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Early days

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By (user no longer on site) OP   
over a year ago

How I first got started

When I was around 13 or 14 I used o go into the woods near me with a friend. We were both raging hormonal boys so you can imagine our obsession.

We would find porn mags and read them together and then play ‘truth or dare’. I always chose the dares as my friend liked me to hold his cock or put it in my mouth which I was only too pleased to do. He wasn’t as into it as me though so after a while it stopped.

I used to deliver the papers and on Sunday’s I used to accidentally keep a copy of one of the colour supplements and go into the woods and wank off to the sexy women in them. Really though I was turned on by the clothes and shoes and dreaming of being dressed like that.

One day as I cleaned up and left I realised a man had been watching me. When I looked at him he turned away and walked off.

Back in those days I traveled a lot by train and station toilets were a favourite of mine. I’d spend ages in the cubicles reading all the sexy graffiti stories and playing with myself. I was still very naive though and didn’t really pay much attention to the holes in the cubicle walls and the missing door locks. One day I was reading a hot story about anal sex and was very turned on when an older guy pushed into my cubicle. He was very flushed and had obviously been spying on me. He grabbed my cock and began to slowly wank me. I was terrified but also so turned on. I didn’t last long and came all over his hand and he licked it clean.

Sorry to say I lost my nerve and left but I really wish I’d stayed and returned the favour.

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By (user no longer on site)
over a year ago

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By *titch69Man
over a year ago

Westcliff

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By (user no longer on site)
over a year ago

More please x

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By *rouble 50Man
over a year ago

turriff

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By *nly1meMan
over a year ago

here there n everywhere

Sounds hot please continue x

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By (user no longer on site) OP   
over a year ago

My next step was my first time cross dressing. Obviously the catalogue lingerie pages were well thumbed and I was fascinated by wearing some of the clothes. Even back then stockings and suspenders triggered something in me.

One day I was home alone - parents at work and no college. I went into my mum’s drawers and my heart was hammering so fast when I found a suspender belt and some stockings. I decided to try to get into a pair of her heels too - she’s a six and I’m an eight.

I went into my room and stripped off already as hard as I’d ever been. Slowly I savoured fastening the belt and rolling the stockings on and clipping them to the suspenders. Then I squeezed into the heels and was feeling so turned on. I began to mimic the poses from porn mags in front of a mirror and realised my first fees kept brushing my tight hole and it was the most amazing tingle as I did.

Next thing I was frantically fingering myself and then sliding a hair brush handle in and out. I was so hard and not surprisingly I had the most intense orgasm with more cum then I’d ever had before.

Fortunately none on the lingerie or shoes though

I was hooked now and regularly slipped into mum’s stuff and wanked.

A sissy girl was awakening

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By (user no longer on site)
over a year ago

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