Toying with Hailey

My cock began responding to what my eyes were taking in, and I suddenly became glad that Hailey volunteered me to push the basket, so at least I had something in front of my crotch and my arousal was less obvious. My mind in overdrive, I tried to get my sister's body off my mind so my cock would soften and make the rest of the outing more bearable.

Hailey, on the other hand, was either completely oblivious to my stares and reactions or was conscious of it and was trying to put on a little show - I couldn't tell which. She flitted happily along out in front, leading me around the store and humming to herself for making commentary until the basket was full and we were ready to leave. Pulling my parents' credit card out of her purse, she swiped it at checkout and we were on our way home.

--

After we put the groceries away and made dinner, Hailey and I started a movie. Her choice, some flirty rom-com, played in the background and I spent half of my time paying attention to it and the other half looking at nothing in particular on my phone. When the movie was over, she stood up and I presumed she was going to bed. She turned around and faced me.

"Hey."

I raised my eyebrows at her. "Hey what?"

She had a strange look on her face, as if she was anticipating something and anxious about it. The effect was cute, and I could tell she was searching for words.

"I'll show you mine if you show me yours," she said.

"My..." I said slowly.

"Oh come on, Eric, don't be obtuse. If you show me your fleshlight, I'll show you my vibrator," Hailey said.

"What? Why? Isn't it bad enough that we both know about it?" I asked her.

"I'm just curious! I've never really seen one up close, I just want to check it out. And I'll let you look at my vibrator. Even trade?" Hailey confessed.

"So what, like right now?" I asked.

"No time like the present, baby brother," Hailey reasoned.

This was not a battle that I was going to win. But then again, I didn't think it was a battle I wanted to fight. I wanted to see hers too, I in a million lifetimes would have never had the balls to ask her about it though.

"Ok, Hails. But before we do this, don't you think it's just a little bit weird? Brother and sister playing show-and-tell with our sex toys?"

Hailey looked a little crestfallen. "I know it seems kind of weird, maybe that's why I was nervous when I asked about it... but I trust you, and I feel safe sharing this part of my life with you."

I got up and nodded at her, and headed up the stairs with her following close behind. But then I remembered something and turned around.

"Uh... I kind of forgot to clean it after the last time I used it." I told her sheepishly.

"What do you mean, wasn't that what you were doing when you were in the shower?" She asked.

I nodded, and her eyes widened. "Oh, you little horndog! You've used it again since then? When?"

Not thinking about the circumstances of how my night ended the night before, I answered, "When I laid in bed last night I couldn't sleep, I was... hard. Just decided to do it I guess."

Her face flushed and she slowly smiled. "Right after you passed my room and heard me frigging myself with my vibe?"

"Oh... yeah." I said.

"Hm! Well... grab and clean it up real quick. I still wanna see it."

"Ok."

I grabbed it and took it to the bathroom, where I started the shower water to rinse and wash the dried cum/lube mixture out of it. A few minutes later I walked out of the bathroom and into Hailey's room, and I handed it to her.

Fascinated by the fleshlight, she turned it over a few times in her hand before she unscrewed the cover, looking intently at the pussy-shaped opening.

"Wow, this thing is crazy," she said, lightly touching the silicone lips with her fingertips. "So you just stick your dick in it and go to town?"

"I lube it up first, it would be a little painful without it, but then... yeah. Pretty much." I explained to her.

She took two fingers and spread the opening, then stuck one finger inside it and felt the small stimulating nubs that lined the inside.

"Whoa... I bet that feels intense," she said, shifting her gaze from the fleshlight up to me. I think she could tell that my cock was starting to swell, focusing her eyes for a brief moment on the front of my shorts before looking at my in the face.

"It does. Not quite like the real thing, but I guess it does the trick." I said.

Hailey was quiet for a minute. She was sitting on her bed with her ankles crossing each other, I could see the fabric from the middle of her shorts pressed up against her mound, and thought I spied a tiny wet spot right where her pussy was. She put the fleshlight down on the bed beside her and leaned over to her nightstand. From where I was standing, I caught a great view of her ass while she retrieved her vibrator from the drawer. Producing it, she handed it to me.

It was sleek, with a gentle curve and about 6" long, with a tip that was shaped like a small egg. I ran my finger over the soft pink material, and found a button on the other end.

"It has 10 different settings," Hailey said. I pushed the button and the vibrator sprang to life in my hand, producing the humming sound that I heard through the bedroom door the night before.

"Wow... I didn't expect the vibration to be so strong," I said to her.

"Oh, that's not even the strongest one," Hailey said. She took it from me and pressed the button at the end a few times before handing it back to me. This time the humming was even louder and had a higher pitch.

"Damn!" Taking me by surprise again. This thing had a strong motor!

She took it once again and pushed the button twice more, and gave it back. This time the vibration was lighter, but had an on/off pattern that vibrated at different intervals.

"That's my favorite setting. Sometimes i just use it on my clitoris, like last night, but other times I'll put it inside me up against my g-spot." Seeing the look on my face, she reddened and said, "Sorry... probably TMI, right?"

I was speechless. Not only did my big sister show me her vibrator, she explained how she used it and her favorite setting! I was entranced by what I heard and not really paying attention, and so it surprised me when I felt the vibrating sensation up against my cock through my shorts.

"Hey!!" I said, jumping away.

"Sorry!" Hailey said. "I thought you would want to see what it felt like."

"No, that's ok, I'm not mad... I just didn't expect it right then and it caught me off-guard."

"Oh!" She said, smiling at me. She switched it off and put the vibrator back in her drawer. When she sat back up straight, she stretched her arms over her head, pulling my eyes to view her breasts. Sometime between getting home and that moment, she had taken her bra off again. She caught me staring this time.

"Like what you see there, little bro? I can't stand bras, plus my boobs are too small anyway, I don't even need to wear one."

Stumbling over my words, I said, "I don't think they're too small... they fit you just perfectly."

"Aw, thanks!" Hailey said, standing up and getting up on her tiptoes in front of me, laying a little peck on the tip of my nose. "You're so sweet."

"I'm telling the truth, Hails. You have a great body, there's not a single thing wrong with it." I said.

She smiled at me and stepped backward.

"Thanks, really Eric. It feels really nice to be told that sometimes, I know that sounds superficial but it's the truth."

"I love you, Hailey."

"I love you, too, Eric. Thanks for not thinking I'm a weirdo."

I laughed and said, "Oh no, I totally think you're a weirdo, but that's just because I know you! Alright, I'm turning in for the night."

Hailey laid on her bed, and said, "Me too, I'm beat. Sweet dreams, baby brother! Oh... and now that you know where I keep it, if you ever want to use my vibrator, just come get it. Just don't run the batteries dead or I'll find you and kick your ass!", smiling and winking at me.

I picked up the fleshlight from her bed and said, "Ok... I'll keep that in mind."

Mind racing, dick hard as a rock, I left her room and made a beeline for the drawer where I kept the lubrication, got the fleshlight ready and plunged completely into it. Less than a minute later I was cumming powerful ropes into it, having been continuously stimulated all day long. Collapsing into my bed, the last thing I remember before drifting off to sleep was dull humming noise drifting through the shared wall between mine and my big sister's bedroom...

--

I woke up the next morning in a euphoric state, it was one of those mornings when you wake up well rested, but perfectly content to stay in bed as long as you can! Next to me on the bed was my fleshlight, and I was naked underneath my warm covers. I listened for any sounds telling me that Hailey might be awake, and hearing none, assumed she was still sound asleep.

Laying there, I picked my phone up and opened the Lock Screen, to find a single text message, sent from Hailey. It was sent at 1:00 in the morning, not long after I fell asleep.

-I know you did the same thing I did whenever you went to bed last night... next time can I watch?

There it was. All of a sudden my heart was pounding out of my chest, my hands were sweating, and my mind raced. I thought about my sister, how sexy she was, and how bad I wanted to fuck her, to finally see in real life what I had been dreaming about.

I also thought about how good she was. How we had always been there for each other growing up, and how I genuinely loved her. I knew she felt the same way. I didn't want to cross a line that we couldn't later uncross, and it damage our relationship. We'd been a team, leaned on each other, and were real friends.

But a real, physical, romantic relationship seemed like the next natural step for us. The caveat being that we were siblings, every other part about how things were progressing between us was normal. I decided then and there to go for it. I picked my phone back up and looked at her words one more time, then sat it back down. I'd talk to her later, face to face about it.

--

An hour later, I was sitting in the living room with the TV on when I heard a door open upstairs and footsteps coming down the stairs. I looked up and saw my big sister, coming down the stairs wearing only a short t-shirt and red panties. I took a sip of my coffee, tasting the dark roast but drinking in the sight before me, Hailey still half asleep, bed head hair, and a little grin when she saw me. I stood up as she walked up to me, and bent down to kiss her forehead and wrap her up in a hug. She pressed into me, and I felt her breasts squeeze up against me and her hips pushing toward mine.

"Good morning Medusa, how many kills did you get last night?" I said, teasing her about her wild hair.

"Shut up," Hailey mumbled into my shoulder, then looking up at me with a sideways smile.

My arms around her waist, my hands found bare skin above her panties and below her shirt, and felt her soft skin with my fingertips. I resisted the almost overwhelming urge to cup her ass cheeks with my hands. I released her and she stretched and yawned. Rubbing her eyes, she asked, "How did you sleep?"

"Like a baby," I replied to her. She reached down to the end table where I sat my coffee cup, picked it up and took a sip, making a sour face.

"God, how can you drink this stuff black? Ever heard of cream and sugar?"

I laughed at her expression. "Nah, it makes me tough, I like it like that."

She smirked and sat down next to me on the couch, pushing her legs up against mine and leaning her head on my shoulder. She picked up her phone and opened it, acting like she was doing nothing but I did notice her open the message app to see if she'd received a reply to her late night request. Nope, not yet. I'm going to have a little fun with this and tease her.

"This is nice," she said after a little while.

"Hm?" I said, not really paying attention to anything in particular.

She looked at me. "This. Cuddling with you, you're warm and it feels good."

I agreed with her. "You know, you're right. It does feel nice."

She lay there on the couch against me for another half hour, her breast pushed up against my chest, and her head resting on my shoulder. She yawned and then slowly sat upright.

"Ugh, if I don't get up now, I won't ever get up and do anything today," she said. "Plus, I need to shower and brush my teeth. Morning breath, yuck," as she stuck her hand up to her mouth.

"Oh thank the lord, please do that. I swear I was about to suffocate from that gnarly dragon breath you've got going on," I told her.

This earned a smack on the arm and a little sass in return.

"Well then, maybe I'll just kill you with it!" She said, leaning over and trying to breathe in my face. I pushed her away and she stood up, laughing. While cuddling with me on the couch, her panties had ridden up and were wedged in between her delicious looking ass cheeks. I got a great view as she reached back and straightened them out, before heading toward the stairs.

"I'm going to shower. Will you make me some coffee so I don't have to drink that swill you have?"

"Yes ma'am," I said, giving her a salute.

"That's what I thought," she said, disappearing up the stairs, her tight ass bouncing as she climbed each step.

I went into the kitchen and got her coffee, then brought it back into the living room and sat it on the table next to mine. Then I took out my phone, went back to her message and read it again, making sure I wasn't dreaming earlier when I read it while still in bed. I sent a one-word reply:

-Yes.

A little while later, Hailey came back down stairs. Wearing a tank top and some old cheer shorts from high school, she took her coffee and sat back down assuming her position from earlier, tucked under my arm and cuddled against my side, half-interested in what I was watching on TV. My heart began to beat a little faster when I saw her absentmindedly pick up her phone and open it. I looked past her breasts down at the phone screen as she opened the messages and tapped on my name. Reading my reply, I felt her tense up by my side and her breaths quickening. She slowly sat up turned toward me.

Her voice quiet and almost trembling, she said, "I was so nervous about how you were going to answer that."

I smiled at her reassuringly. "Well don't be. I love you and I trust you, and I know you feel the same way."

Hailey, emboldened by my reply, sat across my lap.

"So when do you want to do it?"

"Well, dear sister, as you say there's no time like the present!"

Squealing with excitement, she hugged me, and kissed me full on the lips. Surprised, it took me a second to return it, and by the time I did she was getting up from my lap.

"Ok. I'll be in your room in a few minutes if you want to go get ready."

Heart pounding, I stood up from the couch and followed Hailey up the stairs. By the time I got to the top landing, she was disappearing in her room. I went into mine and pulled the door closed, then sat on my bed and pulled out my fleshlight. I ran to the bathroom to rinse it out, and was back sitting on my bed when I heard Hailey's door open. She knocked softly on my door.

"Come in," I said to the door.

When the door opened, I was greeted by the sight of my big sister, who had changed into a pale pink panty and bra set with a satin finish. Her sun-kissed body was complimented by her underwear, and my cock immediately responded upon seeing her.

"Well, what do you think?" She asked me, spinning around to reveal that the panties she was wearing was a thong, splitting her ass cheeks. Between her legs from the back, I could see her pussy lips printing on the thin material.

"Wow..." was all I could muster. Then I noticed her hands. She was holding her vibrator. When I saw it, I raised my eyebrow, and seeing the expression on my face, she smiled and said, "Even trade, right? I get to watch you and you can watch me?"

I swallowed hard, my mind spinning so quickly that I had a hard time finding words. I enthusiastically nodded my agreement, and my sister joined me on the bed, hips touching. She looked down at my crotch, my hard cock still covered by my shorts. A faint smile formed on her perfect lips, and she leaned over to kiss me.

"Any time you're ready, baby brother."

I slowly stood and faced her. Looking down at her, she bit her lower lip and reached behind her back, unhooking her bra and letting it slide slowly away from her breasts, revealing them to me for the first time. The small mounds were perky, with perfectly shaped nipples, which were hard with excitement and anticipation. She was a work of art.

"Just in case you needed a little motivation," she said in a low, almost husky voice. She parted her legs slightly, and I saw the damp spot on her panties.

Hands trembling just a bit, I fumbled around until I found the waistband of my shorts. I slowly lowered them, allowing my cock to spring free from its restraint. Hailey's eyes, transfixed to it, suddenly widened. Her breath catching, her breasts heaved with each inhale and exhale and she looked up at my eyes expectantly.

I picked up the fleshlight and my bottle of lubrication, applying some to the silicone lips and a good amount to my cock. Standing about a foot from her, I held the tip of my cock to the pink entrance and looked her in the eyes as I slowly plunged all the way to the hilt. Withdrawing slowly with a small twist to distribute the lube evenly, Hailey licked her lips and we both let out a simultaneous moan.

I picked up a little speed, making full thrusts in and out, and Hailey raised a hand to her breast and grabbed it, pinching her nipple and moaning again. With her other hand, she picked up her vibrator which had been laying on the bed next to her and laid back a bit, switching it on and placing it on top of her panties, up against her clit. Her breathing sharpened and her moans became more pronounced, as she drew small circles around her clit with the tip of the vibrator, the damp spot on her panties growing larger.

I was mesmerized by the sight, and began stroking myself harder. I heard Hailey clear her throat and my gaze went from her panty-clad pussy to her face.

"Can- can I hold it for you while you thrust into it?" She asked tentatively.

"Yeah, you can... I'm not going to last much longer Hails," I said.

"Me neither," she said breathlessly, and sat up on the bed. I moved close to her and she took hold of the case, holding it steady. I adjusted my stance and resumed my thrusting. She held it still for a moment, then began twisting it slightly, matching my movements in and out.

"Hang on," she said. I grabbed the fleshlight from her and she reached down with both hands to the waistband of her panties. Lifting her hips, she slid them all the way down her legs in a single motion. Her bare slit was glistening with her juices, her outer lips tight and the tiny nub of her engorged clitoris sticking out and begging for attention. She took her vibrator and slid it into the folds of her vagina, then took the fleshlight and pressed the end of it to the vibrator.

I got on my knees in front of her and entered the toy, feeling the new sensation the vibrator added to it. My sisters knees resting on my hips, I resumed my thrusting. After a minute, I felt her muscles tense up, and she threw her head back, shuddering and moaning as she came, her orgasm crashing through her body and causing her legs to twitch. The sensation was enough to put me over the edge.

"I'm about to cum," I told her.

"Come on my tits, brother!" Hailey said, with lustful, pleading eyes.

I immediately withdrew my cock from the fleshlight and stroked it a few more times with my hand, my sister moving her breasts closer to me. Cum erupted from the tip of my cock and hit my sister directly between her boobs, followed by more spurts that soaked her entire chest, and finally dripping down and pooling in her cute belly button.