Lessons Ch. 01

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I fuck my best friends brother.
3.1k words
4.61
44.5k
39

Part 1 of the 3 part series

Updated 06/11/2023
Created 02/01/2022
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"I've never felt so foolish." I wrap my arms around myself and hold back tears. Laine offers me a comforting smile as she squeezes more chocolate syrup into my shake while I sit on the kitchen island and mope.

"Who made you feel foolish, Dot?" A familiar deep voice rumbles from the doorway. I feel my cheeks crimson and see Hayden leaning in the door, looking ready to fight whoever had done me wrong.

He's so stealthy for his size, filling up the door frame with his muscles and width. "N- No, no one -Nothing."

"Easton said Dottie ``is not experienced enough and kicked her out of his car." Laine talks over me, filling her big brother in. She rages for me, adding a giant spoonful of peanut butter to my shake and an extra liberal amount of caramel vodka and Irish cream. "Isn't that supposed to be like every guy's fantasy, deflowering a cute little virgin?"

"It's a common one." He waves her off. "Like he made you walk home?" He asks, placing both hands on either side of me, leaning over me as he waits for my answer.

I shrug, already embarrassed that he knows how inexperienced I am now. Twenty-one and only been kissed and slightly fingered. If there was one thing Hayden was known for, it was his amount of experience. He'd laugh in my face and make me walk home too.

"Yes!" Laine slams her hand on the counter, turning back to the milkshake, still grumbling as she turns on the blender.

Hayden raises his eyebrows waiting for the whole story. It's not like he hasn't known how pathetic you are, thanks to Laine's big mouth and my lack of social life. I sigh and tell him about Easton trying to get me to talk dirty to him while he tried to finger me, how I felt uncomfortable and how it hurt a little, how Easton laughed in my face when I told him I was a virgin and then opened his car door and told me to come back when I had more experience before driving away. I could have walked five minutes to my parent's house, but they are the save yourself for marriage type, and I didn't want to hear about it, so I walked twenty minutes to the apartment I shared with Laine and Hayden. By the time I've filled Hayden in, I'm on my second alcoholic shake that's even stronger than the first one.

"You didn't do anything wrong, you know. He's the jackass for not making you comfortable or taking time to learn what you both want." Hayden smiles down at me. Even with me sitting on the counter, he's taller than me. Not that it takes much. I feel my cheeks growing warm at him telling me what to do, bent over me like he's about to devour me. "Show's a real lack of skill, consideration, and imagination." I duck my head and nod, unable to meet his brown eyes anymore. Pull yourself together.

"Unfortunately, I have to meet two clients at the gym," Laine says. She's a personal trainer at a 24/7 fitness gym. Luckily she gets to make up her hours, but she occasionally takes late clients, usually when saving up for another tattoo. "I just came straight home when I got your call." She pats my leg as she passes me. "Give me like three hours, and then we can have a home spa weekend." She pulls on a zip-up and turns to her brother. "You better answer to her every beck and call. My girl needs spoils." Hayden gives her a salute and winks at me, causing my tummy to summersault.

"I'll be fine." I try to slide off the counter, but Hayden blocks me again.

"You deserve better than him, Dottie," Hayden grumbles. "Your first time should be with someone who knows what they're doing and cares about you, not some stupid frat boy who will pump into you twice and leave you hanging. You should at least know you deserve better than that."

I don't know what to say to defend myself and just shrug. It wasn't about deserving as much as scratching an itch with a semi-cute face and sexy body. "I didn't know anyone willing with all those qualifications."

Hayden steps closer, and I can feel the heat from his body as he leans over me. "We both know I'm more than qualified to give you some lessons." He whispers in my ear, and I can feel his warm breath on my neck. Does this mean he cares about me?

I shiver at his words. It's not that I've never thought about running to Hayden to scratch my itch. It's more that I figured he would laugh in my face about being boring. "You're more-'' He cuts off my squeak, grabbing my throat below my jaw and crushing his mouth to mine. He steadies me by grabbing my arm and holding me in place while pushing his tongue past my teeth. He angles my face for him to take the most advantage of me, tangling his tongue with mine while I cling to him.

He tastes like mint and cola and knowing that makes my stomach flip. His stubble pricks my cheeks and chin while he explores my mouth, sucking my tongue until I moan into him. His hand drops from my arm to my ass, and my heart lurches in excitement and surprise. "I've wanted to feel this ass for a long time." He mutters, dropping his other hand to my ass and giving me another squeeze as he pulls me to the edge of the counter. A long time? He hovers his lips over mine, waiting for me to get impatient and meet him the rest of the way.

I sigh into him and kiss him back hungrily, enjoying this more than I had tried with Easton. I wrap my arms around his neck, loving how he feels pressed against me. Hayden leans into me, spreading my legs with his hips. He slides his hand around my crotch, and I whimper when he applies pressure.

I can feel his warm breath on my cheek as he chuckles victoriously. "So excited, already." He breaks away to nibble my bottom lip, his stubble scratching me as he rubs his nose against mine. "Lesson one." He breaths. "Dirty talk one-oh-one. Tell me how wet you are right now." He murmurs against my lips. His voice is so deep that I can feel it rumble through my chest, making me feel weaker.

My cheeks turn crimson as I meet his dark eyes, waiting for my answer. I nod at him.

"Use your words." He grabs my hand, clinging to the front of his shirt, and lowers it to the top of my jeans, pushing it past my waist. "Feel."

I take a deep breath, trying to gain some bravery. I cup my pussy over my cotton panties and feel they're soaked. "So-" My voice cracks. I lick my lips, watch his eyes follow the movement, and feel my blood pressure rise when I realize he wants me. "So wet." I breathe. "I'm so wet."

"Show and tell." I pull my hand out of my pants and hold it up for him to inspect. I am mesmerized as he slowly brings my glistening fingers to his mouth and sucks them clean. "You're right. You are so wet and so fucking sweet." He pushes his hand into my pants, pushing my panties to the side and running his fingertips up and down my slit. "Fuck." He groans. He finds my clit and starts rubbing in fast, tight circles applying the perfect pressure.

I've fingered myself many times, but it never felt as good as this. "Hayden." I gasp, surprised by how fast and strong my orgasm is building. "Oh, my fuck." I'm panting against his lips, watching his eyes darken before pressing his lips to mine again. "Tell me how good it feels."

I squeeze my eyes shut, and try not to claw his arm off. I can't hold my hips still while he runs his thick, calloused fingers over me. "A- Amazing. It feels fucking amazing." I teeter on the edge of cumming, so close yet not close enough.

"Tell me what else you need."

I shake my head, unsure what I need, just that this isn't enough. "More." I plead. He spears two fingers inside of me, and I groan. "Yes." His fingers are thick and stretch me out deliciously. I whimper when he curls them forward and presses his thumb to my clit. I tangle my fingers in his hair, needing him closer. "Oh, god."

"Are you so close, Dottie?"

I nod, leaning my forehead against his with a moan. "Yes." I manage to rasp between gasps.

"Let me feel you cum." Sparks fly behind my eyes, and all I can do is cling to him while he keeps up the motions, pushing me higher and not letting me come down. "I could watch you come all night." He mutters against my lips, still holding me upright.

I nuzzle into his broad chest, feeling both drained and energized. My pulse is beating throughout my body as I try to focus on breathing. "What's lesson two?" I demand, still clinging to him.

He smirks before picking me up. I squeal, afraid I'm too big to carry, but he doesn't even struggle as he brings me to his room. I've never been here before, and I'm surprised at how clean and minty it smells. He sets me on his bed and crawls up after me. "Lesson two requires the loss of these." He meets my eyes, waiting for confirmation before he starts unhooking my pants. I watch as he peels them off my legs, watching me the whole time like he's afraid I will pull them back up. He looks so fucking sexy eyeing me like that; so hungry. I swallow and squirm on his bed. "Take off your shirt."

I sit up and grab the hem of my shirt, suddenly anxious. I've never felt so exposed. I take a deep breath and pull my shirt over my head in one swoop. Hayden crawls over me and cradles me against him before pecking me on the forehead. "Will you take off yours?"

He eyes me excitedly. "Do you want to do it?" He sits on the edge of his bed and pulls me so I'm straddling his lap once I give him a shy nod. I reach for the edge of his shirt and am surprised at how empowering it feels to strip someone else; how in control I feel. I pull his shirt up, slowly uncovering his hard stomach and soft pecs as I go. He raises his arms for me, wrapping them back around me once they're free. "So sexy." He kisses me softly before laying me back down on his bed.

He places wet kisses down my neck, chest, and stomach, stopping at the top of my panties and questioning me with a look. He pulls them down my legs and kisses his way back up to my center, smirking as I squirm with anticipation. Hayden hooks his arms under my thighs and holds them open wide. I push myself up so I can watch him. He gives my slit a slow, teasing lick, and I gasp at how devious it feels for his head to be there with his tongue parting my folds. "Oh." I sigh breathlessly as he flicks the tip of his tongue over my clit. This is what I've been missing.

Hayden gives me a mischievous grin before sucking my clit into his mouth and swirling his tongue over me. I fall onto the pillows and grab his hair, but he doesn't give up. I can feel the prickle of his stubble against the inside of my thighs and my labia as his tongue dips into my hole. He pins my hips with an arm and slips two fingers inside me while continuing the sweet torture. "Holy fuck." I grab the sheets struggling to stay still.

"Tell me how much you love me playing with your pussy."

"I wish I had come to you so much sooner." I groan.

"You like my fingers inside you?" He demands as he curls them forward. I moan a yes as I wrap my legs around his shoulders. "You like when I eat this pretty pussy?" He licks up my slit again.

"So fucking much." He adds a third finger, and I squeeze my eyes shut. I can feel my legs start to shake, and I know when I cum it's going to be huge. "Hayden." I reach for him feeling excited and anxious.

"I'm right here, pretty girl." He slips his hand into mine and swirls his tongue back over me. My back arches off the bed, and I feel my legs pull him in tighter to me against my own accord. He doesn't stop even when I pull his hair harder than I mean to with my free hand. He sucks my clit until my moans turn into mews, climbs up my body, and crashes his lips to mine.

I can taste my musk on him, which only makes me hungrier. I dig my fingers into his back, needing so much more. "Please don't stop," I beg as he brushes my hair out of my face.

"You want me to fuck you?" I nod and crush my lips back to his, raking my fingers down his chest to the top of his jeans. I find his buckle and start tugging it open. He chuckles at my impatience and sits up so I can see better. I shove his pants and boxers down together and reach for his dick. He grabs my hands and pins them to the pillows as he lays back over me. "I want to focus on you this time." He shimmies the rest of the way out of his pants, nipping my jaw and nuzzling into my neck, ignoring my pout. "If I let you play, I won't last long." He pecks my lips. "I promise next time." He slides a hand under me and unclasps my bra. He sits up and pulls it down my arms.

I feel my cheeks flush as he looks me over. "You're fucking sexy." He palms my breast before twisting my nipple. I look him over shyly, taking in the muscles on his arms and how his broad shoulders and chest connect to his hard stomach, eyeing the trail of hair that starts just above his belly button and turns into a triangular patch where his dick starts. He's long and looks smooth, and I want to know how he feels and tastes. Next time.

He bends forward and runs his tongue over my other nipple. It tickles and makes me squirm against him. He reaches between us and presses his thumb to my clit again. I sigh and grab his arms. "Hayden, please."

"Slow." He huffs and slides two fingers into my wetness. I spread my legs wider. He moans, watching his fingers disappear into me, and adds another. I groan and rotate my hips loving how full I feel and wishing it was his cock filling me up instead. He slides down my body and kisses my labia. "This I could watch forever." He murmurs and curls his fingers forward.

"Fuck me, Hayden." I groan in frustration.

His brown eyes meet mine with a smirk before shoving his fingers into my mouth. I suck them clean, loving how my musk mixes with the saltiness of his skin. He lays back over me, aligning his tip with my entrance. "You're so fucking wet for me." He groans. I wrap my legs around his waist, locking him in place as he pushes into me inch by inch.

"Oh." I sigh as he pushes in all the way. It hurts less than I thought it would but enough that I'm digging my fingers into his shoulders.

"I'm all in your tight little pussy." He is still inside me, holding me close while I adjust to being so full. He cups my cheek and forces me to meet his eyes. "You gotta breathe." He chuckles, and I can feel it reverberate through my chest.

I flush as I take a shaky breath, unaware I had been holding it. I can feel his chest hairs tickling against my breast while he holds himself up, and I try to focus on the warmth against me instead of the pinch of him stretching me out. I nuzzle into his neck while he slowly starts moving. I twist my arms around his neck and hold him closer, afraid it will hurt more. I gasp as I feel every inch of him in my channel as he slides in and out of my hole, amazed at how good he feels. He groans through clenched teeth as he picks up pace. "Your pussy feels perfect."

"Hayden." I groan. He pulls back to look at me. "This is fucking amazing." He chuckles and crushes his mouth to mine. I kiss him back as he crushes me against him and fucks me harder. "You feel so good in me."

He grabs my hips and lifts me so he can ram his cock deeper, and all I can do is cling to his forearms and keep my legs locked around his waist. I can feel a warm pressure growing, and I know I will cum soon. I try to fight it back, not wanting this to end. Hayden presses two fingers to my clit, pinching it between his fingers and pressing in fast circles. I want to beg him to stop, that I don't want to cum yet, but god- I don't want him to stop either. I bite my lip, trying to keep my gyrating hips still. "Fuck." I cry out, feeling my pussy clench around him. He groans and pushes into me, and I feel the warmth filling me up and pushing my climax further.

Hayden collapses on top of me, panting. He nuzzles into my breasts before rolling us over so I'm tucked into his side, and he's on his back. "Are you okay?"

I cling to him, trying to catch my breath. "I feel great." He kisses the top of my head. "Ten out of ten would do it again."

He smirks. "Yeah?" I nod at him. "Me too." He rolls to face me and kisses me slowly before covering us with his blankets.

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6 Comments
MaydaypilotMaydaypilotabout 2 years ago

Wonderfully done. 5 stars from me!

AnonymousAnonymousabout 2 years ago

Nice premise.

But story line seems rushed.

Had she ever seen an erect penis before? We don't know. Had she ever touched one? Again, we don't know. She seems to want to touch and play with his cock. Why not let her do it a little bit? Surely, she'd get excited -- even more excited -- seeing his cock, and playing with it, and enjoying his enjoyment. He could have stopped her before he had an orgasm.

Four stars.

AnonymousAnonymousabout 2 years ago

I’d read you again. I thought it flowed well. Please pleasure us with more.

DG

steeleye11steeleye11about 2 years ago

Right, a quick read and not flawless. Still, it was a nice story and I have seen worse.

AnonymousAnonymousabout 2 years ago

Keep them coming, I bet you are going to be one of favorite writers.

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