The worst ever sex story ever written ever

Gertrude scowled at Stan while pondering this revelation. Was he really a virgin? Thinking back to those conversations with her workmates, it started to make sense. Gertrude never was good at picking up on sarcasm.

She pulled her hands free from Stan's grip. She had an idea that would scare off even the seediest of Lit wankers.

She moved his hand to her bump, "If you take care of this..."

She put her other hand between his legs "... I'll take care of that".

Stan looked at Gertrude's face. A smirk spread across her lips and he recoiled his hand and he stumbled backwards, away from her grip...
 
In an instant Stan's mighty rod dissolved in Gertrude's grip.

"Aw, shit. Not again," he groaned.

Stan had always prided himself on his majestic dick. All he wanted to do was to prove to at least one woman how glorious it was, but like all the other times, as soon as he got the chance it shrunk and shriveled like a cold cocktail wiener.
 
Stan suddenly felt a strange snuffling at his arse.

He turned round to find Sheila's two rottweilers taking a great interest in his backside and Sheila standing in the hallway, regarding him with gimlet eyes.
 
Gertrude felt a sweaty flush come about her while watching Stan squirm at the sight of the dogs' begging tongues.
 
As the dogs let out a duet of fierce growls behind the now flaccid and quivering man, Gertrude first felt surprise , then laughter, and at last erotic interest as she saw Stan pee all over himself in fear. Watersports got her wet, in more ways than one.
 
(OK, this story is far too funny to be the worst ever!)

The dogs got bored from scaring Stan and seemed to take interest in each other, while Stan and Gertrude watched with interest.
 
Gertrude looked at him lasciviously. "Do my little doggies give you any ideas, my big boy?" she asked breathlessly.

"Are you talking about the hounds or your tits?" Stan replied, then picked his nose. (Stan still hadn't figured out why he was a virgin.)
 
"Don't pick your nose in public you dirty little boy" shrieked Gertrude.

"Bend over at once" she continued, as she grabbed a leash from one of the dog's collars.

"Now see what I'll have to do. I'll have to pull these little trousers down, and then these pants - Christ they're filthy - and smack your 'ickle botty. Yes I will!"
 
Stan's dong dinged sharply as he braced his buttocks for the crack of Gerty's leash upon his crack. He dirfted into a reverie, dreaming of Phuket and how he longed for Chiang to take a chain to his cheeks. But no, Chiang only slapped Stan's butt and shouted "Ride 'em, Cowboy" with each shallow thrust into Stan's dark canal.
Now, though, Gerty would give reality to his fantasy. How he hoped that she had a strap-on, larger and stiffer, far larger and stiffer, than Chiang's yang; how he longed for her to drive it into his rear exit while her babied-belly bounced on his back...
 
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Stan wasn't one for alliteration but even he had to admit his avaricious arsehole and an altogether amourous acceptance of that imagined strap-on, albeit an artificial appendage, made him wet with anticipation.

It was with not a little serendipidity and a massive degree of surprise, both imagined and very real, that Stan cried out as he felt Gerty part his arse cheeks with the tip of something cold, hard, rubbery and, to Stan's untrained chocolate starfish, very wide.
 
It was clear to Gerty that Stan's starfish was indeed untrained, since the "very wide" rubbery item was in fact the rubber ferrule at the end of her uncle's walking stick, which had been left in the hallway.

Finding difficulty even with such a narrow implement she wondered if she should fetch Uncle's false teeth from the glass on his bedside cabinet to give Stan a few "bites" of encouragement on his ample backside. She would have dispensed the bites herself, but the size of her bump precluded this.
 
It was clear to Gerty that Stan's starfish was indeed untrained, since the "very wide" rubbery item was in fact the rubber ferrule at the end of her uncle's walking stick, which had been left in the hallway.

Finding difficulty even with such a narrow implement she wondered if she should fetch Uncle's false teeth from the glass on his bedside cabinet to give Stan a few "bites" of encouragement on his ample backside. She would have dispensed the bites herself, but the size of her bump precluded this.

Stan's buttocks tensed. A natural reaction to the knocking of an uninvited guest. A sound emanated from his throat.

"Oh" he said. The tone one of surprise twinged with excitement.

Gerty placed her hand on his shoulder and leaned in so her lips were almost breathing warm air on Stan's left ear.

"You ever felt enamel on cheek, Stan?" Her words were breathy and sounded menacing.
 
The cold, glossy fire engine red polish of Gertrude's long and curling fingernails slid from Stan's cheekbone to his jawline. He shivered with delight and his anus quivered from a slightly deeper prod from the tip of the cane.

Then with the other hand, Gertrude's nails tore into the skin of Stan's scrawny ass cheek.

Stan let out a cry.

"Oh, Mama! Don't!"
 
LMFAO. This truly is the worst sex story ever. But one of the funniest too.

Well done all, please continue.
 
Gertrude turned to look at Bob with an annoyed look on her face.

"What are you doing home early?" she asked flippantly. "I assume that English teacher gig didn't work out for you?"
 
Gertrude turned to look at Bob with an annoyed look on her face.

"What are you doing home early?" she asked flippantly. "I assume that English teacher gig didn't work out for you?"

He was flummoxed slightly by the impertinence of his wife's question.

Ordinarily it would have been a perfectly reasonable thing to ask him but, as his eyes trained over the scene before him, taking in what? A walking cane? disappearing up the stranger's ass, the question seemed out of context somehow.

"Just what the fuck does my inability to hold down an elementary English teaching job have to do with you shoving that", he pointed incredulously at the cane, "up this guy's ass have to do with the price of cotton?"
 
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