[MMF] [M]y Best [F]riend’s surprising proposal unearths dormant feelings

One of the most frequent questions I get in response to the stories I’ve shared is something along the lines of “as a bi guy, have you ever had a threesome with a girl involved?” And my answer has always been ‘yes’ and that I haven’t shared it because that story involves a very good friend of mine who is publically pretty shy and sexually reserved and I didn’t know how she’d feel about sharing the story with the internet (The guys that I wrote about were very turned on by the idea and gave instant yesses). When I floated the idea to her recently, she gave me the green light with the caveat that she read it first. When I sent her what I wrote, she responded: “omg, that definitely a turn on, share away ?. Ps let’s get dinner soon and catch up!” . So, this one is for you, Kaitlyn – name changed, but you know who you are ;)

Kaitlyn and I have been friends since the first week I moved to Colorado 6 years ago. At the time, she was dating one of my roommates who was an old college buddy and rendered her completely off limits. Even though I was definitely physically attracted to her, the lack of could-this-be-a-thing sexual tension took any awkwardness out of our conversations and we just grew to enjoy each other’s personalities. My buddy eventually broke up with her and moved away for a job, but by then Kaitlyn had I had grown beyond that connection and our friendship progressed and though we often dated other people we always found time to just hang out and shoot the shit. 

I am completely discreet about the fact that I am bi and no one in my life had ever been privy to my exploits with men… Until one night a couple months ago when Kaitlyn and I were recapping Game of Thrones at her house. Earlier, I had taken a picture of my ass in some new tight underwear and sent to a guy a few towns over who I had been chatting with but hadn’t “met” yet. Sure enough, as Kaitlyn and I were watching TV, my phone pings and I check it automatically. The guy had sent me a dick pic. 

“Ugh, what the fuck?” Kaitlyn gasped at my side. “Jack, did someone just send you a dick pic?” 

My mind raced for a second, this was one of my worst fears realized. What kind of plausible excuse could I give? But as I looked at her, I relaxed, this was one of my best friends in the world and if there was anyone I felt comfortable keeping a secret with it was her. So, I came clean and told her everything. Now, Kaitlyn is pretty conservative sexually, she doesn’t flaunt her body, doesn’t believe in one night stands and I would be shocked if any of her boyfriends has even brushed her asshole with a finger without getting a slap-away, a cold shoulder and subsequent blue balls. Though, she seemed a bit weirded out at the thought of me with a guy, she eventually started firing off questions and getting seemingly more and more intrigued by the unique pleasure I got out of it. Eventually she ran out of questions, gave me a hug and said my secret was safe with her. 

I thought that was the end of it until I got a text from her asking if I would meet her for dinner and that she had something on her mind she wanted to discuss. 

We met for dinner the next night and after some casual conversation, she turned the subject to text she had sent. 

“So, Jack. I’ve been thinking a lot about our conversation the other night.” 

I glanced around the room to see if anyone was a potential eavesdropper. But we were pretty alone. 

“Yeah?”

“Well, I was in bed with Luke [her current boyfriend] and I just kind of blurted out ‘have you ever thought about sex with a guy?'” she blushed. “Honestly, I don’t know why I said it but our conversation was just sort of stuck in my head. 

“What’d he say to that?” I asked, intrigued.

“Well… He said yes, he had. He even very casually admitted that he had exchanged blow jobs with a guy in college.” 

I had only met Luke a couple times, but from my first impressions of him, this answer did not surprise me. He was a very open kind of person. A perfect contrast to Kaitlyn, he was just someone who didn’t really seem bothered by other’s judgement and just kind of confidently lived his choices. 

“Huh” I responded. “And so, why are you telling me this?”

She paused, curling her hair and bighting her lip, looking nervous and though she was considering whether or not to just drop the conversation here. I waited patiently and she finally kind of blurted out:

“Do you want to have a threesome with us?” She stared straight into my eyes a second, waiting for the potential judgement, and then away quickly. 

I was first somewhat dumbstruck and then my heart started to beat quickly. I looked at her in a light that I thought had extinguished years ago. Kaitlyn IS beautiful, she has shoulder length auburn hair and sharp, blue eyes and a wide easy smile that lights up her face. Though she rarely shows it, she has an amazing body. Her favorite hobbies are climbing, hiking and road biking and her legs and ass show it. I started to have conflicting feelings, the thought of any kind of sexual contact with her was both extremely arousing and potentially emotionally devastating. Given how well we got along, If the sex was good, it might push me over the hill from “love” to “in-love” and that could fuck everything up. 

“Jack, please say something.” She pleaded.

“I.. well…” I stammered. “Kaitlyn, what if we…” 

I didn’t know how to voice exactly the question, but she was right on the same page, unsurprisingly. 

“I know, I thought about that too. But maybe it doesn’t have to be a bad thing you know? I mean Luke’s only here for a couple more months and it’d be nice when winter’s over to have someone…” She trailed off. 

I couldn’t believe what I was hearing, I was seeing a completely new side of my friend. Here was a girl who got weirded out by having to kiss a guy in a play, now seemingly proposing a freinds-with-benefits situation to curb her off-season horniness… Then, I came to my senses. What sane guy doesn’t say no to a deeper connection with a beautiful woman he loves, we can face problems if/when they arise… And plus after THAT proposal how would I get the idea of fucking her out of my head without actually doing it. 

“I”m in” I said. And her face lit up. 

…. ….. 

I met Kaitlyn and Luke at her place that Saturday night. They had prepared a dinner and we ate and drank wine awkwardly (at least Kaitlyn and I did, Luke was relaxed and congenial and seemed to be getting a huge kick out of our discomfort).

Finally he stood up and just blurted out: “you two are adorable, come on, it’s just some sex between friends.” When we grinned sheepishly and didn’t respond he just said: “guess I’ll just have to take charge here.” He moved over to Kaitlyn’s chair and leaned in and kissed her neck from behind, running his hands down her shoulders to her breast and cupping her tits. Her eyes closed and her head fell back as she soaked in the pleasure. 

I could feel myself growing hard watching my friend getting sexually aroused and I reached down to adjust in my pants. Luke took a hold of Kaitlyn’s hand and guided it over to my pants placing it on my crotch and her small hands instinctively started rubbing my hardening cock through my jeans. As she felt the length her eyes opened and glanced at me in pleasure and surprise.

After a couple minutes fondling, Kaitlyn – seemingly galvanized by the lust growing inside her – took us both by the hand and led us into the bedroom. They had prepared and the room was dimmly lit and soft music was playing on the speakers. When we got close to the bed she turned and kissed Luke deeply, leaving me standing behind feeling somewhat awkward. 

Then Luke pulled away and turned her around, pushing her slightly towards me. We locked eyes and for a moment I just stared into my friend’s beautiful eyes, knowing that we were stepping into an exciting but potentially emotionally fraught future. And then I took her in my arms and kissed her, the world dissolved and all I could feel was the soft wetness of her lips on mine and her strong, smooth back in my hands, reacting in pleasure to my touch. 

She was sanwhiched between us and Luke’s hands slid down her stomach, pulled up her dress and she softly bit my lip and gasped as his hands found her pussy. I stopped kissing her and pulled my shirt over my head. Luke was kissing Kaitlyn’s neck as she was rocking in his grasp, eyes closed and mouth open in pleasure, grinding her ass on his crotch. I reached in and pulled the shoulder strap of her dress down her arms and let it fall to her waist, revealing her amazing tits.

Kaitlyn is a solid C cup and though I had caught myself looking at her chest before, I had never thought i would get to experience them in all their glory. I leaned in and kissed her chest, my cheeks brushing in-between her soft round breasts. I worked my tongue around her small, perky nipples loving the sound of her moan and gasp as she is pleasured by two men. She gave a sharp intake of breath and her hips bucked quickly and she softly pushed me away and then pulled Luke’s hands from her dripping wet pussy. 

She reached over and undid Luke’s pants and let them drop to the floor. She went to her knees and kisses his hard 6″ cock. He groans in pleasure, eyes relaxing he beckoned me forward. As Kaitlyn started to take his cock deeper in her mouth, he undid my pants and using his strong hands, pulled out my cock and started to jerk me off slowly, his hands tenderly gripping the tip of my cock and working it in slow circles. 

Kaitlyn pulled away from Luke and turned to me. She took my 7″ cock in her hand and stared up at me, her beautiful blue eyes full of lust and sexual energy. Then she took me into her warm wet mouth, staring into my eyes as her soft lips ran up and down the shaft of my cock. 

I reaches around her and took Luke’s dick into my hands. He is a bit smaller than me, but also a bit thicker and while mine is smooth firm, his is a bit rougher and more leathery. The feeling of a hard cock in my hands while a beautiful woman sucks me off drove me wild and I got a strong urge to get Luke’s hard cock in my mouth. I sat on the bed and pulled Luke’s hips towards me as Kaitlyn started licking up and down my penis flicking her tongue at the tip. I could never have believed she was this sexual, I was experiencing a whole new side of her. 

Determined not to be outdone I took the fullness of Luke’s cock all the way into my mouth and his hips thrust at the sudden pleasure and I could feel his soft tip hit the back of my throat as I suppressed a gag. Luke put his hand on my head and leaned back, working my head on his shaft at the pace he liked, I relaxed my jaw and took it. 

Kaitlyn pulled back and watched, slowly stroking my dick that was still wet with her spit, I could tell by the intensity of her grip and movement that she was definitely getting hot at the sight of me sucking her boyfriend. 

I pulled back and gasped as Luke’s dripping cock slid out of my mouth. Kaitlyn stood up and kissed Luke’s chest as he pulled her dress over her head. 

“Lay back on the bed” he said to me, and I obeyed. He turned Kaitlyn around, softly pushing her down and bending her over until her face was back at my dick. She took me in her hand as Luke entered her wet pussy slowly from behind. I look down and see her face scruntch up in concentration as she’s filled with the pleasure of his cock entering her. It’s a look I’d never thought I’d see on her beautiful face. 

She gripped my dick like a lifeline as Luke started to pick up the pace. As she got used to the rythem of his pumping she opened her eyes and mouth and started greedily sucking my cock taking breaks to gasp and moan as Luke changed his motions in and out of her. He started grunting and his pace become more regular, I could see the pleasure of his thrusts rippling up her body, feeling her hot breath on my wet cock as she moaned in my crotch. Luke went stiff and gave one final big thrust and then collapsed on the bed next to us, pulling off his cum filled condom. 

“That was amazing” he breathed, drenched in sweat. “I’m gonna hit the shower.” He patted her on the ass and walked into the bathroom. As he disappeared behind the door and we heard the shower head turn on, Kaitlyn climbed up next to me and put her arms around me, nesting her head in my shoulder. We lay for a minute just relaxing into each other’s bodies, me taking in the sweet scent of her silky auburn hair. 

She turned and looked at me. “You didn’t cum” she said. 

I looked back. “neither did you” and smiled. 

“How do you know?” She smirked. 

I could tell from her expression and body as Luke had fucked her, that, though, she might enjoy his company and personality, he wasn’t necessarily as attentive  to her pleasure as he was his own. 

In response, I lifted up her chin and kissed her deeply, feeling her body open up against me, her hips grinding into mine, her back arching and her chest rising and falling. We twisted on the bed so that I lay on top of her, my still hard cock grinding slowly against her soft wet mound. My shaft slowly rubbing her clit as my hips worked back and forth. She broke the kiss and gasped, breathing harder and harder into my ear. 

I positioned my cock at the opening of her pussy and paused, pushing up and looking deep into her eyes. And I knew there was going to be real complications in the near future, her eyes looked at me with a loving and a longing I had scarce seen before. She bit her lip slyly and pushed her hips forward and moaned as the tip of my cock entered her. I wasn’t wearing a condom and her warm wet pussy felt amazing around my raw cock. I looked back into her eyes and saw the trust I felt in her reflected back in her eyes.

“Are you…” I breathed, full of pleasure.

She nodded, needing me to go further. “You?”

“Yeah.” I moaned and I pushed forward. Feeling her pussy flex and react as my cock slowly filled her up. When I was all the way in, she arched her back, closed her eyes and moaned, deep in pleasure. I pushed myself on the bed and watched her amazing tits rise and fall with the heavy breathing in her chest. She gripped the sheets and bit her lip as I started to slowly fuck her, my cock finding points of pleasure within her pussy and focusing on those areas as I lustily took in the sight of Kaitlyn’s growing pleasure. 

She reached up and raked her fingers across my back as a tingling feeling flooded through my crotch, I could feel her pussy pulsating and heating up around my cock and knew she was close, I concentrated hard on not cumming as I repeatedly found her pleasure spot. She gripped me tight and let out a series of gasps and moans as her back arched and her hips bucked up and shuddered. As she collapsed back down, the sight of my best friend cumming in pleasure on my cock pushed me over the edge, I pulled off and in one jerk was spraying cum all over the both of us us. 

Kaitlyn cuddled up in my arms and closed her eyes breathing softly but every now and then involuntarily shuddering in my embrace. Then she looked up and kissed me on the cheek. 

We heard the shower turn off in the other room and Luke pull the curtain back. 

“Guess we should clean up and see about that dessert.” I said. Smiling. 

She let out a laugh and looked at me lovingly. Kissing me again. 

…. ….

After that night, she asked for a little space and I consented. We’ve both been extremely busy and she is currently back home visiting family, but Luke has since moved on from his seasonal life in our town and I am interested to see where Kaitlyn and I stand when she returns. She is the first girl I’ve ever had sex with that knows about my bisexual leanings and it’s exciting to see how things might progress. I’ll be sure to update (with her concent of course) if you all enjoyed. ;)

Source: reddit.com/r/gonewildstories/comments/bkrz7y/mmf_my_best_friends_surprising_proposal_unearths