Pegging on Evergreen Terrace

BY : JayDee
Category: +S through Z > Simpsons
Dragon prints: 14433
Disclaimer: I do not own The Simpsons, nor any of the characters from it. I do not make any money from the writing of this story.

Bart’s stag night. An hour of so before dawn broke the 21-year-old groom came round to find he was handcuffed securely to the Evergreen Terrace street sign. He was also wearing only a black thong that had presumably previously belonged to a stripper. Or Milhouse. It was a warm night, but that felt like small consolation as the smell of sick wafted from beneath the sign. Bart had been handcuffed with one wrist to each post meaning he could do little should an early walker find him.

"Ay, caramba!" Bart muttered self-referentially. He was still a little drunk.

"This is how you celebrate marrying my sister?"

Bart, suddenly embarrassed, struggled as he heard the firm voice behind him. It sounded so exactly like his fiancée he first thought it was her, but reasoned Terri wouldn’t refer to herself as her sister. He tried to look over his shoulder, and managed to see the figure silhouetted by the streetlight.

"Hey, this wasn’t my idea! I’d rather have spent the night with Terri."

"You went to a strip club."

"I could barely keep my eyes open by the time we got to the club. My blood must be 90% Duff!"

Bart felt a cold hand slap his hard butt, and realised she wore leather gloves. He could not see , but the purple-haired twin wore high heeled leather thigh boots and a leather corset worn above a special harness. She’d slipped off a trench coat before speaking. He heard the clipping noise as she strapped a large black rubberised dildo into place but didn’t know what the sounds meant.

"Hey, quit it! Can you see a key for these cuffs? I don’t want to spend my married life as an Evergreen Terrace tourist attraction."

"You need to be punished, Bart. You need to know what can happen when you go wild and put yourself at risk like this while the love of your life waits at home for her wedding day."

"What the hell you doing? Leave that thong alone," he paused, "Why am I wearing a thong?"

Bart struggled as best he could, but he didn’t want to risk actually hurting the woman by kicking out forcefully. He found he had little choice but to allow her to strip him of the thong. He did recognise the sound of tape tearing and, seconds later, could only give a muffled expression of his disgust as the sweaty thong was taped into his mouth. He hoped the underwear came from a clean living stripper.

‘What the hell?’ he thought, ‘Sherri’s gone crazy! I’m naked on Evergreen Terrace and old Flanders’ll be out running soon! Oh what the hell is that cold… My butt!"

As Bart squirmed gloved fingers worked slippery lubricant into and around his asshole. His mumbled protests grew more urgent, but were met with only a callous laugh, just like Terri’s when something cruelly funny amused her. The two twins could be so similar, Bart reflected. The fingers moved from his ass, and one slid round for his cock. Bart shuddered as the slimy cold leather wrapped around his soft shaft and began to slowly massage him to erectness. He felt corsetry press into his back, and then nibbling on his ear.

"You know, maybe this punishment won’t be too gruelling… I think you’re going to enjoy this Bart."

Purple hair brushed his face as she straightened and began to work the shaft into his ass. He was tight, but she took it slow and he felt a lot less pain than he feared. As the gloved hand worked his cock he realised it all felt pretty good. Bart shamefully closed his eyes as an appreciative moan filled his ears. He couldn’t see that the dildo harness had inner nubs that pleasured the wearer directly during use. Her hips met his; the dildo was buried as deeply into Bart’s ass as it was going to get, and his cock was dribbling pre-cum freely. He ground his teeth into the panties.

"Tell me how much you love Terri."

Bart’s reply was muffled but she could just about understand the depth of love he tried to express. She worked her hips to move the dildo pleasurably as he spoke.

"Keep telling me!"

Bart opened his eyes and looked towards the sky. There had to be something kind of sissy about taking a big rubber cock in the ass, he thought, he damn if it didn’t feel good. The physical sensations of the thrusting dildo and the skilled fingers were getting his nuts good and boiling. He just wished he were with Terri instead of her sister. It was Terri he truly loved, for she had little differences with Sherri that only he ever saw.

‘God, Sherri’s going to get off,’ Bart thought as the moans behind him rose in pitch and intensity.

"I Love Terri! I want Terri!" he cried into the gag, a collection of vowels as his cock jumped and spurted into the dirt and sick beneath the Evergreen Terrace sign. The purple hair dropped down by his face again as she collapsed onto his back, lost in her own peak. The cuffs bit into Bart’s wrists as he supported her weight Her feverish panting felt hot, but at least her breath was sweet, just like Terri’s. He dripped a final load as the dildo shaft moved against his prostate. She ripped the tape off, and separated it from the thong. Broken voiced, Bart asserted,

"I love Terri. I would never do anything to hurt her."

"I know."

He grimaced as the dildo pulled from his ass. She gave him another swat on the buttocks, and helped him back into the thong - it was a stag night, after all. A semi naked groom in the street was to be expected.

"See you at the wedding, Bart."

Terri slid her coat on and strode away, wondering when her dear fiancée would figure out the truth; probably the next time.

A/N: Story written for AFF forum weekly prompt 9 - Evergreen.

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