Girls of the 90s read romance novels while boys flipped through dirty mags. That’s why there was such a sexual disparity between most men and women who grew up in the 90s. He’d want to fuck her ass and cum on her face. She’d want a dozen roses, a romantic dinner, and to be swept off her feet.
But girls of the 2000s? They grew up watching porn. Mandy was one of them — so by the time she was 19, she had a wild fantasy and very high sexual expectations.
She met Scott online and they started to fool around. She wanted to do all of the stuff she watched online, which was perfect, because he did, too. Scott was 21, so a little older, but not by much.
Mandy had “granny hair” — dyed silver and tied up in a bun or pig tails. She was skinny, peppy, always giggling. Her favorite outfit was knee high rainbow socks, Chucks, and booty jean shorts. She had green eyes and dimples and was basically as cute AF.
She also had nice medium sized breasts and a cute little butt.
She was taking a gap year and intended to do some light traveling, but was home during the winter for a brief hiatus. That’s when she went online and found Scott.
He came over. They fooled around a few times. Eventually, she sucked him off in the back of a movie theatre. Drank all of his cum like a pro. His eyes grew wide.
“Your the first girl who’s ever swallowed.”
“I don’t mind it, she said. Although you do cum a lot.”
He smiled. “I stay well hydrated,” he joked.
After a few weeks, she felt confident enough to ask Scott what he thought of anal. She wanted to try it. The pornstars made it look easy. The message boards said it was painful.
“Why don’t you buy a few buttplugs?” He suggested. “Small and medium. And some good lube?”
A few days later, a package arrived for Mandy. She ripped the box open, rushed into her bedroom, closed the door, dropped her PJ pants and flopped into the bed. She got warmed up by masturbating and after a while, hoisted her legs into the air, lubed up the small buttplug and pushed it inside.
It felt … okay.
She kept masturbating, occasionally pushing the plug back into her perfect pink asshole. Not very long after, she came. As she pulled the toy from her hole, she felt the sudden urge to go to the bathroom.
Upon a quick Google search, she discovered this was normal.
That night, she was at it again, fingering her pussy, pushing the plug into her asshole. She decided to up the ante and pulled the plug in and out, fucking herself slowly.
She got a dildo from her drawer and pushed it into her bald little cunt and fucked both of her holes at the same time.
She came, pushed the toys inside of herself and snapped a quick selfie for Scott.
“I’m coming over,” he replied.
“Not tonight, buster. My parents are home. But they’re going out tomorrow. Come by at 7?”
7pm the next night couldn’t come fast enough.
Mandy’s nightstand was prepped: On it, the lube, dildo, and two butt plugs.
Scott came over and she decided she was ready for Scott to finger fuck her asshole while he fucked her pussy from behind. She got on her hands and knees and he came up behind her, spat on her asshole, and went to work.
She winced as he fingered her anus.
“Too fast,” she cried out! He slowed down. He reached for the lube and really doused her in the stuff. He grabbed the medium sized butt plug and slipped it in.
She cried out.
“Jesus FUCKING Christ!”
“Should I take it out?”
“No! No, no, it’s in? Leave it in.”
Scott kept pumping away, filling her pussy with his thick cock. She howled with pleasure as he made her cum.
When all was said and done, she pushed the plug out of her ass. It hit the sheets. She was embarrassed — didn’t want him to see the toy that might be a little … dirty.
On the other hand, she’d read a post on a message board that said most guys don’t care if they get a little shit on their cock so long as they get to fuck you in the ass.
“Sorry,” she said as she snatched the toy from the bed and rushed into the bathroom.
Scott followed her. The toy was in the sink soaking in hot soap water. His cock was still hard — he hadn’t cum yet.
“Wanna piss on me?” She asked.
“Sure,” he said.
She stepped into the bath tub and got on her back. He stood over her and fired off a quick stream of warm piss. It splattered off her face, into her mouth, down her chin, and all over her tits.
Mandy arched and pulled her clit back towards herself and peed on Scott. Most of it just ran down her belly, though.
“Can you piss in your own mouth?” He asked.
“I’ll try,” she giggled, and hoisted her legs above her head. “Hold me!” She shouted with a laugh.
There she was, her anus totally exposed, a stream of piss shooting out of her bald pussy and splashing into her own face and mouth.
“Can I?” He asked, pressing his finger into her ass.
“Do it!” She instructed.
He pushed his finger into her asshole.
“Think you’re ready for a cock?”
“No,” she said as she finished pissing into her own mouth. “Your cock is way bigger than those toys. I need to ease myself into it a little more.”
He fucked her from behind until he came. She dropped to her knees and opened her mouth, letting him fire six strings of cum into her mouth. She swallowed it down with ease.
A few days later, a dildo slightly smaller than Scott’s cock came in the mail. She got to work, testing her hole, but it was too big. Too painful.
Tears ran down her cheeks as she tried to push the toy into her ass. Then, she had an idea. She got all of her toys out and pushed the small butt plug inside of herself, where it stayed while she masturbated.
She came, removed the small one, replaced it with the medium one. She came, removed the medium one, and grabbed the large one. She masturbated and, now that her ass was loosened up enough, slid the large one inside of herself.
“Ahhhh,” she whispered. “Christ!”
Once it was all the way inside of her, she masturbated. She fucked her asshole with the toy while she brought herself to orgasm one last time and collapsed into the bed with exhaustion.
She cleaned the toys and texted Scott.
“I’m ready. Tomorrow?”
“Can’t wait!” He responded.
But when Scott arrived, Mandy was a little nervous. Toys are one thing, but a real, thick cock pounding into her from every angle conceivable, was terrifying.
“I’m nervous,” she announced.
“Don’t be. I’ll go slow. And if it hurts, we’ll stop.”
“Well,” she said. “I had two shots of tequila already. And that stuff tends to make me sleepy. So, here’s the thing. We’ll start, but if I doze off, I want you to continue.”
“Seriously? Even if you fall asleep?”
“Yeah, actually, that’s kind of my plan. I’ll pass out and you just go to town. I don’t exactly want to remember my first time as being traumatic and painful.”
“Got it,” Scott said.
Mandy stripped down and sucked his cock. She channeled Jessie Andrews, her favorite pornstar, moaning, gagging, spitting all over him. His cock was sufficiently soaked with saliva by the time she was done with him.
“I’m ready,” she said, slightly sleepy.
She got onto her hands and knees and pressed her asshole up into the air. He grabbed onto her hips and guided himself towards her hole. His cock was so drenched in saliva, he doubted he even needed lube.
He pressed. Nope. He grabbed the lube and poured it on her. He slipped a few fingers inside with ease, guided his cock to her ass and pressed it inside.
It went in slowly. She winched.
“Dammit,” she said, biting her bottom lip in pain.
“You okay?”
“Mmm-hmm,” she said.
“I’m falling asleep, baby. Just go slow until I pass out … kay?”
“Okay,” he said as he began to thrust into her beautiful pink hole. It was tight. Tighter than he could ever imagine. The fact that he hadn’t blown a huge load yet was incredible.
He looked at her. She was dozing off.
“Faster?” He asked.
“Mm-hmm,” she whispered as her eyes got heavier and heavier.
He picked up the speed, fucking her asshole harder. Faster. It woke her up.
“Christ,” she said. “Slow down. You’re going to rip my ass in half.”
“Sorry,” he said.
After a while, she was growing frustrated. It hurt and the pain wasn’t getting any better.
“Maybe, you know what? Powerfuck me.”
“Huh?”
“Just go for it. Fuck as hard and as fast as you can. And for as long as you can. Just get it over with. I’m not falling asleep and it kind of hurts.”
“Okidokie,” he said.
He ramped up his speed and SLAMMED into her ass over and over. She cried out in a weird mix of pleasure and pain.
“Rub your fucking clit!” He shouted out.
Good idea, she thought as she masturbated as he slammed into her over and over.
“Switch positions?” He asked.
She got on her back and held her legs up over his shoulders. He fucked her in the ass, missionary style. She masturbated, cumming two times.
“Ready?” He asked.
“Mm-hmm!”
He slammed into her harder and harder. She cried out. Tears ran down her cheeks.
“Don’t stop, baby!” She yelled as she played with her pussy some more.
“I’m cumming!” He shouted.
“Do it! Fill up my ass!”
He released a load into her, draining himself as she came one more time.
She collapsed into the sheets. He pulled out slowly. A little bit of his cum dripped out before her asshole closed up.
“How was it?”
Mandy smiled and passed out.
Source: reddit.com/r/sexystories/comments/7alvw5/19f_and_buttfucked_into_oblivion_m_anal_oral_piss
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