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Chapter 26
by
Trom1806
So, you decide that you should...
You shouldn't take any rash actions. The best option is to simply wait until the week is up...
Conflicting thoughts rage in your mind...
However, fears of the situation worsening and the dread of potential risks compel you to refrain from taking decisive action.
You think in dismay: "Perhaps I should just endure these days... Of course, the metal of this flat chastity cage is squeezing my penis and making me feel the humiliation of my situation every second... However, that rich viewer-donator promised to return the keys to this fucking metal device after a week... Perhaps I should just wait..."
Having made your decision, you carefully delete your browser history. You're ashamed to even imagine your roommate Peter finding out about your recent actions...
But it seems that to keep the secret, you'll have to not only keep silent about what happened, but also lie...
Peter soon returns to your dorm room.
He's carrying a large stack of books - clearly, your assumption about his visit to the library was correct...
However, before diving into his usual nerdy student activities, Peter reminds you of the additional conditions of that large donation.
It's not just wearing a flat chastity cage for a week straight...
Also: wearing women's underwear and practicing feminine makeup...
So, for about an hour, you and your roommate are **** to engage in activities that some might certainly consider shameful. You were both had to undress (leaving only women's underwear on), find online makeup tutorials for dummies...
And then (under Peter's guidance) you were **** to learn how to apply light pink women's lipstick.
And not only that...
Your roommate bought a whole set of women's cosmetics to fulfill the conditions of that generous donation.
Moisturizing face cream...
Lipstick...
Mascara...
Eye shadows...
You are **** to apply all of this to your face yourself, as if you were a girl, not a guy...
Your cheeks flush with shame, but you are **** to continue...
However, despite these distracting details, Peter also noticed that you were wearing a black women's thong, not lacy light pink women's panties.
Averting your gaze, you lied that you had decided to buy an additional set of women's underwear for the sake of the success of your future streaming broadcasts. Peter seemed to believe your words...
You glanced at him furtively and saw that he himself was being visually "transformed" by the feminine makeup...
Although the ineptness of the makeup was noticeable, Peter began to look much more feminine...
You felt your tiny cock make a pathetic, unsuccessful attempt to get hard...
You even trembled with "burning" shame...
"What the fuck?! What kind of perverted things are turning me on?! But... The makeup and women's underwear made "Peter's look" so horny... Wait! And what do I look like now?! Like slutty chick?!" - you thought in panic.
To top off the shameful procedures, you and your roommate Peter had to do something else...
Peter, using his smartphone, took numerous photos of himself and you.
"This is for the report... That rich donator needs proof that we're fulfilling the terms..." your roommate's voice sounded confident as usual.
And you simply couldn't even come up with any reasonable objection...
"Squat down, Billy... Good... Now that yoga pose... Look how it's done... Now, the 'on all fours' pose... Excellent! Now bend over slightly and stick your butt out... Done! Hold your smartphone and take photos of me now..." Peter directed you, and you merely passively obeyed his instructions.
In the end, all the photos from this kinky "photo shoot" were sent to that mysterious "patron"-donator.
Two young male students, wearing feminine makeup and only women's panties and bras, posed for photographs that were directed to some pervert...
This vile pervert will probably look at your "sexy" photos and jerk off...
Such thoughts filled you with indignation and shame...
However, beyond the indignation and shame, you felt a growing sexual arousal...
As if the depravity of the situation and your flat chastity cage had multiplied the rate and level of your lust...
A chaos of thoughts, vague images and sensations...

"Maybe I'm a little bit of a... pervert myself... Or maybe these are just extraordinary circumstances... No... It's not my fault after all... I'm a normal guy..." - you thought, while your roommate changed and sat down at the table, intending to immerse himself in his books.
Peter, as usual, was diligently studying for his upcoming exams every day and diligently studying his lecture materials. He also tried to involve you in this activity.
Your gaze fell longingly on the stack of books and notebooks with lecture notes...
That evening, you were no longer able to study with the same diligence...
And Peter noticed the change in your condition.
You had to lie to your roommate once again: you said the reason for your condition was that you hadn't fully recovered from your recent flu.
You went to the bathroom and washed your face with cold water.
It seemed your sexual arousal had waned slightly...
A short dinner...
And soon after, you both go to bed...
Alas, your sleep that night was restless.
The hours of your sleep were filled with vague visions and images, permeated with growing lust and strange, lewd images...

Perhaps the abundance of new information you found online was not at all insignificant and harmless.
A large amount of porn, a multitude of new concepts like "BNWO," "**** feminization," "sissy hypno," "sissy captions"...
If you could soberly and thoughtfully comprehend the situation, the conclusion would be clear: all of this clearly motivates your personality to follow a certain "path of development"...
Tossing and turning in your sleep, you don't realize that your body is profusely covered in sweat, and your lips are twisted in a grimace of lust and thirst for pleasure. Clearly, recent events and your new "streamer" lifestyle have significantly impacted your mental state.
And it seems the situation is developing in such a way that this impact isn't diminishing or even stabilizing...
So, you wake up again in the morning...
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Billy's Sissy Adventures.
Adventures of a young white sissy guy in sunny California and maybe somewhere else...
You are Billy Atkins, a white male student at Hayne College in Hautenville, California.
Updated on Jun 20, 2026
by Trom1806
Created on Aug 21, 2023
by Trom1806
- 2,429 Likes
- 1,132,144 Views
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- 297 Chapters
- 69 Chapters Deep
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