Toying with Hailey

I dropped my keys on the kitchen counter as soon as I got into the house, and made a mad dash for my room. I'd been thinking about it all day and I was horny beyond belief. Closing the door behind me, I stripped my shirt off and threw it on the floor, unbuckled my pants and in one move, pushed them and my boxers down to the floor. My cock was already hard, in anticipation for a release, a bead of pre-cum running down the underside of my shaft.

Digging around in my top drawer, I found what I was looking for. I took the hard black case out of the shirt I'd wrapped it in, and unscrewed the end, revealing a silicone pussy. After soaking the entrance with lube, I plunged my cock deeply into the sleeve, groaning loudly with satisfaction and pleasure. After holding still for a moment, I began to stroke my cock with it, long, full and slow strokes, savoring every rib and nub inside the toy. Having built myself up all day, I knew I wouldn't last long, so I relished the stimulation.

My balls began to tighten, and so I pumped furiously into the silicone, until my muscles tensed and my mind went blank. My cock fully enveloped inside my fleshlight, I dumped a large load of cum deep into it, moaning loudly and feeling the intense pleasure of release. I fell back onto my bed, my now softening prick still completely tucked into the soft silicone, finally relaxing. I had almost fallen asleep until I felt cum leaking out around my cock and running down my balls.

I stood up and reached for the t-shirt that had previously been used to conceal the fleshlight and used it to wipe the cum dripping off of me, then I slipped on a pair of basketball shorts and headed for the shower. My folks weren't home yet, so I knew I had some time to clean the toy and myself. I got in the shower and lathered up, then rinsed and cleaned the inside of the silicone sleeve, making sure all of my cum was washed out and down the shower drain.

After my shower, I walked back down the hallway to my bedroom, holding the fleshlight in one hand and the front of my towel with the other. I was almost to my bedroom when the door next to mine swung open wide, scaring the shit out of me.

"FUCK!" I yelled, dropping the fleshlight on the ground and loosing grip on the towel, barely catching it before it fell all the way to the floor.

"Hey Eric! I- oh... sorry," my sister Hailey said. Realizing my state of undress, she turned to go back to her bedroom, but not before looking at what caused the thud on the ground and saw the fleshlight, which by now had rolled away from me and was heading down the hall, threatening to reach the stairs and fall to the ground floor.

Damn, I was caught. Dead to rights. Swearing again, I ran after it and picked it up, then beelined to my room and slammed the door without another word to Hailey. The embarrassment could have killed me right then and there, my heart was pounding and I could feel my face flushing red. I got dressed and hid the toy in its designated spot, and not knowing what else to do I flopped down on the bed and started scrolling through my phone in a poor attempt to distract myself from my shame at being caught.

A soft knock at my door pulled me out of the trance I was in. "Yeah?"

The door opened slowly, and I heard Hailey's voice, "Hey Eric, are you decent?"

"Yeah, come on in," I said apprehensively. I had zero desire to have the conversation I was about to have with my older sister, but in the moment I figured I might as well get it done. Hailey came into my room and sat in the chair by my desk. I sat up in bed and faced her.

"I didn't know you were here," I said to Hailey.

"I finished finals yesterday, so I packed up last night and headed home this morning for the summer," Hailey explained. She was a sophomore at the state college a few hours away, studying marketing. She continued,

"I got home about an hour before you did. You didn't see my car parked out front?"

"No, I was...distracted," I mumbled back to her, the embarrassment beginning to rise once again in my face.

"Oh..." her voice trailed off. I looked up at her and saw that she was showing a little embarrassment as well.

"Anyways, sorry. I didn't mean for you to see that."

"And hear, too," Hailey said.

Oh, great. My older sister not only saw me walking down the hallway with a pocket pussy, she got to hear me moaning as I pumped my cum into it. She must think I'm a real winner...

"Yeah. Sorry about that too, I guess," I said, looking away from her and out the window, desperately begging for this torture to end already.

"Look... it's ok, it really is," Hailey finally said. "People jack off, it's not a huge deal."

"Yeah, and how many people do you know have a sex toy for that specific purpose?" I almost spat at her. It was embarrassing enough for me to have gone into the adult store and buy it off the shelf, and that was a total stranger I was dealing with when I bought it, and now my sister, who I've known my entire life, knows.

"Well...more than you might think," Hailey said. "I have a toy I use too."

Why is she telling me this? Is she trying to make me feel better about it?

"Well, thanks for the over share, there sis," I scoffed, getting a small chuckle from her and realizing that I had a slight smile as well.

"Anyways... don't worry about it. I'm not going to tell mom and dad, they'd probably try and put you in therapy, knowing them," Hailey said. Our ultra conservative parents would never have approved of anything sexual, and actively stayed away from the subject. I didn't even get 'the talk' from my dad.

"Thanks," I told Hailey. At least my secret would stop with her.

"Are we good, Eric?"

"Yeah, we're good."

--

Later on that night, I was feeling relieved that Hailey had appeared to drop the subject and kept true to her word that she wouldn't say anything. Filling us in on how school was going for her, my parents were happy she had come home that day, not the next week as she had originally planned. With the exception of our initial reunion, I was happy to have her home as well. Despite being two years apart, Hailey and I never really bickered back and forth like typical siblings. We had a great relationship and usually talked to each other about things going on in our lives before we considered talking to our parents about it. With how strict they were about most things, it was easier not to have to deal with the judgment from our folks.

"I have an announcement to make," my dad said as dinner was winding down.

"Your mother and I are going to St. Louis for three weeks. I have to oversee our new branch startup, and your mom decided to go with me. Do you two think you can get along for by yourselves without burning the house down?"

After we gave assurances we would be ok by ourselves, Hailey and I cleaned up the kitchen after dinner.

"So what are your plans for the summer?" I asked Hailey casually.

"I'll pretty much be here most of the summer. I have a remote internship with an advertising firm, but I have a project I'll be working on from home, then I'll go to the firm for two days right before the fall semester starts. What about you?"

"Not much, really. I just quit the job I had and I'm going to try and relax before I go to school this fall." Having just graduated high school, I was planning on spending this summer doing as a little as possible, one last break before college. In the fall, I would be going to community college for a year and then transferring to the same university Hailey was attending, with plans to study business.

"Good! It'll be fun to spend time with my precious little baby brother!" Hailey chided me, smiling when I returned her comment with a light slap and rolling my eyes.

After the kitchen was cleaned, we sat on the couch and watched tv while our parents packed their bags. I noticed her looking at me a few times but never thought anything of it. Finally after a few yawns, she stood up and said, "Alright baby bro, I'm hitting the sack. It's been a long day today," and gave me a kiss on the cheek. "It's good to be home."

"Alright, good night Hailey. I'm glad you're home too," I replied to her.

Not long after Hailey went upstairs, I felt fatigue begin to wash over me as well. With nothing else to do, I decided to go to bed myself. When I got upstairs, I went towards the bathroom and while passing by Hailey's door, thought I heard a sound from inside her room. Paying no mind to it, I continued to the bathroom and got ready for bed.

After taking a piss and brushing my teeth, I walked toward by room. Passing Hailey's door, I heard the sound again. It sounded like a dull hum was coming from her room. Curious, I stopped outside her door and listened, trying to figure out what the source of the humming noise was. I hadn't been there for more than a few seconds when a second noise drifted through the thin door: an unmistakable moan of pleasure that I knew came from Hailey.

Quickly putting all the pieces together, I realized what I was hearing! My older sister was on the other side of the door, using a vibrator on herself, and from the sound of it was approaching her climax. Her moan was accompanied shortly after by a few short gasps, building up her pleasure. I was about to continue on to my room when I heard a sharp breath come from her, followed by, "Oh god Eric, yessssss!" And the sound of her moving around her bed, the headboard gently tapping the wall as she rode the waves of her orgasm crashing through her body.

On the other side of the door, I stood frozen, not believing what I'd just heard. My older sister was having a jill session, and said my name as she came!

Suddenly I heard steps on the other side of the door. Startled and not wanting to get caught, I rushed to my door and went inside my room, but my door swung too hard as it shut and made a loud noise. It couldn't have been more apparent that I was just in the hallway. I heard Hailey open her door, then quietly shut it again, then silence.

Lying in my own bed, I was trying to process what just happened. I began to build a vision in my brain of what was going on on the other side of the door based on what I heard. Hailey, laying naked in her bed, teasing her clitoris with her vibrator, writhing around in response to the stimulation. Arching her back, pushing her breasts into the air and plunging her fingers into her pussy with one hand while circling her clit with the vibrator. Bringing herself to her climax, and shuddering as her orgasm came to her while thinking about me.

The visual caused my cock to begin to stir under my blanket. Hailey, 7 inches shorter than I was, had a sleek, feminine body that was shaped by her love for running and yoga. Her toned legs went up to a perfect tight ass, and she had a flat tummy, with small, perky B-cup breasts that fit the rest of her petite figure perfectly. Striking green eyes and an easy smile fit under her shoulder length auburn hair, rounding out her sexy look. The fact that she was incredibly hot never escaped me, I'd endured enough teasing about my hot sister from all my friends. But now, with my name on her lips as she came...

I was fully hard now, my cock tenting the blanket. I tried for a while to distract myself and go to sleep, but my unrelenting hard-on stood tall, begging for attention. Finally, I rolled out of bed and retrieved my fleshlight from the spot in the drawer where I stored it, slathered the entrance and the length of my cock with lube, and then lay on my back in bed as I lowered the tube around my cock, engulfing it completely. Silently twisting and pumping my cock within it, I closed my eyes and saw my naked sister on top of me, her small frame impaled on my length, breasts bouncing with each thrust and her eyes closed, biting her bottom lip in ultimate pleasure...

Before I knew it, I was spraying cum into the toy for the second time today. As my orgasm subsided, I pulled my cock out and wiped myself off, putting the fleshlight back in the drawer before finally drifting off to sleep.

--

"Bye guys, hope you have a great time!" Hailey called. We were downstairs the next morning, seeing my parents off. After their car pulled out of the driveway, I walked into the kitchen where Hailey was standing, sipping a cup of coffee.

"Good morning, dear brother," she said to me in a sing-song voice she knew would annoy me. I chose not to take the bait, but to play along. "Want some coffee?"

"Good morning, dear elder sister," I said back to her, "I'd love some, thanks."

Hailey turned to the single-cup maker on the kitchen counter and put a pod in, then pushed the button on top, causing the coffee maker to spring to life. She was wearing a short pair of cotton shorts and an oversized shirt, which I recognized as one of my own. Her nipples were showing through the thin fabric, denoting the absence of a bra. Hair pulled back in a single ponytail, she took a sip of her coffee and smiled at me, passing me the coffee that was just brewed. As I took my first sip, i felt a finger trace the back of my arm.

"Damn Eric, where did these muscles come from? Surely the last time I saw you, you were a scrawny little shit. Now you've got some bulk and definition!"

I stood back for a moment, wearing only basketball shorts. I hadn't bothered putting a shirt on this morning, as I didn't have plans to leave the house. Hailey surveyed me, and even chanced a fleeting glance at my crotch.

"I went to the gym and found them. Speaking of finding things... I think I just found a shirt I've been missing!" Referring to the shirt Hailey had on.

"Yep!" She said, smirking at me. "It's mine now, it's way too comfortable to give back!"

I laughed at her as she held my shirt down and tight across her stomach, accentuating her curves and causing her nipples to poke even further out. At the sight, I started to get a chub in my shorts, and slid back on the other side of the table in an attempt to hide it.

"Do you want some breakfast?" Hailey asked me.

"Nah, not a big eater in the mornings. I'm probably going to go back upstairs and lay down for a while longer," I said.

"Lazy ass!" Hailey said, grinning. "After I eat I'm going to get a head start on my marketing project, but after that let's hang out."

"Sounds good to me," I replied, climbing back up the stairs. I walked into my bedroom and flopped down on the bed, not bothering to close the door. I knew Hailey wouldn't bother me while she was working, and I easily slipped back off to sleep.

--

Around lunchtime, I woke up to the sound of Hailey's voice.

"Eric? Are you awake yet?" She called. Pretending not to hear her, I stayed still in bed and hoped she would give up. Then I heard footsteps as Hailey came into my room.

"Well, part of you is awake I can see!" Hailey said as she came close to the bed.

My eyes shot open, and looked down to my crotch to see exactly which 'part' my sister was referring to. My cock was once again the center pole of a tent so large an Alaskan trapper would have been proud.

"Damn it Hailey!" I yelled, turning to my side and bunching the blanket around my waist, trying to hide what she'd already seen. I looked up to see her laughing at me.

"Having some pretty sweet dreams, huh baby brother? Anyone I know?" Hailey joked.

"Can I please have some privacy, Hailey?" I begged her. I had definitely been dreaming of her, with that same visualization I had the night before. Her perfect tits in my face, her sweet cunt flexing around my engorged cock and milking it for everything I had to give her, the shuddering of her body against mine as she came...

"Ok, ok. Sorry!" Hailey said, turning around but not leaving the room. I sat up in bed and put on a shirt, my cock beginning to deflate.

"I'm awake, what do you want?" I asked her angrily.

She truly looked sorry. "I was hungry and wanted to see if you'd go to lunch with me. If you don't want to that's ok, I just wanted to invite you."

"No... I mean, yes. I'm hungry, I'll go with you. You're buying, right?" I asked her. The question made her turn around and put her hands on her hips.

"What, the gentleman doesn't offer to pay for his date?" She pouted playfully.

"HA! Not on your life, Hails." I said. "Give me a minute to get ready."

An hour later we sat at a diner down the street from our neighborhood. It was a favorite for both of us as kids, and we sat chatting happily about life, stealing each other's French fries and shooting straw wrappers across the table.

"How's Katie? You haven't said anything about her since I got home." Hailey asked.

Katie. I still wasn't completely over her, despite the fact she'd dumped me a month ago. We dated all through junior and senior year of high school, then suddenly she decided that she didn't want to go off to school with 'an anchor trapping her at home', as she referred to our relationship. As I told Hailey what happened, I watched her face turn from sadness, to pity, to anger.

"Are you fucking serious? I can't believe she said that! I really thought she was better than that. I'm really sorry that happened to you Eric, you deserve better," she said.

"Thanks," I told her. "It hit me pretty hard when she dumped me, but I'm doing better now. It would have never worked anyway, she's going halfway across the country to school."

"So... might that be the reason that my baby bro now has a girlfriend he keeps in the drawer in his bedroom?" She asked, lips turned up on the corners with a small grin.

"Really Hailey, this again? I said I was sorry you saw that, you said you wouldn't talk about it again!" I said, exasperatedly to her.

"No, I said I wouldn't tell mom and dad, I said NOTHING about not giving you a hard time about it... besides, I bet you give it a hard time!"

I was beet red, and Hailey noticed that I was getting uncomfortable. She lowered her voice to little more than a whisper and looked at me seriously in the eyes.

"Look, I've already told you that it's ok. There's nothing to be ashamed about, everyone has needs and just because you're my little brother doesn't mean you don't. You're human, and so am I," she said gently to me.

Treading lightly with my reply, I said, "Believe me, I know you have needs, too."

Now it was Hailey's turn to be embarrassed. Shifting a little in the booth, she asked, "What do you mean by that?"

"So... when I came upstairs to go to bed last night, I passed your room and heard a humming noise, then I heard your bed squeaking a little bit, I put two and two together and figured that you must have a vibrator you were using," I said gingerly, hoping that my guess was accurate and she wasn't in there doing something completely innocent and I was just being a perv.

Redness flooded my older sister's cheeks and she looked away for a moment, as if she were contemplating what to say in return.

Looking back at me, she asked, "So... what else did you hear?"

I'm usually a pretty honest person, but I also know when it's a good time to lie straight through my teeth.

"Nothing," I answered, maybe a little too quickly. When she hesitated, I followed up, "I was just passing your room and when I heard it I hurried past and went into mine."

Hailey, looking relieved, cracked a tiny smile. I don't know that she intended it, but the look that she gave me, though innocent and sincere was a complete turn-on. She was so beautiful, even when she wasn't trying to be, and the authenticity of her response accentuated her attractiveness.

"Well," she said finally, "I guess now we both know a little more about each other!"

I laughed in earnest, and both of us felt the tension of the moment melt away almost instantly. I couldn't help but feel like maybe a line had been crossed, however. If it hadn't, we both were walking right along it.

--

Leaving the diner, Hailey dragged me around town for the rest of the afternoon, running some errands. Our last stop was the grocery store, and Hailey went ahead of me down the aisles while I pushed the basket. The arrangement worked nicely for me, being able to stare at her ass with little chance of her catching me. The sway of her hips as she strolled through the store hypnotized me, her shorts slightly tucked in between her cheeks, accenting the perfect shape.