It had been a while...

The first time I dabbled with cross-dressing was as a horny teenager. I discovered my grandmother’s vintage collection of lingerie, and I had to know how it felt to be encased in girdles, basques and corsets, to feel the taboo delight of having my legs encased in sensuous nylon, to figure out how to attach stocking tops to the metal clips of suspender belts and to experiment with her array of lipstick colours. Many a glorious, guilty teen orgasm was had whilst dressed as a tart, spilling huge loads as I admired my transformed look in the full length mirror.

I then rediscovered my fetish a couple of years after starting work, my compulsion to buy my very first outfit becoming a small adventure in itself. I’m sure that the assistants at the checkout didn’t give two fucks whether I was buying the outfits for myself or for a partner, but each purchase was an exhilarating and terrifying ordeal, with the reward of a lingerie clad wank afterwards being the sweetest of treats. I would try out different colours and figure out what women’s sizes actually meant when trying to fit the frame of a 215 lb man! I would buy a cheap make-up kit and amateurishly experiment with mascara and eyeshadows, painting my lips in different colours of lipstick to compliment my choice of underwear. And then after a few months, I grew bored and moved onto something else. I discarded my spunk stained and stretched collection and never thought about it again for maybe fifteen years or more.

I had discovered the delights of shemale porn for the very first time, and there was to be no going back to ordinary pornography after setting eyes on that! Up to that point, I would have considered myself bisexual. I would occasionally get lucky on a weekend, and end up going back to a girl’s house for a weekend shag. I more often than not, could be found inside a cubicle at my local public toilets with a pensioner’s elderly cock in my mouth on a Sunday afternoon, as well! I enjoyed both scenarios, but the naughty toilet sex with dirty old men was definitely more thrilling. But after setting eyes on the glamorous adult stars of the transsexual movies, my interest in pussy fell by the wayside. These ‘gurls’ looked gorgeous, and had a meaty surprise inside their panties…