My Roommate's Sister

Mason and Josh ended up chatting the entire three hour drive back to campus so it wasn’t until they were back in their dorm that Mason texted Leni for the first time. He let her know they had made it back to school safely and that he missed her already. He couldn’t help but smile at the screen when she responded saying she missed him too.

Weeks went on. Mason went about going to his classes and his part-time job at a local car shop. To his friends, it looked like nothing was different in his life. It didn’t seem like they noticed how much more he was on his phone sending texts or how he was much happier than normal. Being long-distance was hard, but Leni made it worth it. Especially when she sent him a spicy photo of herself.

Josh invited Mason to join him back in St. Petersburg for Christmas and as much as he wanted to go, he had already bought a plane ticket to fly back home to Portland. He got the ticket before him and Leni started dating and he was regretting it now, wishing he could spend the holidays with his girlfriend.

Mason knew that Josh and his family went on a ski trip every Christmas to Vail Colorado, but it wasn’t until he was in Portland that he found out Leni hadn’t gone on the trip this year, choosing to stay home to study for exams. Because of that, they were able to Facetime each other every night and she could talk without having to whisper since she was home alone. Mason’s bedroom at his parent’s house was in the basement and normally he shared the room with his older brother, Aaron. But Aaron was spending the holidays with his girlfriend in Westbrook, so he had the room to himself.

“I do miss seeing the snow,” Leni told Mason one night as they video chatted. “It’s pretty much the only time in the year I see it.”

“I can send you some photos if you like,” Mason offered. “We got a ton of snow here the last couple days. I know it’s not the same as skiing down a mountain, but it’s something at least.”

“Yes please,” Leni begged. “Send me so many pictures of the snow.”

Mason smiled at the screen, loving Leni’s excitement.

“If I had come to Christmas,” Mason asked, “would you have gone skiing?”

“Yes,” Leni answered, right away. “I probably would have just stayed in the lodge to study while everyone went out on the hill.”

“How would we sneak away though?”

Leni pursed her lips in thought. “Well you and Josh would probably share a room and we both know he is a man-slut. So, he’d probably be off with some girl he met on the hill.”

“You forget,” Mason said, “he brings girls back to our dorm all the time. So he would probably still bring girls back to our room.”

Leni gagged. “We usually get a big villa though,” she told him. “I don’t think he’d bring girls back with our parents, Peter and Sarah all there.”

“So, if your whole family is essentially in the same apartment together, how would we sneak away?” Mason questioned.

Leni threw her head back and groaned. “Enough of the logic,” she argued. Mason couldn’t help but smile as her frustration was so adorable. “Is it too much to ask to have sex with my hot secret boyfriend in a hot tub while it’s snowing all around us?”

“Don’t worry, baby,” Mason told her. “I’ll make sure that happens one day.”

Leni smiled on the screen at him.

Although they texted almost all the time and talked on the phone a couple times a week, they weren’t able to meet up since Thanksgiving. Once school started again, they would both have exams, so they wouldn’t be able to see each other until February.

“I miss you,” she said, softly.

“I miss you too.”

Mason stared at Leni through the screen for a moment. She was so gorgeous and he couldn’t wait until he could kiss her again.

“So,” he asked after a moment of silence, “sex in the hot tub?”

Leni’s face turned red as she blushed.

“Is that something you’ve done before?”

The view of Leni changed as Leni adjusted herself on her bed.

“I’ve done stuff in a hot tub,” she explained. “Never sex though.”

“More stuff than what we did in the hot tub?” Mason asked her.

Leni pursed her lips together, not answering him.

“Leni,” Mason teased.

“Do you want the truth?” she finally asked. Mason nodded. “Okay, but you can’t get mad or judge me,” she said. “Two Christmases ago when we went skiing, I met a guy on the hill. He was really cute and he invited me to his family’s room. They had a hot tub on the balcony and,” she paused for a long moment, clearly worried about what Mason would think.

“And?” Mason asked.

“I took my bikini top off and then we made out,” she blurted out.

She hid her face in her legs, clearly embarrassed of the story, but Mason just smiled at her.

“Why are you ashamed of it?” Mason asked her. “Do you regret doing that?”

Without taking her face out of her legs, Leni answered. “No, I’m not ashamed,” she said, “I just don’t want you thinking less of me.”

“Why would I ever think less of you?” Mason asked. This caused Leni to pull her head up and look at him finally. “You weren’t with another guy at the time that this happened?”

“No,” Leni answered.

Mason shrugged. “So, why does it matter? You’re allowed to be sexually active and enjoy doing those sorts of things, as long as you are safe,” he told her. “And, for my sake, as long as it’s not with another guy when you are with me.”

Leni smiled and laughed. “You don’t think less of me for this?”

“God no,” Mason assured her. Leni looked down again, but she was still smiling.

“Leni,” Mason had to ask, “is this another thing that you are insecure about because of your ex-boyfriend?”

She went quiet again.

“Leni?” Mason asked after a minute.

“So that happened two Christmases ago,” she said again. “I was 16. Nothing else happened with that guy afterwards. We didn’t even exchange numbers. A couple months later, I started dating my ex, James. One night we were in my family's hot tub and I made a comment that it would be really romantic if it were snowing. He asked what made me think of that, so I told him about what happened with that guy at the ski resort. I didn’t think it was a big deal,” she explained. “It’s not like James and I were together when I met that guy, but he got so mad at me. Called me trashy for taking off my top for some guy I had barely met.”

Mason’s jaw clenched as Leni told her story. He didn’t know James, but he hated him.

“Leni,” Mason said when she finished. “I hope you know, there is nothing wrong with you exploring your sexuality. You can give me a list of every man, woman, person you have kissed, fucked, showed your boobs too, I will never think of you as trashy.”

Leni smiled, looking at Mason through the screen. “You wouldn’t think less of me for being with other people?”

“Absolutly not,” Mason said.

“I promise it hasn’t been that many,” she told him. “If you really want to know, including you, I think I’ve made out with six people and you and James are the only people I’ve had sex with.”

Mason shrugged. “Doesn’t bother me one bit,” he told her, smiling. “And really, if you hadn’t been willing to try things and explore, would you have even come down to my room that night?” he asked her. “And if you hadn’t, where would we be now?”

“That’s true,” Leni said, smiling.

Mason’s lips also turned up into a smile. He was happy to have given joy back to Leni for something her ex had made her feel ashamed for.

“Actually,” Leni said, adjusting the way she was sitting again. “You know something I’ve never tried before?”

“What’s that, baby?”

She bit her lip, staring down for a second, then looked up at him. “Phone sex.”

Mason grinned at her. “We could do that.”

Leni bit her bottom lip, a big smile growing on her face.

“How would we start?” Leni asked.

“How about,” Mason said, sitting up in his bed, “you take your top off?”

Mason watched as Leni shuffled around in her bed. She propped her phone up against something on her night side table so she didn’t have to hold onto it anymore. At this angle, Mason was able to see her full body as she sat cross legged. She was wearing a cream coloured tank top and a pair of black shorts.

Looking directly into the camera at him, Leni reached for the bottom of her shirt and slowly pulled it off and over her head.

Through the screen, Mason stared at her gorgeous tits. The sight of the round globes and perfect pink nipples had him instantly hard. What he wouldn’t give to have his tongue circling her peak nipple right now and listen to her moaning in pleasure.

“Fuck,” he muttered as he looked her over on the small phone screen. “I miss those tits.”

“What did you miss more?” Leni asked, sitting up on her knees. “My boobs or my pussy?” She pushed her shorts down and Mason was greeted with the sight of her shaven cunt. She sat up on her knees for a moment, letting him stare at her.

“God damn it,” Mason said, biting his lip. “Take those fucking shorts off and touch yourself for me,” he ordered her.

Sitting back on her butt, Leni pushed her shorts completely down her legs, getting naked for him.

“Are you going to show me your cock?” Leni asked him.

Sitting up off the bed, Mason did exactly what Leni had done. Balanced his phone on his night side table so the camera was facing him on the bed. Once it was standing upright on its own, Mason pulled his boxer shorts down, then scooted back on the bed so he was leaning against the wall and so Leni could see his erection on her side of the phone.

“Oh my gosh,” Leni said, looking at him. “You are so hard.”

“How wet are you?” Mason asked her.

Spreading her legs, Leni put two fingers between her pussy lips and rubbed herself a few times. Pulling them away, she brought her fingers to the camera and Mason could see her juices coating her. “That wet,” she told him.

“Fuck,” Mason groaned again. How he wished he could use that as lube for himself, but the lotion he kept in his side table would have to do for tonight. He would just have to pretend it was Leni’s cream.

Leni laid back on her bed, putting her head on her pillow. She was positioned sideways to the phone so Mason couldn’t see between her legs, but he was able to watch as she spread her legs and her hand went between them. He also had a great view of her tits bouncing as she touched herself.

Mason rested his back against the wall and slowly started stroking himself as he stared at Leni.

“Tell me what you’re thinking about,” he ordered her.

“I’m thinking about you touching me,” Leni told him. “Thinking about your hands and mouth all over my body.”

“Mmmm,” Mason moaned as his hand started working faster on his cock and he watched Leni pleasuring herself. “Where do you want my mouth?” he asked.

“On my lips,” Leni answered. “On my tits and eating out my pussy.”

Mason bit his bottom lip at the thought.

Leni continued rubbing herself. She was so wet that Mason could hear her movements. All he could think about was diving down face first into her cunt and sucking every drop from her.

Still touching herself, Leni turned her face to the camera and bit her lip when she saw Mason fisting himself.

“Remember when you were balls-deep inside me?” she asked him.

“I think about it all the fucking time,” he told her.

“How often do you touch yourself thinking about it?”

“At least three or four times a week,” Mason admitted. “More when you send me those gorgeous pictures of yourself.”

“Oh yeah?” Leni said, biting her lip. “Got a favourite?”

“Oh God,” Mason said, thinking back to all the pictures he kept in a hidden folder on his phone. They were all amazing, but there was definitely one he went back to over and over again. “I love the one where you are standing in the shower stall wearing the tiniest thong in the world and a wet t-shirt.”

Leni bit her lip, grinning at him. “Really? That one’s your favourite?”

“It’s so fucking hot,” Mason groaned out. Whenever he looked at it, he imagined taking Leni and bending her over then fucking her while hot water showered over their bodies.

“Your cock is so sexy,” Leni told him, staring at him. “I’m going to cum soon.”

Those words sent electricity through Mason and he knew he was close too.

“Keep rubbing yourself,” he ordered her. “Pretend it’s my fingers.”

Closing her eyes, Leni did just that. Imagined Mason’s body against hers. His hands on her pussy, getting her soaking wet and making her climax.

“Ohhh Mason,” she moaned.

Mason bit down on his lip and stared at her. Her breasts bounced with her movements and he could tell her body was starting to tense up. He squeezed his cock tighter and moved his hand faster up and down it, imagining he had inside Leni’s sweet pussy.

“Oh fuck, Mason,” Leni cried as she brought herself to orgasm. Her back lifted slightly off the bed as the pleasure rocked through her whole body.

Seeing her like this took Mason over the edge and he came hard on his hand. He moaned loudly as his semen spilled down his fingers to his groin and lower stomach.

They both took a moment to breathe, Leni with her head resting on her pillow and Mason still sitting against the wall, breathing deeply in and out. After a minute, Leni opened her eyes then turned to look at Mason.

Mason smiled at her. “Well?” he asked. “How was your first phone sex experience?”

Leni smiled back at him. “Amazing.” She rolled her body to face her phone, putting both her breasts on full display and Mason could make out a hint of her pussy lips between her closed legs. That sight alone could make Mason hard again instantly. “Thank you for doing that with me.”

“Anytime baby,” Mason said, smiling at her.

He reached over, picking his phone up off the night stand, taking a quick screen shot of Leni and quickly saving the photo to his special folder for another day.

“Are there any other sexual things you have always wanted to try?” he asked her.