This is a rather old thread but it resonated with my so my two pennyworth………. I spent years in the early part of the century working away and went thru all the same angst and thoughts, could I possibly get past reception unseen, etc. I shudder now at the years of wasted opportunities. The fact is reception is there to see who comes in - you would not really want it any other way - though they may well effect not to see you! Your problem, if you have a problem, is not the hotel staff but any guests that may be hanging around the reception drinking, smoking or just checking in so for me it is just about timing it right and there is a lot of luck in that decision. For the hotel, you are just a paying guest and they are not about to “call you out”, especially in these days of diversity training. So pack the heels and the frock and get out and have fun.

I think that proves my point. Over the years I have noticed that people in retail (shop assistants and sales staff) care less about whether you dress as Arthur or Martha and more about keeping people happy. I have gone into Boots in male mode and asked about make up and even had a colour match with the machine to get the best colour foundation. The staff were excellent and I would go back there for anything else I need. Happy customers come back, and the money is the same whatever your clothes or sexuality! I do remember one "iffy" experience and that was in Salisbury. I had checked into the hotel and got dressed, put on my coat and went for a walk, to get out of the hotel I passed the bar, full of construction contractors and a few outside smoking. I walked around the town for a while then headed back to the hotel, but thankfully most of them were gone to bed or in the bar itself, but nobody said anything or made any comment so I think I was not really noticed that much!

Many years ago I had a training course in London and stayed overnight. Of course I took Sarah's things with me and my usual routine was shower, shave, make up and dress up. I would normally sort out a sandwich or something in the room so I did not have to go out. This one night I was all dressed when I realised I had nothing to eat. I ordered a pizza from Domino's and rang reception to ask them to send the delivery driver up. They refused as it was against company policy for security reasons. I ended up going downstairs to collect it, the staff did not react at all and nobody said anything! On another over night in the same hotel I was all dressed when I realised I had left my laptop in the car, and went out to get it. The hotel was full of construction contractors and a few were outside smoking. I grabbed the laptop and rushed back inside before someone yelled "tranny!", but I am sure one of them smiled at me!

Away on business Esme was a lil p'd off to find I'd left the hotel dressed 2-3 times and gone for a walk mainly in Shrewsbury.. Out of town Travelodge on Bayston Hill and not far just a walk as nowhere really to walk and I'm certain the hotel staff had me labelled a t girl but who cares.. Her fear was someone from work would be any the hotel and spot me.. No hope of that everyone else stayed town centric. Missed a trick maybe going out wearing a mask.. When I dress hopefully next week I'll try a mask on see how I look. It was liberating first time I left the hotel dressed but learnt 4 inch heels aren't as comfortable on concrete as they are on carpet.. Coming back into the hotel to have receptionist say hello a thrill wondering did she read me or not..

Before Covid I only left the house dressed once or twice in over 20 years! However when away on business I managed to leave the hotels a few times, depending on how the entrance was laid out. It got so I used to book hotels after looking at them on Google earth and seeing if the desk and entrance was easy to walk past unseen! One hotel I booked in Liverpool was great you could get in and out without the front desk seeing you, only problem was you had to walk past the bar on the way in and out! I have been out with a mask on but only once.

I think id get away with leaving the house in the night when dark but not in daylight with blinds and curtains open.. Not something we've done but I have thought it may be easier to get away with being out and crossdressed in public with a face mask on but i wouldnt want it smudging my lipstick 🤣💄💋