My Roommate's Hot Little Sister (closed for BudLeonard and myself)

[slippedhalo]

Jessica just ended a great first year of college. It was mid-May and since her brother Kaleb's college was just in the next town her mother suggested that they both share Kaleb's car and drive back home for their summer break together instead of him driving and her having to spend the money to fly. That would be perfect except that Kaleb's school isn't quite out yet. He still has another week and a half of exams and scheduling before he can head home. Jessica decides to spend those weeks at the small on-campus apartment him and his roommate share while she waits for him to be finished.

Jess had never met Kaleb's roommate before but had heard he was a nice guy, excellent at some of Kaleb's favorite sports, and made a kick-ass cup of coffee. What she hadn't been told by her big brother was that his roommate was cute too.

As she was let inside by the new stranger she introduced herself and the two hit it off right away by both making fun of Kaleb mercilessly.
One reality of her brother's college life that wasn't a part of Jessica's was that Kaleb was often not home at night. He was a playa', a ladies' man and rarely spent the night in his own bed. This left Jessica with one awkward evening home alone with the roommate, trying to stay out of each other's way and remain polite, and a second day wondering if it would happen again.

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Jessica Killian
Age: just turned 19
Phys. Desc. : See photo in sig.
Major: Special Education

 

[BudLeonard]

David Watson
22 years old
Medium Build, but Muscular and Toned
Brown Hair, Glasses, Blue Eyes

David had heard a lot of stories about his roommate Kaleb's sister, but seeing her in person was a story in and of itself. David had always had a thing for redheads, and she was pretty damn gorgeous.

To go along with that, she had a great personality, too -- she knew exactly what he was talking about, and could bust Kaleb's balls with the best of them.

Still, there was an awkwardness that went beyond attraction between them, and as Kaleb went out for yet another night, David found himself unable to sleep. He read, watched some tv, but nothing...because whenever he closed his eyes, he saw Jessica there.

The night was hot, too. Damn hot. He'd eventually kicked the sheets away and stripped down to his boxers. Still, the sweat trickled down his skin. It made him thirsty.

As he got up to use the bathroom, he saw the door to the room where she was staying. It was open.

Maybe just a peek, he thought, as he headed down the hall...

 

[slippedhalo]

Jessica had been sleeping on the cot the boys kept in the laundry room/ office. Being that this room had the smallest window in the apartment and nofan, she was sweating and hot most of the night and had a hard time falling asleep. When she finally did, she had strange dreams. In one she was on a deserted island with her ex boyfriend but then the girl he cheated on her with showed up and there was a catfight...this melted into another dream on a beach but this time David, her brother's roommate was there and they were kissing, getting pretty hot and heavy too...Jessica was really liking this dream.

 

[BudLeonard]

David stood at the door, watching her toss and turn. It was clear she was having some kind of sexual dream, and it turned him on. His cock began to stir, and he walked forward into the room.

He put his hand on her ankle, gently caressing her flesh for the first time...

 

[slippedhalo]

A feeling outside of her dreamstate awoke Jessica with a start. She sat up on her elbows and looked up into the darkness, still a little groggy, and forgetting where she was.

 

[BudLeonard]

Taking her in his firm hands, David pushed Jessica back onto the bed.

"Shhh," he said. "It's all right."

His hands began to roam up her legs, caressing her muscular and toned thighs outside her pajama bottoms, moving upwards...

 

[slippedhalo]

"David?" murmured Jessica, confused. "What are you doing?" she asked...This was, oddly, a lot like her dream so she wasn't certain if she was awake or still dreaming.

 

[BudLeonard]

David didn't respond, but he did sit down on the bed as he ran his hands up her thighs further. He was at her hips now, and he started to push her pajama top away from them, giving him better access to her belly.

He gently stroked the exposed skin, moving in smooth, soft circles...

 

[slippedhalo]

Jessi was starting to realize this wasn't her dream at all but reality. "David! Don't...we can't..." she protested, even as he pulled her covers away and climbed on top of her. Truthfully, after the dream she'd had a small part of her thought it might be fun to fool around with her brother's roommate but she was also very practical and whispered, "What if Kaleb comes home and finds us?"

 

[BudLeonard]

David whispered, "He won't. I saw the girl he went home with, or was planning to go home with. They'll be up all night, having fun."

He cleared his throat, suddenly shy. "So, you know, I thought maybe we could have our own fun."

His hands continued to caress her belly, feeling her smooth skin, until his hands went up to the last button of her pajama top and started to snap it open from the bottom up...

 

[slippedhalo]

"I hardly know you, though... and I...I don't have a lot of experience." sputtered Jessica. As his hands snaked a little higher up under her top she grew nervous and pushed him away, "Maybe you should go. This seems wrong."

 

[BudLeonard]

She pushed him away and he gently pushed her back onto the bed.

"It's okay, Jessi. It's going to be okay."

Her pajama top was almost halfway undone. He peeled it away on each side, leaving her entire stomach from her naval to the swell of her breasts exposed.

He bent down and ran his tongue over her belly, giving her a long lick from her bellybutton to the bottom of her breasts. One hand cupped her most private place between her legs, massaging her over her pajamas.

"Besides, how can something that feels this good...feel so wrong?"

It was lame, but as he continued to kiss and caress her, he hoped it worked...

 

[slippedhalo]

She closed her eyes, enjoying the feel of his body pressed against hers, the forbidden touch of his hand between her legs, the erotic feeling of his tongue licking her hot skin..."Mmmmm-David...." she sounded as if she was protesting, but her body was enjoying this and she helped him to unbutton the rest of her pajama top, exposing her pale breasts and her erect, pink, rosebud nipples pointing at the ceiling. She wondered if he was even aware that he licked his lips hungrily as her breasts were exposed to his view. As he closed his mouth down upon her breast her resolve broke down. "mmmmaybe if we're not too loud..."

 

[BudLeonard]

Her breasts were beautiful, pale and firm, and he cupped one of them as he brought it to his lips to suck on it. He ran his tongue along the nipple, biting it lightly, feeling her moan "M-m-maybe if we're not too loud."

He smiled, and continued his ministrations on her breasts. He slipped her pajama top off and tossed it to the floor.

Gently, he took her hand and led it to his cock, which was threatening to break out of his boxers.

His other hand, though, continued to caress her belly, slipping his fingers underneath the waistband of her pajama bottoms...

 

[slippedhalo]

She sighed as he sucked and teasingly bit her nipple. But soon she gasped, as her pants were coming off and only her thin pink panties separated her from true trouble. "David...I...I haven't..." she wanted to tell him yet was afraid he'd laugh at her and think she was a baby if she admitted to him she was still a virgin. "...be careful." she finally managed to say.

 

[BudLeonard]

As he tossed her pajama bottoms on the floor as well, he gazed down at her pretty pink panties. She looked so soft and innocent there in her bed. When she asked him to be "careful," well, he'd been with enough girls to know what that meant.

He smiled down at her, running his fingers over her panties before planting a soft kiss onto the fabric. "It's okay. We don't have to do anything you don't want to do."

He stood up, then, releasing her from his touch, and shoved his boxers to the floor, exposing himself and his full, rich manhood to her.

 

[slippedhalo]

Jessica's eyes widened as she took in the full length and girth of David's erect cock. He was certainly no boy, quite large and the look of pride on his face as he watched her study him told her he knew it too. She had qualms about losing her virginity before and yet she knew she was also so fed up with people treating her like some fragile, precious little girl when they found out about it... She nodded her head, deciding for herself she would rather get it over with here and now with a man who seemed nice and was probably the best fuck she'll ever have with a college aged guy then wait for some middle aged loser when she was so old it no longer seemed to matter anymore.

 

[BudLeonard]

David saw the lust in her eyes, saw the change in her, and smiled.

He climbed back onto the bed, and began to massage her pussy through her panties, before slipping his hand down underneath to caress her wetness.

His mouth returned to her breasts with an unbridled lust, sucking on the nipples and biting her flesh once more.

He gently took one of her hands in his and guided it down to brush her fingers along the tip of his cock...

 

[slippedhalo]

Jessica gasped as he moved his hand to caress her inside her panties but it felt so nice, his fingers moving to trace her dampness, that she didn't mind a bit. His suckling of her nipples made her only grow more wet too and she sighed and moaned a little beneath him as he played with her. Soon, her hand was on his cock and she moved gently to caress his phallus, and then built up some of a steady rhythm, jerking him off as he continued to pleasure her.

 

[BudLeonard]

Her hand felt so nice. They kept at that for a while, Jessie stroking his cock, he massaging her pussy.

Eventually, David pulled Jessie up off the bed. He stood her in front of him, and slipped his fingers inside the waistband of her panties, before peeling them off and onto the floor.

He looked at her, naked, standing there, shy, in front of him.

"Jessie," he said. "I want you to put your mouth on me."

 

[slippedhalo]

"David...I'm scared you're going to gag me on that huge thing." admitted Jessie, not saying no but afraid to obey too.

 

[BudLeonard]

David cupped her pussy again, this time slipping the tip of a finger inside her wetness. "I could never, would never, hurt you. But I need to feel you on me, tasting me."

He took her shoulders and gently guided her to her knees...

 

[slippedhalo]

His fingers felt so good as he touched her...Jessie gave in and let him push her to her knees, she took his erection in both of her hands and looked at it a moment. It was like something straight out of a porn film, she thought as she studied it...flipping her red hair back over her shoulder, she bent to taste him...salty, not sweaty and gross like she would have imagined...soon she was licking the tip and then once comfortable with that, she had wrapped her lips around the head and was slowly sucking and licking as if her were a lollipop.

 

[BudLeonard]

Although it was clear Jessie was inexperienced, she wasn't particularly bad at sucking cock. David leaned back, deciding to enjoy it.

"That feels so nice," he said as she worked him like a lollypop.

 

[slippedhalo]

"Mmmfh?" she mumbled an incoherent reply as her mouth was filled with cock. Her dark eyes darting up to look at David as she worked...was she actually doing this? Sucking her brother's roommate's dick? She had to admit to herself the whole situation felt very surreal to her, but that didn't stop her from going on.