Disclaimer - this is a complete work of fantasy fiction, none of the characters are based on any real persons, living or dead.
You don't know how it started, do you?
You only have vague recollections of trying on your sister's clothes at a very young age and being scolded for it. Such was the way of the world back then. Over the years you developed more of a taste for women's clothes, starting with panties. If your girlfiend happened to leave a pair lying around, you'd be sniffing them to inhale her womanly scent when she wasn't looking. Hell, you'd even try them on if she forgot to take them home. The feeling of sliding silk panties up your legs and over your ass was amazing. The way they cupped your balls tightly after you tucked in your manhood gave you an erection as hard as steel.
"This is better than viagra!" you thought.
You couldn't get enough of it.
You had one girlfriend in particular who seemed to sense you liked her panties as much as her pussy. She 'accidentally' left her used panties in your flat every weekend. Seeing that you seemed happier in general, she started leaving other things of hers too. Stockings, underskirts, bras, make-up.
One time she left a mini-skirt.
That was it, you were done.
One try of wearing that and your days as a real man were numbered. And you knew it. You remember acquiring a pair of high heels from a charity store. They complimented the skirt perfectly, along with the stockings, panties and bra that she'd left at yours. The high heels pushed your ass higher and outwards, just like a real girl's. You put on lipstick, eye shadow and mascara to round off the look, before checking yourself in the mirror. You gasped at how pretty you were. You almost cried tears of joy as in that moment, as you saw your true self emerge, like a butterfly from a coccoon. Emotionally overwhelmed, you collapsed onto the settee and cried like a girl. When you'd calmed down, you realized how amazing the clothes all felt and how stiff your boner was. All you had to do was rub yourself through those sheer panties and you automatically squirted 9 wads of sissy juice high in the air! Your balls kept pumping the cream relentlessly, in a hands free orgasm from heaven. It was a mind blowing, cumming so deeply like you'd never felt before. It seemed the more girl clothes you wore at the same time, the harder and harder you came.
You needed more of it.
That's when you decided to shop for your own stuff and you soon had a full girl's wardrobe, just as big as your guy wardrobe. Your girlfiend discovered the whole collection one night and dumped you, but you didn't care. Soon the balanced tipped and you had mainly girl's gear, a lot of unisex gear and only some guy gear left.
But, it still wasn't enough.
You found an online chemist who didn't ask too many questions and soon you were having estrogen delivered to your door. Female hormones sent you crazy with feminine feelings and you loved it. You were never happier. You started watching sissy hypno vids and things started to really change. The sound files were even better, as you had to use your imagination. They took you deeper into girl world than you'd ever been. In no time at all, you were craving cock.
You were shocked at yourself at first and even considered purging.
"This has went too far!" you told yourself.
Then quickly added - "Too far to stop!"
You seen enough online meme captions that told you it wasn't gay to blow another guy, if you were dressed like a girl. You'd also invested too much in your wardrobe, time and emotions to quit. Something told you to keep going, no matter what. That something was your 'inner girl.' Soon you were daring to go outside while dressed.
Mainly after dark, when no-one was around. You walked the empty streets of smallsville, time after time. In a long skirt to begin with, but the more you got used to it, the braver you became. Midi skirts and then mini-skirts adorned your sissy ass, which you swayed from side-to-side, as your high heels clicked on the pavement.
You never felt more free.
You loved windy nights the best. The feel of the breeze caressing your thighs and even flapping your skirt against your g-string adorned ass was heavenly. The stretch of your nylon stockings pulling on your garter belt, the feel of the breeze finding its way inside your bra, the wind blowing your hair around along with your hoop earrings.
You loved it all.
You had done enough research to know that trangender women were supposed to blend in with what the local woman wore, but that was too boring. You lived in a small town and who wanted to wear dull grey trackie bottoms, shapeless hoodie tops or frumpy cardigans? The M&S look was not what you were after, it was not exciting in any way. You wanted to look like a slut.
And you totally did.
Moreover, you actually looked like a hooker! The leopard print imitation fur jacket you bought left no doubt about it. Added with the split pencil skirt, fishnet stockings, sheer silk blouse, visible bra with hidden breast forms beneath, stilletto heels and ultra femme shoulder bag - you looked like a street whore, from head to toe. You looked in the mirror, pleased with yourself as you dabbed on some 'Ghost' perfume to complete the transformation. You nervously opened your door and checked no-one was around. The coast was clear.
It was time for another walk on the wild side, though you had a feeling that this one would be like no other...
[tbc]
(c) Joni Van Esdaile