Sleeping with my brothers best friend

Hey guys, my first post on here, as after a while of reading and enjoying Gonewild stories I thought I’d share one of my own from a couple years back, when I was 18. Bare in mind it’s pretty damn long as I kinda need to add the context of the story so you understand the relationship involved.

I’m Katie, 5ft6 with long brown hair, blue-grey eyes, a slim figure, relatively perky butt and a 32c bust. I’d never describe myself as hot or want to seem cocky as I’m an embarrassingly awkward and shy person at times, but I can definitely acknowledge that I was gifted somewhat in the looks department.

(A little context)

At the age of 8, at my brothers 11th birthday party, I developed a pathetic crush for his best friend Christian. Since that day, I’d fancied Christian throughout Middle school and would always linger around when he was invited round, in the hopes of being able to spend some time with him. My mum and brother teased me constantly about it as they could strongly tell, and my crush on him carried on through high school. I would constantly bump in to Christian and be greeted with a wink or stuck out tongue. To my delight, we would talk a lot outside of school online and even play Xbox together for numerous hours along with others, but I imagined he always thought of me as his friends little sister, and nothing more. However, that was soon to change.

After staying good friends for around four years, (I was 18 at this point, him 19) me and Christian began regularly talking online. I’d just come out of a relationship and he had too, even though it was nowhere near serious. Out of the blue, after having a normal talk about my ex and what happened, I opened my phone to a message of him saying, “How big was his dick? I bet it was tiny”. I was shocked at first and then found it rather funny, as I’d always known he didn’t particularly like my ex. Playfully, I typed back, “Meh, it was pretty big. Wonder if yours is too?” Not expecting it to go any farther, my heart skipped a beat when he replied, “Trust me it is, Why don’t I show you and you can be the judge of that yourself?” From that moment then, I knew there was no more just being friends. After playfully talking for a few hours, we arranged to meet up casually on the Saturday coming (That day was a Thursday) to play Basketball and some COD on his Xbox. I don’t think either of us were expecting the upcoming events.

I remember feeling extremely nervous as I strutted up to the basketball courts just a few minutes away from his house, I couldn’t believe I was actually meeting up with my first crush to hang out with. Most of our friendship had been online, and so I’d never spent any proper time hanging out with him. I smiled as he came into my view, he was extremely hot; Relatively short dirty blonde hair, ice blue eyes, tanned skin, 6ft2 and has a muscly build thanks to his great ability at playing Basketball and active lifestyle. He was a kind-hearted, intelligent, good-looking and generally all round good guy, and so in my opinion he was perfect. He dunked the ball into the hoop and turned to see me with a grin. I could tell he was just as nervously excited as I was.

After him trying flirtatiously teach me how to play Basketball for an hour, (I was bloody awful), we were both worn out and so he invited me to come back to his place for a drink. I took up his offer thinking nothing of it, and although we had been flirting and clearly liked each other, I never thought things would get sexual. But oh boy they did.

We marched up the four flights of stairs in his house, and as we got to the top floor he gently smacked my ass. I giggled before realising we were in his room which was in the attic. His house was huge and I vaguely recognised the inside from being young, as I occasionally came to pick my brother up when he had been round. We both sat on his bed and I unintentionally lay on top of his chest as he sat back. He laughed and said, “Did you enjoy the game?” I shook my head and giggled, apologising for being so bad at basketball. He shrugged and smirked saying he enjoyed it anyway, and stretched back on the bed. I looked at Christian, trying so hard not to go red, and daringly said, “Would you like me to give you that blowjob I owe you?” We’d played on COD for most of the Friday evening and joked that whoever lost the 1v1 owed the other head. He grinned immediately with surprise showing off his perfectly straight and white smile, and began to slowly pull down his shorts, “I’d love that” he said. I took a deep breath and pulled down his shorts fully and then eagerly tugged at the waistband of his boxers. His hard 6’1/2 inch cock sprang out and I grasped it tightly in my hand. Not daring to make eye contact, I lent forward and wrapped my lips around his head, before fully taking his whole dick into my mouth.

His length was perfect as well as the width, although he was a little big for me to comfortably manage in my mouth. I bobbed my head up and down continuously whilst using my tongue to lick his shaft and hand at the same time, I couldn’t help but gag and was greeted with his moans of pleasure. Christian then decided to be brave and gently pushed my head up and down whilst mumbling “Oh fuck” and “That feels so fucking good” every few seconds. After what seemed like forever but was infact only 5 minutes, he released his load into my mouth. Unsure of what to do, and still feeling completely bewildered about who I’d just sucked off, I swallowed his cum without thinking. This seemed to turn him on incredibly and he grabbed me by the waist and propped me on top of him. To my surprise Christian began kissing me, very passionately. Although flustered at first, I eventually kissed back and couldn’t help the smile from forming on my face as I was there, being kissed by my first crush.. My brothers best friend.

After a few minutes of making out and mutual groping, I felt his fingers slide down the top of my jeans and into my lace panties. Already soaking wet, the stroke of his index on my clit was overpowering. I moaned under my breath and shifted my body into his, just to be met by a faster pace of rubbing from his fingers. “Fuck you’re so hot Katie” he said whilst inserting two of his fingers into my tight pussy. I moaned in response and as he rapidly fingered me causing squelches to sound, meaning my panties were absolutely soaked by then. I bounced up and down on top of his bare shaft which increased the pace as my lower body was rubbing on his, and I could feel his dick getting even harder as his hand inside me was the only thing between us. With a look of hunger he pulled out and let me lay back on his bed, whilst he slid his boxers off his ankles and then tugged my jeans and panties off. We were both fully exposed down below, and I didn’t mind one bit. He grinned mischievously when he saw I was completely shaven, and slowly positioned himself between my legs with his dick in his hand. I looked at him with lust, the nerves completely gone and replaced with a longing for his dick inside me. He bent down and slowly licked my clit in circular motions causing my back to arch from the pleasure. “You like that don’t you?” He said whilst momentarily looking up at me from between my legs. “I want you to fuck me Christian, now” I pleaded, feeling myself near an orgasm. He sat back up and placed his dick at the entrance of my pussy, and reached down with his right hand to grab a packet from the set of drawers next to his bed. A few seconds later I realised it was a condom, and was glad he remembered as I’d completely forgotten about contraception. “Hope you don’t mind” he said whilst fumbling around to put it on, and without giving me any more seconds to adjust myself he shoved his dick inside my pussy.

I moaned with euphoria and once he was all the way in, he picked up the pace and was fucking me roughly. It felt amazing, and I was holding everything in me to stop myself from screaming out in pleasure. “Fucking hell I think I’m gonna cum already” he said whilst placing his left hand up my top and onto my breast, “You just feel so fucking good” I then sat up slightly and watched his dick going inside me, enjoying the sight. Seeing me take pleasure out of watching him, Christian removed his hand from my top and began rubbing my clit again. The combination of his dick inside me and his finger rubbing me sent me into an enjoyably powerful orgasm, and not soon after he groaned loudly which I took as him finishing. I couldn’t believe it, even if it had only been for a few short minutes, I had slept with my brothers best friend.

After our session, we hung out for a little bit more after cleaning up and I then went home. Later that week we started dating as we liked each other too much to be friends with benefits, and now we’ve been dating almost two years. Although our first time wasn’t the best due to how long he lasted, it sure was impressive, but without a doubt the sex has massively improved, we’ve both become 100% more confident and have experimented with pretty much everything. So I guess that means there’s plenty more stories to share with you guys if you feel like this was interesting enough :)

Source: reddit.com/r/gonewildstories/comments/4d8cqt/sleeping_with_my_brothers_best_friend