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Dreams Take Flight: Dan’s Story

| Jul 22, 2019
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[Part 1][Part 2][Part 3][Part 4][Part 5][Part6]

A quick review:

  • Patrick, a flight attendant for an airline based in Denver had a hobby. On some layovers in other cities Patrick would dress in drag to sing, karaoke style, at clubs in those cities.
  • Patrick’s ‘hobby’ was unknown to his crew mates until one evening they happened into the same bar where he was singing. They were there to watch the later drag show.
  • Patrick’s fellow flight attendants, both female, loved his performance and his femme persona so much that they conspired to have him work as a flight attendant one day as Patricia.
  • That day, despite his nervousness, went well for Patrick. He proved to be very passable and he enjoyed the better level of respect and friendliness he experienced from the customers. He thought about that a lot.
  • He also thought about how that original group’s first officer, the co-pilot, was also showing signs of being interested in ‘Patricia’. Cold toward the slightly effeminate, gay Patrick, Dan was quite friendly, even helpful, to Patricia.
  • After his return from Palm Springs Patrick did not immediately resume flying as Patricia but when together with that crew on a layover they all insisted on Patricia joining them.  So it inevitably came to pass that Dan and Patricia were finding time when they were alone together, just the two of them. It did not occur to them that the three others, seeing the signs of a budding romance were conspiring to give them some space.
  • For his part Patrick/ Patricia had no intention of getting involved with Dan. For one, workplace affairs often end badly and at the time Dan was married. It was one thing to have a one-night-stand with a married guy. He was often doing that with his gay bar encounters but with a married colleague no and no again. However that didn’t stop Pat from being curious. Why was Dan so obviously interested in Patricia? If the word admirer had been in use in those days Dan would have been one, for sure. One evening Dan told the whole story. It is worth retelling.

Dan’s story:

As Patty and Dan got to know each other better it was natural that they start talking about their pasts. Dan was intrigued that Patty did not consider herself one who was born gay or should have been born female. She told him that life circumstances and people’s preconceived notions about her small, slight physique had contributed to creating a mentality in her where at the right moment an encounter with an older man and the chance to create a femme persona were not abhorrent to her. To paraphrase a song that would come along later: ‘he kissed a man and he liked it.’

“But, what about you?” Patty asked Dan one evening as they nursed their drinks in the hotel lounge, neither wanting to say goodnight to the other, “you obviously like me as I am now when so many others would frankly be disgusted.”

“I guess I was imprinted at a very early age,” Dan told Patty. It all had started when he was a young teen. His family had moved to the Boston area where he quickly fit in with a new crowd of friends. However as it happened next door to Dan’s family lived a boy of his age, Ian, who did not seem to fit in with the crowd around him. He was nice enough, smart enough and athletic enough to be one of the gang however he just seemed to prefer to go it alone. Ian’s parents were concerned about him so they asked Dan’s parents if they could ask Dan to include their son in his activities.

Dan had agreed and for a while it had worked as the two became good buddies, playing sports together, studying together and even double-dating on the odd occasion.  However there were times when Ian became withdrawn and elusive. Dan could not figure out why but the answer was not long in coming.

One day after school Dan knew that Ian was home alone. Dan decided to drop in to see if Ian wanted to join the gang shooting baskets at the park. He knocked on their door but there was no answer. He entered and went upstairs to Ian’s room. No one was there. Then he heard a sound in Ian’s sister’s room. You guessed it. After all this is a TG e-zine. As soon as Dan opened the door he saw Ian standing there in high heels, wearing a dress, lipstick and eyeliner, a deer-caught-in-the headlights look in his eyes.

Now, 90% of the boys of that age would have bolted out of the house in disgust and rage. Not Dan.  He had been taught to be respectful of others and besides just the week before he had found and read a copy of Penthouse Digest with a story about a young crossdresser. To say the least Dan had been titillated by the story.

“What are you doing, getting ready for Halloween?” Dan had asked.

“Please don’t tell anyone,” pleaded Ian.

“I won’t,” Dan replied, “but what is going on?”

Ian began to relax a bit. Somehow he felt he could trust Dan. “I don’t really know what is going on. As far as I can remember I have wanted to be a girl. I almost feel I should have been born a girl,” he started.

“Well you do a pretty good job of hiding it,” commented Dan, “I had no idea.”

“I could control it pretty well until a few years ago when my sister started to go through puberty. As she started to develop breasts and wear a bra and cute panties I got so jealous. I have wanted to wear the same. So the urge grows and grows until I just have to get dressed. Sometimes I wear Sis’s clothes; sometimes Mum’s but I love the feeling. I feel so sexy?”

“Do you get yourself off?” asked Dan thinking back to that Penthouse story.

“Well yes I do… usually,” replied Ian, “I was just about there when I heard you coming in.”

“Then what happens after you cum?”

“I want to get changed and put things away as quickly as I can. I guess my guilt overcomes my passion.”

“That happens to me, too,” confessed Dan, “but usually I’m thinking of one of the cheerleaders at the time and I’m certainly not dressed like that.”

Dan left Ian to finish up what he had to do but he could not stop thinking of what he had seen. It really shocked Dan that the next time he wanted to play with himself his fantasy had changed from the cheerleaders to his friend and neighbor wearing that dress. And the next time and the next time.

Several weeks and a lot of tissue passed before Dan and Ian talked about what had happened that afternoon. Dan noticed a few changes in his friend. Ian’s hair was getting longer and so were his fingernails. It took a while to notice but Dan could see Ian’s eyebrows were changing shape, becoming thinner with a definite arch.

In the intervening time they had gone to a school dance with two of the girls in their group as dates.  “You seemed to be getting along well with Joanie,” Dan observed to Ian.

“She’s nice. I like her a lot but you know I spent a lot of time caressing her bra straps. She may have thought I wanted to feel her up but no, it was the bra I was after. I just loved feeling how it hugged her shoulder blades. She turned me on but all the time it was her clothes that were getting me hard. I’d love to know how it feels to be so sexy and turn someone on.” Ian was practically drooling.

“There’s one way to find out.” Dan could not believe he had said that but once spoken the words could not be taken back.

“Really?” asked Ian with a bit of excitement in his voice, “Do you want to make out with me?”

“Not you,” Dan corrected him, “but if you were all dressed, maybe? What is your girl name, anyway?”

“I haven’t thought of one.”

“How about Linda,” suggested Dan, “that means beautiful in Spanish.”

“Do you really think I’m beautiful?”

“Sure I do. If you have been able to knock the cheerleaders out of my fantasies you must be,” declared Dan, surprising even himself.

The two agreed to meet at Ian, err Linda’s, house the next afternoon when they knew they could have the house to themselves for at least several hours.

As arranged Dan walked in about a half hour after Ian had arrived home and went straight to his friend’s bedroom.  Wow, thought Dan. He knew it was his pal but ‘she’ looked so good.

Dan sat on the end of the bed and waited for Linda to sit beside him. They were both a bit nervous but as soon as Dan put his arm around his friend and they kissed all seemed fine and natural. Dan put his best ‘second base’ moves on ‘Linda’, lying beside her and rubbing the back of her thighs.  As she nuzzled in close to him, lying across his arm he was able to bend his elbow to caress her bra. She moaned in delight. 

At that time both were virgins and neither had a clear idea of how to hit the home run. Besides it took just the slightest touch from Linda to send Dan scurrying to the bathroom to clean up his released enthusiasm.

What was he going to do? Linda expected a dash for the door. ‘I’ve got an essay to finish before tomorrow,’ he would probably say.  To her surprise he came back to sit on the edge of the bed.  They talked about this and that. Dan apologized and soon his ardor had returned. They lay back together. This time it was Linda that had to make the dash.

Despite the rocky beginning it was not long before they two were regular love partners and still best friends when they were out as two guys. They talked about Dan taking Linda out for a date but it never happened. They were both high school seniors and as soon as graduation happened they headed in different directions. Dan joined the Army. Ian/ Linda headed to California. Occasionally Dan would hear about her, how she had got her gender reassignment done in Colorado, how she had been successful, married well and eventually became the head of a major national lobby group, having nothing to do with gender issues.

Dan parlayed a military career in to a flying one and had joined the airline about ten years earlier. He was due for promotion to captain but a slight economic slowdown had jolted the airline industry and caused the company to be laying off instead of promoting.  Dan was safe in his job. His marriage was a bit rockier. He was a pretty good husband and father. However he could not shake his memories of Linda and his appreciation for girls like her. When he travelled he often found a way to visit a convenient drag bar. His wife noted that he was not giving her his 100% and she soon was wandering to where she found appreciation.

It is actually a bit surprising that Dan and Patricia had not encountered each other at some drag bar before that fateful evening in Los Angeles. Naturally it was Dan who had suggested the crew’s visit to the drag bar and it was Dan who had suggested they invite that beautiful karaoke singer to join them at their table.

That brings you up to date. The rest of the story has already been told except……. ‘and they lived happily ever after.’

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Linda Jensen

About the Author ()

Canadian writer Linda Jensen is a long time contributor to TGForum. Before the days of the Internet Linda started her writing with the Transvestian newspaper. Her writing ranges from factual accounts of her adventures to fiction although frankly sometimes her real life adventures are stranger than the fiction. Linda is married to a loving partner who upon learning about Linda said, "she was part of you before I met you. Although I didn't know it she was part of the package I fell in love with. I don't want to mess up that package." "Does it get any better than that?" asks Linda.

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