Which Patty Keene: The 13-Year-Old Boy or the 16-Year-Old Young Woman?

[Part 1] [Part 2] [Part 3]

Patty Keene (not her real name) is a very good looking post-op transsexual who lives and works in Toronto, Canada. For the most part she socializes only with her ‘straight’ friends but occasionally returns to her roots in the LGBT community. I was lucky enough to meet her at a recent Coronation Ball of Toronto’s Imperial Court. As we got to know each other I was able to learn her amazing story. She has graciously consented to allow me to re-tell the story on the condition that her name and some other facts be re-arranged, so to speak.

In the first part of her story I related how Patty had grown up as a boy maturing intellectually very early but physically very late. Thanks to being pushed ahead in grade school she reached high school and approached her sophomore year (Grade 10 in Ontario) without any sign of puberty. I also related how her interest in wearing her mother’s clothes developed to the point where at age 12 she felt comfortable going out, passing as a 16 year old girl and even having a brief unconsummated love affair with a senior at her high school.

All this went seemingly unnoticed by her busy parents who, while concerned about their son’s late blooming, were too occupied with changes in their own lives to do anything about it. Mr. and Mrs. Keene were about to move to South America while shipping their son off to Mr. Keene’s old boarding school. In the meantime for the summer Mr. Keene’s sister, Patty’s aunt, would be moving in to keep an eye on him. Patty had agreed to the arrangement on the condition that summer camp was taken off the table.

Just in case you are thinking this will be one of those ‘dominant aunt feminizes the young man’ stories; it wasn’t. In fact Patty hardly saw Aunt Patricia. The aunt had a job and often on evenings and weekends she was off somewhere with her boyfriend. Patty took over the household chores which included monitoring the family mail which included mail from Lakefield, the school she would be attending in September. Apparently Aunt Patricia was very helpful to Patty in unknowingly providing some necessary identification papers such as copies of Health and Social Insurance cards. She also, unknowingly, became Patty’s supplier of birth control pills that the studious youngster had learned would a useful supply of estrogen and later would supply an image of worldliness when her future classmates learned that she was apparently ‘on the pill’.

Now here I have to be a bit sketchy on the details because I don’t really know how she did it but my friend Patty was able to, let’s say, adjust the paper work so that the application to enter the school was seen to be for one Patricia (Patty) Keene and not Patrick (Patty) Keene (and how had that mistake been made in the first place!?).

Apparently the school was very apologetic about the mistake as that would be the first year they would have girls in residence at the school and they would be happy to have the daughter of one of their most successful old boys in the first class. Patty was sent a clothing list and the name of a store where the school uniforms could be purchased. She spent several wonderful days shopping at the Eaton Centre and at the school’s exclusive men’s wear store that was bringing in the girls uniforms, Aquascutum no less, just to keep the school, one of their best customers, happy.

Soon it was time to head ‘up to Lakefield’. How did Patty get to leave home, saying good bye to her aunt, as a boy and arrive at the school as a girl? Would not the students, Hogwarts style, be traveling all together?

Patty said she had worried about that for some time. The plan she concocted was ingenious and carried out with precision. The school’s charter bus, for those whose parents couldn’t deliver them, was to be leaving Toronto on a Tuesday. Patty told her aunt that as a new boy she had to be at Lakefield on a Monday. Early Monday morning the aunt said good bye to young Patrick as he boarded a regularly scheduled bus to Peterborough, the nearby town where he said the school would be picking up the students. She did not seem curious as to why there were no other students taking the same bus. She was in a hurry to get to work. Long story short: as soon as Patrick got to Peterborough he turned around and took the next bus back to Toronto, talked his way in to a hotel room and started his transformation to Patricia, a person he hoped to be for the next three years.

The next day, complete in her school uniform plaid skirt, white blouse, navy jacket, knee socks and saddle shoes pretty young Patty Keene joined about 20 other boys and girls on their way to Lakefield College. The boys were mostly returning and seemed unsure of themselves in the company of the girls. The girls, many of whom knew each other were more relaxed and chatty. Patty was the one nervous girl. At first she sat alone but eventually one of the other girls moved to the empty seat beside her to say hello. It wasn’t long before Patty was introduced to all the girls as the boys sat at the back talking quietly to themselves. Patty was glad that none of the boys were pointing to her and saying ‘hey, that chick looks like a dude’ but why should they? At the age of 13 and going in to Grade 10 Patty had yet to show any signs of a growth spurt or developing any male secondary sex characteristics. In fact thanks to Wildside, at the time a new store just opening in Toronto, Patty felt that her new gaffe and padded bras would give her all the feminine image she would need to present as a ‘late blooming’ teenage girl.

On arriving at the school the boys and girls were separated to be taken to their respective dormitories. One dorm building was reserved exclusively for the girls. At someone’s suggestion the beds were now separated by modesty partitions and that suited Patty just fine. However she also got a crash course in how adolescent females live and interact with each other. Modesty partitions be damned. They freely walked around in bras and panties. They gossiped and giggled and hugged each other. Yet they respected each other’s limits. No one teased Patty because she preferred to keep her pajamas or other clothes on. They assumed she was shy about her slow developing breasts. They understood that and she was not alone.

You would think that someone like Patty would be read and drummed out of the school within days and that as soon as the first letter to her parents describing their daughter’s progress there would be hell to pay. But no, the school’s information and form letters had been designed to be gender neutral. Patty was Patty in either gender. She settled in to the school routine very well, did exceptionally well on the cross country running team and even was chosen for the Firsts in field hockey. (I don’t really know what that means but Patty thought it was something noteworthy). By observation Patty learned the art of sitting while wearing one of the school’s uniform short skirts. She learned to walk with short quick steps when alone and short slow steps when in the company of other girls. She learned to tilt her head to the side and smile when talking with boys and to avoid direct eye contact with boys she met in the halls. She learned how to fake a menstrual period. Most importantly, being the 1980s Patty learned how to use a curling iron without burning herself or her hair.

The elite anglo society of Toronto is not that large. It was inevitable that there would be at least a few boys from St George’s, her old private elementary school, now at Lakefield. Naturally they asked if she was related to Patrick Keene. Patty knew she was really home free when they accepted that he was her younger brother and was now happily attending Lawrence Park Collegiate.

For close to two months Patty Keene lived the life of a brighter than average sixteen year old teenage girl settling in to boarding school life. All was going well. Starting with chapel in the morning and ending with evening study hall Patty and the other girls happily settled in to life at Lakefield and soon had broken all the ice with the boys. Inevitably some relationships started to develop. A few boys started to show an interest in Patty. She liked the attention but was in no mood to get in to a serious relationship.

Fortunately, her old jogging partner, the soccer playing Adam, became her excuse. She could not be seeing any of the Lakefield boys as she was now going steady with Adam. Some of the boys knew of him and had played soccer against him. They respected that Patty would be loyal to him. That is they all did except one.

There was one boy who showed an interest in Patty that she liked in return. They had a lot in common – an interest in history, scholastically gifted and with their parents away working on other continents. It wasn’t long before Patty and Trevor were spending a lot of time together, going sailing, taking walks in the woods and studying together. From hand holding their intimacy advanced to kissing. Patty enjoyed the contact but like any good girl going steady with another boy she resisted letting Trevor get to second base.

Did Patty ever worry about what would happen if Trevor discovered her true gender? For sure she did. However she seemed to be addicted to his company and to the good feelings they shared. There was an expression they used at the school to refer to a young man who got a painful feeling in his groin when his arousal was frustrated from completion. It was called having blue balls. Patty had little doubt that Trevor would be suffering from blue balls. However there was one day when you might say things got a bit out of hand. At the time many of the school boys had little cabins, called huts, in the woods. Usually the hut had been just a place to hang out in their free time but with the coming of the girls it became a mark of distinction to get a girl alone in your hut. One afternoon Trevor invited Patty for tea in his hut and she agreed to accompany him. Their usual kissing became more heated and Trevor’s hands wandered quite a bit. Risking discovery, Patty had to take a bold action she had read about. Telling Trevor that she could not risk getting pregnant she asked if he would like fellatio. He agreed and for the first time Patty felt a penis in her mouth and a very short time later she felt and tasted the result.

Trevor immediately became very apologetic and suggested that they should go but Patty was not leaving without having her tea and biscuits. By the time they did leave Trevor was somewhat recovered and she was able to extract a promise that he would tell no one and he would never try anything with her again.

So did her life at Lakefield go on for three years as Patty had hoped? Hardly. As Patty told it she was ‘magic dragoned’. She had to explain that, too. There was a song called Puff the Magic Dragon where Puff is the favorite toy of a little boy. They were inseparable until one day the boy started to grow up. He left his dragon behind and started pursuing older teenage interests. “Oh, like in Toy Story?” I asked.

“Whatever.” So after about a month at the school Patty started to notice little changes. She was developing hair on her arms and even a slight growth on her upper lip and sideburns. She also felt herself tighter in her shoes and at funny times her voice would become raspy — a cold she explained but she knew what was happening. She thought she could deal with it all but then one night as she slept she had this incredibly vivid dream. She dreamed she was at the lake on the school raft with Trevor when suddenly they started to make out. Yes, you guessed it Patty awoke with a moan and a gooey liquid leaking or leaked from her penis. She went to the bathroom, cleaned up and went back to sleep.

This was her first wet dream. They reoccurred almost every night and every night Patty had to get up, go to the bathroom and clean herself up. She took to wrapping a face cloth in her genital area. That helped control but not stop the flow.

It seemed the wet dream crisis was just another challenge that Patty was going to handle. Despite her slight body changes she was handling other aspects of boarding school life very well. She excelled in academics and enjoyed her developing interactions with the other girls who of course treated her as one of their own. All that changed late one night as Patty was in the bathroom cleaning up after yet another wet dream. In her haste or in her sleepiness she made one slip back to an old male habit. She was standing, holding her penis, relieving herself in to the toilet.

“Patty, what are you doing?” she heard a voice behind her. “Do you have a penis?” the voice asked. It was Margaret, one of Patty’s best friends and one of the worldlier among the girls of that dorm.

Patty tried her best to tuck her equipment away but Margaret, who had two older brothers, knew exactly what she had heard. “Let me see,” she insisted. Margaret marched right up to Patty and put her hand on the crotch of our now-frightened heroine. “Oh my God! Patty! What are you doing? Who are you?” exclaimed Margaret, probably loud enough to wake the rest of the dorm.

“Shhhhh!” Patty had tried her best to convince Margaret to be silent. “I’ll tell you if you can keep a secret.”

Like all teens Margaret loved hearing secrets so she stopped to listen to Patty. Patty told Margaret the ‘Reader’s Digest version’ of her life the last year and of how she was adopting a female identity to escape the bullying and derision she had been receiving as the smallest boy around.

Here again I thought Patty was going to tell me the stuff of another crossdressing pulp fiction novel but no. While Margaret loved hearing secrets she did not love keeping them. It was only a matter of hours before everyone in the school administration knew of Patty’s situation. She was called in to see the school headmaster. Her parents were called in Brazil. She was moved to the school infirmary. She was not allowed to attend classes. She was to stay basically to herself until her mother could come to bring her home. At one point they were going to make Patty wear boy’s clothes and get a regulation school haircut but something made them change their mind. Patty was allowed to stay a girl until her mother came to pick her up. Patty had no further contact with Trevor or any of the other students

Just over three months after Patty Keene arrived at Lakefield College as one of the first classes of girls she quietly left without a word of good bye to anyone. Her name was expunged from the school records.

When her mother arrived to take her home there ensued a ride mostly in silence. Patty was very happy that her mother had not brought a change of clothes for her or insisted on stopping off at a barber shop on the way back to Toronto.

So how did the 13 year old crossdressing student, suddenly and quietly expelled from his boarding school become the gorgeous TS that I met at a night club in Toronto? That is a story in itself, so unusual for a period before the Internet. I’ll provide all the details in my next column.

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

Category: Transgender Fun & Entertainment