How I[30M] wound up fucking my lesbian best friend [26F] [MF]

TLDR Scroll to the divider if you just want to get to the good stuff

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Madison Adams was my best friend.

Not in a secretly-in-love sense. Not in an unresolved-sexual-tension sense. Truly, Maddy and I were friends.

We genuinely enjoyed each other’s company- from speaking only in movie quotes to enjoying insult contests just a bit too much – it was hard to find someone as willing to indulge in our particular brand of stupidity as much as we did. Our friends observing often said they couldn’t figure out if we hated each other or we were actually madly in love.

Which would’ve been reasonable to expect, except for one small detail – Madison Adams was gay.

Over the years we’d become each other’s greatest confidants as girlfriends on both sides came and went. We agonised over unanswered texts from crushes together, commiserated over how women could be so fucking complicated, and picked each other up after particularly nasty breakups.

This is the story of how we ended up fucking each others’ brains out in a beautiful riverside cabin in upstate New York.

–

Because this is a sex story I feel obligated to start with a description of Maddy. She was petite, about 5ft(150cm) tall at most. Years of Brazilian Jiu Jutsu training had left her lithe and toned, with a round bubble butt and perky c-cup breasts. She was often in a sports bra and yoga pants, an outfit that both accentuated and downplayed her assets. Her shoulder length blonde hair was often tied up in a ponytail, and her eyes were a striking blue.

Madison and I met in a small town in the Czech Republic called Mikulov, where I was studying abroad and she was teaching English. I jumped at the chance to talk to the pretty girl at the bar, and she was just happy to take a break from speaking Czech all the time. That she was gay came up pretty much immediately, which would’ve been disappointing if not for the fact that she was simply a hilarious person to talk so. Our senses of humor clicked instantaneously, and we stayed in contact the whole time before returning to the United States.

–

Since Madison lived about 6 hours away by plane, we’d gotten into the habit of going on yearly vacations to hang out and catch up. This year we’d decided on renting a cabin in Ithaca, road tripping up from her apartment in Delaware.

“It’s called having Big Dick Energy, Jin, you should try it.” Madison smirked from the driver’s seat. I hadn’t made a move on a cute girl we spied at a restaurant the night before, and she was still giving me shit.

I rolled my eyes. “Yeah, coming from the girl with a bigger dick than me. You know how weird it is for guys to go up to random girls in public?”

Outside the car, fall was in full swing. Orange swathes of forest were dotted with patches of brilliant, verdant, green. It was a special kind of tranquillity you never got back in California – the kind that felt ethereal and otherworldly.

A stark contrast to the person next to me.

“That’s why they call it BIG DICK ENERGY-mmph! Driving!” She protested as I clamped one hand over her mouth, and then started jabbing me in the ribs.

“Okay, okay, truce!” I yelled, recoiling to my side of the car. “Shiit, like you would know what a big dick looks like.”

“Why, you offering to show me?” She glanced over, arching an eyebrow.

“Just look down, you’ll see one. Massive schlong. Right there. The biggest.” I deadpanned, vaguely gesturing at her crotch.

Still, the exchange left the smallest seed of a thought in my head. Between all of our bickering and sassing, I’d all but completely stopped seeing Maddy as anything other than a good friend. Suddenly, there was a part of my brain that was going: Hey buddy! You’re going on a cabin vacation with a hot girl. Alone.

My imagination, long since tucked away in the deepest recesses of my mind, slowly but surely began to unwind and stretch. It’d been such a long time since I’d actively checked her out, but I started catching myself stealing glances at her throughout the drive.

Madison’s outfit, as usual, was a small white t-shirt and jeans. Her blonde hair hung messily by her shoulders, and her ice blue eyes were fixed on the road. I’d always known it, and I was usually too busy flaming her to consciously acknowledge it, but I couldn’t help but admire how pretty she actually was. Her black bra was visible through her shirt, and I found myself imagining what was underneath. What it would be like to slide my fingers under her bra straps and let them fall off her shoulders-

“What?” She was looking at me through the side of her eyes.

“Nothing,” I quickly said, trying to act as nonchalant as possible. “Fuck you.”

“Awww. Fuck you too.”

–

When we got to the cabin it was business as usual. We unloaded supplies from the Jeep, talked shit, claimed our individual rooms, talked some more shit, and settled in for the night, meeting in the living room for some TV.

“Everything set up?” Maddy asked as she wandered into the living room from the shower, a towel over her shoulders. Her t-shirt hung over her shorts, and I tried in vain not to notice that she wasn’t wearing a bra.

I was in trouble.

I was just about done fiddling with the TV – a YouTube playlist of UFC’s best knockouts. As we were both avid martial artists, it’d become customary for us to watch fights on Youtube and collectively cheer and cringe over videos of people grievously injuring one another.

Maddy crashed hard on the opposite end of the couch, wordlessly resting her legs in my lap.

“Almost – wow rude- almost done,” I replied..

I hit play and settled into the couch. For some reason, watching someone repeatedly eat a closed fist to the face wasn’t quite doing it for me today. I found myself increasingly restless, sneaking glances at Maddy and trying to read her expression. She looked oddly impassive – she was smirking and chuckling at the appropriate moments, but was it my imagination or did she also seem…distracted somehow?

“Hey, do you want to cuddle?”

The sudden question hit me like a lightning bolt. As I internally struggled to maintain my composure and not scream “OF COURSE”, my autopilot for smartass responses took over.

“I don’t know man, that’s pretty gay-” I started, right as the edge of a spinning couch pillow connected with my skull. The impact sent me briefly careening over the edge of the couch. Damn that woman had an arm.

“Fucking knew you were going to say that,” Maddy glowered, a passing look of annoyance on her face. Since when did she look so cute?

“Alright alright,” I raised my hands in defeat, “cheap shot, sorry.” I opened my arms and turned to face her.

“Still want that cuddle?”

“You’re lucky you’re cute,” Maddy said. She scooted over on the couch, turned her back and leaned back onto me.

What did she just say?

For the first time, I didn’t have a response. I just rested my arms around her and tried to pretend to get back into what was playing on TV.

“Ooh, spinning heel hook,” Maddy piped up. “Isn’t that your signature?”

“Uh-huh.” I responded. My mind was miles away. Or rather, it was fixated on something much closer. Madison’s body was pressed against mine, and I acutely felt every movement she made and every breath she took. My hands were resting on her stomach, with her breasts pressing against my forearms. With our skin separated only by the thin fabric of her T-shirt, my mind was starting to race. It didn’t help that from my vantage point, I could see straight down her shirt. Her areolae were barely visible, and her nipples strained against her small white t-shirt. My eyes kept tracing their way down the curves of her soft skin, watching her chest rise and fall with each breath. Freshly showered, she smelled faintly of lavender. It was driving me crazy.

She began absently stroking my hands, which sent tingles rocketing through my body. God fucking damn it, Maddy. Just because you don’t like boys it doesn’t mean I don’t like girls! I could control where I looked and where my hands went, but my rapidly burgeoning erection had a mind of its own, and it was beginning to press into the small of her back. I prayed she wouldn’t notice, but she was lying in between my legs. If she was paying as much attention as I was, she’d no doubt felt it by now. Still, she hadn’t said anything yet.

Wait. We’d both been quiet for the last 5 minutes.

Normally, we’d be whooping and jeering non-stop at the television, but she hadn’t so much as chuckled. Had she noticed that I was turned on? Was she frozen in terror? Disgust? She’d made it pretty clear she was into women. Did I just fuck up our friendship?

“Hey.”

Fuuuuck. My mind slammed into emergency mode. Was there anything I could say to salvage this? I was racking my mind for stupid jokes to defuse the situation, anything to stop the incoming speech that I’d come to know so well from other women:

“Hey, I think you got the wrong idea-”

“Hey, sorry if I led you on but-”

But I was coming up empty. All I could do now was take the rejection in stride. Wait, rejection? I hadn’t even done anything yet!

“I think I’m going to go to bed.” Madison sighed, pushing herself upright. It was 915pm.

“Yeah good call. Brutal drive today. I’m pretty out of it too,” I felt dazed. Disoriented.

Maddy didn’t answer. Instead, she got up and went back to her room, softly shutting the door behind her.

Did I do something wrong?

The rest of the night I replayed the events on the couch over and over, but outside of getting turned on, I couldn’t find any reason for Maddy to be mad at me. Maybe she just decided cuddling was inappropriate. It’s not like I had much to apologise for anyway; what was I going to say?

“Sorry I got a boner when we were cuddling! To be fair you were stroking my hands and you weren’t wearing a bra and you’re really hot.”

Whatever. It was for the best.

—-SEXY STUFF STARTS HERE—–

Thankfully, the second day went right back to normal – filled with the usual banter as we compared sexual exploits, bitched about exes, and made each other laugh. In the chilly autumn wind, we were quick to take advantage of the hot tub, where we spent most of the day drinking beers and staring out at the rolling hills bathed in the crimson and gold tones of Fall.

“So. You roll up to the club. There’s a babe sitting at the bar. What do you do?” Madison propped her elbows on the edge of the tub as she leaned back, beer in hand.

“A ‘babe’? What is this, the 90s?”

“Shut up. Stop stalling. Babe. Bar. What’s your strategy? Besides just letting them go like last time.”

“A. Fuck you. And B. Trying to steal pointers from the master, huh?” I grinned. “Well, I’d probably go up to her and say ‘Shaken or stirred?’”

“Oooh,” she cooed, “you gonna James Bond her?”

“No I’m not gonna James Bond her, you jackass. I don’t even go clubbing.” I took another swig from my can and winced. Maddy always bought such shitty beer.

“Amateur. You know what your problem is?” she grinned. “Your problem is you don’t have a pair of these babies.”

She stood up and placed her hands on either side of my head, leaning down to give me a front row seat to her very generous cleavage. Her black bikini strained against her breasts, and I could see her nipples poking through the thin fabric. It was all I could do to keep a straight face.

“Your plan is to show her titties?” I deadpanned. “How do you know she’s even, you know, -”

“Interested?” I looked up to see a smirk on her face. “Well that depends,” she purred, bringing her face level with mine. “On the look on her face.”

I didn’t stand a chance.

Before I knew what I was doing I sat up, cupped her face with my hands, and leaned in for a kiss. She reciprocated immediately, parting my lips gently with her tongue as she straddled me, grinding her ass on my erection.

My hands slowly travelled up her back, gently pulling at the string of her bikini top as we continued to make out. Her top fell away, and it was all I could do to not ravage her right there. I cupped her breasts with my hands, rolling my thumbs over her pink nipples as she moaned lightly into my mouth. I kept my hands moving, exploring every exposed inch of her skin and feeling her body tense as I glided my hands over her belly, her hips, her back, taking mental notes whenever her breath caught or a moan escaped her lips.

“Mm…keep doing that,” she breathed. My fingers snuck under her swimsuit bottoms as I ran my hands over her ass and pulled her tightly onto my crotch.

“Bed?” She nodded, and we got out of the hot tub, haphazardly drying off as I grabbed her and led her to the bedroom, throwing her on the bed. I pulled off the rest of her swimsuit and began kissing my way up her thighs, hands running over her stomach and tits.

Her body twitched as my tongue grazed her clit. Making sure to give all of her pussy equal attention, I began swirling my tongue around her labia and her opening. Putting pressure with the tip of my tongue, I darted my tongue into her and licked upwards to her clit, feeling her back arch with anticipation. But each time before I got to it, I would change directions and go back to tonguing her labia, gently tongue fucking her.

“You fucking tease.” she panted. “Just- ah!”

I cut her off by fully enveloping her clit in my mouth, feeling her involuntarily buck beneath me. So that was what she liked. My tongue flicked her clit as my lips gently rolled her womanhood in my mouth. Her pussy got wetter and wetter, and I pushed my mouth hard onto her as I felt the juices flow.

“Fuck. Jin. I’m close.”

Moving my tongue in tandem with the rolling and bucking of her body, I heard her moans get louder as her chest heaved in pleasure. Finally, she grabbed onto my head with both hands as she let out a shuddering moan.

Watching the orgasm pass through her, I paused, climbing up to put my face closer to hers.

“You good?”

“Yeah. Just don’t fall in love with me, okay?”

“Maddy, you have no idea how long I’ve been in love with you.” I grinned, pelvis grinding into hers. I watched as her cheeks flushed and heard her sigh in pleasure.

“Oh shut the fuck up, Jin.” Madison breathed, punching me square in the chest.

I seized both wrists, pinning them above her head as I brought my lips close to hers. I felt her hot breath on my cheek.

“Make me.” I whispered.

She didn’t respond. Motioning for me to release her hands, she gently grabbed my chin and turned my face toward hers. Her brilliant blue eyes bored into mine, her naked chest gently rising and falling with each breath.

“Hey. We’re gonna be okay, right?”

“Yeah, I think so.” I smiled. “You okay fucking your best friend?”

“I want nothing else right now. Get this off.” Her toes hooked the elastic band of my swimsuit, and I shimmied out, letting my erection press fully against her body.

I leaned in to kiss her again, working the tip of my penis against the velvety entrance of her sex. We groaned in unison as I pushed into her with the gentlest of pressure, teasing her with just the tip.

“More?”

Her fingers dug into my back as she nodded breathlessly. I rocked back and forth against her, parting her pussy lips excruciatingly slowly as I pushed a little further with each thrust. I watched her breath hitch and catch as my cock slid deeper and deeper, feeling her tight warmth pulse around me. When I was sure she was comfortable I gave one decisive thrust, burying myself completely to the hilt.

Her eyes shot open.

“Fuck, you got my cervix.” she breathed.

“You okay? Want me to go harder?” I asked. She nodded, grabbing my forearms. I interlaced my fingers with hers, pinned her to the bed, and began thrusting in earnest. Pleasure exploded across our bodies as I slid in and out of her at a steady pace, and I leaned in to kiss her neck.

“Touch my clit..”

“So demanding.” I teased, leaning back and thrusting into her from a kneeling position. Running my hands down her body, my thumb found her clit and began drawing circles. The effect was instantaneous. Maddy lifted her pelvis, grinding hard into me as her moans increased in intensity.

Watching her, with her eyes closed, her head pressed back, and her breasts bouncing with each rocking motion, I tried to sear every detail into memory. Her stomach ever so slightly flexed with each thrust, and her pink nipples were hard enough to cut diamonds.

It didn’t take long for another series of shudders to rock through her body.

—-

“So, not that we’re keeping score,” Maddy panted, a glistening sheen of sweat gleaming off her body,

“But I couldn’t help but notice we’re at two for none and I’m starting to feel bad.” Her foot reached out to stroke my cock, her toes gliding over the remnants of our juices clinging to the shaft.

“Well,” I murred, lazily caressing her thigh. “Clearly one of us is more talente-”

“You shut up,” She laughed. “Lie down.”

I maintained a defiantly playful expression as she straddled me and put her hands on my chest.

“Trying to play catch up?” I teased.

She ignored me as she deftly rolled a hairband off her wrist and started tying her hair back. Sliding herself down my legs, she wrapped her fingers around me and began gently stroking the length of my cock.

“I never do this for guys,” she said, glancing at me. The words lacked the punch of our usual barb laced banter. In fact, her expression looked almost…vulnerable? It was heart-stoppingly adorable, and I fought against the urge to scoop her into another kiss.

Then her lips touched the tip of my penis and a surge of pleasure nearly blacked out my vision. Her tongue was quick and adept, moving with a finesse that was both gentle and stimulating as she drew little circles around my glans and pumped my shaft with fervor. Every other stroke she’d swallow my entire length right down to the base, letting her spit pool with precum, sweat, and pussy juices. I barely stifled a groan as I shuddered and squeezed my eyes shut.

“Fuck, Maddy.”

“Don’t hold back. I love hearing you moan.” She was looking at me with those wide eyes again. Not a trace of sass or mischief. All I wanted to do was melt into her.

She resumed working on me, making me cry out in pleasure as I felt my orgasm build. As my body tensed, she doubled down, going faster and harder and making my toes curl. [Overcome with passion], I reached down to grab her chin, working myself free of her grasp and flipping her on her back.

“Jin, what-” was all she got out before I sank my entire shaft into her, pelvic bone grinding against her clit. She cried out loud, burying her head in my chest and pushing back against me. There were no more words as I slammed into her over and over again, just a mix of breathless grunts and moans. My tempo increased as I got closer and closer to orgasm, watching her breasts bounce in tandem to my thrusts while beads of perspiration rolled down her chest. Her eyelids fluttered as her eyes rolled to the back of her head, her arms a vice grip around my back.

“Maddy, where do you want me to-”

“Don’t FUCKING stop!” she cried, wrapping her legs tightly around my midsection as her body began to shudder. My vision tunnelled as I willed myself not to cum. I knew where she was going, and I wanted nothing more than to meet her there. A couple thrusts later I was rewarded with a surge of pleasure as her pussy clamped down on me. She threw her head back, screaming as wave after wave of pleasure shook her petite form. That was more than enough to send me over the edge, and we clutched each other for dear life as our duelling orgasms rolled and surged. I moaned into her chest, giving myself over completely to ecstasy while the world around us ceased to exist.

When we finally recovered, my face still buried in her shoulder, Madison patted me gently on the back.

“You okay there?”

“Yeah,” I panted. “Came super hard.”

“No shit,” she smiled. “Simultaneous orgasm, go us.”

I propped myself up and looked down at her, both of us covered in at least 4 different types of fluids, and couldn’t help but smile. She returned it, a soft smile I’d rarely seen on her, letting out a soft “mm” as I pulled out of her and fell to her side, spooning her gently.

“So…you’re bisexual?”

“Nope. Still gay.” Maddy started, then she sighed. “It’s a spectrum, Jin. It’s not often but yeah, I hook up with guys sometimes.”

“Ahh.” I replied, looking at the back of her head. “Guess it just never came up between us.”

At this Madison eased out of my embrace and turned around.

“Oh no, it has,” she smiled, kissing me lightly. I returned the kiss, gently resting my hand on her ass. She broke contact and looked at me, grinning.

“You’re just a fucking idiot.”

Source: reddit.com/r/gonewildstories/comments/sxl8e2/how_i30m_wound_up_fucking_my_lesbian_best_friend