Once a Slut Always a Slut

My dressing sessions were not particularly successful since I had no sisters; so the few clothes that I wore were mainly from my mother’s old clothes box. Masturbation would follow and once relieved I would hide my ‘treasures’ back in a secret place in a shed I used as my ‘den’.

I had also experimented with anal penetration using a large candle. At first I found that it hurt and I could not understand why anyone would do such a thing but after a couple of attempts I found that it needed to be well lubricated and that I needed to relax. Soon I was on to other objects which were much larger but provided I followed the lubricate/relax/lubricate try again process I could take some quite large things in. I was now hugely turned on by the whole anal thing and in my fantasises in bed at night I would imagine being penetrated by a guy whilst having my legs wrapped around his waist. So I assumed I way gay – although I could never imagine being with a man unless I was in full girl mode. I still fancied girls though and this confused me yet further – although I suspected I was intrigued by how girls’ minds worked rather than any thing else.

Occasionally, my older brother’s girlfriends would stay the night and might throw away tights or, in one case, stockings and I had managed to appropriate them before they got put into the dustbin. I had also slipped into their bedroom at any opportunity and tried some shoes on. Sadly, this was always very brief episode and only left me wanting more. I longed to wear girls’ clothes of my own age and style but I could not go and buy any since I had no money and I would have been embarrassed to death to go into a ladies shop and purchase anything even if I did have some.

I would watch fascinated when Sarah (one of the more longer term girlfriends) would sit and do her make-up in the kitchen. On one occasion she caught me watching and said, “You seem awfully interested, Charlie, in what I am doing – shall I show you what to do?” then laughed.