Fly The Friendly Skies

by Janis Elizabeth

 

Dan couldn't remember when, as a boy, he first became enamored with wearing soft, silky feminine fashions. He knew that, when he was young, he had enjoyed being dressed as a girl by his mom for several years at Halloween. He also knew that he had enjoyed sitting in his mom's room and watching her while she walked around, dressed only in her lingerie. Occasionally, he would touch the satiny slip that she had placed on the bed before putting it on. His mom would see Dan's furtive touching of her clothing and smile at his youthful curiosity. Dan also remembered, before going to bed each night, hugging his Mom while she was wearing a silky nightgown with lots of lace. At those times, he wished that he could wear the same soft clothing against his body.

When Dan was thirteen, he actually tried on some of his mom's panties and slips. He had inherited his mom's body structure, which meant he was short and thin. From the first moment that he felt the satin garments against his body, he was hooked. He didn't want to take it off. However, he did not want to be caught by his mom wearing her lingerie and have to explain to her why he was dressed in her things. On several occasions, he had just barely changed out of her things and replaced them before she would have caught him. Although she never said anything to him about her lingerie being out of place in her drawer, Dan felt that his mom knew of his dressing in her things. Why else would she occasionally leave a lovely nightgown or a new bra and panties set on her bed in plain view if not to allow Dan the possibility of wearing them and thinking he was getting away with something.

It was during his senior year in high school that he finally admitted his secret desire to his mom, and, at the same time, decided on his future career. For several weeks Mom had been asking Dan what he wanted for Christmas. Although he wanted to reply that he wanted soft, feminine lingerie, Dan only replied that anything she got him would be great. One evening, as she looked at a lingerie catalog, she asked Dan to sit beside her on the couch and tell her which of the slips, teddies, camisoles and nightgowns he liked most. Although he had secretly looked at the catalog several times and had imagined himself wearing the lingerie, Dan blushed in embarrassment. He responded noncommittally and said that they all looked nice. His mom pointed to one lovely nightgown, similar to one that she had, and that Dan had worn on many occasions, and asked if that wasn't his favorite. When he didn't answer right away, she looked at him, smiled and said that she wished she could have seen, on those numerous times, how nice Dan had looked when he wore her matching nightgown.

At this comment, Dan blushed even more furiously and tried to deny that he had ever worn or even had an interest in her lingerie. His mom put aside the catalog and hugged him, telling him that she already knew that he wore her things and it was all right with her. He should not feel ashamed about wearing the soft, silky lingerie. As she softly stroked his head, she tried to reassure him that he wasn't doing anything wrong or embarrassing by saying that some men frequently enjoyed wearing silky lingerie and dresses. She said that he didn't need to hide his dressing from her anymore. She was also glad that he wasn't a macho male and was pleased that he could enjoy the feminine side of his being. When he looked at her and asked how she knew, she replied that the nightgowns and bras and panties left on the bed were never put back in the same place or folded in the same manner. It was the same with her lingerie drawer. She could usually tell when Dan had been in it and what he worn on that particular occasion.

At that point, Dan wanted to run and hide, as he felt so mortified at being discovered by his mom. In spite of her calming reassurances, Dan could not bring himself to accept the fact that it was all right with his mom if he wanted to wear her lingerie. Finally, in one last effort to calm him, his mom asked if Dan wouldn't be more comfortable wearing panties, a nightgown, a robe and some fluffy slippers. Dan looked at her and slowly nodded his head.

She stood and helped him stand and led Dan back to her room. She smiled and asked him if he wanted to select the things that he would change into or would he want her to make the selections. Dan quietly replied that he would appreciate it if she made the choices for him. She again assured him that it was all right, while she selected the lingerie for Dan to wear. She handed him the frothy, lacy apparel along with a pair of her fluffy white mules with one-inch heel. Just before Dan went to his room to dress, his mom stopped him when a sudden thought came to her. She went to the bathroom and returned with a fresh sanitary pad. When Dan looked at her strangely, she said that he should wear it properly in his panties. It would heighten his feminine feelings and would provide a means to properly tuck himself in. She asked that he not take too long changing, as she wanted to see how lovely he looked in satin lingerie.

Dan quickly went to his room and laid the clothing on the bed while he undressed. When he was naked, he briefly looked at his slim body. He was glad that the little body hair he had was easily removed b shaving. He first picked up a pair of peach satin panties and slid them up his legs. Remembering his mother's advice, he took the pad and properly positioned it before making sure that the panties were in place. Dan also made sure that he was tucked in properly so that there would not be an unsightly bulge in his panties. He looked at the delicate lace that surrounded each leg opening and felt the softness of the satin against his loins. Next, he put on the matching ankle-length peach satin nightgown. It seemed to float down his body as he put it on. Even though this nightgown wasn't the one that he would he selected, he loved it all the same. He looked at the lace that covered the bodice and then lifted the nightgown to briefly admire the lace at the hem. Lastly, he slid the sheer peach robe over his arms and fastened the single satin closure at the neckline. He slid the mules onto his feet and then took a few seconds to get the feel of the heel. Once satisfied that he could walk without falling on his face, he looked at his reflection in the mirror. He loved the sight of his body dressed in beautiful lingerie. After making sure he looked all right, he returned to his mom's room. He was ecstatic with the feeling of the long nightgown as it swirled around his body as he moved.

Mom had already changed into a lovely long royal blue satin nightie and matching robe that were among Dan's favorites. His mom smiled as he entered her room and said how nice he looked in her lingerie, although his male haircut seemed out of place while he was dressed. She quickly went to her dresser and removed a white satin hair bonnet, which she gave to Dan to put on his head. After it was in place, his mom said that he looked very feminine. "I guess while you are dressed like that, I can't very easily call you Dan," she said. "May I call you Dawn, my new and lovely daughter?" Dawn smiled and nodded as she heard her new name for the first time. Mom then said that they should return to the living room and pick out some lingerie for Dawn to receive as Christmas presents.

As they sat and discussed the various items, Dawn indicated which items, colors and fabrics she liked better than others. At one point, her mom asked her what she would do after graduation from high school. Dawn put down the catalog for a minute and said that she wanted to get into a career that traditionally had attracted women to it. She had already ruled out becoming a hair stylist, nurse or teacher for a variety of reasons. She looked at her mom and said that she wanted to be a flight attendant and had already applied to several of the airlines seeking a position. Dawn knew that she would never get to serve in a woman's uniform. Nevertheless, she knew that she would be as close as possible to being feminine in her job. Her mom smiled as Dawn explained her career choice and was happy for her that she had already taken steps to begin the process.

By the time they finished looking at the catalog, it was time for bed. Dawn asked if she should change out of her mom's lingerie and into her own male things. Mom smiled at her new daughter and said that she could sleep in them tonight and every night thereafter, if she so desired. Dawn reached out and hugged her mom tightly, thanking her for the opportunity to wear the things that she desired to wear. Mom said that it was her pleasure and that she was delighted to have her daughter Dawn around whenever possible.

From then on, Dan would wear lingerie whenever he was home. His mom had selected some of her things to start Dawn off. That Christmas, Dawn received many pieces of soft lingerie for her use, expanding her small wardrobe considerably. As a special gift, Dawn received realistic B-sized breast forms, perfect for her teenage form. Occasionally, her Mom would loan Dawn one of her dresses or a skirt and blouse set. However, Dawn never ventured out into the world. She was content to merely to stay at home and experience her feminine side. The night of the high school senior prom, under his tuxedo, Dan did wear a pair of white satin panties with his Mom's approval. His date would have been surprised had she known it.

After he got home, Dan described his date's satin gown and wished that there had been some way that he could have worn it or one similar to it. His mom understood his desire and went to her closet where she retrieved one of her satin gowns. She asked if Dawn would like to try it on and model it for her. Eagerly, Dan nodded his head. He took the gown and went to change. After removing his male clothing, Dawn put on a bra and made sure she inserted her breast forms. Next she put on her garter belt and placed the garter tabs on the inside of her panties. After drawing stockings up her legs, Dawn put on a long lacy full slip. At that point, Mom came in and handed her a pair of three-inch heels to wear with the gown. Dawn smiled appreciatively and slipped them onto her feet. Mom then helped Dawn into the gown. It was a sleeveless red satin gown with a rounded neckline and the full skirt flowing from the fitted waist. Dawn loved how it looked and fit. Mom then helped her into elbow length satin gloves. After she was dressed, Dawn said how nice the gown looked on her. She wished that she could have worn it to the prom. Her mom smiled as she watched her daughter enjoy the dressy satin garment.

At graduation, Dan again wore white satin panties under his male attire as well as the needed maxi pad. In this way, he felt feminine even when he was dressed in his male clothes and the dark cap and gown. He secretly wished that he could have worn the white cap and gown like the girls did but he knew this wasn't possible.

After graduation, Dan attended the flight attendant's schooling for one of the country's leading airlines. He learned all about serving passengers meals and beverages during flight, how to deal with in-flight medical crises and what to do to assist the passengers during any possible flight emergency. However, while the female students attended classes on hair care, fragrance and makeup, Dan went with the few male trainees to the classes on proper male grooming. He wished that he could be a part of the lessons on how to keep one's hair and makeup looking fresh throughout a long flight. Also, during the sessions dealing with the uniforms, while the other men sat with uninterested expressions on their faces, he sat envying the women as he listened to them addressed proper use of the scarf with the uniform, maximum heel height allowed and other items specific to the wearing of the women's uniform.

Nevertheless, Dan successfully completed the course and was hired as a flight attendant. He soon was part of a regular crew with three women. He loved working with Pam, Lisa and Laura in a job that had a great percentage of women in it. With the nature of the uniform, Dan took to wearing a garter belt, panties with proper maxi pad and stockings under his male attire. Sometimes he even wore a camisole to complement his panties, although he felt that wearing a bra would be too noticeable. In this way, he felt more feminine with his female crewmates without actually appearing dressed in public. He felt that, since nothing was visible, there was nothing that could possibly reveal his secret to others.

Dan had endeared himself to his crewmates, as he was always doing extra duty to help serve the passengers or to get the plane prepared during layovers. He was very pleasant as he greeted and served the passengers in the cabin. During one of the flights, as Dan was bending over the service cart to retrieve a beverage from the other side, Laura happened to be coming out of the galley behind him. She noticed what appeared to be the outline of the garters and the garter belt and the visible panty lines as the fabric of Dan's trousers was tight against his legs. She smiled at the discovery and appreciated Dan for the fact the he liked to wear lingerie. However, she kept the information to herself, as she did not want to confront Dan and cause him any embarrassment.

He had moved to his own apartment and had continued to wear his lingerie whenever he was at home. However, even though he tried to be discrete, especially when he had company, he did have a lapse that could have revealed his secret. One evening, the women had stopped by for a brief visit and to go over some new company regulations. During the evening, Lisa excused herself and went to the bathroom. Although Dan thought everything was properly hidden, he had forgotten that his pink plastic shower cap was hanging over the towel bar. Lisa saw this and thought that it was strange that Dan would have a shower cap, especially a pink one. To confirm or refute her suspicions, Lisa looked in the laundry hamper. In there, she noticed several pairs of lovely panties, waiting to be washed. However, she did not mention this to Dan or the others when she rejoined them in the living room. She felt he was an excellent crewmate and if wearing women's clothing was his turn-on, she was not going to embarrass him by mentioning what she had found.

Even Pam had seen something as she and Dan were talking in the galley during one lull in a flight. The lighting fell on Dan's uniform shirt in such a way that it revealed the evidence of the lacy straps of Dan's white satin camisole. She also kept this knowledge to herself as she valued Dan's service as a crewmember and didn't want to embarrass him. Six months after the initial discovery by Laura, the three women happened to be together over lunch without Dan. As that talked about Dan, they mentioned about his hard work, his pleasant personality and his kind and gentle manner. In passing, Laura mentioned that she had seen something one time that just didn't seem right. When pressed for details by Pam and Lisa, she spoke about the occurrence when she had seen the outline of the garter belt and panties under Dan's uniform trousers. She was about to say that she must have been mistaken in what she saw when Lisa mentioned about finding the pink shower cap in Dan's bathroom and the panties in the hamper. Pam then mentioned seeing what appeared to be a camisole under his uniform shirt. Lisa also mentioned that, when they were back in the galley, she thought she heard the faint rustle of plastic, like that on the back of a sanitary pad when Dan moved. At the time she simply dismissed it, thinking her mind was playing tricks on her. It seemed evident to his crewmates, when these observations were taken together, that Dan was one of those special people who enjoyed wearing feminine things.

After some quiet discussion, they agreed that there was only one way to really find out. Laura said she would get the uniform and lingerie. Lisa volunteered to bring a wig. Pam offered to do the makeup and provide their friend with heels. It was agreed that, since Dan was off temporarily filling in on another crew, they would wait until his return to address this. Pam, as the crew leader would call Dan and have him arrive very early for a morning flight. Her excuse would be a new federal procedure that Dan had to be trained in. They would then see what happened when they asked Dan about what they had observed.

Three days later, Dan was set to rejoin his crewmates the next morning on an early flight. He was in his apartment, dressed in white satin bra, matching panties and a waltz-length mint green satin nightgown with a nylon overlay, when he got Pam's call asking if he could be extra early for the flight, as he needed to learn a new procedure. Reluctantly, Dan said he would be there and would meet the crew on the plane. After talking to Pam, Dan decided to get to bed early. Putting on a white satin sleep bonnet, he climbed between his satin sheets and quickly fell asleep. That night, all of his dreams seemed to center on him being dressed in various feminine outfits while out in public. When he awoke in the morning, he felt very refreshed, but could not understand what his dreams were supposed to mean.

Dan quickly showered, dressed in his uniform with his lingerie hidden underneath, picked up his carryon bag and headed for the airport. He arrived at the gate and found someone from the airline waiting for him to allow him to enter the plane. Pam had already made arrangements to have them all allowed to board well before they were scheduled.

When he entered the cabin, Dan saw Pam, Lisa and Laura already sitting in the first class seats waiting for him. Pam asked him to leave his bag by the door and to come join them. As Dan sat in an empty seat, Pam looked at him and said that before anyone did or said anything that might embarrass or hurt Dan, she wanted to ask him some questions. Dan was perplexed at what Pam said but was agreeable. Pam proceeded to tell Dan what each of them had observed on different occasions. Dan sat, blushing, with his head in his hands, as he heard all of this. He thought he had been so careful. In his mind, he was already preparing his response to say that he would seek a transfer to another crew if they so desired. Finally Pam looked at Dan, gently lifted his head to look at her and said, "Dan, we are all deeply fond of you as a crewmate and as a person. We wouldn't do anything to hurt or embarrass you. However, we would like to help you if the situation is, as we all perceive it. Do you enjoy wearing women's clothing? Have you worn lingerie under your uniform?"

Dan again hung his head in an embarrassed way and softly said, "Yes." He started to say that he would request a transfer to another crew if any of the three of them could no longer stand to work with him since he had revealed this deep, dark secret. Before he could finish his statement, however, all three of the women moved toward him with first Pam and then Lisa and Laura giving him a big hug. Pam said that the last thing that they wanted was to have him transfer. Lisa smiled at Dan and asked if he would want to serve as the fourth female member of the crew during today's flight. Dan looked up at her with joy and said that it would fulfill his fantasy if he could serve as a female flight attendant.

Pam then said that they had hoped he would be agreeable, as they had brought everything that would be needed to affect the transformation. However, before they began, she asked if Dan had a feminine name or did they have to come up with one. Dan nodded quietly and said his Mom had named him Dawn, when she found out that she had a part-time daughter. All the women agreed that it was a lovely name. Pam looked at Dawn and smiled, saying she had made a lucky guess. She produced a standard airline nametag with Dawn's first name on it.

Lisa and Laura lowered the shades in the cabin while Pam took charge of Operation Dawn. She had Dawn undress in the cabin while she made sure the door to the aircraft was secure. When Dawn was clad only in her garter belt, stockings and panties, she stood shyly before her crewmates. Laura told her not to be embarrassed standing there in her lingerie. A smile played across Dawn's face as her crewmates admired her lovely lingerie and complimented her on her tastes. When Laura noticed the bulge in Dawn's panties, she looked questioningly at her. Dawn smiled and said she wore a maxi pad all of the time both to give her a feminine front and to keep properly tucked in. She then took some good-natured kidding from her crewmates about having her monthly time today.

Dawn had worn black stockings this morning, which were acceptable with the regulation uniform. Pam had Dawn remove her camisole and then handed her a white satin bra. As Dawn fastened the hooks in the back, Pam was inserting C-sized breast forms into the cups. Dawn then made minor adjustments to the straps and to the position of the bra. She smiled as she gazed down at her feminine form. Laura handed Dawn a lacy white full satin slip, which would fall to just above her knee. She watched as Dawn eagerly slid the lovely garment over her body.

Next came the light blue satin, long sleeve uniform blouse. Dawn smiled again as Lisa buttoned the back. Pam helped Dawn into her knee-length straight skirt and then offered the three-inch heels to Dawn. As she slid them onto her feet, Dawn felt that she was really becoming a feminine part of the crew, at least for today. The women were pleased to see how easily Dawn moved in the heels, evidence of many hours spent walking in them at home.

Pam had Dawn sit in one of the first class seats and covered her with a pink plastic cape. Quickly and carefully she did Dawn's makeup. Dawn sat there savoring the smells of the cosmetics being applied to her face. From the foundation and powder to the blush, eye shadow and mascara, Dawn was truly enjoying the experience. Finally, Pam applied the creamy red lipstick to Dawn's lips. As she blotted the excess off, Dawn almost swooned from the joy and excitement of the moment. After the plastic cape was removed, Lisa fit the wig on Dawn's head. It was slightly lighter than Dawn's normal color, but it looked great on her. After brushing the wig a little to give it an outward flip, Lisa put gold rose clip-on earrings on Dawn's ears. Laura stepped forward and tied a satin uniform scarf smartly around Dawn's neck and then sprayed her with a lovely feminine perfume.

As Dawn stood up, Lisa helped her into her jacket with her feminine nametag. Pam said that there was also an apron in the galley for Dawn once they begin their cabin service. Dawn smiled at her three crewmates and gently hugged each one and thanked them for giving her this chance to be a female flight attendant. The women all told her that it was their pleasure to do this and they hoped she enjoyed her flight. They led Dawn to the lavatory so she could see her image in the mirror. Lisa told Dawn that she made a very attractive flight attendant, causing Dawn to blush.

It wasn't long before passengers started to board. Dawn stood near the back of the cabin and assisted those in coach with finding their seats and stowing their carryon bags. Once the cabin was secure, and the plane started to taxi, Dawn sat in the rear-facing jump seat in the back next to Lisa. Pam was on the speaker system welcoming the passengers to the flight and saying that the cabin crew of Laura, Lisa and Dawn would be pleased to serve them today. Lisa had reached out and was holding Dawn's hand during the announcement. She smiled sweetly at Dawn and said that they had to make sure she had her nails done properly before the next flight. Dawn smiled as she heard Lisa mention the next flight.

Once airborne, Dawn performed her normal flight attendant's duties, only this time she was in a skirt and heels instead of her normal attire. After serving all of the passengers their snacks and beverages, Dawn returned to the back of the plane to help Lisa secure the serving carts. As Dawn was bending over stowing one of the carts, she felt Lisa's hand gently caressing her bottom. This sent a very pleasant sensation through her. Lisa smiled at Dawn and told her that, while she was very fond of her as Dan, she was surprised at how much the transition into Dawn had affected her. Lisa whispered to Dawn that she was very turned on by having her former male crewmate in a skirt, lingerie and heels and she hoped that Dawn would was equally turned on by her new attire and by Lisa. Dawn looked at her and smiled while nodding her head.

While surprised at this admission, Dawn had long loved Lisa from afar. She was afraid, though, that had she started becoming closer to Lisa through dating, her secret might have inadvertently slipped out, possibly alienating Lisa and perhaps even the rest of the crew. Now, here was Lisa admitting her own interest in the femininely attired Dawn. This was after all that the three women had made possible for her today.

When everything was stowed, Dawn and Lisa sat in the jump seats and chatted until it was time to make the final walk-through of the plane before landing. Lisa smiled as she watched Dawn gracefully moved forward on her heels, her hips gently swaying as she walked. Standing near the front of the plane, Pam and Laura smiled as they watched how poised Dawn was as she made her way down the aisle. Had they not known that this was Dawn's first day in public in a skirt and heels, they would have sworn that she had been doing it all her life.

After the cabin had been checked, the flight attendants sat in their respective jump seats as the plane made its final approach for landing. Lisa and Dawn sat in the back and held hands until it landed. As the plane taxied to the terminal, Pam was again making the announcement welcoming the passengers to the city. She said that her crew of Laura, Lisa and Dawn had been pleased to serve them today. She concluded her message by thanking the passengers for traveling with them today and by saying that she hoped their future travel plans would be made on this airline.

When the passengers had departed, the women walked through the plane making sure everything was clean and orderly. They stowed the pillows and blankets that had been used and replaced the magazines in the rack. As they gathered their suitcases Pam looked at Dawn and said that she was welcome to fly with them any time she wanted. Dawn thanked Pam, Laura and Lisa for their kindness and help in becoming Dawn. She told them how thrilled she had been to work as a female flight attendant today. Dawn then smiled shyly and said that, for now, she might only have a very limited flight schedule as she had to build up her feminine wardrobe, especially her uniforms.

At that point, Pam smiled broadly and admitted that a friend of hers was retiring and wanted to give away all of her uniforms. She looked at Dawn and said that they would fit her if she were interested in obtaining them. Dawn said she would be like to obtain all of them, except for the women's uniform pants and thanked Pam for mentioning it. She smiled and said she only wanted to be in skirts

Since they had an evening layover in the city, they planned on going out to dinner. Dawn started to object, by saying she couldn't very easily wear her uniform and she had nothing else to wear. Lisa quickly quieted her by saying that she had planned on this expected outcome and had an extra dress in her bag that would fit Dawn. This was almost too much to expect. Dawn wanted to hug Lisa right there, but felt a sense of propriety. Pam asked how they were going to spend some of time. Lisa smiled and said that she wanted to take Dawn shopping for a lovely negligee, just in case this amounted to anything. It took a few seconds for Dawn to grasp Lisa's intent. When she did though, she blushed furiously, while smiling appreciatively at Lisa.

Before they left the plane, Pam had one more item for Dawn. It was a nice black purse, carried over the shoulder, which went with the uniform. She had also placed makeup, tissues and a wallet in the purse. Dawn thought it was a fine addition and placed it over her shoulder to the nods of her friends. The women laughed and chatted as they left the plane. Pam smiled knowingly at Dawn and said that very little in her carryon would probably be worn. Dawn smiled back and said that she was probably correct. Arriving at the crew hotel, they checked in. Dawn agreed to share a room with Lisa. Pam told the clerk that there had been a temporary change in the crew and that Dan's reservation should be canceled.

After checking in, the crew met in the lobby. The hotel courtesy bus took them to a nearby mall where they visited the lingerie center. Dawn found a lovely two-piece negligee that she absolutely adored. She showed it to her friends and asked their opinion. The nightgown was form fitting, ankle length pink satin creation that was made very feminine with lace all over. The sheer pink robe enhanced the gown. All of the women raved over it. Lisa smiled and said this was her birthday gift to Dawn, because today was her first birthday. Dawn smiled at this. Laura proceeded to get Dawn several pairs of lovely, lacy, satin panties as her added gift. Pam selected a white satin slip for Dawn. Needless to say, Dawn felt like she was in heaven.

On the way back to the hotel, all Dawn could think about was being with her friends at dinner in a lovely dress and then wearing her new negligee for Lisa. Dawn sighed contentedly. Could it get any better than this? She didn't think so.

 

 

 

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© 2002 by Janis Elizabeth. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.