My Roommate's Sister

In my second year of college, I roomed with one of my best friends, Andrew. Though he was a quiet guy, he was a wonderful friend—caring, considerate, funny, and always there. But it's possible that my most favorite thing about Andrew was his older sister.

Lily and Andrew were just a few years apart—she had just graduated college that year—but they were best friends. Perhaps naturally, I couldn't really imagine what she'd be like; was she just like Andrew, only female? Was she more outgoing than him. As it turned out, I got to learn the answer, and more, when Lily visited us in November of that year.

The first I saw of Lily was when I swung open our apartment door and found her sitting at our tiny table with Andrew, eating and chatting quietly in the way I'd seen him done every night we'd known each other. When I saw her, I had to keep my jaw from dropping. She looked unmistakably like Andrew, her elegant features resting in a soft, pensive look—and she had a tight, curving body, her skin kissed golden by the sun. Before she saw me, she stood and turned to grab something from the desk, and I saw that the view was just as good from behind: her brown hair cascaded down her back and was dyed blonde at the roots, and, more strikingly, her tight, well-rounded ass stuck out in her snug skinny jeans.

They looked at me. I quickly shook my head and looked away from Lily's body.

"Oh, hey," Andrew said. Lily looked at me for the first time, and I saw her hazel eyes glittering. "Nick, this is Lily. Lily, Nick."

She smiled bashfully. "Hey."

I sat down in the cushioned chair of the apartment, swiveling it around to face them.

"So," I said. "How was the trip?"

"Not bad," Lily said. "You can really feel the air get less hostile when you leave Massachusetts."

"That's the main reason we bought the fan for the apartment," I said with a laugh. "Gotta circulate all the positive air. Couldn't have anyone getting a case of the vapors."

She and Andrew laughed, almost the exact same laugh. But while Andrew looked away and continued munching on his food, Lily's gaze lingered on me, her hazel eyes gleaming.

The next few days, I joined Andrew and Lily on their adventures in the city, coming with them to see the monuments, peek through museums, and wander down the cozy streets. Although Lily was just as shy as Andrew was, their proximity to each other helped open each other up. Eventually, we found ourselves walking together as Andrew popped into a bathroom, and she opened up about what life had been like since graduation.

"Not a fan. I want to be a music teacher, but the jobs in my area have a lot of qualifications that make it a huge pain. So right now, I'm tutoring kids in music on the side."

"Ugh, that sucks, I'm sorry," I said. "At least you're getting to help those kids, though. I'm sure they're learning a lot. And, for what it's worth, I'm positive it'll work out in the end. Maybe it'll just be you leading an army of young musicians to the soil to demand a job."

"How'd you know my master plan?" she laughed. "Do you play music?"

"Oh, I'm terrible. I play piano for fun, but I don't think I have the hand/eye coordination for it."

She smirked. "I should give you a lesson sometime. I bet I could show you how to use those hands."

My eyes widened. Was this really happening? Was my roommate's older sister flirting with me?

Before I could answer, Andrew emerged from the bathroom.

"Stimulating conversation?" he asked.

Lily smiled. "Very stimulating." She looked at me, and for an instant, she winked. I couldn't find and answer, and was left watching her round ass away as she walked onward.

-

Lily left a few days later, off to stay at a friend's in the city before heading back home. I regretted not making a move, but how could I? What if I had misread things? How would my relationship with Andrew ever recover? So, regrettably, we said our goodbyes, and as she walked away with Andrew, I drank in the sight of her body poured into a thin yellow sundress that complimented her curves and showed off her creamy tan skin.

A few hours later, I was continuing to brood while vaguely pretending to study. My phone gave a ding. A message from Andrew: Hey, Lily said she left something in the room but I'm in class, would you mind letting her in?

I gulped. Would I be able to face Lily and stay coherent, much less help her? Still, I would hate for her to not get whatever she had left.

I met her downstairs in the lobby, where she greeted me with an elated smile.

"Oh, I'm so glad you're here! I appreciate this a ton!"

"Not a worry!" I said. "Or, I mean, not a problem. You know what I mean."

She laughed; her gaze lingered on me for a moment, and she bit her lip gently. I gulped, then pivoted on my feet and swiped my keycard to enter into the building.

When she reached my room, I spread my arms out widely.

"Welcome back to the humble abode. Can I help you find what you forgot?"

Lily laughed slightly. I turned, and met her hazel eyes with mine. She had a mischievous look.

"Well," she said, "I kind of lied to Andrew. I didn't forget any of my stuff here. I forgot to do something."

She stepped towards me, her long legs overtaking me in a moment. For a second, we were suspended in space, her lips inches from my own.

I'm not sure who moved their head first, whether it was her or me or both of us at the same time, but our lips were suddenly locked together, parting slightly to let our tongues dance around each other. She pushed me back towards my bed and pounced on me, devouring my lips as we leaned against my bed. After what might've been a minute or an hour or a hundred years, I broke away.

"This is unexpected," I said, dumbstruck. "But, I mean, good, obviously."

She smirked. "I've thought you were cute since the first time I came here. And well, I'm really horny. I didn't want to leave again without...saying an extra goodbye."

I felt her fingers clench around the bulge in my pants.

"May I?" she purred.

"After you," I said.

She grinned. Her hands made quick work of my pants, unzipping and unbuttoning me and then yanking my pants down to my knees. She gave me another kiss, then sunk to her knees, looking hungrily at my cock.

She ran her tongue along my shaft, sending electric shocks through my body, and gave the engorged head a tender kiss.

"Please," I whispered. She smiled, then obliged me.

I moaned in rapture as her mouth descended on my cock, her soft pink lips taking in my length and then going up and down. I looked down and soaked in the sight; something about seeing her head bobbing softly on my cock was especially hot—though it may have been that it was the best blowjob I'd received in my short sexual career. Clearly, the several years she had on me were doing wonders.

I yelped as I felt her tongue swirl around my cock, and as she took me further into her mouth, I felt a pressure building inside me. If I didn't act fast, this dalliance would be regrettably short.

"Hey," I said. She looked up at me, hazel eyes shining, my cock in her mouth. So hot. "Your turn."

She pulled herself off my cock and I helped her up, then, with her consent, eased her sundress off her radiant body. Beneath, she was wearing a bra with flowers printed across it and lacy red panties; she did a cute twirl, and I sighed involuntarily as I saw how well the bra contained her modest breasts and how amazingly the panties framed her tight, ass. I kissed her again, my hands reaching around to her ass and giving it a squeeze. Then, they slid down, picking her up by her golden thighs and laying her on the bed.

Now driven by the desire to please her, I planted kisses and nibbles on Lily's neck. She moaned softly, and I continued down her chest, pulling her bra open ever-so-slightly to kiss the globes of her breasts, then moved down her tummy and to her waistline.

"May I?"

"Be my guest."

I hooked my thumbs in her panties and pulled them down, exposing her beautiful pussy for the first time. I kelt before her like she was my goddess and began eating her out, flicking my tongue across her folds and concentrating my efforts on her clit. She moaned as I went on, encouragingly, and I took it further by teasing the slit of her pussy with my finger. She squealed, driving me mad with lust, and I lapped hungrily at her pussy, desperate to pleasure her; her moans continued and grew louder, then culminated as she ran her fingers through my hair and yanked hard.

"Fuck me," she commanded. "Fuck me now."

Obligingly, I quickly stood up and pulled off my t-shirt, leaving myself naked. In the meantime, Lily unclipped her bra, biting her lip and gazing at me coquettishly as she drop it and revealed her breasts to me. They, like the rest of her, were beautiful, full with the most perfect fine-tipped nibbles.

"You gonna stand there all day, or you gonna fuck me?" she said.

I obliged, climbing onto the bed and beginning to position myself over her. Lily, however, had other plans, and quickly took control of my skinny body, flipping me into my back and straddling me. She had a look in her eyes like she wanted to devour me whole, but instead of doing that, she lifted herself into the air and slid down on my cock.

I groaned as her pussy squeezed around me for the first time. Lily's pussy was soft and velvety and hot and tight, and even the thought of it could make me cum. She moaned along with me as she began to go up and down on my cock, her breasts shaking gently as she bounced up and down on it, gradually building up her pace until she was fucking me wildly.

"You like this?" She said. "You like fucking this tight little pussy with that big, hard cock?"

"Fuck yes," I replied, sweat beading on my forehead. "I love feeling your pussy. I love making you moan. I want to fuck your pussy all night."

The dirty talk stimulated me and such that I couldn't help myself, and I began to fuck Lily back, thrusting my cock in and out to meet her riding. Her bouncing became faster, more manic, more hurried. My hands shot around to grip her tight ass, my only leverage in the hurricane of our sex. And God, it was incredible.

"Oh God," she moaned. "I'm gonna cum. Fuck me. Fuck me." I obliged, fucking her as hard as I could.

"Lily," I gasped. "I'm getting close."

"Cum with me. Fill up my pussy with your cum. I want to feel your cream."

I tried to fuck her even harder, though with her rapid bouncing, there was only so much I could do—but my efforts, nonetheless, paid off. Her moans crescendoed into a scream of ecstasy and I felt her explode on my cock, her juices soaking me as her pussy squeezed around me. At that point, it was too much for me to handle: I moaned, gripped her ass for dear life, and came, firing my hot cum inside her as her pussy miked every drop from me.

Lily sighed and slumped forward onto my chest and lay there for a while. I slid my cock out of her and she planted a kiss on my lips, then sprung up and went to the bathroom to clean up; I was in shortly after her. After, we hung around the room, chatting about anything and everything. My exhaustion forced me to drop into our comfy chair, exhausted, and I watched as Lily absently opened my desk drawers.

"That was great," I said suddenly.

She smiled. "Yeah, it was. I think that—"

Suddenly, there was a high pitched beep as a keycard swiped on the other side of the door, and Andrew entered. He smiled widely at Lily, seeming not to mind that she had stayed longer than would have made sense.

"Hey!" he said. "Did you get what you forgot?"

"I did," she said with a sly smile. "We were just talking about how I should come down again soon, to hang out more." She looked at me expectantly.

"Oh, yeah," I said. "It's great to have you."

Andrew agreed, and he and Lily soon left the room so that he could help her find her friend's place. On her way out, she gave me a surreptitious wink.

As the door closed behind her, I reclined back, astounded that it had all happen. I was there for several minutes, ruminating, until my phone buzzed. It was a text from a number I didn't recognize.

Thanks for helping me find what I forgot. Think I left something in the desk drawer, but you can keep it ;)

I furrowed my brow, then realized the meaning of her text. I sprung to my feet, then hurried to my desk drawer and tore it open—to find Lily's lacy red panties, which were soaked.

I gulped and began counting the days until her next visit.