Written by Jane

Cross Dressing
2 Jun 2019

I am a happily married guy who has cross dressed in private all my life, my wife (Sue) is an elegant sophisticated lady dresses like mother of the bride to go to the shops.

We live quite a affluent lifestyle and enjoy travelling the UK. I have been a member here for many years always joining the crossdressing chat rooms some cuckolding rooms, I am not at all bi.

For the past 4 years I have regularly chatted with another guy my age in much the same position as me, his wife he tells me nearly always wears a girdle and suspenders rarely in trousers.

Many times we have chatted about meeting up but I have always out it off. Jim (Name changed) he recently suggested we meet one day for a coffee at a café I know, with a view to talking about our experiences our likes dislikes to see how we get on.

I do not have his contact details we converse here and he phones me, and we can have a good chat, about our mothers and experiences in our younger days

Jim dresses but only in lingerie and stockings whereas I dress to impress perhaps the influence of my Sue.

Jim and I are of a similar age and similar ideas, a chat would be great, very tempted to meet him one lunchtime.

He’s told me how he likes to see women dressed very much retro secretary personal assistant

A week, or so back he told me about a relationship he had with a secretary at work she dressed to please him always black satin lace lingerie, black pencil skirt white semi-transparent blouse black stilettoes seamed bronze stocking’s pearls necklace and wristlet deep red lips blue eyes.

I have now searched out the lingerie and top clothes, and last evening had the opportunity to try on. First the suspender belt black quite deep, with 6 drops but with “V’ clips making 12 in all, quite a fiddle to attach and adjust. The Eleganti seamed bronze point heel stockings rolled smoothly up my shaven legs. It all felt great. The black semi see-through lace bra 38c cup felt wonderful and with my c cup silicones adjusted and fixed, the look was coming on. Black lace panties felt soft and relaxing, so different to men’s boxers. The blouse is a crisp white thin cotton shirt style, the black bra clearly visible. The black faux leather knee length pencil skirt completed the look including suspender bumps. Work style 3” heeled black patent shoes blonde coffered wig, deep pink lippy and a touch of eye shadow, string of pearls, done. Looked in the mirror wonderful.

I had an idea but was not convinced it was right but put on a maroon blazer, looked good, buttoned the wrong way but completed the look quite nicely, straight seams taught suspenders.

Just what Jim had suggested,

To meet Jim was still a challenge, but I was likening the idea more and more.

I decided to try out some ideas one was to wear my trousers over my skirt and blouse, the blouse was not much different to a shirt in any case. I pulled the hem of the skirt up to my waist I could now put on my trousers, that made it crutch length trousers fitted over.

Put my boat shoes on, looked good removed silicones chest ok. Should I plan to meet dressed this way. It was easy to install silicones slip off trousers, put on heels, unfold skirt, fit wig, do make up and I would be ready, so exciting but!!

What should I do?