I [M] got fired. This led to me finally fucking my best friend [F]

This will probably be a pretty long one, also my first ever write-up here, so I hope it’s good. There will be sexual stuff mixed in but the actual event the title refers to will occur after the dotted line

Bit of info/backstory first. 

I am 25. 6’2, used to be heavily overweight but have lost nearly 90 pounds over the last year and a half. I was once extremely insecure and awkward, still am in some regards, but with the continued improvement of my new body I’ve gained a noticeable increase in confidence. I’d rate myself at maybe a 6 or 7 out of 10. Not bad, but definitely no model. I have an above average dick at around 6 1/2 inches. Not a porn star, but definitely decent.

My best friend on the other hand, we’ll call her Ash (fake name ofc) is one of the most gorgeous women I’ve ever seen. I’m not sure what it is about her, there’s just something with her specifically that really gets me going. Objectively, someone would probably place her at around an 8 on the scale, but for me she’s always been a 10. Shes 26. around 5’6, maybe 120. Fit, petite body with a slim waist, c cup breasts, and a lovely toned ass. 

We’ve been best friends since I was 13, and I’ve always had a crush on her, though I never told her due to my insecurities and anxiety. Flirting was a normal part of our friendship, and throughout the years there’s been some confusion from mutual friends on whether we were a couple or not. Nothing ever came from any of it, and the flirting died as we both went in and out of relationships. Until recently, that is. 

In November of last year, we decided to move in together to cut costs, with her long term relationship ending shortly before, and the lease on my apartment coming up, it seemed a logical choice. I won’t lie, thoughts of sexual encounters did cross my mind, but I was convinced that was all they ever would be. More so, I was just excited to get to spend more time with one of my favorite people. With both of us single and living together the flirting which used to be natural for us returned. At times I thought it was even stronger/more suggestive than before, and I believed I could feel sexual tension between us, but my insecurities told me there was no way, and so it remained only flirting. 

The walls of our rooms were somewhat thin, and there were times where I could hear moaning from her room late at night. The first few times I put headphones on, wanting to not be a creep and be a respectful roommate. Though the temptation was heavy. A few weeks ago, however, the moaning was louder. No, not louder, closer. As if she had moved to the other side of her room, closest to my wall, to masturbate. Did she want me to hear? The idea got me hard almost instantly, and I subconsciously started touching myself. Before I even knew what I was doing, my cock was out and I had moved closer to the wall. I jerked myself off listening to her masturbate, knowing there was nothing but an inch or so of plaster separating our bodies. At the time, it was the hardest I had cum in a long time. A few moans of my own escaped, and while it made me nervous, I kind of hoped that she had heard me too. 

There was no mention of our shared climax the following morning, other than a sly and sensual smile, and an innocent “How’d you sleep?” from her. I thought about the lovely sounds she had made every night that week. 

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This last Thursday I was informed I had been fired due to “budget cuts” and the next day would be my last with the company. As you might understand, it came as a shock to me, and I was immediately bombarded with all forms of anxiety. Not only were my finances going to affect myself, but Ash as well since we split rent and groceries. I was a mess over this past weekend, a tense ball of stress, anxiety, and self-pity. 

“I hate seeing you like this.” Ash said, about an hour in to our heart-to-heart session this last Sunday, where I vented endlessly about all my worries. “You haven’t slept since Friday, I can tell you’re incredibly tense. You need to relax, man.” 

“Kinda hard to relax when we won’t be able to pay for groceries this month unless I find a new job ASAP.” I replied, despondent. 

“You’ve sent out like 50 applications this weekend, what else can you do?”

I simply sighed and shrugged, wincing slightly as the motion hurt my shoulder. 

Ash got up from her seat and walked over behind me on the couch. The slightest brush of her hand against the back of my neck sent shivers down my spine. 

“What’re you doing?” I asked

“Well if you’re not gonna relax on your own,” Ash said, slipping her hand under my shirt collar and beginning to massage my shoulders, “I’ll just have to make you.”

Her hands were soft and warm, my heart began racing, and all that blood being pumped had to go somewhere. After a blissful few minutes of her massaging my neck and shoulders, she asked me to come lay on her bed and take off my shirt so she could massage my back.

If she saw my erection when I stood, which I’m entirely certain she did considering how hard I was, she didn’t comment on it, and got to work massaging my back, straddling my butt to get a good angle. The feeling of her on top of me, although I would’ve preferred my dick to be grinding on her rather than in to the mattress, was enticing. I tried my best to relax, the massage itself did feel amazing and was definitely needed, but my increasing arousal made it hard to get comfortable. Ash must’ve noticed my squirming, as she leaned down and whispered in my ear to turn over with a mischievous smile. 

I was nervous, but did as she asked. She leaned back, and stared at the erection straining against my sweatpants. 

“Ya know,” Ash said, tapping her chin. “I can think of something else that might help you relax too.” She began to slip the band of my sweatpants down, but stopped before pulling down the boxers. “This is okay, right?” She asked, a sense of nervous excitement on her adorable face. 

Dumbfounded and in awe, I simply nodded. Maybe a bit too vigorously, as she began to giggle at my emphatic response. I lifted my hips for her to take my pants and boxers off, and she took a moment to look at my cock, rock hard and pointing straight to the ceiling. She smiled, bit her lip, and said “Oh yeah, I’m gonna enjoy this.” Before running her finger over the tip. I shuddered at her touch and she smiled, leaning down to gently kiss my balls and lick the base of my shaft. She licked up and down the length of my cock a few times, eliciting a groan before taking the head in her mouth. She slowly moved her head up and down my shaft, going deeper each time until she reached the bottom, my entire dick down her mouth and throat. She came up for air, then went back down. Faster this time, she swirled her warm, wet tongue around me as she bobbed up and down. It was perfection. I’ll be honest and say I must have lasted not longer than 2 minutes. 

I warned her I was about to cum, and she picked up her speed. I grabbed a fistful of her hair and blasted rope after rope into her mouth and throat. After my last thrust in to her mouth, she pulled back and swallowed, opening her mouth to show me it was gone and she had swallowed every drop. She was breathing heavily, big blue eyes staring up at me, spit trailing from her chin to the tip of my cock. She had never looked more beautiful. 

I looked at my naked body, already sweating, and hers still fully clothed, and sheepishly asked, “My turn?” 

She laughed and began taking her clothes off. I swear I must have audibly gasped as she revealed her body to me. I had dreamed of this moment so many times and it was finally happening. Her nipples were hard, and her skin was flushed. Clearly blowing me had gotten her worked up. I stopped her as she reached down to take off her panties. “Those are mine.” I said, and her cheeks flushed red as she nodded and laid down on her back. I positioned myself between her beautiful pale thighs and basked in the moment. My mouth must have been watering as I took in the sight and smell of her. There was a large dark spot on her panties, and I smiled seeing it. I started rubbing and kissing her thighs, relishing the tiny moans that escaped her lips. As I reached up to pull her panties down, they stuck to the skin around her pussy with how wet she was. Finally revealed, I stared in awe at the treasure before me. It was the most gorgeous pussy I’ve ever seen. Perfect, pink, freshly shaven and smooth, glistening from her wetness. I didn’t even think before running my tongue along it, hearing a stifled moan come from above. She tasted divine. 

I looked up to see her covering her mouth with one hand. “Easier to let it out when there’s a wall between us, huh?” I asked. 

She laughed nervously. 

“You’re fucking perfect, Ash. I want to hear you.” 

Her face flushed again, and she removed her hand. I went back to work. The image of her body writhing above me as I licked and sucked will be ingrained in my mind forever. Looking up at her, her hips rolling, stomach rising with each breath, back arching, and the faint outlines of her abs beginning to tense, I realized that this was more than just a teenage crush and sexual attraction. I loved her. And probably always have. Too nervous to say anything out loud, I became determined to let her know how much I loved her, through my hands and tongue. I ran my hands up and down her thighs, squeezing her hips, teasing her nipples as my tongue flicked across her clit. She came with a delicious moan and an equally delicious flooding of juices into my mouth and down my beard. 

I didn’t stop, and next I made her come with my fingers. Using one hand to apply pressure from above while I used two fingers to rub her g-spot from inside. She shook and shuddered and moaned my name. It was one of the hottest things I have ever witnessed. The next thing she did, was THE hottest thing I’ve ever witnessed. After catching her breath, she grabbed my wrist and raised my hand to her face.

“Can’t let this go to waste, can we?” She said, before sticking my fingers in to her mouth and sucking her juices off of them. I swear I nearly came just from seeing that. I positioned myself between her legs again, but paused before entering her. 

“You sure you want this, Ash? It’s okay if you don’t.”

“Of course I do, dumbass. I’ve been thinking about fucking you every night since we moved in together.” 

We both laughed, and considering how worked up we both were, I wasted no time getting to business. Our mouths crashed into each other’s as I thrusted inside of her. Her pussy ridiculously wet and warm, clenching around my cock. We both moaned into each other’s mouths as I picked up speed, mixing with the sound of our skin slapping together. I massaged her bouncing tits, and took a nipple in my mouth, sucking and gently biting. If I could have an unending audio loop of just her moans in this moment, I’d forever be in heaven. 

She was holding the back of my head with one hand and kissing my neck, moving up to nibble my earlobe before whispering “I want you from behind.” 

I more than happily obliged, letting her flip over and get on all fours. Her gorgeous ass up in the air, pussy dripping wet and on display, well that was another image I hope to never forget. I slipped in from behind, and began thrusting, picking up the speed from where we left off. She was gripping the sheets tightly, and I gripping her perfect ass, spreading the cheeks to look at her pretty butthole as my cock pounded her pussy below. I could feel the inside of her pussy pulsing, heard her muffled cries of “Oh my God, oh fuck!” and knew she was about to cum. Which was good for me considering I had been struggling not to bust since before we switched positions. I wanted her to come first. Partly so I could tease her about it later, but mostly because I had been dreaming about her cumming on my cock for years. Her pussy clenched, tightening around my dick with a suction like it didn’t want me to leave it, her thighs began to quiver and shake and she screamed my name.

Immediately after her climax, I pulled out and came all over her ass and back. We both took a minute to catch our breath, before she reached down to scoop some of my cum off her ass and lick it off her fingers. 

“Help me clean up?” She asked, breathless. I proceeded to wipe all of my cum off her ass and back with my fingers, and she made sure to lick up every drop I gave her. 

Giving ourselves time to rest and rehydrate, we fucked two more times that night before falling asleep in each other’s arms. 

I had thought about telling her my true feelings when we woke up yesterday morning, but I ended up sleeping in and she had already left for work when I awoke. Yesterday was uneventful, a normal day, almost like nothing happened. I’m at home now, still filling out job applications. She’s at work. As soon as she gets home, I think I’m going to ask her if she wants to sit on my face. At least, I think so now. That courage may leave once she’s here though.

Source: reddit.com/r/gonewildstories/comments/vxn7rc/i_m_got_fired_this_led_to_me_finally_fucking_my