My VIRGIN roommate takes my girlfriend (How my attempt to cuck myself went too far) [MF]

This is **part one** of a somewhat dramatized version of a very real story. Part two will follow soon. Enjoy.

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Chelsey rested her head on my chest as I ran my fingers through her hair.

It was 4:30 in the afternoon and we’d just had sex. Afternoon sex is the best kind of sex, I’ve always thought. And with Chelsey, it was even better. She and I had been “dating” for almost three months, and our sex life, as you can probably tell, was pretty on point. Chelsey, at 19, was a sophomore; we’d met at a mutual friend’s frat party and, after talking for a few days, began dating. I felt so lucky to have scored Chelsey. I wasn’t lacking in “game” per se, but even I felt I was punching above my weight with my girlfriend. Chelsey was an absolute head-turner; petite (she stood at just above 5’2) and just the right amount of curvy. She was of Lebanese extraction, with American parents, and her ethnic background showed. An olive-brown complexion, thick dark hair that fell down her back and the most sensational ass that truly had to be believed to be seen. She was, quite honestly, a fucking *gem.*

When I say we were “dating”, what I mean is that while we spent much of our time together, we had a relatively open relationship. We were in college after all, and neither of us was looking for a serious, long-term thing. Chelsey would hook up with other guys, and I other girls. This was great for us, but was a particular advantage for me due to this fantasy of mine. I’d been fascinated, infatuated, *obsessed* even, with cuckolding since being bullied relentlessly in high school by a total asshole who ended up taking my crush – Haley – to prom, where they’d allegedly spent most of the night fucking in the backseat of his rental limo.

*That* was all hearsay, of course (and high-key seemed like total bullshit), but that was enough to introduce me to what I would later discover was the rush of pure, unrivalled adrenaline that was being a cuck. I’d been reluctant at first to accept that this was something that I *enjoyed,* but by the time I started college I was fully conscious of what about it turned me on, and was comfortable with it. I’d never properly explored it with any girl I’d subsequently dated, but with Chelsey and I’s more fluid arrangement, it felt as close to anything resembling a cuckold lifestyle. The thought of Chelsey having sex with other guys made me horny as hell, but I was more than capable of keeping it under control. It was fun, more than anything. Just a little bit of fun for myself to keep private.

As I lay with Chelsey, feeling her warm breath on my bare chest, I heard somebody come into the small apartment I lived in. My girlfriend looked up and over to my room door quizzically.

“Is that your roomie?” She asked, turning back to me with wide, questioning eyes.

“Yeah, that’ll be him home.” I looked at my phone. He was about a half hour earlier than usual, and Chelsey had normally left before he got back. We had always tried to keep ourselves discreet considering I shared the apartment with Luke. “It’s cool, he won’t mind,” I said, smiling and leaning down to kiss Chelsey. I got out of bed, pulled on sweatpants and a tee and went out to meet my roommate.

Luke and I had been roomies for the last seven months, and we got on super well. He was a genuinely nice guy, but the total opposite of me. While I was the fairly extroverted type, Luke was somewhat less social and suffered a lack of any real confidence. Particularly in the department of women. Luke was still a virgin, and God only knows how. He was a good enough looking dude. More than good, to be honest. He had a few inches on me height-wise, and was pretty well-built. Not jacked, but stocky, like a boxer. He worked out, for sure. I found it weird how a guy like Luke could never seem to bag a girl, with his 6’3 frame and boyish face. Eh. I guess sometimes it *is* all about the personality.

“Hey man.” I said as I walked over to the kitchen.

“Hey,” Luke replied, slinging his gym back onto the couch. He looked at me and then over to my bedroom door that I had pulled closed after me.

“Oh, sorry. Did I interrupt something?” He looked apologetic.

“No, it’s fine man. Chels and I were just chilling.” I filled a glass with water and leaned against the counter top. “How did your date with Sophie go last night?” Sophie was a friend of mine who I’d set Luke up with weeks ago, and he’d only in the last few days plucked up the courage to go on an actual date with her. I was used to being Luke’s wing-man; I did it enough on nights out.

“Uh, yeah it was alright. She wants to go out again.”

“Oh?” I smirked at him. He didn’t respond. “Soo – are you going?”

Luke looked up at me, then down at his hands as he picked his nails, clearly trying to pass on the question.

“Come on, Luke.”

“I mean she’s hot, sure. *Really* hot.” Luke said, his hands now burying themselves in his shorts pockets.

“So carry on!” I encouraged him, walking over to him. “She’s obviously into you, so fucking go for it!”

Luke sighed.

“Listen.” I went on. “How about me and Chelsey come out with you guys? Like a double date? It’ll just be like a group of friends hanging out, and if you and Sophie want some privacy at any time, then – ” I winked at him. “What d’you say?” Luke rubbed the back of his neck, then said “Okay, fine.”

“Awesome.” I said. “When’re you going?”

“Tomorrow night.”

“Oh, damn. Moving fast.” I joked. Luke smiled. Just then, Chelsey appeared from my bedroom, dressed in nothing but a crop top and her red lacy panties. She’d tied her hair up into a high ponytail. As she walked into view, Luke saw her, averting his gaze almost instantly, his face flushing.

“Hey.” She said, smiling bright. “Luke, right?” Luke looked up sheepishly, his eyes flitting, not sure where to land. “Uh, y-yeah. Hi.” He stammered back.

“I’m Chelsey.” She moved toward him, her hand outstretched. Luke took it, his eyes still not sure where they ought to rest. He settled for somwhere in the far corner of the apartment. I suppressed a smile as my girlfriend and roommate greeted one another, Luke’s large, strong hand taking Chelsey’s slight, delicate one. He towered over her. Chelsey smiled pleasantly, looking up at him and then over to me, an expression of amusement on her face.

“Nice to finally meet you.” She said back to Luke, before speaking to me. “Hey babe, I’m gonna jump in the shower and then head back to mine.” We kissed and she scurried off to the bathroom. Luke was still stood in the same spot, but now his eyes followed my girl, who’s incredible ass bounced as she walked. As he watched her go, I saw his semi-hard dick through the thin fabric of his shorts, having to do a double take as I noticed its size. Luke was packing heat. From side on it looked almost twice as big as mine did fully erect, and Luke was barely even at half-mast. *Well shit.* I thought. *How has this guy not gotten laid yet?*

“Yo, buddy.” I elbowed him. “Shouldn’t you be focusing on Sophie?” I said, teasingly. Luke’s face burned red as he realised his hard-on. “Oh *fuck.* I’m sorry, bro.” His hand went instinctively to his dick.

I laughed gently. “No worries, I get it. Chels is hot *as fuck*. Any guy would have the same reaction in your shoes, man.” I slapped him on the upper arm. “So, we good for tomorrow night? I’ll ask Chelsey. She should be free.” Luke reaffirmed his agreement to the double date.

My girlfriend was up for it, too. “Oh, cool!” She’d exclaimed while drying off in my room. Her naked body was killer. Tight, perfectly proportioned, flawless. If I said her entire form – but particularly her ass -[ resembled Autumn Falls](https://www.reddit.com/r/AutumnFalls/comments/hij2rp/pink_dress/), I’d not be lying. “If it helps with Luke’s confidence, I’m down. Me and you haven’t had a date night for a while, anyways.”

It was true. It must’ve been a few weeks since our last real “date.” I mean, Chelsey had gone out with one other guy from her class about two weeks ago, but they broke it off. I hadn’t seen another girl in that time, so it’d be nice for us to do something together again.

The next night, Luke and I got ready while we waited for Chelsey to arrive. We were travelling together, and would meet Sophie at the date venue: a fancy Greek restaurant. We both dressed casually; me in a gray tee, slacks and a light jacket, Luke in a button-down shirt and denim three-quarters. I was in the bathroom brushing my teeth when a knock came at the apartment door. I checked my watch: 6:50.

“Yo, Luke?” I called through a mouth of toothpaste. “Answer the door. It’s Chelsey.”

“Got it!” I heard from the living room.

“Thanks, man.”

I heard Luke open the door and Chelsey’s voice come through from the hall. She and Luke were chatting; well, Chels was chatting. Luke was probably smiling like a dork and trying his best not to spring a monster hard-on on my unsuspecting girlfriend. I finished up and walked out into the apartment to see Luke and Chelsey sitting on the couch. My heart skipped a beat when I saw her – Chelsey looked *stunning.* A baby pink sheer dress hugged her curvacious little body; her hair was immaculately straightened and her demure face made up to perfection – contoured, with glossy, full lips, thick eyelashes and a gold-bronze eyeshadow. Luke could have been at full-mast right now and I wouldn’t blame him at all. He looked flustered. More flustered than he did yesterday. I could tell Chelsey found his reaction highly entertaining; she was a tease, Chels. And a flirt. If a guy was a hot mess around her, she loved it. Not that they were her type, generally. Chelsey had, in the time that I’d known her, gone for the more assured sort of man; not arrogant or cocky, but quick and collected. She found both humour and humility massive turn-ons, she’d told me when we’d started dating. I guess that had said a lot about me, and was possibly the reason so many of her other dates never lasted long.

“You guys ready to go?” I said, clapping my hands together. And we left.

Sophie was already at the restaurant when we arrived, and the four of us sat down to eat. The night started out great, and with Chelsey and I there, Luke seemed to be a lot more relaxed. Sophie and him chatted freely with us, and Luke drank, something he rarely did, and probably for good reason. Luke was a completely different guy when under the influence of alcohol. Gone was the retiring, socially unsure dude I lived with. *This* Luke was talkative and spirited, if not somewhat boisterous and immature. A fair way into the evening, Luke had loosened up *considerably,* and the dynamic within the group changed. Free of the inhibititions of sobriety, Luke began flirting with Chelsey in front of Sophie, which, naturally, did not go down well. Even after telling him to cut it out, Luke carried on passing remarks about my girlfriend, leaving Sophie completely out of the picture.

*Great.* I thought. *This girl is super into you, dude, and you’re blowing it. Good job, moron.*

Chelsey did not seem too bothered, but on numerous ocassions she gave me looks to indicate that Luke was overstepping his bounds. Even for Chels, who liked attention and a bit of flirting, he was being a little too much.

It got to the point where Sophie had had enough, and told me that she was leaving and to tell Luke not to call or text her. I apologised. Sophie was heartbroken over my idiot roommate’s behaviour. I also decided to call it a night and me, Luke and Chelsey started to head back in Chelsey’s car.

“I’m so sorry,” I said to my girlfriend as she drove back to mine and Luke’s apartment complex. “I don’t know what got into him tonight. He usually doesn’t touch anything remotely alcoholic.” Chels shook her head. “It’s fine, don’t worry about it. Guys like him – the shy, weird ones – turn into dumbasses when they’re drunk.”

“You think Luke’s weird?”

“*Weird* was the wrong word, but you know what I mean. He’s not very outgoing. And he’s still – ” Chelsey trailed off. “You know.”

“A virgin?” I asked, although I knew the answer.

“Uh huh.” Chelsey looked at Luke in the rearview mirror. He was sitting behind me. I turned. Luke’s head had fallen to one side and his eyes were closed. “I dunno what to do with him. He clearly needs to get laid.” I said, turning back in my seat. Chelsey snorted, her mouth curling into a wry smile. “That’s the solution to everything with guys, isn’t it? Sex. What do you think getting him laid will do?”

I thought for a moment or two, but had nothing in response. I shrugged. “I dunno. It might give him *some* confidence with girls. To be honest I don’t know how the hell he isn’t bringing home a different woman every night already.”

Chelsey looked confused. “What do you mean?”

*Ah.* I thought to myself. I’d opened my mouth without thinking. Was I really going to tell my girlfriend that my roommate was hung like a god damn pornstar? I breathed in before speaking. “I just meant that Luke – ” I began to falter with my words. “He’s got, uh – well, he’s got other things going for him.” I said. Wow, that sounded dumb.

Chelsey’s brow furrowed for a second or two before realisation came. “Oh.” She said. “*Oh!.”* She let out a soft chuckle. “Jesus Christ, really?” She shook her head. “Well that’s – unfortunate.” I laughed with her. “Yeah, too bad. If only he had balls as big as his dick, he’d be set.”

The rest of the drive home took all of ten minutes, but in that time I noticed Chelsey look back at Luke in the mirror about five or six times. She did it only briefly, but when she did I noticed her grip on the wheel tighten before her eyes returned to the road. She may have been merely checking up on a passed out guy in the back of her car, expecting him perhaps to throw up at a moment’s notice. Or maybe – and as the thought crossed my mind I felt my heart skip another beat – she was hoping to catch a glimpse of a bulge in Luke’s pants. Just a peek of the sort of package I had only minutes earlier informed her he was carrying.

We arrived home, and after saying goodnight to Chelsey, I helped an intoxicated Luke up to our apartment. “Yo, man, Chelsey is fucking *hot.*” He slurred, having woken up. “Yeah, you said. Multiple times, tonight, in fact.” As he crumpled in a drunken heap on the couch, I resigned myself to the fact that I might have to leave him there, and went to bed.

The next day, Luke was a little worse for wear. He stumbled around the apartment complaining of a headache. “Yeah, you went all out last night.” I told him. He looked at me with bleary eyes. “By the way, Sophie said don’t get in touch with her. You blew it big time, bud.” I raised my eyebrows at him, my lips pursed.

Chelsey came round later that morning, and when she saw Luke, smiled politely. “Hey there, Casanova,” she teased him. Luke flushed bright red and rubbed his arm bashfully, but said nothing. “What’s up?” Chelsey went on. “Feeling embarassed about asking me out last night?”

“You asked her out?” I spat at Luke. I turned to Chelsey. “Seriously? He asked you out?”

“While you were having a smoke.” She retorted. “He was *drunk!*” She added, seeing my incredulous expression. She obviously assumed I was mad at Luke for having the gall to ask her out; in reality, I didn’t mind. My explosive response was due not to anger, but to a surge of excitement. My roommate – my hung roommate – had not only been making lewd advances on my girlfriend all night, but he had *asked her out?!* I should’ve been furious with him, but my cuckold mindset had already kicked in, pushing away all rational, reasoned thought. I felt my heartbeat quicken.

Luke sat up. “I didn’t mean it, man.” He whined. “Like Chelsey said, I was blind drunk. I barely remember half the night.”

“It’s fine.” Chelsey said, looking at him sternly. “You can make up for it.”

Luke looked perplexed, if not a little worried. “What? How?”

“Wine me and dine me.” Chelsey glanced over at me, a provocative smile on her lips. Her eyes bounced back to Luke. “Actually take me out on a date, and we’ll call it even.”

Luke froze, his face drained of color. I sat there, not quite sure what to make of the situation. I knew exactly what Chelsey was doing, and I can’t say I didn’t kind of like it. In her mind, she was playing with Luke, like she often did with guys who were nervous around her. I, however, was dangerously close to having my incredibly sexy girlfriend go out for the night, alone, with my big-dicked roommate, and to me that was a step closer to the true cuckold experience. The visions that whizzed through my mind’s eye almost made me dizzy. My heart was pounding so hard I was certain both Chelsey and Luke would be able to hear it. Chelsey stayed eyeing Luke, who glared at me with a panicked expression.

“What’s wrong? You seemed so sure of yourself last night.” Chelsey chided, flicking her hair back. “But – you’re going out with – ” Luke began.

“It’s an open relationship.” Chelsey cut in. “We’re allowed to date other people.” My girlfriend then stood up and moved over to Luke on the couch, sitting down and sliding up to him so that they were inches apart. “So what’s it gonna be?” Luke had began sweating; his collarbone and temples now had a sheen to them. He was also starting to pitch a tent in his sweatpants. The sight of the two of them *this* close, the sight of Luke’s rapidly hardening cock, was enough to bring a sweat on in me, too. I tried to remain outwardly “normal” as I watched Chelsey bat her eyelids at Luke, her soft lips forming a sultry pout. She moved her hand, resting it lightly on Luke’s thigh. I could almost *see* his cock *pulsating* beneath the navy blue fabric of his pants. Chelsey now saw it, too. It was hard to miss, frankly, consdering it must’ve been two-thirds the size of Chelsey’s forearm. Her eyes flitted back and forth between Luke’s[ massive, twitching bulge](https://www.reddit.com/r/CockOutline/comments/hml4c3/chattin_with_yall_has_me_feelin_like/) and his intensely embarassed face. I had become nothing more than an observer in that moment, entranced by my girlfriend sidled up to my roommate mere feet from me.

Chelsey began stroking Luke’s thigh, now. “Come on, mister.” She coaxed. “I’m a busy girl. If you want to take me out, you need to tell me.” Luke glanced over at me, as though checking to see if this really *was* okay. I nodded and gave a look to signal that he should just say ‘yes.’ Luke turned back to Chelsey, swallowed, and then spoke. “Okay, I’ll – I’ll take you out somewhere.” Chelsey beamed. “Great! I’ll come by about seven Thursday night, yeah?” Luke nodded. He was still throbbing as Chelsey jumped up from beside him.

“Looks like I’ve got a date!” She sang, winking at me. I smiled. “Wow! Lucky you!” As she strutted over to the kitchen, I looked over at a dazed Luke and gave him a thumbs up.

This is where the story *really* begins.

The next few days proceded with relative normalcy; me and Luke hung out as we usually did, playing Overwatch and discussing plans for the holidays. Luke did, on a few ocassions, ask if I was definitely cool with him and Chelsey going out, and I assured him that everything was fine and not to stress about it.

“So you’ve never minded her seeing other dudes?” He’d asked one time while we were in the middle of a game. “Nah,” I replied. “We’re both adults, and I’m not the jealous type.” Which, technically, was the truth. I wasn’t. Not in the conventional sense, anyway. “I bet Chels gets a ton of attention.” Luke remarked. I snorted. “Oh boy, does she.” Luke put his controller down and turned to me. “Can I ask you something without you like, getting mad?” I looked at him out of the corner of my eye. “Sure, dude. What’s up?”

“Do you think – I mean, would you be okay if – ” Luke started. He wrung his hands as he fumbled around for the next half of his sentence. “Do you reckon Chelsey would have sex with me?” He finished.

Did I hear that right? Did my roommate, the guy who barely even knew how to say hi to a girl, just ask me if my *own* girlfriend would put out for him?

“It’s just, Chelsey is insane.” Luke carried on, a touch more confident in his tone. “I mean she is *way* outta my league, but I kinda feel like there’s something there. Like, chemistry, or whatever. I just wanted to know if she’s, y’know – ”

If she’s what? Easy? A slut? What was Luke trying to say exactly? I sat there, looking at him, trying to figure out how I felt about him asking if my girl would fuck him. On the one hand, I knew there was *no* chance of that happening. Chelsey was a a mega flirt when she wanted to be, but she was far from promiscuous. She didn’t just give herself to any guy who took her out on a date. On the other hand, my inner cuckold crept back into my headspace, whispering the unthinkable.

*But what if she did? What if your girlfriend could be fucked by Luke’s massive cock? What would that feel like? Would I want it? DO I want it?*

“Dude?” Luke’s voice broke me out of my crazed reverie. “Oh, uh, sorry bro, Chelsey isn’t like that. I didn’t get her into bed until like our fourth date, probably.” Luke looked mildly disappointed. He’d evidently gotten entirely the wrong idea from Chelsey’s “advances” the other day, and I actually felt a pang of guilt. I didn’t want her leading him on. Should I call and tell her to call it off? I pondered if for a second. No. Let Luke go out and enjoy himself. There was no harm in him spending the evening with Chels; she knew him – a little – and she might even give him a few pointers on how to pick up girls and *successfully* date them. This would be a test run of sorts for Luke. It’d do him good.

Thursday evening came, and I was a nervous wreck. Well, nervous *and* excited. I couldn’t believe this was happening – Chelsey and Luke, going out. Of course I was used to Chelsey dating other guys, but this felt different. This was my roomie, the guy I lived with. This felt *closer.* More intimate. It was exhilirating beyond words. Luke readied himself in his room and when he came out I raised an eyebrow in surprise. Luke scrubbed up well. He was wearing a pair of dark, slim-fit jeans and a plaid shirt left open over a tight tee that showed the definition of his chest. Chelsey arrived at dead on seven, and when Luke opened the door to her, both of us gawked. My girlfriend was glammed up to the absolute max – a short, skintight black dress with a v-neckline clung to her, a glittering choker at her throat. She wore silver platform heels, bringing her eye-level with Luke’s neck. Tonight, her hair was styled in a relaxed curl.

“*Wow.”* I heard Luke say under his breath as Chels stood in the doorway. “Alright you two, have fun.” I said, watching them take each other in from the end of the short hallway. Both seemed to be allowing their eyes to wander across the other’s body, before meeting directly; Chelsey held her gaze and I expected Luke to cave and look away, but he didn’t. He met her line of sight and the pair of them stood, looking into one another’s eyes for what felt like an eternity before Chelsey broke contact, turned to me and smiled. “See you later!” She chirped, blowing me a kiss. Luke gave me a friendly – if quick – smile and followed my girlfriend out of the apartment, making sure to give her plump ass an eyeful as he did.

With that, they were gone.

Source: reddit.com/r/gonewildstories/comments/hod86t/my_virgin_roommate_takes_my_girlfriend_how_my