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Chapter 37
by
Trom1806
You feel like just a little more... and you'll be able to cum...
Achieving your goal will have consequences...
"Ouch! Ouch! Ouch! Hurts!" - you squealed thinly like a girl.
It seems you were too hasty in pushing that pinkish dildo into your ass...
Too forceful a hand movement was reckless: most of the shaft and the head of that rubber "cock" sank too deeply into your tight anal hole, which was clearly unaccustomed to such a large-scale "invasion."
You move your trembling hand and pull that pinkish rubber thing out of your plump butt.
Lube...
More lube...
You generously lubricate both your throbbing, sensitive hole and the surface of that pinkish dildo.
And...
Another try!

More carefully this time...
Slower...
Gentler...
Push!
Push!
Push!
As your anus gradually... "gets used" to the impressive size of this seventeen-centimeter rubber "dick," you let out quiet, effeminate moans and squeals...
Every tiny part of your body and mind is experiencing the powerful impact of previously unknown and very... kinky sensations.
A rising wave of pleasure mingles with stings of pain, which gradually subside thanks to the lubricant.
The moment the head of the pinkish dildo pokes a hypersensitive spot which deep within your anal hole, you begin to moan and squeal much louder...
At the same time, compilations of sissy-themed porn videos flash before your eyes...
You see lewd visual images of effeminate sissies dressed in lingerie, their pathetic penises caged (like your micropenis).
And some of these sissies are doing the same thing you are now...
Your pupils dilate in shock when you see on your laptop screen the size of the dildo one sissy slut managed to stuff into her slutty ass...

The seductive female voice accompanying the "action" in these videos only adds fuel to the flames of your sexual arousal.
"You've never been a real man..."
"Your asshole is meant for fucking..."
"You're a pathetic sissy whore who will be **** to acknowledge her place in the world..."
Your whole body trembles with lust. A trickle of saliva slowly flows from your parted mouth and drips onto the blanket...
The movements of your left hand again and again make your body feel this voluptuous "invasion" deep within...
Back and forth...
Back and forth...
Back and forth...
The wrist of your left hand is already starting to tire a little – but you simply continue to fuck your own ass with this seventeen-centimeter pinkish dildo!
"Ohhh! Ahh! Ah!!!" - your moans of pleasure sound so... lewd and so girly.
Minute after minute, this depraved "performance" continues.
The room is filled with slurping and smacking sounds.
The head of the pinkish dildo again and again "rams" the hypersensitive pleasure point which deep within your naughty anal hole. Almost all 17 centimeters of the pinkish dildo are buried in the "welcoming" depths of a lubricant-coated, stretched anal hole.
Finally, you experience maximum pleasure with the deepest penetration...
The head of the pinkish rubber "dick" presses powerfully against your "pleasure button"...
Your shameful, girlish squeal fills the room, and simultaneously, streams of liquid squirt from the tiny holes in the metal of your flat chastity cage, staining the palm of your right hand and the blanket on the bed.
You move your right hand back, and the long pinkish dildo exits your anal hole with a wet pop.
The pulsation of your lubricated sphincter now looks so perversely depraved...

And that strange feeling of fullness is gone...
You even feel a little... sorry...
Meanwhile, on your laptop screen, your eyes are seeing stunningly lecherous scenes of perverted sex...
And the seductive female voice continues to utter phrases that seem to instil something and seem to make you even more... horny.
"Natural-born sissy-slut..."
"Your tiny pseudo-penis must forever be in a cage..."
"Your ass-crack will soon get bigger..."
"Filthy sissy-bitch, who will only enjoy big dicks..."
In a state of post-orgasmic relaxation and mental chaos, you slowly bring the fingers of your right hand, covered in your own cum, closer to your face.
Cum...
Your cum...
Continuing to watch porn compilations, you begin to carefully lick the sticky liquid off your fingers.
And then...
You see a cum stain on the blanket and try to clean as much of it as possible with your tongue...
You licked and swallowed the liquid.
The taste of your own cum in your mouth...
It's so strange...
However, you had an even more kinky experience about a week ago: back then, during a stream, you had to taste your roommate's sperm.
But now...
Now what you're doing isn't ****.
Not on someone's orders...
Not because you need money...
Now your actions are based on your own desires.
Or is there some hidden influence at work, the essence of which you're unaware of?
One way or another, you've now achieved your goal and been able to relieve sexual tension.
It took you ten minutes to complete the necessary steps: you turned off the porn on your laptop, deleted your browser history, shut down the laptop, and put it back.
You also put back the pinkish dildo and container of lubricant.
Then you performed your personal hygiene, got dressed, and left the room.
So, now you have to go to your lectures at college.
You glance nervously at the face of your small wristwatch.
Apparently, you're already hopelessly late for your first lecture...
Hurrying, you run down the stairs, then out into the street...
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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
- 1,131,619 Views
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