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Chapter 38
by
Trom1806
Hurrying, you run down the stairs, then out into the street...
You have to change plans and face the unexpected...
Ten minutes later, you burst into the college building.
Out of breath from running, you breathe heavily as you step toward the security checkpoint...
One of the guards stops you, not even giving you a chance to approach the metal detector.
A tall, muscular Hispanic man, dressed in a security guard uniform, looks quite familiar to you.
Handsome bronze skin and strong, muscular, hairy arms...
Several old scars on his bald head...
Intent, slightly narrowed black eyes...
A small black mustache and a large, aquiline nose...
Mr. Castillo...
Yes, that's him.
The same guard you were recently **** to "communicate" with because of that... "incident" in the restroom.
Now he looks at you with a mixture of suspicion and disdain.
"Lectures have long since started. And I'm not going to allow careless, truant students into the college building!" - mr. Castillo says in a deep, peremptory tone.
"But, sir... I..." - you mumble.
"You heard me, Atkins! I'm acting in accordance with the college administration's orders. If you're late for the first lecture, come to the next one. And spare me your pathetic whining!" - security guard replies irritably.
The next lecture starts in about two hours...
With a dejected sigh, you turn around and exit the college building.
"Well... I need to do something in those two hours... Like pick up my clothes from the laundry. And also, I need to go to the ATM and withdraw some cash from my account... My smartphone needs repair, and I'm embarrassed to take money from Peter..." - thoughts in your head.
Your clothes, which you took to the laundry a few days ago...
Among these clothes were a pair of light pink lace women's panties, which you stained with sperm from a wet dream...
You recall with shame the recent events, during which you committed one reckless act after another...
Stealing someone else's underwear, which you are currently wearing under your "men's" everyday clothes...
And you did this out of embarrassment in front of your roommate...
If only you knew that day that Peter himself would commit such kinky acts that your "incident" would seem like a mere trifle...
Thinking about such things, you walk along the city streets, illuminated by the rays of the morning sun. Every step you take makes you feel something unusual...
A slight discomfort...
As if a feeling of emptiness in your anus makes you slightly change the way you walk...
You're too lost in your thoughts to notice that some passersby glance at you with amused grins, seeing how your hips and buttocks sway smoothly and girlishly with each step.
Soon, you arrive at the laundromat and pick up a bag of your washed clothes.
Then you turn onto the next street, intending to find the nearest ATM (after all, you need cash to pay for your smartphone repair).
You know of a shop where you can get your smartphone repaired cheaply for cash.
Unfortunately, you'll have to walk quite a distance to get to this shop (several blocks).
Thinking about these plans, you find an ATM ten minutes later and withdraw three hundred dollars from your bank account. Then you walk east through the entire block.
You walk for quite a while…
"So… As far as I remember, this little store was somewhere nearby…" - you think, looking around in confusion.
It seems you could have easily gotten confused and lost…
Now you've entered some unfamiliar, disadvantaged part of the city.
However, you continue to try to find your way back to the desired location, relying on your memories.
You continue walking along the winding streets of this disadvantaged area.
Your hurried steps along the narrow street between tall apartment buildings attract glances…
Disdainful and hostile glances from the locals…
Ugly graffiti on the walls…
Dirt…
Lots of trash…
You're alarmed when you notice nimble and quick rats scurrying around some of the trash cans…
"This place looks like a dump, not a place where people live..." - you think.
Large trash cans are cluttered with garbage, and plastic bags stuffed with trash are strewn right on the sidewalk or near the walls of buildings. Large cardboard boxes (apparently empty grocery packages from nearby convenience stores) are also piled haphazardly here and there.
You look around apprehensively and try to quicken your pace to leave this place as quickly as possible...
Alas, a minute later, due to your haste and inattention, you clumsily stumble over these garbage bags and boxes.
"Ouch!" - you slam your foot on something hard.
It seems one of the large cardboard boxes wasn't empty after all...
"Argghr!!! Fuck! Bullshit!" - a hoarse voice rings out near you a second before a large cardboard box flies away, grazing your face and causing you to stumble back.
You flail your arms awkwardly and fall to the ground, landing on your plump butt in a puddle of mud.
"Damn! I think I've soiled my breeches!" - an afterthought in your head.
At that moment, your gaze catches sight of a figure rising from a pile of cardboard boxes and bags filled with trash.
It's...

It's a stinking, bearded hobo, dressed in dirty, torn rags!
In his left hand is a bottle of some cheap alcoholic draff.
His cloudy gray eyes glare at you with malice.
He takes a step toward you as you sit helplessly on your ass in the mud.
"Fucking motherfucker! Son of a bitch! You stepped on my foot!" - every word carries a disgusting mixture of stinking breath, foul ****, and the nasty smell of a long-unwashed body.
"Sorry..." - you stammer, terrified.
"Shut up, cocksucker! I don't need your fucking apologies, bitch! This is my neighborhood! Everyone here knows and respects me, Gruff Mike! So you're going to pay..." - hobo takes a step toward you, his body looming over you.
Your gaze darts restlessly over the vile, threatening figure.
"I need to get out of here right now!" - is the first thought that comes to your mind.
You're about to jump to your feet and run, when suddenly a mocking, hoarse laugh makes you pause.
"Heh! Heh! Don't even think about trying to run, cocksucker! Or you're in for a nasty surprise! Heh! Heh!" - hobo reaches his right hand into the pocket of his torn, dirty trousers and pulls out something.
A small black… gun!
You felt your entire body tremble with terror…
It's hard to outrun a bullet, after all…
"Could my life really just end now!" - you think fearfully.
"What do you have in that bag, bitch?! Get it here quick!" - hobo's harsh words sound threatening.
You meekly hand him the bag containing your washed clothes.
You're too afraid to utter a word.
"Money?! Do you have any money, you fucking cocksucker?!" - these words are accompanied by a painful kick to your thigh.
"Yes, yes, of course, sir... I'll give it all... Just don't shoot, please..." - you begin to mumble humbly, handing him all your money.
Three hundred dollars in cash.
Everything you recently withdrew from your bank account.
Seeing the money, the hobo clearly brightened.
He takes a swig from his bottle, burps loudly, and looks at you mockingly.
"Can I go, sir?" - you ask, trembling and staring at the barrel of the black pistol.
"Shut up, bitch! I decide when you can go!" - your question seems to have angered Gruff Mike again.
You cowered in fear, afraid to even stand up.
Tears slowly began to roll from your eyes.
The hobo steps toward you and stands close to you, his groin level with your face.
"Now you're going to apologize... Really apologize, cocksucker!" - a hoarse voice exudes mocking laughter.
Then Gruff Mike throws the empty bottle toward the wall of the house.
The sound of breaking glass makes you flinch...
Meanwhile, the hobo lowers his trousers...
A rush of overwhelmingly strong stench makes you cough...
A thick, smelly, and dirty cock dangles in front of your face!
Slap!
Slap!
Slap!
Hobo, laughing mockingly, slaps the head of his thick, veiny cock across your face!
Across your cheeks...
Across your forehead...
Across your lips...
Your face is smeared with precum...
"Suck it, bitch! Otherwise..." - these words, and his finger on the trigger of the black gun, make you open your mouth obediently.
The head of the stinking cock quickly finds its way into your mouth...
However, Gruff Mike clearly decided not to stand on ceremony: his left hand grabs the back of your head, and then he thrusts his hips forward powerfully.
He's simply fucking you in the mouth and throat...
You close your eyes in despair and pain, tears streaming down your cheeks even more abundantly.
With great difficulty, you manage to suppress your gag reflex. The head of a thick cock mercilessly rams the depths of your throat...
"Suck... Suck my cock... Boyslut-cocksucker..." - your ****'s hoarse voice sounds with pleasure at the utter humiliation you're currently experiencing.
Rhythmic movements back and forth...
You're being roughly fucked in the mouth right in the middle of a dirty street in a poor, disadvantaged city neighborhood...
You use the brief moments of respite to breathe through your mouth.
The rest of the time, you're **** to breathe only through your nose.
Your attention is focused on the hobo's stinking cock...
This thick cock... slightly crooked to the left, with a very large, crimson head. Your sphincter... for some reason began to throb slightly...
And also: you felt your tiny cocklet unsuccessfully try to harden a little, but the metal of the flat chastity cage immediately returned this tiny thing to its former insignificant size.
Now you are unable to think rationally; fear dominates your consciousness.
However, beyond fear, there is something else...
Unconsciously, in your current situation, you are applying blowjob techniques you've seen in numerous porn videos on the Internet.
Visual images of lewd sissy sluts sucking big dicks involuntarily arise in your memory...

"Yes... Yes... Lick my foreskin with your slutty pink tongue... Suck... Swallow my cock... Slutty bitch..." - Gruff Mike clearly derives intense pleasure from your efforts. He continues to increase the tempo of his rhythmic hip movements...
Faster and faster, his thick, stinking cock fucks your mouth...
His stinking, hairy balls slap your chin with every thrust.
"You suck my dick well! You're a trueborn cocksucker, bitch-boy!" - you're unable to respond to such comments due to the thick cock filling your mouth and throat.
Everything is so humiliating...
But why, in some peripheral part of your consciousness, does a phrase like "you suck my dick well" feel like a compliment?!
However, now is clearly not the time for reflection – you're too busy and too scared...
Suddenly, the hobo's left hand forces your head to closer and hold still...
The entire thick cock is inside your throat...
And that dick's throbbing starts!
You breathe through your nose, desperately hoping you won't pass out.
Streams of warm cum shoot one after another down the back of your "hospitable" throat of slut-cocksucker.
Cum...
So much cum...
It seems this stinky guy couldn't cum for a long time until he was lucky enough to encounter such a delicious fuck hole like you...
"The taste of this cum is completely different from anything I've ever tasted before - not like my cum, not like Peter's cum..." - a shameful but arousing thought pops into your head as your nose presses against the hairy, stinking pubis.
Cum...
This musky scent, mixed with the stench of unwashed body...
You feel slightly dizzy.
You swallow diligently...
Again and again...
Finally, the flow of liquid dries up and Gruff Mike steps away from you.
You rise slowly, your legs shaking.
Your face is tear-stained and covered in a mixture of saliva, precum, and cum.
Your T-shirt is stained with the same fluids.
"Now you can get out of here, bitch-boy! What are you sitting there for? Or maybe you want to 'service' the other inhabitants of this neighborhood with your lustful mouth? Ha! Ha!" - hobo says mockingly.
You run away in fear as fast as you can...
Ten minutes later, you leave the territory of this impoverished, dirty city-quarter.
Meanwhile, Gruff Mike laughs loudly, holding a small black gun with the partially erased inscription "toy" barely visible on the right side of the barrel...
Soon, tired from running, you stop in the middle of 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
- 1,132,144 Views
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- 297 Chapters
- 69 Chapters Deep
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