2 months ago inno regrets

Taking my clueless friend's cute little sister - Part 1



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Everything in this story is real, though I have had to take some license with the dialogue as remembering exact conversations verbatim is near impossible. I hope you keep an open mind, and I apologize in advance to all the guys who have had their sisters fucked by their friends.


My name is Tyler. I'm your typical outgoing guy, nearing 30 now, and currently single. I've been very lucky in the sense that I have a confident and laid back air about me, and am blessed with charisma that tends to draw people to me. As a result, I've never had trouble attracting women. I'm not trying to sound arrogant or big-headed, but on nights out, I'll often be approached rather than having to make a move myself - that sort of energy. I hit the gym regularly, and stand 6'2" with broad shoulders. While I don't have 6-pack abs, I am strongly built. My hair is dark and close-cropped, and I usually have stubble across a strong jawline. I value intelligence, both in myself and in others, and have never found myself attracted to anyone without brains. I'm a STEM grad and have been very successful in my career so far.

I first met my friend Chris when I was in the 9th grade. We didn't get along, mostly because we were both competitive and played on rival hockey teams. The first six months or so were just a series of arguments and barbed words to try and get one over on the other. Since we had so many classes together, we eventually got over our rivalry, and realized we actually had a lot of similar interests. We started hanging out and spending time around each other's houses, and he became part of our core friend group.

Six years later, Chris and I were at the same university and still close friends. We were partying and going out whenever we weren't stuck in classes or in the library studying. I had already developed a strong dominance kink, and was finding a lot of joy exploring it with the enthusiastic consent of a different pretty girls around campus. My philosophy on dominance was that having a woman submit to you was a gift of trust and willingness to put themselves in a position of intense vulnerability for your mutual benefit, and that gift was something to be cherished. Strong communication and establishing clear boundaries is of utmost importance. There's nothing that gets me going like being able to gently guide and push those boundaries without ever breaking them. I love teaching new partners and helping them discover that trying out sexual submission can be fun and rewarding, and doesn't make them any less strong or independent in other aspects of their lives.

It was a Friday night, and it was my turn in the rotation to host a party. I lived with a couple of band members at the time and the house had a sound-proofed basement where we would host keg parties with live music. Chris showed up fairly early to help get things set up, with his girlfriend and another girl tagging along. I didn't recognize the other girl immediately, but after a second glance, realized with surprise it was Chris' little sister, Chloe.

When I first met Chloe, she was in the 8th grade, 3 years younger than Chris and I. I didn't pay her much attention, except to note that she didn't talk a lot, was a little awkward and stared at me covertly whenever I was visiting with her brother. I always had the sense that she had a crush on me, but I was always dating girls in my own grade. Of course, we all teased Chris about hooking up with Chloe, but that was mostly to get a rise out of him.

Chris greeted me with a fist bump, and told me that Chloe was here because she had graduated high school and had been accepted to our university. He wanted to show her around and let her experience a bit of campus life before moving out there in the fall. I smiled warmly at her and told her I was happy to have her there and that it was a pleasure seeing her again. She smiled back at me nervously and squeaked out a "hi". She had a very cute smile, with white, even teeth, and small dimples appeared on her cheeks when it came out.

Chloe wasn't my usual type. She was very pale, with shortish blonde hair that barely reached her shoulders. Her features were delicate. Pixieish is probably the best way to describe her, with wide, icy blue eyes. She was about 5'0 tall and skinny with few curves to speak of, though I did notice (in the way guys do) that she had a cute little butt and small perky breasts under her tight fitting black shirt and blue jeans. I wouldn't be surprised if she weighed 95 pounds soaking wet. She had an extremely innocent aesthetic and demeanor, but there was also mischief in her smile and eyes.

When the party got into full swing, we had about 40 people there, and played some drinking games. I taught Chloe how to play flip cup, and the drinks seemed to loosen her up. I managed to get her talking and laughing, lightly flirting and teasing her about how her brother was going to have to chase boys off when she moved here. I felt her nervous shell begin to crack as she got comfortable. I realized she was witty and smart, and wanted to become a doctor. She flirted back with me a bit, occasionally touching my arms, and I noticed she tried to keep my attention fixed on her.

We even danced together a little when the band started playing. I enjoyed watching her dance, moving her hips and smiling happily. I found myself guiltily looking over my shoulder to make sure Chris wasn't watching us. If he saw, he didn't seem to care. My mind began to wander about what her smile might look like if I casually asked her to join me upstairs, but I got hit with a wave of guilt. This was my friend's little sister and she probably had little experience with men. At least the 3 year age gap wasn't a show stopper, with me being 21 and her being 18.

As the party went on, Chris continued pounding drinks, and was swaying drunk by the time midnight hit, leaving Chloe to fend for herself. By 1:00 AM, he was sick in the bathroom. His girlfriend left, annoyed at his antics and overconsumption, so I got him set up on the couch upstairs where he promptly passed out. When I came back downstairs, I saw Chloe looking anxious and unhappy, arms folded tightly as a frat bro looking guy was chatting her up. I could immediately tell she was uncomfortable.

"Hey baby, I was looking for you." I said, walking up to them and putting my arm around her slim waist. "Is this guy bothering you?"

The guy glared at me in annoyance, but he was quite a bit smaller than me and backed off quickly, wandering away.

"Thank you Ty... I couldn't figure out how to get away. I think I'm ready to leave." Chloe said. Rather than pulling away once the guy left, she had pulled in closer against me instead. She felt tiny in my arms. I'm not sure if it was the taboo of being a friend's sister, or her just seeming so innocent, or a protective instinct kicking in, but I felt a mix of guilt and lust as I imagined hiking her over my shoulder and carrying her to my room like some sort of Viking conqueror. Or what she might look like splayed out underneath me, my hand gently wrapped around her slim throat. I shook myself back to reality.

"Don't worry about it Chloe. Listen, Chris passed out upstairs. Are you going to go back to his place, or do you want to crash here? You can stay in my room and I'll sleep on the couch."

"Are you sure? That's very kind, but I don't want to put you out. I don't know what Chris did with his keys." she replied hesitantly.

"No trouble. I'll walk you up there."

I took her hand and led her upstairs to my room. I showed her the bed and told her I'd be sleeping on the couch right across from her. I gave her one of my tee-shirts and told her she could sleep in it if she wanted, and then went to the bathroom to get ready for bed myself. I took the opportunity to splash some cold water on my face and to remind myself again how this was a bad idea. I was feeling uneasy about how amped I was that she agreed to stay in my room, even though I genuinely intended to stay on the couch.

When I got back to the bedroom, Chloe was sitting cross-legged on the bed, wearing my shirt. It was so oversized on her it looked a bit like a tent. She smiled up at me, her cheeks a bit flushed.

"I was just thinking, I don't take up a lot of space. We could both sleep in the bed, you won't even notice I'm there." She was speaking quickly, as if she would lose her nerve otherwise. "Unless you don't want to, of course that's ok too." she added with a sly smile.

"I think I'd notice you were there. It'd be hard not to notice a pretty girl in my bed." I said to her with a grin. I sat down beside her. "How much have you had to drink? And how do you think Chris might react to us sharing a bed even if we are just sleeping."

"Only what I had playing flip cup. I'm pretty much dead sober, I'm not much of a drinker. I do like other things though..." She leaned forward and my breath caught in my throat. The neck of my tee had fallen forward, and I could see right down Chloe's shirt. She wasn't wearing anything underneath. I could see her small, perky breasts only slightly shaded by shadow. She moved closer to me. "And I don't think Chris would ever have to know. Or care that we just slept. You know he'll be out cold until noon tomorrow." she whispered, pressing her soft lips against my ear.

She was right about that. Chris was a very late riser, especially after drinking. "We shouldn't..." I started, guiltily.

"Shouldn't what? We're just going to sleep, right?" She rolled away and pulled the covers down, then climbed in and pulled them back up. As she rolled, I caught a glimpse of her cute bare ass just peeking out from under my shirt. She giggled, looking to see how I'd react.

That was the moment I realized that I had drastically overestimated Chloe's innocence. Chris had always claimed she was a goodie two shoes and a prude, but it seemed he was very wrong. This clearly wasn't her first rodeo. I called her a brat as I slid into bed beside her. I pretended to start snoring, and she tickled me. I laughed and took her in my arms, and she snuggled into me.

From that point, it was like a teasing competition to see who would break first. We stared into each other's eyes, our lips nearly touching, feeling each other's breath. We traced each other's bodies over our clothes. I nuzzled her neck and collarbone. I ran my hand around her breasts, down her flat stomach, and to her soft mound, never actually touching her where she wanted it most. Her breath quickened and she let out soft moans. Her dainty hands were on my chest and on my thighs. She rubbed herself against me, tracing her fingertips along the waistband of my boxer-briefs. The guilt was like a rollercoaster, sometimes intense, other times nearly forgotten, but never strong enough to actually stop.

Chloe broke first. Her mouth pressed desperately against mine, and she darted her tongue between my lips, sliding it across my own. Any trace of guilt forgotten, I responded in kind, rolling on top of her and pinning her easily to the mattress, pressing my hard cock between her legs.

"Oooh, I really like that... You're so strong." she murmured. She started absently grinding her pussy against the mass pressing into her as we continued to make out.

"You like being tossed around a little?" I asked, pulling away.

"I haven't really tried. Guys I've been with seem like they're afraid of breaking me... But all signs point to yes." she replied breathlessly.

"How about dirty talk? A bit of degrading?" I pushed her hips down so she couldn't move. I slowly pulled the tee shirt off of her, exposing her slim frame. I admired her perky little tits, capped with hardened, pale pink nipples, barely darker then the surrounding flesh. Her abs were visible on her toned belly. Her pussy was bare except for a tiny strip of blonde fuzz, and was almost as cute as she was.

"Yes... I think so. I'm down to try anything." she groaned.

"That's a good girl. If there's anything you don't like or that's too much, tell me and I'll stop right away." I started kissing down her neck.

"Fuck. Deal."

I took my time exploring her body with my mouth. I flicked my tongue around her nipples, eventually sucking one into my mouth. She encouraged me with soft little mewling noises. I couldn't help wondering at that moment what Chris would do if he knew I had his sweet, naked little sister pinned underneath me while I sucked on her tits. Rather than the guilt I was expecting, instead I got hit with a massive wave of arousal. I felt powerful.

I moved further down, lifting up her hips, licking and kissing her mound, running my tongue along her smooth outer lips. I flicked my tongue across the skin between her pussy and her ass and she gasped. She grabbed my hair and pushed her hips up into my face. I pinned her back down easily, pushing her knees up into her chest and splaying her legs.

"Tell me you need it." I ordered her, nibbling her inner thighs. I always loved a bit of denial and begging.

"I need it. Please."

"What will you do to earn it?"

"Anything you want Tyler, please." she whined.

"Let me use your body just how I like it, any time I want?" I asked lazily, reaching up to squeeze her breasts.


"Treat you like my little toy?"

"Ugh. Fuck yes! Please, I've wanted this for so long."

"For so long, huh? You're a bad girl lusting after your brother's friend like that. Tell me about one of your fantasies and then maybe I'll taste you."

She made one more failed attempt to push my head down, but I just ran my tongue up her outer lips instead. "You're the worst!" she groaned. She lay silent for a moment, then started to shake a bit with repressed laughter. "Ok, this is kind of embarrassing. But back when you used to sleep over at our house in high school, I used to fantasize about you sneaking into my room after everyone was asleep and having your way with me. Or even sneaking down to the basement where you guys slept and giving you a blowjob, and both of us having to be so quiet so we didn't get caught. God, I got off to that one so many times."

I looked up at her, mouth slightly open in surprise. I hadn't meant a fantasy specifically about me. She looked right back at me, raising one eyebrow. "You asked!" she pointed out.

"I wish you had." I finally answered. "You aren't what I expected, Chloe. Want to try a little edging?" She nodded eagerly.

I finally gave in to her, running my tongue between the folds of her lips, up to the swollen nub of her clit. I pressed my nose into her mound and began gently flicking my tongue against her. She gasped in relief at finally being touched. She was soaking wet, and tasted clean, musky and slightly bittersweet. I swirled my tongue in slow, soft circles around her clit, and started gently sliding one finger in and out of her. She was so tight. I kept up a constant pressure and speed with my tongue, finding her g-spot with my finger tip and lightly pressing on it as I flexed my finger in and out of her. I brought her to the edge of orgasm twice, stopping when she got too close. After the second time, she was shaking with frustration, and quite literally begged me to please let her cum.

I took pity on her. I slid a second finger inside of my friend's little sister, and slowly increased the speed and pressure, building her back up to the edge again for a third time. This time, instead of stopping, I pushed her over it. Chloe's breathing sped up faster and faster, building until I felt her tighten and she let out a loud wail of pleasure. Her body shook, head tossing back and forth, her eyes screwed shut and her toes curling. Her slim thighs squeezed on my neck as her orgasm continued.

When she finished cumming, I stood, pulling off my clothes, and lightly rubbing her body until she came back down to earth. Once her eyes opened, I lifted her up easily and set her down on her knees in front of me as I sat naked on the edge of the bed. She looked around, still dazed.

"That was so intense... but so good." she said in a small voice.

Snapping out of her daze, she locked her blue eyes onto my thick cock, then up into my eyes. Maintaining eye contact, Chloe crawled slowly between my legs and wrapped one hand around the base. Her fingers barely fit around me. She licked a bead of pre-cum from the tip of my swollen cock, and slid the head between her soft lips. I wrapped a hand in her hair. She was good, using her tongue to lick the underside of my head and stroking my shaft with gentle twists as she sucked. I instructed her as she went, making gentle suggestions to improve things, and praising her for the things I did like. Her obvious enthusiasm and direction taking quickly brought the blowjob from good to great as she cradled my balls and noisily slurped away, her head bobbing.

I had her start tonguing my balls and laid my cock, slick with a mix of spit and pre-cum, against her pale face. The juxtaposition between that innocent, fresh face and the lewd thick cock pressed against it drove me wild. Knowing that she was a friend's sister and was supposed to be off-limits made it undeniably hotter for me. She was so eager to please that when I asked her if I could try going deeper, she nodded immediately. I gently pulled her mouth down on my cock, and stopped as soon as I felt her gag and saw her eyes tear up. It wasn't far, but she seemed to be a quick learner, and I knew I'd have ample opportunity to train her up. I let her back up with a little gasp.

"Good girl, Chloe. Who knew Chris' innocent little sister gave such good head. I'm impressed." I praised her.

She pulled my cock out of her mouth and giggled, sticking out her tongue at me, though she looked pleased with herself. "I've had practice. I only look like an angel."

"Oh really." I lifted her to her feet, leaned down to kiss her mouth and then tossed her roughly to the bed. "And how much practice have you had fucking?"

Chloe flushed, looking up at me. "Less." she admitted, sounding a bit nervous. "But I'm hoping to get some practice in tonight."

I pulled a condom out of my sidetable drawer. "I'm on birth control." Chloe said quickly, surprising me. I was about to start lecturing her, but she interrupted. "I've been tested since the last time I had sex. What about you?"

"Two weeks ago. Clean. Are you sure?" I asked. While this wasn't something I'd normally do, and I knew it was a stupid risk, I couldn't seem to help myself. The idea of barebacking my friend's cute little sister while he was passed out on the floor below pushed the taboo feeling even further.

"I've never been so sure." she answered.

I grabbed her under the knees and pulled her towards me. I spread her legs, and began to rub the head of my cock against her slick hole, then slowly pressing it up against her clit, teasing her. She was soaking wet. She looked at me with nervous excitement, her body tense.

"Are you ok?" I asked her, concerned by her look.

"Yeah. Just scared it'll hurt. With my ex it hurt sometimes and you're thicker..." she trailed off.

I leaned down and kissed her again, stroking her hair and cheek reassuringly. "I promise I'll go slow. A lot of guys have no idea how to fuck, especially guys your age. If anything is uncomfortable, you tell me and we'll stop and readjust. I won't be upset, I want your trust, if you're willing to give it to me." I told her honestly. "Plus, I want to be the best you've ever had. Better chance at a repeat performance." I added with a bit of an arrogant smirk.

I felt her relax and she smiled, kissing me again. "Thank you for saying that. I trust you."

I stood back up, and slowly began easing myself inside of Chloe's tight pussy. I held her firmly in place as I entered her, feeling the warm velvet hug of her vaginal walls clamp down on me as I slid ever deeper. I went as slow as I possibly could, letting her adjust to my size, sometimes stopping movement entirely. I used my thumb to gently rub her swollen clit as I penetrated her. She squirmed and gasped underneath me.

I checked in with her throughout, making sure she was ok. She kept telling me it felt intense but incredible, and begged me not to stop. It took a full five minutes before I was buried to the hilt inside of her. I left myself there, caressing her body and continuing to play with her clit. I told her what a good girl she was and how hot she looked, and that I was impressed at how well she was taking me.

I slowly started to pull out, still rubbing her, and to my surprise, I felt her body start shuddering beneath me.

"Oh fuck oh fuck oh fuck, please don't stop." she exclaimed, getting louder and louder. Was she actually about to cum? When I was nearly all the way pulled out, I pressed myself slowly but firmly back in to the base, and Chloe immediately came all over my cock. I stopped rubbing her clit, watching her tremble, her hands gripping the sheets, thoroughly enjoying the feeling of her pussy rhythmically contracting and releasing on my shaft. She finally relaxed again, breathing hard and staring vacantly into space.

"Guess I can cross 'making a girl cum in two strokes' off of my bucket list!" I said to her, laughing.

She smacked my arm, but laughed too. "We're just sleeping, remember? This is probably just a dream."

"If it's just a dream then I can do whatever I want." I told her. "Like this." I wrapped my arms around her slender body, then bent my knees into a squat, lifting her easily into the air. She was so light.

Chloe let out a little shriek of laughter, wrapping her arms around my neck, and her legs resting on my hips. "Now what?"

"Now we find out how much you actually like being tossed around." I hiked her up higher into the air, hooking my arms under her knees. I lowered her body until my cock was lined up to her wet entrance, and pulled her down onto it. She whimpered as I slid back inside her with only a little resistance.

I started slowly again, raising and lowering her entire weight over and over. Within no time she was moaning in pleasure, still gripping to me tightly with her arms and legs. I sped up, faster and faster. I was pistoning my cock in and out of her as I lifted and dropped her, using her like a sex toy.

Chloe's breathing was becoming ragged again and I could feel her body begin to tense as she begged me not to stop. Despite her small size I was tiring quickly. Not wanting to drop her, I tossed her down to the bed, flipped her roughly on to her hands and knees and mounted her doggy style, intent on making her cum again.

The point of view of fucking my friend's little sister from behind was shockingly arousing and is still burned into my brain. She was only about half the width of my body. My hands were bigger than her ass as I gripped it, my cock completely coated in her silky wetness. It was mesmerizing seeing my thick cock disappear and reappear out of that tiny frame, her pussy lips stretching to accommodate and gripping down on me like a vise. It didn't even look like it should be possible. I rubbed my thumb against the small pink bud of her asshole.

I started saying whatever dirty thoughts came into my mind as I railed her, her butt smacking against my hips with each thrust.

"I told you you'd be a good fuck toy for me." I growled into her ear as I pulled her hair back. "How does it feel knowing that little pussy belongs to me now?"

I felt her orgasm building to a crescendo, and knew that my own wasn't far behind. Chloe tried to answer me between breathless cries of pleasure, but I shoved her face down into the pillow, cutting her off.

"Every time I come over to visit your brother, you'll sneak off with me for a quickie. If I come over to your family's house to watch a movie, I'll be fingering you under a blanket right in front of them. If I crash there after a night out, you'll wake me up with your mouth." I snarled at her. They were statements, not questions.

Chloe screamed into the pillow as a huge orgasm ripped through her. Her body trembled like a reed in a hurricane, and it set off my own orgasm. I pulled out of her with a roar, pulsing thick shots of cum all over her ass and lower back as she continued to shake. Dripping with sweat, I watched my load slowly drip down her ass to coat her pink, swollen pussy.

When we had both recovered, I quietly made my way to the bathroom to clean up, and brought her back a couple of warm, damp washcloths. I helped her clean my cum off of her ass and back, and got her back into one of my tee-shirts.

Chloe and I spent the next hour cuddling, kissing and talking. I made sure she was ok with everything that had happened, giving her aftercare. She assured me she had loved every second of it. We even talked about some of the kinkier things she wanted to try next time, and how she'd like me to explore new things I wanted to try out with her in turn. Eventually she yawned, rolled over, and spooned into me.

"That was the best sleep ever." Chloe said with a sleepy laugh. "I'm very glad I'm coming here for school. Night Ty."

My last thoughts before drifting off to sleep was guilt about Chris and the fact that I had absolutely ravaged his little sister. I knew neither of us wanted it to stop, but I resolved to talk to her about it in the morning.

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