How Rachel Discovered Cuckolding...

Synopsis: Rachel lives with her boyfriend in their new apartment and gets a new roommate, Mike. She's a strong-minded woman that doesn't take shit from anyone, until a peculiar incident happens between Mike and her, causing her to discover a new fantasy that quickly gets out of hand...

Author's notes: This story is told from two perspectives, switching back and forth between Rachel's and her boyfriend's perspective, starting off with Rachel's. Cheating and humiliation themes are strong in this one, so, reader, you have been warned. If you're not into cuckolding/cheating/humiliation, don't bother commenting.

Chapter 1

My boyfriend and I have been dating for about four years before this all happened. I honestly cannot believe the path I've spiralled down the last few weeks but... I want to share my story...

I'll start from the beginning.

Bf and I were recent graduates, him from nursing school, me from my MBA program, and settled down into a new apartment in the city to build a life together. We had applied to dozens of jobs but, by coincidence, we both ended up getting a job at the same hospital -- I was hired as an administrator and he, of course, as a nurse. I absolutely loved this man and he kept being even more amazing as time went on: he was kind, sensitive, an amazing listener, and just so in tune with his emotions -- all of which were a breath of fresh air from the jerks and narcissistic assholes I've dated in the past. He won my heart over quickly when I met him while finishing up my MBA and we've been in love ever since.

Our dream one day is to be able to put down a downpayment on a new house and so we picked a small apartment with cheap rent in order to save as much money as possible. The small apartment wasn't the only compromise we made -- we decided to choose an apartment that we could rent out to a roommate as well. My boyfriend reached out to a couple of his old college friends, asking if any of them were interested in the room, and, a few weeks later, one of them moved in.

This brings me to Mike.

Mike has always been an enigma to me. I first met him when I started dating my boyfriend and, right from the get-go, there was always this odd discrepancy between how he treated me versus how he treated my boyfriend. Basically, he was really nice to him... but when it came to me, he'd immediately switch into this rude jerk, almost like I was beneath him for some reason. I eventually brought it up with my boyfriend and... well, now that I think about it, he was a bit shy and reluctant to tell Mike to be nicer to me ... almost as if my boyfriend didn't want to cross him or something... anyway, I always thought it was weird but decided not to make a big deal out if it because I didn't want to be the type of girlfriend that started drama with his friends...

After hanging out with them for a few months back in college, I started to notice how much of a womanizer Mike was. However, what baffled me was that he wasn't just a jerk to me... he was pretty much a jerk to every girl he spoke with... yet, he never failed to leave the bars with a pretty girl under his arm...

I commented on it to my boyfriend at the time -- I remember him saying, "Yep, no idea how he does it but he's never had a problem getting laid... I never liked having to hear his wild stories about the chicks he bangs, because, well... you know... I'm just not that type of guy..." and he kissed me, implying that he was the type of guy to only date one girl at a time and commit to them long-term -- and I loved that about him -- seriously, it was so refreshing to meet a guy that didn't run for the hills at the first mention of commitment...

But...

I'll be honest...

... because Mike was such an enigma, he kind of had my curiosity piqued...

... like, how on Earth did he get so many women while being such a cocky asshole? Personally, I hated his attitude, and, when put into contrast with my sensitive, sweet, loving boyfriend, it made no sense to me that all these girls threw themselves at Mike... I mean, sure, he was physically attractive, but being hot is so irrelevant when the dude is an insensitive asshole. At least in my books...

Well, fast forward to about a few months ago where Mike had just finished moving into our apartment... The only thing I had said to him was that he was only allowed to move in if he promised to never bring girls home. I made sure to establish that boundary as there was no way I was willing to deal with random girls being brought over to our apartment every night, nor did I want to deal with any loud sex coming from his room... other than that, I didn't really acknowledge him much because, as you already know, I wasn't a fan of him, and he was only there to help pay the rent anyway. To be honest, I didn't give him much thought at all after he moved in since I was intensely focused on my career -- as one of the new administrators that came in at the same time as a bunch of newly hired employees, I was already responsible for whipping some of the new people into shape. After the first few weeks went by, I really grew into the position, turning into this boss-bitch woman who took control of situations and got shit done. After the third week, everyone followed my orders without question, and, if you're wondering why I'm telling you this, well, there's a reason...

See, the hospital's HR made sure my boyfriend was assigned to a different team administrator due to our relationship status so he didn't know about my newly discoeverd boss-bitch attitude at work ... so, instead, he learned about it in the bedroom...

Soon, whenever my boyfriend and I had sex, I was more dominant, more controlling and more demanding towards him... and, to both of our surprise, he lapped it up ― naturally falling into a more submissive role in the bedroom. It was exciting for me to evolve into this new sexual dynamic with him and, even though he never seemed to explicitly talk about it outside the bedroom, I could tell he was enjoying every minute of relinquishing control over to me as much as I was taking it.

That wasn't the only change that happened around then, however... and this is when things started to get... strange...

I guess I was naive to think that something like this wouldn't ever happen when you're living with another guy but... about several weeks ago, I accidentally walked into the bathroom while Mike was still in there... buck-naked...

He froze and stared at me while I stared right back at him, almost like two deers stuck in the headlights. I have no idea why I didn't just bolt out of there or apologize profusely, but... without even thinking... my eyes were immediately drawn to his crotch...

And I finally saw the reason.

The reason why he gets so many women.

The reason why women always call him back, no matter how rude he is.

The reason my boyfriend kept hearing of his wild stories with girls back in college.

It all just... clicked.

Well, the convo we had in that moment was awkward to say the least...

"Ahem... you, uh, see something you like, Rachel?" Mike slowly jested, his lip gradually curling into a smirk.

His voice finally snapped me out of my trance and I looked back up at him, my eyes wide as they could be...

"I... uh... what?... no! I'm so sorry! I'm, uh, just going to leave!"

And I turned around, scooting out of there as fast as I could...

I remember feeling mortified. I had made a complete fool of myself and was absolutely embarrassed. I had no idea why I couldn't string together a coherent sentence back in that bathroom but it was like that boss-bitch of a woman, who kicked ass at work, had just completely disintegrated at the sight of his HUGE cock...

I mean, sure, I'm not very experienced sexually, so I didn't have a lot to compare it to but I had no idea they got that big! It was easily the biggest dick I had ever seen and it wasn't even hard!!!

I felt extremely guilty for just looking at it so I splashed some cold water on my face from the kitchen faucet and vowed to put it out of my mind. About five minutes later, my boyfriend came home from work, walking through the front door as I was just drying off my face. I started acting super nice and clingy to him the moment he walked through the door, as if seeing Mike's cock was still making me feel guilty, even though nothing actually had happened... I hugged my boyfriend tight, asked him how his day was, and acted super affectionate with him as the evening went on... I don't know if my boyfriend noticed my change in behaviour, but probably not because I'm usually affectionate with him anyway...

That night, I dragged my boyfriend to our bedroom and I pinned him to the bed. I rode his cock hard as I kept telling him how much I loved him...

I kissed him,

I stroked the side of his face,

I pinned his arms to the bed as I expertly rode his cock, up and down...

Soon... I was about to cum ― when the unexpected happened; as soon I was on the precipice of cumming, my mind suddenly wandered towards what I saw, back in that bathroom when I ran into Mike...

I pictured his big, thick cock, completely exposed to me ― the biggest cock I had ever seen in my life.

To my genuine surprise, the thrill of thinking about Mike's cock while riding my oblivious boyfriend pushed me over the edge instantly.

I came so hard on his dick; I was shuddering, quivering, and moaning loader than I ever had...

However, as soon as I came, the post-orgasm clarity hit me hard... I felt so guilty again.

I gave my boyfriend permission to cum and we cleaned up. When we were back in bed, I immediately snuggled up with him, trying to be affectionate while simultaneously trying to soothe my guilt and my confusion of why I came so hard...

Well, the next day, I had a crazy time at work that made me forget all about what had happened. The hospital was testing a new medical record system as part of a pilot program that I was left in charge of. Thing is, someone messed up entering in a batch of patient information and this asshole colleague of mine tried to blame the whole fuck up on me -- I swiftly called him out on his bullshit and told him to pack up his shit. This guy that tried to blame me was known to be sexist and rude towards the women on my team... and the moment he tried that shit with me, I chewed his ear out and told him to find a new job. Honestly, it felt so empowering and amazing to finally getting rid of that misogynistic piece of shit. So much that I decided to go home early for the first time since working there and I left work around 4pm.

Mike was working from home these days, as his company had shifted to remote work due to the pandemic (the hospital, of course, insisted that my boyfriend and I came in still) so when I walked in to the apartment, Mike was in the kitchen and saw me...

"Oh, hey -- don't worry, thought I'd wear some clothes this time..." he snickered at me.

I stared at him for a moment and then embarrassingly chuckled. "Haha, yeah... I can see that... look, I'm so sorry about yesterday... the door was closed and I should've knocked... I didn't really see anything anyway so you have nothing to be embarrassed about..."

I wanted to kick myself -- it was so obvious I had seen his cock -- I damn near stared at it! And as soon as I heard myself say that, I knew Mike would make me eat my words...

He snorted loudly. "Oh, so that's how you want to play it? Just going to pretend like you didn't gape at my dick when you walked in?"

My face turned beet red. I embarrassingly laughed and said, "... okay... maybe you're right... what I said still stands though... you definitely don't have anything to be ashamed of... if you know what I mean..."

I couldn't believe what I said. I wanted to kick myself even further... until I noticed Mike eying me, up and down as he processed what he had just heard...

I straight-up started having butterflies in my stomach as I could feel Mike's eyes all over me, relishing in the fact that I just admitted to thinking he has a nice cock...

"Wow... You think your boyfriend would appreciate you complimenting another man's dick like that?" Mike gleamingly taunted.

My eyes went wide with what he accused me of...

"Wait, what??? No, no, no, I was just trying to lighten up the situation -- I wasn't trying to -- "

Mike suddenly stepped closer to me and was now standing over me. His tall, 6'4" stature easily dwarfed my tiny figure...

"You girls are all the same... as soon as they see my huge dick, they just can't stop gushing over it."

I was shocked. "Um, excuse me?! What the hell is that supposed to mean?!"

"It means I see through your whole good-girlfriend act. It means, deep down, you're probably just a huge slut that loves big dick as much as all the other sluts I fuck."

I was absolutely floored. My jaw dropped. Then closed. Then opened again to say something but my words failed me. Sure, I was used to Mike being an asshole to me, but this... this was so over the line that I was completely caught off guard.

Yet, instead of scolding him for being extremely inappropriate, here I was, acting like a flustered little girl, unable to string together a single sentence -- I remember frantically thinking, What happened to that boss-bitch woman that dominated at work today? Why the hell was Mike having this effect on me???

"Not even going to deny it, huh? Don't worry, you don't have to -- I know you must've had a slutty past and you probably had some big cock before. Let me guess, you miss having a big dick? Because I know for a fact your boyfriend isn't winning any points in that department."

Again, I was stunned. Finally, my words found me. "... Okay, first of all, you don't know a thing about my past!! And, second -- "

" -- Oh really?" Mike interrupted, "I know you used to be a huge raver and went to all those music festivals during college. After you gawked at my dick yesterday, I checked you out on Instagram," and he pulled out his phone, showing me some old photos of me in scanty rave-attire at one of the Ultra music festivals I went to.

He continued. "If there's one thing I know about how girls act at these kind of things, it's how slutty they get when they're tripping on drugs," he smirked, looking me up and down.

I remember just looking at his phone propped in-front of my face and then back up at him. Was he really going to slut-shame me for the way I dressed at a music festival??? I remember thinking, how on Earth does that mean I was a huge slut when every girl dresses that way at those events and I was just trying to fit in! The truth is, as I mentioned before, I wasn't very sexually experienced (only dated one other guy before my current boyfriend, no one-night-stands, etc...) so I was never really slutty despite dressing like that... yet, Mike clearly had different ideas about me...

If he was any other guy, I'd have screamed at him for being a misogynistic asshole... just like I did to my ex-colleague at work... but... for some reason... the way Mike was taunting me about wanting his big dick... and making those humiliating comments about my boyfriend...

It started to stir something up in me...

Something I had never felt before...

"Tell me this," he continued, "Have you thought about my cock since yesterday?"

I winced at him, embarrassed, as I recalled the memories of last night with my boyfriend -- the memories of me thinking about Mike's huge dick while riding my boyfriend... no... the memories of how thinking of Mike's huge dick instantly made me cum! ... And, well, I guess my hesitation in responding to him gave my answer away.

He grinned while he leered down at me.

"I thought so. Must be frustrating knowing the real cock you want is actually in the room next to yours while your little boyfriend tries to make you cum..." he chortled.

I glared up at him, fuming, yet my stomach was still full of butterflies. I wanted to yell at him for saying something so disrespectful about my boyfriend... but, at the same time... the way he was humiliating him right to my face... emotions continued to stir I never knew existed -- my anger started to become overtaken by a feeling that was confusing at first but, the more it grew, the more one thing became clear to me...

Mike was turning me on with the way he was talking to me...

Combined with the image of his huge, hung cock from yesterday being seared into my mind, I started to look at him in a completely different light...

His towering stature...

His muscular arms...

His deep, gruff voice...

All things I noticed before but didn't really notice... if you know what I mean...

But, before I could say anything back to him,

The front-door unlocked...

... and my boyfriend walked through.

The tension between Mike and I completely evaporated as I was brought back down to reality at the sudden presence of my hubby. I quickly pulled away from Mike's personal space and I bounced over to him, putting on my usual bubbly-happy voice.

"Hey baby! I missed you!" and hugged him. "You wouldn't believe the day I had at work today, it was brutal... I'm so glad you're here now..."

I caught Mike continuing to smirk at me as he watched me be overly-affectionate with my boyfriend, almost as if he knew I was just doing it to soothe my guilt that was currently doing somersaults in my stomach...

I have no idea why but this was the second moment I remember when I started to feel... a bit turned on again; as I hugged my boyfriend, I was making eye contact with Mike over my boyfriend's shoulder, connecting with his condescending, judgemental gaze... like he was judging me for trying to act all lovey-dovey with my boyfriend, moments after his intense confrontation about me admiring his cock...

The fact that my boyfriend was oblivious to me staring at Mike behind his back while I hugged him... I don't know... it did things to me... again, making me feel things I had never felt before... and I caught myself getting a little bit wet...

Eventually, I broke away from Mike's gaze and pulled my boyfriend over to the couch. We sat down and I proceeded to tell him all about my insane day, including firing that one sexist colleague I mentioned earlier. My boyfriend intently and supportingly listened, like he always does, validating all of my decisions I had made at work and telling me how proud he was of me. He even claimed how badass of a woman I was and that I would never let any man talk me down like that. I swelled up with pride and was instantly reminded how much I loved him, immediately kissing him on the lips.

Right at that moment, Mike decided to sit down on the sofa next to us and joined in on the conversation...

"Damn, Rachel... that dude you fired sounded like a huge dick..." he quipped, sipping on a drink he brought with him. "I guess by the sound of it, you know how to handle a big dick... don't you?"

I literally just stared at Mike, shocked that he had the balls to say something like that in front of us... I mean, obviously my boyfriend had no idea what Mike truly meant by that... but I clearly did!!

"Yeah... I guess so..." I eventually peeped back at him, "... I feel like I'm pretty good at taking care of a big dick..." I slowly said, staring right back at Mike.