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First Time Crossdressing

"Where it all started"

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I have been meaning to write this for a while but never got round to it This is my first crossdressing experience and I promise it is totally true. Back in 1988 when I was just a young lad of 18, my college had a rag week and a fancy-dress day. My best friend, Anna, had an idea for me. She had, the year before, left school (a catholic girl’s school) and still having her uniform, suggested that I wear it. Being a rash teenager, I jumped at the chance. So, the morning in question I went to her house and she shaved my legs, did my makeup, and dressed me in school skirt, blouse, blazer and stockings (I am sure they were not part of the uniform!) The morning was, as you can imagine, filled with the usual banter and skirt lifting and I loved the attention. At lunchtime we always went to the bar on the college campus which it shared with the local sports centre. It was during lunch that I realised an unforeseen problem. The only toilets were in the changing rooms. Oh well. Quick swig of Dutch courage and away I went. When I walked in there were a few guys getting changed and the naked ones quickly grabbed their towels until they realised that I was not a girl. Certainly got a few comments but they were all good natured. Now I was starting to get brave!! After College I worked at a restaurant out of town (Happy Eater if you remember those from the 80’s) This involved changing from my outfit, which I was starting to love too much, into drabs. Walking through town, getting on a bus and travelling 4 miles to work and then change into uniform. I decided to skip the drabs bit and go dressed. Most people just turned their heads, some commented but all good natured. A couple of days later I unfortunately had to give Anna her uniform back and It was some years before I went out dressed again. It was an amazing feeling, not to mention being turned on all day, and partly why I love being out as Sophie now. Hope that this has inspired some of you to be yourself and be proud of it. People really do not judge as much as you may think!
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Written by Sophie_Jane

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