Flying High Ch 2/4


Flying High
Chapter 2

An hour later Jo returned from her shopping trip with a huge clothes bag and wearing a big grin.

“I asked at reception and the nearest clothes shops are a taxi ride away, but it’s not the end of the world, your luck is in. There are often items left behind in the closets when guests leave. The hotel keep everything for a couple of weeks in case anyone calls back, but dispose of it after that. A lot of it is rubbish and goes straight into the bin, most items are then sent to goodwill thrift shops, but anything decent they keep to help out in situations like yours where guests’ luggage is lost or damaged in transit. I managed to find a few things for you at next to no cost.”

“That sounds like a good job Jo, it looks like you have managed to get enough to keep me going for a few days, not just for this evening, and if you managed to get it all at bargain prices, that is even better.”

“That is the good news. The bad news, which you may not be so happy about when I empty the bag, is that the only things that they had in your size were women’ clothes, we women tend to carry more luggage, even for an overnight stop than men do, and there is a lot more stuff to be left behind. I’ve got you a couple of pairs of trousers, obviously women’s style and fit but not over-the-top, and some fairly neutral shirts, which you should be able to wear without attracting too much attention. I also found a couple of skirts and silk tops to go with them, and a lovely azure satin sheath dress with chiffon sleeves that I though you might like, but if you don’t I’ll have them for myself. The only shoes that they had are obviously women’s with instep straps and thick 3” heels. If you want to dress for dinner you have three options as I see it: wear your uniform and hope that you don’t spill anything on it while you are eating; dress androgynously in ladies trousers, blouse and your loafers; or why not try a night on the pink side and wear the dress or skirt and top.”

“Don’t be silly I would look ridiculous wearing a skirt or dress, no-one would ever believe that I am a woman, we\ll be lucky if we do not get barred from the restaurant. I might it might be best if I just order room service.”

“This is our first night stopover, it should be memorable, I insist that one way or another we go down to the restaurant for dinner, As for not being seen as a woman, you are constantly being called ‘Miss’ on the plane, most people see you as female anyway, and that is without makeup and your hair styled.

I’ll try on the trousers and one of the plain blouses, they may not look too feminine and I think that I can probably get away with that.”

“What do you think Jo?’ I asked a few minutes later as I did a turnaround to give her a full view.

“Not too bad, but to be honest, even with the trousers and blouse you still come across as looking like a woman, but you walk and talk like a man, I think it would be less confusing if you wore a skirt or even the dress, which I think would suit you.”

“ I know that I have been out wearing a jumpsuit and been taken as a woman, but this is a different level I’d never get away with it.”

Let me prove it to you, by giving you a makeover, we have plenty time.”

An hour later after Jo had worked her magic on him Ashley couldn’t believe what he was looking at in the full-length wardrobe mirror. She had managed to tease his hair into a short but feminine style and had given him a dramatic evening makeover.

“There you are Ash,I told you that I could make you convincing. Go and put on the panties and a pair of tights from your emergency pack, wear your new dress and heels and we’ll have a look at the finished article.”

When he came back from changing, he walked in rather sheepishly and embarrassed and went over to the mirror again. Ashley looked stunned, he pictured himself in his new appearance alongside images in his head of Jo, Kathy, Sue, and Sally and if he didn’t know better he couldn’t tell who was the fake.

“From the look on your face Ash it seems that we will be going down to dinner together as two girls, I had better go and get myself sorted I can’t be outshone by you, it would never do. While I am in my room drop your dress top again I have left out one of my bras and some breast forms and the special glue to fix them in place that I found in the store downstairs, why anybody would leave them behind I can’t imagine. If you have problems give me a shout but try to manage it yourself. Ashley fiddled around for a while until he managed to get the bra clasp connected behind his back and slipped in the breast forms. When he zipped up the dress again it now really showed its shape and style in its best light.

When Jo returned looking equally as glamorous as Ash, she handed him a clutch bag matching the dress. “I’ve put a few bits and pieces in there, you might need to touch up your makeup after eating, and don’t forget your money, you are paying tonight girl.”

When they entered the restaurant, Ash nervously looked around to make sure that none of the rest of the crew were there, then followed Jo to a reserved table.

“Good evening Ladies, welcome to the Runway Hotel. Do you wish to order a drink while you are choosing your meal.”

“You choose for a change Ash, you know your wines better than I do.” Jo directed the maitre d’ over to Ashley, with a sweet smile. She was surprised when Ash confidently discussed the wine choices with him before ordering a bottle of Russian River Valley Chardonnay.

“Very good Ash, an excellent choice, but where did the sultry feminine-sounding voice come from?”

“At school I played the lead part of Elizabeth Bennet in a production of Pride and Prejudice, amongst other times acting as a woman or girl, it was a boys’ school you see and because of my size I was always chosen to play female roles. The drama teacher was an ex-professional actor who coached me in voice training to make me even more believable, particularly after my voice broke into the high tenor that it normally is now ”

“He certainly taught you well. I don’t want to embarrass you, but have you ever dressed as a girl apart from the school plays, you play the part so well.”

“If my mum had been allowed her way I would have been wearing a skirt around the house when I was rehearsing for the plays, as she thought it would help me get in character and get used to the feel of a skirt flowing around my legs. With my obsession with aircraft I was already considered a bit of a weirdo anyway, and was often being called all sorts of names for regularly dressing as a girl for the female roles. If it had got out that I was wearing a skirt at home, my life at school would have been unbearable. As it was, I didn’t have any close friends, nobody wanted to be associated with the class geek, and it would only have got worse if anyone found out.”

“But never since then?”

“Not until tonight, unless you count wearing the airline uniform and the jumpsuit around the house, but that is what I am doing this evening, I am just playing a role.”

‘Well enjoy it Ash. For tonight you are my best girlfriend and we are out enjoying our first time in New York, tell me a bit more about yourself.”

Ashley soon relaxed, ignored how he now appeared as a woman, and enjoyed the night in the restaurant chatting to Jo about their colleagues, the airline and life in general, and later they made their way back to their rooms.

“You did really well tonight Ash, nobody picked you out as anything other than an attractive young woman, and you even acted and sounded the part once you slipped into your female voice. We must do it again sometime, I really enjoyed myself being with you was almost like being out with one of the other girls.”

“I had a good time too, but I don’t think that I will make a habit of it. When we first went into the restaurant I was so worried that I would be picked out as a man in dress, but I soon relaxed after discussing the wine with the maitre d’ without any problems. However, after tonight the dress, shoes, and the other things you bought for me will go back into the wardrobe.”

“In that case, fold everything up and I’ll squeeze it into my case., we don’t want any security checks finding a collection of women’s clothes in your luggage, you can have it all back after we clear customs. Then make sure to clean off all your makeup, we don’t want any tell-tale signs left in the morning.”

On the flight home, although Ashley was now back to his normal appearance, his voice kept slipping into the female version that he had been using all the previous evening in the restaurant and was being addressed as another one of the female attendants by all the passengers he dealt with.

True to his word, the meal in New York with Jo was his last outing as a woman, although he did continue to wear the comfortable jump suits at home, along with the cincher to keep his waist nice and trim. His new replacement male uniform soon arrived and his old one was left in the wardrobe as an emergency spare. Although his voice occasionally slipped into female mode, he was now recognised as a male by everyone, but found that he was now treated differently, for some reason a female attendant was treated in a more friendly manner than a male.

A few weeks later as they left after a flight back to base, Jo asked him if he fancied going for a drink as there was something she wanted to talk about with him.

“Ash we’re on an overnight stop tomorrow in Dubai, it’s my birthday and I would like to go out for a celebration meal. Is there any chance that I can coax you into coming out with me dressed like you were in New York, I would really like that as a special birthday present for me?”

“I’d much rather not Jo, sooner or later I will let something slip, and be outed as a cross-dresser, and that is something I want to avoid, particularly in somewhere like Dubai that isn’t one of the more socially liberal states. However, if it means so much to you I’ll do it. As they seem to have permanently paired us together on the crew lists, I spend more time with you than anyone else and you’ve become my best friend, so of course I’ll do it for you. I’ll get myself ready and pack everything when I get home, we will be having an early start.”

Ashley had a busy night, making sure that his body was totally hairless, washing and conditioning his hair so that it would be a bit fuller than normal, and trimming his nails so that they would be ready for applying polish the next evening. When he packed his overnight case he double wrapped all his female clothes and accessories and covered them with his normal male items, the last thing he wanted was a security spot check finding them and asking him to explain why he was carrying female clothes.

After a routine but tiring flight hey arrived at their hotel in Dubai, booked in, made a restaurant reservation and Ashley started to prepare himself. Remembering how Jo had worked on him in New York he did his hair and makeup himself before putting on the satin dress and heels that she had bought him, allowing Jo to get herself ready without having to rush after dealing with him. Finally he had a close inspection of his appearance in the full-length closet mirror. It was not quite as perfect as when Jo had done it for him, but was completely acceptable in turning him once again into an attractive young woman.

The pair of them made their way to the rooftop restaurant, arms linked, to find their table next to a picture window giving a lovely view over the Old Town to the modern high rise developments along the coast and the spectacular Burj Al Arab jutting out into the sea like a boat in full sail. They ordered some wine and were looking at the food menu when they heard someone approach their table. Looking up Ashley was horrified to see Kathy, Sue and Sally, who had been on the training course with them. The last thing he wanted was more people seeing him dressed as he was.

“Hi Jo I’ve not seen you for ages, do you and your friend mind if we join you, we have a lot of catching up to do?” Asked Kathy.

Jo stood up to give the other girls a welcome hug.”Of course, that would be lovely. get the waiter to bring over another table and chairs. Girls this is Ash who I have been working with, Ash meet Sally, Sue, and Kathy.”

Kathy was the first to realise that Ash was Ashley who had been in their group for training.
“Ashley, is that really you, I would never have recognised you if Jo had used a different name. Stating the obvious, you haven’t half changed, you’re looking gorgeous by the way, come and give me a hug, that’s what us girls do when we meet an old friend.”

They were so soon joined by Sally and Sue, with the girls all giggly and excited and Ash wanting to run away and hide. As they were hugging and greeting each other the waiter came over with another table and more chairs, setting the extra places.

“Let’s sit down, all our news is just bits of gossip, but you two obviously have a lot more to tell.”Sally could not take her eyes of Ash, she couldn’t really believe what she was seeing.

Jo asked the girls what they were doing there as she was surprised to see them, they were on the previous days flight and should now be on their way home. While they were waiting for the waiter to finish what he was doing, the questioning of Ash was paused, but quickly resumed after he had left.

“There was a technical problem with the aircraft, nothing serious, it will be fit to go in the morning, but at least it gives us a chance to have a catch up with you both. You first Ash, you have a lot more to tell. When we were in training, you fitted in really well with us, and were almost one of the girls, but I never realised the reason you were so at ease with us. Have you always dressed in women’s clothes, they do suit you? You are not flying as a female are you, we’ve heard that one of the cabin crew is doing that, in full makeup and with his, or maybe that should be her, hair properly styled. Apparently she is really good at her job and the airline tolerate her as long as she comes across totally as a female and does not embarrass the passengers or the company.” Sue answered for them.

“Hold on Sue, one question at a time please. I’ll come back to how it has all happened, but first you must understand that other than stage appearance taking roles as a a girl in school plays, I have never dressed or acted as female until the mix up over our new uniforms. When I wore the female uniform that I had been issued with, I became accustomed to being treated as a female attendant by the passengers, although other than wearing the uniform I didn’t really see why there was any confusion, but just accepted it. One thing led to another and here I am, Ash, wearing a dress, heels and makeup”

“With boobs too, I assume that they are not genuine, and just look at your narrow waistline, I’m jealous.” Sally giggled. “ You can’t stop there, it’s a long way from an incorrect uniform to being dressed up in all your finery for a girls night out.”

Fortunately for Ash, the conversation was interrupted by the waiter bringing over two bottles of Marlborough Sauvignon Blanc, and taking the order for their meals after filling their glasses.

“You are embarrassing Ash so I will take over where she left off.” Jo picked up the story, told them about meeting Ashley when he was out shopping wearing a jumpsuit and loafers and how that put the idea into her head, when his case was lost in New York, to get him to have a night out wearing a dress, the same outfit that Ash was wearing that night.

“You have really fitted into the role, you even talk and gesture just like any of us, I would never have doubted you or recognised you if Kathy hadn’t picked it up first. I love the dress by the way, it really suits you and is a super fit, have you any more clothes with you or at home.”

“Jo bought me a few tops and skirts in new York, but I haven’t worn them since, and this is the only dress that I have.”

“That will never do, wearing the same outfit that you have worn before for a special night out, you’ll have to splash out on some new clothes Ash. Actually I might be able to help you, I’ve been having a clear out of a lot of things that I don’t wear anymore but haven’t had time to put them on EBay or Vinted, It’s all good wearable stuff, it’s just that I have got bored with it. I’ll sort some out that I think will suit you.” Kathy offered.

That started the others off and Ashley was soon in danger of being swamped by promises of more clothes than he was ever likely to wear.

“Thanks ever so much girls, it’s so kind of you, but I don’t know when I will ever get the opportunity to wear it all.”

“Don’t be silly Ash, I’m sure that tonight will not be our last time out together, and a girl never has too many clothes to choose from. Now that we have met up again, how about us all getting together for a regular night out. I know it will be difficult with the shift patterns, but we’ll manage something. Ash when we do meet up I insist that you turn up in women's’ clothes and all made up, from now on you are one of the girls.” Sue suggested, the others all agreeing they would look forward to it.

“That’s enough of that Ash and I were intending this to be a quiet birthday meal for me, but now we’re all together let’s make it a proper girl’s night out, enjoy a decent meal together and have a good gossip.”

The ‘good gossip’ turned out to be which of the other crew members and pilots that they had flings with, including full grading of who was best and who needed a lot more practice, and which of the flight crew were too touchy-feely and pushy and should be avoided. No allowance was made for Ashley being there, as far as they were all concerned, at least for that night, he was one of the girls and nothing was held back about their personal lives and intimate medical problems, much to his surprise. After all the wine they had drunk, Ash needed to use the loo, picked up the clutch bag and was immediately followed by Sally.

Ash fond a spare cubicle, sat down, did what was needed and was getting dressed again when Sally called over the cubicle wall “Ash have you got any tampons or pads, I’m just coming on all of a sudden and I’ve left my bag at the table.”

Ash dug out a pad from her clutch bag, The girls had been referring to him as she and her all through the meal, and with the wine that had been drunk she just accepted it. Jo had insisted just like most other women, she should always have something for an emergency, although she never knew what she had meant. She passed it under the cubicle door to Sally and stood staring at the mirror thinking how far down the path to womanhood she now was, sharing sanitary products with another woman. She was refreshing her lipstick when Sally came out.

“Thanks ever so much Ash. I hope that I didn’t embarrass you by assuming you had period products, I was in a bit of a panic and forgot who you really are, after being in your company all night you are just one of the girls. I’m surprised that you had a pad though, you obviously will never need one. You are lucky, it can be a real nuisance sometimes, the pain, the grouchiness, the bloating, and the mess, even with other girls who all go through the same things it can be embarrassing sometimes. As for the men, they are even worse, every time we are a bit fed up or grumpy, it’s a matter of ‘Are you on now’, as if that is the only thing that upsets us. You have been brilliant the last few minutes, most men are not comfortable thinking or talking about periods and quickly change the subject.”

“Glad to help Sally, are you ok now? We all have our problems but we have to stick together and help each other, don’t we?”

“You’re right Ash, most men seem to be shallow and momentary in their relationships but with us girls it’s a lot deeper. You’ll always be my friend and I hope to see you again. Can I ask another favour, may I borrow your lipstick, my lips need a refresh, yours is almost the same colour as mine, which is in my bag along with my pads and all the other paraphernalia. Thank god for girlfriends to turn to when we need help.” she giggled.

The others had to leave as they had an early flight scheduled. After goodbye hugs and promises to meet up again soon, Jo and Ash sat for a while finishing off the wine.

“That wasn’t too bad was it Ash, you looked horrified when the girls walked over, but they loved you, and once you got over the shock of seeing them you just blended in with the rest of us When we were in training and you latched on to our little group, we were all a bit wary of you, but after a few days, apart from the way you were dressed, you were as much one of the team as the rest of us girls. Today has proved how right we were, I’m not suggesting that you were camp or gay, but you turned out to be a kindred spirit and that was reinforced this evening, you were as much part of the girls night out as the rest of us.”

“You don’t know the full story Jo. When Sally and I were in the loo, she unexpectedly started her period and asked if I had anything I could give her. I had to give her the pad that you had put in my bag, you said that I should away carry something for emergencies, now I know why. That led to a discussion on period pains and problems and the way men treat women, it’s not the sort of conversation that I am used to. Even over dinner some of the intimate little secrets that you all bounced around was a different world to me, women are much more sharing and open about their experiences than men.

“When girls reach their teens there are all sorts of problems, the first period can be a shocker, the longing for breast development and then the constant itching when it is happening, the first crush on a boy which can be extremely painful. For too many the traumas of teenage pregnancy or even worse abortion can leave us scarred, not forgetting the joys of the menopause which are something to look forward to with dread. Sharing and talking through these problems are how us women deal with things, whereas men hold everything back and suffer in silence. You heard the girls, they all want us to meet up again, including you, do you think that you could do all this again? If so, you need to get used to conversations about things like that”

“It’s not something that I was planning, this was intended as a one off, or an encore if you prefer, anything more needs a lot of consideration.

To be continued.



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