My Roommate's Sister

Not only had Leni left the guest room bed before Mason had woken up Saturday morning, but she had left the house before the rest of the family was at the table for breakfast.

Mason tried to not be obvious when he asked where she was and luckily Josh didn’t even look up from his plate when Carrie told Mason she had woken up early to go to the outlet malls with a friend. Mason couldn’t help but be a little disappointed he wouldn’t get to see Leni much on his last full day in St. Petersburg, but he was hoping she’d sneak into his room one more time tonight and he could talk to her about them remaining in contact when he went back to school.

After breakfast was cleared away and everything cleaned up, everyone packed up into Brian’s 4-Runner and headed to a local shopping mall. Brian and Carrie were going to take the two younger kids to an indoor playground while Josh and Mason did a bit of their own shopping then they would all meet up for lunch.

Josh and Mason’s first stop before they went to any stores was a coffee shop. They placed their orders, and while they were waiting, Mason decided to ask Josh something that had been on his mind since the night before.

“Does Patrick have a thing for your sister?” Mason asked.

“Yes,” Josh answered matter-of-factly. He looked over at Mason. “Did you notice?”

“I just noticed him staring at her a lot last night and when we were in line for popcorn, Leni and I were having a conversation and I couldn’t help but notice Patrick glaring at us.”

Josh shook his head. “I’ve told him a hundred times to lay off her.”

“You don’t want them dating?” Mason asked.

“Absolutely not,” Josh replied.

Mason braced himself before asking his next question. “Is it because Patrick is your friend and that would be weird?”

Josh was still for a moment, thinking about his answer. Then he shook his head. “No,” he finally said.

Mason silently let out a sigh of relief.

“Yes, Patrick is my friend,” Josh said, “but Leni has been through a lot. Her last boyfriend was a piece of shit who hurt her really bad.”

“How so?”

“He ruined her self-confidence.”

Josh walked up to the counter to receive his coffee order that was now ready. As he walked back to Mason, he continued.

“They’d go out to a party and she’d get all dolled up, feel amazing in what she was dressed in, and he’d see her and say things like, ‘that’s what you’re wearing? You don’t think it would be better if you covered your stomach?’”

Mason couldn’t believe that. Leni was a thin girl with a gorgeous body.

“He’d say things like that, but then also make fun of her for how small her chest was,” Josh continued. “He gave her a push up bra for her birthday. She opened it in front of the family,” he said angrily. “I’ve never seen her so embarrassed.”

Leni’s actions and comments she made about herself now made so much more sense to Mason.

Mason’s order was called out. He stepped forward to get his drink and with their hot coffees in hand, they walked out of the shop.

“And you think Patrick would treat her the same?” Mason asked.

“Patrick thinks she’s hot, but he’s not looking for a relationship,” Josh explained. “He’s a player, like me. Leni wants a relationship, a commitment. Kind of like you,” he added.

Mason couldn’t help the smile growing on his face. He was lucky at that moment, Josh was looking forward and not at him.

“I bug Leni a lot, but she’s still my sister and I love her. She deserves so much better than Patrick.”

Mason couldn’t help but hope he could be good enough for Leni in Josh’s eyes.

When the knock came at his door that night, Mason wasn’t reading. He was too excited to see and talk to Leni. She came in looking just as excited as he was, hopping onto the bed with him. She instantly had her mouth on his and was kissing him. Mason kissed her back for a few moments, but he pulled away, wanting to talk to her.

“I have something I need to talk to you about,” Mason told Leni before they could get too far.

“Oh good,” she replied, pulling back slightly. “I do too. Actually, I have two things.”

“These last few nights have been incredible,” he told her, holding her hand. “And I know it won’t be the same when I’m three hours away, but, if you’re up for it. I would love to stay in contact with you and maybe try dating long distance.”

His heart soared when he saw the smile forming on Leni’s face.

Continuing, he said, “I could drive here a couple times a month, or we could meet half way,” he proposed to her. “I already looked for some restaurants or malls we could meet at.” He pulled out his phone and showed her the list of places halfway between the University of Florida and St. Petersburg he had made throughout the day.

“Wow,” she said, looking at the list. “This is really something.”

“Good something?” he asked her.

She nodded. “Very good something,” she replied. “I was actually hoping to have the same conversation with you, I just didn’t do any research yet.”

He smiled at her. “So, you want to try this?” he asked. “Seeing each other long distance?”

She nodded. “Yeah, I do.”

Mason leaned in and kissed her lips hard, thrilled with how this was going.

“And if everything continues going well,” he told her, “we won’t have to be long distance when you start university next year.”

“Hopefully by then,” she said, “we’ll have figured out a way to tell Josh you’re dating his step-sister.”

Telling his best friend that he was seeing Leni was the last thought in Mason’s mind right now. He just shrugged. “We’ll just cross that bridge when it comes up.”

Smiling, Leni leaned in and kissed him again.

After a minute, Mason pulled away slightly. “You said you had two things you wanted to talk about?”

“Oh,” Leni said. “Right.” Reaching behind herself, Leni grabbed something she had brought into the room and hidden behind her back. “I got something while out shopping today. If you don’t want to do this, I totally understand, I just thought,” bringing her hands in front of herself, “maybe?” she finished as she presented to Mason a box of condoms.

Mason looked down at the box in her hands. It was a blue box containing 12 condoms. ‘Ultra ribbed for her pleasure’ it read in big bold letters. Mason had a similar box in his nightside drawer back at school, though it hadn’t been touched in months.

Mason would be lying if he said he hadn’t thought about sex with Leni. He had actually thought about it a lot. Even before the first time she knocked on his bedroom door, he thought about being with her. He just never spoke of it or made any mention of it to Leni as he wanted her to be okay with it on her own, without any pressure from him.

Looking up, Mason saw that Leni was staring at him, waiting for a response.

“Are you sure?” he asked her.

Leni nodded. “Very very sure.”

Mason reached out and took the box from her hands, placing it on the night table, then he took Leni’s face in his hands and pulled her towards himself, kissing her.

As they kissed, Leni climbed on top of him, sitting on his lap. She wrapped her arms around his neck and they held onto each other as their lips touched and tongues played.

Taking her pyjama top in his hands, Mason slowly pulled it up. He broke their kiss for a moment to pull it off and over her head.

Leni pressed her bare chest into his and after another long time of holding and kissing one another, Mason turned his body and placed Leni down on her back, placing her head on the pillow then climbing on top of her.

They continued kissing and Mason slowly trailed his hand down her body, putting it inside her shorts. Leni’s legs were spread slightly and Mason was easily able to slide his hand under her panties. Lightly touching her, Mason grinned and chuckled to himself.

“You’re already so wet,” he commented.

Very gently, Mason slipped one finger inside her, causing Leni to gasp against his mouth. It felt so good having just his finger in her pussy. He couldn’t wait to have his entire cock in her.

Removing his finger from her, he took his hand out from under her shorts then sat up over her. He took the fabric of her pyjamas in his hands then slowly pulled them down and off her legs. Tossing both her shorts and panties off the bed, Mason looked down at her, amazed again by the sight of her naked body.

Climbing back over her, he leaned in to kiss her, but kept the lower half of his body raised up to take his boxers off. He pushed and wiggled them off his body as he continued kissing Leni’s lips, throwing them off the bed once he was free of them.

It was at this moment he realized this was the first time they were both completely naked together. He didn’t want to go too far without a condom on, but he did want to touch her at least once without any barriers.

“I won’t put it in,” he told Leni, “but can I touch you with my cock just once without a condom on?” he asked.

“Are you clean?” Leni asked him.

He nodded. “Yes.”

“Okay,” Leni agreed. Mason felt her legs spreading.

Very slowly, Mason lowered himself down, placing his erection against her wet lips.

“Oh my gosh,” Leni gasped the moment she felt his cock against her flesh.

Mason kept his promise and didn’t put himself inside her but even just rubbing himself against her was so incredibly hot. After only a few swipes of his rod on her pussy, he was reaching over the nightstand where the condoms were.

Sitting up, Mason tore into the box like an animal, pulling out several at once. Leni couldn’t help but giggle as she watched him try and rip a single one from the perforation. He tore it open, pulling the condom out then rolling it onto his cock. Once on, he tossed the remaining packets to the side, not wanting to throw them too far in case they needed more.

Laying back down on top of Leni, he kissed her hard and passionately. He never wanted her so bad as he did right now.

“I want you so bad, Leni,” he told her.

“Please,” she begged, between kisses. “I want you too.” He could feel her raising up her hips to him, as if begging him to be inside her.

Holding himself up so he didn’t have all his body weight on her, Mason looked down at Leni. She looked so beautiful underneath him. His hard cock was lined up to her entrance, but he didn’t go in just yet.

Before he pushed himself into her, he caught his breath and then looked into her eyes. “Before we start,” he said, “I need to know. Are you a virgin?”

Leni shook her head. “No.”

“Okay,” he replied. “I just wanted to make sure so I don’t hurt you or anything,” he explained. “Are you ready?”

She nodded. “Yes please.”

“If you want me to stop,” he told her, “just say the word and I’ll stop.”

“I won’t,” she told him. “But thank you for letting me know I have the choice.”

“Of course,” he smiled. Looking down between their legs, he watched as the tip of his cock went into her, but then looked back up at her face, wanting to see her expression as his length went all the way inside her.

“Oh my God,” Leni moaned instantly the moment his thick cock was inside her.

Mason was 8 inches long and about 3 inches thick. He wasn’t fully inside her yet, just letting her get used to him slowly. He believed her that she wasn’t a virgin, but her cunt was so tight, it was hard to imagine. Finally, after a few slow minutes, he was fully inside her.

“You feel so big,” Leni commented.

“Are you okay,” Mason asked her. “I’m not hurting you?”

“I’m great,” Leni responded.

“Tell me if I’m hurting you,” Mason instructed her as he slowly started moving his hips pulling himself down then pushing his cock back into her.

“Oh,” Leni moaned. “You feel so good,” as he moved his length inside her.

Leaning down, Mason pressed his lips to hers as he began to move faster. Leni wrapped her arms around his neck and pulled him as close to her body as she could.

“Fuck,” Mason groaned. “You are so tight.”

As Mason continued picking up the pace and thrusting faster in Leni, she once again had to cover her mouth to keep herself from moaning too loudly. Mason pressed his lips to her neck and whispered into her ear. “One weekend, we’re going to meet at a nice hotel,” he told her. “I’m going to kiss you, finger you, eat your pussy and fuck you all weekend, and you can be as loud as you want.” Leni groaned into her hand again at the thought. “Would you like that?” he asked her.

She nodded, then moved her hand to the side so she could answer out loud. “That sounds amazing.”

Mason knew he was close so he pushed himself slightly off Leni’s body, putting himself just above her. At this angle, he was able to fuck her even faster and harder.

“Oh God,” Leni cried as he started. “Yes, Mason, don’t stop.”

“Never, baby,” he groaned out.

He stared down at her perfect body as he continued fucking her. She was biting down on her bottom lip to try and keep herself from crying out too loud. Her small breasts bounced with every thrust. She was so beautiful.

He felt her pussy clenching against his cock and he knew she was also close to cumming.

“Mason,” she breathed out again.

“I know, baby,” he told her. “Me too.” He pushed himself into her as deep as he could, pulled back then slammed back in again. “Cum for me, beautiful. I want to feel you on my cock.”

“Yes, yes yes,” Leni moaned. Her head came up off the pillow for a moment, biting her lip as her orgasm went through her body. Staring at her and watching her climax, took Mason over the edge and he came hard, falling forward and moaning into Leni’s shoulder. He felt his cock pulsing and emptying into the condom. They stayed like that for a while, holding each other as they caught their breath.

Mason groaned loudly as he woke up Sunday morning. Between spending a relaxing long weekend away from school with his best friend, and everything that had happened with Leni, Mason was dreading getting up and heading back to campus.

Opening his eyes, Mason’s face dropped when he saw that once again Leni had left the bed, but hearing footsteps, he looked up and saw, though she was up, she hadn’t gone back up to her own room yet. She was still topless, but pulling her pyjama shorts up her legs.

“Good morning,” Mason said, smiling at her.

Leni looked towards him. “Good morning.” She picked her tank top off of the ground then stood up straight. “I hate having to sneak away like this,” she told him, “but my parents will kill me if they find out I’ve been staying down here every night.”

“It’s okay,” Mason said, climbing out of the bed. “I understand.”

Leni pulled her pyjama top back over her head and when she was fully dressed again, Mason reached out and held onto her. “Could I say one thing before you go because I know we won’t have another chance to be alone before I leave.”

“Of course,” Leni said, looking up into his eyes.

“This weekend was absolutely incredible,” he started. “You are such an amazing woman and even though I am going to miss you so much, I am so happy to be dating you.”

Leni smiled as he spoke.

“I am so excited for whatever this may become between us and I just hope, even if we are apart, I can show you how wonderful you are and be everything you deserve.”

Leni giggled quietly. “Where is this all coming from?” she asked him.

Mason shrugged then pulled her into a big hug. “Just something I wanted you to know before I have to leave.”

Leni lifted her head, resting her chin on Mason’s chest as she looked up at him. Looking down at her, Mason smiled, then leaned down and kissed her.