Toying with Hailey

"OH FUCK, FUCK, FUCK!" Hailey screamed. The effect was immediate and I felt her pussy clamp down. Her arms gave out and her entire tiny body was quivering, being rocked by the her intense climax. The sensation on my cock sent me over the edge, as I bottomed out and sprayed my big sister's insides with my cum. Her pussy continued contracting, milking all of the cum out of me. I held still, catching my breath and heard Hailey whimpering, which turned into a long, low moan as I slowly removed my cock from her depths. Finally pulling all the way out, I sat back on my legs and watched as my cum dripped out of Hailey's pussy and onto the bedsheet.

Completely spent, Hailey turned over and collapsed flat on her back, still trying to catch her breath.

"I... have never... been fucked like that before." She said between gasps.

"You are easily the best I ever had, Hailey. Damn that was fucking awesome," I said. I was searching for words to describe what I was feeling but I had none. We lay cuddled up for a few minutes, relaxing and trying to recharge. She looked up at me and smiled weakly.

"So... finger in the ass, Eric? That's a first for me." She confessed.

"Did you like it?" I asked.

"Honestly I thought I still had a little while to go before I came. As soon as you stuck it in though, it took me straight over the edge. That was probably the most intense orgasm I've ever had." She said.

"You're welcome!" I said with a sideways grin at her, laying back and resting my head on my hands.

"Now hold your horses there cowboy, don't start getting any ideas about sticking anything else in there! Are you aware how gifted you are in the dick department?" She said, wide-eyed.

"I mean, I haven't exactly had measuring contests with all my friends, but I had a pretty good idea," I said.

"For a minute, I wasn't sure I was going to be able to take you all the way in my pussy. I'm glad you started slow."

I scooped her up in my arms. "I am so happy right now, Hailey."

"Me too, baby brother," She said. "I love you."

I kissed her lightly. "And I love you."

We slipped out of bed and got in the shower, cleaning each other and enjoying the hot water on our skin. After the shower, we dried off and got back into bed, neglecting any clothes, and drifted off to sleep.

--

For the first time in almost three weeks, I awoke without Hailey by my side. Without her as a source of warmth, I felt a shiver. Getting out of bed, I put on a pair of shorts and a t-shirt and walked out of my room. I looked through her open bedroom door and saw her room empty, so I went downstairs and found her sitting at the bar in the kitchen, a cup of coffee and a sad expression on her face.

"What's wrong, Hailey? Are you ok?" The previous night had ended much in the same way as all of our nights in the past weeks, falling asleep in bed together.

"Yeah, I'm ok Eric... Just realized that Mom and Dad get home tomorrow."

The fantasy world I'd been living in halted with a record scratch. The parents were coming home, and they would be beyond furious if they were to find out what had been going on under their roof between me and my big sister.

"Damn," was all I could come up with as a reply.

"Yeah."

All of my concerns came out at one time like an avalanche.

"Hailey, I can't forget these last few weeks. I've never felt like this before, I can't give you up. I don't know what the future looks like but if it's without you, I don't want it." I slowly embraced her, my mind full of doubts. I looked deeply into her eyes, trying my best to convey what I was feeling. "I'm in love with you."

Hailey kissed me. "I'm in love with you, too. And that is something that is not going to change. I'm yours, but now we have to go back to acting like brother and sister. It's probably not a good idea to spend the night together anymore, and we are just going to have to be careful how we act in front of them."

My spirits lifting a little, I said, "That's going to be hard."

"Yeah, it will. But they aren't around all the time, we'll still find ways to be together. It probably just won't be every day."

"Well, I guess we have one more night together before things go back to normal, right?" I asked. "We're going to have to make it special."

Hailey smiled at me, with a little twinkle in her eyes.

"Eric, you have no idea what's in store for you. Tonight, I'm going to rock your world."

Mind racing as to what that meant, I went about my day, occasionally catching my sister looking at me with a grin that I knew meant she was up to something.

Mid-afternoon, she came up to me.

"Hey, I was just thinking. Let's go out tonight. Like on a date," she said.

"That sounds great!" I said. "Where to?"

"What do you think about Sicily's?" She asked. It was a posh Italian restaurant a town over. I got excited about the fact that being in a different town, we were less likely to come across someone we knew, and so any public affections we may display wouldn't be frowned upon, or reported to our folks later.

"Excellent," I said, smiling at her.

"Good, because I already made reservations. I hope you're hungry, because I got an early table. I want as much time tonight with you as I can get." She said.

--

We walked arm in arm into the restaurant, just another couple on a date night. Walking up to the desk, Hailey gave her name and we were escorted to our table, dimly lit with candles and soft music playing in the background. I pulled Hailey's chair out for her, and she smiled warmly at me as she took her seat. She was wearing a black dress, with small straps over her shoulders. The hem hitting right above the knee, it had a slit midway to her thigh, and she wore it like she was doing it a favor! As I took my seat, The waiter approached the table.

"Welcome! Can I get you a drink? Maybe a glass of wine or a cocktail?"

I looked quickly across the table at Hailey, wondering if we played it cool, could we get some drinks. As I was 18 and she was 20, neither one of us could legally drink. She took the lead.

"I'll have a Pinot Grigio, what about you?" Looking back at me.

"I'll go with a Cabernet," I said, handing the drink menu back to the waiter.

"Of course, I'll be back," and without another word, left us to put the drink order in.

We giggled at each other, impressed with our clandestine efforts to commit crime together.

We ate and talked our way through four fabulous courses, and found ourselves sharing tiramisu and drinking Italian coffee.

"Well, love, how did you enjoy dinner?" Hailey asked me.

"It was amazing! I think I'm going to enjoy dessert a little more, however," I said with a wink to her.

"I agree, this tiramisu is top notch!" She said, smiling widely at me, knowing full well the dessert I was referring to was her. Well two can play at that game!

"Yeah," I said, leaning back and taking a sip from my coffee, "We'll have to see how the second dessert stacks up to the first."

I felt a small kick under the table, and saw a smoldering look from Hailey. "You have no idea, baby brother... no idea," she said quietly, after looking around to see if anyone was in earshot.

"Let's get out of here, Hails. As good as that dress looks on you, I think it'll look much better crumpled up in a heap on the floor." That was all it took for Hailey to hear. She half-dragged me out of the restaurant.

--

Hailey dragged me up the stairs as soon as we got home. I barely had time to lock the front door, and the entire trip home, we couldn't keep our hands off each other. Pulling me into my room, Hailey turned to face me and kissed me passionately, my hands roaming the sides of her body, traveling down to squeeze her ass, then back up to cup her breasts. Stepping back, she pulled her hair over one shoulder, exposing the small zipper that ran up the back of her dress. She looked back at me seductively, and bit her bottom lip.

"A little help?"

I stepped up and located the zipper pull. Placing one arm around my sister's waist, I slowly exhaled, blowing gently on the back and side of her neck. She trembled at the sensation, and reached behind her to put her hands on my thighs. I slowly lowered the zipper, placing light kisses on her shoulder blades, and down the center of her back where the dress had previously covered. Lowering to my knees behind her, the zipper finally stopped at top of her ass, and I was about to slip my hands under to caress her legs when she turned around. Looking down at me, she was holding the front of her dress up with one hand and caressing my face with the fingertips on the other. She slowly let the dress fall from her chest, slipping down her waist and past her hips, until encountering no more resistance from her delicious curves, fell to the ground around her feet.

She stepped out of the dress, now down to a pair of heels and a black thong. She hadn't been wearing a bra under her dress, and as the fabric drug across her chest when taking it off, it rubbed her nipples, now responding and becoming hard and pronounced. Still on my knees, I reached out and touched her nipples, garnering a quiet sigh from her and pressing her legs together.

"You remember how this whole thing between us started, baby brother?" She asked quietly.

My fleshlight had been in its spot in my top drawer for the last 3 weeks now, neglected from use. My cock now had a new home inside my big sister. Her skilled mouth and velvet lined tight pussy had rendered the silicone cock sleeve useless.

"I do remember," I said. "I would have never dreamed in a million lifetimes that you catching me with a fleshlight would lead to all of this."

"Do you remember when I showed you my vibrator and told you how I used it?"

The vibrator had made some appearances during the encounters between me and Hailey. We used it a few times to heighten the pleasure between us as we made love.

"I remember," I said, wondering where she was going with all this.

"Well," Hailey said to me, "I have one more toy I want to show you."

Without another word, Hailey turned around and put her ass inches from my face. She reached back and began pulling it down, the center string peeling away from the inside of her cleft. Bending over, I caught a glint of something shiny that had been hiding under her dress and thong all evening.

My sister was wearing a butt plug.

Upon registering what it was and where it was inserted, my eyes went wide and my cock, already hard from watching her seduce me, began to throb.

"Oh my god..." I breathed. I reached between my sister's ass and softly touched the metal end of the plug that was sticking out of her asshole. Feeling the sensation, Hailey gave a small moan.

"I bought it the day after you put your thumb in my ass, Eric. I've been wearing it every day during the day, preparing myself for you."

Hailey flexed the muscles in her ass, causing the plug to make small movements in and out.

"Do... do you like it?"

"I love it, Hailey. I love you." I said, standing up as she turned to face me again.

"I love you, too, Eric." She said. She reached up to the collar of my shirt and started unbuttoning it. When all the buttons were undone, she slid my shirt off of me and tossed it down on the floor, next to her dress. Reaching for my waist, she unbuckled my belt, then opened up the front of my pants, helping me out of them as well.

She then got on her knees and kissed the tip of my cock, already showing its approval by leaking pre-cum from it. Reaching under and caressing my balls, she licked my shaft momentarily before fully engulfing it in her mouth, sucking it softly and letting out small moans. I stood before her with my head back, both hands on top of her head, as she continued making love to my cock with her mouth. I began to thrust into her slightly, and she opened wider, placing my cock at the back of her mouth... then down her throat. My eyes rolled to the back of my head as she held it in her throat, only releasing me when she finally had to breathe.

I reached down and grabbed her arms, and pulled her to a standing position, then picked her up and held her in the air for a moment, enjoying a long, slow and passionate kiss. Moving toward the bed, I then threw her backward. She landed softly on the bed with a squeal, and I quickly laid down before her, burying my face between her legs, sucking on the lips of her pussy, already drenched with desire. I found her clit and focused my attention on it, flicking it with my tongue. Knowing exactly what it took to get her to her climax, I wasted no time and she quickly came, a sharp, intense orgasm that further fueled her desire.

I moved up even with her on the bed and kissed her, letting Hailey taste her own juices that were still on my lips. She pushed my shoulders flat on the bed, and straddled me, slowly lowering herself on my cock and riding me. I could feel the plug moving as she rocked back and forth, and I knew she was feeling the stimulation in both of her holes. After a few minutes, she looked at me apprehensively.

"I want you to put your cock in my ass." She said, her voice trembling with anticipation and anxiety.

"Ok, Hailey. Stop me if it starts to hurt, ok? The last thing I want to do is hurt you," I said.

She nodded and said, "Just go slow at first, I'll be fine."

Hailey got on all fours on the bed. I positioned myself behind her, and pulled gently on the plug planted in her asshole. As I continued pulling, a loud moan escaped her lips, and her starfish began to open up, letting the butt plug slip out. As soon as it was out, her tiny hole snapped shut.

"Are you sure you're ready for this?" I asked one last time.

"Yeah, I am. Grab the lube," she said.

I got the bottle of lube and squirted some onto my finger. Massaging around her hole gently, she purred and pushed her hips back slightly. I then slowly inserted my finger in her rectum, feeling the muscles in her ass to stretch and adapt to it. Withdrawing slightly, I kept a slow rhythm going to make sure she wasn't in pain.

"I'm ready for your cock now," she said, once she was comfortable. I pulled my finger out of her asshole, and grabbed the bottle of lube again. This time I put it on and around her asshole with two fingers, then slathered a liberal amount on the entire length of my cock. I grasped her hips and lined my prick up with her back entrance, and started applying pressure. Hailey pushed back against me once again, and slowly her ring began to expand, receiving the head of my cock. Holding still with just the tip in, I caressed her ass cheeks with my hands.

"I'm going to go really slow, just let me know if it's too much and we'll stop," I said.

"I will. Be gentle, love." She said.

I continued pushing my cock further into my big sister's asshole. Going agonizingly slow, inch by inch, my cock disappeared into her hole, which was stretched out to accommodate my girth.

"Are you ok?" I asked when I was about two-thirds the way in.

"It hurts a little, but it's not bad... it actually feels amazing, I just have to get used to it. Keep going."

I kept going. Not a minute later, my cock was fully inserted in Hailey's asshole. I held still again and waited for her to give me the go ahead.

"Ok, go slow baby brother. Fuck your sister's asshole," she said to me. I slowly withdrew until I saw her ring slightly close around the head of my cock, then went back in. When I thrust forward, she let out a deep, guttural moan but pushed back into me hard. Bottoming out in her asshole once again, I started picking up a little speed in my thrusts.

As my thrusts got faster and stronger, Hailey worked herself into a frenzy, pushing back against me, and using one of her hands to finger her pussy. I felt the muscles in her asshole begin to tighten and her moaning get louder. Suddenly her asshole clamped down on my cock and she let out a scream as she came, the double stimulation of her fingers in her pussy and my cock in her asshole overtook her. I couldn't withdraw my cock until she came down from her orgasm, but when she did I found it easier to move in and out.

"Cum in my ass, baby brother. Please!!" She begged me. It was all the encouragement I needed. I had been on edge watching her orgasm, and so a few strokes later, I poured all of my cum deep into my sister's bowels. She yelped as my cock spasmed in her tunnel, and finally, having dumped all of my seed into her, I began removing my cock from her. When the head of my cock finally reappeared, her asshole closed, retaining all of my cum inside her.

"FUCK that was hot!" Was all I could say as I turned over, laying back on the bed.

"Yes it was, little bro," Hailey said, moving toward me and kissing me. I was in heaven, having just fucked my sister's ass. Nothing could bring me down from this high.

We relaxed on the bed for a few more minutes, kissing and laughing with each other.

"That was so intense," Hailey said, shaking her head and smiling at me.

"Was it too much? If it was, I totally understand." I said, worrying that she might be hurt.

"Not at all! You took some getting used to, that butt plug isn't near the size of your cock. I'm glad I had it though, I don't think I'd have been able to take it if I hadn't prepared. I loved it, I hope you did too." She said.

"I did!" I answered, staring at her perfect body, laying naked next to me.

"Ok, I'm going to clean up a bit. You coming?" Hailey asked me.

"Yeah, I'm right behind you." I replied.

"Oh, don't I know that!" She laughed. "Besides... I need to get out of these," and pointed to her feet.

She was still wearing the heels she'd worn to dinner.

--

Hailey and I spent most of the night making love. I stayed away from her ass for the rest of the evening, she finally admitted that despite how good it felt, she was a little sore. I was all too happy to give her a break.

"So back to normal life tomorrow, I guess." I said. Hailey had just finished sucking my cock and was laying with her head on my thigh, tracing up and down my softening cock with her fingers.

"I guess so," she said glumly. "But hey. I want us to promise to each other right now that we won't stop this. I never want to be without you again."

"I promise, Hailey. I'm in love with you."

"Good," she said. "I'm in love with you, too."

--

We woke up at the same time the next morning. Snuggled up against each other, it was a moment we never wanted to end. Looking up at the clock, Hailey sighed.

"Damn it. Mom and Dad's plane lands at 11:00, which means they'll be home a little after lunch. We probably need to do some clean up and make sure the house doesn't look and smell like a summer fuck camp."

I laughed at the description she gave, but sadly agreed with her. We got up and dressed, washed our sheets and clothes, and gave the kitchen and living room a good cleaning, looking for possible evidence of siblings having sex. By lunchtime, the house was spotless, ready for my parents to walk in.

Hailey made us both some lunch, and we were sitting together on the couch when we heard the car pull up in the driveway. We looked at each other for moment. Having the same idea, we both went in for one last kiss before our parents walked through the door. Breaking the kiss with a sad smile, a few seconds later the front door opened.

"Hey, good to see that the house and intact and both of you are still alive!" My Dad said. Hailey ran up to him and gave him a hug.

"Your little brother didn't give you much trouble, did he?" Mom asked.

"Nah, he wasn't bad at all. It was actually nice being able to hang out with him after being at school all year long." Hailey said.

"Good!" Mom said. "I'm glad you both have a good relationship, it makes it easier on the parents when their kids aren't trying to kill each other."