Conflicted Desires

Trigger warning for bisexuality and harsh derogatory language.
I'd spent years convincing myself I was straight, despite the persistent whispers in my mind suggesting otherwise. Throughout high school and my first two years of college, I dated exclusively women—sleeping with more than my fair share. It wasn't that I didn't enjoy it; in fact, there were moments I genuinely loved it. I even imagined marrying my last girlfriend, Sarah, picturing us with two kids, a golden retriever, and the perfect suburban life—living the lie so completely that sometimes I almost believed it myself.
But as our relationship deepened, I found myself making increasingly frequent excuses to visit a certain adult bookstore downtown with its notorious backroom booths. It became painfully clear that this charade wasn't fair to Sarah—and damn sure wasn't fair to me. The breakup was messy, and for weeks afterward, I endured my roommate Jake's relentless questioning about why I'd let such an amazing girl go.
After the hundredth time being asked, I finally snapped.
"Look, man...I love Sarah too much to keep lying to her when I'm not even sure who I am anymore," I said, my voice cracking with frustration. "I've been fighting the truth that I'm gay for way too long. So there you have it—is that what you wanted to hear?"
Jake stared at me for what felt like an eternity before finally finding his voice. "How could you possibly be gay when you two were fucking each other's brains out every chance you got?"
"I'm not in the mood to analyze what a great fucking liar I am," I shot back. "Guess I thought if I got enough pussy, I'd stop thinking about dick." I knew the last line was pure shock value—but I couldn't stop myself from saying it.
Jake sank onto his bed, rubbing his forehead and clearly struggling for the right words. "I don't know, Alex...we've been living in these cramped quarters for two years, and I never once picked up on the show tunes vibe." He attempted a weak chuckle. "Look...I don't get it, but I'm no homophobe. My cousin came out a few years ago—not that it was any great shock to anyone. The point is...how you handle this is up to you...what you say to me stays between us." With that, he grabbed his backpack and headed to class.
I sat trembling at my desk. Never in my life had I spoken the truth that had haunted me for so long. Jake and I were roommates and got along well, but I wouldn't say we were particularly close friends. I'd given Sarah some bullshit excuse for breaking up, and this was definitely not how I'd imagined coming out. For the next hour, I felt on the verge of vomiting. Fortunately, I only had one class later that afternoon.
++++++++++++
For the next few weeks, Jake did his best to act as though nothing had changed, but his discomfort was palpable. I was miserable, starting to believe I'd made a horrible mistake. Other than a few awkward jerk-off sessions with a buddy in high school and some anonymous encounters at that adult bookstore, I'd never had anything close to an actual gay relationship. I was questioning everything all over again.
Jake's girlfriend stopped by one afternoon while he was still in class. "Don't be mad at Jake for mentioning something to me," Chloe said, kissing my cheek. "He's worried about you...says you seem depressed."
"Yeah...well...try ruining your entire life in one afternoon," I mumbled, a mix of anger and sadness creeping in. "It's not exactly an uplifting experience."
"Sarah's been asking about you. She wants to give you space, but hopes you'll come around," Chloe said, taking the chair across from me in our tiny dorm room. "I haven't told her anything...and I get the impression she's completely in the dark about what's going on."
"Right now, nothing's going on," I snapped back. "I'm sorry...thanks for giving a shit...but nobody can help me with this fucked-up situation. I just have to deal with it."
"Holy shit...how did you go from jock-stud to drama queen so quickly?" Chloe shot back with equal doses of irritation and sarcasm. "Find a boyfriend already and see if that's what you really want. I think this whole thing is just because you've been afraid to try a few things. Being curious isn't the same as being gay, you dipshit!"
Chloe had a reputation for being direct and painfully blunt, and today was no exception. I was about to get really pissed off when Jake walked into the room.
"Uh-oh...I can see in your eyes you've given Alex a strong dose of your opinion," Jake said, looking at his girlfriend's stern face. "Sorry man...but with two women hounding me over what was happening...something had to give."
I closed my eyes, letting my anger subside. They were concerned, and I had to be thankful for that. "I'm sorry you guys have been caught in the middle of all this. I couldn't have handled this any worse."
"Screw the dorm food...let's grab a pizza and some beer," Jake said, checking his wallet. "You can calm down, and Chloe can get pissed that I can't go home with her this weekend."
"What? You're going to make me tell Mom you're not coming? She thinks you walk on water, you know," Chloe said, clearly annoyed.
Although I was reluctant to go, it was nice to just hang out and feel like I was with friends. They might not have completely understood me, but at least they were there for me. Chloe still wasn't happy about going home without Jake, but several beers softened her mood. By the time the evening ended, Jake and I stumbled back to the dorm and collapsed into our beds.
The next morning, we'd both slept late, and I was the first to get up. Jake was still asleep with an obvious case of morning wood straining against his boxers. It wasn't that big a deal—had happened to both of us countless times over the years. I knew Jake had seen me in the same condition and was cool enough not to mention it. Usually, one of us would wake up, notice the situation, and simply roll over to avoid being indecent. Given our recent conversations, I thought he might feel compromised, so I tossed a blanket over him before heading down the hall for a shower. I'd been hornier than hell the last few days without any relief, and seeing him that way wasn't helping. The rest of the day went on about as normally as it could, with both of us feeling more comfortable than we had in a while.
Saturday morning, I rolled out of my top bunk as usual, only to find Jake with another morning hard-on. Any guy knows they can be more of a problem at certain times than others, but this still seemed odd. The covers were trapped underneath his legs, so I couldn't toss them over him this time. I made some noise moving a chair, expecting Jake would get the message and roll over. Instead, he took a deep breath and lazily draped an arm over his eyes. I sat down, taking advantage of his blocked vision to stare at my roommate's slumbering form. I'd always thought he was good-looking, but never wanted to make him think I looked at him in that way. As hard as I'd worked over the years to conceal my interest in cock, it was shocking that I'd spilled the beans so quickly. We both stayed in great shape and were about the same height, but Jake was just a bit more muscular. The most obvious difference between us was our complexion. I had dark hair, brown eyes, and a decent tan—but Jake had the all-over pale complexion that went with his dirty blond hair and blue eyes. None of that had particularly fascinated me until now, as my eyes traveled up his toned thigh and into the leg opening of his boxers. From my seated position, with the morning sun streaming in, I could see the sparse hair that covered his scrotum—the fabric being tugged out of the way by his morning erection. My own prick was starting to swell as my gaze was drawn over Jake's plain gray boxers and to the tip of the tented shorts. The head of his cock pressed against the fly, with the opening revealing a glimpse of the swollen shaft. At this moment, I never wanted anything so badly, but I had no intention of ruining every relationship I still had. I got up to grab my robe, hoping the shower would be empty for a quick jerk-off session.
"Are you going to act like the faggot you say you are...or are you going to make me wait for Chloe to take care of this?" Jake said in a gruff tone, his arm still covering his eyes.
My heart immediately jumped into my throat, and for a second, I hated him for calling me a faggot. Then again, he was probably the only person who could possibly say that and get away with it. I was far too nervous to say a word. My body shook with a mix of fear and excitement as I slowly walked back toward the lower bunk. My hand trembled as I tentatively reached to trace a finger over the moist spot at the tip of his tent pole. Jake took another deep breath as I watched the white t-shirt rise and fall over his stomach. Slipping a finger into the open fly of the boxers, I felt the warm, silky skin of Jake's rod as I nervously fished his cock through the opening. I'd never seen my roommate's prick in this condition, and it was truly impressive. Not overly long, at a bit more than six inches, it still filled my hand with ample girth. The skin was even paler than the rest of him, with bluish lines of veins easily seen under the soft skin that covered intensely hard flesh underneath. The pole throbbed as I gave a firm squeeze, and a drop of clear nectar emerged at the tip of his circumcised dick.
"I...I don't know, man...are you sure?" I asked with a shaky voice, astonished that Jake would ever allow me to do this.
"Shut up...convince me you're a fag," he barked gruffly, still hiding his eyes. "Suck it, or get the fuck away from me."
I'd never experienced this overtly dominant side of his personality before, but I didn't mind. If anything, it made me feel more like I was taking orders than willingly accosting my roommate. Kneeling on the floor and leaning over the bed, I took the tip of his slick helmet into my mouth. Jake's meat was the thickest I'd ever encountered—not that my experience was all that vast. Working up large amounts of spit, I managed to stretch my jaw wide enough to inch my way down the warm pole. By now, Jake was leaking a steady stream of pre-cum into my mouth, and the taste was fantastic—a bit sweeter than my own. After a few minutes, my jaw relaxed, and I began sucking with enthusiasm. Jake was largely silent, only grunting as I focused on the spot beneath the spongy helmet.
"Better at it than I thought you'd be," Jake said hoarsely, reaching down to tug the opening of his boxers under his balls. "Lick 'em, pansy-ass...lick my nuts."
I was too lost in lust not to obey. My tongue slid over the loose, wrinkled flesh that covered a pair of plum-sized orbs. I'd caught quick glimpses of Jake naked after a shower or changing clothes for a date, but never appreciated just how well-equipped he really was. My dick might be longer, but he had me beat in every other measure. The whole package seemed to fit his more muscular, wrestler-type frame perfectly. The sunlight gleamed against the pink hue of his sack and the blond hair that thinly covered it. Even the deeper color of his pubic bush was easier to see with more of his junk out in the open. I lapped hungrily across his scrotum, up the swollen shaft, and devoured his throbbing organ over and over again. My own cock was now painfully hard and leaking profusely within my boxer-briefs. Jake's nuts began to contract, and I knew my reward would soon arrive.
"Oh fuck...you'd better take it all!" Jake groaned, now holding my head firmly in place as he thrust his hips upward. "If I'm willing to do this shit...you'd better not bitch about the result!"
Jake roughly pushed my face tight against his crotch and held me in place. His cock swelled even larger in my mouth as stream after stream of hot spunk shot down my throat and leaked around the edges of my lips. His seed was warm and salty but not unpleasant as I struggled to swallow his load without gagging. I barely touched my own prick before cumming and soiling my underwear. I was still working Jake's softening prick when he abruptly pushed me away and rose from the bed.
"Never had a dude blow me before...but you're damn good at it," Jake said, grabbing his towel and shower supplies. "Don't go expecting anything from me. I just had to know how serious you were about this shit." He then quickly left the room.
I was highly confused, and yet strangely satisfied, as I sat on the floor with cum on my lips and a huge stain on my underwear. Clearly, I had just been used, and should have been pissed off—but anger never came. I'd never been forced into a submissive role before and was shocked to find that aspect is what really got me off. Regardless, I still couldn't understand why "Mr. Nice Guy" suddenly did a Jekyll-and-Hyde routine to get his rocks off. I was sitting in my robe and still collecting my thoughts when Jake returned from the shower. He walked in the door and barely looked at me—as though nothing out of the ordinary had just happened.
"Hey...asshole...you mind telling me what brought that on?" I asked with mock indignation.
Jake sighed deeply and paused a moment before speaking. "Chloe thinks you're more 'adventurous' than you are 'gay'," he said, using his fingers to form quotation marks in the air. "We both think you're too hung up on being either totally straight or gay. Neither of us can imagine you in an emotional relationship with a dude. Your attitude just isn't like any of the gay friends we know." Jake's tone was matter-of-fact and confident, without any sense of remorse or regret.
"Okay. So how does practically forcing me to suck you off help enlighten me?" I asked, now more confused than before.
"Look, man...I think you know that I'm a hundred percent about pussy," Jake said, looking at my confused expression. "Okay...ninety-eight percent pussy...the point is, I'm not afraid of experiencing a good time. I think you're the same—you just haven't put it into context yet."
"I'm afraid I'm still not getting it."
"Great...let me draw you a fucking picture," Jake said, pulling on a pair of jeans and a t-shirt. "Sarah has confided to Chloe several times what a great lover you are. She thinks you have a kinkier side than you're often comfortable with. Sarah would like you to experiment and get comfortable. You should be honored as hell to have a woman that loves you that much."
"So did you all get together and dream up what happened this morning?" I asked, the fog in my brain only barely getting clearer.
"No...the girls don't know I took the initiative," Jake now sat on the other chair to face me. "If you're trolling glory-holes and hooking up online...you need to stop that shit. It's not fair to expose Sarah to god-knows-what. Seriously, think about what a deeply emotional relationship with a dude would be like for you. I'm not sure you have."
"I'm not sure I want you guys all into my shit like this," I replied, uncomfortable that my friends seemed to have put more thought into this than I had.
"You put us into your shit when you dumped Sarah without giving her a good reason why," Jake said curtly, smacking me upside the head. "Not to mention the out-of-nowhere announcement that you're a complete fag."
"I'm just trying to deal with where my thoughts have been going more and more lately. It didn't seem right to fuck Sarah and then think about dick the rest of the day."
"There's the core of the problem," Jake said with smug satisfaction. "You're thinking about cock...not a boyfriend. I have a study table to get to, but here's how this shit is going to go down. Are you listening?"
"By all means...I can't wait to hear where this is going," I answered honestly.
"I'm not into guys, but I am into getting off. Chloe is a real trooper, but she doesn't always want it as much as I do. I know you're not going to blab, so your mouth is as good as anybody's," Jake said while getting up and putting things in his backpack. "Being all touchy-feely with a dude just isn't happening for me...so don't expect any build-up or thank you gifts. Don't ask me for it...you'll know when I'm interested. If you're not into it, or you found the man of your dreams...just tell me to back off." Jake grabbed his jacket and walked toward the door. "I'm going to be your safe and clean cock supply until you work this shit out. Stay the hell out of that adult bookstore downtown...everybody knows what goes on there anyway."
I sat there truly stunned...and with a hell of a lot to think about.
++++++++++++++
After a few heartfelt letters and phone calls from Sarah, I was feeling like the complete jerk I was. We had been together for two years, and our time together was always fun. It was insensitive, at the very least, to cut things off the way I did. The fact that she was still willing to speak to me was a testament to her superior character. To avoid awkward silences, we decided to go on a double date with Jake and Chloe. The evening was fun, and just being near Sarah felt comforting and reassuring. It started to become clear that my friends may have been right about me all along, but I was taking it easy with Sarah. I still couldn't reconcile my need for her along with my desire for more taboo interests.
It had been almost two weeks since my episode with Jake, and I thought perhaps he felt the lesson had been learned. I tried to broach the subject with him once but was quickly shut down and reminded that what happened was on terms that worked for him and that I needed to focus on my own shit. Later that night, Sarah called, and we shared a warm conversation. A date was arranged for two days later, and I actually looked forward to the end of the week.
"Sounds like you guys might be on the mend," Jake said over his shoulder while watching TV.
"Yeah...I think so. She's been much too good to me," I said, hanging up the phone and sitting back at my desk. "I thought you and Chloe were going out tonight."
"She has a cold. Plans to quarantine herself for a few days," he mumbled, still staring at the television with a tone that was more stern than usual.
I might have asked if something was bothering him, but I brushed it off and returned to the magazine I'd been reading. I never heard Jake get up, but my head turned as the sound of a zipper echoed in my left ear. Catching me off guard, Jake quickly pushed his jeans down to his knees and pressed my face against his flaccid cock.
"If you've been avoiding that adult bookstore, then you're ready to help me out," he said gruffly, prying my mouth open with his fingers and slipping his prick past my lips.
"Mmmpphh...mmmppphhh!" was the only sound I could make as Jake held my head tight against the blond pubic hair of his crotch. The flesh resting against my tongue started to swell, quickly filling my mouth and inching its way down my throat. Placing my hands against his thighs, I pushed away and gagged for air. Jake's hard cock sprung from my lips, sending a string of spit across my face.
Grabbing the hair at the top of my head, Jake didn't say a word as he smacked the side of my face with his angry tool. Never in my life would I have imagined getting into this kind of rough play. Jake either understood me better than I did myself or simply didn't care. I was still choking when he pressed the tip of his manhood against my lips and pushed back into my mouth. Within a few moments, I had accepted my fate and began providing the best blowjob I could muster. Feeling more confident, I reached out to tug on my roommate's large balls while he pushed my face down to the root with every thrust of his hips. I could have sucked on that prime piece of meat all night—but Jake had other ideas.
"Lose your pants...now!" Jake barked, loud enough to be assertive but not loud enough for the entire hallway to hear.
There was no doubt I was incredibly turned on, but now felt a twinge of fear. Jake barely looked at me as he kicked off his shoes and tossed his jeans in the corner. He now stood in the middle of the room, stroking his spit-soaked cock and wearing only a blue t-shirt.
"Damn it, you're slow...I'm not looking for a strip-tease!" Jake said, sounding clearly annoyed with my fumbling progress.
I had barely stepped out of my pants before Jake grabbed the back of my neck and tossed me face-down onto his lower bunk. Still holding me down with one hand, he reached under the bed and retrieved a small plastic bin where he kept condoms and other supplies for Chloe's overnight visits.
"Hey man...I've never..." I started to express my apprehension, but Jake was having none of it. "Ow...fuck!" I yelped as his hand smacked sharply on my ass.
"Surprised me...but Chloe loves it in the ass," Jake said while reaching for the gray boxers he wore to bed and stuffing them in my mouth. "I figure a fag-in-training will like it just as well."
I squirmed and struggled against Jake's grip on my neck. I knew I could reach out and squeeze his balls to put an abrupt stop to this game. While I was scared out of my mind, I was also aroused like never before. Another hard slap landed on my ass before I heard the snap of a plastic lid and felt a ribbon of cool fluid oozing between the cheeks of my butt.
"Oh shit...that's going to be nice and tight," Jake hissed under his breath as he worked one, and then two fingers into my virgin hole. "I can't say those hairy moons are doing much for me...but tonight, a hole is a hole."
I tried spitting out the boxers to make another plea, but Jake pushed them back in and pressed my face against the mattress. His grip moved off my neck, and his forearm pressed against my shoulder blades as he forced my legs apart and positioned himself between them. His cock had lost some of its hardness while prepping my pucker, but still felt intimidating as it slid against the cleft of my buttocks.
"I won't hurt you, man...I'll start slow," Jake growled in my ear as the weight of his body pressed against my back. "Chloe would tell you it's a bitch at the start...but it does get better."
Jake shifted his hips, and I felt the head of his cock pressing against my reluctant ring. My body instinctively tightened, and I resisted the insistent intrusion.
"Try to relax...fighting will make it worse," Jake said with a strange mix of compassion and resolve. "I'm horned as hell...and this is going to happen."
Although getting forced into anal sex was not on my agenda, the situation as a whole was ticking all of my taboo sex fantasies—even a few I hadn't considered. Knowing that Jake was serious about seeing this through, I gathered all my courage and fought the natural urge to protect what had always been a one-way passage. The head of Jake's prick quickly slipped past my lubricated sphincter. I let out a muffled cry of pain against the fabric in my mouth, and tears began welling in my eyes. The initial discomfort was searing, and felt as though I would be split in two. Jake was true to his word and remained in position for several minutes, allowing my body to adjust. It seemed like forever, but amazingly, the sensation slowly moved from agony to tolerable.
"Easy...that's it...easy...you're doing better than Chloe did," Jake said in a low, masculine tone. "Open that man-pussy for me...get ready for the fuck you know you want."
Five minutes ago, you couldn't have convinced me this was anything I'd ever want. Now that the pain was less severe, the feeling of being controlled and used was starting to become a genuine thrill. The progression was slow but appreciated as Jake pressed his hands against my shoulders, lifted his body off my back, and inched his thick rod into my bowels. I couldn't believe just the head felt so huge as the ring of my ass stretched further and further until his pubes pressed against my backside. Jake remained motionless for another several minutes until my grunts and whimpers subsided. It felt as though a baseball bat had been shoved up my ass, and the feel of his balls resting against mine was surreal. My roommate slowly retreated and then eased back in again. The pain was still sharp but getting better with every cycle. Once satisfied that I had overcome the biggest hurdle, Jake pulled completely out of my back door and applied more lube. My ass felt like it was gaping open and would never return to its former size.
"I know that's rough...you toughed it out," Jake said, returning his grip around my neck. "This hole is mine now...and I'm going to fuck it hard." He said through gritted teeth, slapping his cock against my overstretched brown-eye.
My eyes shot open wide, and I let out another long, muffled groan as Jake plowed into me with one forceful stroke. His heavy balls slapped against mine as he found a comfortable rhythm. I could feel sweat dripping onto my back as it fell from Jake's forehead. He grunted and groaned like a rutting animal, clearly using me as a tool to get off. It took a long time, but the pain eventually gave way to pleasure as I began to feel my roommate's cock slide against my prostate with every forceful thrust. Pushing the spit-soaked boxers out of my mouth, I offered audible moans to reinforce the fact that I was now a full participant. Though in full retreat at the beginning, my aching cock was now painfully hard and brushed against the sheets with every push from Jake.
"Fuck...oh fuck...seed my ass, man...cream that hole," I mumbled, surprising even myself.
"Tight...so damn tight...gonna fill you with my load," Jake stammered through halting breaths.
I was completely into it by now and began lifting my hips to meet Jake's thrusts—burying his prick even deeper into my chute. His thrusts became shorter and faster, with Jake's breathing growing more ragged. Once again doing a push-up against my shoulders, Jake arched his body and pushed hard into my ass, grunting so loud that I thought someone in the dorm might hear.
"Aaarrggg...fffuuccckkkk...dddaaammmnnnn!" Jake moaned as his body convulsed and the warm spray of his spunk splashed within my bowels.
The feel and sound of Jake's climax sent me over the edge, and I felt spurts of warm cum pool under my belly with my cock trapped between me and the bed. We were both panting for air as Jake rolled over onto the mattress next to me, his cum leaking out of my abused hole and flowing over my balls. The twin bed could barely hold us both, but we were too exhausted to care. My back was getting stiff, so I turned over and stared at Jake's softening tool. I reached out to touch it but was smacked away.
"It was a good fuck, but we're not going to be making out," Jake said bluntly.
I simply chuckled and moved my hand to feel the cum that coated my balls.
"Sorry I came on so strong," Jake said, rising from the bed and wrapping a towel around his waist. "Messing with a dude is a new thing for me, and I just can't do it the same way as with a woman. The whole scene brings out a dominant side I didn't know was so strong."
"Yeah...well...I never saw myself as being quite so submissive," I replied, using his boxers to wipe the cum off my ass. "Getting fucked was never on my list of things to do. The way you did it is the only way it could ever happen."
"Oh...shit, man...sorry...I guess I damn near raped you," Jake said, sounding genuinely concerned.
"I liked having you take charge. Otherwise, I would have grabbed your nuts and squeezed. I think I've also realized it's the wild-ass sex I crave...not necessarily the guy involved. I'm probably not gay...just one seriously twisted pervert."
"Whatever, man. I was willing to tap that tight ass...and I'm not going to make any more of it than that. If nobody got hurt, and you got off on it...then it's all good."
We both showered and finished the evening without saying more about it. I could read Jake's attitude well enough to know that he didn't like to dwell on it. He was upfront about seeing the whole thing as a way of satisfying both our needs for the unusual—he just didn't share my idiotic gay-or-straight take on it.
++++++++++++++
The date with Sarah went incredibly well, and after a long evening of soul-searching, apologies, and reconciliation, we came to appreciate each other more than ever before. I thought my other interests would repulse her, and I knew that I could never block those urges completely. To my astonishment, Sarah seemed to enjoy hearing about the things I'd done and the bizarre arrangement that Jake had forged. She even indicated that she and Chloe would love to watch what we'd been up to, but I suggested that neither me nor Jake were likely comfortable enough for that...at least not yet. Jake and Chloe had left for the weekend, so Sarah and I spent two days reconnecting physically and emotionally. The sex had never been better, but it was the bond of understanding that mattered most.
It was Sunday afternoon, and Sarah had just left to study for her economics test. My top bunk was still a mess, and Jake knew immediately that the weekend turned out well.
"From the look of that bed, and the smell in the air...I'd say you two are solidly back together," Jake said with a stupid grin while punching me in the arm.
"Yeah...things are good...much better than I deserve," I answered honestly. "Thanks, man...I owe you and Chloe a lot for not letting me throw everything away. I guess I needed to grow up...not see things so black-and-white."
"You're welcome. If you ever put me in the middle of a shit-storm like that again, I'll kick your ass."
"Don't tease me," I said sarcastically, knowing it would piss him off.
"Fuck off," Jake replied, throwing my t-shirt off his bed and into my face. "Glad you had a good time. Chloe and I had some fun...but it was tough with her parents around all the time. They're great people...but man, they can be hard to ditch."
"I know the feeling. My parents are the same way whenever Sarah is around."
"Hey...I gotta go to the gym for a few hours. Want to see if the girls can do dinner later?" Jake asked, grabbing his backpack barely a few minutes after walking in the door.
"Sure...that'd be great," I answered as Jake waved goodbye and closed the door.
About thirty minutes later, I got an unexpected text message from my roommate: "Back in an hour. Clean out, lube up, and be face down on my bunk." I was trying to formulate a reply to such a blunt order, but another message quickly followed: "Ok if not...I'll back off."
Even after a weekend of casual fucking with Sarah, the message still managed to get my dick hard. I hadn't thought of anything but Sarah for the last few days, but now my mind was filled with images of Jake's tool. With shaking hands, I managed to text back: "got it."
Despite being occupied with preparing for what Jake clearly wanted, the hour seemed like eternity. I spent a good ten minutes just fingering my ass, stretching it out and lubing my hole. Even Sarah had taken to playing with my pucker, and still I was shocked that I could ever want something I once considered perverse and humiliating. Glancing out the fourth-floor window, I saw Jake calmly walking up the street toward our dorm. I'd never understand how he could be so cool and nonchalant about just walking in and doing what he had in mind. I closed the curtains, laid face-down on Jake's bunk, and nervously waited to hear the key in the door.
"Good choice, fucker," Jake said in a gravel tone, closing the door and dropping his backpack on the desk. "Reach back and spread 'em...show me that pussy."
Placing my hands on each cheek, I spread them apart and put my backside on full and humiliating display. Turning my head to the side, I saw the stern and purposeful expression on Jake's face as he kicked off his shoes, pulled the sweatshirt over his head, and lowered his jeans. The pale complexion of his legs and torso made Jake's choice in swim trunks obvious, and the fiery-red hue of the hair surrounding his crotch was easy to see in the subdued lighting. His cock was already thick and hard as he slapped the pole in his palm and reached for the bottle of lube on the floor.
"You got me into this twisted kink...time to man-up and own it," Jake grumbled, kneeling on the bed and kicking my legs apart. "Keep the volume down...not everyone needs to know our shit."
My fingers clutched tightly at the sheets, and I let out a deep moan into the mattress as my roommate sank his dick in one unrelenting stroke. It still hurt like hell, but the pain subsided much faster than the first time. I could feel Jake's breath on my neck and the brush of his chest hair against my back as he maneuvered for better position. His cock slipped out briefly, pushing against my scrotum, until he quickly rammed it back inside my bowels.
"Fuck yeah...so damn tight!" Jake hissed mainly to himself as he began assaulting my ass with strong, full-length thrusts.
I was relieved that this turned pleasurable so much faster than my first encounter. The ring of my ass still felt stretched impossibly wide, but the sensation against my prostate and the warmth of his prick radiating inside me was incredible. For a brief moment, I wondered if more straight guys might like this if they gave it a shot. Just as quickly, I realized that Jake was a total top who saw my ass as a pussy substitute—so maybe the answer was "no." I might have even chuckled at the thought, but Jake surprised me by pulling out and barking another order.
"On your knees...ass up, head down."
I quietly took direction and moved into position. I felt somewhat more vulnerable with my cock and balls hanging free, but appreciated not having his weight on my back.
Jake rose a bit too quickly and hit his head on the upper bunk. "Oh fuck...every damn time!" he cursed, indicating that sessions with Chloe led to the same result. "Off the bed...bend over...hands on the desk." He barked, rubbing the top of his skull.
Being too horned to appreciate the comedy, I quickly complied and noticed my reflection in the turned-off TV screen. The dark background didn't reveal much detail, and I now wished for a mirror—but the image was still unbelievable. Both of us fit, athletic, and just coming off a weekend with our girlfriends—two guys that no one else we know would believe what we're doing—and yet my roommate is about to plug my ass again with his hard cock. How did I ever get lucky enough to encounter anyone as twisted as I am?
Jake's hands certainly felt rougher than Sarah's as he grabbed my hips and buried his red-hot poker to the hilt. His thighs made slapping sounds with every thrust against my backside, and I struggled to keep a grip on the edge of the desk. This position allowed him to reach even deeper into my guts, and I groaned with every push. My cock was hard as hell, and a long string of pre-cum swayed as it oozed toward the floor.
"A reach-around is fair...but don't push it," Jake said between heavy breaths, moving his right hand off my hip and onto my cock. "Fuck, man...I didn't know you had a porno dick. No wonder Sarah thinks you're the shit."
"Fuck me...oh shit...fuck me!" I grunted through clenched teeth, worried about anyone walking past our door. Naturally, Jake knew how to handle a cock, and his firm strokes were getting me closer to the end. Finally feeling more comfortable, I started clenching around Jake's steel-hard shaft with positive results.
"Damn...oh fuck...fuck!" Jake moaned with every constriction of my overworked sphincter. "I'm gonna lose it...I'm cumming dude!"
I could tell that Jake was stifling the moans of his climax as he pushed hard against my ass, and the first two shots coated my insides. Pulling out, he then shot another three ropes of hot sperm all over my back and ass. Still enjoying the lingering effects of his climax, he then pushed his man-meat back into me for a few extra strokes. I expected Jake to retreat and leave me to take care of my own needs, but instead gathered the cum off my back and started jacking me off with his own spunk as lube.
"Come on, man...shoot it!" Jake growled, with his free hand over my mouth and his softening cock in my ass.
"Aaarrrggg...fffuuuccckkk!" I screamed against the hand that muffled my cries. I came so hard that I thought I might pass out. A pearly-white river of cum shot out of my dick and splashed heavily onto the desk in front of me. Jake's hand was covered in a mix of my spunk and his. He held it out as though not sure what to do with it. Once Jake removed his other hand from my mouth, I grabbed his wrist and began licking the warm slime off every digit.
"Oh gross...you are a sick fuck," Jake said light-heartedly, stepping back as his cock slipped from my ass with a sticky plop.
An awkward moment became stranger when my cell phone started ringing. Not really thinking, I grabbed it off the desk with my sticky fingers and saw the call was from Sarah.
"Hey babe...what are you guys doing?" She asked as a polite greeting.
"Oh...nothing much...just hanging out," I replied, sitting on the desk and watching Jake clean his cock with my t-shirt.
Dinner plans were hastily made, and we all had a great time.
++++++++++++++
Over the next several months, the girls hounded us to share what we were doing—if only on a webcam—but we continued to resist the notion. I eventually gathered the courage to bounce my issues off some trusted gay friends. After their initial shock and my clumsy attempts not to offend them, they agreed I was a complete twit. They also wanted to meet Jake—but I made it clear that wasn't going to happen.