My Roommate's Sister

Slowly, Mason and Leni walked back to the dorms, holding hands and enjoying the cool night air. When they had been outside for about five minutes, Mason noticed Leni shivering. She was only wearing a long skirt and a button-up denim blouse that had short sleeves, so the wind must have been really cold on her arms. Unzipping the UF sweater he was wearing, Mason slipped it over and offered it to Leni.

She took it, smiling. “Thank you.” They took each other's hands again and continued their walk.

Mason smiled so much as they made their way across the quad. All he could think about was starting in September, this was going to be his normal day-to-day. It wouldn’t only be on weekends and holidays he’d be seeing Leni. They would be able to see each other everyday, go out to the bar or local restaurants whenever they wanted and not have to worry about driving over an hour to meet each other. She could be in his bed, or him in hers, as many nights as they wanted. He was even excited to one day bring her home to Maine so she could meet his family. He knew his mom would love Leni and welcome her into the family.

Unlocking the door to his dorm room, Leni stepped into the dark room first, followed by Mason who stopped to lock the door behind himself. Then he turned to face Leni. The room was dark, but the moonlight shone through the window, lighting her in the most gorgeous way.

In the seconds Mason was facing away from her, Leni had removed her cross-body bag from around herself and was holding the strap in her hands. Reaching for it, Mason took it and placed it on top of his desk.

Approaching her, Mason wrapped his arms around her and pulled her body into his. Leni embraced him in return. They didn’t kiss yet, they just held each other, Mason looking down and Leni looking up into his eyes.

Leni’s hair had been pulled back into a ponytail all day. Gently, Mason pinched the fabric elastic and pulled it down, releasing her hair from the tie. Her reddish brown hair framed her around her beautiful face and Mason stared at her a few seconds longer before he leaned down and kissed her.

As they kissed, Leni held onto Mason’s body, holding him as tight against herself as she could. Mason’s hands went to Leni’s face, holding her gently and moving his lips against hers. He wasn’t sure what made it so special, but he absolutely loved kissing this woman.

Leni let go of Mason, taking her arms off of him, but continued kissing him. She slipped the unzipped sweater she had been wearing off her shoulders, letting it fall to the floor at their feet. Mason’s hand slowly went down Leni’s neck and shoulders, stopping to rest on her breasts for a long moment, then going to the buttons of the blouse she was wearing.

Mason took his time undoing each button on Leni’s shirt, never letting his lips leave hers. He went from the top button, very slowly working his hands down. When he finally undid the bottom and last button, he gripped the fabric in his hands, then pulled it down her shoulders and off her arms. It dropped to the floor on top of the sweater.

As much as Mason wanted to look at Leni, he could not stop kissing her. Instead, he put his hands back on her breasts, feeling the lace of her bra on the palms of his hands. They did have to pull away from each other though when Leni lifted Mason’s shirt up and over his head.

They stood in front of each other, Mason naked from the waist up and Leni in only her bra, just looking at one another. Leni was wearing a white lace bra Mason hadn’t seen yet. It wasn’t completely see-through, but he was able to make out the colours of her areolas. He could also her nipples, already hard and poking into the fabric. Unable to stop himself, his hands went back to her breasts. He gently cupped them, running his thumbs over her hardened nipples. Leni sucked her bottom lip into her mouth and sighed quietly as he touched her.

Reaching behind herself, Leni took the clasp of her bra in her hands and slowly undid it. Mason moved his hands away from her chest, allowing her to take the bra off herself, adding it to the pile of clothes on the floor. He kept his hands away for a moment, just staring at her bare chest. He’d seen her breasts several times, but he couldn’t help himself. He was beyond attracted to his woman. In his eyes, she was the most beautiful woman in the world.

His hands went back to her chest and he squeezed them gently. He was able to get an audible moan from Leni’s lips when he circled her nipples with the tips of his thumbs.

“Mason,” she breathed out, closing her eyes and feeling his touch on her body.

Hearing Leni say his name in the most sensual way, it ignited the caveman in Mason. Wrapping his arms around her legs, Mason picked her up and carried her to his bed, sitting her down on it. Kneeling in front of her, Mason took her foot in his hands and took off her white sneaker, tossing it to the floor then doing the same thing to her other shoe.

Looking up at her, Mason and Leni held eye contact as he took the waistband of her skirt in his hands and slowly pulled it down and off her legs. Leni lifted her butt off the bed to assist him. Then she sat on the bed wearing only a pair of white panties.

With her legs spread slightly, Mason could see two wet stains on the crotch of her panties. One larger that looked like it had dried down, possibly from earlier today, and a smaller one in the center of the other one, still wet to the touch.

“Can I please take off your panties?” Mason asked her softly.

Leni nodded. “Yes, please.”

Leni raised her rear of the end slightly, allowing Mason to easily pull her panties down her legs and off her body. She sat back on the bed, leaning back slightly and Mason looked over his beautiful girlfriend, now completely naked in front of him.

Staying on his knees in front of her, Mason looked at the pussy on display in front of him. Since they started seeing each other, Leni had kept herself completely shaved. Not because Mason had asked her too, just because she wanted to.

After a minute of staring, Mason looked up at her face. “You’re so gorgeous,” he whispered. Leni was smiling at Mason’s words, but as he spread her legs and slowly moved his head towards her center, she bit down on her bottom lip.

Wrapping his arms under her legs, Mason pulled her slightly so her butt was right on the edge of his bed, then he leaned into her. Without touching her yet, he smelt her, breathing in the intoxicating scent of her sex and arousal. Slowly he brought his face to her inner thigh and he lightly pressed his lips to her skin, kissing her so incredibly gently.

Leni moaned so quietly as she felt Mason’s lips on her legs. He was so close to her most sensitive parts, but not quite there yet. She wanted him there so bad, but she didn’t want to rush him.

After what felt like forever, Mason centered his face, lining his mouth up to her core. He looked down at her, biting his lip as he stared at the most beautiful pussy he had ever seen, then looked at her. She was watching him so intently.

“Can I?”

Leni nodded again, her head shaking up and down so fast.

Using his fingers, Mason spread the lips of her pussy apart. He took a moment to stare at the wetness that had already formed there. Then he stuck out his tongue and leaned in, pressing his muscle to her sex.

“Oh my God,” Leni cried the moment she felt his tongue on her.

Mason licked and sucked on her, loving her taste. She had a delicious sweet flavor that he absolutely loved.

After spending a few minutes licking up and down her pussy, Mason found her clit. He pulled it between his lips and sucked hard on it.

“OHHHH!” Leni moaned loudly.

Looking up at her, Mason watched as Leni leaned back, closing her eyes and pressing her lips together as he pleasured her. Mason was so turned on watching her. The way her chest moved up and down as she tried to keep her breathing under control as she got eaten out, her hard nipples sticking up from the center of her breasts. Just looking at her, Mason was rock hard.

Using the tip of his tongue, Mason glided his tongue from the bottom of her sex up to the tip top, sucked her clit, then did it again and again. He could feel Leni’s legs start shaking as he continued this erotic torture on her, but he didn’t stop. He just sucked her a little longer, or flicked his tongue a few extra times over her bud.

“Mason!” she cried.

He could see she was clenching the bed sheets in her fists. He could tell from the way her body was reacting and the way she was moaning that she was close and he was so ready to taste her climax on his face.

Using both his hands, he spread her legs as much as he could and drove his face as far into her cunt as he could.

“OH GOD!” Leni nearly screamed. He made his tongue as wide as he could and lapped up and down her. One second he would be sticking the muscle in and out of her hole, fucking her with it, the next he’d be flicking the tip of his tongue on her clit. “Please don’t stop,” she begged him. Wild horses couldn’t pull him away from her.

He inserted his tongue in and out of her, over and over again, until her whole body was clenched up then he pulled her clit into his mouth and sucked it hard until she cried out as her whole body orgasmed.

While Leni caught her breath, Mason removed his mouth from her pussy and gave her inner thighs soft kisses again. He gave her a few minutes to settle herself and her breathing and when she opened her eyes and looked towards him, he stood up.

Bending down, he pressed his lips to hers and kissed her hard. When he stuck his tongue into her mouth and heard her moan, he wondered if it turned her on to taste herself on him.

As they kissed, Mason undid the button and fly of his jeans. While he pushed his pants and boxer briefs down then kicked them off his legs, he never stopped kissing Leni. Once his pants were completely off, Mason carefully pushed Leni back so she was laying on the bed, rotating her at the same time to place her head down on his pillow.

Before joining Leni on the bed, Mason took a moment to stand back and look over her. She lay completely naked on his bed. Her arms were resting above her head, showing confidence that she didn’t need to cover herself from him. The moonlight shone in through the window, lighting her in the most beautiful way. She looked like a Goddess the way she laid there, waiting for him.

He didn’t make her wait long, climbing onto the bed and gently putting himself on top of her, lifting the blanket as he went down and placing it over their bodies. Their mouths met again and Leni held Mason’s face, holding him like she never wanted him to leave her again.

Carefully, Mason ground his erection against Leni’s naked sex. He wanted her to feel him, see how hard she had made him, but he was cautious to not push himself fully into her. He let his cock stroke her though, feeling himself rubbing between her pussy lips. The feeling of him teasing her had Leni moaning into Mason’s mouth.

Mason attempted to reach and open his nightside table drawer while still making out with Leni. He was able to find the handle on the drawer and pull it open, but after a minute of his hand moving around the open drawer, struggling to find the box of condoms he knew was in there, he released Leni’s lips so he could look properly.

Leni watched as his hand rumaged through the drawer, finally pulling out the box of condoms he bought a few months ago that they had been slowly going through. Mason pulled a few out of the box, ripping one of the end, then placed the box on top of the unit, next to his alarm clock. Sitting up, he opened the foil packet, pulling the latex condom out and began rolling it onto his erection.

“I’m going to start the pill,” Leni told him.

Mason looked down at her. “Really?”

She nodded.

“When you’re on it, are you comfortable not using condoms?”

Her hands touched him, rubbing up and down his sides. “With you? Yes.”

Tossing the empty packet to the floor, Mason leaned down, kissing Leni again. This woman was absolutely amazing. Fucking her already was the greatest feeling in the world. He couldn’t wait to try it without the barrier of a condom.

Using his knee, Mason spread Leni’s legs further apart and, while still kissing her, he lined himself up with her entrance, ready to push himself in now that he was wearing protection.

“You ready?” he asked her, between kisses.

“Yes,” she replied.

Slowly, Mason inserted his length into Leni, taking his time and letting her feel every inch of him.

“Oh gosh,” Leni moaned, feeling him.

Leni’s tight cunt squeezed Mason’s thick cock as he went further inside her. “Fuck, you feel so good,” he groaned into her neck.

As he went deeper, he could feel Leni’s hands on his back and her nails digging into his skin.

Once he was fully inside her, he just stayed there for a minute, enjoying the sensation. “I love feeling you around me,” he told her.

“I love you being in me,” she replied.

Keeping his cock there and not moving it yet, Mason kissed up Leni’s neck, making his way back to her lips. He was going slow because he wanted this time with Leni to be different. He wanted to show how much he cared about her and didn’t want it to be rushed.

“Leni,” he breathed against her mouth.

“Mason.”

Pressing his lips to hers, Mason slowly began pulling himself back and pushing in. Between the lubrication of the condom, plus how wet Leni was from him eating her out, Mason’s cock slid in and out of her with ease.

As he continued thrusting into her, it felt like she was getting tighter and sucking him in, pulling him deeper into her cunt. It took everything in him to not go full caveman and just start fucking her like crazy.

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

He buried his face into her neck, kissing and sucking on her skin while he pushed himself deep into her.

“Mason,” Leni moaned loudly.

“Yes, baby,” he groaned back, breathing against her neck. “Is this okay? Does it feel good?”

“It feels so amazing,” she told him, digging her nails deeper into his back. “Please don’t stop,” she begged.

“Never,” he promised her.

He continued the same speed, slowly pulling out until there were only a few inches of his cock inside her, then slowly pushing his entire length back in. When he’d pull himself out, he would wiggle his hips around, teasing her before going back in. When he was balls deep in her, he would grind his hips into hers, accentuating his length and thickness.

“Oh God,” Leni cried. “You’re so huge.”

“I fit perfectly in your tight cunt,” he told her. “I can’t wait to fuck you without a condom and cum inside your perfect pussy.” He raised himself off her body, very slightly and drew a finger from her neck to her breast, circling her nipple with the tip of his finger. “Watch my seed drip out of you like I watched it drip down your tits after I came all over them.”

“Please,” she begged him, after several minutes of his slow fucking. “I’m so close. Please make me cum, Mason.”

Teasing her, he continued his slow pace. Even going so far as to pull nearly his entire cock out of her. He couldn’t help but chuckle when he heard her whine.

“Mason,” she cried. “Please.”

Holding himself over her, he pushed his length back into her, stopping to lean down and kiss her hard on the mouth. Then he pulled out and began fucking her the way she was begging.

“Yes,” she moaned. “That feels so good.”

“You feel so fucking amazing,” he told her, picking up his pace.

He groaned as he could feel her sucking him in and tightening up. He knew she was close, and wanting to finish with her, he sped up a little more, pushing himself into her as hard as he could with each thrust.

He continued thrusting into her, keeping the same pace and rhythm until he started to feel his cock contracting inside her. Then he sped up and pressed himself into her as hard as he could.

“Yes, yes, yes,” Leni moaned as her body started to clench up.

“Cum for me, baby,” Mason ordered her, looking down at her. Her eyes were shut and she was biting down on her bottom lip. She looked beyond gorgeous and sexy.

At the same time, Mason and Leni moaned loudly as they both came at the same time. Mason dropped down and rested his head down into the crook of Leni’s neck as he felt his cock behind drained into the condom he wore. Leni held Mason against her, wrapping her arms around his sweaty body. They both breathed in and out deeply, coming down from the orgasms they both had.

After a few minutes, Mason raised himself up again, only to bring his face down to Leni’s, kissing her soft and passionately. Carefully, he held her body and rolled them so they were side-by-side on the bed.

They held each other and kissed for a few minutes. At some point, Mason’s cock fell out of Leni’s pussy, but neither of them noticed as they just continued making out with one another.

After a long time, Mason slowly pulled away from Leni, opening his eyes and looking at her. Leni’s eyes also opened and they stared at each other, smiling. Mason delicately pushed a loose strand of Leni’s hair out of her face, then kept his fingers on her face, caressing her.

“That was different,” Leni commented after a long moment of silence.

“Different?”

She shrugged. “A lot slower than normal,” she tried to explain. “Not in a bad way, but like, very loving and passionate.”

Mason bit her lip, looking over her face. “There’s a reason for that,” he told her.

“Oh yeah,” Leni said, touching her hand to his chest and running it through his chest hair. “And what’s that?”

“I love you, Leni.”

Leni’s eyes shot up, looking directly into Mason’s.

“What did you say?”

Taking her hand that was on his chest into his hand, Mason held it tight, never breaking eye contact with her. “I’m in love with you Leni,” he repeated, softly. “You are the most amazing and incredible woman I have ever met. Being with you, even when we’re long distance, it always felt so easy. I love talking to you and being around you. We have the same values and wants for the future. I think it also goes without saying that we are very compatible sexually as well."

Leni was biting her bottom lip, but she had also started smiling.

Mason shrugged. “Yeah, I have been thinking about it for a while and I really wanted you to know.” He took her face gently in his hands, looking into her eyes and repeated. “I love you, Leni Hart.”

Leni was silent for a few moments, then she smiled and spoke. “I love you too, Mason Bradley.”

Mason didn’t think it was possible to smile as big as he was now, hearing Leni repeat those three words back to him. Still holding her face, he pulled her towards him and kissed her.

“OH MY GOD! MASON, WHAT THE FUCK?”

It had been a few hours since Mason and Leni had fallen asleep together in his bed. After Mason’s confession, he had made love to Leni two more times before they both passed out from exhaustion. Hearing the door slam followed by the loud exclamation, they both woke up violently and quickly realized the voice belonged to Josh, who was standing over Mason’s bed and staring down at his best friend, naked in bed with his step-sister.

“Josh!” Leni said, startled, seeing her older brother. She sat up in the bed and used the blanket to hide herself. Though she had already been mostly covered, she pulled the sheets all the way up to her neck, as if that would make Josh suddenly unaware of the fact that she was naked underneath.

“What the fuck is going on here?” Josh demanded from the two of them.

Mason awkwardly reached to the floor, grabbing his discarded boxers then slipping into them while remaining under the covers. Once he had them on, he stood up from the bed and approached his roommate. “Josh,” he started, “it’s not what it looks like.”

“Looks like you are naked in bed with my sister,” Josh said. There was anger in his voice that Mason had never heard before.

“Yes, we were,” Mason said, looking towards Leni, sitting terrified in the bed. The whole scene, Mason realized, did not look good. Not only was he in bed with Leni, completely naked, but there were three opened condom wrappers on the floor next to their clothes plus the used condoms discarded in the garbage bin. “Josh, please understand, this wasn’t just a random hook-up with your sister.”

“Don’t ‘Josh please’ me, Mason,” Josh shot back. “I told you about Leni’s past boyfriends, how they treated her and how much I hated it. Did you not hear me tell every guy I introduced her to that she’s my sister and is off-limits. Then you go and sleep with her behind my back.”

“To be fair though,” Mason said, “you technically never actually said that to me.”

The look Josh gave Mason had him backing away from Josh in fear of getting his head ripped off.

“Josh,” Leni said, trying to get a word in and calm her brother down. “Listen to him. I asked him not to tell you.”

“Leni,” Josh said sternly. “Get dressed and I’ll drive you back to mom and dad’s hotel.”

“Josh, please,” she pleaded.

“LENI!” Josh exclaimed, stopping her. “Please,” he said, closing his eyes. “Just get dressed,” he said through his teeth. Leni and Mason glanced at each other and they shared a look of worry in their eyes.

Keeping the blanket wrapped around her, Leni stood up from the bed. She used one hand to hold up the blanket to keep herself covered and used her free hand to pick up her clothes. The dorms only had a communal bathroom that was used by everyone on the floor so Leni stayed in the room, pulling on her clothes underneath the blanket to keep herself covered the entire time until she was fully dressed. She also stayed in the room, not wanting to leave Mason alone with Josh. The three of them remained awkwardly silent the entire time, the only sounds being made were of Leni pulling her clothes back onto her body. After she was finally dressed, she removed the blanket from around her body and laid it back down on Mason’s bed.

Finding her cross-body bag on Mason’s desk, Josh picked it up and handed it to Leni. “Let’s go,” he said to her, immediately turning to the door after she had taken the bag.

“Okay,” she responded softly.

She turned her head, looking at Mason. He looked down at her and smiled weakly. ‘It’ll be okay,’ he mouthed to her. She pursed her lips together and nodded once, then turned to Josh, standing across the room and holding the door open for her. She walked through the door, leaving the dorm room. Before Josh slammed the door on Mason, he shot him the worst glare Mason had ever seen come from his friend.

Mason paced the small dorm room. He didn’t know how long Josh would be gone, he didn’t even know if he planned on coming back to the room once he dropped off Leni, but he had to come back at some point and Mason was going to be ready to talk to him whenever he returned.

After what felt like hours, Mason heard the sound of the doorknob rotating. He turned to the sound and watched as the door opened and Josh entered the room.

The two roommates and friends stared at each other for a long moment, neither of them saying anything. After a long minute, Josh stepped into the room, closing the door behind him.

“Josh,” Mason said, “I’m sorry you found out about Leni and I like that, but you need to know, it wasn’t just a random hook-up or one night thing,” he tried to explain. “I really, really care about her, but we agreed to not tell you just yet.”

“Just stop,” Josh said, abruptly, facing Mason and holding up his hand, stopping Mason’s rambling. “Leni told me everything.”

Mason stared at Josh unsure if this was a good thing or not.

Josh sighed loudly and sat down on his bed. Mason sat across from him on his own bed.

“She told me that she went to you first on Thanksgiving weekend and that you two have been seeing each other since then.”

Mason stared intently at his friend as he repeated back everything he had been told by Leni.

“She said that she asked you not to tell me about your relationship, that she told her mom a while back but she wanted to wait just a little longer before she told me and my dad. She said you two had sex on Thanksgiving and that you’ve met up a few times since November and have been intimate with one another. Frankly,” Josh said, putting his head down into his hands, “I know way more than I ever wanted to know about my step-sister’s sex life.”

Mason couldn’t help a small smile grow on his lips.

Josh looked back up at Mason. “But the main thing she told me was that you make her feel beautiful and special. That you have never once judged her or made her feel like she’s done something wrong.” Josh looked directly into Mason’s eyes from across the room. “She said you have never pressured her into sex, that you ask consent every time you’ve kissed or touched her. You make her feel seen and like she has a choice to say no, but that you would also respect her if she did say no.” Josh paused for a few long seconds before finishing. “She told me you two said ‘I love you’ last night.”

Neither of them said anything for a minute.

Finally, Mason spoke. “I’m sorry you had to find out this way, Josh. We did plan on telling you.”

Josh held up his hand again. “That was probably the worst way to have found out, but I would have freaked out no matter how I was told.”

The two friends looked at each other and Mason happily smiled when Josh smiled at him.

“To be honest though, Leni is going to date. No one can stop that,” Josh said. “And you were right, I technically never said to you specifically not to date my sister, but maybe that’s because I knew if you did, it would be okay. There are a lot of shitty guys out there, but you aren’t one of them. So, if Leni is going to date anyone,” Josh told Mason, looking into his eyes, “I’m glad it’s you.”