When a man finds his inner transvestite

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My second floor bedroom was packed with people.  My male friends were prancing around in black, shiny, plastic Basques, laced up the front with red ribbon, suspenders, fishnet stockings and very flimsy underwear.  My girlfriends were dressed in a similar fashion with a few French maid outfits thrown in for good measure.  I looked out the window and saw my elderly neighbours, who lived opposite me, transfixed behind glass watching the proceedings with open mouths.  I was living in Bollington, Cheshire at the time.  Bollington was a beautiful village that had, I found out after I moved there, the dubious title of village with the most pubs in England.  Pub crawls that incorporated all the inns, taverns and hostelries were impossible to complete and usually  participants were a total mess by the time they got half way around.   I speak from experience.

Every New Year’s Eve a large group of us would dress up, divide the village into sectors and commence 4 pub crawls at the same time with the goal of collecting as much money for charity as possible.  We would all then meet up at our favourite local, the Red Lion, and party the rest of the night away.   

One year the boys decided that they would have a theme and donned French maid outfits, created by moi, complete with suspenders and stockings. It went down a storm at the pubs, we collected a lot more money than usual and several of my male friends discovered their inner woman.  Thereafter, they would find any excuse to wear female underwear!   Imagine hairy, bearded, labourers, real ‘men’s men’ wearing feminine underwear, high heels and walking as if someone had just castrated them, and you’ll get the picture.  Not a pretty one mind.     

We decided to run with the popular theme of men in frocks for the New Year charity runs for two reasons.  First to cash in and second, because the boys insisted on costumes that displayed their best attributes framed by a suspender belt and stockings.  My house, conveniently located around the corner from the local, became the creative centre for the creation of fancy dress costumes.  Harem girls, ballet dancers, naughty nun costumes, all with the obligatory accessories, were brought to life in my upstairs living room.        

So when the rocky horror show came to town it was with glee that the boys commissioned wet look corsets.    Final fittings and dress rehearsal took place at home.  It was then I saw the neighbours gawping at the sight of a lot of men in not a lot of clothes and I realised they had a bird’s eye view of the comings and goings on in the house.   

I visualised the newspaper headlines for the next day:-

“HENIOUS VILLAGE HARLOT HOSTS HOT TRANVESTITE PARTY!  TRAUMATISED NEIGHBOURS TREATED FOR SHOCK”.

I decided to teach the peeping toms a lesson.     

“Boys” I called “come and say hello”

Eager to show off, my friends tottered over to the windows in their get up, cooed, blew kisses and waved at the two goggle eyed wrinkleys.   

They waved back! ………….obviously swingers.

5 thoughts on “When a man finds his inner transvestite

  1. I’ve read half-a-dozen of your excellent posts, and looked at your amazing photos of Sri Lanka and Thailand, and I read this one and had to ask myself — where are the photos of your buddies? :) You have great stories and a wonderful blog!

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