My Sister’s Best Friend Chapter 1

Please enjoy the story. There’ll be more where it came from. Bonus points if you recognize the names from a TV show.

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I couldn’t believe this was happening. How could I have been so stupid? I was really screwed now.

For the past few days, my sister, April, has been letting her friend Natalie stay with us while our parents were out of town for the while to visit far away family. It wasn’t exactly my idea of fun; two college age women commandeering the entire house for themselves? No thank you. Besides, I never really liked Natalie to begin with. She was loud, stuck up, haughty, and so full of herself I wanted to slap her every time she opened her mouth.

I never thought I could ever find Natalie attractive. Not just because of her loud personality, but just the way she looked and acted. She was rather tall and ridiculously skinny and had a permanent scowl plastered on her face. Her choppy haircut fell in dark waves over her shoulders that I thought just looked silly. I was skinny enough, too, but I was quiet and contempt with sitting at home all day watching TV and eating cereal while Natalie was out doing who knows what with who knows who.

Despite all this… Well, let me just say one thing. With Natalie hanging around the house all day long doing nothing, there hasn’t really been any time to spend alone. I hadn’t been with anyone in quite a long time, and between both her and my sister, there was no way I could find time to relieve myself, let alone bring a girl home. There was no way I was going to risk getting caught by either of them by sneaking off in the middle of the night, either.

So when Natalie announced that she was going to run some errands and would most likely be gone for the rest of the day, I took it upon myself to use this opportunity wisely and treat myself. It had been so long, I thought I would go crazy if I didn’t blow my load soon. However, as I proceeded into my room to do so, I quickly found myself unenthusiastic about the situation. It had gotten to the point where my hand alone could no longer do the trick. I needed something more, and- oh no.

Before I could realize what I was doing, my head quickly turned and stared into the guest room right across the way, where Natalie had been staying. I thought about it for a long while, before finally taking a deep breath. Okay. It was fine, it would be fine. Natalie would be gone for the rest of the day, and… What she doesn’t know won’t hurt her, right? Terrible philosophy. But I didn’t care, and neither did my hormone driven horniness.

Removing myself from my bedroom, I quickly snuck across the hallway and dove into the bureau that Natalie had been using while she was staying with us. I opened and slammed shut the drawers as fast as I could, searching for the woman’s underwear. Of course, they were in the last one I checked. I snatched a pair of her panties – a horribly cliché pair that were pink and had red hearts scattered across them – and returned to my room. Dropping my pants to the floor, I sat on the edge of my bed in just a t-shirt and boxers. I began pleasuring myself while clutching the panties tightly. I imagined Natalie wearing the underwear upon her slim, slender hips.

It had been only a few minutes, but I could feel my climax quickly approaching. I began breathing heavily, working faster and faster. I was seconds away from finishing, when I heard something that made my heart simultaneously drop and leap into my throat. “Oh, my God!” Natalie screamed at me while standing in the doorway, dropping a multitude of shopping bags at her feet. In retrospect, I probably should have shut the door, but I clearly wasn’t thinking straight. “What the fuck are you doing?!” I could not believe how utterly red her face was, I honestly thought her entire head might burst from pure rage.

“I, uh, umm… You, uh… Were gone? So I um…” I sat there stuttering like a complete and total idiot. I had absolutely no excuse what I was doing. Even though I hid quickly hid my length back in my boxers, it was quite obvious what I was doing as I still tightly held the woman’s panties in my hand.

Giving me a stare of pure death, Natalie stormed at me stomping her feet the entire time. In desperation I held out the underwear in front of me like it would stop her. Pushing my hand out of the way, she reared her hand back and dealt a vicious slap to my face that left my cheek raw. Okay, I deserved that. “Are you fucking serious right now?” Natalie yelled down to me, towering above me. I couldn’t believe how humiliatingly powerless I felt at that moment. She would tell my sister, who would in turn tell our parents, who would more than likely kick me out. “I’m gone for a few hours and you think it’s okay to go in my room and steal my underwear?” Even when she yelled at me, Natalie still had that god awful annoying tone that irritating prep girls have. Like, oh my God, really? That’s sooo interesting!

I hated it. I hated it so much, in fact, that I realized that I must have subconsciously done this entire thing out of spite. And yet, as Natalie stood there, scolding me at the top of her lungs, I noticed something… weird, to say the least. I wasn’t being turned off by the situation. In fact, I was getting more turned on. Natalie was, essentially, the pinnacle of the snobby and blunt girls that are just oh so prim and proper and what have you. The idea of any sexual activities other than pure love making was nothing but repugnant to them, and consider it to be beneath them in every single way. And yet, here Natalie was, going on about how she finds her best friend’s brother having his way with himself with a pair of her underwear.

“What were you going to do with them anyway?” Natalie screamed, pushing me a bit aggressively. “Huh? Were you going to spray your disgusting spunk all over them?”

Yes, that’s exactly what I was going to do, I thought to myself. But that would just get me into more trouble, so I kept my mouth shut. “N-no,” I barely managed to say, looking away from the woman. She stood with her hands on her hips, an exasperated sigh escaping her lips in frustration.

Shaking her head, Natalie began digging around her pocket and said, “You know what, I’m calling April.”

“No!” I shouted, a lot louder than I intended to. It was difficult but I finally managed to meet the woman’s eyes for the first time.

Natalie raised an eyebrow at me. “Oh, and why not?” She asked. She paused for a moment, waiting for my response, but I fell silent. “Well? Why shouldn’t I?”

I began to panic. “Please,” I begged her, “I’ll do anything you tell me to just please do not call April.” I was extremely, extremely desperate.

Closing her phone and putting it back in her pocket, Natalie stared at me for a moment, then burst out laughing. My cheeks flared up with embarrassment. Natalie regained her posture, eyeing me up and down like she was summing me up. Nodding, she said to herself, “Okay, okay.” Then she went quiet again, standing there and staring at me.

I swallowed a lump in my throat as the fear finally began to sink in. Natalie and I have always had an extremely rocky relationship, and now I just gave her all the power she could ever ask for. It was a long while before Natalie finally said something. “Do you think I’m hot?” she asked me.

Wait, what? That certainly came out of nowhere. To be honest, I hadn’t noticed what Natalie was wearing until now. She was dressed in a deep purple hoodie and tight dark jeans that perfectly hugged her shapely curves and long legs along with a pair of light purple socks. April hated people wearing shoes. To be honest once again I didn’t think Natalie was attractive. But now that’s definitely changed.

I could tell I had been staring too long as Natalie’s face turned to once of impatience. “Yes,” I blurted immediately. “Um, yeah, I do.”

A smirk plastered across Natalie’s face for a split second, but it quickly faded. Next, came this. “Would you fuck me?” Whoa. That was a loaded question. It actually wasn’t so much a question as it was a stern statement that she made into an inquiry. Natalie crossed her arms as she waited for my answer.

“Ye-“

“How?” the woman immediately interjected before I could even finish saying yes. “Would you do it from behind?” Natalie asked. Then she glanced down at my crotch for a second. “Would you want me to sit on your lap?” The thought of her dropping her pants and riding me made my hard manhood throb in my boxers.

I replied with, “Both.”

Natalie said nothing, as if contemplating whether or not that was a good enough response. Finally she said, “Good answer.” I had to admit, I smiled involuntarily. Something about pleasing Natalie, pleased me as well. Standing directly above me, the woman said in an authoritative tone, “Jerk off to me.”

I gazed up at her, confused. “Umm… huh?”

Natalie furrowed her brows. “You’re obviously hard, right?” It was embarrassing, but I suppose it was quite apparent when I thought about it. “Just take it out and jerk off.” I loved how Natalie refused to use a term such as cock, like it was too vulgar for her to even say. That somehow made it all the sexier.

Obeying her orders, I slipped my shaft out from my boxers and made a fist around it, slowly pumping up and down. I bit my lip as I stared at Natalie’s body, not wanting to look at her face as I pleasured myself. I began to jerk myself off in front of Natalie.

Just as I began to get over the initial embarrassment for the situation, Natalie suddenly demanded, “Faster.” A slight shiver spiraled down my spine as the woman told me what to do. Even though I enjoyed it immensely, I found myself staring up at Natalie with a pleading look on my face. I hesitated for a moment, knowing that if I did so I would finish almost immediately. Natalie leaned down until she was face to face with me and yelled, “I said faster.” Her voice rose higher with each word.

As per Natalie’s instructions, I began stroking myself faster and faster. Natalie smiled down at me like she was proud I had listened to her. “Good boy,” she said, as she gave me a couple degrading slaps across my face. I turned away as she did so. Grabbing my chin, Natalie made me return my attention to her and chided, “Look at me!” I did just that, staring into her eyes as I continued to pleasure myself. “Do you like thinking about fucking me? Huh?” I nodded, because I did. In response, another harsh slap to the face. “You fucking pervert. Hurry up and finish already.”

She didn’t have to tell me to do so as I was getting quite close, but I still enjoyed it. “Mmm…” An unintentional moan escaped my lips as jerked off. I squirmed heavily in my spot as I could feel myself ready to explode.

“Oh yeah, that’s it. Shoot that fucking load all over me,” Natalie said. She uncrossed her arms and put her hands under her small breasts, squeezing them and pushing them together.

Her words were enough to take me over the edge, but I certainly enjoyed staring at her chest. “Ohhh, Natalie…” I groaned loudly as my cock throbbed in my hand. My free hand gripped the sheet of the bed as I began shooting thick ropes of sticky cum all over Natalie’s body. I leaned backwards as my eyes shut tightly, panting heavily. The realization of what just aspired finally dawned on me. Not only did I just masturbate in front of my sister’s best friend, I moaned her name as I finished. Oh boy.

Finally regaining my breath, I began to stand up. “Can I go now?” I asked sheepishly, avoiding eye contact.

“I don’t think so, little boy,” Natalie said in a terse voice. She placed both her hands on my shoulders and pushed me down on the mattress. I rolled my eyes and sighed heavily, starting to get up once again. A quick “no” from Natalie told me otherwise and I lay back down.

Before I had a chance to beg Natalie to let me go, I felt her climbing on top my body, towering over me. I had to admit, I was at the very least worried. She had a hard, determined look on her face. I could tell she wasn’t done with me just yet. “First, clean up this mess you made all over my sweater.”

I paused for a second, and then hesitantly began reaching a hand towards the zipper that hung from the hoodie. In response Natalie growled and slammed my hand out of the way, then grabbed my wrists and pinned my arms against the bed. I stared up at her, silently asking her to end these charades. She said nothing. Instead, Natalie leaned forward, until her body almost pressed against mine. I squirmed under her as she almost covered me with my own cum. “Use your mouth,” Natalie demanded. I exhaled heavily, annoyed, as I realized her zipper dangled just above my mouth. Very slowly and carefully, I took the small piece of metal in between my teeth and began pulling it downwards. Natalie leaned backwards as I did so, allowing the hoodie to peel off her body as I tugged on the zipper.

Natalie let the sweater fall to the floor, revealing to me a tight, low cut tank top that hung off her small chest and was dark blue in color. Natalie gazed at me with those unnerving eyes of hers, like she was debating what to do with her new toy. It was exciting and terrifying both at the same time. She straddled my lap, placing her hands on my chest as we locked eyes and sat in silence for what felt to me like ages.

Suddenly, Natalie grabbed both my hands and tugged at them, drawing them up to her chest. She spread my fingers open and pushed my palms against her breasts. They were perfect; round and firm, yet still bouncy. “Squeeze them,” Natalie ordered me. I complied immediately, squeezing them tightly through her shirt. Natalie smirked a bit. I had pleased her.

This continued on in silence for number of fairly awkward minutes. Then Natalie said, “Do you like my tits?” I swallowed, and nodded at her. I loved them. “Hmm, I can tell,” she replied, glancing downwards. Even though I just came not too long ago, I was starting to get extremely turned on. My hardness formed a large bulge in my boxers, which in turn rubbed against Natalie’s bottom. She ground her ass against me, causing an involuntary moan. Returning her eyes to me, Natalie shook her head and said, “Fucking perv.”

I could feel my face grow hot at her words. I wanted to please Natalie, not disappoint her. She stared down at me, shaking her head a little. “Take off my shirt, boy,” Natalie told me. And, without question, I followed her orders. I slipped my hands under the hem of her tank top as she lifted her arms into the air. Quickly I removed the article of clothing, tossing it onto the floor next to her dirty sweater. My suspicion was correct; she hadn’t been wearing a bra as her luscious breasts bounced forth right in my face.

Like an idiot I found myself staring at Natalie’s chest with no regards to the woman. I am treated with another slap and more scolding. “Hey,” she said, “my eyes are up here.”

“S-sorry…” I muttered.

“Do my tits turn you on?”

“Yes, they do.”

“So you want to jerk off on them, right?”

I couldn’t believe what I was hearing. She wanted me to do it again so soon? I felt like it was a trick that I was willingly walking into, but honestly, I could care less. If she wanted me to do it, I would do so, no questions asked. Finally, I replied with a quiet, “Yes.”

“Yes, what? What do you want to do?” Natalie pestered me in an accusatory tone. “Speak up, boy, I can’t hear you.”

Speaking a bit louder, I said, “I want to jerk off all over your chest.” I was desperate to reach for my cock and begin doing just that, but I waited for Natalie to approve my actions.

Natalie crossed her arms once again, this time propping up her breasts for my viewing pleasure. “Well get to it, then,” she demanded as she talked down to me, both literally and figuratively. I immediately grasped my hard shaft, pulled it out of my boxers and began to beat off in front of Natalie once again. “That’s it, you naughty little boy,” she said as a devious smile spread across her face, her last words said in a patronizing manner. “Do you like jerking off to your sister’s friends? I bet you blow your load to the idea of fucking me all the time. Don’t you?”

God, all this dirty talk was driving me absolutely wild. Every time Natalie talked about me doing something sexual like it was the most disgusting thing she had ever heard, it somehow managed to turn me on more and more. As I continued stroking my cock I looked up at her, locking eyes. “I do,” I said eventually. “I think about you when I masturbate, Natalie. I moan your name when I cum.” I don’t know why I felt compelled to lie to Natalie like that. I just seemed appropriate.

Natalie scoffed at my words, but she had a smile of approval on her face. “Of course you do. I’m hot. Don’t you agree?”

I quickly shook my head in compliance. “Yes, I do.”

“Then say it,” Natalie added.

“You’re hot, Natalie,” I replied with, as if she needed confirmation about that face. The woman stared at me expectantly. I figured I should say more. “I-I want to fuck you,” I admitted.

Natalie pursed her lips, pleased. “Oh, I bet you do.” Her gaze shifted downwards as she casually watched me stroking my cock. “I bet you want to shoot your load inside me. Is that what you want, huh?” Quietly I gasped at her words, letting out another moan without even realizing it. Natalie was going to make me cum just by her words.

“Ye-yes,” I stuttered embarrassingly, “I would like that.”

Natalie let out a loud and extremely pretentious laugh that made me immediately regret my words. “I don’t fucking think so,” Natalie retorted, her voice suddenly becoming hard and stern. “You’re going to cum for me again and again and maybe I’ll let you fuck me.” I loved it. I fucking loved it. I belonged to Natalie now; I was all hers to use however she wanted. And I was perfectly fine with that.

Keeping my eye contact with Natalie as I continued pleasuring myself, I said, “Yes, ma’am.” I could tell that had pleased her as her expression had finally lightened up. When Natalie wasn’t yelling at me, she was seriously beautiful. Either way, she turned me on. The thought of fucking Natalie was getting me closer and closer to climaxing. I knitted my brows as I focused on cumming.

Natalie, noticing her new plaything getting ready to blow his load, propped her breasts under her hands once again and squeezed them together for me. “Come on, little boy. Isn’t this what you wanted? Hurry up and fucking cum.” Natalie demanded me.

“Ohhh, fuck…” I groaned, getting closer and closer to finishing. My hard cock throbbed.

Natalie said, “That’s right, keep going. I want you to cum all over my fucking tits.” Panting heavily, my hips began to buckle. My eyes snapped open and I stared into Natalie’s eyes, furiously stroking my cock. My breath hitching in my throat, I let out a loud groan as I began shooting a warm, sticky load all over Natalie’s bare chest. She squealed in delight as I came on her for the second time.

Immediately after I finished, I collapsed backwards onto my bed, breathing heavily. I stared at the ceiling as I attempting to slowly regain my breath. I would have been okay with passing out right then and there, but of course, Natalie had other plans. She crawled up my body and sat directly on my lower stomach, causing me to groan as she did so. Shaking her head, Natalie said, “Look at this mess you made boy. You need to clean this up.” Something in her voice had changed, but I couldn’t quite put my finger on it.

With good reason, I stared up at the woman in disbelief. What more did she want from me? I gave her frustrated look, and then just gave in. I peeled off my shirt and tossed it at her, which she gleefully accepted and wiped herself down with. I couldn’t bear to look as she dirtied up my cloths.

Throwing the used up shirt across the room without discretion, Natalie then climbed off the bed and retrieved her belongings gathering them in a ball under her arm. She headed to leave, then stopped and turned around in the doorway. I must have looked pretty pathetic right then; a skinny, sweaty teenager lying in his bed in nothing but a pair of his boxers. Slowly, a genuine smile spread across Natalie’s face. “I’ll be back, Erik,” she assured me, “don’t worry.”

The moment she left the room, I closed my eyes and drifted off.

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