I have been dressing since was about 5. Yes 5.This is another story for another time. I has started a new job working as a sales executive for a company making ladies lingerie. Good job for a TV!!!!. The designer, Sue, caught my eye as her make up was immaculate and she dressed well for a designer. It transpired that she lived in the next village,well a Market Town which was a small detour from my house.There was an immediate chemistry between us although it took some time for me to realise it. We had to visit customers together and time in the car which led to me complementing her on her make up.Little did Sue know that I wished that I could apply it as well as she did.One thing led to another and we ended up in bed. I wanted to be fair to her so I gave her hints that I had a secret but she did not get them. In the end I gave her a massive clue while we were returning from a customer visit. She went ballistic. No surprise really. She would not speak to me for days.My worst fear was to be "out" as I had a career, wife child who I loved to bits and did not want them to be hurt in any way.The next few days were nerve wracking to say the least. Sue knew that my wife worked every Saturday so she called me and asked me to come over.When I arrived she was had had a "couple" of glass of wine and took me straight up to bed.She took the lead and had her way with me.This was not the reason for the invite.As we lay in bed Sue said she had thought a lot about me and what I was. She offered to help me with my make up and to become more feminine.Can you imagine how I felt!!!!.Sue had excepted me for who I was and as I found out later, had fallen for both of us. I went over some Saturday evenings when my wife was away.Sue told me to arrive dressed, without make up.I dressed in cream trousers, tan belt with matching shoes,an old fashioned blouse and wig.It was raining so I used an umbrella which was a relieve as this was to be my first venture outside the house dressed as Cara, the name Sue had given to me(it means Lady in Italian or so Sue told me). I arrived at her door, knocked and waited and waited. After what seemed a lifetime Sue opened the door." Sorry I was upstairs". Yes I am sure you were I thought. As a fella, I am an arrogant know it all or I used to be in my mid 30's.Being dressed change my personality to being I suppose the opposite.The first thing Sue said that I might a least have put some lipstick on. That set the tone. Sue was in control.She sat me down in a chair, look my wig and blouse off leaving me sat with only my fem trousers, bra and silicone breasts. The 2 hour long make up lesson began. Sue explained everything she was doing, chose the colours to best suit me.When she had finished the make up she brushed my wig out and spent a lot if time getting it to suit me. After nearly three hours, all i needed was a nice top. Sue disappeared up stairs and came back with a cream satin chemise sleeveless top. She very carefully slid it over my head so as not to catch my make up.Sue told me to go and look in the mirror. To say I was pleased would be an understatement!!!. What I saw was what I had always wanted to try to achieve my self.I never knew that I could look so feminine.Sue was a talented designer and a superb make up artist. I later discovered that she had studied make up during her days at college. Sue never had a hair out of place and I never saw her with out make up. Our relationship continued for about a year when we had girly lunch's, further sessions in make up dressing correctly and deportment.We did still sleep together and on one occasion, I had taped my penis out of the way. This was something I often did and had perfected it so that I could still go the the loo all be it sitting down.Sue and I had gone upstairs to her lovely feminine room which I loved to be in. She had undressed completely but asked me to keep my all my underwear on.This was the first of many sessions we had like this in bed. I was always in my underwear and Sue more often thsn not. Sue was not one for kissing at the beginning of our love making as she was fastidious about her make up. This particular time was the first time that I had been taped up.when Sue slid her lovely hands into my panties, she hesitated for a second but then started to stroke me as she would do to herself.We we both very turned on and I know Sue was wanting me inside her. I told her I needed the loo. I got up. collected my hand bag and went to do what I had to do. When I came back Sue was masturbating with her eyes closed. I slid back under the covers and gently got on top of her.She opened and raised her legs and went down to mt groin. This is when she got the surprise. I had a nice large strap on.Sue was annoyed and said I was turning her into a lesbian.Her annoyance lasted for a few seconds ans she then guided my new penis into her very wet love tube.I cannot remember how long or how may positions we tried.All I know is that I was able to to keep Sue in a virtually continuous climax. We did have a few more lovely sessions together and quite often we did not feel the need for full on sex. I remember once being in her lounge ans she had gone upstairs. I quickly took my outer cloths off and then lay in front of her fire. She came down stairs and when she came into the room I was on my side on propped up with my arm and striking a sexy pose. Sue told me to stop. I asked why and she said it was turning her on.The rest you can imagine. Sadly the job did not work out for me but we still managed to see each other for about a year. It was not so intense but we both enjoyed each others company and the occasional time in bed. It all came to an ens when the company had to close and Sue moved to the London area and went back to designing wedding dresses. We lost touch and It is now about 16 or so years since I have seen or spoken to her.Sue was my mentor and one of the most genuine and sincere people I have ever known. The next part of my exploits is to come al of which are true.