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Playing the Part

Playing the Part

by Undercurrants
19 min read
4.78 (49500 views)
brothersistersibcestbrother sisterbrother sister sex
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Note: This story contains sexual encounters between siblings, in case that's not your thing.

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"Just got to the house." My sister text me while I was waiting on my Uber from the airport. "This place looks amazing!"

"Awesome." I shot back. "Weather looks like it'll be hot and sunny all week."

Just then, I saw the car I was waiting on pull up to the curb outside the arrivals exit. I waved to the driver and picked up my duffel bag to make my way over to him. I was climbing into the back seat when my phone buzzed again.

"You almost here?" My sister wrote.

"Just landed." I wrote back. "Getting in the Uber."

As the car pulled onto the airport expressway, I caught a glimpse of the surrounding landscape of South Florida. Sunshine and palm trees as far as the eye could see. I opened my phone's camera, switched it to selfie mode, then snapped a photo of myself with my sunglasses on with the lush Floridian landscape zooming by window behind me.

"This definitely beats being stuck back home in Massachusetts for spring break." I wrote to my sister and sent her the selfie.

Several minutes later my phone buzzed. I opened my sister's text and gasped audibly.

"Everything okay?" The driver of the car said in a thick Cuban accent and glanced back at me in the rearview.

"Uhh..." I stammered, almost unable to take my eyes off my phone. "Yea, I'm good. Sorry."

The driver shifted his attention back to the expressway and I looked back down to my phone screen to see the selfie my sister sent me. The very provocative, very revealing selfie. My sister was laying on a poolside lounge chair, the picture taken from above her featuring her smiling face, and a deep and vast canyon of her cleavage created by her large, natural breasts stuffed into a few-sizes-too-small purple string bikini top.

"Wait until you see the pool." She wrote.

I wasn't used to seeing my sister like this, with this much skin exposed. The truth was, my Melissa was and always had been very self-conscious about her body. Whereas I had taken after our father physically, tall and athletic, my sister had taken after our mother, short and...let's say... curvy. Growing up, she had always been my chubby little sister, struggling with her weight and hiding herself under ill-fitting clothes and baggy sweats.

I'd seen my sister in a bathing suit before, on family vacations to the beach, but she always wore a basic black one piece that was sure to cover as much of her body as possible. Even then, when she wasn't in the water she typically wore a beach wrap around her waist to hide her slight belly, shapely ass, and thick thighs.

"New swim suit?" I wrote back. I wasn't sure what else to say. "Nice bazongas" seemed a little inappropriate for a brother to comment to his sister.

Besides, my sister had always been a massive nerd, with little-to-no sexual experience. I was pretty sure she was still a virgin. There's no way she meant the photo to be sexual in any way, she was way to innocent and naive for that.

Still, I couldn't help but stare at the revealing photo throughout the ride to the house-- my sister's meaty tits pressed together front and center. The more I stared, the more I could feel myself getting turned on. I squeezed my thighs together and felt a surge of pleasure pulse in my half-hard cock. Yep, I was horny all right.

But for my sister?

No way, I told myself as I finally turned my phone off. It had just been too long since I'd gotten laid, anything would turn me on, I rationalized.

"Yea." She wrote back. "You like?"

"Very nice." I said, then forced myself to put my phone away. This was getting a little too flirty.

A half hour later I got out of the car in front of my Uncle's house. It was large, way larger than our parents' house in New England, a "McMansion" on a private cul-de-sac of other McMansions. Each house only slightly different than the one next to it, each painted some gaudy shade from the same palate of pastels.

It was spring break for Melissa and I. I was a college junior in New York, and she was in her freshman year in Boston. Rather than spend the week freezing our asses off at our house, our rich uncle had been kind enough to let us know that he and his fourth wife were going on a week-long cruise and offered up his house to us for the week.

"Come get some sunshine!" He'd said in his email to Melissa and I. "Wouldn't you rather a week by the pool than the cold rain up there?"

It didn't take either of us much more convincing than that, and our parents were not only okay with it, but even offered to help us pay for airfare to get to Florida.

I took a moment to soak up the sunshine and the warm air before shouldering my bag and heading into the house. The entryway let into an airy, high-ceilinged living room where everything was white. The walls were white. The couch and furniture, white. The rug, pure white. I slipped off my shoes, dropped my bag by the door, and made my way through the white kitchen towards the back.

"Holy shit." I said to myself as I stepped through the sliding door to the secluded, fenced-in back yard to see the expansive in-ground pool. I caught sight of my sister laying there in a lounge chair soaking up the sun in her purple bikini.

"Scottie!" She said when she turned her head and saw me walking towards her.

In an instant, she got up and was skipping giddily towards me and I had stop. As she stood, I could see that her bikini bottoms were even more skimpy than the top. I tried not to gawk at the small purple triangle covering her mound, the thin string ties in bows around her wide hips.

My sister laughed and her heavy tits bounced as she skipped over to me and threw her arms around me in a big hug.

"I'm so glad to see you!" She gasped and pulled me tightly against her.

I could feel the heat of her sun-soaked body through my t-shirt and jeans, and as I naturally wrapped my arms around her waist to hug her back, I couldn't help but noticed how warm, soft, and sensual the exposed skin of her back felt against my hands. As we held each other for what felt like a full minute, I could again feel my cock throb in my pants. Unsure of what that was about, I made sure to keep my hands at the small of her back, though my mind wondered what it would feel like to take a handful of her ass.

For fuck's sake, I thought, chastising myself. Cut it out you pervert. I really needed to get laid, apparently. I wondered if I could sneak away to my guest bedroom long enough to rub one out. I needed to get some release so I could stop thinking sexual thoughts about my sister.

"Are you drinking?" I asked when I spotted what looked like a can of hard seltzer by her chair.

"Yea." She giggled. "He left us a whole fridge full of them."

"Interesting." I smirked.

"Go put your swimsuit on and join me." Melissa said as we let go of each other.

"Umm," I hesitated. "I was actually thinking about taking a nap."

"Nooooo!" My sister pleaded, taking hold of my hand as if to keep me from leaving her alone. "Come on, hang out with me. I've missed you."

"Okay," I acquiesced. "Fine." I'd have to jerk off later, maybe in the shower before dinner, I thought.

"And grab a few more drinks on your way back out!" She said after me.

I went back inside and carried my bag up to one of the guest rooms to change into my swim trunks. As I changed, I glanced out the window to find that I had a view over the backyard and the pool. Standing there naked, I found myself staring down at my sister. She was back on the lounge chair, only now she was on her stomach and I could see that her bikini bottoms were actually a thong and her entire round, shapely ass was on display.

"Wow." I heard myself say out loud.

My hand drifted down to my exposed cock and I ran my fingertips along its sensitive length. I could feel myself getting hard as I stared at my sister's ass, the thin slip of purple bathing suit outlining the tops of her cheeks and disappearing deep between them.

Cut it out. I thought and forced myself to turn away. I took several deep breaths and did my best to stuff my erection into my shorts and wedge it down between my legs.

I stalled a bit more for time by inspecting the kitchen. Typical of our uncle -- who definitely fancied himself the "cool uncle" -- the pantry was full of food and the fridge was full of alcohol. I grabbed two cans of seltzer and headed out to the back.

"That's quite the swimsuit you have there." I couldn't help but comment as I came back outside and laid my towel out on the lounger beside my sister's. "I didn't think you owned a bikini."

"I didn't." She smiled over at me. "I got it special for this week."

"I see." I said, simultaneously wanting to talk more about it but also not wanting to dig too deeply.

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"What?" Melissa said, raising up onto her elbows. "You think I look ridiculous."

"No." I was quick to say. "Not at all. It's just... well, I always figured you were too self-conscious to wear something so... revealing."

"Because I'm fat?" She said, her smile fading.

"No." I shook my head emphatically. "I've never thought that."

"It's okay, Scottie." She said matter-of-factly. "I think I've come to terms with my body."

"What does that mean?" I asked, laying down on my back on the chair and cracking the seltzer to chug half of it.

"Well, when I got to college and met my roommate Jody, it was kind of eye opening for me." She said, rolling over onto her back and shifting her bikini top around her large breasts.

"How so?" I asked.

"Jody's like me." She said.

"Smart? Thoughtful?" I asked. "Pretty?"

"Heavier." She said, her eyes meeting mine.

"Melissa," I said. "I've never thought of you as..."

"Stop." She said, holding her hand up. "It's okay, I know I'm not skinny like most other girls. I never have been, and I never will be, and that's okay. Jody, she's actually bigger than me, and she's super body positive. She's proud of her body, always showing it off and dressing sexy. Fall semester I basically wore the same sweatsuit every day while she was wearing mini skirts and tight clothes that I would never have worn."

"I see." I nodded.

"Yea, so..." She shrugged. "I guess she's kind of worn off on me. I realized I'm tired of hating my body. I should love my body. It's the only one I have."

"Well," I said, catching myself following the curve of her thighs around to where they met under the purple mound at the front of her bikini bottoms. "I think you have a great body."

"Thanks." She smiled. "Just what every girl wants to hear from their brother."

"Ha!" I said, blushing. "I'm sorry, I didn't mean...that might be the alcohol talking." I said, taking another swig of my seltzer.

"No, stop." She said, reaching over to place her hand on my forearm. "You're sweet, Scottie. You've always been sweet to me. Thank you."

We both fell silent for a while, closing our eyes and enjoying the heat of the sun on our skin. When I finished my seltzer, I sat up and tapped my sister on the knee.

"Hmm?" She opened her eyes and glanced at me.

"You need a refill?" I asked, shaking my empty can.

"Sure." She smiled. "Thanks."

I went back in and came back out to find my sister sitting up in her chair on her phone.

"Would you mind..." She asked when I came back to my chair. "Taking a photo with me?"

"Sure." I said. "You want to stand by the pool and we'll take a selfie?"

"No." She shook her head, then scooted over on her chair as if to make a little room for me. "Lay down with me."

"Uh, okay." I agreed, though I thought it seemed like an odd photo for us to take, laying down together.

I slid onto the lounger beside my sister, trying to fit. Her skin felt warm and soft against mine. It had been a while since I'd laid down beside a girl like that.

"Here." She said and scooted onto her side facing me to make more room. "Lay down."

I laid back onto the lounger and she draped her leg over mine. I felt her knee settle against my thigh, just below my cock, as her stomach and breasts pressed up against the side of my arm.

"We'll fit better if you put your arm around me." She said, lifting my arm up.

I did as instructed and lifted my arm so she could snuggle tightly against me, and I felt the weight of her breasts in her bikini against my side. She laid her head on my shoulder and I could smell her hair -- flowery shampoo and conditioner.

"Here, you take the photo." My sister said and handed me her phone.

With my free hand, I held the phone out in front of us and snapped a selfie. She gripped me tight and I could see the tops of her breasts almost spilling out of her top against my body. I couldn't help but think that it didn't look like a photo of a brother and sister, but a photo of a couple.

I handed her phone back to her and watched as she loaded it into a text message and sent it to someone.

"Who did you send it to?" I asked.

Part of me felt like I should untangle myself from this cuddle with my sister, but I actually felt quite comfortable with my arm around her as she laid against me. Every so often, she would gently slide her leg against mine and it felt nice and smooth. I let me hand around her wander down and settle onto the small of her back. I could just feel the string of her bikini bottoms atop her ass with my finger tips.

"Just sending it to Jody." She said, then quickly shut her phone off and sitting up to open her new can of seltzer.

I took this as my cue to slide off our shared chair and back over to my own. As I settled onto my stomach to sun my back, my sister's phone dinged and she eagerly checked it and giggled.

"What?" I asked curiously. "Is that your roommate?"

"Yea." Melissa nodded, typing something back.

Her phone dinged again, and again she giggled and quickly typed something back.

"What are you two saying about me?" I asked.

"Typical boy." She frowned at me. "Not everything is about you."

"Excuse me." I said sarcastically.

Of course, it seemed obvious to me that they must be talking about me. First she poses us in this close photo and sends it to her friend. Now they are firing messages back and forth at each other. Did her friend have a thing for me? I wondered. I'd never met my sister's roommate, so that would be strange if she did.

"Do you think we could..." My sister said after a few more text exchanges.

"What?" I asked.

"Take another photo." She said a little meekly. "Laying like we were before?"

"Why?" I asked, completely suspicious now.

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"Just... Please?" She begged.

"Fine." I said and got up to again join her on her chair.

I slid in beside her like we were before, only this time she laid her leg directly over my crotch. I felt the warm heat of her inner thigh press against my cock in my swim trunks and felt a little surge of pleasure.

"Uhh..." I said, freezing. "What are you doing?"

"Just let me take one photo." She said.

I watched as she set her camera up, this time not as a selfie but aimed down at our bodies, showing her leg draped possessively over mine.

"Why are you...?" I began to ask but just watched as she snapped the photo and again sent it off in a text message.

This time, I didn't go back to my chair. Instead I stayed laying there were her in my arm and her leg hugging me and watched down over her shoulder as she texted with her friend.

"OMG!" The reply came. "You ARE moving fast!"

"What the hell?" I asked.

My sister quickly hugged her phone to her breast to hide it, and glanced up at me.

"Hey!" She said. "Don't read over my shoulder."

"You're talking about me." I said. "You're moving fast? What the hell does that mean? Melissa, what's going on?"

"I can't tell you." She said. "You won't understand. It's nothing bad."

"Really?" I said, climbing out of the chair. "Because it sounds like you're talking to your friend about putting some moves on me."

"No." She whined, embarrassed. "That's not..."

"Then what are you two saying about me?" I harped, almost yelling. "I'm your brother, Melissa. Why does she think we're moving fast. Fast towards what, exactly?"

"Fine." She relented. "I'm going to tell you, but would you please not get all mad?"

"Fine." I nodded and sat back down on my chair and waited for her explanation.

"My roommate Jody and I, we made this bet." She started to explain. As my sister spoke, she looked down at the ground, as if she was afraid to look me in the eye.

"What kind of bet?" I asked.

"Not really a bet..." She said. "More like a challenge."

"A challenge?"

"To see who could fuck the hottest guy while on spring break." My sister said, still looking down away from my gaze.

"Melissa..." I started but couldn't figure out how to react. My heart was pounding and my head spinning.

Did... did my sister want to fuck me? Sure, I'd been stealing glances at her in her skimpy bikini all afternoon, but that didn't mean anything. I wasn't actually trying to have sex with my sister.

"You didn't think we were going to..." I let the rest of the sentence hang out there.

"No!" She quickly shook her head, finally meeting my eyes. "No, of course not. Gross."

"Gross?" I said with a laugh. I couldn't help it.

"No, not that you're gross." She said, blushing. "I meant, you're my brother."

"No shit." I said. "So, then what were you..."

"Jody doesn't know who you are." My sister explained. "She's never met my brother. So, for all she knows your just some hot guy I'm hanging out with all week. I thought maybe if I could send her a few, I don't know, suggestive photos, then maybe she would think..."

"That you were fucking me." I finished her thought.

"Right." She nodded. "Scottie, I'm sorry, it was stupid. I'm so embarrassed..."

"So, I qualify as a hot guy?" I asked, smirking at her.

"Objectively?" She responded. "Yea, you would be, like, the hottest guy I would ever fuck."

"Wait," I said. "I can't believe you're even talking like this."

"Talking like what?" She said defensively.

"Talking about fucking guys." I said. "You've always been so..."

"I've fucked guys, you know." She said.

"You have?" I asked. "No, wait, I don't want to know that. You're my sister."

"So what?" She said. "I'm a grown woman. I can have sex, same as you."

"Of course you are." I said. "I just didn't think..."

"What, you didn't think your chubby, nerdy sister was sexually active?" She said incredulously.

"Melissa," I said at a loss. "I don't think about you sexually at all."

"Yea right." She scoffed. "I saw you ogling my ass from the window up there." She said and glanced up at the window to my guest room.

"I wasn't..." I started to protest, but found myself going with it instead. "Well, can you blame me?" I said. "I mean, you come bouncing over to me in that skimpy little thing."

"Look," She said with a deep sigh, pulling her towel around her to cover herself up. She was getting self-conscious and I could see it. "Can we just forget about this whole thing? Forget this ever happened?"

"We could." I agreed. I could see that she was embarrassed and didn't want to talk about it any more. I couldn't blame her.

I took a big swig off my hard seltzer and laid back down on my lounger. I tried not to look at my sister, but after a while, I could see out of the corner of my that she was relaxing again. Eventually, she pulled her towel off and exposed her body in her minuscule swimsuit. I couldn't help but glance at her shapely curves.

Was she telling the truth? Had she had sex with guys? Before hearing that, I would have bet all the money I had that my sister was a virgin. That she hadn't so much as kissed a guy. But what did I know? We'd been away at school for months. I hooked up with plenty of girls my freshman year at college. Why would she be any different?

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