My Roommate's Sister

“Mason? Is that you?”

It was a warm Saturday in April and Mason was walking across campus heading back to his dorm. He just finished a morning shift at the car shop he worked at when he heard his name being called. Looking towards the voice, he smiled when he saw his friend’s parents, Brian and Carrie approaching him. He smiled even bigger when he saw who was also with them.

“Dr and Mrs Hart,” Mason said, walking towards them. “It’s great to see you.”

“Please,” Brian said, holding open his arms and pulling Mason in for a hug. “It’s Brian and Carrie.”

“Sorry,” Mason said, finishing his hug with Brian and immediately going to Carrie’s arms for another. “It’s great to see you.”

After a comfortable embrace with Carrie, Mason pulled away and looked down at the young woman next to her. “Hi Leni.”

“Hi Mason,” Leni replied, smiling up at him. Mason held out his arms for her and the two of them hugged. Though Mason knew Carrie was aware of their relationship, Brian still wasn’t, so even though Mason held Leni a little longer than he had Brian or Carrie, they still pulled back from each other before it became too obvious.

“What brings you all to campus?” Mason asked the group.

“Visiting Josh, of course,” Brian answered. “But we’re mainly here for Leni to see the school since she’ll be starting here in September.”

Mason’s eyes shot to Leni who was smiling brightly up at him. “You got accepted?” he asked her.

“Just found out a week ago,” she told him, grinning ear to ear.

It took all of Mason’s control not to pick his girlfriend up and twirl her around in joy.

“Congratulations,” Mason told her. “Welcome to the University of Florida, fellow Gator.”

Leni giggled. Clearly it was killing her as well that she couldn’t celebrate with Mason the way they wanted too.

“We just did a campus tour,” Carrie explained to Mason. “Got to see all the classrooms and labs she’ll be studying in.”

“That’s awesome,” Mason said. “Are you staying long or are you heading back to St. Pete’s soon?”

“We’re actually leaving tomorrow morning,” Brian said. “We have a few more meetings with the school, so we figured we’d make a day of it. We are staying in a hotel just off campus,” he explained.

“Nice,” Mason commented.

“We have reservations for dinner tonight at Apple Grace’s,” Carrie told him. “I know Josh will be coming. We’d love for you to join too.”

There were many shops and restaurants just off campus. Most of them were dives, catering to the broke students. But Apple Grace’s was one of the more high end places near the school. Mason had only been there a handful of times.

“I’d love to,” Mason smiled, happily accepting the invitation. “Thanks for inviting me.”

“Happy to have you,” Brian smiled at him.

“You’re basically family,” Carrie added. Mason glanced at her and the two of them shared a look. It felt like she wanted to say more to Mason in regards to his relationship with her daughter, but with Brian standing right beside her, nothing more was said.

Checking his watch, Brian spoke to his wife. “Our next meeting is in twenty minutes, dear. We should probably get going.”

“Do I need to come to any of these?” Leni asked her parents. “Could I go with Mason to find and hang out with Josh?”

“I think that should be fine,” Brian answered, him and Carrie looking at one another. “Everything else we should be able to handle. We can all just meet up later at the restaurant if you want to spend the rest of the day with Josh.”

“Okay great,” Leni said, smiling.

“Our reservations are for seven,” Carrie reminded the two of them. “We’ll see you there.”

“Bye Dr and Mrs - sorry,” Mason said, correcting himself. “Bye Brian and Carrie. We’ll see you later tonight.”

Leni waved to her parents as she stepped up beside Mason and the two of them started walking away, heading to Mason and Josh’s dorm.

After a full minute of walking, Mason glanced behind himself, making sure Brian was out of earshot. When he was completely out of sight, he reached over, wrapping her in his arms and hoisting her up triumphantly.

“You got into the school!” he cheered.

Leni giggled as Mason spun her around. “I was going to tell you right away when I found out,” she explained, “but my parents decided to make the trip down here so I thought it would be fun to surprise you.”

Placing her down on the ground, Mason took Leni’s face in his hands and kissed her hard on the mouth. Leni smiled against his mouth. She knew he’d be happy she was accepted into the same school he was at so they could be together starting in September, but she wasn’t expecting all this.

“Best surprise ever,” Mason said after they pulled out of the kiss.

He held her face for a moment longer, staring into her eyes. His mind was going a million miles a minute thinking about what things would be like starting in September when she was on campus with him. Before, any time he thought about it, it was only hypothetical, but now that she was officially accepted, he could start picturing and planning things that were really going to happen.

It was at that moment, Mason realized he didn’t know when Josh would be done with baseball practice and if he was finished, Mason had no idea where on campus he was.

“Come with me,” Mason told Leni, taking her hand and leading her away. Mason knew once they met up with Josh, he wouldn’t be able to hold Leni’s hand or kiss her anymore, so he wanted to at least get a bit of alone time with her before then.

He led Leni to his dorm building but they didn’t go through the main entrance or up to his room. Instead he took her through the side door where the building's emergency stairwell was. Students rarely used this staircase. There was an elevator and another stairwell when you entered the building through the main doors. This one was closed off, had no windows and really was only used in emergencies.

Mason personally had only ever used this staircase once or twice when the elevators in the building were under repair, but Josh had mentioned it to him a bunch of times, telling him it was a great place to go and be alone.

“This is a spooky hallway,” Leni commented when the door closed behind them and they were totally alone.

“Yeah,” Mason agreed. “Sorry, I just don’t know when Josh is done practice and when he’ll be back in the room and I wanted to spend a little more time with you alone before we see him.”

Without another word, Mason pushed Leni back until she was pressed up against the wall. He dropped the backpack he was wearing to the floor then put his hands on either side of the head, pinning her there. Lowering his head to hers, he kissed her hard. Leni’s arms wrapped around his neck, pulling him down to her. Mason felt her tongue on his lips and he opened his lips up slightly, allowing her tongue into his mouth.

Through his jeans, Mason felt himself getting rock hard. As he kissed Leni, he pressed himself into her, letting her feel his erection and how hard she made him.

Slowly, Leni unwrapped her arms from Mason’s neck and slowly glided them down his body, moving them slowly down his shoulders, chest and stomach, stopping at his erection poking into her. As they continued kissing, Leni lifted Mason’s shirt slightly, just enough to give her access to the button of his fly. She undid the button then pulled down the zip. Mason grabbed the sides of his pants and pushed them down just slightly, freeing his cock of the denim.

After pushing down his own pants, Mason gripped the fabric of the maxi-skirt Leni was wearing and began pulling it up, touching her smooth skin as he raised it up. Getting to the top of her thighs, Mason found her panties.

“Can I take these off?” he breathed against her lips.

“Yes, please,” Leni moaned back.

Mason was only able to pull the panties half way down her legs without stepping completely away from her. He pulled them just above her knees, then brought his hands back up to between her legs. With one hand, he gathered the fabric of her skirt and held it up, the other hand, he brought between her legs and found her sex. Leni spread her legs as much as she could, giving Mason better access to her pussy and clit.

“Fuck,” Mason groaned as he touched her. “You are already so wet.” After only a few strokes of her pussy, he was able to slide two fingers into her easily.

“Oh God,” Leni said, craning her head back as she moaned.

Mason leaned into her, placing his lips against her neck. He sucked her neck as he continued moving his fingers in and out of her. “I love how tight you are,” he told her.

Using his thumb, he pressed down and circled her clit, all while still fucking her with his two long fingers. He twisted them and curled them inside her, making Leni moan and gasp.

Bringing his mouth to her ear, he breathed deeply in her ear. “Tell me what you want, baby.”

“Please,” she begged. “Make me cum.”

“I’m going to make you cum all over my hand,” he told her. “Then I’m going to pull out my cock, fuck you and make you cum again.”

“Yes,” she moaned.

Mason continued finger fucking her, kissing up and down her face and neck as he did. Leni moaned deeply as he brought her closer to orgasm.

Mason felt her pussy tighten around his fingers as Leni began to climax. As her body clenched up and she moaned loudly, Mason bit down lightly on her neck.

As she breathed in and out, coming down from the orgasm he had given her, Mason kept his fingers inside her, just moving them a lot slower. He very carefully pulled them out of her, but kept his hand on her sex.

“That felt so good,” Leni told him after taking a minute to calm down.

Mason leaned into her and kissed her lips hard and passionately. “You are so hot when you cum,” he told her. “Can I make you cum again?”

“Yes please,” she breathed out.

Letting go of her, Mason bent down and reached for his backpack. Last month, Mason and Leni spent the whole weekend together at a hotel in San Antonio. He had packed an entire box of condoms and he knew, even though he had unpacked since returning from the trip, that there were still some in his backpack. Digging into a pocket inside the bag, Mason found two condoms still in their wrap. Leaving one in the bag, he opened the second one, tossing the foil package in his open backpack then rolling the latex onto his erection.

While he had been looking for it, Leni had completely removed her panties, leaving them on the floor. She held her skirt up, keeping herself covered, but indicating to Mason that she was ready for him.

Grabbing her thighs, Mason hoisted Leni up and sat her on the edge of the handrail. On the bottom floor of the staircase, the handrails were attached to a large concrete ledge which made the perfect seat for Mason to place Leni on. Then when he stood on the second stair, he was at the perfect height that placed him right at Leni’s pussy.

As he stepped up, getting close to her, Leni spread her legs wide for him. Mason held onto his cock as he lined it up to Leni’s entrance. He pressed his tip against her, but didn’t push in just yet.

“Ready?” he asked her.

Leni nodded.

Mason held her hip with one hand then held onto the handrail with the other to keep himself up. Once he felt secure and that he wasn’t going to fall, he pushed his entire length into Leni’s cunt.

“Oh my God,” Leni cried, feeling him inside her.

“Fuck!” Mason groaned at the same time as Leni.

She was already so wet from him finger fucking her so he glided in and out of her tight pussy easily which helped since they weren’t at the greatest angle or position. Either way, Mason continued to fuck her lustfully.

“You should touch yourself,” Mason told Leni.

Without missing a beat, Leni put her hand between her legs and started rubbing herself. Looking down, Mason watched a combination of his cock going in and out of her sweet sex and her fingers stroking her clit. It was so fucking hot.

“Oh yeah,” he moaned, watching her fingers work her own clit. “Just like that.”

Leni moaned quietly, leaning back as much as she could on the ledge. So many different feelings of intensity went through her body as both Mason and her own hand pleasured herself.

“How does it feel?” he asked her.

“So good,” she moaned, continuing to touch herself.

“You are so fucking sexy,” Mason told her as he stared at her. He loved watching her while he fucked or pleasured her. She was so gorgeous and the moans that came out of her were almost enough to make him cum when he listened to them.

Mason raised up her leg he was holding as much as he could, giving him a better angle to go even deeper into her.

“Oh yes!” Leni cried when she felt his thick cock further inside her. “You feel so big,” she told him.

“You feel so tight,” he responded.

“I’m close,” she breathed out. “Please,” she begged. “Fuck me harder.I’m going to cum.”

Gripping onto her leg and the handrail, Mason fucked her as hard as hard as he could, going as deep into her cunt as possible.

“YES!” Leni cried, craning her head back, but still touching herself. “Ohhh, it feels so good.”

Mason bit his bottom lip, watching her climb higher and higher to her peak. He felt her pussy clenching and tightening on his cock so he knew she was nearly there. Knowing he was also close, he thrusted in and out of her tight pussy, giving it everything he had.

As Leni moaned loudly with each thrust, Mason said, “yes baby. You’re almost there, I can feel it. Cum all over my rock hard cock.”

“Are you going to cum too?” Leni asked him.

“Oh yeah,” he answered. “I’m going to cum so fucking hard inside you.”

Leni bit her lip then rubbed herself hard, finally bringing herself to the top of her climax and moaning deeply as she came. At the same time, Mason cock clenched up and he came as well, ejaculating a massive load into the condom.

“FUCK!” he cried as he emptied himself. Leni leaned back, breathing in and out.

Finally after a long moment, they looked at each other.

“Was that okay?” Mason asked her.

“Of course,” Leni responded. “It was incredible.”

Mason delicately put Leni’s leg down, then reached for her upper half, pulling her into a kiss. Leni took Mason’s face in her hands and held him as they kissed passionately.

Slowly, while still kissing her, Mason gently took her down from the ledge, placing her back on her feet on the floor.

After kissing for several minutes, Mason and Leni pulled away from each other. Bending down, Mason picked up and handed Leni her panties back.

“I’ll take you upstairs,” he told her. “You can clean up in the bathrooms and then we’ll wait for Josh in our room.”

“Okay,” Leni said, stepping into her panties and pulling them up her legs. Once they were on, she fixed her skirt, dropping the fabric down so it sat on her legs properly.

Mason took the soiled condom off himself, knotting it at the top, then used a random piece of paper he found in his backpack to conceal it. He folded the paper around it, hiding it completely, then put the folded paper in the front pocket of his back pack, intending to throw the whole thing out in the bathrooms upstairs along with the empty foil it had come in.

After zipping up his backpack, Mason stood back up. He pulled his pants back up, doing up the button and the fly, then put his backpack on his back. Holding out his hand, Leni took it and the two of them started climbing the stairs, heading up to the third floor where Mason and Josh’s dorm room was.

Mason knew when Leni started school in the fall, even when Josh was aware of their relationship and they didn’t have to sneak around anymore, he knew the two of them would still make visits to this stairwell again. There was no way they weren’t doing that again.