed to once have been a cute little boy. Most of the story is hers but I had to tone down some of the descriptions for this family publication. I also tell you that her family name is other than Keene. I am really thankful to Patty for agreeing to meet with me the next day to share her full story. I must also tell you that unlike a good reporter I have not been able to verify all the facts of this story. So it is told to you as just that: a story. I make no claim that everything or even anything reported is the truth. (I hope that makes the lawyers happy.)

Patty was born in 1975 and christened Patrick James (Keene). Her family, originally Irish, had long since been accepted in to the wealthy Anglo society of Toronto. The family lived in the Rosedale part of town, a community that reeks of money, new and old.

In most ways Patrick had a relatively normal childhood for one born to privilege, attending one of the private day schools serving the young of Rosedale, playing some sports, going on family ski weekends to resorts along the Niagara Escarpment and longer holidays to Quebec. In some ways Patrick was different from the norm. Always smaller than his age peers, Patrick made up for it with a large amount of brain power. In grade school he was accelerated through grades 4 and 5 in one year. While this was appropriate for his mental power it did nothing for his social standing with his peers. Perhaps jealous of his academic ability his classmates still looked on him as the runt of the litter and he was bullied accordingly.

During the summers, along with the rest of the Rosedale youth, he was shipped off to one of the many summer camps in the Muskoka region of Ontario. You may have seen him play a role as an extra in a popular movie partially filmed at his camp.

As he approached his teen years Patrick noticed that all his peers, male and female were in full bloom developing their secondary sex characteristics. Physically he had to look up to everyone, especially to the girls. By the time he turned 11 and many of his classmates were 13 he was nose to developing breasts with some of the more advanced girls in his classes. The testosterone fairy seemed to be slow in finding Patrick. At camp Patrick noticed he was lagging behind even the boys of his own age and his cabin mates noticed it too. His late developing body and long flowing hair earned him the nickname Patty. For many youth that would be a crushing blow to their self-esteem. Patrick took it in stride, laughed it off and started calling himself Patty.

His slight stature put Patrick/Patty at an athletic and social disadvantage among his peers. However his ‘go with the flow’ attitude did make him appealing to one of the counsellors. This counsellor made sure that Patty got extra sailing and canoe lessons and was taught how to use a map and compass so that Patty gained some proficiency in areas where size didn’t matter. Patty was able to win camp prizes for archery, orienteering and water craft. While circumstances might have been beating Patty down, being able to handle a sailboat and find his way through the woods gave Patty a self confidence that was going to serve him well in the next few years.

Then just barely turned 12, back from summer camp and about to enter high school Patty convinced his parents to cancel his enrolment at the exclusive Upper Canada College and to let him attend the public high school serving Rosedale and the surrounding areas. They agreed but as hard as he tried Patty could not seem to fit in. Being the smallest, whitest and blondest boy in the school did not help. Letting his hair grow long might have fit in with the rockers but did not endear him to the jocks or the nerds, his natural group. He was a loner and that suited him just fine as he was developing another interest.

With his father frequently away due to his job as the chief engineer of a large Canadian mining company Patty spent a lot of time in the company of his mother. He particularly enjoyed chatting with her while she dressed to go out or to go play tennis. He found himself studying the way she put on her bra and she massaged her breasts until they were in just the right place in the bra. Patty now thinks she was teasing the youngster, trying to develop his latent interest in girls. That might work with some boys but for Patty it gave him a major crush on his mother and on the clothes she wore. When he had the house to himself which was usual as soon as she left he would raid her laundry basket to try on the clothes she had just deposited.

Raiding the laundry basket, putting on some lingerie, arousal, erection, ejaculation, guilt and purge is all pretty standard stuff for us in the transgender community. However the ejaculation, guilt and purge part didn’t quite play out that way for Patty. While he got some great little erections the sensation of ejaculation was yet to be discovered.

What did happen was that Patty started to explore. He explored his mother’s clothes closet and her drawers. She was a petite athletic woman but her dresses were still a little large for Patty. Her shoes fit perfectly and her shorts, blouses and stretch sportswear fit him very well. So after school while most of his classmates were trying out for freshman football, soccer or community hockey teams Patty would head home with the hope that his father would be out of town and his mother would be rushing out to some committee or charity meeting or to a tennis game with her friends coming from their offices.

On those many occasions 12 year old Patrick, Patty for short, using clothing and a little make up borrowed from his mother transformed himself in to what he says looked every bit like 16 year old Patricia, Patty for short.

It was not long before Patty tired of seeing the same reflection in the same mirror. He wanted to explore a larger world and to see how others would react to the older teen image he was able to achieve as a girl but not yet achieve as a boy. Not far from their home in Rosedale was a large park area called the Don Valley. Through it passes the Don River, the Don Valley Parkway, railway lines and a series of parks and joining recreational pathways. Timidly at first, when circumstances permitted Patty would pull an outfit of his mother’s from the laundry basket, put on a little make up, fluff up his hair and head for a walk along a Don trail. Sometimes he would stop at a bench to read. Few people paid any attention to the young lady reading alone. Some older people would say hello. However there was one young man, a runner more than a jogger whose route seemed to take him past wherever Patty was sitting more often than did other people. Patty noticed that and at first it made him feel a little uncomfortable. However the young man never bothered him or ever said anything to him. Then Patty thought, why not try running, too. At camp he hadn’t been too bad at it and his map and compass experience made him comfortable on the wooded trails of the valley.

So one day Patty appeared at the park in ‘her’ mother’s slightly sweaty spandex, wearing a lightly padded sports bra and tee, her hair tied back in a ponytail and wearing an oversized ball caps. The first and second time Patty and the young man crossed paths the youth did not seem to even notice her. The third time Patty just happened to be standing at the water fountain near his/her usual bench. When the runner stopped for a drink Patty said hi. He looked at Patty shyly then asked, “excuse me but aren’t you usually sitting there reading a book?”

“Yes,” replied Patty, “You’ve inspired me to try jogging.”

“How are you doing?”

“I like it.” Patty says it felt like her heart was racing faster than it ever did when she was running up the sides of the valley.

“Want to run together?” the young man asked, “Maybe I can give you some pointers.”

“Sure, why not,” Patty replied, “but I can’t be too long. I have to be home to prepare supper for the family.” Patty did not know how she came up with that line but soon she was dishing out a whole different life story for the young man. And he was telling her about himself.

Patty told me that the man, actually a senior at the same high school Patty attended was running to stay in shape for soccer. He was hoping to get a sports scholarship to an American university. Instead of saying that she was a freshman at the same school Patty invented a story about being a nanny for a rich Rosedale family where often she was given the late afternoon off so that the parents could spend what we now call ‘quality time’ with their children. (That was not a likely story in the parent-centric world of Rosedale but young Adam apparently bought it.)

While they ran Adam and Patty talked about a lot of things, mostly sports, movies and music but some politics and of course relationships with parents and peers. Patty loved that Adam considered her to be first a 16-17 year old and second a girl. Adam obviously had a crush on Patty but he was too shy to act on it.

These encounters did not happen every day but they stretched over a couple of months. Every time they did get together Adam expressed disappointment that he hadn’t seen Patty the previous day or two. Patty was disappointed as well and she blamed it on work but usually the reason was a close call at home when mother would not go out or dad was coming home early. But also winter was coming on. Patty could not find among her mother’s outfits clothing suitable for cold weather jogging. It seems Patty’s mother was a fair weather princess.

There were also the occasional close calls at school. Young Patty would see the older Adam down a hallway or in the cafeteria and have to quickly turn away. It was not hard to stay away as freshmen were not welcome in the senior areas. Patty was always alone and Adam was usually with friends. Patty did admit to feeling pangs of jealousy when he would see Adam talking with ‘other’ girls.

Patty told me that she had liked Adam very much but not so much in a sexual way. More than anything she liked that Adam treated Patty as any respectful boy would treat a girl of the same age. If you thought this couldn’t go on forever you are right. There came the day that Adam invited Patty to accompany him to his soccer club’s annual Christmas party and awards banquet. He was pretty sure he would get the MVP award and he wanted Patty to be there with him and his parents.

Patty was very tempted to say yes and apparently she asked for time to check with her bosses before finally deciding it would be too hard to get dressed and get out of the house without one or other of her parents noticing. There was also the slight problem of not having a suitable dress to wear. Patty, the boy, could not really go to his parents and say, “I’ve been invited to a party on Saturday. Can I have a hundred dollars to buy a dress and another fifty to get my hair done?” Instead Patty made a clean break with Adam saying that her job as nanny was ending and she would be going home to Saskatchewan a few days before the banquet.

Only 12 years old, I think Patty showed great maturity in breaking off the relationship before being outed and before Adam ended up hurt and embarrassed.

The rest of the school year is blurry in Patty’s memory. She carefully avoided going out dressed and pretty well avoided contact with others. Patty’s parents talked about getting his testosterone and pituitary levels tested to see if there was an on-going growth problem but apparently they were talked out of it. Some boys just mature later than others they were told.

Patty continued to shine academically and adults who took the time to talk with him were impressed with his maturity. Patty secretly credited the time posing as an older teen girl for giving him the ability to talk at a level beyond his years.

Just as that school year was ending Patty’s parents hit him with a jolting bit of news. Mr. Keene was taking charge of the company’s mining interests in Brazil. Patty’s parents would be moving there so it had been decided that Patty would be shipped out to Mr. Keene’s old boarding school in Lakefield, Ontario.

Patty had heard lots about the school, some of which he liked, some he didn’t. At the time he didn’t like that his father often quoted the school motto to him, “Mens Sana in Corpore Sano: a sound mind in a sound body, now that’s a school that would make a man out of you,” his father said more times than were comfortable for Patty. Did his parents know or suspect about his crossdressing interest?

He liked that the school emphasized outdoor education and was academically strong but he didn’t like the all-boy environment. “That’s in the past,” said his father, “next year Lakefield will be co-ed. They are admitting an initial class of fifty girls.”

“I wish it was fifty-one,” thought Patty and right there was hatched the idea that was going to consume Patty’s interest through the summer months.

Chapter 2

Tags: crossdressing, featured, Identity, Linda Jensen, Transgender

Category: Transgender Fun & Entertainment