When I left home and moved into my own place in my early 20’s I started to gather a few clothes of my own to satisfy my growing desire to cross dress, some lingerie sets, satin chemises, shoes, skirts, dresses. My favourite outfits always included high heels, stockings and a satin chemise under a short dress.

Up until my late 20s I only played dress up occasionally, always at home when I was alone and when I was sure I wouldn’t be found out. I kept all my clothes hidden in a trunk, tucked away in the garage where I was sure it would not be discovered when I have friends round.

While these occasional dress ups this satisfied my sexual urges and always gave me incredible orgasms, shooting streams of cum onto my satin chemise and stockings, I now wanted to experience more of what it would feel like to be a girl. I bought some make up, a cheap wig and some junk jewellery and after some practice found that I could make myself look reasonably passable, as long as I shaved my legs and dressed a little more modestly than I had been. I also purchased a dildo and used this to pretend I was being used my a man both anally and orally. My orgasms became stronger when I was pretending to be a real girl submitting to a dominant male, on my knees with the dildo pushed deep into my throat or bottom.

For my first time out in public dressed as as girl, I bought an above the knee black dress with red poppy floral details. The dress was a made of a sheer material layered over a solid nylon liner. It had a fitted bodice, slightly flared skirt and long semi sheer sleeves, a very secretarial look at the time. I planned to venture out after dark to a nearby town that I rarely visited and where none of my friends lived.

It would be dark around 7pm so come late afternoon I started to get ready. I took my time, enjoying a nice scented bath followed by a close shave of my face, legs and armpits. My bottom had always been girly smooth and I kept my intimate area closely trimmed. On getting out of the bath I was already excited, my heart rate had increased and my girly cock had started to enlarge at the thought of getting dressed.

I put on a black lace stocking belt and carefully rolled on a pair of 10 denier nearly black stockings, arranging the rear straps perfectly so they clipped well behind me and followed the curvature of my bottom cheeks. I then arranged to the front straps to be nice and straight. I can’t stand badly worn stockings. I then put on a pair of tight black lacy panties that now barely contained my excitement and when pulled up exposed a large area of my bottom cheeks. I then put on a matching bra and inserted my c cup breast forms, not too small and not too big to stand out. To finish my lingerie look I pulled on a simple black satin chemise that finished just below my bottom cheeks with a deep lace trim that aligned perfectly with the top of my stockings. I then put on my black patent 7cm heels and carefully fastened the ankle straps.

Standing back and admiring my work in the full length mirror I was fully aroused by my appearance and struggled to restrain myself from touching the, now rather too large, bulge in my panties. I quickly applied a little perfume to each side of my neck, a subtle feminine scent, not too strong.

Next was my make up and hair. Not too much makeup, a little eyeliner, mascara, foundation, powder and a little blusher. Some deep red lipstick and matching nail varnish. I selected a shoulder length brown wig with highlights, then carefully brushed and clipped this neatly into place with a thin black hair band.

Finally I stepped into the dress I’d bought for the occasion and carefully pulled it up, struggling a little to fasten the zip at the back. I smoothed down my dress and stepped back in front of the full length mirror. I was astonished with my appearance, a smart but sexy office girl look not too stand out but enough to be attractive and very passable for anything other than close inspection. To finish off the look I selected a simple sliver pendant necklace, a sliver bangle and a selection of silver rings.

So the time had come, I was shaking with excitement and equal amounts of fear and trepidation and now not sure if I was brave enough for my first trip out. I needed to get into a persona, I needed a name. Rebecca came immediately to mind, I’d always loved the name and somehow I really felt like a Rebecca. Standing in front of the mirror for a final time I took some pictures of Rebecca before her first trip out, a few coy poses and some showing a little stocking top. I’ve always been a flirt and was now fantasising about flashing my stocking tops. I grabbed a little, jacket style, short black coat with a belt, that still showed off my above knee dress, a black handbag with my essential makeup repair kit, my mobile phone and some cash. I also took a small paperback book of erotic literature I’d picked up a few years ago when working away from home.

It was dark outside, a clear spring evening with a little crispness in the air that I immediately felt on my stockinged legs and up under my dress. I loved that feeling, something that you just don’t get dressed as a boy. I lived in a very rural area that was not overlooked by neighbours so I could safely walk to my car without being seen. This was it, I was physically trembling as I started the engine.

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