I have always been a sissy: I was petticoated as a child, my hair kept long and was required to wear girl's knickers and a petticoat under my kilt on Sundays, which developed into regularly wearing skirts and dresses at home.  However, my fondest memory is of going for a Valentine's weekend to Dubai to celebrate our tenth wedding anniversary.
My wife convinced me to wear my Sunday best to travel, which was a ladies' kilt, under which, as with normal practice, I wore a full satin slip and matching knickers. My dear wife had bought me a lemon satin bra-slip which was underwired - for those of us with excess fat in the breast area it gives a rather feminine look to the chest, with undisguised breast mounds. This was worn with white knee-length socks and normal buckled slip-on shoes and a soft lemon lambs wool top which hid my slip straps if I was careful, and a black ladies shoulder bag.
It's amazing just how little gets noticed by the general public, I got a few knowing looks, but most was only curiosity until I got to the security search. The machine just kept on beeping so I was invited to go over to a security man for a quick body search. With me almost shaking with fear (or anticipation!), his hands went up under my sweater and you could see his eyes get wider as he slid them up the satin material and onto the cups which shaped my rather well developed excess male breasts.

He completely disarmed the situation by asking if I was travelling as a man or a woman, and after I flustered with, "My passport says male, temporarily."

"It's OK sir," came the reply, "I'm sure it was always a mistake."  There was a Nigerian woman next to us who was tickled pink by the whole thing, she having seen the lemon satin as he raised the side of my sweater.
As bad luck would have it, she was on the third seat in the aisle on the other side of my wife, who took the centre seat in the Emirates business class cabin. The next piece of humiliation was the handing out of the complimentary gift sets, which was a feature of Emirates flights (in first and business class) and is so for most of the others. The young lady approached our seats and she pulled out two ladies' complimentary sets handing them to the Nigerian lady and my wife, then was handing me a male gift set when the Nigerian lady grabbed her arm and told her that a ladies gift set would be more appropriate for me. The Stewardess looked at me and asked me if that was indeed my preference. With a red face I, of course, said "yes please".
For those of you who know the flight, it takes almost seven hours; I had to put up with tricks from this woman, including ordering ladies, magazines, a rather feminine cocktail and make-up from duty free, all delivered to me. When my wife went to the toilet she swapped seats into the middle and spent what seemed like hours during dinner regaling us with stories about how difficult life is for effeminate boys and men in her own country and how refreshing it is to travel in Europe and find such tolerance for 'male ladies,' much to the amusement of those around. For those of us who live this way, of course, it can be an occupational hazard to be singled out for humiliation at the hands of others, but on a plane there is no escape from your audience.
Having finally dropped off to sleep, her final trick was to undo the rose clasp pin holding my kilt in place as a skirt and to slightly move the neck line of my sweater. This, according to my wife, who was highly amused by all this, had the joint effect of revealing a satin strap and a few inches of lemon lace. Next thing I know she was asking me to let her out for the toilet, at which time my additional movement revealed my bra-cup and most of the skirt of my slip, while she told me my petti was showing.
I don't suppose most will think it mattered by then - I was very androgynous in appearance anyway, and in essence my femininity exposed prior to this, but I had not yet reached the point in my life where it became second nature to wear feminine clothing in public, even if I rarely wore trousers at home. As we queued to get off she was behind me, deliberately rubbing her hand on my rear and giving it the occasional squeeze.
In comparison, the weekend was event-free.  I got a rather knowing smile from the security lady in her burka, I wore my kilt on a couple of occasions while out without incident, and the only other thing that happened was a trick by my wife by the pool side. I usually wore a ladies' bathing costume because of my prominent breast tissue, with a robe and Birkenstock sandals while I sat and read a book or a magazine. I fell asleep, later to find my robe had been undone revealing my red bathing suit. According to my wife, I attracted very little attention and she pointed out that it should be a lesson to me, that acting naturally, being rather pretty for a male, having long hair, no Adam's apple and having small hands and feet would be my passport to passing at all times. I wasn't quite ready for full femme in public then, so I resisted her suggestion that I should swim, and resisted the suggestion that I should wear lipstick and paint my nails.
When I look back I can laugh at this as part of a rite of passage from sissy to woman, but at the time it was scary, thrilling and dangerous in equal measure, and I suppose I must have loved it. When I got back I found a note with the Nigerian lady's name and telephone number in the side pocket of my cabin bag. telling me how much she would like to get me properly into dresses. I never called her.
My wife brings it up at dinner parties to this day.

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