I moved in with Joseph under less-than-ideal circumstances. He had listed his bachelor apartment in a classified ad as a sublet. The rent was cheap, and I was just beginning a trial separation from my girlfriend, Becky. I needed to move out and fast, and Joseph’s place was affordable. However, when I moved in, things had fallen through with the place he was to move into. As such, he was no longer moving out. He was also not willing to refund me. I had no place to go, so making the best of a bad situation, we decided to room together in the small apartment, with a divider between us for privacy, short-term.

Roommate Cuckold Stories: My Girl Had a Crush on the Bully I Lived With

Joseph was a guy’s guy, all man. He worked as a security guard at a nightclub, although his hours weren’t what they used to be. He was looking for work elsewhere. I told Joseph I could hook him up, as Becky ran a popular nightclub downtown. She and I were still on good terms – I even worked at her club on weekends as a busboy. She wasn’t too happy about me making promises on her behalf and declined to hire some guy I had just met. Joseph wasn’t too happy that I teased him with potential employment either. After that day, he started to be a real dick to me.

I was intimated by Joseph. I came across as a yes-man around him, agreeing with everything he said, and doing everything he asked me to. I was the one who cleaned the toilet, tub, and sink, made both our beds, cooked both our dinners and did both our laundry loads. I would have done it anyways because Joseph was a bit of a slob, and I liked things neat and tidy.

I was intimated by my roommate. I came across as a “yes man” around him, and did everything he asked me to do.

Joseph started to become less of a roommate and more of a bully as the days passed. He took my maintenance of the apartment for granted, asking me why things weren’t done when he came home. He would have me re-make him sandwiches if the one I had prepared wasn’t good enough. He banished me to a windowless storage room beside our kitchen when he had girls over. I got a lot of reading done in that room, drowning out the screams of women excited to ride his apparently huge cock.

I complained to my girlfriend about my roommate, telling her about each thing Joseph made me do. I told her everything I had done for him, including the time he used my back as a footrest while he played video games. I liked venting to her about Joseph, because when I talked about him, she hung on my every word. Our conversations about him started to become a ‘what did he do to you today?’ routine.

My Girlfriend Was Eager to Meet My Bully

After so much of my whining, Becky decided she wanted to meet Joseph. I assumed it was to give him an ear-load, but when they met for the first time, there wasn’t an ounce of negativity coming from her. My roommate looked down at my 5’8” girlfriend, and she looked up at his hefty 6’2” frame. She had the same eyes a fan has upon meeting a celebrity or public figure they admire. My girlfriend was wide-eyed looking at the kid who tormented me, daresay she as almost star-struck. The smirk Joseph gave me suggested he saw what I did.

They made small talk while I prepared myself to get ready, as Becky and I had a lunch date. Just as I had put my jacket on, Becky asked me, right in front of Joseph, for a raincheck. She wanted to take out Joseph for lunch instead, eager to get to know him better. I was taken back by this, telling Joseph he was welcome to join us. Joseph grabbed the front of my shirt, clutched it and pulled me close to him, telling me I had a lot of work to do around the house, nodding to the bathroom, kitchen and floors. My mouth was wide open, but I had no idea what to say. When Joseph released his grip and I fell back on my ass, I heard Becky giggle and moan at the same time. When he looked at her, smiled and winked, she bit her lip and smiled back at him.

My girlfriend was wide-eyed looking at the kid who tormented me, daresay she as almost star-stuck.

“Let’s get outta here,” Joseph said to my girlfriend, putting his arm around her shoulder and walking her out the door. “Lock the door, chump.” He said to me while looking over his own shoulder. Neither one of them could stop smiling as the door closed behind them.

After finishing the chores Joseph had assigned me, I waited for my roommate and my girlfriend to return. Neither one of them answered their phones for a good two hours. I left to run errands, and when I returned to our apartment building another hour later, I heard the unmistakable sound of a girl moaning from inside our place. Not wanting to wait in the hallway or our storage room for them to finish fucking, I walked in, intentionally averting my eyes. From my peripheral vision, I could see shadows of Joseph mounting some girl. I could hear her take deep breaths as if trying to adjust to the size of something. I made myself comfortable in the windowless storage room and shut the door, turning my radio on to drown out the sounds of Joseph’s latest girl whispering things about his big dick. I continued to try reaching my girlfriend, but her phone remained off.

I could hear her take deep breaths, as if trying to adjust to the size of something.

After I heard the commotion stop, it didn’t take long before the girl scurried out of the apartment. As soon as I did, I came out and saw Joseph, a sweaty mess, with a cocky grin on his face, expecting some kind of reaction from me. Not knowing what to do, I awkwardly put my hand up for a high-five. Joseph looked at me incredulously, like he was expecting a different reaction. His expression changed to one of realization, and laughing, he high-fived me back.

Except he wasn’t high-fiving me. When his hand touched mine, he put something heavy, warm and wet in it. It was an extra-large huge condom, and his cum was seeping between my fingers.

Joseph told me Becky hired him as a security guard at the club, which shocked me. I guess meeting Joseph in person changed her mind. I brought this up to Becky when I finally reached her, about 10 minutes after I came out of the storage room. Becky told me she really liked Joseph, to the point where she felt she could help him with his employment needs, almost obligated to with his skills and her industry. I was glad she was able to help him, even though I was apprehensive about the three of us working together.

Becky spoke to a few employees before making her way out. I saw that Joseph had also grabbed his jacket and walked out behind her. I clenched my fist, seeing him leave early on his second day on the job, just because the boss wasn’t around.

When I got home that night, sure enough, I came home to the sounds of fucking. I walked in loudly, passive aggressively. The divider between Joseph’s bed and mine concealed both his body and face, along with the girl under his stocky body. Through the divider’s shadows, I saw the girl’s legs wrapped around Joseph’s ass. Her arms pulled him close, her hands gripped his back.

“Uh-oh”, Joseph said to his girl in a mocking tone, loud enough for me to hear. “You smell that? Numb-nuts is home.”

“You are such a bully.” I heard the girl whisper, between kissing his neck. “I love the way you treat him.”

“I know you do.”

“I was wet for you before I even met you.”

“Heh heh…”

“I mean it. The more he cried about you, the more I wanted you. He indirectly sold you to me as the ultimate alpha male.”

“What a dope.”

“I looked you up on Facebook…I masturbated to your pictures…I—”

“Sweetie, less talking and more sucking, okay?”

“But I–ggbobbbbbbmmmmph…..” The woman’s rambling was shut up by something shoved in her mouth. Quite frankly, even though she was whispering – almost like she was covering up her voice – I was glad to hear her shut up. I saw the shadow of Joseph’s head move in my direction.

“Hey numb-nuts, take a shower and burn those clothes, you’re stinking up my place.”

“MMMMPHHHHHHH!!!” the woman moaned, her mouth way too stuffed to unleash a full squeal. Joseph was laying it on thick just because he could.

Intending to shower anyways, I spent a good 10 minutes cleansing a hard day’s work off my body, taking longer than usual, giving a chance for Joseph’s latest score to leave. Sure enough, she was still worshiping the brute when I came out of the bathroom. I could see the silhouette of her body, on all fours on his bed. His quarterback-type frame knelt behind her, with one of his hands on her ass, the other one pulling the back of her hair. The more she tried to talk, the harder he fucked her. She seemed to be egging him on, shouting things about his huge cock, and how good it felt to finally be with a real man. This girl was talking in a trance-like state. Not under the influence, rather, completely under the spell of Joseph’s throbbing meat between her legs.

I waited another ten minutes in the storage room, hoping their sex session would conclude, but it didn’t. The usual pattern was for the girl to gather her things and do the walk of shame out of the apartment once Joseph blew his load. This girl was different, though. I suspected they had already fucked a few times that night. The girl sounded dick-deprived, comparing Joseph to her boyfriend. I also recognized the voice – it was the same girl who was screaming out Joseph’s name the day he went out for lunch with my girlfriend. That was the only thing familiar about her. When she spoke, it was between breaths, either while panting, moaning or shouting obscenities. I’ve never made a girl talk the way a girl did when Joseph was inside of them.

“…the more my boyfriend complained about you, the more I wanted to fuck you…”

After realizing the sexed-up couple was never going to stop fucking, I walked out of the storage room and crawled right into my bed. I put my headphones on and hid under the blankets, I could still hear Joseph’s bed squeaking, his mattress bouncing, his headboards banging the walls. I could hear his heavy breathing in sync with hers. I could smell a mix of sweat and cum in the air around us. It was all too much to take, and eventually, I gave into an erection I was hoping would go away.

I pulled the covers off myself, pulled my boxers down and stroked my cock listening to Joseph’s girl giggling, whispering and swearing. It was hard not to be in awe of his sexual prowess. He had this girl completely under his spell, she was worshiping him and he was loving it. I started stroking my dick faster when Joseph taunted the girl about having a boyfriend, asking questions, comparing the two men. It felt like Joseph was talking about me when describing the woman’s significant other.

Just as I could see the shadows of my big cock roommate fucking his girl, I hadn’t considered that Joseph could see my shadow. When he looked my way, he laughed and thumbed in my direction while whispering to the girl in front of him. I stopped jerking off after I saw their heads turn – their laughter made me self-conscious about continuing. I was embarrassed by Joseph yet again, only this time I was caught masturbating.

“Naw buddy, don’t stop!” Joseph said, lying on his back, still laughing. “Come on, baby, let’s give him something to tug it to.” He said to the girl grinding on top of him.

“You’re so evil!” She whimpered, although she was going along with it.

“Look who’s talking.” Nodding again to me. “Fuck yeah, baby, ride that cock…”. His hands were mauling her big tits, and their pace quickened. She was almost hopping up and down on his fat cock, and from the outline of the shadow, it looked beer-can thick. Sensing neither one was looking at me, I started stroking my dick again.

It was kind of hot, actually, listening to someone fuck beside me. She was moaning like a porn star, and he was really going to town on her, thrusting hard, throwing her around while she was still impaled on his dick. I was sure the bed’s legs were going to give out based on the pounding it was taking. It was too much, I was about to come. Thankfully, so were they.

“OH GOD, FUCK ME, FUCK ME!” the girl shouted, loud enough to wake the neighbors.

“UHHHH….I’M GONNA BUST ANOTHER NUT BABE, RIGHT INSIDE YA!” he shouted.

“OHHHH…OHHHH….I’M CUMMING! I’M CUMMING ALL OVER YOUR BIG DICK AGAIN!”

“YEAH BABY! DO IT! DO IT! HEY NUMB-NUTS, RALLY HER BRO, TELL HER TO RIDE MY COCK!”

“Do it!” I shouted.

“YOU CAN DO BETTER THAN THAT, DUMMY,” Joseph said in my direction.

“FUCK HIM!” I shouted. She seemed to be convulsing on his dick, her body was shaking. I think she was really getting off on me cheer-leading her to orgasm. “FUCK HER HARDER, JOSEPH, FUCK HER LIKE HER BOYFRIEND CAN’T!”. That last sentence may have been over the top, as Joseph started laughing harder than usual.

“YOU HEAR THAT, BABY? HE WANTS YOU TO CUM! ALL OVER MY BIG COCK!” he shouted.

“OHHHHH YEAHHHHHHH….FUCCCCKKKKKKK….” She moaned.

“AW…AW YEAH…FUCKK…..” Joseph shouted in spurts.

“SOOOOO MUCH CUMMMMMM…..”

“Look at that…all that cum leaking down my balls, fuck yeahhhhhh…..”

“I’m still having mini orgasms, what have you done to me…”

“I unleashed the beast, baby.” He chuckled, catching his breath. “Like you said earlier, this is what it’s like to be with a real man.”

“I had no idea what I was missing out on.”

“Mmm-hmmm. Clean me up baby, I don’t want to sleep in all this cum.”

They continued to make small talk but I zoned out, falling asleep the second I shot my load all over my stomach and chest. The girl must have left while I was out cold.

Caught Jerking Off Listening to My Roommate Fuck Someone Familiar



I awoke the next morning to Joseph’s voice, overhearing him talk to one of his buddies on the phone. No surprise, he was bragging about his conquest the previous night.

“Yeah bro,” Joseph said. “Nailed her first week on the job. Personal best.” I heard him say as I got up and prepared myself for the day ahead. I showered, wondering if Joseph had brought home someone from work last night, based on his ‘first day on the job’ comment. I panicked, worried that, whoever she was, she would tell the rest of the staff how I beat off listening to her fuck my big cock roommate. I voiced my concern to Joseph when I got out of the shower.

“So…no hard feelings about last night,” I said. “I forgive you.”

“What? Oh yeah.” Joseph replied while laughing to himself. “I forgot about that, that was rad. Sucks to be you tho, bro.”

“Whatever. Listen, about last night…”

“Yeah, that was insane.”

“Um, yeah, listen, can you two not tell anyone what I did?”

“What? You mean how you were caught jerking off listening to me fuck your—”

I immediately cut him off. “I know, I know, she works with us, I heard you on the phone. Listen, it’s just…I mean, I don’t want my girlfriend thinking I masturbated listening to you have sex.”

“Haha, too late.”

“Shit,” I said, realizing the secret was out. Either the girl or Joseph’s buddy on the phone must have already gossiped.

your girl gets wet when your bully slaps you around in front of her.

“She’s coming by again tonight.”

“Same girl?”

“Yeah, dumb-dumb, your g—”

“We need to come up with a better system. I can’t wait in that room all night.”

“Maybe I’ll fuck her right in front of you.” My dick got hard when he said that.

“I don’t…I mean…you think she’d be cool with that?”

“I don’t care. She’ll do whatever my dick tells her to.”

“Wow,” I said, trying my best to hide my erection.

“She loves it when I pick on you. She calls me your bully.”

“She’s really out there.”

“Naw man, she’s just way into me.”

“Her boyfriend must be some chump.”

“He certainly is,” Joseph said, walking away from me, but grinning while saying that last sentence. Then he turned around. “Ex-boyfriend, by the way.”

“She kept saying boyfriend.”

“Well, they’re on a break, but my big dick breaks hearts, buddy.” He said, proudly.

“Sucks to be him.”

“That’s what I just told ya.”

“No, you said sucks to be m–”

“It’ll get worse for him tonight.”

“What?”

“Be here around 10pm tonight.”

“I can’t, I—I…have plans.”

“Be here at 10pm tonight.”

“…yes, sir.”

“Good boy. Now get my breakfast ready, I’m hungry.”

END