Fantasy #21: Sissy Discovery

Figuring yourself out was going to be tough. You were quickly realizing that after you’d turned 18. You thought you’d figured out what you were but the thoughts you once considered deeply embarrassing were beginning to feel too good to ignore. Despite being fully comfortable as a boy, you now dreamed of dressing as a girl, of servicing a man as a woman.

At one point in time, you were a master at distancing these thoughts from your mind, of shutting out the silly notion that you could be someone’s girl. All you had to was breathe deeply and count to ten and the thoughts would go away… until you got drunk and found yourself looking up sissy porn, imagining yourself as the heroine getting plowed by her daddy.

You discounted those ideas as a side-effect of alcohol but soon you would find yourself daydreaming of lace panties and stockings as you rode in public transport. You counted yourself lucky on those occasions since you could hide your throbbing erection behind your backpack but still, you knew you were going to have to do something drastic to get ahead of these fantasies and soon.

You browsed sissy content more readily now, albeit still in the shadows. You started with porn boards and ended up in chat rooms. You’d even begun your local classifieds, reading every post there, hoping you might find someone there to show you the way. All you found there were flakes and pretenders, disappointment after disappointment. You realized that you were all you had to rely on to keep sane, that you would have to train yourself or chance losing what grip you still had.

You purchased yourself an Amazon gift card and made a throw-away account named “SissyJazzy”. You purchased your very first lingerie set and a beginner-sized dildo, being very careful that you would be around to receive the delivery. When the deliveryman rang at your family home, you raced to the door and signed for it without incident. He had no idea what he’d delivered to you and you were somehow disappointed, as though you had both missed out on some kind of perverted fun.

You were now home alone with your version of Pandora’s box; a receptacle containing the world you had denied yourself, the world that embarrassed you deeply yet excited you and consumed your deepest thoughts. You were on the doorstep of that world now, all you had to do was open the box, yet you hesitated. Was this something that you really wanted? Was this who you were? You put the box under your bed and ran out of your room, abandoning the box for now.

You sat down to play a videogame but couldn’t get past the start screen, so consumed was your mind with the contents of the box. You ran awkwardly back to the room not five minutes later and shut your door. The box and the treasures that lay within was all that was on your mind. To deny yourself any further would’ve been impossible. You cut the tape and reverently laid its unwrapped contents on your bed.

It was a simple black lace bra and panty set, stay-up stockings, and a dildo the size of an average cock, barely bigger than your own. You stripped down quickly and dressed up slowly, enjoying the feel of the lace and nylon on your smooth skin, barely able to keep your hands from your bouncing cock. You grabbed the dildo and squeezed it while touching yourself with your other hand, pretending the dildo belonged to a man. Before you knew what you were doing, you lost yourself upon the dildo, sucking it sweetly and tenderly. You somehow managed to avoid soiling your lingerie and shot out on your wooden floor before collapsing on your bed. You enjoyed every pulse of your orgasm and the subsequent after-shocks quivered through your body. You’d just experienced the best orgasm of your life and knew you would be hooked.

This was you, whether you liked it or not.

A month went by and you had become thoroughly acquainted with the ins and outs of your dildo. You’d learned that any lubrication, even spit, was better than none. You’d discovered that place deep within you that could make you come even harder, that you enjoyed ignoring your erect self to increase the pleasure you could receive. You now wore panties whenever you could under your clothes and had ordered a few more pairs in the hopes of having a set for every day of the week. You’d continued your consumption of sissy hypnosis videos and had now decided on the purchase of a chastity set.

You went to a sex shop, your sexiest black thong on beneath your tight jeans. It was the middle of the day and three creepy older men were shuffling around. You were scared and nervous but gathered yourself enough to head to the back of the store. You soon found the chastity section and had to bend down to make your selection. One of the old men must have followed you there because you soon found a man pressing against you with something hard. You became paralyzed as your head swam with a multitude of feelings: fear, repulsion, violation… yet it was also strangely pleasurable to be so strongly desired, to feel the object of that desire pressed upon you. You felt an exhilaration unlike any other as he made his proposition to you: fuck then and there and you’d walk out of the store with anything you liked.

Normally such a scandalous offer would have seen you run away but you didn’t hesitate as you felt him through his pants and rubbed yourself on him. You would no longer be fleeing opportunity as you had done before. No, you were now resolute upon seizing any and every chance you could. And seize it you did.

You sucked him for a minute before he turned you around, pulled your thong to the side and took you. He was your first and even with your training, he hurt you before the pain melted into the pleasure of being taken. He didn’t last long but that didn’t matter much: you came as you felt his cum drip down your backside. He ordered you to make your selection and he bought everything you selected. He then walked out of the store and you never saw him again.

As you walked home with your new bag of goodies, you realized you’d whored yourself out. That you had loved whoring yourself out. That you would do it again and enjoy every last second of it. That a whore was what you were.

You locked yourself in chastity that night and dreamed of all that was to come in your new life as a sissy whore. You dreamed of silk dresses and hard cock, of lacy things being ripped off of you by crazed men, of being overwhelmed by a party as they worshipped you with their lust. You dreamed of hotel rooms and back-alleys, of hiking paths and truckbeds. You dreamed of spacious rooms where you were the center of attention for bachelor parties, of the bashful attention of a first-timer, of the no-time wasted approach of an experienced john. You dreamed of being a whore.

You had found yourself, your crossdressing-whore-of a-self and nothing was going to stop you from being you.

Not anymore.

I make no promises but I would like to return to a regular posting schedule and have something new every week for you beautiful perverted people.

See you next week,

Photo by luizclas from Pexels

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