Cancun Candids Ch. 03

The walk back to the hotel room was a long and silent one. A million thoughts were running through my head, but I couldn't bring myself to say a word to Jennifer. That was... insane. My sister had just gotten off on the beach. More specifically, I had kind of helped get my sister off on the beach! Sure, I hadn't been the one fingering her ass, (she'd taken care of that on her own!) but my fingers had been right there alongside hers. It had all been so wet and slippery... I couldn't stop thinking about the heat and the slickness emanating from my little sister's pussy.

FUCK! I had been so close to putting my fingers inside her! I'd been rubbing all over her ass, why hadn't I slipped my fingers inside her vagina? We had clearly been past the point of no return. That had probably been my one chance. My one chance to fingerbang my sister... Man, what a wild vacation.

Jennifer and I basically walked side-by-side the whole way back. I don't think either of us could summon the courage to look at one another, so we just stared straight ahead and didn't say a word. Soon enough we arrived at our hotel room door. Jennifer pulled a key card from the pocket of her capri pants and slid it into the slot. The little light flashed green, and she opened the door. I moved to follow her inside, but Jennifer stopped in the doorway and turned to me.

Looking me squarely in the eyes, Jennifer said, "Dave, do you think you could... uh... give me a little bit?"

Not sure what to say, I stared right back into her hazel eyes, a little dumbfounded.

"That was just... intense, you know? I just think... well, I don't know what I think. But do you think you can, like, walk around for a bit? Or go for a swim or something? I just want to be by myself for a little."

I have to admit, I was a slightly crestfallen, but I understood. "Of course," I heard myself say in a surprisingly clear voice. "Totally makes sense. I'll just... come back in a little while."

"Thanks," said Jennifer softly, with a grateful smile on her lips, "I really appreciate that." I turned to go, and before I'd traveled two steps I heard her say, "Oh, can you, uh, leave your camera, please?" I looked down at my hand, still holding my digital camera. I contemplated what it meant, handing it over. All those photos... it was a goldmine of explicit material. I'd already imagined countless jerkoff sessions using them as inspiration. But I didn't really have a choice. I handed Jennifer the camera, just saying, "Yeah, sure. Of course." She smiled softly and quietly said, "Thanks." I turned to leave a second time, and Jenn added, "And thanks for taking the pictures..."

I turned back over my shoulder and saw Jenn still standing in the doorway, her smile just a little bit warmer on her face. She still looked pensive, and certainly a little confused, but I was relieved I didn't see much anger or fear on her face. Not knowing what else to say, I said softly, "Sure. It's what brothers are for, right?" I honestly didn't know why that's what came out of my mouth. I didn't exactly mean anything by it. But Jennifer absorbed it with that same half-rueful smile and just said, "Right." And she closed the door.

I stared at the door to the hotel room for a minute. It was my room too. I had a key card. I could certainly force my way in there and damn the consequences. But that didn't seem like the right move at the moment. I wandered around the central area of the resort for a little while, passing by the pool, the bocce courts, and the jet ski rental shack. I echoed Jennifer's rueful smile as I thought back to a few days prior when she'd suggested we rent a couple of jet skis together and try them out. I didn't think that was likely anymore...

I continued to wander, just letting my feet move while visions of my sister danced through my head. That ass... those tits... that smile as she watched me drinking in her naked body. We'd had fun, hadn't we? Joking and role playing as if I was her boyfriend taking naughty pictures of her. I mean, it hadn't been against her will. (Well, not the second round of photos. Those first ones while she was asleep... that was on me.) I don't know. I wasn't sure what to think or how to feel. And I certainly wasn't sure about anything that was going on in Jenn's head.

Would she tell Mom and Dad? Would she ask them for her own room for the last few nights of the trip? "Mom, Dad, Dave's a perv and has been taking naked pictures of me, I can't sleep in the same room as him..." I don't know, it seemed unlikely, but no more unlikely than the idea of my sister posing nude for me on a beach. Anything seemed possible at this point.

I'd made it out to the beach and I sat down, staring out at the waves. I wasn't really seeing anything, I was still just picturing all the forbidden skin I'd witnessed Jennifer exposing to me. That suit. That fucking bathing suit! That beautiful, tiny, hot, red bathing suit from Le Mirage. What a beautiful stroke of luck that had been when Jennifer got up the courage to not only buy it, but then wear it. I never would have expected that of my sister. I guess there was still a lot I had to learn about her. If she ever talked to me again...

I looked down at my watch and realized it had been about an hour since I left Jenn at our room. Could I go back now? I had no idea what kind of time she needed. The rest of the afternoon? Or was she okay now? I hesitated for a moment, then realized I would just be torturing myself if I waited or wavered. She hadn't been specific about time. And you know what? If she was pissed at me, or uncomfortable around me, so be it. That was that, and me waiting to find out wasn't going to solve anything.

I hopped up and started back towards our room. After my contemplation, I was able to actually take in my surroundings a bit more, noticing once again all the skin being flaunted and all the skimpy bathing suits. I saw two girls walking from the pool area to the beach in what could have possibly been bathing suits from Le Mirage. One was a brunette wearing a small black thong, and the other was a blonde in an almost matching white thong. Jesus... did girls like that know what they did to a guy like me?

Of course they did.

I didn't stop walking, but I did blatantly keep my eyes glued to their asses as they headed down to the water. I loved seeing their strong, toned butts walking side by side across the beach. They looked so nice it almost made me stop thinking about Jennifer's toned ass. Almost.

I rounded a building and was back at our hotel room door. I thought about knocking, but my attitude had kind of shifted after seeing those hot female bodies on the beach. I was now in more of a "fuck it" kind of attitude. Like I said, this was my room too. I pulled out my key card, slid it in and out, and when the little light turned green I opened the door and walked into the room.

The blast of the AC was intense after so long outside in the hot tropical weather. The door slammed heavily closed behind me, and I saw Jennifer sitting at the desk behind my computer again. A little bit of déjà vu back to this morning, when all this madness had begun. I suddenly lost a bit of my edge, and my "fuck it" attitude disappeared almost completely. Man, my sister was gorgeous. She'd changed out of her t-shirt and capri pants and was instead wearing a flower-print summer dress. It was one I'd seen on her dozens of times before, but I'd never quite focused on all the clingy bits the way I was now. Maybe she'd showered? I don't know. She looked fresh, compared to the hot and sweaty state I was in.

Jenn looked at me, not surprised, but still with her eyebrows raised slightly. Had I come back too soon? I walking into the room and stopped a few feet away from her.

"Hey," I said."

"Hey," she answered.

"Umm... did you get enough time? I mean, was I gone long enough?"

"Yeah," she said. "I think I'm good now. Like I said, it was just... intense, you know? I wanted a little time."

"I totally get it," I said reassuringly. "Totally makes sense."

"Yeah."

I stood there awkwardly for a few moments, only half looking at my sister sitting at the desk. She seemed calm, at least, but the vibe in the room was certainly not comfortable. She was just looking at me, but I couldn't discern anything from the look on her face. I decided we should just talk. We had to figure this out. We were siblings, after all. Nothing was going to change that. I took a few steps over to my bed, which was opposite the desk in the room, where my sister sat. I sat on the foot of the bed, facing my sister. Now just the desk, with my open laptop upon it, stood between us.

My sister didn't seem to object to my coming closer and settling in, but she also still didn't say a word. Well, I wasn't going to just let things hang in the air. I said, "So... how are you feeling?" It seemed like a decently open-ended question, but I figured it was obvious what I meant. How was she feeling about what had happened... between us.

"I'm okay." She said. "I took a shower, which felt really nice. I got all that sand off of me."

Honestly, I hadn't even thought about that. She'd been covered in sand in so many places... She'd scooped it all over her crotch, her ass cheeks had been caked, there'd probably been some sand involved at the end when... when she...

"Oh yeah, how's your ass?" I blurted out.

Ugh. That was probably not my best move...

But Jenn just sort of smiled awkwardly. "My ass?" She said with an awkward scrunch of her face. "You mean my butthole? Which I decided to stick a finger into on the beach, with sand all over everything, and nowhere near enough lube?"

I kept silent and looked at her. She didn't seem mad. But she also wasn't as playful as she'd been when we had talked about her intimate body parts before. (I couldn't help but long for the coy smile on her face the first time she had said, "You mean my breasts, and my nipples...") But I guess I just had to read her mood now. So I said, "Yeah. How's your, uh, butthole? Is it feeling okay? You were in a lot of pain out there on the beach, before we..."

Jenn scoffed a little and rolled her eyes. "Yeah, Dave, my butthole is fine now. Once I showered and got all that sand off of me it felt much better." She paused, a small silence hanging in the air. Then quietly, "But thank you for asking."

"Sure," I answered automatically. "Just wanted to make sure you were okay."

I had almost added, "with everything we did" to the end of my sentence, but I didn't. I guess I was still too timid to hear the answer to that question. I looked up at Jenn, our eyes meeting, and that silence hung in the air again. It stretched on longer and longer. Jenn twisted the desk chair side to side, maybe a little uncomfortable, but maybe not... Finally she spoke.

"Jesus, I can't believe we did that."

"Did what?" I asked, stupidly.

"Where do you even want to start, Dave!?" Jenn exclaimed, exasperated. "I mean, I don't know. Maybe you taking naked pictures of me while I was asleep? Maybe me not freaking out the first time I saw them? Maybe me even suggesting that you take more. And then it just went so far! It was crazy enough that you were looking at my naked body and taking pictures of it, but then... you know, the whole ass thing."

"Yeah, the whole ass thing..." I repeated, and trailed off.

"Yeah," said Jenn, as if she was annoyed I didn't have any more to add. "Yeah, the whole ass thing, where I put my finger up my butt in front of my brother."

"You did a little bit more than that," I said without thinking. (Man, I really had to keep my mouth shut.)

"Yeah, okay, you're right," Jenn almost shouted. "Yeah, I did more than that. First I put my finger up my ass, with my brother watching and photographing it, then when my finger got stuck, my big brother spit onto my asshole to lube it up, and then proceeded to rub his fingers all over my sphincter until I... until I..."

She ran out of steam. So I picked up for her. "Yeah," I said softly, "What happened there at the end? It looked like things got wet enough to pull your finger out, but then you..." I trailed off again.

"I... I..." Jenn sighed. "I mean, it did. It was wet enough to get out. And I started sliding it out, and..."

"And what?" I prompted.

"And... and it felt really good, Dave. Okay? I mean, I'm sorry, but I happen to be a girl who likes anal play. And, I mean, I was already pretty horny from all the stuff before... the whole photoshoot and everything, and the role playing, and so when my finger started sliding out of my ass, and you were... you know, you were rubbing on my ass with your fingers too, and it all just felt good. So I wanted more, in the moment, you know? I wanted..." she sighed again, frustrated. "I wanted to feel something filling my ass, and I wanted to get off. So I fingered my butt while you rubbed me and I got off. There. I said it. Happy?"

The silence was back. I looked at my sister in disbelief. It was crazy to hear her say it all.

"I... I wasn't sure that was what happened, Jenn. Sorry."

"Sorry?" She said. "Why sorry? I mean... I got off. What's to be sorry about?"

"I don't know," I said. "I mean, you seem... upset. So I'm sorry."

"Well, I'm just... I mean, you know. I don't know how to feel."

"Yeah, I get that." I said. "I totally get that. I'm glad that you, uh, got to feel good for a while though. I'm glad you got that release."

"Yeah," she laughed. "I guess that's true. Obviously it was nice while it was happening."

"It, um... it feels that nice, though?"

"What?" Jenn asked.

"The, uh... with your finger in your ass?"

That persistent silence returned, but only briefly. And it didn't necessarily feel awkward this time around.

"I mean, yeah," answered Jenn. "I told you, I happen to like that. So, yeah."

"What's it feel like?" I asked, genuinely curious.

"What, putting your finger up your own butt?" Jenn said with a smile.

"No! I just mean... anything. What's it feel like doing anal? Or any kind of butt stuff?"

"Well, it just feels really good." Said Jenn, contemplating her answer. "I mean, there's a ton of nerve endings in your rear, so it can be really pleasurable under the right circumstances. Like, you know how there's the most nerve endings under the head of your penis?"

"Uh, yeah, I know that." I said, surprised that this was turning into a sex ed conversation, and that my sister was mentioning my penis.

"Right. So just like it feels really good when someone is licking or squeezing that part of your penis, it can feel really good when someone is rubbing or fingering your ass. And then it's a whole different sensation when something fills your ass. Like a finger, a toy, or a dick. When that happens, then you've got all the nerve sensations going on, and you feel like you're being filled. And then obviously you've got the naughty aspect of it as well. Come on, haven't you ever tried it?"

"No," I said, the disappointment probably clear in my voice. "I've never been with a girl who was into that."

"Oh," said Jenn. "That's okay. Maybe someday you will. And you've never had anyone do that to you either?"

"What?! No!" I said, surprised at the suggestion.

"Hey, don't act so surprised! I mean, tons of guys these days are into some ass play. And the prostate is a whole different story. I mean, John is definitely into it. He wants me to play with his as often as he wants to play with mine."

"And you... do? You do that to him?"

Jenn sighed. I had a feeling she hadn't expected the conversation to really go this way. "Yeah," she said. "It's fun. It's nice. I mean, everything has to be clean, obviously. But it's fun to play with him down there. Sometimes I just rub over his back door when I know he's close to finishing and it puts him over the edge. Other times he'll want me to actually finger him so we'll get some coconut oil involved and I'll try and make him shoot by hitting his prostate. It's fun doing that. I mean, you did it to me. Wasn't it fun?"

I didn't know how to respond. I just looked at her.

"Okay, so maybe that's the wrong word for our situation. But what did it feel like? Obviously it felt great for me. What did it feel like for you while you were rubbing... uh, rubbing me down there?"

I paused to think, and then I just answered honestly. "Well, I wasn't really focused on how it felt in the moment. I mean, I was just concerned about helping you get your... uh, get out of the situation you were in. So that was my main focus." Jenn just looked at me, obviously not interested in letting that be my answer. "But..." I said, searching, "But, yeah, it was... fun. It was definitely fun. Yeah, I mean, like I said, no one's ever let me do anything like that before. So it was, um, crazy. But fun."

"Yeah, it was crazy," said Jenn, looking at me with her imperceptible smile.

"Yeah, it felt nice. Now that I'm thinking about it, I could feel the... I mean, I could feel the texture of the skin around your, uh, sphincter. Like, you know, your asshole."

"Yes, I know." Said Jenn.

"Yeah, like, it definitely felt different. Like, that was a cool part of it. It didn't feel like any other part of a girl's body. Like, I know how soft a pussy can feel, on the outside and on the inside. I mean, it's not just an intimate spot. It really does have its very own sort of... texture. Like, you know you're touching a pussy. I guess it was the same way with your asshole. It was a little stretched, I guess, around your finger, but there were such distinct differences between, like, the skin of your upper thigh, and then the skin of your ass cheek, then the little wrinkles of your butthole, and then even that little spot between your butthole and your pussy. Like, even that had its own unique feeling to it."

"Wow," said Jenn under her breath. "I guess my memory is foggy. I didn't realize you had... touched all those parts of my body."

"Oh, no, I don't think I did!" I said reassuringly. "I really don't think I did. I was just using that as an example. Like from other girls I've touched. Their legs, their asses, their pussies. Like, just thinking of the different textures. Yours is the first ass I've touched. Well, asshole I guess." Jenn nodded a little, understanding. I barreled on, not really knowing why. "See, honestly, a lot of sex is about texture to me. Like, I love even just seeing different parts of a woman's body, because I can imagine what that body part's unique feeling and texture is. So even when I'm just watching porn, I'm seeing those things and imagining what they actually feel like in real life. I mean, that's why I like looking at pictures of... you know, of breaded pussies and stuff." Jenn snorted a soft laugh. "No seriously! Because in the pictures I can see that whole texture! I know what a soft pussy feels like, but I don't know what it feels like to cup a pussy in my hand that's coated in sand. Same thing with an ass cheek. A nice ass cheek is so soft and full in my hand, but what does it feel like with all that sand caked on it? And to take it a step further, what does that pussy feel like around my dick as I slide in and out while the lips are covered in sand? Just like the difference between a pussy that's shaved smooth versus a pussy with a nice, groomed bush. I'm mesmerized by all those different textures."

"Huh." Said Jenn, sounding curious. "So you were thinking about all those things while you were looking at me? You were thinking about what my pussy felt like covered in sand? Or what it would feel like to cup my ass after I sat down in the sand?"

She didn't say the final one, but I sort of said it in my head anyway -- or what your breaded pussy would feel like as my dick slid in and out of it...

"Umm..." I said, genuinely unsure of what to say. "I mean, I don't know..."