Becoming Cabin Crew

by Becky Huntingdon

  Becoming Cabin Crew:

  Feminized for a VIP

  © 2019 Becky Huntingdon

  All rights reserved. No portion of this book may be reproduced in any form without permission from the publisher, except as permitted by U.S. copyright law. For permissions contact:

  beckyhuntingdon@gmail.com

  This is a work of fiction. All characters, events and places are a work of the author’s imagination. Any resemblance to people, places or events is entirely coincidental.

  www.BeckyHuntingdon.com

  Sean had always wanted to work on a plane. From a young age, he’d enjoyed the idea of this huge piece of metal flying in the sky. He’d made it his ambition to become a pilot. However, for one reason or another, he’d never made it to flight school. He was 21 and had decided to become a member of the cabin crew instead. He would still get to travel around the world and be on a plane every day even though the salary wasn’t as impressive.

  At just under six feet tall, he was a good size and was in great shape through college sports. He had done a little modeling work before and was a hit with the women, something he thought would give him an edge. However, there were a few problems.

  He didn’t realize how competitive the world of cabin crew was. So many attractive people fought for just a few positions. Women also had the edge at this job. Finally, although he spoke a couple of languages he found most other applicants poke more.

  Sean was pretty close to giving up on the dream when he received an offer from a company that offered out cabin crew on a temporary basis. He’d wanted to work for one of the big airlines but he thought that after a few month's experience he would be in a better place.

  His first few positions were at airlines where staff were on strike or there was a sudden demand for extra flights. These were pretty interesting for Sean and he traveled a lot. However, the best job he got was when he was asked to work on a private jet for a client who was traveling from Los Angeles to London…

  They Want What?

  Sean knew the company provided cabin crew for private jets. However, the staff who got these jobs were normally more experienced as the demands were high. VIP customers often demanded a lot, however, they also gave amazing tips. So when Sean was initially invited in to talk about one potential opportunity he was keen.

  “So Sean,” began Mary, the company placement officer, “I know I said that we’ve got a potential place for you on a private jet but I wanted to talk with you about it face to face as it’s a little strange the request.”

  Sean was eager to find out more, “Sure it sounds like a great chance for me, what do you mean strange though?”

  “Well, the customer is quite picky about who gets to work on his jet. He’s looking for an all female crew”

  “Well why are we talking then?” asked Sean, a little pissed off that he’d taken time on his day off to come to the office when he obviously didn’t meet the requirements for the job.

  “I should be clearer he wants women who are actually men...” said Mary, looking a little embarrassed.

  “Wait, let me get this straight, he wants men to dress up as female cabin crew?”

  “Yea”

  “That’s pretty fucked,” said Sean

  “I know, and we wouldn’t normally entertain this kind of request but he is offering a load of cash,” said Mary as she showed a piece of paper with a number on which left Sean speechless.

  “That’s what I’ll get for one flight to London?” asked Sean, not sure what to think with the offer of enough cash to last years on the table.

  “Yes” said Mary, talking more confidently now that Sean was interested, “and you’ll get a first-class flight back if the customer is happy with your service”

  Sean sat there for a minute with thoughts flying through his mind. That money would be life-changing, but the whole experience would be embarrassing.

  “This trip will be confidential” said Mary, obviously reading Sean’s mind. “Nobody will find out what you did”

  “No photos, no video, no jokes?” asked Sean.

  “Completely off the books” said Mary.

  “And that’s really what I’ll get paid?” asked Sean

  “100%” replied Mary.

  “When does the flight leave?” asked Sean.

  “Friday, but you’ll need to arrive on Thursday at the hotel as there are some thin to prepare there before flying,” said Mary.

  “I’ll be there” said Sean as he stood up. He couldn’t believe that he would soon make more in one flight than he could in ten years. Sure it might be weird to dress up as a woman but for that money he was willing. What he didn’t know was that the trans-Atlantic flight would be life-changing in ways other than financial.

  At The Hotel

  The hotel next to the private airport where they’d be flying from was five-star. It catered to VIPs and celebrities who wanted to fly out of LA without having to use the same facilities as ‘normal’ folk.

  Sean was given a keycard and headed to his room, a fancy suite. He hadn’t stayed anywhere like this before, it probably cost well over $1,000 a night. There was a note on the bed saying that the client’s PA would be coming over later to talk through things.

  Sean sat on the bed and flicked through the TV channels finding something good to watch. After around an hour, there was a knock on the door and he opened it to see an attractive looking blonde.

  “Hi,” she said, smiling at Sea, “I’m Chloe, the PA” she said, sticking out a hand to shake.

  “Hey Chloe, Sean” he replied taking her hand.

  He invited her in and they took a seat on the sofa.

  “So, we’ve got quite a lot to get through before tomorrow but first I just want to say thanks for taking this job, my client really appreciates it and we’ll respect your privacy as requested.”

  “No problems, who is your boss?” Sean asked.

  “He prefers to stay anonymous, you’ll see him tomorrow but he’s a good guy, always kind and thoughtful. He just really values his privacy” said Chloe.

  ‘Ah I see”

  “Anyway Sean we have a lot to do, we need to get your new uniform fitted and a few other bits and pieces. I’m going to send on of our team in and she’ll look after you, OK?”

  “Oh, OK sure no problems” said Sean, knowing that he’d probably had to have a fitting and get ready to be a female cabin crew. He just hoped it wouldn’t take too long as there was a baseball game starting in an hour he wanted to watch.

  Right on cue, there was a knock at the door and another woman walked in with a couple of suitcases.

  “This is Amy” Chloe said

  Amy and Sean exchanged pleasantries before Chloe excused herself from the room as she had something else to do.

  “So Sean,” began Amy, “Don’t be shy, I’m going to keep this all secret but my boss has some things that he asked us to do tonight before your flight tomorrow, nothing too scary I promise you!”

  “Sure…” said Sean, not knowing how to react.

  Amy started to open the suitcase and pulled out several small bags. It couldn’t be his uniform though Sean.

  “So tonight we will do some preparation work and I’ll come back in the morning to do your final makeover!”

  Amy pulled a tape measure out of one of the small bags and began taking Sean’s measurements. He had gone through this when getting his first uniform but there were obviously different requirements for his female attire. Amy also measured his feet and head for the shoes and hat he would need.

  After this Amy got out a nail file,

  “Take off your shoes and socks, we need to get your nails perfect and painted” she said.

  This was it thought Sean, the point
of no return. Getting feminized was scary for him and he wasn’t sure how he would take it. However, this baby step of getting his nails done might just ease him into it.

  He looked down as Amy began working across his fingers and toes, making each one perfect. She then reached into her bag and got pink nail polish out. It was strange to see his nails looking so bright. Sean sat in near silence as his heart beat faster and faster.

  “Take your jeans off” ordered Amy, “we need to wax you”.

  Again, Sean wasn’t sure about doing this but every time doubt came to his mind he thought about the bank account balance he would have on his return to LA.

  The actual waxing hurt like crazy. Perhaps it was because were so hairy but he didn’t want to go through the experience anytime soon. However, the result was pretty stunning. His legs looked so smooth and the rest of his body was soon hairless, he only hoped it would grow back before he next hit the beach with his friends.

  “Alright, we’re nearly done for tonight” said Amy “I just need you to put on this face mask before you go to bed tonight and try not to bite your nails!” she warned.

  Sean said goodnight to her and went to the bathroom to put on the various lotions he’d been given to keep his legs moisturized and smooth. After that, he went back to bed and flicked the TV on. He couldn’t believe how different the sheets felt on his smooth body, it was sexually exciting. He was soon jerking off before he fell asleep.

  His alarm at six am the following morning was coupled with a knocking on the door. It was about to be the beginning of his feminization. Sean took a deep breath and got up from the bed.

  Becoming a Stewardess

  Amy was at the door with a team of three other women. Sean was a little surprised as he stood there wrapped in a hotel gown.

  “Good morning,” said Amy, “let’s get going, with got a lot to do and not much time!”

  The four women brushed past Sean and began to set-up in the living room area of the suite. They were carrying suitcases, makeup bags and a suit holder that must have his new uniform. The sight was making Sean feel a little stressed out. He closed his eyes - ‘Think of the money’ he said to himself.

  Sean walked to the sofa and sat down. He took a croissant from the table and began eating as Amy talked him through what would happen.

  First they would do a final body check after that try his new uniform on, finally, there would be hair and makeup. The whole situation was a little surreal for Sean and in all honesty he was keen to just get it over and done with.

  The three women walked around him checking his nails and skin for any imperfections. Occasionally they would find something and use tweezers to get rid of stray hairs. Sean felt that this was over the top, it also made him question who the passenger was. They must have a serious amount of cash and a strange fetish for seeing guys dressed like women. It was going to be awkward to meet the VIP for sure.

  After around twenty minutes it seemed the women were satisfied with his body. One of them walked over to the suit carrier and unzipped it to reveal a cabin crew dress. It looked quite small Sean initially thought, however, they had taken his measurements so he guessed it would fit.

  “Go in there, take a shower and put these on” said Amy as she threw him a bag.

  Sean was a little puzzled bet went into the bathroom and unzipped the bag. It was a lingerie set. There were stockings, suspenders, french knickers and a matching lacy bra. It looked like a really high end set, something he had never seen before. He ran his fingers over the material and was surprised at how light and soft it felt.

  After a quick shower, he dried off his body and looked in the mirror, shaking his head at what he was about to do. He connected the stockings and suspenders and slowly pulled the french knickers on. The soft sensation of the material was unreal on his smooth legs. He felt chills run through his body. When the whole set was on he looked in the mirror and was amazed at how they enhanced his body. The look was incredible, if he didn’t see his face he could have sworn there was a sexy woman in the bathroom with him.

  As he walked out the women in the room were smiling.

  “Yes he’ll like that” said one of the assistants.

  “Who will like it?” asked Sean

  “Your passenger” said Amy, “Let’s just fix a few things”

  The women pulled the bra tighter to create a small amount of cleavage and adjusted the panties to keep his cock flat against the material.

  One of the women walked over with the dress. It certainly would only just cover his panties thought Sean, it would also huge his figure.

  The women helped him into the dress and zipped it up for him. The moment the zip locked the dress in place Sean felt electricity run through his body. He quickly looked in the mirror, eager to see how it looked on him. He couldn’t believe how well it suited his figure. He found himself quite enjoying how he was being slowly transformed into a beautiful stewardess.

  He ran his hands down his body and loved the way his painted fingers complemented the color of the dress. He loved how he knew there was a sexy set of lingerie hidden just under his dress. He loved how the dress dropped enough at the front to show the cleavage that had been created for him.

  “Let’s do my makeup now!” Sean said excitedly

  The women laughed together, “I’m glad you’re getting into this, your passenger will be pleased!” said Amy.

  Sean sat down on the sofa as the women began taking brushed and creams to his face. They tried a number of different foundations against his face before choosing one and lightly applying it. They spent a long time on his eyes. First, they added false lashes, that was followed by thick eyeliner and finally gloomy eye shadow. Sean sat still as they added lip-gloss and a few other items of cosmetics to his face.

  “Let’s get his wig on first to check everything is alright” said Amy.

  One of the women walked over with a medium length brown wig. They spent a good few minutes getting it in place before fastening it to his head. Sean moved his head from side to side and was pleased to feel no movement from the wig.

  One of the assistants walked up to him with perfume and sprayed it to give him a feminine scent. Sean was bursting to see the results in the mirror.

  He let out an audible gasp and brought his hands to his chest as he saw the beautiful woman staring back at him.

  “That’s unbelievable,” he said, staring at himself still.

  “We are pretty good!” joked one of the assistants

  The heels they had prepared took a little while for Sean to get used to. He’d never worn heels before and almost fell over on his first step. However, with a little assistance, he was soon walking around the room. The assistants even helped him to walk in a more feminine way. Sean loved this girly style, he thought he might have to try this again someday!

  “So the last thing we need to do is to put on your name badge” said Amy, “From now on your name is Sara, OK”

  Sean nodded and smiled as Amy pinned his name tag on. His transformation to a woman was complete, Sara was ready to serve her passenger.

  Welcome On Board Sir

  Sara walked out of her room and headed out to the hanger where the private jet was. What she wasn’t expecting was that she was joined in the hanger by another hot stewardess.

  “Sara, this is Clara, she’ll be working with you on the flight” said Amy

  “Nice to meet you Sara,” said Clara in a voice that obviously meant she was another sissy flight attendant.

  “You too” said Sara, smiling at the prospect of not being alone on the flight.

  Amy left the two ladies to talk as she went onboard to prepare things for her boss.

  “Don’t worry about this,” said Clara, “I’ve done this before, we’re going to have so much fun!”

  Sara looked at Clara and felt confusion. This was obviously another feminized guy but Sara found herself really attracted to Clara, she was incredibly hot. Sara shook her head to try and get the naughty thou
ght in her head away and joined Clara in the plane.

  The private jet was luxurious. There were several standard seats in the front and a door which led to a private suite in the rear complete with bedroom, study, bathroom, and a kitchen area. The flight was 11 hours long and Sara was keen to explore all of the plane if possible.

  Sara knew she wasn’t just there to be a pretty face and worked with Clara to do the last-minute safety checks. The pilot got on and greeted Clara before introducing himself to Sara,

  “Have a fun flight and let me know if you need anything” he said before getting into the cockpit.

  Amy walked up the stairs just as a limousine pulled up next to the jet,

  “He’s here, get ready to greet him and then wheels up in ten minutes”

  Sara stood next to Clara and felt herself shaking. Clara obviously noticed this and squeezed Sara’s hand,

  “It’ll be fine hun, don’t worry I‘m here with you”

  Sara took a deep breath and composed herself. With a smile on her face, she peered out of the door keen to get her first glimpse of the secretive VIP she would be servicing. She heard the sounds of doors opening and closing and a deep voice greeting Amy. The sound of footsteps on the stairs meant this was the moment.

  The man entered the plane and Sara’s jaw dropped. He’d walked in totally naked!

  “Nice to see you again” Clara smiled at the man before embracing him.

  “You too Clara, I’m glad you could make it today”

  “I want you to meet my fellow cabin crew for today,” said Clara, “this is Sara. Sara, this is Dean.”

  “Pleased to meet you Sara” said Dean as he leaned in to hug her.

  “And you too Sir” said Sara as their bodies touched.

  She noticed straight away that his body was firm and his cock was hard too! She looked down and saw a huge dick standing to attention.

  “Oh I’m sorry, I hope you don’t mind” said Dean with a smile.