Trying Something New

"Olivia!" Olivia jerked her head up from her phone at the sound of her name and smiled at the sight of her friend Mia approaching her.

"Hey Mia!" she said, sliding her phone into her back pocket. The girls hugged.

"God, how long has it been?" Mia asked.

"Since before winter break, so at least two months," Olivia said, opening the door of the restaurant.

The girls chatted while the hostess grabbed the menus and led them to a table. They talked about their winter break, catching up while they waited for the waitress to take their order.

Mia and Olivia had been best friends since they were roommates freshman year. They had both moved off campus sophomore year to different apartments, but they had stayed friends and made an effort to catch up every few weeks.

The waitress arrived to take their order, and they paused their conversation to order.

"God, I hate college guys," Mia said after the waitress left.

"Preach," Olivia said, raising her water glass for emphasis. Mia laughed, rolling her eyes.

"But seriously, you'll never believe what Tom asked me the other day."

"What?" Olivia asked, leaning forward in curiosity.

"So, Tom and I have been together for, like, forever, and we've been sleeping together for two years at this point, and he told me the other day that he thinks things are getting a bit... well, a bit boring. So, I asked him if he had something that he was thinking of trying to shake things up, and you will never believe what he said."

Olivia raised her eyebrows, and Mia took a deep breath and leaned forward closer to Olivia.

"He told me that he wanted to try... anal." Mia whispered the last word, and Olivia's mouth fell open in surprise.

"What?" she asked, shocked. Mia nodded furiously.

"Yeah, his solution to our 'boring' sex life, was sticking his dick up my fucking ass. I just about broke up with him."

"That's crazy," Olivia said, wrinkling her nose.

"It's so crazy. And when I got on him for it, he told me that every man wants to try anal, so I shouldn't be that surprised."

"Are you kidding?"

"No! I mean, has Sam ever brought it up to you?"

"No!" Olivia told her, without hesitation.

Olivia and Sam had been together for nearly a year, and they enjoyed a healthy, regular sex life. Sam had never brought up the idea of trying anal, and Olivia immediately began to wonder if Tom was right and every guy did want to try it.

"Well, lucky you," Mia said, shaking her head. "I mean, it's so disgusting!"

Olivia nodded in agreement, but she was surprised to realize that as disgusting as the of anal sounded, she was also curious about what it felt like. She pushed the idea aside, trying to ignore it. She smiled at Mia, changing the subject to talk about the protest on campus, and the girls enjoyed the rest of their dinner, but Olivia couldn't help but notice the feeling of curiosity growing inside of her.

--

Later that night, Olivia lay in bed with Sam watching Netflix. She was only half paying attention. In her head, she was still mulling over the conversation she had earlier with Mia. After the show was over, she rolled over onto her belly to bury her face in the pillow.

"What's up?" Sam asked, stroking her hair. Olivia propped herself up on her elbows to look Sam in the eye and chewed on her lower lip, trying to work up the courage to ask her question. She ducked her head in embarrassment, resisting the urge to bury herself into the blankets.

"Um, I met Mia for dinner today... and she told me something her boyfriend said, and I was curious what you thought..." Olivia trailed off, and Sam raised his eyebrows.

"What?" he asked, shifting on the bed to put his arm around her and stroke her back slowly.

"Well... he said that every guy wants to try... um... anal." Sam let out a surprised breath, laughing a little at Olivia's obvious discomfort.

"Seriously?" he asked, and Olivia nodded. "Huh. Are these the kinda conversations women have? I gotta admit, it's unexpected, but I've gotta try to get in on this." Olivia swatted her boyfriend, rolling her eyes at his teasing.

"I'm serious. Is it true? Does every guy want to try... you know."

Sam sighed heavily, rubbing his jaw as he thought about it. Olivia sat up to look at him, wrapping one of the blankets around her.

"Well, I'm not gonna lie, it's definitely crossed my mind. Whether or not every guy wants to, I don't know, but I wouldn't say no if the offer was on the table."

"Really?" Olivia asked. Sam shrugged.

"Do you want to?"

Olivia opened her mouth, ready to say no and tell him that he was disgusting, but she quickly snapped it shut. The truth was, she wanted to. She was curious what it might be like, and how it would feel, and Sam, sweet and kind, was the perfect person to try it with. The biggest thing holding her back was the voice in her head, that sounded weirdly like Mia, telling her that it was nasty, and she was gross for even considering it.

"Well... I don't know," she said softly. Sam's eyebrows shot up, and he stared at her in surprise.

"Wait, seriously?" he asked. Olivia threw up her hands.

"I mean, yeah. I kinda want to see what the big deal is, but at the same time, it's... dirty."

Sam studied his girlfriend for a long moment before nodding slowly.

"Okay. Okay. Look, I'm not gonna pressure you into anything. I would absolutely love to try it with you, and I think we would have a lot of fun, but it's up to you."

Olivia thought about it for a long moment, weighing the two voices in her head.

"Okay," she said, looking Sam in the eye. "Let's do it."

Sam's mouth fell open, but he closed it quickly, smiling broadly at her. He moved over to the other side of the bed to rummage around in his nightstand. He came up with a bottle of lube, and Olivia's cheeks reddened at the sight of it.

"Right now?" she asked, and Sam laughed at the look on her face.

"I mean, we don't have to, but why not? The plan tonight was to Netflix and Chill anyways."

Olivia thought about it for a moment before nodding slowly.

"Okay," she said nervously. Sam studied her for a moment before turning back to the nightstand. He dug around in the drawer for another moment, and when he turned back he had Olivia's vibrator in his hand.

Olivia took it from him gratefully. She sat up more in the bed to pull her dress off, and Sam did the same. Olivia reached behind to unhook her bra, and Sam's eyelids lowered in appreciation of her bare breasts.

Olivia was a pretty girl. She had long, curly brown hair, and a sweet round, freckled face. While she liked her face, she was more insecure about her body. She wasn't by any means fat, but she was curvy, with D cup breasts and a thick ass on her short 5'4" frame. Despite Olivia's distaste toward her body, Sam delighted in his girlfriend's delicious curves.

As Olivia tossed her bra to the floor, Sam reached forward to cup her right breast. He stroked her nipple with his thumb, and it hardened under his touch. Leaning forward, Sam kissed Olivia. Olivia nipped at his lower lip, and he moaned appreciatively.

Olivia's worries quickly evaporated as she made out with Sam, and she lost herself in the pleasure of being with him.

Dipping his head, Sam caught her left breast in his mouth, sucking it lightly. He pinched the other nipple, and Olivia inhaled sharply at the sensation. Warmth began to build between her legs.

After a few more moments of sucking, Sam lifted his head from Olivia's breast to kiss her again, and Olivia pushed his shoulder so he rolled onto his back. She straddled him, and she smiled at the feeling of the hard bulge pressing up into her. She dipped her head down to kiss his neck, and Sam's hands stroked down her back to cup her ass and squeeze.

Flicking her tongue against his skin, Olivia kissed down Sam's neck and throat, moving down toward his belly. She lifted her head to unbutton his shorts, and she tugged them down his thighs. She pulled his underwear off and tossed it onto the floor, and she glanced up to smile at her boyfriend.

Where Olivia was short and curvy, Sam was tall and thin. He was about 5'9" and was naturally slender with a hint of muscle to his wiry frame. He had wild dark hair and warm brown eyes. He smiled at Olivia and watched as she dipped down to wrap her lips around his hard cock.

Olivia sucked hard, and she reached one of her hands down to cup his balls in her hand. Sam slid his hands into Olivia's hair. He let out a groan, and Olivia began to suck, bobbing up and down on Sam's dick while gently massaging his balls with one hand.

"God, you are so good at that," Sam told her, and he slowly pulled her off him.

Olivia crawled up the bed to kiss him again, and Sam sat up to pull her panties down. He looked around the bed, and, finding the vibrator, passed it to her.

"Play with yourself," he said, his voice thick with lust.

Obediently, Olivia pressed the on button and pressed the vibrator to her clit. She closed her eyes and moaned at the pleasure that spread through her body. Sam watched, stroking her legs as she rubbed the vibrator against herself.

Olivia rocked her hips against the vibrator and wiggled a little as tension began to build deep in her belly. She suddenly jerked in surprise as she felt something pressing against her asshole, and she opened her eyes to see Sam pressing his lubed finger against her.

"Relax, I just want to get you warmed up a bit." She nodded.

Sam pressed his finger harder against her, and her asshole stretched around it. Olivia squeaked in pain at the sudden feeling of something in her ass, and Sam stroked her thigh gently.

"Relax," he murmured, and Olivia exhaled slowly, trying to accept his finger into her. He slowly pushed his finger deeper into her, and she rubbed the vibrator harder against her clit, trying to balance the pain with pleasure.

Sam pulled his finger out, then pushed it back in, slowly beginning to fuck her asshole. Olivia began to get used to the sensation, and the pain began to transform slowly into pleasure.

Just as Olivia felt that she was used to having Sam's finger in her ass, she felt more pressure against the entrance of her ass. Pain began to burn inside of her again as Sam added another finger, and she whimpered in pain.

"You are doing great," Sam said. Olivia breathed deeply, trying hard to ignore the pain to focus on the pleasure of the vibrator steadily rubbing against her.

As Sam began to steadily move his fingers in and out of her ass, Olivia began to feel the tension building in her legs and belly again. Olivia felt herself getting closer and closer, and just as she began to think that she was going to cum, Sam pulled his fingers away.

"What?" she protested, and he smirked at the look of disappointment on her face.

"Oh, I'm sorry," he said, his face full of mischief. "Were you enjoying yourself?"

Olivia bit her lip, feeling a strange mix of emotions building inside of her: disgust at how dirty she was being, happiness at how much pleasure the experience brought her, disappointment at being robbed of her orgasm, and desperate for more.

"Please don't stop," she said softly. Sam kissed her deeply before pulling away to look at her with a heated look in his eyes.

"Get on all fours," he told her, and Olivia obeyed.

Sam knelt on the bed behind her, stroking her ass with one hand and pushing two fingers of the other back into her asshole.

Olivia moaned at the feeling of being filled again, and she rubbed the vibrator faster against herself. Sam steadily began to pump his fingers in and out of her again, and Olivia leaned back into him. She twisted her fingers into the sheets, squeezing her eyes closed with pleasure. The tension began to build again.

Just as Olivia was reaching the point of no return, Sam removed his fingers again. Olivia turned, ready to snap at him, but she stopped when she felt the head of his cock nudging against the entrance of her ass. She gasped as it popped in, and she let out a groan at the sensation of Sam's cock stretching her ass open.

"Oh my god," she said, and she pushed herself back toward Sam, impaling herself on his thick rod.

"You feel incredible," he murmured. "Your asshole is so fucking tight." He pulled out slowly until only the tip was inside of her, and just as Olivia was worried he was going to fall out, he thrust into her hard. Olivia let out a moan, surprised at the sudden sensation of Sam's cock filling her. It was both painful and pleasurable, and Olivia was surprised by how easy it was to relax into the experience.

Sam grabbed Olivia's hips, and he began to saw in and out of her. Olivia pressed a button on her vibrator, and it sped up. The tension returned, and Olivia knew that she was going to cum if Sam continued.

"Sam," Olivia whimpered, and he began to fuck her harder.

"Cum for me baby," he told her, and Olivia's muscles clenched and released, and she came. Olivia let out a long moan of ecstasy, and Sam rubbed her lower back soothingly. A wave of absolute relief washed through her body. She moved the vibrator away from her incredibly sensitive clit, and she let out a sigh of complete happiness.

Sam, working for his own orgasm, continued to steadily pump in and out of Olivia's ass, and Olivia held up the vibrator to turn it off. Olivia, full of post-orgasmic relaxation, began to realize that the pain of being ass-fucked was beginning to grow. Without the vibrator, the pain greatly outweighed the pleasure, and Olivia realized that she wouldn't be able to continue for much longer.

Sweat dripped off of Sam onto Olivia's back, and she squeezed her eyes shut, desperately trying to ignore the pain beginning to radiate from her asshole.

"Sam," Olivia said, her voice tight with pain, "I don't think I can go for much longer."

"Hold on," Sam grunted. Olivia knotted her fingers tightly in the blanket, struggling to hold on.

"Please cum," Olivia begged, and Sam, holding firmly onto her hips, began to fuck her faster. Just as Olivia was about to beg for him to stop, Sam came. He let out a long groan and slowed, and Olivia felt the strange sensation of his cum shooting deep into her asshole.

Sam pulled out of her and fell onto the bed, breathing hard. Olivia moved over to him to nestle against his chest, and he lifted his hand to stroke her hair.

"God that was good," he told her, and Olivia smiled.

"That was actually pretty fun," she admitted. "It was definitely hurting a lot at the end though."

"I noticed. Sorry about that. Next time, we'll use more lube," Sam told her.

"'Next time?'" Olivia asked teasingly. "What makes you think there will be a 'next time?'"

Sam shifted to look her in the eye and raised an eyebrow.

"Do you not want to do that again?" he asked, his voice tinged with disappointment.

Olivia smiled at him, leaning forward to lightly kiss him.

"I definitely want to do that again," she said, and Sam's face brightened.

"How about tomorrow?"