His Sister's Hot Friend Fucks Him

This is purely a work of fiction. Any resemblances to real life people or events are entirely coincidental and unintentional.

My name is Lyle. When all this started I was an 18 years old boy and have spent my entire life living in my older sister Leah's shadow. She's everything I'm not. While Leah is beautiful, out-going and sporty, I've always been scrawny and introverted, and can't remember the last time I went to the gym. She's popular at school but I've always been an outcast. Five years ago, my big sister joined the football team. There, she made a lot of new friends. Often, she would bring them over to hang out at our place, and I didn't mind at all, since they were all friendly and really nice to me. It felt good to be able to talk to other people without stuttering, as my sister's presence really did make me feel much calmer and better about myself, with the way she always reassured me.

She would always protect me from other kids whenever they showed any signs of being mean to me. And I'm eternally grateful for that. I'm in the background, though, whenever my parents discussed her sports achievement with pride. They love me too, but they tell her about how proud they are of her than they say something like that to me. It's not like I minded, though. I was content for my sister to beam happily with pride whenever our parents told her that she did well. Academically she also succeeded greatly, whereas my grades fluctuated between As and Bs through the years.

Her friends were also all very pretty and fit. One of them, Cassandra, was on the football team with her. We actually grew up together with her living next door to us. She's really smart, kind and athletic, with washboard abs and long muscular thighs. Her wavey, long brunette hair fell down to her round, tight ass. To be honest, I've always had a crush on her. The way she smiles warmly at me whenever she's over and asks me how my day was, and did so in a way that clearly showed she genuinely cares about me. This girl is nice to everyone she meets and seemed incapable of even getting irritated by some of the obnoxious jerks who asked her out, one of whom even actually asked her when she would like to suck his dick. She turned him down, just like she does with all the other guys. I would have hit on her, except I was painfully shy and she was clearly way out of my league.

We were together at a pool party in her house. Leah dragged me along, saying that I've spent too much time coped up in my room that week. The girls all welcomed me warmly, telling me to help myself to some drink. I just grabbed some orange juice. They invited me to join them in the swimming pool and I accepted. It wasn't to check them out or anything. I just didn't want to upset anyone by declining or refusing their request. It was embarrassing to put my skinny body on display in front of these beautiful, athletic girls. McKayla teased me lightly, telling me I should bulk up some more if I ever wanted to get a girlfriend. Betty-Ann and Cassandra joined in. Leah tried to defend me but I saw her trying to stifle her laughter.

"Could you please get some lemon juice for us, Lyle?" Miranda asked. I nodded quickly, jumping out of the pool, waddling to the kitchen. Their ribbing of me was making my face flushed red. I couldn't believe they all laughed at that like it was so funny. It's not like I'm pissed at them. I just feel, you know, sensitive when someone brings up my body. I was trying rummaging through the kitchen, looking for the juice, finding it eventually. After pouring it into some glasses, I was heading outside to find them again. As I strode towards the pool, I stopped by the door after hearing something which flummoxed me.

"Your baby brother is so adorable, Leah. I've always had a crush on Lyle, and now that he's 18, I can't wait to fuck him," Cassandra said to my older sister. This shocked me, and it also seemed to shock Leah a great deal as well. "You wouldn't mind, right? I'd hate to end our friendship over this, but I will if I have to. I just need to have Lyle." My big sister stopped sputtering and was now slowly trying to form a coherent sentence to respond with.

"Well, sure I won't mind, I guess. Just don't hurt his feelings, okay? And be gentle too. He's still a virgin, so you'll be deflowering him." Wow. My big sister was just telling her best friend that she could fuck me. Somehow, hearing a pretty, sweet and funny girl I've always secretly been in love with saying that she wants to fuck me made my tiny cock throb madly with arousal, filling up with blood. My dick was rapidly engorging to a full erection, pitching a visible tent in my trunks. I stood there listening to the woman I've always wanted to be with discussing me as though I were a piece of meat, making me increasingly horny. Of course, I hope she'd want to be with me even after she did me, and wouldn't think any less of me when I eagerly spread my legs for her.

McKaylah snickered. She is a short and stocky blonde who often calls me things like dork and loser,despite Leah telling her to be nicer to me. "Yeah, Leah is right. Try to be gentle with him. We all know how powerful those firm legs of yours are. Don't crush his dick either. I want something to fuck once you're done." Wait, so she wants me too?

"No! I'm the only one who gets to fuck that cute little boy. You have to find your own guy. Oh and I'll be gentle with him, Leah. After he's blindfolded and handcuffed to the bed, of course. Then, I'll pop his cherry," she said trivially. The mention of such a thing about to happen to me only caused more blood to rush down from my head and to my, well, um, smaller head, if you know what I mean. I was so freaking hard listening to Cassandra's plan for me. All their other friends were giggling at this, teasing Cassandra for her fierce possessiveness, that only served to turn me on more. I wanted nothing more than to belong to her. Suddenly, it occurred to me that I was gone for way too long and I held the chilly glasses in my hand, one for Miranda and one for Cassandra, and went towards them.

Cassandra smiled warmly at me, smacking my ass after I gave her a glass, tilting her head back to swallow the drink in one gulp. The others were trying not to laugh at my blushing face when she slapped my behind right in front of them, my dear older sister included. McKaylah didn't even bother trying to hide it and let loose a round of boisterous giggling that was quickly succeeded by Leah's and Miranda's, who began to earnestly reveal their amusement at my embarrassment. At least it distracted them from my real source of shame : the boner I was sporting beneath my swim trunks, both at the thought of Cassandra taking me upstairs and fucking me senseless, and the way she casually spanked me with her friends watching on.

As you can imagine, I was getting quite nervous. Here I was, a chaste virgin boy, still pure, but realizing that he was about to be taken and deflowered by a young woman he has always been in love with. Add to that the complication of knowing that everybody else knew about this and I'm really not supposed to. I noticed her folding her arms under large double D breasts, pressing them up, allowing the top of her tits to poke over her pale blue bikinis, causing me erection to become even harder if possible. Her nipples were slightly peeking out on the top.

By now, they all spotted my hard on and were laughing louder than before, bent over and clutching their stomachs. Cassandra just gave me a lascivious smirk, before saying "You can't blame him, ladies. I'm very hot, after all." They nodded in agreement. It's true. The combination of her muscular ass, slender torso and beautiful face that is nicely framed by her long, flowing hair makes her a stunning bombshell. She is sexy and she knows it. Her confidence is actually what turns me on the most about her, more than her perfect body. That and the way she always gives me an affectionate grin. It's now replaced by a salacious smirk that betrays her intention of banging me in her bedroom. She got up from her chair and stood up next to where I was standing.

"Lyle, can you help me with something? I need to carry some stuff from my bedroom but there's too many for me to take myself," she said. Leah was trying hard not to snigger audibly. I blushed down to the nape of my neck, hoping she thought this was due to my own shyness and not because I was in on what she planned to do to me.

"Yeah. Sure!" I said, giving her a smile and following her as she led me towards the staircase. McKaylah was definitely laughing behind me, while Leah muttered something that sounded suspiciously like "She better has a condom. I'm too young to be an aunt." This only made me blush more than I did before. I allowed Cassandra to pull me up the steps, guiding me to where her bedroom was. Before I knew it, she pushed me inside, slamming the door shut behind her. "What are you doing?" I asked, pretending to be ignorant as she walked towards me, eyeing my small body the way a car might after catching the canary.

"I want to fuck you, Lyle," she stated boldly. I was extremely turned on by her cocky smirk as she looked down at my steel hard dock in my swimming trunks. The muscular girl then walked towards me, making me stumble backwards and falling on to the bed as she quickly got on top, laying her hands on each side of my face. She stopped down to place a loving kiss on my forehead, making me feel my face burn with embarrassment at how easily I let her take me to bed. Feeling her affection and love only made me harder with desire for her. "By the time I'm done, you won't be able to walk straight," she promised me, somehow knowing that I've dreamt of her taking me violently.

Cassandra then moved her hand down my skinny stomach towards the trunks I was wearing, sliding down my legs, brushing against my exposed cock as it was bared to her for the first time. She didn't seem turned off at all by how small my penis is, instead choosing to grin with delight at how I reacted to her touch. "Would you mind if I'm on top?" She asked me.

"I'm a virgin, but I know that's how I prefer it," I said, hoping she would be pleased with my submissiveness. My assumption was correct. She just grinned at me, before reaching for something in a bag on her bedside table. She retrieved two pairs of handcuffs from it. Without her having to ask me, I quickly stretch out my hands and legs in a spread-eagled position, letting her secure my wrists and ankles to the bedposts. "You're so hard already," she told me in a condescending tone. Just a few seconds later I found my rock hard dick throbbing inside her warm, wet mouth as her head descended on to my lap, one of her hands cradling my balls while the other rested on my stomach.

"P P Please d don't" I found myself begging. "It's dirty down there." I didn't want her to have to ignore the bad taste and smell just to make me feel good. Her pleasure means a lot more to me. There was no way I'd expect her to be so generous before I made her happy first.

"Don't worry, my love. Your cock is way more delicious than anything I've ever tasted," she said with a smirk that made my face turn bright red, before she attacked me, sliding her lips along my length at an incredible speed, swallowing my entire shaft into her mouth, making me thrash about wildly, unable to control myself. "Tell me when you are close. You'll have to beg me if you want to cum" she warned as the girl came up for some air, before continuing to suck my dick. Hearing her say that only made me more aroused and soon I found myself uncontrollably bucking upwards, loving the control she has over me. At that moment I knew I was hers.

The way her cheeks formed a suction around my small dick as she sucked me so well I was moaning loudly, almost screaming her name as her tongue swirled around my cockhead, her moist lips moving from the tip of my dick down to the base and then sliding up again, making me pulsate inside of her warm mouth.

The sound of her slurping was driving me wild. She licked the underside of my cock crown, using her tongue to swirl around the sensitive knob as she bob her head up and down, faster and harder, making me moan like a true slut as she sucked my cock so damn good. Soon, I found myself close to orgasm. That's when she stopped, feeling my balls beginning to tense up and hearing me give her a warning that I was getting close now. "Please let me cum Cassandra. I need it so bad! I'll do anything you want. Please, just let me cum!" I whimpered, begging for release, then realizing that I won't get it, based on the malevolent gleam in her eyes.My dick was throbbing violently, far harder than it has ever been in my entire life, as she withdrew her lips from around it. The older girl stood up and moved so that her face was next to mine, and smiled before kissing me on each of my eyelids. Her romantic gesture almost made me spray cum everywhere.

"I'm not letting you cum yet," she said with an evil smirk, standing up and walking out of the room, leaving me lying on the bed with tears of frustration, dry fucking the air desperately. I strained against the handcuffs, wanting to make myself cum, but was unable to. Apparently everybody else had relocated to the next room, because I could hear them chatting animatedly. "He's so adorable when he's begging me to let him finish," Cassandra was telling the rest, barely holding in her now familiar laughter. "I swear, you should have seen how much pre cum he leaked. It's like a faucet or something." Everyone was giggling while I laid on my bed, blue balled. "And he was so sweet when he asked me not to suck his dick because 'it's dirty down there.' That one actually got a lot of 'Awws' from her cohort.

"Just tell me you're not just tormenting him for fun. I know I tease him too but he's my brother and I love him," my sister said. She sounded quite adamant about this and I'm glad she's defending me. The rest of them went silent for a minute. I waited eagerly to hear what Cassandra would say and was very happy about it as well.

"Don't worry. I promise I'll take good care of your baby brother," she promised Leah.

Cassandra then walked back into the hallway. I could hear her footsteps approaching. Soon she was inside the room again, with a long piece of cloth. "I'm going to blindfold you," she told me, sending more blood down to my dick. She knows exactly what turns me on. The girl wrapped it around my eyes, and soon I couldn't see a thing, as she got down by my cock again. I felt her hand wrapped around my rod possessively. "This is mine now, darling," she hissed before wrapping her lips around it and sucking again.

Cassandra sucked me even harder than before. "I'm about to cum," I said, expecting her to stop. Instead she sucked faster and soon large ropes of cum erupted from the top of my cock, spraying down her throat in shockingly large amounts. I was astonished at the large amount of semen I'd produced. She lifted her head up after I was done.

"You came without my permission. I'm going to punish you for that." She uncuffed me and removed my blindfold. This was followed by her telling me to bend over her lap. She rubbed my upturned ass gently before beginning to paddle my buttcheeks with her hairbrush, spanking me vigorously 50 times, each one more stinging than the previous. My tender cock began to swell again as it rested on her strong thighs and she took notice of this, as she slammed even harder onto my red, tender cheeks, leaving welts behind on my sensitive skin.

Smack! Smack! Smack! I laid there sobbing pathetically once she's done, ashamed of how hard I became again. "Don't you dare touch yourself when I'm gone. I want you to stay hard for me until I'm back," she ordered, leaving to join my sister and their other friends on a shopping trip. I was left there in my bedroom to my own devices.

Normally, I would have just lubed up my cock and jerked myself off, but she told me to wait for her, so I tried to ignore the massive erection and found something else to occupy my time. I read, watched the TV and even listened to some music, but nothing I did was enough to distract me from my horniness. Several times I thought about just masturbating and then telling her I was a bad boy and asking her to punish me. The reason I didn't do that is because I wanted to save up my cum for when she does fuck me later. Thinking about that was a mistake since it made my erection even harder than it already was and I can hardly move about now.

Six hours later they were all back. When I greeted them at the door, each of the girls looked at me and gave me mischievous grins, which I thought suggested that they probably discussed what Cassandra did and was planning to do to me next. Said girl just kissed me on the cheek and licked the corner of my mouth, allowing me to taste and smell my own cum from earlier. Everyone laughed at how red I immediately turned.

They all gathered around the table in the living room. "Get us some wine," Cassandra said. I quickly did what she asked, bringing over a bottle and pouring it out for them. They ordered me around, telling me to fetch all sorts of stuff and then carrying on with their conversations. I just wandered about, doing what they wanted me to and staying quiet, only speaking occasionally. Eventually, Cassandra told me "I'll take you to your bedroom now Lyle. You're staying here tonight." All the other girls quickly started laughing at my expression. I could feel my jaw hit the floor at her nonchalance. She grabbed my hand, gingerly leading me to the bottom of the stairs, leading me up for the second time that day.

Once we arrived at the room, I realized it was hers, after having been in there once already. "So you want me to sleep in your bedroom tonight?" I asked her meekly, looking down at my feet so she couldn't see how madly I was blushing at that moment. Cassandra placed her finger under my chin, tilting it up so I could look at her, and she could stare into my eyes. Her intense gaze made me flush further. I closed my eyes coyly as she stood up to place fluttering kisses on each of my eyelids, her arms cocooning me in a warm embrace, making me feel safe as she held me so tightly and yet with so much care.

Before I was able to protest, she had one arm under my knees lifting me up while the one supported my back, carrying me to her bed, where she gently laid me down. I propped myself up, and looked away coquettishly as she attacked my cheeks and necks with lingering kisses, and removed my shirt and pants. Soon I was sitting on the mattress in nothing more than my boxers. I quickly slid it down my trembling legs in excitement as she took off her own dress, revealing her toned, curvaceous body to me, and placed one of her 38DD breasts at my face. "Suck my nipple, bitch," she ordered menacingly. I quickly did what she asked, taking her nub into my lips, licking with my tongue, sucking eagerly while she began to moan in pleasure, moving her long hair behind and over one shoulder. Cassandra smirked, looking at how I was whimpering as she began to wrap her long fingers around my hard shaft, giving me caresses that send tingles of pleasure up my spine. The feeling of her hand pumping my cock was way better than anytime I ever masturbated on my own. She squeezed and stroked me, swiping her tongue on the underside of my cock crown, using my precum to lubricate her shuttling fist.

Seconds later I found myself on my back, looking up at her athletic frame, my gaze dropping from her faint six pack abs down to the beautiful pussy that lies between her thick thighs. Wordlessly, I stretched one hand to each bedpost next to my head, waiting excitedly while she handcuffed me there, rendering me helpless, unable to escape. She smirked at me ogling her and patted my head proudly at my obedience, before placing her hip over my pelvis.