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Description

Really skirting the edge here with the image. I tried cropping it, but still I hope it doesnt cause any problems...

If you enjoyed this story, consider supporting me on Patreon: www.patreon.com/Dobole

Caption text:

In a dimly lit basement, a wet and sloppy rhythm rang near a computer screen. In its pixels were displayed collages of anime girls, all with impressive chests, all scantily-clad or outright nude. Each picture was cycled through, tossed aside for the next one in the collection of hundreds, by the repeated key press of a pale finger.

While that hand was occupied, its twin was tasked with another continuous duty: repeatedly moving up and down while firmly gripping… something. Appropriate to their appearances, both hands were attached to a pale, sickly, basement-dwelling boy.

“J-Just a bit more now… Hnnng, Asuna really is hot… Ahh, yesss~” Matt grunted as he came for the twelfth time of the evening. He settled in bliss only for some seconds, time was scarce after all. Feeling up his unimpressive penis, he unsheathed a condom from it, making sure to tie it well. Against his better judgment, he brought it to his face, only to grimace as he saw the image of a breast sketched on the cum balloon.

“Ok then, twenty more and I should be good for today. Just twenty more…” Matt sighed, dropping the used condom into a bucket filled with dozens of others. Like an exhausted office worker, he reached for yet another contraceptive to wrap around his rod.

Scroll through images, jerk off, cum in condom. Scroll, jerk, cum. On and on until the dead of night. Though Matt had been somewhat of a serial masturbator, his vices would never reach such self-destructive states, at least not by their own. Indeed, for almost a week the teen was forced into this hellish routine by some very bizarre, very twisted circumstances.

“Gaahh~ Phew, that was a big one! That’s funny, I've noticed it's usually some Chiaki pic that makes me orgasm.” He took a look at the latex sack, shedding a tear at the sight. Stretched out by his semen was the frightened, humiliated face of a woman, one Matt knew very well.

“M-Mom… I'm so sorry, ma, I seriously wish it wasn’t like this.” He cradled the face’s cheek. “God, I can't even imagine how it must be for you.” Without parting words, he dropped the condom besides three others with the same sketched face.

Unfortunately, Matt knew exactly how his mother felt. That girl had been very specific in describing it. No matter which condom he picked, it would be engraved by an image of either mom’s face, breast, pussy, or ass. Once her son impales his cock on it, the woman’s split consciousness would be stimulated by a vivid recreation of the relevant sexual act.

“It’s her puss- er, vagina this time, huh? Ugh, I promise it will be quick… Maybe I’ll use some Aqua art this time.” Just as he picked an exquisite cleavage pic, Matt was interrupted by an incoming call message on his desktop. “Oh no… No, no, no, not you!” Regardless, Matt picked up. He had no other choice.

“Heeey, bitch boy! Watchu doin’?” A shrill voice buzzed through Matt’s speakers. Its owner was a similarly aged girl, a truly gorgeous one. Her pale, blushing face was highlighted by a pearly smile and sapphire eyes, while long, blond hair framed it like an art piece. Below her neck, a loose t-shirt held some truly attractive bulges.

Despite her beauty, Matt was unable to stare at her classmate. “Hey Tammy… I'm busy right now, please call back later.”

“Busy with what, huh? Oh! Ohhh…” Looking downwards, the blonde saw her pants-less chatmate meekly covering his crotch. “Pfffthahahaha! Holy shit, I didn’t think I'd actually see you do it! Bwahahaha!”

“It’s not funny, you bitch!” Matt yelled through tears. “What the hell is wrong with you, just turn my mom back!”

“Hahahaha! Haha… Ha… H-Hey, don’t cry, I thought you liked this! I mean, if you were pervy enough to steal my undies, you’re pervy enough for this, right?”

The youth wiped his eyes, the reveal of his underwhelming genitals causing another rounf of laughs from the screen. He still had no idea what that psycho was talking about. He’d never steal anyone’s panties! He wasn’t even into blondes!

“Jeez, still going? Okay, maaaybe I’ll be a little nice, if you promise to stop bitching!” Tammy smiled to herself at hearing the weeping subdue. “Good boy! Now, I can see that you’re behind on your quota, so why don’t you sit tight and let me help you with that~”

Before he could resume his cursing, or outright mute the call, Matt’s jaw dropped as his tormentor released her breasts from the flimsy shirt. They swung lightly, undisturbed by any cupping, glistening in the pink light of Tammy’s room. Those breasts were like fabled jewels around the school’s gossip, for them to be shown so callously…

Matt’s cock hardened, distorting the image of his mother’s pussy. He grasped the rod harder than ever before and ejaculated with a few strokes. Even as the imprinted vulva bulged with sperm, it took two more servings before the horny teen was totally milked.

“Woah! My tits must be really good if even some pathetic virgin cums that much from them! Like, you could probably use all that stuff to fill two more condoms, ain't that sweet? How many are you into, by the way?”

“F-Four …” The breathless voice of Matt gasped. “Four hundred… twenty six.”

“Just that? Yiiiikes…” Tammy mimicked putting a pair of glasses on. “Let’s see… You’ve got 574 ejaculates to go before you fill up all one thousand rubbers; with two days to spare, that means 287 cummings per day; assuming you get adequate sleep, attend school, maintain a social life–yeah, right– that would leave you with some eight hours for each and every one of your five-hundred-and-seventy-four orgasms!”

“You see, not all of my brains have gone down to my chest! In case you were too stupid to follow along, the conclusions to my analysis are… You’re fucked! See ya, tomorrow, Matty!” The videochat shut off to a black screen reflecting the boy’s despaired face.

Matt slumped in his seat. “D-Don’t listen to her, mom, we’ll get through this! I’ll fill out every single one of you, then it will be time for Tammy’s side of the deal. She’ll pay off, I just know it!”

“…That said, we really do have to pick up the pace.” Matt reached for the sizable pile of his mother.

Description

Really skirting the edge here with the image. I tried cropping it, but still I hope it doesnt cause any problems...

If you enjoyed this story, consider supporting me on Patreon: www.patreon.com/Dobole

Caption text:

In a dimly lit basement, a wet and sloppy rhythm rang near a computer screen. In its pixels were displayed collages of anime girls, all with impressive chests, all scantily-clad or outright nude. Each picture was cycled through, tossed aside for the next one in the collection of hundreds, by the repeated key press of a pale finger.

While that hand was occupied, its twin was tasked with another continuous duty: repeatedly moving up and down while firmly gripping… something. Appropriate to their appearances, both hands were attached to a pale, sickly, basement-dwelling boy.

“J-Just a bit more now… Hnnng, Asuna really is hot… Ahh, yesss~” Matt grunted as he came for the twelfth time of the evening. He settled in bliss only for some seconds, time was scarce after all. Feeling up his unimpressive penis, he unsheathed a condom from it, making sure to tie it well. Against his better judgment, he brought it to his face, only to grimace as he saw the image of a breast sketched on the cum balloon.

“Ok then, twenty more and I should be good for today. Just twenty more…” Matt sighed, dropping the used condom into a bucket filled with dozens of others. Like an exhausted office worker, he reached for yet another contraceptive to wrap around his rod.

Scroll through images, jerk off, cum in condom. Scroll, jerk, cum. On and on until the dead of night. Though Matt had been somewhat of a serial masturbator, his vices would never reach such self-destructive states, at least not by their own. Indeed, for almost a week the teen was forced into this hellish routine by some very bizarre, very twisted circumstances.

“Gaahh~ Phew, that was a big one! That’s funny, I've noticed it's usually some Chiaki pic that makes me orgasm.” He took a look at the latex sack, shedding a tear at the sight. Stretched out by his semen was the frightened, humiliated face of a woman, one Matt knew very well.

“M-Mom… I'm so sorry, ma, I seriously wish it wasn’t like this.” He cradled the face’s cheek. “God, I can't even imagine how it must be for you.” Without parting words, he dropped the condom besides three others with the same sketched face.

Unfortunately, Matt knew exactly how his mother felt. That girl had been very specific in describing it. No matter which condom he picked, it would be engraved by an image of either mom’s face, breast, pussy, or ass. Once her son impales his cock on it, the woman’s split consciousness would be stimulated by a vivid recreation of the relevant sexual act.

“It’s her puss- er, vagina this time, huh? Ugh, I promise it will be quick… Maybe I’ll use some Aqua art this time.” Just as he picked an exquisite cleavage pic, Matt was interrupted by an incoming call message on his desktop. “Oh no… No, no, no, not you!” Regardless, Matt picked up. He had no other choice.

“Heeey, bitch boy! Watchu doin’?” A shrill voice buzzed through Matt’s speakers. Its owner was a similarly aged girl, a truly gorgeous one. Her pale, blushing face was highlighted by a pearly smile and sapphire eyes, while long, blond hair framed it like an art piece. Below her neck, a loose t-shirt held some truly attractive bulges.

Despite her beauty, Matt was unable to stare at her classmate. “Hey Tammy… I'm busy right now, please call back later.”

“Busy with what, huh? Oh! Ohhh…” Looking downwards, the blonde saw her pants-less chatmate meekly covering his crotch. “Pfffthahahaha! Holy shit, I didn’t think I'd actually see you do it! Bwahahaha!”

“It’s not funny, you bitch!” Matt yelled through tears. “What the hell is wrong with you, just turn my mom back!”

“Hahahaha! Haha… Ha… H-Hey, don’t cry, I thought you liked this! I mean, if you were pervy enough to steal my undies, you’re pervy enough for this, right?”

The youth wiped his eyes, the reveal of his underwhelming genitals causing another rounf of laughs from the screen. He still had no idea what that psycho was talking about. He’d never steal anyone’s panties! He wasn’t even into blondes!

“Jeez, still going? Okay, maaaybe I’ll be a little nice, if you promise to stop bitching!” Tammy smiled to herself at hearing the weeping subdue. “Good boy! Now, I can see that you’re behind on your quota, so why don’t you sit tight and let me help you with that~”

Before he could resume his cursing, or outright mute the call, Matt’s jaw dropped as his tormentor released her breasts from the flimsy shirt. They swung lightly, undisturbed by any cupping, glistening in the pink light of Tammy’s room. Those breasts were like fabled jewels around the school’s gossip, for them to be shown so callously…

Matt’s cock hardened, distorting the image of his mother’s pussy. He grasped the rod harder than ever before and ejaculated with a few strokes. Even as the imprinted vulva bulged with sperm, it took two more servings before the horny teen was totally milked.

“Woah! My tits must be really good if even some pathetic virgin cums that much from them! Like, you could probably use all that stuff to fill two more condoms, ain't that sweet? How many are you into, by the way?”

“F-Four …” The breathless voice of Matt gasped. “Four hundred… twenty six.”

“Just that? Yiiiikes…” Tammy mimicked putting a pair of glasses on. “Let’s see… You’ve got 574 ejaculates to go before you fill up all one thousand rubbers; with two days to spare, that means 287 cummings per day; assuming you get adequate sleep, attend school, maintain a social life–yeah, right– that would leave you with some eight hours for each and every one of your five-hundred-and-seventy-four orgasms!”

“You see, not all of my brains have gone down to my chest! In case you were too stupid to follow along, the conclusions to my analysis are… You’re fucked! See ya, tomorrow, Matty!” The videochat shut off to a black screen reflecting the boy’s despaired face.

Matt slumped in his seat. “D-Don’t listen to her, mom, we’ll get through this! I’ll fill out every single one of you, then it will be time for Tammy’s side of the deal. She’ll pay off, I just know it!”

“…That said, we really do have to pick up the pace.” Matt reached for the sizable pile of his mother.