Chapter 30
by
JerkGently
Sharpened inexperience
The pains of teaching
The indefatigable redhead gasped as she pulled down your latticed panties, revealing in full what had been barely hidden within. Much like with Sara, you suspected she had been expecting a lot less of you down there than there was… or perhaps she had never even seen one up close before?
“Do you not have a boyfriend, Shelly?” You ventured, wondering why exactly this quite attractive and clearly confident young woman might need to be making deals with the likes of you and Tomi.
“I do… But he wants to ‘save himself for marriage’. He’s really sweet, but his family are kinda weirdly religious and stuff.”
Ah, that explained it, you realised. The girl wanted it both ways: to have her squeaky clean Disney relationship… and also play around the edges a little. You understood. Without pretending to have a say in the morals of it. You understood.
She was bouncing the still-flaccid length of you from hand to hand. Soft fingers juggling your flesh in the sunshine.
“Shouldn’t it be getting hard?” She questioned, glancing up at you with possibly accusatory eyes.
And, as if by magic, you felt your flesh indeed begin to rise. Though whether in reaction to the work of her fingers, a general fear of disappointing or a deeper lust for stern glares; you simply couldn’t tell. A sissy simply stood to attention when it was asked of him, you supposed.
Shelly was already infatuated with her control over the thing, leaning in closer to give it her full attention. You could only glance nervously around at the windows overlooking your garden, wondering what anyone would think should they look out and see this unfolding situation: A teen in school uniform lifting up the skirt of their newest stay-at-home neighbour, fondling the meaty pillar she’d found within.
Without warning, you felt Shelly’s lips close in around the tip of you. Wasting no time in trying to emulate what she’d clearly seen done in one pornographic video or another. You supposed a girl growing increasingly frustrated at her highschool crush’s chastity might have been ‘researching’ this moment for a while. Salivating over the idea of finally getting her hands on just any phallus she could. There was certainly an abundance of enthusiasm in the way she suckled you into each cheek, perhaps only just realising the stretch of certain muscles such feats required.
You bounced between teeth a little, feeling the pinch of her inexperience. She tried to take you too deep, too quickly and ended up gagging and spluttering. Before long there were small trails of cheap mascara running down from the corners of her eyes. Yet still she pushed on, determined to make the most of this opportunity. With a sigh, you realised you were going to have to step in… if only to save your poor, tender penis from being peeled away by the persistence of this amateur young sword-swallower.
“Slow down…” You instructed, gently. “Let your lips fold over your teeth a little and relax.”
Those fierce eyes flickered again, searching for any sign you were mocking or criticising her. When she found none, she began doing as instructed though… bowing to your years of experience in such matters.
“That’s it… now use your tongue a little and look up at me. Watch my eyes to see what works and what doesn’t…”
It felt quite strange, to be offering instruction in technique to the one who was currently sucking your cock on a weekday afternoon. But somehow it also helped soothe your little, submissive sense that this was all the wrong way round. She wanted to learn how to do this thing properly, so really you were just being a teaching aid instead of a toy today. Once you’d got that little bit of math out the way, you found yourself much more able to enjoy the experience as well.
By the end, you were quite proud of how far she’d come in so short a time. Sliding her head forward and back rhythmically as she applied a tight ring of suction. Using her hands to provide a stroking counterpoint to each slurping movement and her tongue to add some changing texture to the entire experience. She even managed to take the head of you into her throat a little, though she struggled to fight her gag reflex each and every time. It felt guiltily good, to be the first step on what you were already sure was going to be a long career in cockgobbling for this particular young creature. She had a sordid streak of awkward eagerness behind her more performative, bratty personality that you were sure would be driving men wild in more than one way for years to come. There was a slut in there, waiting to blossom: ‘it takes one to know one’ and ‘game recognise game’, etc. etc.
Your own climax crept up on you… and certainly surprised Shelly. The coalescing sensations from what had started out as a pretty un-erotic experience, but slowly became a very pleasurable one, bursting forth without much warning. The redhead gave a startled gurgle, as her mouth suddenly filled with warm, salty goo. She immediately tried to extract herself and spit the offending substance to the floor… only to receive two more spurting ejections straight in her face. The result was a positively furious-looking teenager with one eye sealed shut and trails of cum both laced into her ginger curls and dribbling down her chin.
With a stern look, she used your own skirt to clean herself off a little; though not enough to remove every drop of creamy gunk clinging to her hair. She didn’t give you time to let her know of the evidence still remaining, however.
“Okay.” Was all she offered, as if some grand determination had been made. Then turned and flounced her way back through the gate, without another word of goodbye.
A growing community
A Sissy Saves the Neighbourhood
Wholesome tales of your friendly local femboy
You, (Sam), are a 24 year old femboy who has just moved into a new home in quiet suburbia. After a difficult upbringing and many trials in finding yourself... you have finally found the life of your dreams. Ben, your forever-partner, has found a new career with a successful company and asked you to be his submissive, sissy househusband. It is a prospect that both excites you and terrifies you in equal measure. You know very little about cooking, cleaning or running a home. You have left all your inner-city friends and expectations behind. You have no idea how the local people might react to the two of you and your unusual relationship. There is no going back now though... You have thrown out all your old clothes. All traces of the shy, outwardly masculine life you had before. From now on you are nothing but your master/lover's pretty, little plaything. Skipping to the shops in flowing summer dresses and kneeling at the door to await his return home from work. This is all you've ever wanted... So you will definitely make it work!
Updated on May 17, 2026
by JerkGently
Created on May 24, 2021
by JerkGently
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