My Roommate's Sister

The first time Mason had met his best friend Josh’s younger sister was when Josh invited him to come to his families for Thanksgiving. The two made the two and a half hour drive from the University of Florida campus to St. Petersburg where Josh had grown up. At his friend's large family home, Mason was introduced to Josh’s dad, Brian, step-mom, Carrie, younger half siblings Peter and Sarah and then Josh’s step-sister, Leni.

Leni was 18 years old, in her last year of high school. She had long red brown hair and beautiful green eyes. She was short, thin and had a small chest. Mason couldn’t help but look at her breasts, loving small tits himself, and he wondered if she was even wearing a bra under her t-shirt as he could see her nipples peebling the fabric.

The boys had arrived the Wednesday before Thanksgiving with the intention of staying with Josh’s family until Sunday afternoon. Carrie showed Mason to the guest room she had prepared for him. It was a good sized room on the main floor of the house, separated from the families upstairs bedrooms. It had a queen sized bed, a dresser, TV mounted to the wall, and a bookshelf filled with different coffee table type books and paperbacks. It even had an attached bathroom for Mason to use that had a toilet, sink and shower stall. Mason unpacked the clothes he had brought in his duffel bag, then joined the family out back where they had gathered for dinner on the patio. Everyone but Carrie had already taken their seat around the outdoor table and the only spot left besides the one next to Josh’s dad (which Mason assumed would be where Carrie was going to sit) was one between Josh and Leni. Mason pulled out the chair and took his seat between the two siblings.

While they ate, Peter was asking Josh and Mason tons of questions about university and their classes. Mason happily answered each of them, enjoying the curiosity the young kid was showing.

Peter had asked them a question about working on campus, which Josh was answering for him since Mason had a job off campus, when Mason felt someone’s foot touch his under the table. Taking a quick glance, Mason saw Leni’s small foot touching his. He looked at her for just a moment and saw that she was also looking at him. As soon as they made eye contact, Leni wrapped her leg around his. Mason didn’t pull his leg away. He was flattered Leni was touching him. Did she find him attractive? He definitely found her gorgeous.

“You know,” Carrie said to the table after Josh finished answering another one of Peter’s questions. “Leni applied for the University of Florida.”

Mason turned to face Leni. “That’s really cool,” he said, genuinely. “What are you thinking of taking?”

“Biology and natural sciences,” Leni answered.

Mason had to admit to himself, he was shocked when he heard this. He did not think from looking at Leni that she was a science nerd. She looked nothing like the stereotypical lab rat. Though he’d like to see her in a lab coat bending over a desk.

“Yeah,” Josh said, shoveling salad into his mouth. “She’s a science dork.”

Leni’s eyes shot towards Josh, glaring at him. “Shut up, Josh.” She had also pulled her leg away from Mason’s after the interaction with Josh which made Mason frown slightly.

Mason wasn’t surprised Josh was making fun of Leni. He was at U of F on an athletic scholarship for baseball and was currently taking media production classes. Mason was studying to become a pharmacist and also received lots of teasing from Josh when he had to study and couldn’t come out partying with the rest of the baseball team.

“Josh,” Brian said, sternly. “Don’t be rude to your sister.”

The dinner conversation shifted to baseball and when Brian and Josh were in the middle of a heated discussion about pitching speed, Mason leaned over and whispered in Leni’s ear, “I think bio and science is really cool, too.”

Without looking up from her dinner plate, Leni blushed and Mason felt her leg against his again.

After dinner was cleared, the family moved to the living room where everyone stayed up talking until late into the evening. It wasn’t until after 11 that Carrie announced they should get to bed. Sarah, being only six, had gone to bed hours ago, but Peter wanted to stay up with Josh and Mason and was the first to whine when Carrie told him it was time to go to bed. But he went when Josh said he’d carry him up to his room and both Josh and Mason promised to play with him in the pool the day after Thanksgiving.

As everyone headed upstairs, Mason stood at the bottom, saying good night. Carrie double checked if there was anything he needed before she went to her room and when he assured her there wasn’t, she also went up.

The only one left downstairs was Leni, clearly moving a lot slower than the rest of the group as she filled a glass of water to bring to bed.

She stood at the bottom of the stairs, looking at Mason, and he looked at her.

“Thanks for what you said at dinner,” Leni said to him when they were alone.

Mason smiled. “No problem.”

She tucked a strand of hair behind her ear. “A lot of the time I feel alone in this house. All Brian, Josh and Peter want to talk about, it seems, is baseball. My mom had to force them to come when I presented in the science fair.”

“I’m really sorry about that,” Mason said. “If it makes you feel any better, I have four older brothers. All athletes. Part of the reason I didn’t go home for Thanksgiving is because my father acts like me being a pharmacist is a disappointment.”

Leni narrowed her eyes. “Wow,” she said. “That’s really upsetting. I’m sorry too.”

Mason shrugged. “It’s fine. Like I said, it’s why I don’t go home for holidays.”

“Well,” Leni said, looking down at her feet. “You are always welcome here. The boys can be annoying, but my mom makes sure everyone is treated with love here.”

“I’m really enjoying my time here so far,” Mason said, smiling.

Leni looked up at him and smiled. Being almost a foot taller than her, Mason looked down at her, smiling back.

“Well,” Leni said after a while, “Good night.”

“Good night, Leni.”

Mason watched as she turned and walked up the stairs, looking back towards him twice as she went. Once she was up and the hallway light was turned out, Mason turned, going into the guest room.

In the privacy of the guest room, Mason changed out of his clothes into a pair of pajama pants. He washed his face and brushed his teeth then climbed into the soft bed with the book he was currently reading. The queen sized bed was bigger than the single he had in his dorm, the mattress was much better and the sheets were softer. He was so excited for the next four days of sleep he would get in this bed before going back to school.

He had been reading his sci-fi novel for about 30 minutes when he heard the tiniest knock on his door.

“Yes?” he responded, putting the book down.

He was genuinely surprised when the door opened and he saw Leni’s face. He fully believed it was going to be Josh offering to share a joint on the back deck. But seeing Leni, he sat up in the bed, and closed his book, putting it down on the night side table.

“Leni,” he said. “What are you doing?”

“Can I come in?” she asked him.

“Yes, of course,” he responded.

Slipping into the room, Leni closed the door behind her quietly. She stood on the other side of the room, looking towards Mason. Her long hair had been pulled up into a messy bun with pieces still hanging around her face and she had changed out of her clothes into her pajamas. She was now wearing a plain white cotton top and dark green booty shorts. If her nipples hadn’t been clear earlier throughout the day, they were now. Not only could Mason see them poking into the fabric as they had been all day, but now, in the thin white shirt, he could almost see the outline of her areolas as well. He shifted his legs, attempting to hide the erection that was now forming under the sheets.

“Sorry,” she said, walking closer towards the bed. “I couldn’t sleep.”

“That’s okay,” Mason replied. “I wasn’t planning to go to bed for a little bit, so you are welcome to hang out here if you want.”

Leni approached the side of the bed and pointed towards it. “May I?” she asked.

Mason gestured to the edge. “Of course.”

As Leni climbed onto the end of the bed, Mason couldn’t help but look down her low-cut shirt. He couldn’t see her nipples, but he was able to make out the round shape of her tits. He instantly regretted looking though as his cock got even harder. He put one hand under the sheets attempting to push it down so Leni didn’t see.

“It must be nice,” she said, “getting a room to yourself for a few days.”

“You have no idea,” Mason said, a little laughter in his voice. “Not only is this way more comfortable than the beds in the dorms, but I won’t have to listen to Josh all night long.”

“Oh my gosh, he’s awful,” Leni agreed. “We’ve had to share rooms a few times when we’ve gone on vacation and I always have to pack earplugs or else I won’t sleep at all.”

Mason pinched his eyebrows together in confusion “He brings girls back to his room when you are on vacation and sharing a hotel room?”

“What?” Leni exclaimed. “Gross, no! I mean his snoring is awful.”

“Oh my gosh,” Mason said, embarrassed. “Yeah, his snoring is really bad.”

Leni pulled her legs up onto the bed, criss-crossing them. “Josh brings girls back to your dorm room while you are there?” she asked. “What do they do?”

Mason made a face at her, saying, ‘I think you know what they do,’ and Leni cringed.

“Disgusting,” she exclaimed. “He does that while you are there and trying to sleep?”

Mason shrugged. “I think it’s a pretty normal thing in university. It’s either in the guys' dorm or the girls. Not really a lot of private places.”

“Yuk,” Leni said. “How often does he do that?”

“Well he had a steady relationship with a girl for a couple months, so it was almost every night when he was with her. But they broke up and since then it's been probably a few times a month.”

“Could I ask you a personal question?” Leni asked.

“Go for it.”

“Do you ever bring girls to your room?”

Mason looked into Leni’s eyes. She was staring back at him with her gorgeous green eyes.

“A few times,” he answered honestly. “I had a serious girlfriend for most of first year, but I don’t really go out to parties or anything like Josh does, so I don’t meet a lot of women. I’ve had maybe two hook-ups since MacKenzie and I broke up, but that’s it.”

Leni nodded her head as she listened to him. “So you don’t have a girlfriend right now?” she asked him, pushing a strand of loose hair behind her ear.

“No,” Mason answered. “Totally single.”

Looking down, Leni asked “Would it make things weird and awkward if I told you I was relieved to hear that?”

Mason grinned at her. “Why are you relieved?” he asked, though he assumed he knew the answer.

Leni looked up at him, shyly. “Because I think you’re really hot and I’d be a little jealous.”

“Well,” Mason said, leaning towards Leni and touching her bare leg, the closest thing to him. “You have nothing to be jealous of and I also think you’re beautiful.”

Leni lifted her head and looked at Mason, fully in the eyes. They stared at each other for a few moments before Mason held out his hand to her. She took his hand and he gently pulled her towards himself. She crawled on the bed, climbing over his legs and settling on his lap. Once she was comfortably straddling him, Mason reached his hand up and touched her face. They continued looking into the others eyes as Mason pushed her loose hair out of her face. He moved his hand behind her head and very slowly pulled her towards his face. Once they were close enough, he leaned into her and kissed her.

As they kissed, Leni wrapped her arms around Mason’s neck, pulling his whole body into hers. Mason held the back of her head with one hand, the other slipped under her shirt and he ran his fingers up and down her back. He could feel goosebumps forming on her skin as they continued to kiss. When Mason opened his lips slightly, Leni pushed her tongue into his mouth, finding his tongue.

As their kiss deepened, Leni ground herself against him and it wasn’t until he felt her connecting to his erection that he realized he wasn’t hiding it from her anymore. Though the bedsheets were still between them, his raging hard-on was poking right up, directly where Leni was on his lap.

“I can feel your cock,” Leni told Mason, pushing herself into it. “I saw you trying to hide it when I first came in here.”

“Sorry,” Mason said, though he didn’t mean it. “You just looked so sexy in your pajamas.”

They continued kissing and Mason found himself moving his hands forward on Leni’s body. She didn’t protest as he moved them up her ribcage and rested on her breasts. She didn’t stop him, in fact, she moaned into his mouth when his thumbs found her hard nipples and started circling them.

“Can I take your shirt off?” Mason asked her. Leni sat up straight and lifted her arms up. Grabbing the fabric of the shirt, Mason pulled her shirt up, pulling it off her arms and head, then dropping it to the floor beside the bed.

Leni’s breasts were small, probably only 34A but Mason had always loved smaller tits.

He stared at them as he cupped his hands around them. His hands were so large and Leni was so small, they covered her whole breast.

“They are so small,” Leni commented, clearly self-conscious of them.

Mason looked back up at her face, his hands remaining on her body.

“Don’t say that like something is wrong with them,” he told her. “They are so sexy. You are so sexy.”

“You really don’t mind how tiny they are?” she asked.

“Not at all,” he said. “I could look at them and play with them all day if you let me.”

Leni smiled. “I’ve had boyfriends in the past tell me they wished they were bigger and girls at school call me ‘training bra.’ It’s embarrassing.”

“If anyone should be embarrassed, it should be them,” Mason told her. “You are gorgeous.” Keeping his eyes locked on hers, Mason moved his hands off her boobs and down to her hips. “Besides,” he started, lifting her off him and tossing her onto her back beside him, “any guy should be happy when he gets to see tits in general,” he told her as he climbed on top of her. “And it should be considered a God damn privilege to see ones this beautiful.”

Leni stared at Mason as his body went on top of hers. He pulled the blanket away so there was nothing between them anymore and then he lowered himself onto her. He was still wearing his pajama pants and she was still in the shorts she wore to bed, but now, without the blanket, she could really feel his erection against her body.

Her arms were resting above her head and Mason took both her wrists in one hand, holding them there. Using his free hand, Mason traced a line from Leni’s lips down her neck, collarbone, running up the small mound of her right breast to her hard nipple. Mason circled her nipple with his pointer finger five times then lowered his head, putting the bud into his mouth.

“Oh my gosh,” Leni said, closing her eyes.

“Is this okay?” Mason asked her between sucks. “I can stop if it’s not.”

“No,” she breathed out. “Don’t stop.”

Mason alternated between sucking her nipple and circling it with the tip of his tongue. As he did this, his hand went to the other side of her body and pinched her nipple on her neglected breast.

“Oh my goodness,” Leni moaned. “That feels so good.”

Mason could see her rubbing her inner thighs together and he wondered if she was getting wet. He wanted to reach into her shorts so badly to touch her and find out for himself, but he held off and continued giving his full attention to her tits.

He flicked her nipple with his tongue, pulled it into his mouth to suck on it, and a couple times, he bit his teeth down on it. Each different thing caused a new noise from Leni’s mouth, either a moan or a yip.

He had been worshipping her breasts for a few minutes when Leni moaned out, “Mason, could you please touch me.”

Mason lifted his head to look at her face. “Touch you?” he asked.

“Down there,” she clarified.

Letting go of her, Mason sat up in the bed and brought his hands to the waistband of her shorts. Despite how badly he wanted to see her and touch her, he took his sweet time slowly pulling them down her legs. The pace he was pulling them was so agonizingly slow, Leni struggled not to push his hands away and rip them off herself.

Finally they were off and Mason stared down at the pretty pink thong she had on under the shorts. He couldn’t help but grin when he saw the wet spot on her crotch.

Fuck, he thought to himself as he stared at it. He wouldn’t mind tasting that.

He looked back up to Leni’s face. “Can I take these off?” he asked her.

Leni nodded silently and Mason wasted no time. He took the fabric of the panties between his fingers and slowly pulled them down her thin legs. When he got to her feet, she lifted her legs slightly off the bed, allowing him to remove the garment completely from her body. He tossed them off the floor with the rest of her clothes then looked back at her, his eyes roaming up and down over her whole body.

Leni laid out on the bed, her arms still up above her head and her naked body completely on display for him. At the peak of her small round breasts were her pink nipples, still hard from being thoroughly sucked and pinched. Just below her thin stomach and pierced belly button was the most gorgeous pussy Mason had ever seen. Perfect pale lips with just the tiniest bit of brown hair. It took all his will power to not rip off his pants and ravish her whole body in every way possible.

“You are so beautiful,” he told her. The smallest smile grew on her face at his words.

Keeping his pants on, Mason laid beside Leni, wrapping his arms around her and pulling her naked body into his clothed one. Leaning in, he kissed her lips softly. He pressed his erection against her body, making her moan into his mouth.

Mason slowly dragged his hand down her body, going from her shoulder to her hip, stopping on her inner thigh.

“It’s okay if I touch you?” he asked her, wanting her full consent.

She nodded. “Please,” she begged. “I’m so wet.”

Mason’s fingers went between her legs and she opened up for him, allowing his hand and fingers access to her sex.

He stroked between her lips, making her quietly gasp. While he touched her, he stared at her face, loving the way she bit her lip and moaned with every movement.

Spreading her lips, his thumb found her clit and he lightly swiped his finger over it.

“Oh God,” Leni cried, her hands fisting into the sheets. As Mason circled his thumb over her clit, Leni had to press her lips together fighting back her moans. The house was well insulated but she was still nervous about someone upstairs hearing her.

After a minute of teasing, Mason took one of his fingers and pushed it inside Leni’s wet pussy. His finger slid into her wet entrance so easily and the sound of his finger going in and out of her on top of her muffled moans was getting him so hot. It wasn’t long before he inserted a second finger into her.

“Oh my-” Leni cut herself off, covering her mouth with one of her hands, her other one still fisted into the sheets. She moaned into her hand as Mason thrusted his fingers in and out of her, his thumb still pressed to her clit.

When he curled his fingers inside her, Leni’s back arched up and she moaned a long guttural moan into her palm.

“You’re so wet,” he whispered into her ear. “It’s so sexy.”

He continued fucking her pussy with his fingers and he could feel her starting to tense up.

“Are you going to cum?”

She nodded, her eyes still closed and hand over her mouth.

“Cum on my hand, baby,” he breathed into her ear. “I want to feel it and then taste your climax.”

He pushed his fingers in and out of her, twisted them and curled them while they were inside, finding her G-spot. Feeling her starting to tighten around him, he pressed his thumb hard onto her clit and even with her hand covering her mouth, her moans as she came were loud.

He didn’t pull his fingers out of her, but he softened and slowed down his movements. Leni breathed in and out enjoying her orgasm and slowly her back flattened back on the bed. She took her hand away from her mouth and opened her eyes, immediately seeing Mason smiling at her.

“That was amazing,” she told him.

Leaning in, Mason kissed her lips softly for a long moment. Then, staring into her gorgeous eyes, he slowly pulled his fingers out of her. Looking down at them, he saw how soaked they were with her wetness. Without any hesitation, he opened his mouth and stuck them in, tasting the sweetness of Leni’s arousal.

He moaned as he sucked every drop off his fingers. “Fuck,” he said, pulling them out of his mouth. “You taste so good.”

Leni blushed, then rolled into him, kissing him some more. Mason wrapped his hand around the back of her, holding him to her. They kissed like that for a long while. Mason found the blanket and covered their bodies with it.

Pulling out of the kiss, Mason pulled Leni’s small body into his.

“Go to sleep, beautiful,” he told her. “It’s so late.”

“But,” she said, yawning, “what about you?”

He smiled, kissing the top of her head. “Tonight was for you. We can worry about me later.”

“Okay,” she said, snuggling closer to him. “Good night, Mason.”

Reaching around, Mason turned off the lamp on the night side table, then immediately wrapped his arm around Leni again. “Good night, Leni.”