My Roommate's Sister

Checking his pockets and belongings one more time, Mason made sure he had everything he needed before heading out. Car keys, wallet, cell phone, a full water bottle for the car ride, three condoms and an extra sweater for Leni in case she got cold.

Leni and him were going to be meeting in San Antonio. It was just over an hour drive for her and about an hour and a half for him. It was the first time they would be seeing each other in person since Thanksgiving and he couldn’t wait. He would drive all the way to St. Petersburg for her, but she insisted on meeting him at least part of the way.

They had agreed to leave as early as possible so they could spend the entire day together so even though the new semester had started and Mason was waking up every day for class at six, he happily woke up early again to be on the road by 7:30 AM.

Just as he was slipping into his sweater to head out, the door to his dorm opened and Josh walked in, wearing the same clothes he had been wearing the night before when he went out to the local night club.

“Are you leaving?” Josh asked him. He pulled his phone out of his pocket, checking the time. “It’s 7:21.”

“Yeah, I’m spending the day with an old friend of mine in San Antonio,” Mason told him, trying to sound believable.

“Oh cool,” Josh said, striding past him to go to his own bed. “What friend?”

“You don’t know him. He’s an old friend I reconnected with when I was home at Christmas. He’s in Florida doing an internship." Mason had come up with the lie a few days ago, knowing he’d need an excuse he was going to San Antonio so much in the next few months.

Josh didn’t even look up at Mason from his phone. “Nice. Well, drive safe and have fun.”

“Thanks,” Mason said.

As she shut the door to the dorm, he looked at his friend, still looking at his phone. He hated lying to Josh, he was his best friend after all. He really hoped it wouldn’t be much longer before Leni and him told Josh what was going on.

“So, I told my mom about us,” Leni told Mason. Mason’s head shot up and he looked towards Leni in shock.

Leni and Mason had arrived in San Antonio around nine. After a long reunion of hugs and kisses, they walked over to a small diner for breakfast. After they ate, they decided to leave Leni’s car parked in a lot while they drove around the city in Mason’s car, checking out different local shops.

After hours together, going in and out of stores, laughing, kissing and holding hands, they settled into a booth at a restaurant to enjoy dinner before making the drives back home. Mason had barely started looking over the menu when Leni dropped this information on him.

“You did?” he asked.

Leni nodded.

“What did you say to her?”

Leni leaned back in her chair, looking directly at Mason.

—

Leni was sitting at her desk, reading over her school notes when there was a knock at the door. As she turned to see who it was, the door opened and her mom stepped in.

“Hi Hun,” Carrie said, smiling. “Just dropping off your laundry.”

Leni smiled back. “Thanks mom.”

Carrie placed a white laundry basket, filled with folded clothes on Leni’s bed, then began walking out of the room.

Leni and Carrie had always been very close. Even though Leni was very young when Carrie married Brian, she always took care to make sure Leni was comfortable being around Brian and his son. Even after they married and they became a blended family, Carrie always made time for her daughter. They went out, just the two of them, at least once a month. When Peter and then Sarah were born, Carrie always still made sure to show Leni she was loved in this family.

Leni loved her mom very much and for as long as she remembered, she told her everything. Really, there was only one thing Carrie didn’t know.

“Hey mom,” Leni said, before Carrie made it to the door. Carrie stopped and looked at her. “Could I talk to you for a minute?”

“Of course, sweetie.” Carrie took hold of the door and closed it, leaving them alone in Leni’s room, then sat down on Leni’s bed, facing her daughter. “What’s up?”

Leni turned in her chair so she was also directly facing Carrie as they spoke.

“I really want to tell you something, but could you promise me you won’t tell Brian or Josh for right now? I’ll tell them eventually, I’m just not ready to tell them yet.”

Carrie’s eyes narrowed in confusion. “Okay, I promise. Is everything okay?”

“Yes, everything is great,” Leni assured her.

Leni looked down at her hands for a moment, trying to come up with the words. Carrie kept her eyes focused on Leni, waiting to hear what she had to say.

“Do you remember Mason?” Leni finally asked. “Josh’s friend that came for Thanksgiving weekend?”

“Yes, I remember him.”

Before Leni continued, she had to mentally remind herself of how supportive her mother had always been to her. Leni told her everything and not once had Carrie ever put her down for the things she had done. Whether it was when Leni told her she had sex for the first time, or hooked up with a guy in a hot tub. Carrie only ever wanted to make sure her daughter was doing things safely, and that she was happy.

“When he was here for Thanksgiving,” Leni confessed, “him and I hooked up a few times and now we are seeing each other long distance.”

Carrie stared at Leni for a long minute, clearly not expecting to hear this at all.

Finally, after what felt like an hour to Leni, Carrie spoke.

“When you say that you ‘hooked up,’” Carrie asked, using air quotes, “you mean?”

“I snuck down to the guest room every night he was here,” Leni clarified. “I would sleep in the bed with him, sneak back up to my room before anyone else woke up. Then the last night he was here, we had sex.”

“Wow,” Carrie said. “I guess I was way too busy that weekend to even notice you thought he was cute or see you two flirting or anything.”

Leni shrugged. “I think we just tried to hide it because we didn’t want Josh to notice.”

“So he doesn’t know about any of this?” Carrie asked.

Leni shook her head.

“Is that because he tells Patrick to leave you alone and not ask you out?”

Leni shrugged again. “Josh has always been kind of protective about who I date. I know he hated James and he has done everything he can to keep Patrick away from me. But, I really like Mason and he is nothing like either James or Patrick. I don’t know, I’m just worried he would get really protective and tell Mason he can’t date me.”

“Josh may only be your step-brother,” Carrie said, “but he loves you like a real sibling. He cares and worries about you. He doesn’t want you to be with someone who hurts you. But I think the most important thing is that he wants you to be happy.” Leni looked up at her mom. Carrie was smiling at her. “Does Mason make you happy?”

Leni smiled and nodded. “He really does mom.”

“Then I’m happy for you too.”

Carrie stood up from the bed, walked across the room and gave her daughter a hug.

“I really liked Mason,” she told Leni. “He seemed like a really decent guy.” Leni smiled knowing Mason really really was. “I won’t say anything to Brian or Josh for now, but you can’t keep it a secret forever,” she reminded Leni. “Espeically if you get accepted to their school in the fall.”

“I know,” Leni agreed.

—

Mason stared over at Leni, listening to every word of her story of how she told her mom about they were dating. Hearing Leni talk about the relationship she shared with her mother made Mason a little jealous. He never felt that comfortable with his own parents. He had four brothers back home and the only one who he told about Leni was his brother Aaron, and that was only because he walked in on Mason talking on the phone with Leni.

“Sounds like she took it really well,” Mason commented when Leni finished her story.

Leni shrugged. “I knew she would. She’s always told me that I can always be honest with her about sex and stuff. She thinks it’s important that it’s not a secret or a taboo topic so that she can give me informed options on how to be safe.”

Mason really liked Carrie when he visited, but he liked her even more now and respected her as a mother.

“And she’s okay with us dating?” Mason asked.

“She’s very okay with us dating,” Leni smiled.

After dinner, Mason drove back to the lot they had left Leni’s car in. It was a little after nine and Leni was instructed to be home by 11. She still had an hour drive to get back to St. Petersburg, so they had a little time left, but Mason didn’t want her to feel rushed on the highways.

The lot was almost completely empty when they arrived back to it, parking beside Leni’s car. Mason put his car in park, then looked at Leni.

“I had an amazing day with you,” he told her.

“Me too,” she said.

“When do you think we can meet up again?” Mason asked.

“Umm, I’m not sure,” she replied. “I’ll have to look at my calendar when I get home. See when I have tests or projects due.”

Mason reached his hand across the middle cupholders and took Leni’s hand in his. “When will you find out if you were accepted to U of F?”

“Hopefully soon.” She looked up from their joined hands into his eyes. “I can’t wait to not be long distance with you.”

Mason smiled, slowly leaning into her. “Me too.” He leaned across the middle console moving closer to Leni and she scooted in her seat, meeting him half way.

Their lips met and Mason held onto her face. They both moved as close as they possibly could to each other, but the console still separated them.

Without breaking their kiss, Mason opened his eyes to look at the time on the dashboard. It read 9:08.

Slowly, he pulled away from Leni’s lips, though she continued kissing his face.

“What time do you need to start driving home?” he asked her.

Leni turned her head to also look at the clock. “I have some time,” she told him.

“Do you want to get in the backseat maybe?” he asked her.

Leni looked to the backseat of Mason’s car. He drove a Mazda CX-5, a small SUV, so there was room in the back for the two of them. It would be a little tight, but at least they could be fully touching each other. She turned her head back to Mason and nodded her head.

They each went out their own door then climbed back into the car from the back seats. Mason sat back and grabbed for Leni, pulling her onto his lap. She settled on his lap, straddling him, then immediately began kissing him again.

This was already much more comfortable than the front seats. Leni was able to press her body against Mason’s and grind herself against his groin as they made out. She wrapped her arms around his neck and moved her body up and down against his. The friction was making Mason so hard.

Leni was wearing a jean jacket so, slowly, Mason slipped it off her shoulders, pulling it down and off her arms. Underneath, she was wearing a thin red tank top. When she pressed her chest into his, he could feel her hard nipples as they poked into the fabric.

It wasn’t long before Leni was able to feel his erection stabbing her through Mason’s jeans.

“Should I slow down?” she asked him.

“God no,” he gasped out. “Don’t slow down at all.”

Even though he told her not to slow down, Leni pulled back slightly. “Maybe we should slow down,” she said softly. “I didn’t bring any condoms with me.”

Mason grinned towards her. “That’s okay, baby. I did bring some.”

Leni’s face lit up. “You did?”

Mason nodded. “I always come prepared,” he teased, winking at her.

Leni looked out the car windows. The only other car parked in the lot was hers. They were completely alone.

“Do you want to?” she asked him. “In here?”

“I want to do it with you anywhere you want,” he told her.

Leni pressed herself back into Mason’s body and smothered his lips with hers. Now without needing to slow down, she ground herself hard against him. She pressed herself down onto his erection, rose up slightly, just to push down again.

“Fuck Leni,” Mason breathed into her mouth. “You’re driving me crazy.”

“Good,” she said, closing her mouth on his again and pressed her breasts against his chest.

He was so hard and the way Leni kept touching herself to his body, he felt like a teenager about to explode in his pants. “Jesus Christ, Leni,” he said again. He pulled away from her slightly. “You got to get one of those condoms,” he told her. “They are in the glove compartment.”

Leni climbed off him, turned her body and leaned into the front seat of the car. While she reached to open the console up and search for the condoms, Mason undid his jeans. He lifted his ass up slightly to push his pants and boxers down his legs, and his cock sprang free. Leni returned to the back seat with the condoms in hand and saw Mason had his length out and ready for her.

“Here,” she said, handing him the packets. “Get one on.”

Mason took them from her, and immediately ripped one open. As he took it out of the foil packaging and began rolling it onto himself, Leni pulled her panties off her legs. Though she wasn’t 100% sure what would be happening this evening, she was happy she had chosen to wear a long black skirt today. She was able to pull her panties off completely but leave the skirt on so she wasn’t totally naked. She tossed her panties onto the seat beside Mason then hiked up her skirt. Mason was able to get a small glimpse of her pussy as she pulled on the fabric.

With his erection wrapped in the condom, Leni straddled him again. She placed herself slightly above his tip and hovered over him.

“You ready?” she asked him, teasing the tip with her pussy.

“Oh my fucking God, Leni, please,” he begged.

Dropping down, Mason’s cock went deep into her.

“Oh God,” Leni moaned, feeling him fill her up.

“FUCK!” Mason groaned loudly as he felt Leni’s tight pussy lowering onto him.

Leni began grinding herself into him, moving up and down on his length. She braced herself on his shoulders, using them to help pull herself up then push back down.

As Leni rode him, Mason lifted her tank top and pulled it off her arms, leaving her in just a white bralette from the waist up. The fabric of the bralette was so thin Mason could see the outline of her pink areolas and her hard nipples stuck out. Raising up his hands, he held her breasts in his hands, squeezing them and pinching her nipples through the fabric covering them.

“Ohhh,” Leni moaned. “I love when you play with my nipples,” she told him.

Sliding the cups of the bralette to the side, Mason exposed her nipples. They were hard little pink beads, centered on her perfect round tits that bounced as she continued riding him. He stared at them for a long time, circling them with his thumbs and pinching them every few seconds.

Leni raised herself up, holding herself on the tip of Mason’s cock and slowly rotating her hips there. She made that motion for a minute until Mason pleaded for her then she dropped back down on him. A guttural moan escapes out of Mason’s mouth and he threw his head back on the car seat.

“Jesus fuck!” he cried out.

Giggling, Leni attempted to do this again, but Mason dropped his hands to her waist and held her there.

“Don’t fucking tease me like that again,” he warned her. “You do that again and I’m going to cum into you so fucking fast.” Leni laughed again and started bouncing rhythmically on him.

She continued doing this and Mason just stared at her. He was so incredibly attracted to this girl. Her long hair pulled up with a few pieces framing her face. Her eyes, staring back at him. Her lips, half smiling while she bit her bottom lip to keep herself from moaning to loud. Her perfect tits as they moved with every bounce she took on his cock.

“You’re so gorgeous," he told her.

“Thank you,” she smiled.

“I can’t wait to fuck you for real,” he said. “Where we can be loud and naked and roll around, getting into every and any position you desire.”

She leaned in and lightly kissed his lips.

“Soon, baby,” she whispered against his lips.

Needing to cum into her, Mason gripped her waist, holding her and preventing her from grinding on him anymore. He held her stationary on his cock, then he started moving his hips, thrusting himself hard into her.

“Oh my God!” Leni cried out. She put her hands on the top of the seat on either side of Mason’s head and used it to brace herself.

Mason used every ounce of energy he had to fuck Leni has hard as he possibly could. Leni barely moved, feeling like she was paralyzed.

“Mason,” she breathed out, closing her eyes. “Please don’t stop,” she begged.

“Not a chance, baby,” he told her, continuing to thrust in and out of her perfectly tight pussy.

Holding her still, Mason fucked her as fast and hard as he could. Leni's arms started shaking as she got closer and closer to a climax.

“I’m going to cum,” she announced to him. The moment she did, Mason could feel her pussy clenching against his cock. The feeling sent him over the edge and he couldn’t stop himself from blowing his load into the condom he wore.

“FUCK!” he groaned, feeling his cock pulsing as it was drained of his semen.

Within seconds of his release, Leni also bowed her head down and moaned out as she orgasmed with her boyfriend.

Mason’s head fell back against the headrest of the car and the two of them breathed in and out together. With her head still down, Mason slowly started rubbing her back, comforting her as her body relaxed.

After several minutes of sitting there, Leni raised her head up, looking at Mason. “That was incredible,” she told him.

“It was,” he agreed. He put his hand on the back of her head, pulling her into him for a passionate kiss.

They kissed for a long minute, their tongues playing with each other. After a little bit, Mason slowly pulled away.

“You should probably get off of me,” he told her, his eyes indicating down to where they were still connected.

“You’re probably right,” she agreed.

Very slowly, Leni pulled herself off Mason’s semi-hard cock. She sat down next to Mason and fixed the cups of her bralette when Mason had moved them to expose her nipples. She corrected the fabric on her chest, then as Mason took the condom off himself and tied the end into a knot, she found her tank top and put it back on.

Near the parked SUV was a garbage can. Mason fixed his pants, pulling them back on, then opened the backdoor and climbed out, walking over to the garbage to throw out the used condom and empty wrapper. When he returned to the car, he saw Leni had also gotten out, and was slipping back into her jean jacket.

Approaching her, Mason shut the back door they had both come out of, then playfully pushed Leni against the side of the car. Knowing she was heading back to her own car to start her drive home, Mason smothered her mouth with his, needing to hold her and kiss her again before they separated.

They made out against Mason’s car for several minutes before Leni pulled away slightly. “I really should get going,” she said softly.

“I know,” Mason sighed, not wanting the night to end. He looked down at Leni, looking into her beautiful eyes. “You’ll message me as soon as you’re home so I know you are safe?”

She nodded. “Of course. You do the same too.”

Mason leaned down and kissed the top of her head. “I will, baby.”

Wrapping his arms around her, Mason and Leni held each other for a minute. After he leaned down and kissed her one more time, very softly she pulled out from him. He watched as Leni walked away from him, heading to her own car. She stared at him over the roof of her small car, smiling.

“Bye Mason,” she said softly so only he could hear.

He smiled. “Bye Leni.”

She climbed into her car, started it, and Mason watched as she backed out of the parking spot and drove out of the parking lot.

It wasn’t until Mason was cruising on the highway, heading back to university, that he noticed laying on the passenger seat were the panties Leni had been wearing that she had taken off right before they had fucked in the back seat.