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The Melancholy of Gumball Watterson	By : xXDasXGoochXx Category: +1 through F > Amazing World of Gumball, The Views: 12430 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own The Amazing World of Gumball or any characters associated to the Cartoon Network Show. I make absolutely no money in any form from this work.

Chapter List
- 1-I Feel Numb
- 2-I Feel Pretty
- 1
- 2
I Feel Numb

By xXDasXGoochXx

Gumball stood slouched against a brick wall, eyes half lidded and dull as a midnight draft found purchase beneath his stolen cheerleaders skirt. Currently, he was in East Elmore, a working class part of town that was prevalent with prostitution, gang activities and hard drugs. He was dressed in the white and red cheerleading outfit of his school along with a pair of trainers and one of his mother’s strapped purses.

He shivered slightly questioning his judgment of going commando in november. Yet he had discovered during his fifth go at this that underwear just got in the way and would be dirtied anyway. Within the purse was a pack of kleenex for clean up and box cutters for protection. Not that Gumball actually had the mettle to pull a weapon on anyone but it was a good deterrent anyway.

Gumball inwardly sighed, dead dull eyes scanning for potential customers as he thought about the first time he had done this. He had been desperate, the anguish of watching his mother working 3 jobs and taking out horribly bad loans to pay off Anais’ medical bills when her kidneys had failed due to a sudden case of Chronic Kidney Disease. Desperate to help in anyway he can he had sold everything of value in a foolish hope to make a enough or just help a little. It had been while on the way home from the hospital late at night that they had driven on the road he currently stood next to due to intensive traffic jams. The road was well known to be high traffic for prostitution, he had stared wide eyed at the scantily clad women walking up and down the block as he passed.

That was when the idea came to him. He had already been practicing crossdressing for months and had gathered a dozen outfits hidden carefully within the old clothes within the attic of his home. He had obviously been extremely apprehensive of the idea. That is, until a week later he had while getting a glass of water late at night, his mother sobbing quietly in the dining room. His mind had been made up at that. The next night, he had donned the shortest skirt he had which had been a cheerleaders outfit he had stolen from school months ago. Donning a blonde wig and snatching one of his mother's strapped purses and a box cutter, Gumball had taken a good long look before leaving. Sneaking out of the house had been easy, taking the late night bus had been easier, only earning a dubious look from the tired looking, overweight bus driver. Once arriving at the bus stop, he had quickly made his way to a corner where he had stood awkwardly for 30 minutes before cursing himself at this stupid idea. He was stopped by a pair of flashing headlights from a dark coloured mini van. Steeling his nerves, he cautiously approached the driver side.

The man driving was a balding guy with large glasses and a sweaty nervous disposition. He rolled down the window and seemed to give Gumball a quick once over.

“Uh um, A-Aren’t you a little young miss..”

“Bubble Gum.” Gumball curse inwardly. The name just popped in his head. “I’m 18.”

Gumball knew the man knew he was lying by the disbelieving look on his face. The man seemed to finally decide, as he began rolling his window up making Gumball's heart drop in his stomach.

“W-wait! I’m 16 ok! I-I just need the money! Y-you’ve never been with a teenage b-girl before!”

The man stopped at that.

“How much?”

“F-Five Hundred.”

“What!? Expensive..”

Gumball swallowed.

“I’m 16 mister. T-tighter than older girls. I-I’ll let you stick it in my b-butt..”

Gumball trailed off, cringing inwardly at his own words. The man eyes widened at this before checking his wallet.

“BJ included?”

Gumball nodded reluctantly.

The man unlocked the doors, GUmball taking the cue to hop in, he only hesitated slightly before gripping the purse and hopping in. They drove in silence for five minutes before pulling into a Big Bob’s Burger Joint parking lot that was closed and empty.

The man cut the engine before seeming to gather his courage and placing 5 100$ bills on the dashboard.

“Condoms?”

Gumball cursed inwardly.

“Uh N-no need?”

The man's eyes widened.

“Bareback? That’s great. B-but first…”

He unzipped himself, Gumball's eyes widening at the large - in his opinion- penis. He hesitated, for a moment, before the sight of a sickly Anais barely hanging on steeled him. He didn’t hesitate.

He used the flat of his tongue to lick slowly from the base to the tip before he sloppily took the whole length only gagging slightly as he bobbed up and down.

The taste was bland, the smell musty. Gumball screwed his eyes shut and thought only of his sick sister laying in bed. Luckily for him, the man had a hair trigger and only moments later did he explode in Gumball's mouth. With a groan the balding man coated the back of Gumballs throat, tonsils and the roof of his mouth in slimy, thick and sticky semen.

Gumbal could only gag, willing himself not to puke as he returned to an upright position swallowing the thick salty and bitter baby batter and slightly panting for the effort as he prepared himself for the next part with a heavy amount of dread. He had prepared for this, using electric tape to bind his male anatomy securely to his stoach so even if he did become aroused it would not show in the slightest.

Gumball readied himself, staring as the man's penis became hard again, standing up as if waiting expectantly. Gumball decided if he were to hid his gender from the man, he would need to be on top facing away. This was fairly easy to accomplish with his small frame.

With a bit of maneuvering involving adjusting the chubby mans seat all the way back, Gumball had enough room. Slowly lowering his underwear so that one leg remained within and to make sure the tape didn’t fail, he position himself in the man's lap, feeling the rock hard bulge part his cheeks as it rubbed its underside against Gumball. He lifted his hips up, only hesitating slightl before gripping the hot, wet, fleshy pole, he aimed the glans right at his virgin, tight asshole. At this time, he did pause, knowing hr had already passed the point of no return. Looking at the 500$ he swallowed.

‘For Anais….For Anais...For AN-! “Oh Gooch!”

He had been horribly painfully wrong when he thought that taking it all in one go was a good idea. He bit his lip as gravity painfully worked against him as he slid down the remaining 3 inches with a shudder. He bit his lip hard to prevent himself from screaming as the pain was intense. Ten times worse than his most constipated poop. He could definitely feel something tear and could feel his eyes prickle as tears of pain threatened to spill.

Still not used to it yet, the man was brutally unawares as he griped Gumballs slim waist and slowly began lifting Gumball and thrusting at the same time. This action elicited yelps of pain as he was brutally buggered.

It was the most painful thing Gumball had ever experienced in his 14 years of life. He could only squeeze his eyes shut and ride the waves of pain. The buggering lasted a merely 5 minutes but felt like hours for the young crossdressing cat. With a low groan from the man Gumball felt the hot sticky cum coat his insides in its salty deluge. Gumball, eager to escape the near torture opened the driver's side, grabbing the cash and his bag while slipping off the softening mans dick and shakily landing on his feet. His ass was on fire and his knees shook. Already he could feel the spunk running down his legs. He cursed himself for not bringing tissues, choosing to pull up his panties to dam up the cum. Turning back to the man still stuck in the euphoria of his orgasm, he muttered a quick thanks and quickly hobbled away, deciding he had made enough for that night. He wasn’t going to be sitting for at least a week.

It had been horrible, painful, but mercifully short. He had felt horrible, mentally and physically. Stuffing the money in his purse he had caught the final bus all the while standing as it hurt too much to sit. It got easier over time. After the fifth, he’d gotten the mouth portion down. After the tenth, the pain had lessened and he had started carrying vaseline. After the 15th, he was simply going through the motions. The twentieth and all he felt was numb, the pain no longer mattering.

He didn’t even flinch as the tell tale flashing headlights illuminated briefly. He simply pushed off the wall and sighed, once again steeling himself. This was for Anais, and he would do anything for her...no matter how numb he got.

-End

Another Entry to the Melancholy of Gumball Watterson. Read and Review, It pays the bills...Figuratively of course.
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The Melancholy of Gumball Watterson