Dare To Fist: The Story of Fisting a Stranger

By Madame Meta

The idea of fisting a man had never crossed her mind before that night. As she looked over the amused faces of her friends who had just dared her to find a random person in the bar to fist, she couldn’t help but be slightly aroused. 

This game of truth or dare had taken them through one bathroom blow-job, two titty flashes, and a surprisingly pleasant makeout session with the overweight bartender. As her best friends toasted to another tequila-driven night, she scouted the bar for her next victim. 

Then she saw him standing at the bar. He was the type of man that makes straight men question their sexuality. She was usually good at spotting adventurous bi-sexual men and she hoped her sense didn’t fail her now. 

She sauntered over to him, the mental, HD porn sequence of her shoving her entire fist into his ass playing wildly through her mind. She could feel her pussy getting wetter with each step closer. 

He caught her staring seductively.

He turned to greet her lustful gaze. He smiled as she chatted him up and he bought her a drink to entertain her longer. 

She moved through the typical steps of picking someone up at the bar over only one cocktail, and soon they were in a cab on the way to his place. 

His apartment fit him perfectly. There were canvasses and art supplies strewn about the place as if he lived in a constant state of experimentation. 

She couldn’t help but think that she had nailed it when she chose the only person in the bar who would be open to being anally fisted.

He poured her a glass of wine and tried to delicately discuss the idea of anal play and their boundaries. She smugly sipped her wine and said she was game for anything. He smirked and took off his shirt. 

She set down her glass of wine and started walking towards his bed, slowly unzipping her dress before dropping it to the floor and climbing up onto the mattress. 

She turned back and motioned for him to follow her. 

He began to walk towards the bed.

He unbuckled his belt and slurring out something about pussy licking. 

She began to remove her damp panties and spread her legs to invite him to watch her masturbate for him. His jaw dropped and he let his underwear drop to the floor, his cock fully erect already. 

As he climbed onto the mattress, she moved back and quickly shifted to be behind him. He laid down on his back and chuckled. 

“Not so fast, tiger…” he said coyly. 

She dropped her gaze to his throbbing cock as he placed a hand on her head and slowly guided her to suck his dick.

She knew she could try to initiate fisting his ass quite easily while in this position. She sucked him off hard and he threw his back in ecstasy. She gripped the base of his cock with one hand and fondled his balls with the other. 

He moaned as she slipped one finger to the rim of his anus and began to stroke it. She let the saliva from her own mouth drip down his shaft and balls to his anus and pushed one finger inside of him. 

He shuddered with pleasure and she could feel his dick get harder in her mouth. 

The corners of her mouth peeled up into a smile; she now knew it would be almost too easy to fulfill her dare. The power that came to her gave her a high that she had never experienced before. 

He pressed her head into him more firmly, forcing  her to deepthroat his extremely stiff cock.

She was itching to get to fisting him.

She also didn’t want to risk him realizing her plan before she could get him into it. She slowly pushed a second finger into his ass and his penis got even harder. 

He threw his head back again and this time his entire pelvic region began to tremble. She immediately took him out of her mouth and gripped onto his dick, hard. 

He moaned as she slipped in a third finger, now stretching out his anus and causing him to rock back and forth in agonizing, orgasmic throes of pleasure. She was only two fingers away from fisting him and she lingered on the stoking of the inside of his anal cavity with three fingers. 

He was begging to be inside her as she let more saliva drip onto her hand and pushed in her fourth finger. He was so close to cumming she didn’t think she would be able to wait any longer to fulfill her objective. 

His eyes rolled back into his head and he moaned and gasped a plea for release as she pushed her mouth back over his throbbing head. It went down her throat while inserting her entire hand into his ass.

She was finally fisting him. 

His asshole clenched around her wrist as his cum shot into the back of her throat and he wailed in total pleasure. 

His face contorted into agonizing ecstasy and she felt the ejaculate drip down the back of her throat. 

He kept pressing her head into him as each wave of orgasm hit him harder and he kept cumming until he was completely drained. 

The semen began to drip out the corner of her mouth and her eyes began to water as she made a fist inside of him and his cock hardened up completely for one last spasm of orgasm. 

He was crying as his dick fell limp and she removed her fist from his ass and her mouth from his cock. 

She smiled triumphantly while looking down at his completely wasted form. She excused herself to the bathroom and cleaned up. 

Checking her phone, she saw that her friends were waiting for an update. She snapped a photo of her hand in a fist, smeared with the excretions of her encounter, and sent it off as proof. 

She gathered her things and left without saying goodbye as he slept naked in the middle of his bed, looking as peaceful as a baby.