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Chapter 29
by
Trom1806
What exactly are you about to see?
Something unexpected appears before your eyes...
"Plap... Slurp... Ohhh... Shlip… Shlop… Slurp... Plap... Slurp... Ahhh..." - the sounds grow louder with each step you take forward.
You carefully close the front door and walk deeper into the room, looking around in surprise towards the source of these strange sounds.
With a flick of your wrist, you flick the light switch: one of the ceiling lamps has burned out, dimming the room.
The sounds don't go away...
A mysterious premonition of something shocking grips your soul...
Your eyes catch a glimpse of someone's silhouette, partially hidden behind the bed...
This person has their back to you and appears to be sitting on the floor.
And this person... makes rhythmic movements up and down, as if jumping slightly and then lowering themselves to the floor.
It resembles some kind of athletic exercise...
You timidly take a couple more steps forward, walking around the bed. "Someone broke into our dorm room?! It could be dangerous..." you think anxiously.
You try to get a better look at this stranger: a slender build, a thin neck, short chestnut-colored hair...
Suddenly, you notice a glint of the dim light from the ceiling lamp...
Glasses!
This guy is wearing glasses!
You realize this isn't a stranger at all – it's your roommate, Peter!
Somehow, he managed to get home from college before you...
But he looks strange and is doing something shocking...
"Dude, what are you doing?!" - you say, stunned, approaching.
You're met with an absurdly implausible sight; you couldn't have imagined it before...
Attached to the floor (with a suction cup) is a pinkish dildo, about 17 centimeters long, with imitation testicles. Your roommate Peter is wearing only a black women's top and black women's stockings.
The rest of his body is completely naked...
Naked, carefully shaved, hairless, sweaty from a strange arousal...
Peter is sweating profusely and periodically lets out drawn-out, lewd moans that sound more like the sounds made by female porn actresses in the numerous porn videos you've seen online.
As for the "squats," Peter crouch again and again so that the maximum possible portion of this pinkish dildo penetrates his lewdly slurping and squelching anus.

You watch, as if mesmerized, at this obscene spectacle: the young guy's anal hole, generously lubricated with lubricant, stretches further with each movement. "Shlip… Shlop… Slurp... Plap... Slurp... Slurp..." - these obscene, kinky sounds are the result of passionate anal sex with a pinkish sex toy, the size of which (17 centimeters) seems simply enormous to you compared to your pathetic weewee.
Of course, right now your puny pseudo-penis is locked in a metal flat chastity cage – but even in its "free" state, the size of your cocklet was something ridiculously small compared to the dildo that, right at this very moment, is repeatedly plunging into the depths of your roommate's thirsty anal hole.
Probably, such thoughts make you feel a growing, obscene, shameful, lustful arousal in your mind...
The fingers of your left hand descend to your groin and penetrate the fabric of your clothing...
Your fingers begin to tug at your tiny testicles.
At the same time, Peter's depraved moans become louder and more intense.
You see him impale his ass on this pinkish rubber dick with frantic energy...
The tender flesh of his sphincter easily admits such a welcome "guest" as this rubber "big guy"...
It truly resembles scenes from porn movies: only instead of a sexy chick riding a huge cock in cowgirl position, it's your roommate Peter!
And now you're in the position of a person merely observing the process of fun...
Your mind conjures up various terms for such persons...
Often, such words have a somewhat derogatory meaning...
Peter seems oblivious to you, his entire attention focused on the captivating process of "dickriding"...
The whites of his eyes roll upward, his body trembles, and drool dribbles from his mouth...
"But why?! Why are you doing this?!" - you say in panic.
A fleeting glance of his lust-ridden eyes...
"I... I need this... I just... I can't take it anymore..." - you could barely make out the meaning of his words amid the lustful moans and the squelching sounds of his stretched sphincter. The frantic fucking continues...
With every movement, Peter's small testicles flutter comically up and down...
The metal flat chastity cage completely blocks your roommate's so-called "male" genitals...
It seems the pinkish dildo is almost completely penetrating her depraved anal hole...
What's happening right now before your eyes makes you feel a surge of mixed feelings: fear and incomprehension, lust and shame, panic and the growth of dark desires in your soul...
You feel your legs weaken and your knees begin to tremble...
"Ohhh... Ahhh... Ohhh... Ahhh... AAAAAHHHHH!!!" - loud moans announced the climax of the lewd dickriding. You notice a trickle of clear liquid squirt from Peter's tiny wee wee, squeezed tightly by the metal of a flat chastity cage, falling straight onto the floor.
The next second, your roommate's exhausted body falls to the floor, right into a puddle of saliva, lubricant, sperm, and precum...
The long pinkish dildo remains almost completely immersed in her plump ass...
You stand there and watch all this, unsure what to do next...
Perhaps, after a while, you'll have to have a conversation with Peter about "what the fuck was that?!"
Hmm... Looks like you weren't the only one having problems because of the chastity cage... But where will all this lead next?
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
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