My Roommate's Toy Box Ch. 03

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Tyler gets in on the action, things definitely getting weird.
7.9k words
4.74
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82

Part 3 of the 6 part series

Updated 06/10/2023
Created 07/21/2020
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As the hours ticked away that night, I steadily grew more worried that Alex might snap on me and freak out again at any moment. He'd showed me his biggest secrets, touched my dick, and busted twice, all the horniness temporarily drained out of both of us. I anxiously imagined him glancing over, realizing I was still naked, maybe looking down at my dick and recalling that he'd touched it, deciding the whole experience was way too much for his fragile, indeterminate sexuality. I thought about putting my clothes back on, but if I did that maybe he'd feel like he had something to regret. I covered my crotch with the sheet instead, thinking that looked innocuous enough.

Instead of reprising the awkward silence that had accompanied the facial a few days ago, my roommate bantered the way he always did, lying naked over in his bed with his phone in his hands. "Oh shit!" he yelled out suddenly, jumping down to the floor and standing there naked in front of me.

I panicked a little assuming the moment had finally arrived, readying myself for another uncomfortable display of his masculinity, looking nervous as I peered up at his face.

"I have fucking assignments due by midnight!" Alex said like he was annoyed, shaking his head. "I was so fucking satisfied I totally forgot." He walked over to his desk, settling into his chair, his massive ass poking against the back of it as he opened his laptop.

Relief washed over me and I was instantly staring at his hot body again. "Anything I can help you out with?" I asked, feeling guilty that I'd taken up his time.

He craned his head back at me and grinned. "No, man, I think you've already helped me out plenty tonight."

I went back to mindlessly scrolling through stuff on my phone, periodically glancing at my roommate's ass. He worked quietly for awhile, his typing the only audible sound in the tiny dorm room.

"You thought I was going to start being a dick again, didn't you?" Alex asked, not looking over as he typed.

Of course he'd noticed the expression on my face. There was no way to hide it. "A little, yeah," I admitted.

"I told you, dude, I'm fine." His fingers stopped moving on the keyboard and he twisted his face to mine. "You want to know the truth about something? I've never been able to tell a girl about my...fetishes."

Hearing that, I actually felt bad for him. There was pain and loneliness obvious in his voice as he'd spoken the words. "That really sucks," I said sympathetically.

Alex clicked his tongue, turning back to his laptop. "Yeah. So relax and stop worrying. I really liked sharing that part of myself with someone who actually understands it. Especially you. We're totally cool right now, seriously."

Especially me? I was going to spend the rest of the night overthinking those words. "Thanks, Alex." He started typing again without saying another word as I tried to distract myself scrolling through news articles on my phone. Especially me? He was so brazen with me because he knew I accepted everything, noticing how much I enjoyed looking at him on the first day we'd moved into the room. Lying around in his boxers and shamelessly stripping down in front of me wasn't ever malicious. My roommate was granting me the glances he knew I craved without ever doing anything to come on to me. I'd never believed he was gay, never thought he was pretending to be available, just assuming he was a bro who didn't give a shit about being nude or barely clothed around another guy. He got off on knowing how much I appreciated it. He loved me watching him stuff his ass with his toys because he knew how much I was enjoying it. Is that why he'd grabbed my dick? Was he feeling how hard I was because he wanted proof that I wasn't judging him for what he liked?

Alex didn't feel the same freedom with women that he felt with me, and that made total sense in my mind. Straight guys are supposed to be the ones trying to score anal from reluctant girls, the idea that they'd want to be swallowing up massive sex toys themselves incomprehensible. I was imagining the reaction of any random chick Alex might volunteer his secret to, picturing them being as appalled as his dad would be if he knew. They'd probably instantly assume he was a closeted gay guy trying to find a way to satisfy his desires. I wasn't sure what to think. Could he actually be straight? Was our experience together all about safely indulging the secret he'd harbored for years? /Especially you/. The words were endlessly reverberating through my mind.

"Done!" Alex called from his desk, slamming his laptop shut.

The sound made me jump up, wrenching me from my thoughts as I watched my naked roommate lift out of his chair, his fit body raising up, his hairy crotch on full display as he walked toward me, standing between our beds.

"I'd say we should jack off again but I'm fucking drained after riding those toys and having to use my brain." Alex smirked at me. "Want to do it in the morning?"

Just looking at him and believing that he was completely comfortable with me had my dick rock hard beneath the sheet. "Yeah, roomie," I said back. I'd never called him that before but I wanted to test him, to see how he would react.

Alex grinned widely at me, innocently scratching his hand against his balls. "I got so fucking lucky living with you, man. You have no idea." He climbed into his bed, throwing his sheet over his body. "Seriously, we're getting off together in the morning," he pronounced. "We should start every day like that."

/Especially you/. /I got so fucking lucky living with you/. "Good night, Alex," I called to his bed.

"Sweet dreams, roomie," he said back. "Maybe about me?" He laughed and buried his head into a pillow.

/Especially you./ My roommate was quickly snoring contentedly and I couldn't stop obsessing over those words. Especially me? I glanced over after a few minutes and he'd turned to his side, his sheet draped beneath his ass, his massive furry mounds poked out of the fabric right toward me. The room was silent except for his snoring, his butt barely visible in the dim light streaming through our window from the courtyard, but I was jerking off again anyway. I was imagining creeping across the floor, burying my tongue between those cheeks, Alex rousing and telling me it was totally fine, that he'd always wanted a tongue against his hole. I definitely wasn't brave enough to actually do that, but I shot my load picturing the scenario, wiping the cum up with my sheet when I realized I was still naked.

I was still staring at his ass even after I busted. /Especially you/. I believed my roommate was into women, hearing him admit how shy he was about owning up to his fetishes, appreciating the disappointment in his voice when he confessed that he didn't think he could be honest with them. But what had transpired between us was more than satisfying an unfulfilled urge. He liked being sexual with me, insisting that we continue even after I'd tried to cut the interactions off.

/Especially you/. Alex liked me. He liked me more than being best friends at school and living together in the tiny dorm room. He was the one who demanded we be closer. How could he have begged for that if he didn't like me? I fell asleep staring at his ass convinced that my roommate must want more.

My fear flared again when I woke up, all my convictions about Alex liking me excised worrying that he was going to play the regretful straight bro again. I hesitantly looked over to his bed, finding him openly stroking his morning wood. He grinned at me when he realized I was watching.

"Morning, roomie," he said nonchalantly, continuing to jerk his huge shaft. "See, I'm fine. I wasn't kidding about us starting every day like this together."

Even watching him work his eight inches, hearing him reassure me, I was still nervous that the mood could shift at any moment. What if getting off another time would be the trigger for him to start acting like an asshole?

"Dude, I know you're hard over there. You should rip that fucking sheet off and bust with me."

My solid dick was throbbing, pleading for attention from my hand, quickly overwhelming my concerns. I wanted this as much as he did. How could my roommate ever prove that he really was fine, that he really did like me, if I never gave him the chance? I stopped doubting him and decided to go for it, pulling the sheet away from my hard cock and facing Alex again.

"Yeah, there you go!" he encouraged. "Come on, get off with me."

I gripped my solid shaft and started jerking off, Alex watching me as I watched him. His rigid dick looked magnificent in the bright morning sunlight, but I was definitely picturing him conquering the massive gray plug, hearing his blissful moans, remembering how our loads had crossed together in the air.

"What are you thinking about?" he wondered, his voice almost seductive.

"You riding that big plug," I answered honestly.

Alex grinned. "You thought that was hot?"

"Really fucking hot."

He began stroking even more vigorously. "You have no idea how good it felt to finally get that one stuffed all the way inside me, man. So fucking awesome. I can't wait for us to do it again."

Instead of freaking out, my roommate was jerking off with me and already talking about repeating the toy session. Maybe he really was comfortable with everything happening between us, aside from the one bad reaction I'd suffered through after he busted on my face. How could I fault him for that? If I sprayed my load all over a girl's face and liked doing it, felt myself wanting to do more with her, that undoubtedly would have freaked me out too. I'd be questioning everything I thought I knew about my sexuality, maybe even lashing out.

"Getting so close remembering having that toy buried in my ass," Alex murmured. "You there to see me take the big motherfucker. Fuck, dude. You ready to shoot?"

Seeing him urgently working his cock, biting his lip as he looked over at me, I was instantly on the edge. "Yeah," I whispered.

"Fucking shoot it," he growled. "Bust that fucking load with me."

My roommate started grunting and I saw the ropes of cum splattering out of his dick, painting his firm, hairy chest and flat stomach. That pushed me over too, an orgasm surging through me as my load sprayed all over my naked body.

Alex sighed contentedly across the room, planting his hands behind his head as his shaft softened, his biceps bulging out. "Seriously, we should do this every fucking day, roomie," he muttered longingly. "Wake up and take care of our hard dicks. Do it again when it's time for bed. I'd love that."

That's exactly what we did for the next few days, Alex seeming thrilled to have someone he could share getting off with. We always watched each other jerking off, but he didn't try anything bold again, never asking to shoot all over my face or looming over me to shove his armpit against my nose. I felt like we'd established where the lines needed to be to make the situation work, until my roommate's ass had finally recovered from hilting the huge gray plug.

***

"I'm horny," Alex declares from his bed, about an hour after we'd eaten dinner together in the dining hall downstairs.

I don't even look up from my laptop, now that he was shamelessly jerking off with me at least twice a day and we were both almost always naked in the room. "That's cool," I answer.

"Like really horny," he says more urgently. "Would you be down for another toy session tonight?"

Now I actually glance over at him, my roommate lying in his bed with an obvious hard-on. I'd been obsessively thinking about him riding his toys literally every single time we jerked off together. "Yeah, I'd be down," I agree immediately.

He grins, leaping out of his bed and kneeling down beside it, his big furry globes poking out as he pulls his box of toys out from underneath. "How about we do something a little different this time?" Alex proposes, peering back at me. He holds up a long black double-ended dildo. "You like getting fucked too, right? How about we both take this together tonight?"

Take it together? I'm not even sure how that's going to work. I stand up and join my roommate beside the box anyway, definitely intrigued by the scenario but hesitant knowing that he'd spent fifteen minutes cleaning himself out the first time. "That would be hot, but I honestly don't know anything about...you know, cleaning out," I worry.

"Did you take a shit today?" Alex asks like the question is completely normal.

I'm totally unaccustomed to being asked about my bathroom habits, my head instantly recoiling. "What?"

He laughs at me. "You heard me. Seriously, man, did you take a shit today?"

"Yeah," I answer, feeling insanely embarrassed as my face flushes.

Alex chuckles again. "You're probably fine taking something small but I can show you how I clean." He lifts up and bounds toward his closet before I can object, reaching for his water bottles and turning around with them in hand. "So I set my backpack down beside the shower and sneak these in when no else is looking," he explains. "You turn the water on so no one can hear what you're doing, and then you just shove the end of the small bottle up against your hole and squeeze a little water in. Seriously, just a little. A little goes a long way. Push that back out and keep repeating until the water coming out of your ass is good."

I'm horrified imagining myself actually doing that, immediately feeling hesitant, but I really, really want to find out what using that double-ended dildo together will be like.

He sees the doubt on my face. "Or we can just do something else tonight," Alex suggests, sounding disappointed.

"No," I instantly object, imagining sharing that long black dildo with him, the toy buried in both our asses at the same time. "I'll try it."

Alex grins as I stand up, retrieving a few water bottles from his closet and handing them to me. "Seriously, small squirts. Too much water will fuck you over, and you're definitely not going as deep as I am tonight."

The whole discussion is terribly awkward, but knowing that he's planning to take more than the relatively thin dildo instantly hardens my cock. "Small squirts," I repeat.

He laughs seeing that I'm turned on, dropping his water bottles into his backpack as I do the same. "Dude, we're going to have so much fun tonight! It's going to be totally worth it!"

I grab a pair of underwear out of one of my drawers, pulling them up over my legs, intending to go to the bathroom fully dressed like I always did.

"Just go out in a towel, roomie!" Alex chides.

I turn to see that he has a towel wrapped around his waist, his backpack already slung over his shoulder.

"You have such a nice body. Why hide it? We're all guys on this floor."

Hearing my roommate say that I have a nice body makes my dick even harder. I drop the underwear down, just reaching for a towel instead.

"Yeah, show it off, man!" he encourages. "Be proud! Who the fuck cares?"

My dick gets even harder draping myself in the cotton fabric. I'd been scared to me authentic self ever since he'd moved in, until we'd both learned the truth about each other, but I like the way he pushes me. Alex makes me feel like I shouldn't care about what other people think, even if he doesn't quite live that reality with the women in his life. It's so freeing.

We cross into the hallway clad in towels, both of us wearing our backpacks, but I don't even feel conspicuous being with him. Who cares about what we're doing? The bathroom is mostly deserted when we walk in, a couple shower stalls running. We take neighboring stalls, Alex shooting me a grin as we unload the contents of our backpacks with no one looking.

I tried to follow my roommate's advice exactly and the process was easier than I expected. I turned the water off, pulling my backpack beyond the curtain while I was still sopping wet, loading the bottles Alex had supplied back in before I start to dry myself off. Stepping out, I realize Alex is already gone. He's such a fucking expert at all of this.

I trudge back to the room draped in just a towel for the first time ever, not feeling ashamed at all after my roommate had complimented my body. We're all guys on this floor. Who cares?

Alex is there waiting for me when I return, looking excited as he spreads a clean towel out across his bed. "Everything work out in there?" he asks.

"Yeah," I answer with a smile, excited about what's going to happen.

Alex smirks at me, climbing into his bed with the black double-ended dildo in hand. His dick is at full mast as he plants his feet on the towel with his legs raised up, patting the space across from him. "Get up here, man! Grab the lube out of my dresser."

Apparently we've graduated from the floor to the more intimate space of his bed. I'm giddy as I step over to my roommate's dresser, plucking the bottle of lube from his drawer, handing it to Alex before I join him on the towel and match his stance. I settle far enough away that we aren't touching, even though it seems like an inevitability.

Alex has a hungry look in his eyes as he covers one of the ends of the dildo with lube, smearing more into his crack. His face is fixed with concentration as he pushes the toy against his hole, grunting as he starts to slide it in. He moans softly as he easily swallows up half the dildo. "When's the last time you had something in your hole?" he asks.

My obsession with him had been interfering with my sex life all semester. I'd only been fucked twice, the last time more than a month ago. "It's been a solid month," I admit.

"Damn, dude! I'm going crazy after a couple days if I don't stuff something up there!" Alex squirts lube all over the second half of the toy, more generous splashes than he'd allowed himself, pressing the bottle up to my hand. "Put some on your hole too."

I lube my ass up, taking hold of the dildo that's already half-inserted into my roommate's butt and pressing it into the much less practiced tight ring of my ass. "Shit!" I whimper as the head breaches me, my ass stinging. I still can't believe he makes this look so easy.

"You've got this," Alex encourages, peering serenely into my eyes. "Let yourself get used to it. This is going to be so hot, dude."

The pain retreats and I'm able to take more of the toy, sliding my body closer and closer to my roommate as I bury more of the length inside myself, my legs finally coming to rest against his thighs, my bare feet touching the massive mounds of his butt. Our asses are almost lodged together, just a few inches of the dildo separating them.

"This is so fucking hot," Alex hisses, almost looking depraved. "Let me know if I'm being too rough." He reaches for the plastic length exposed between us, gently fucking both our holes as he starts to buck his hips, both of us moaning.

Finally being penetrated again feels amazing, especially knowing that it's my roommate's hand driving the toy in and out of my ass. "Yeah, fuck me," I murmur. I'm imagining that it's his dick inside me, railing in and out of my guts, as Alex gradually increases his pace.

"Yeah, man? You like that?" Alex asks, fucking us even harder with the double-ended dildo.

"I love it," I whisper, my moans growing increasingly enthusiastic, the pleasure in my hole rising with every stroke.

He lets go of the dildo and grips his rock hard dick, bucking his hips more wildly, the toy sliding around inside both of us. "Fuck yeah, this feels so good."

I begin to stroke my own solid cock, loving the sensations in my ass, when my roommate lets go of his shaft and grips my ankles with both of his hands, slamming himself hard into the toy. We're both moaning more intensely, his balls slapping against mine with the forceful thrusts of his body, the gap between us steadily closing.