My Roommate's Toy Box Ch. 03

Alex looks pleadingly into my eyes. "Want to jerk me off, dude?"

His bold invitation surprises me, but how could I say no? I'm nervous as fuck reaching my hand to his rigid dick, wrapping my fingers around his beautiful eight inches for the first time. He's warm and throbbing, a steady stream of precum leaking out of his tip. I start working my cock harder than ever, both of us now throwing ourselves into the dildo.

Alex is staring at me with a lustful, frenzied glint in his mahogany eyes. "You like touching my dick like that?" he whispers.

"I fucking love it," I grunt back.

He smiles. "Yeah, man, me too," he says more gruffly. "Fuck yeah. Jerking us both off with both our asses stuffed. Fuck!"

Hearing the zeal in my roommate's voice, with the dildo scraping against my prostate, almost sends me over the edge. He'd fantasized about doing this with someone, assuredly imagining sharing the experience with a girl, but I'm so happy he's doing it with me.

Alex laughs at me, noticing that I almost busted. "Let's try a different position," he suggests. "Get up on all fours."

I reluctantly let go of his dick, Alex backing away from me, his hairy hole gaping open as the dildo withdraws. He slowly pulls the toy out of my ass, turning on to his hands and knees with his legs spread wide apart. He immediately starts pressing the length into his slackened opening as I climb up into the same position, backing my butt toward his, our legs touching together on the mattress. I twist my head around and see that he's already taken his half of the toy.

"Grab the other end and go for it," he urges, his face turned to mine.

My roommate looks on, his eyes still lustful, as I grip the dildo and let the head breach my hole again, sliding my ass back. My butt is hungry to be filled now, and I take the length easily on my second try, moaning gently until my cheeks press against Alex's massive mounds, the whole dildo buried between us. "Fuck, Alex," I groan, both of us still looking at each other.

"This is so fucking hot!" he says excitedly, turning his head away and starting to thrust his ass against mine, his big ass bouncing into mine as we both start moaning fervently together. "Fuck yeah, man. God this is incredible."

We take turns fucking ourselves on the long black dildo, our asses drawing back and then slamming into the long toy, the bare skin of our cheeks clapping together every time as we alternate thrusting into it. An endless stream of impassioned groans and curses are steadily slipping out of both of us as our assaults on the dildo grow more frenzied. I'd never in my life pictured doing anything like this, but it feels incredibly intimate to be sharing the object, to have our butts continually slapping together as we work our ravenous holes. Eventually we both come to a rest, both of us breathlessly panting with the whole dildo still buried between us, our cheeks pressed together.

"That was hot as fuck," Alex growls from the other side his mattress. "Dude, I think I'm ready for something thicker. You game?"

I twist my head to look at him and he's grinning at me like it's a challenge, my ass feeling greedier than ever. "Yeah, I'm definitely game!"

Alex pulls his butt away from mine, the dildo sliding out of me, reaching his hand back to wrest the toy from his hole. He jumps off the bed, setting the double-ended dildo on the tile floor and kneeling over his toy box. "Come on, come pick something else out!" he invites.

I join my roommate on the ground, my hole longing to be filled as I survey the options spread out beneath us. I'm feeling curious about the bigger items, after witnessing Alex's blissful reaction to being stuffed with them, but I know I'm a total beginner compared to him. My eyes focus on a more dick-sized toy, a black silicone plug that's shaped like a cone and definitely thicker than dildo we'd hilted together. I point at it. "That one, maybe?"

Alex picks it up, stroking his fingers against it. "That's it, man?" He glances at me and smirks, pressing the plug into my hand. "You know I'm going to need something way bigger than that." He gazes back at his collection, picking up another plug that's easily twice as big as the one I'm holding.

I really want to watch him hilting the monsters again, but I don't object. "So how do you want to do this?"

"Let's get on the bed again," he decides. "On our backs like we were before." He rises up and settles at the center of his mattress, splaying his big, hairy legs out with the huge plug in his hand.

I climb back into my roommate's bed, my legs crossing over his. We're touching again like it's nothing, after I'd stroked his dick and our asses had violently collided together. He has to like touching me. How could he be fine with any of this if he doesn't like touching me? I try to stifle my thoughts. I don't have to understand him to share this experience with him right now. My roommate has been slowly revealing himself to me all along, and I know that's the best way to discover what he really wants.

"Fuck it, man," Alex mumbles. "I want something even bigger after what we just did." His hands press against my legs, throwing them up into the air, his vision shifting to my ass. "You have a sweet fucking butthole, roomie," he hisses, as he slides out from underneath me and climbs up.

Now he's complimenting my hole? I try not to think too much about his words, catching a glimpse of his massive furry globes before he kneels down in front of the toy box again.

Alex returns with an even bigger plug gripped in his hand, settling across from me and folding his legs over mine. He grabs the lube and coats the massive toy, reaching the bottle out for me to grab.

I take the lube and follow my roommate's lead, slicking up the black plug and positioning it against my hole. I'm desperate to be stuffed again, but I'm still slightly dreading pushing something thicker than the double-ended dildo into my ass, knowing how much it had stung at first.

"Go for it," Alex encourages, looking intently at my butt. "Shove that thing in!"

His enthusiasm and lustful stare is the only motivation I need to overcome my doubt. I push the tapered end of the plug into my loosened hole, groaning as the thicker part starts to slip inside me.

"Yeah!" Alex growls. "Take it! That's so fucking hot!"

I'm struggling with the extra thickness of the fat end, but I force the plug deeper anyway, feeling my ass stretching wide around it. My insides quickly yield, a whimper escaping my mouth as the toy sinks all the way into my hole, the thin neck slipping into me. I sigh contentedly, my fingers tracing over the circular base now lodged against my spread opening.

"Yeah, you fucking got it!" Alex murmurs. "You like having your ass filled up?" He's still holding his significantly bigger plug against his crack after eagerly watching me insert mine.

"Feels good," I whisper, still getting accustomed to the sensation of fullness. "You afraid to take that thing?"

He plunges the ridiculously huge plug into his hole like it's nothing, his ass instantly swallowing it up to the base. "Nope," Alex says with a grin. "Trust me, that was way too fucking easy."

We start to fuck ourselves with the plugs, our legs still touching as we're both moaning, Alex gradually creeping closer to my body, steadily lurching himself forward as he pulls the plug in and out of his ass. Eventually his thighs are on mine, our solid dicks inches apart. My roommate lifts his torso up off the bed, bracing himself with one hand as he looks at me lustfully. He grabs my dick for the second time ever, staring into my eyes as he strokes my hard shaft.

"Grab mine again too, dude," he invites.

This time I feel totally confident wrapping my hand around his rigid eight inches. He likes me touching him. He must like me touching him.

"Yeah," Alex breathes, his eyes closing as his head sinks back, his hand still stroking my cock at the same time. "That feels so fucking good." We're jerking each other off like it's the most natural thing in the world, our plugged asses almost shoved together. "You like this?" Alex asks, his eyes suddenly gazing into mine again, his hand relentless on my cock.

"You know I do," I whisper, loving his fingers on my shaft.

He smiles. "Me fucking too, man. Your body feels so good on mine. Why is hooking up with a chick never this hot?"

I laugh nervously, terrified that we're crossing into "I'm not gay" territory. "Well, I definitely wouldn't know anything about that."

"I like doing it," Alex adds quickly, still jerking me off. "I really do like fucking them sometimes. But finding a girl who's willing to play with your ass...that's like hunting a fucking unicorn. I never know how to bring it up."

"That sucks," I mutter. "You have to be honest if you're going to find what you really want, though." Are we seriously having this conversation as we're stroking each other's cocks with toys shoved up our asses? I can feel my boner starting to retreat, the magic slightly fading hearing about how much he wants to find a woman who can take my place.

Alex sighs. "You want to hear something honest? I never thought I would like playing with another dude's dick this much. It's different, but it's not bad."

That instantly firms my cock back up. I feel an overwhelming need to reassure him. "I think you get off on stuff that's forbidden," I suggest, trying to make my roommate comfortable again.

He bites his lip. "Yeah, I guess that's true. I like being adventurous." Alex is quiet for a minute, our hands still working our shafts. "Would it be weird if you touched my nipples?"

I know he wants me to do it. The second I let go of his dick to reach for his pierced nipples, Alex closes the rest of the gap between us, almost sitting in my lap, the hairy globes of his big butt resting on my thighs. He presses our cocks together, working both of them with his hand, as I stretch my arms toward his chest. I gently touch the metal balls at the ends of the barbells, letting my fingers glide to Alex's pink nipples and tracing over them, slightly squeezing

Alex lets out a soft moan. "Yeah," he whispers, jerking our cocks more vigorously. "Dude, that shot a fucking bolt of lightning through my dick just now. You can be rougher with them."

I'm already elated to have his ass against my skin, to have his fingers sliding up and down my shaft, but knowing that I'm giving him extra pleasure turns me on more than anything else. I squeeze his nipples harder, Alex emitting a louder moan and moving his hand more urgently on our dicks.

"Bet your mouth would feel even better," he says right to my face.

My heart starts pounding harder than it had been the whole time, feeling like the situation is escalating even more. "We'd have to get a little closer."

Alex grins, releasing our cocks and leaning forward to reach his arm around my back, pulling me up into a sitting position as his bare feet wrap around my ass. He plants both his hands behind himself on the bed, now literally sitting in my lap. Our faces are inches apart, his full, luscious lips closer to mine than they'd ever been before. I want to kiss him so fucking badly.

"Better?" he asks.

"Much better," I whisper back, twisting both his nipples again.

"Fuck yeah," Alex says excitedly. "Do it, man. Lick them, suck them."

He wants my mouth on his body and I can't say no. I press my face down into his defined pec, wrapping a hand around his toned back and lapping my tongue against his nipple. I start stroking his solid cock again at the same time.

"Yeah," he murmurs into my ear. "Fuck, dude. Don't hold back. Rougher."

I start sucking on his nipple, gently biting it, Alex moaning more heatedly as I steadily bite him harder. I repeat the same treatment on the other side of his chest, and when I lift my head away from his body, my hand still on his back, he's staring into my eyes. I immediately recognize the longing on his face, absolutely certain that he wants to kiss me. I wait for the next "Would it be weird" line as we're silently looking at each other, my roommate literally sitting in my lap, but the words never come. I decide to take the initiative, leaning into him, pulling his body into mine, Alex closing his eyes as our lips join together. He kisses me back softly at first, the intensity swiftly escalating from gentle pecks to intense, fervent kisses, Alex moaning quietly into my mouth. His strong tongue parts my lips and swirls eagerly against mine, both of us digging ferociously deeper into each other. We make out desperately for several minutes, my hand drifting up from Alex's dick and joining the other at his back, both of them steadily shifting up to his head, ravenously pulling his face into mine.

Alex is grinning giddily when he finally breaks the kiss, my hands dropping away. "Now that was definitely weird." His expression shifts as he seems to ruminate on the fact that we'd just eagerly made out with each other.

I look into his gorgeous brown eyes, afraid he's going to tear away from me at any second now that he's doubting himself. "If it was, I really love being weird with you, man," I say. I'd felt him enjoying it the whole time, loving every moment, but he suddenly appears uncertain.

Alex is stone-faced as he abruptly lifts off of me, both of our holes still plugged, and I feel like it's all over when he climbs out of his bed without saying a word, letting my body sink down into his mattress.

"Tyler, get down here!" he demands. "I need something bigger in my ass!"

Maybe Alex had panicked a little realizing how much he liked kissing me, but he obviously doesn't want to stop. My head jolts back up, my gaze shooting hopefully to him. My roommate is pulling the insanely girthy dildo I'd first caught him riding from his toy box, lodging the suction cup against the floor. I realize the plug that had been in his ass is already sitting next to the double-ended dildo.

"You ready for something bigger too?" he asks, turning to look at me and seeming calm. "Come on, man, you know you are!"

"You have a suggestion for me?" My hole is stretched open and relaxed after holding the plug inside for awhile, and I'm definitely curious about pushing my limits. I lift up, letting my legs hang over the edge of my roommate's bed.

Alex trudges back to the box, bending over and holding up the same nine inch flesh-colored dildo that he'd warmed up with during the first session, the thing certainly significantly thicker than a real cock. "I bet you can handle this one now," he says, pushing the toy into my hands.

The dildo is undoubtedly bigger than anything I've ever had in my ass, looking larger than it had appeared when I first sighted it from across the room, but at least I can actually wrap my fingers around the shaft. "You really think I can take this one?" I ask, feeling suspicious. I know I won't be able to swallow it up as easily as my roommate had.

He laughs at me. "If you believe you can take it, you can take it, trust me. But yeah, the widest part is about the same size as the widest part of the plug in your ass right now. You can do it, dude."

I'm still doubting my hole can swallow up something this huge, but I'm willing to give it a try. "Ok, but I'm getting something smaller if this is too big."

Alex laughs again. "There's no such thing as too big! Come on, get across from me. Let's watch each other riding." He grabs the bottle of lube, settling into a squatting position over the monster resting on the floor.

I step back toward my bed, sticking the comparatively modest dildo in my hands to the tile. I squat over it like Alex is doing, his hands rubbing lube all over the girthy shaft of his huge toy. I let the plug still buried inside me shoot out of my ass, catching it with my hand,

Alex is chuckling, smiling as he passes me the bottle of lube. "Nice little gape you have going there. This is going to be so fucking hot!" he says excitedly.

Rubbing lube all over the thick dildo beneath me, I think about the advice my roommate had offered: if you believe you can do it, you can do it. I need to stop doubting myself. I want him to be impressed and turned on watching me sink my butt all the way down on this thick toy.

"Ready, dude?" Alex asks, that depraved look planted on his face again. "Let's do it." He's staring into my eyes, biting his lip as he instantly sinks halfway down on the beast I'd first caught him riding, grunting loudly as he halts.

I know he's waiting for me. I take a deep breath, reassuring myself that I can do this, letting the tapered head of the nine inch dildo sink into my hole. I gently lower myself down on the length, the toy easily penetrating me until I reach the thick middle, my insides suddenly burning. I wince and close my eyes, a groan of discomfort escaping my mouth.

"Just relax right now, man," Alex reassures me, noticing that I'm struggling. "What do you think I'm doing? Let your ass get used to having that big dildo inside you." He doesn't wait, sinking all the way down to the balls of his behemoth, groaning furiously as he hilts it.

My ass is still stinging with the middle of the thick shaft lodged inside me. I'm doubting I can take more without working up to it, ready to ask my roommate for something smaller.

"Kiss me," he whispers.

My eyes flutter open to find Alex looking dead serious, the longing expression spread across his face again. I swallow hard, thinking about how he'd reacted the first time, afraid to lean into him again now.

Alex sees my reluctance, planting one of his hands on the floor and drawing his head toward mine. "Kiss me, man," he says like he's begging.

I gulp and sweep my hesitance aside, pushing my face toward his. Our lips almost meet when he turns his head away, our faces brushing together.

"Shit, sorry," he mutters, facing me again, looking intently into my eyes, his warm breath against my lips. "That was such an amazing kiss, seriously. Please kiss me like that again."

"Are you sure, Alex?" Seeing him turn away from me, uncertain about what he really wanted for a moment, I feel like we're fucking things up again if we do this.

His lips press against mine with no hesitation, kissing me roughly, passionately, until his face barely lifts away. "Yeah, I'm sure," he whispers, immediately starting to kiss me even more fervently, his tongue quickly slipping into my mouth.

I'm too lost in the moment to obsess over what might happen next. My roommate is even more inviting than he'd been the first time, our tongues desperately twirling together as we ravenously make out. Feeling completely comfortable and totally relaxed, my ass calm, I plunge my hole down further on the dildo with Alex's tongue buried in my mouth, sinking until I feel the balls resting against my cheeks, softly grunting his mouth.

He pulls away, looking down and seeing that I'd bottomed out on his nine inch dildo. "I fucking knew you could do it," he breathes into my lips, wrapping his hands around my head and starting to devour my mouth again, more intensely than he had all night.

My roommate is kissing me more eagerly than anyone had ever kissed me in my whole life, his tongue exploring me like no one ever had before, both of us moaning into each other until he pulls away.

Alex grins and shakes his head. "Yeah, no fucking regrets about that. I'm so turned on, man. Let's ride these big cocks together!"

I'm missing his tongue already but I can still taste him in my mouth. Looking down, I realize my dick is rock hard. Glancing over at Alex, I notice that his is too. No matter what he says later, I'll know that he enjoyed that kiss. He starts fucking himself with his massive dildo and I follow suit, amazed that I'm actually comfortably accommodating the thing. His kiss was all I needed to relax, to surrender and let myself enjoy this feeling.