Virgin Sister's Valentine Read online

  Virgin Sister’s Valentine

  By

  Hannah Hale

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  Copyright 2012 by Hannah Hale

  Smashwords Edition

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  This eBook is licensed for your personal enjoyment only. This eBook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you're reading this book and did not purchase it, or it was not purchased for your use only, then please return to Amazon and purchase your own copy. Thank you for respecting the hard work of this author.

  This book is a work of fiction. Names, characters, places and incidents may have been inspired by genuine events but have been written and used fictitiously. All rights reserved. No part of this publication may be reproduced or transmitted in any form or by any means, without prior permission in writing from Hannah Hale.

  All characters are 18 years of age or older.

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  Virgin Sister’s Valentine

  I sat at my desk trying to concentrate on the history exam in front of me. I had studied for the exam all weekend and knew the material, but my mind just wouldn’t focus on the questions. Earlier in the day I had found a small red envelope with a card and a bite-sized foil wrapped chocolate heart taped to my locker. The card inside was cryptic and anonymous saying only, “I’ve wanted you for so long. Be mine?”

  I had no idea who had given me the secret valentine and it had been driving me crazy all day. With my thoughts consumed by the mystery of the sender, all of my hard work studying rendered useless as I filled in circles on the scan-tron at random. Filling in answers was better than not answering the questions at all. I quickly finished with only a few minutes to spare before class ended.

  The bell rang and I hurried down the hall to my locker. Brooke, my BFF since the third grade, was waiting for me impatiently with her lunch bag already in hand.

  “Cassidy, finally! So how was the test? Is there anything I should know for when I have to take it this afternoon?” Brooke asked, I knew she was freaking out about the test.

  “Uh, shoot, Brooke… I don’t even remember what was on the test. I think I bombed it.”

  “What? Why? We studied all weekend for it, how could you have bombed it?”

  “Because of this,” I fished the valentine from my bag and handed it to Brooke, “I couldn’t concentrate on the stupid test because I had no idea who would send me something like that.”

  Brooke read the cryptic valentine, turning it over twice to see if we had missed any information regarding the sender.

  “Do you have any ideas, any at all?”

  “No, you know I haven’t had a single date since our freshman year,” I huffed. It wasn’t like I wasn’t pretty, or fun, or sweet. I knew I was well liked by my classmates and more than decent looking, but I was also the shy smart girl that guys overlooked when asking out because they thought I wasn’t the type to put out, which was only true because I had never been given the opportunity. Losing my virginity was still high on my list before going to college in the fall. I couldn’t believe my virginity was still intact at eighteen, and it wasn’t even something I chose.

  “Hey! What’s up?” Seeing the look on my face as he approached, Tyler, my step-brother since the sixth grade, gave me his questioning one eyebrow arch, “Everything alright?”

  “Yeah, sort of,” I replied as Brooke handed the valentine to Tyler, “I bombed my history test because of this.”

  “You did? Why would this have anything to do with your test?”

  “I was just too distracted by it. I couldn’t think straight trying to figure out who could’ve given me, of all people, a valentine. I just don’t get it.”

  Tyler chuckled and gave me a squeeze, “Hey, sis, you’re not as bad as you think. In fact, you’re probably the prettiest girl in our class, but the stupid douchebags are too blinded by the T&A of the cheerleaders that you get overlooked. It’s not you, it’s them, and obviously someone else sees that too.”

  “Wow, Ty that was uncharacteristically sweet of you.” I laughed as I gave him a squeeze back.

  “I have my moments,” Tyler beamed his signature smile down at me and trotted after his fellow ‘douchebag’ friends for lunch. He looked back once more at us and winked before walking through the cafeteria door.

  “Ugh, why does he have to be so damn cute?” Brooke lamented staring longingly after Tyler. Back in the sixth grade Brooke thought I was the luckiest girl in the world because Tyler Cavanaugh was going to be my step-brother and I would get to see him morning, noon, and night. The only problem with that was I couldn’t have a crush on him anymore because he was now technically my brother. Brooke could keep her crush, and actually see him after school when she came over to hang out with me. It was great for her, not so much for me.

  I had harbored my secret crush for Tyler closely since then. I hoped he wouldn’t ever find out I wanted to jump his bones. He would think I was crazy if he ever found out. I mean, who wants to fuck their brother? It would be so wrong. I don’t think I would ever be able to be normal around him again. Being shy sucked. Being shy and thought a pervert… that would kill any social life I had.

  I shrugged at Brooke’s “cute” comment muttering, “C’mon,” and walked into the cafeteria after Tyler with her. We sat at our usual table close to the middle with a few of our friends. I opened my lunch bag and fished inside to see what my mom had packed for me today. I felt something hard, rectangular, and small inside the bag and pulled it out.

  “Uh, I think someone left their homework in my lunch bag,” Brooke grabbed the offending object to save herself from more of my humorless sarcasm.

  She turned the pink USB memory drive over in her hand, “Look, Cass there’s something written on the back.”

  I took the drive from her hand and flipped it over myself reading the words on the back, “Watch me.”

  “Well, it looks like somebody’s homework just a got a little bit hotter,” Brooke snarked.

  “Yeah, but how did they get it into my lunch bag?”

  “Who cares? My guess is that it’s your secret wannabe valentine.”

  “Probably, I guess I’ll find out when I watch it.”

  “I hope it’s some uber hot guy wanking off to your photo or something.”

  “Oh My Gosh, what if it is?” I felt a zing of excitement shoot straight down to my pussy making me just a little bit wet at the thought of some random guy wanking off for me.

  Brooke laughed, “Promise me you’ll call me right after you find out?”

  “Oh, you’ll be the first to hear about it!” I was beginning to think this whole secret valentine thing wasn’t so weird after all. I kind of liked it. I’d never been given any sort of attention from any of the guys at school and I was excited by the prospect of solving the mystery. I hoped it was someone I liked, even if as just a friend. I could definitely work with that. If it happened to work out this could mean finally losing my virginity, thank God.

  ***

  Walking into the house after school I stopped in the kitchen grabbing an apple and then trotted up the stairs to my room. I closed the door and locked it. I wasn’t too worried about anyone barging in with mom running errands, my step-dad at work, and Tyler at water polo practice. I had the house to myself, but locking the door seemed like a good way to cover all my bases just in case there was something I didn’t want anyone to see on the mysterious memory drive.

  I fished the memory drive out of my school bag and inserted it into my laptop sitting on my desk. I sat down and waited for my video player to load and I pushed “Play” when it had finished. My secret valentine had hand written a commen
t on a piece of paper and held it in front of the camera so I could read it:

  “This is what happens every time I think of you.”

  He took the paper away from the camera and a fully erect cock stood at attention before my eyes. Nothing else, just a long thick cock filled the view of the camera. I gasped in surprise. It really was some guy’s cock just like Brooke had joked, but I had never ever thought that would actually be what was on the mysterious memory drive. I couldn’t see a face to identify whose cock it belonged to, but I saw a hand and some seriously ripped abs above the base of the cock. Nice, VERY NICE.

  He grabbed the base of his cock and began to stroke. It made a noise like a dog lapping water, only a little bit slicker sounding. I had never seen a guy jack off before and I was enthralled by the hand sliding up and down the long thick cock.

  The sliding hand stroked faster and his hips were pumping with the motion of the hand. I could hear him breathing heavy and fast as he pumped. He groaned deeply and shot his load in the air. It was like a spewing fire hydrant. I sat there amazed watching his body jerk as his cum spewed. He laid there a second and then held another hand written piece of paper with his sticky hand in front of the camera:

  “Get on your webcam at 8pm tonight. Add me: AllMine69”

  The screen turned black as he turned off the camera. I pushed play again. I couldn’t get enough of the huge cock spewing just for me. I was fixated watching over and over again.

  There was a knock at the door and I slammed my laptop shut, “Hey Cass, a package was left for you on the front porch. I brought it up for you.” Tyler yelled through the door.

  I stood up and ran over to my door, stood a second to calm myself, unlocked the door and opened it, “Thanks Ty, I wonder what this is?” The package was wrapped in silver paper with a silky red ribbon.

  “Looks like your mystery man strikes again.” Ty teased.

  “Ha, you have no idea.” I smiled at the thought of this mystery guy thinking I was hot enough to wank off to.

  “Dad just told me he’s taking your mom out for Valentine’s tonight. I think I’m just going to hang out here, order a pizza and watch a movie. I’ll be around if you want company.”

  “K, thanks. The mysterious valentine has something up his sleeve at 8pm, but I’ll hang out after if he doesn’t have anything else to surprise me with for later.” I winked at Tyler, shrugged shyly and laughed.

  Tyler grinned and shook his head as if I were a giddy little school girl… which I was, “It’s nice to see you so happy, Cass.” He said walking down the stairs to start his night O’ fun.

  I closed the door to my room and sat on the bed with the package in my lap. I wondered what my sexy valentine was up to, and how he managed to get past the security gate to drop the package off on our porch. Sneaky little devil. He definitely had made an impression.

  Unwrapping the package I found black lacy lingerie and a card. It was simple and sexy and perfect for my full breasts and hourglass shape. It was hot that he seemed to know me so well, and it definitely meant he had been checking me out for a while to know just what would be perfect for my body. I opened the card and read, “Wear this tonight.” Well, that wouldn’t be a problem, I was already hoping something fun would come of the webcam rendezvous and now I wouldn’t have to worry about finding something sexy to wear. Nice job, mystery man!

  I looked at the clock on my night stand. It was already 6:30pm. I still had to hop in the shower, do something with my hair, and put a bit of make-up on for my webcam Valentine’s “date’. I needed to hurry if I wanted be done with time to spare. I hated getting ready right up to the minute. It frazzled my nerves and I wanted a half hour before getting on the webcam to calm myself.

  An hour and a half later I was ready and looking pretty sexy in the black lingerie as I sat on my bed. I heard my mom call out to us as they left for their Valentine’s date, and knew it was almost time. I opened my laptop as I sat on my bed and searched for “AllMine69” on my video chat. I found it. The butterflies in my stomach fluttered as I pushed “Add” and instantly he had accepted. My heart jumped out of my chest. This was really happening.

  He messaged me, “You look beautiful.”

  Again, all I could see were boxer briefs without a face to go with the amazing body of my valentine, “Thank you. Why can’t I see your face?” I asked.

  “Not quite yet.” He IM’d instead of speaking. Strange.

  “And why can’t you talk to me?” I asked growing seriously perplexed.

  He IM’d me again, “You’ll know who I am if I do.”

  “But I want to know who you are!” I was pouting just a little bit. I really wanted to know sooner rather than later. I was already going crazy trying to figure it out.

  “You will, but not yet. Do you want to play a little first?” He wrote.

  “Uh, yeah sure… but you’ll have to start, I’m a little shy. I liked the video you gave me.” I suddenly had grown shy now that this was actually happening. I needed to see his cock to warm me up.

  “Good, I was hoping you would.” I read.

  I watched as he stripped off his boxer briefs. He was already hard and standing at attention. I licked my lips as he grabbed his cock and began stroking.

  “Your lips look juicy,” he wrote as I licked them at the sight of his cock in front of me, “You’re thinking about licking my cock, aren’t you?”

  I nodded, still a bit shy. He was stroking his long hard shaft and I could hear the same sounds I did before on the video earlier. It was so hot. I felt my pussy tighten with the thought of stroking his cock myself. I wanted to put it in my mouth and feel it hit the back of my throat as I sucked him off.

  “Can I watch you touch yourself?” he wrote quickly.

  “Uh huh,” I replied

  “Stand up,” He commanded and I did, “turn around and bend over as you finger yourself, I want to see your ass while you finger your pussy.”

  I turned around and bent over slowly inching my fingers down to my wet slit. I turned my head around so I could still see him stroking his cock while I rubbed my clit. He was stroking faster now with the sight of me playing with my pussy lips and I could hear the slurp of his hand sliding up and down his cock.

  I slipped a finger into my pussy and I heard him groan from behind me through the cam. I fingered my slit feeling the wet creaminess run down my finger as I pumped in and out. I pushed another finger inside feeling my pussy contract around them. I was tight. I needed to be fucked.

  I was so engrossed in what I was doing to my pussy I didn’t notice that the sound of his hand sliding up and down his cock had stopped. I turned around and his cock was still in view though it seemed like he was walking instead of sitting like he was before. Before I could ask what he was doing the door to the Jack & Jill bathroom I shared with Tyler opened. Fuck! I forgot to lock the bathroom door when I locked my bedroom door.

  I was on my bed on all fours with my ass facing the bathroom door with my fingers lodged tightly in my cunt as Tyler walked into my room naked and with his laptop in hand. I was too shocked to move. What was going on?

  “Hey Cass,” he said huskily as he walked toward the bed, “All mine 69,” he said pointing to himself with his thumb. I was dumbfounded. My secret valentine was Tyler?

  I looked at his face and then looked at his cock. Yep, it was him alright. That cock definitely had left its mark in my memory.

  He put his laptop down on the bed next to mine and kneeled behind me, “Tyler?” I knew what he was about to do, and the look on his face was full of need as well as… love? Oh My Gosh, Tyler loved me. ME. Holy crap.

  He saw the look on my face as I realized his feelings and he bent his head toward my wet pussy. He slipped my fingers out and sucked them clean before lightly tracing my pussy lips with his tongue. I shuddered. I had never felt anything like it before. Soft and wet, it almost tickled.

  He buried his face further into my pussy slipping his tongue into my slit lapping my cream
. As he licked he rubbed my clit with his thumb. The combination of the two made me thrust my pussy deeper into his face. I rocked my hips wanting more as his head came up and I whimpered with the loss.

  “Do you want me to make love to you, Cassidy?” He huskily groaned.

  I could tell he wasn’t going to be able to control himself for much longer as I whispered, “Yes, I want you.”

  Still kneeling behind me he prodded my wet pussy with his cock. I knew it was going to be a tight fit and that it would hurt for a minute, so I prepared myself and grabbed hold of the blanket beneath me. He slipped the tip just inside and I already felt the fullness inside my small slit. God, it felt good. Tight, but good. He pushed a little further and I could feel my pussy opening wider for him as he stopped at the thin veil that protected my virginity. I could tell he was hesitating not wanting to hurt me.

  “Do it, Tyler.”

  He groaned and thrust quickly into me with his long thick cock. I screamed and threw my head back as he stilled again now that he was fully inside me waiting for the pain the ease. He slowly started thrusting, being gentle enough not to hurt me again, but I could tell he was straining to keep it together and not fuck me too hard. I pushed back with my hips as he thrust as hard as I could hoping he would take it as a sign to just fuck my brains out like I knew he wanted to. He did and his thrusting gained speed. The slap of his balls against my ass was so hot as he pumped into me.

  He leaned over my back and grabbed my tits pushing the sexy black lingerie he had given me down to my waist. He massaged both and then finding my nipples circled them between his thumbs and index fingers. A zing of electricity raced through me down to my aching pussy. I rocked into him harder as he fucked me senseless from behind. I could hear him groaning as he touched and fucked me.

  Quickly pulling out, he turned me over. I liked how he man-handled me like he knew exactly what he was doing and what he wanted to do to me. He was so gorgeous leaning over me as he lifted my legs over his broad shoulders. He stopped for a second gazing at my face and then took in the rest of my body.