A Letter to Louisa

Over the past few months, I've grown close to a workmate Louisa who's just split up with her emotionally abusive long time boyfriend and needed someone to talk to. We've really hit it off and have spent time at the cinema, theatre, and visited quite a few pubs along the way. I really like her and she likes me - but this is not the start of some burgeoning relationship as we really just enjoy each other company.

One of her favourite films is Rocky Horror and we often play the soundtrack if she's visiting my place, sipping drinks, and dancing around my living room to all of the memorable songs from the production. During one evening she said she'd never seen the stage play but would love to go see it all dressed up and wondered if I would do the same? My heart skipped a beat and I confessed that I had always wanted to do that and I'd be very glad to acccompany her to the theatre the next time it toured the country.

After that my mind was working overdrive imagining myself being dressed by her and then taken into a public place by her side. She's an extremely good looking woman in her mid 40s, slim, shoulder length blonde hair and an amzing set of legs on her!. I decided that the thought of that simply couldn't wait until the next Rocky Horror tour and that I would try my utmost to make my fantasy happen sooner rather than later.  

That night I sat down and composed a letter for her that I would give to her on our next evening together. I had it all planned for the next Saturday night we'd planned a get together.

We'd have few drinks,the music would be turned up, and her favourite CD would begin to play. I'd tell her that I'd something to tell her and that it was quite personal and instead of getting my words all wrong and appearing silly I'd had the foreisght to print out a small letter for her to read that would explain everything to her.

Dear Louisa,

This was a difficult letter for me to write, not because of what it contains and who I am handing it to, but simply because it’s the first time I have been so honest with someone that I count on as a wonderfully supportive friend. I class you as a friend of such importance that I wish to tell you something that I’ve never told any other of my friends simply because I’m not sure how they would handle it. However, I simply don’t have the same worries with you. I won’t drag out this any longer as I would rather you knew as soon as possible, instead of wondering what on earth I’m wanting to tell you, so here I go….  On one of the first nights we went out together I mentioned that I am in touch with my feminine side and that is something that I’ve been aware of all my life. Probably from around the age of 8, I discovered a new side to myself. Since then, I have regularly enjoyed dressing in women’s clothing and spending time dressed as a female. It’s something that I discovered quite early on in my life and it’s stuck with me throughout the years despite numerous attempts to stop and resume a “normal” life. There are various words and slang for my lifestyle, but the one I’m most happy and secure with is transvestite. In the words of the song, I truly am just a sweet transvestite!

However, I must emphasise that I don’t want to change sex, I don’t want to lose any of my boy bits or grow new girl bits. I just really enjoy the feeling of transforming myself into a good looking woman whenever I get the opportunity - and time obviously. I’ve always loved and appreciated women and femininity and really respect the time, effort, and money that a woman puts into making herself look and feel good on a daily basis.

I’ve had partners over the years that have known about this and some that haven’t. Some accepted it and took part in the feminisation process helping and guiding me through various attempts at perfecting my look. Others weren’t so accepting, although they didn’t mind if I dressed by myself, rather than in front of them. They all knew that it was a big part of my life and one that had to be allowed to exist in its own particular way. I used to go for weeks or months without dressing, but every now and again I really have to scratch that itch.

As I said, I started on this road many years ago and it’s slowly gathered pace to where I am just now - I have a place to myself and the ability to dress whenever I want. I’ve a selection of clothes, shoes, make up and wigs that I’ve accumulated over the years and I’ve found this lockdown to be particularly helpful with the amount of time I can spend fully feminised. I don’t have to worry about unexpected visitors (yikes), nosey neighbours, and I can spend as much time as I want dressed exactly as I want. I also occasionaly meet others the same as myself and we spend time together dressed as females and to be perfectly honest with you I've enjoyed performing oral on them whilst dressed.

I know that this letter might - or might not - have come as a surprise to you, but as someone that I can happily call one of my dearest and closest friends I really want to get it off my chest and invite you to know about that very important and significant part of my life. Over the time we’ve spent together I feel that you accept different lifestyles and hope that you can now accept that the person standing before you is still the exact same person, but with an extra persona that has shared his life for many years. 

You must be thinking a thousand and one things at the moment, but if you want to ask me anything at all, then I’ll answer you as honestly and as openly as I can…. 

Your new friend 

Fiona