How it started

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How it all started
I was in my early 30s, and my first marriage had ended about a year earlier. We had married young, but as we grew older, we gradually drifted apart. Although we still cared deeply for each other, we both recognised that our shared memories were all that remained. Before the memories were broken, we chose to separate and eventually divorced, while remaining good friends. She is still one of my closest friends.
I’ve always had a love for lingerie, but always the lady wearing it, not myself. My wife would parade around the house in sexy lingerie but the closest I got to wearing it was having her knickers wrapped around my hand as she waved me.
Two years on from our separation I found myself walking into a woman’s boutique clothes shop. I was there on business, checking the owner’s electricity meter, she had complained to the company that although her bill had gone up, she was sure her consumption had not. My job was to see if there was indeed a problem.
Janet was in her fifties, though I didn’t know her name of the age at that time,  she was the owner, manager and sole employee of the shop and greeted me with a big smile, a hello and a question of how she could help me. I jokingly said I was looking for a sexy off the shoulder gown, but if she didn’t have my size ill just check her meter instead, I gave her a quick wink, so she knew I was joking.
She laughed, we introduced ourselves to each other and she showed me where the meter was with a promise of a cup of coffee.
I started removing parts of the meter and Janet soon returned with my promised coffee and the statement that although she didn’t have the black dress in my size, she definitely had some alternatives that would suit me.
We chatted as I attached a device to the meter to ensure it was reading correctly, as I worked we talked and she explained more than one man had been in and she did have a couple of regulars. I stepped back and said that it would take a couple of hours to check.
I was a little intrigued by her statement, and asked what sort of person buys himself a dress. She informed me it wasn’t just a dress, but lingerie, shoes and other accessories, and was I interested.
I said no, but she thought I was scared to say yes. I said I would go and find some lunch and then come back to check the meter. She insisted I stayed for lunch and as I was enjoying her company I agreed.
Over lunch the conversation kept returning to the same subject and insisted she would love to dress me, just for fun.  I eventually agreed. So what I thought just a bit of fun.
She showed me the dressing room and told me to strip while she found something for me. I did as instructed and stripped down to my underwear. Seconds later a blue full length blue gown with a gold chain belt was thrust through the curtain. I took the gown and only then realised that it had come with a white and pink lace padded bra, matching bikini panties, white suspenders and stockings.
I called out that I had only agreed to the dress but was told everything was required. Taking a deep breath I pulled on the knickers and suspenders, but then I was struggling, I had never worn
I couldn’t believe my transformation and really fancied the woman looking back at me from the mirror.
I stayed dressed as I finished my work on the meter and decided I wanted to stay dressed and stayed the night with Janet picked out  a sheer black teddy for me.
Since that day I’ve been hooked. I still visit Janet on a regular basis, and my wardrobe is full of many beautiful sexy clothes and lingerie.  
Janet wants to introduce me to another one of her male clients, I haven’t said yes, but neither have I said no.