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Chapter 50
by
JerkGently
Chapter 50
Chapter 50
Half an hour later, the pair of you were hidden in the shadows along the side of just another suburban townhouse. Just about free of the cheek-reddening exaltations that had splattered across the wall of that lonely photo-booth and given Terry yet another slimy skip to his step.
The boy was tugging the high heels from his delicate feet, half-in and half-out of his slutty attire already. A precautionary action you had helped him with many times before, just against the risk that someone heard him climbing in the window so late at night and the fact that he was dressed like a tarted-up little whorelette added even more complications to that scenario. As far as you knew… none of Terry’s family had any idea what had been happening to their son over the past month or so. You had been introduced, briefly, as a ‘female friend’... but had been too embarrassed by the whole situation to really engage with them at all. As far as they knew, their politely shy offspring had simply met a nice girl at school and now spent an awful lot of time with her 'family'. You weren’t even sure if he was facing any repercussions or consternation over those habits. It was so far from the stifling household you had grown up in, or the new one that had adopted you.
Still, you could never complain at another brief opportunity to see Terry’s naked form in the moonlight. Goosebumps growing on his skin as he tried to dig through a bag for the more masculine uniform he had been wearing earlier. It seemed strange, watching him try to drag on the false-flag trappings of a ‘real boy’, even with a generous amount of makeup still all over his face. It seemed so backwards, somehow… so far from who you now knew him to be. Personally, you couldn’t remember the last time you wore trousers… or anything that hid your pierced belly-button. The surgery had already been booked to add more than a little weight to your chest… in all honesty, you could hardly wait.
“Come up with me… for just a bit?” The hope was clear and watery in Terry’s eyes. He couldn’t bear for you to go just yet. You sighed heavily… knowing it would be an early morning’s fucking that woke you up, however late you got back to the flat. But still… You couldn’t break the boy's heart here, and there tended to be ample opportunities to catch a nap, during your average working day.
The pair of you clambered up the well-known tree that led to his bedroom window. You feeling the wind whistling up under your skirt as you left the ground an awfully good view, should anyone have been around to claim it. Your companion slid the frame open and clambered in… waiting a moment or two for any sounds of sudden interest from the otherwise silent house. Then beckoned you on inside, to land upon his soft bed.
The room seemed like any general teenager's, with perhaps just a few subtle hints of something more. Hanging proudly on the back of his door was a schoolgirl outfit Skeg had bought him, most certainly not up to standards for his own institution. Somehow his parents had clearly never noticed it, hidden in plain sight. Much like the secret collection of thongs and lacy underwear stuffed to the back of his drawers, some of which had once belonged to you… and perhaps never been washed since. Or the high-heels secreted to the back of his wardrobe and glittering miniskirts and bikinis hidden inside rarely-worn suits. The only real sign of the boy’s submissive new reality were the posters on his wall… which had all slowly become androgynous characters upon their knees. Tongues out and eyelashes fluttering. Unregistered role models for any sissy femboy looking to earn himself a place below the table.
You listened to him tiptoe off to wash his face, and relieve a bladder that you yourself had been pushing against, not so long ago. It was so strange to be staring up at someone else’s ceiling, like the snuck-in girlfriend of so many mainstream sitcoms. It was almost soothing, to hear your heart beating in your ears for what was really a more normal state of trepidation than you were used to. If his parents really did wake up now it would be… awkward… but not world ending by any measure. They would just see their son as having snuck in his slightly under-dressed friend late at night. The kind of teenage hijinks which were actually swiftly forgiven. With no knowledge that you were both, in fact, still filled with the semen of several different strangers and had just screwed each other senseless in full public view. It really was a veneer of normality that you so rarely got to breach the surface of these days… A reminder that outside the shop and flat, another world still kept turning over, the same as it ever had.
Terry finished in the bathroom and returned to snuggle down next to you. Before long you were both just naked again. Softened penises touching beneath the covers and breath stirring against each other’s cheeks. Cuddling up in the womb of the night, a place of limbo that belonged to neither side of your existence.
Chapter 51
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Submitting with Step-sister
Feminised by your favourite family member
Jo and Jenny are two 18 year old step-siblings on the cusp of adulthood, raised in an uncaring household of luxury and expectation. Determined to flee this gilded prison, they formulate a plan to escape, aided by an unsavoury ‘acquaintance’ of Jenny, known only as Skeg. Seen through the eyes of Jo, a shy, polite young man with a possibly unhealthy devotion to his step-sister, you will be swept along as he is to play the part of her ‘twin’. Learning to dress, live and satisfy all manner of wanton lusts as a member of the opposite gender. For the boundaries of Jenny’s ‘deal’ with Skeg seem ever changing, and her own eagerness to explore this grimy new world of slums, sex and submission; unquenchable. Will poor Jo be able to keep up with her insatiable vision for their new life? Will he be able to retain some sense of self and innocence amongst all this debauchery? Read on for a tale of taboo lusts, bisexual prostitution and finding one’s true place in the world.
Updated on Apr 28, 2024
by JerkGently
Created on Jul 28, 2023
by JerkGently
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