Jacob met Kayla on Tinder. They went on a date, didn’t really hit it off, and that was that. He figured he’d never hear from her again. And he was wrong. Because that evening, Kayla texted him around 11pm.
“You up?”
“Sure am,” he wrote back.
“Wanna come over?”
“Sure do,” he said, chuckling to himself. How could this have been? A terrible date, a woman he never thought he’d see again. And suddenly, she’s calling him over to fuck? Well. Perhaps it’s because she figured there was nothing left to lose. Might as well get laid.
Jacob jumped in his car and drove to her apartment and headed in. She met him in the lobby wearing booty shorts and a see through tank.
“Hey,” he said, giving her a quick hug.
“Hey back,” she said casually as they got in the elevator. “So …”
“So …” he said.
“I have a request,” she said quietly.
“Oh? What’s up?”
“Give me your hand,” she said.
She took his hand in hers and turned around, guiding his hand into the back of her shorts. He put his hand on her ass cheek.
“Lower,” she said.
He inched his hand lower.
“Lowerrrr,” she whispered.
He inched his finger closer to her asshole.
“Almost there …” she said.
He ran his finger down her asscrack until he hit it. A piece of plastic.
“Is that …”
“A butt plug,” she whispered. “When we get upstairs, I’m going to take it out.”
Kayla turned around and reached out, grabbing his cock in her hand.
“And you’re going to put that. In.”
The elevator dinged and they walked towards her apartment. She opened the door and walked in, slipping out of her clothes. Kayla was short — just around 5’3″, and petit. She couldn’t have weighed more than 105 pounds, but she had great B cup sized tits and a fat ass that jiggled when she walked.
Jacob watched her walk over to the sofa, where she bent over, revealing her asshole. And the pink diamond shaped plug that was inserted firmly into her pink asshole.
“Push it out,” he said, unzipping his pants and walking towards her.
Kayla pushed, opening her asshole until the buttplug slid out and landed perfectly in his hand.
“Open your mouth,” Jacob said.
She opened her mouth. He pushed the buttplug into her mouth and watched her suck and lick it clean.
“Good girl,” he said, stepping closer. He pulled his boxer briefs off. She could feel his erection against her ass cheeks.
“Here,” she said, handing him a bottle of lube that was sitting on the sofa.
“I want to be your anal slut of the evening.”
Jacob popped the lid open and poured the lube, liberally, onto his cock and her asshole. As he rubbed her asshole, he slid two fingers in with ease.
“I want you to buttfuck me into oblivion,” she said.
He nodded. “I will.”
Kayla began to push her asshole open in anticipation. Open. Closed. Open. Closed.
“Please, daddy. Fuck me. Fuck my pink asshole.”
He pushed his cock into her asshole. It slid in slowly. His cock was almost 8″ and, though not thick, it wasn’t pencil thin, either. She gasped as he entered her, his hands on her hips.
“Mmm,” she moaned. “I can feel you. Push deeper.”
He did as instructed.
“God your asshole feels good.”
“Does it?” she asked.
He nodded as he began to fuck. Slowly, at first, but soon, he pounded faster, his pelvis slapping against her ass. After a few minutes, he pulled his cock from her asshole and began to finger her. Two fingers at first, then three. And then, he pulled her asshole apart, gaping it.
“God damn,” he whispered. “You should see this. So perfect.”
“I want to see. I want to see you gape my asshole.”
Kayla reached for her cell phone and opened the camera.
“Here,” she said, handing him the phone.
He took several photos of her gaping anus. And then he leaned down and shoved his tongue into her ass, licking. She reached in between her legs and began to masturbate. She breathed heavier and heavier as her anus gaped open and closed as he licked her clean, pink hole.
“Make yourself cum,” Jacob said.
“I’m gonna,” she said, panting as he tongued her faster and faster.
“Lick my fucking asshole!” She shouted as she began to tremble and shake. “Oh god. OH GOD!”
“Do it! Cum for me! Cum!”
“I am … I — I — ohhh god, oh godddd i’m CUMMIIIING.”
Kayla’s pussy began to drip. Suddenly, Jacob stood and RAMMED his cock back into her asshole.
“OHHHH fuuuuuuuck!!” Kayla shouted as Jacob fucked her ass as hard as he could.
Her anus clamped down over his cock as she squirmed and brought herself to orgasm a second time.
“Give me the buttplug. We’re really gonna stretch your asshole open.”
She threw the plug to him. He pulled his cock from her asshole and guided the buttplug into her at the same time that he pushed his cock into her. Somehow. Some way. Kayla managed both his thick cock AND buttplug at the same time. He noticed her gripping the couch cushions and grimacing, grunting as he double penetrated her. Cock and toy.
“Fuckkk,” she said. “Fuck. Fuck fuck fuck.”
“You okay?”
“Yeah,” she whispered. “It’s so much. It’s SO MUCH.”
“You like it?”
“I love it,” Kayla whispered.
Suddenly, he started to finger her asshole, stretching it even more.
“SHIT!” she shouted. “Deeper! Yes, fucking rip my asshole open!”
He fingered her ass, fucked her ass with his cock, and toyed her ass with the buttplug. Her asshole was stretched so wide she thought for sure she was going to pass out. She trembled.
He pulled his finger, toy and his cock from her asshole.
“Come with me,” he said, leading her into her own bedroom. He threw her onto the bed and flipped her over onto her back. Her eyes were wide. “What toys do you have?”
“Hitachi wand. Dresser.”
He yanked the drawer open and turned the wand on. He grabbed a mirror from her nightstand. Kayla spread her legs wide and then draped them over his shoulders. He hoisted her up a bit and slid his cock into her asshole with ease, watching her eyes pop as he fucked her asshole. He held up the mirror so she could watch his cock slide into her anus.
“Ready?” He asked.
She nodded. He pressed the wand to her clit.
“OHHHHH MY GOD!” She shouted as he fucked her asshole. With his left hand, he held the mirror, with his right, the wand on her clit. He moved in and out of her.
“Let me hold all of this,” she said. “I want you to power fuck my ass.”
He handed her everything, wrapped his arms around her legs and began RELENTLESSLY fucking the shit out of her. She was moaning, her asshole got tighter around his cock. She trembled as she began to squirt uncontrollably all over his torso. He kept fucking. He ran his fingers through the squirt and shoved his wet fingers into her mouth.
“How do you taste?” He asked.
“So good. I’m REALLY gonna squirt. Oh god. OH GOD!”
As she got closer and closer, he fucked harder and harder. Her eyes rolled into the back of her head. She dropped the mirror and grabbed the sheets, crying out. He was so deep. Every inch of him was in her.
“Fuck. Jesus. FUCK! I’m! I’m gonna …”
She fingered herself. He could hear that amazing, sloshing wet pre-squirt sound.
“OH GOD!” She shrieked. “I’m gonna squirt! I’m! I’M! AHHH!”
As she squirted, Jacob yanked his cock from her asshole and leaned in, opening his mouth, which she squirted directly into. She sprayed, filling his mouth, soaking his face and hair. She trembled violently as she came.
“Oh. Oh god,” she whispered.
He stood up. His mouth was full of squirt.
“I want it,” she whispered.
Jacob leaned in to her. Kayla opened her mouth. He spit her squirt into her mouth.
“Drink it,” he commanded.
She gulped.
“I want you to cum in my asshole,” she whispered.
“Come down here and suck me, first.”
Kayla slid onto the floor and wrapped her lips around his cock. She pressed her head against the mattress and nodded. He knew what that meant.
Jacob grabbed her head and began to pound her throat, which bulged as his cock pounded her mouth. Her eyes watered, she gagged, drooling all over her tits.
“Good,” he whispered. “So fucking good.”
He pumped into her mouth. Kayla, just for the hell of it, pushed her asshole open and closed as he fucked her face. She slid a finger into her asshole while he fucked her mouth.
“Get on the bed,” he shouted.
She hopped up, spread her legs and put them onto his shoulders. He slid into her anus and ejaculated deep into her.
“Fuckkkkkkk,” he groaned.
“Oh my GOD I can FEEL YOUR SPERM. I can feel it. I can feel it,” she said laughing. “Oh my GOD you’re still cumming! How?”
“I haven’t gotten off in a few weeks,” he said as he cock continued to pulse and his balls continued to empty into her. Rope after rope soaked her insides.
“You’re! You’re still cumming!!” She shouted, laughing as she felt his cock pulse inside of her.
Finally, he finished. He stepped back and smirked as she exhaled heavily. He pulled his cock from her and watched her anus slowly close.
“Hold your hand out,” she whispered, inching herself to the edge of the bed. Jacob held his hand under her anus as she pushed it open and tilted down. His cum poured out of her asshole, filling his hand and overflowing. He quickly put his other hand under her asshole to catch the spillage. Sperm kept flowing from her.
“Wow,” she finally said. “Wow …”
Once her asshole was empty, he slowly raised his hands up to reveal the huge puddle of sperm.
“Pour it on my face and into my mouth,” she whispered.
Jacob couldn’t believe this was happening. She leaned back and opened her mouth as he slowly brought his cum filled hands over her face.
“Do it,” she nodded, closing her eyes.
He tilted his hands over her face, pouring his warm cum all over her.
“Mmmmm,” she moaned as she licked his cum and swallowed as much as she could. Her face was soaked in cum. She sat up and giggled as cum ran down her cheeks and onto her tits. She opened her eyes, blinking slowly. He held his hand to her mouth. She leaned in and licked and slurped, swallowing his cum, licking his hands clean.
“Good,” she whispered. “You cum a lot.”
He smirked.
“So,” she said. “I’ll call you sometime?”
“Sure,” he said.
And that is the story of Jacob’s worst and best first date ever.
Source: reddit.com/r/sexystories/comments/d6x3bs/butt_fucked_into_oblivion_mf_anal_squirt_creampie
Anal slut of the evening – what a nice thought! Hot story. Well written.