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It had started as a joke.
That Christmas, Lando had tossed him a gift bag tied up in a ribbon, and inside, sitting like some kind of punchline, was a strawberry lube bottle and a dildo. Oscar had laughed, red-faced and awkward, but underneath it all, it had stung a little. Because back then he was still fumbling, still figuring himself out, still skittish every time another man got too close. And Lando, well, Lando had always known exactly where to stick the knife.
Five months later, not much had shifted. His luck hadn’t exactly turned around. But at least he wasn’t walking around with the weight of being a gay virgin anymore. He’d let a good handful of men into his bed since then, clumsy encounters that were still better than anything he’d ever had with girls. He hadn’t bottomed yet, and maybe he wasn’t ready for that, but it didn’t matter. It was still better. It felt more right.
He was only looking for his old glasses. That was all. But when he dug into one of the boxes stacked in the corner of his room, his hand brushed the same Christmas gift bag.
The paper was still there, wrinkled around the edges but mostly intact, like it had been waiting untouched since the day Lando had shoved it into his hands with that infuriating grin.
He should’ve left it where it was. Instead, he opened it.
The box inside was exactly as he remembered: glossy, sealed, heavy in his palm. His pulse thudded unevenly as he slid it free, and then there it was. The dildo. Brand new. Never touched.
Oscar stared at it, the way the silicone caught the light, textured like real skin, weighty and solid. Not some exaggerated parody of a cock, but big enough. Bigger than his own.
Heat crept up his neck as memory flashed. He could almost hear it again, the way Lando had laughed when he’d shoved the box into his hands, voice pitched somewhere between a joke and a dare. “Looks about my size, don’t you think?”
Oscar had rolled his eyes back then, muttered something defensive, but now… staring at the toy, at the way it dwarfed him, the words landed differently. They lodged under his skin, humming with possibility, with comparison.
And suddenly he was burning, face scarlet, the weight of the silicone in his palm pulling him straight back into that moment. Lando’s knowing grin, like he’d planted the thought there on purpose.
Lando was his goofy, reckless, endlessly extroverted bisexual roommate. Of course Oscar had seen his cock before. A towel slipping at the wrong moment, drunken nights when neither of them cared about boundaries, the kind of accidents that came with living in each other’s pockets. At the time, it hadn’t mattered. Just one more thing to ignore, to laugh off.
But after Christmas, after Lando had made that comment, things shifted.
Oscar had started noticing. Not deliberately —he wasn’t a creep— but it was impossible not to register the proof when it presented itself. And Lando hadn’t been bluffing. He was bigger. Definitely bigger.
Oscar turned the toy over in his hand, staring at it like it might answer the question for him.
He’d never bottomed before. Not once. But that didn’t mean he hadn’t… explored. Every time he got himself off in the shower, his fingers would wander, slipping inside, brushing against his prostate until his knees nearly buckled. Two fingers, sometimes. A press, a curl. Nothing rough, nothing daring. Just enough to feel the spark, to tease the edge.
But this, this thing in his hand, was nothing like that. It was so much bigger than the hesitant press of two fingers. And yet… His throat worked as he swallowed, heat flooding low in his belly, the question rooting itself deeper with every second he looked at it.
Should he?
Should he even try?
Every now and then, Oscar had wondered what it would feel like, if he could even take a cock inside him at all. The thought always came in fleeting sparks, gone before it could settle. He was too afraid to try.
But now, with that size of the toy in his hand, the thought shifted.
Could he take this ? Could he take Lando ?
Back then it had been a joke. Now, staring at the toy, it didn’t feel like one at all.
He pictured it too easily. Lando, hard and heavy, pressing into him, stretching him wide until his body gave way. The thought alone left him burning, shame and want knotted tight in his chest, heat sparking everywhere.
And the worst part? He didn’t know if the flush in his cheeks came from fear, or from how badly he wanted it to be true.
Before he could talk himself out of it, Oscar set the box aside and climbed onto his bed, dildo and lube clutched in hand. His clothes came off in quick, fumbling motions until only his t-shirt clung to him, thin cotton brushing against overheated skin. Somehow keeping it on made him feel less bare, though nothing about this felt safe anymore.
He snapped open the bottle, the ridiculous strawberry-scented lube that had come with the gift, still sealed until now. And the sugary smell filled the room. It made him think of Lando instantly, because of course Lando would choose something like this, sweet and stupid and impossible to ignore.
Oscar slicked his fingers and spread himself open against the pillows, the cool drag of lube making him shiver. He started as he always did. Slow, careful, two fingers pressing in, curling until his breath caught. Pleasure shot through him, familiar and grounding. But it wasn’t enough.
He thought of Lando’s hands as he worked himself open. Lando’s fingers, long and thick, the way they’d swallow Oscar’s in a handshake, how small his own felt in comparison. His broader palms. Stronger. The thought alone made Oscar’s cock twitch where it lay against his stomach, already wet and leaking, precum smearing across his skin and his t-shirt in sticky trails.
With a shaky breath, Oscar pushed in a third finger. He worked himself harder, faster, the obscene squelch filling the quiet room until he was trembling, the need to finish almost overpowering him. He nearly gave in, nearly wrapped his free hand around his cock to come and forget the rest, too embarrassed to keep going.
But then his gaze landed on the dildo beside him, waiting. Daring him.
He couldn’t stop.
Even though he wasn’t sure he was ready, even though fear crawled at the edges of his mind, he reached for it. His hand trembled. The toy looked massive compared to his fingers. Too big. Too much.
But then Lando’s voice slid into his memory again. Looks about my size, don’t you think? And Oscar’s hole clenched around nothing, a hot pulse of want ripping through him, precum spilling down his cock.
He slicked the toy thoroughly and pressed the tip to himself. The first push made him gasp, his breath catching on the burn as his body struggled to take it. Inch by inch, painfully slow, until his eyes squeezed shut, chest heaving with shallow breaths. It stung, but in a way that made his toes curl, made him crave more.
He forced himself further, easing the toy halfway in before stopping to breathe, to adjust, trembling as the fullness spread through him. Then he pulled it out, just to push back down again, slower, deeper, until the base of the dildo pressed flush against him.
And in his head, it wasn’t silicone. It wasn’t a toy. It was Lando. Lando, heavy and solid above him, cock sinking deep, grin wicked and triumphant as he told Oscar to take it.
Oscar gasped, hips tilting, chasing the pressure, chasing the stretch, the pressure, the unbearable fullness. He stayed like that for a moment, legs spread wide, trembling, the toy buried all the way inside him, his chest rising and falling in sharp, unsteady breaths. The size was almost cruel, pressing against his prostate with a steady weight that left him shivering.
It was too much. But it was perfect. And he didn’t know if he wanted to cry, or to come.
Oscar held his breath as pulled the dildo back. The stretch made him whimper, his body clenching as the dildo slid partway out, slick and heavy, before he pushed it back inside. Deeper. The pressure hit right against his prostate. His lips parted on a sharp sound, breath tearing free, “Fuck—” It was shaky, ruined, the word spilling out of him before he could stop it.
His free hand twitched toward his cock, desperate to wrap around the dripping length, to stroke himself into release right there. But he stopped short, shame and stubbornness knotting inside him. He didn’t want it to end that quickly, not when it finally felt like this. Not when it felt like Lando.
With a broken groan, Oscar rolled to his side, reaching for the pillow and yanking it close. He shoved it under his hips, pressing down hard until his cock was pinned, throbbing against the fabric. His fist tightened over it, grinding down to keep himself from tipping over too soon.
Then his other hand reached back again, curling around the base of the dildo as he started to move it. Slowly at first, easing out, pushing back in, each thrust sending another spark right through his core. The more it pressed into his prostate, the louder his breath got, gasps breaking into sharp, helpless moans.
His wrist ached, strained with the motion, but the pleasure swallowed it whole. He couldn’t stop. He wouldn’t.
He built a rhythm, faster now, rocking down onto the toy, thighs quaking with the effort. Each thrust made his cock leak fresh trails of precum against the pillow, dampening the fabric. His thighs shook, muscles burning, and still he kept fucking himself down onto it, harder, deeper, until instinct had his ass lifting to meet the thrusts, grinding, chasing a phantom weight that wasn’t there.
But in his head, it was.
In his head it was Lando pressing into him. Lando stretching him open, hips snapping forward, his voice low and smug in Oscar’s ear telling him to take it, telling him he could. That grin burned behind his eyelids, sharp and knowing, as if Lando had planned this from the start.
Oscar bit down on the pillow, muffling the broken cry that tore from him as the toy hit deep, right against his prostate again.
Oscar swore he could feel it. Lando’s breath ghosting hot against his ear, the solid weight of his chest pressed flush to Oscar’s back, the relentless snap of his hips pounding him open. It was him. Lando, thick and hard inside him, filling every inch until Oscar’s body could do nothing but give.
The fantasy broke him.
With barely a friction from his pillow, Oscar came with a strangled cry, his cock jerking violently as cum spilled in thick streams across the grey fabric. It soaked quickly, spreading damp beneath his stomach, and he trembled with the force of it until he could barely breathe.
But he didn’t stop.
Even as his orgasm tore through him, even as aftershocks wracked his body, Oscar kept moving the toy inside him. Each thrust hit that spot again, dragging more sounds out of his throat, strangled moans that sank into the pillow he clutched tight. His wrist ached, screaming with the effort, but he forced himself to keep going, chasing the overwhelming high.
It was too much. It bordered on agony. And yet the sting, the overwhelming fullness, the way his body convulsed around the intrusion… he was addicted to it already.
He shoved himself harder, hips jerking helplessly, overstimulated beyond reason, tears pricking at the corners of his eyes. His cock twitched against the ruined pillow, leaking more.
Only when his arm gave out, wrist weak and fingers shaking, did he collapse forward, face pressed into the damp fabric. The dildo stayed rooted inside him, plugging him full, his body clenching reflexively around it even as his muscles sagged with exhaustion.
Oscar melted into the mattress, chest heaving, sweat cooling sticky on his skin. And all he could think, as the world blurred into haze around him, was Lando .
For a while, Oscar stayed collapsed. Every nerve felt raw, sparking from the inside out, his body too overstimulated to even think straight. He kept telling himself he was done, wrung out, finished.
But the toy still sat buried inside him, and his hole wouldn’t stop clutching down around it. Each tiny spasm, each involuntary twitch, sent another shock through him.
It wasn’t enough. God, it wasn’t nearly enough.
His cock hadn’t softened. It pulsed heavy against his thigh, still leaking like he hadn’t just come, precum smearing damp across his skin. His hole felt stretched, aching, greedy like it wanted more, begging for more, like it would never be satisfied.
With a broken groan, Oscar pushed himself upright, muscles trembling in protest. For a long breath, he stayed on his knees, palms braced to the sheets, letting the dizziness fade.
Then, slowly, he lowered himself down again. The dildo sank back inside him, inch by inch, until he sat on it fully, thighs spread wide. The new angle drove it deeper, sharper, and a broken moan tore from his throat before he could swallow it down.
His fists tangled in the hem of his t-shirt, clutching it up against his stomach as he began to move. Lifting on his knees, then sinking back down. Up, down. Up, down. The rhythm was cautious at first, his body still tender, but the pressure built quickly, the toy dragging against his prostate in a way that left him gasping.
He planted one hand behind him on the mattress, fingers digging into the sheets, and began to ride faster. His body moved on instinct now, the wet slide of the toy, the sharp snap of his hips, the obscene sound of it all filling the room. Each thrust drove him further, harder, his ass rocking back like he was meeting someone there.
And in his head, there was someone there.
The emptiness above him only made the fantasy worse, made it easier to imagine Lando there instead. Lando’s hands gripping his hips, bruising tight, holding him in place as he slammed into him.
Oscar moaned louder, the sound tearing out of him as he fucked himself harder, thighs burning, sweat running down his chest and his back.
The second orgasm hit him without warning, ripped out of him by the steady, punishing drag inside. He came untouched, cock jerking wildly as his hips slammed down, the movement making him bounce on the toy while his cock bounced with it in front of him, heavy and flushed, slapping against his clothed stomach with every thrust. Cum spilled in messy streams from the tip, less this time and weaker, running down his length, a few droplets flicking through the air to splatter across the sheets as his hips snapped down hard.
And still, he didn’t stop.
His body clenched tight around the toy, trembling, every nerve lit raw, but he kept fucking himself through it, each thrust wrecking him deeper. His strength was nearly gone, muscles quivering, until finally he collapsed forward, elbows digging into the mattress. He arched his back instinctively, ass up and offered. Burying his face in the crook of his arm, he muffled the strangled sounds spilling from his throat and let his hips take over, rutting down helplessly.
Just his hips now, driving down, grinding hard, faster, rougher.
His movements turned frantic, hips snapping down with reckless force. Tears stung at the corners of his eyes. His body begged for mercy, but he only drove himself harder, each thrust more punishing than the last. He wanted the ache, wanted the pain, because the pleasure alone wasn’t enough.
Because it wasn’t him. God, it wasn’t him. It was not him.
The sound was obscene, skin meeting plastic, wet and loud, each slam louder than the last. His cock twitched uselessly, already spent, smearing what little he had left against the ruined sheets.
“Fuck,” he gasped into the sheets, the word breaking apart on his tongue. Sweat dripped down his spine, slicking his shirt to his skin.
His hand fumbled blindly until it found another pillow, dragging it under his stomach. He shoved it in place and collapsed onto it, the shift angling his hips just enough that he could keep moving. The toy drove deeper now, pressing into him from inside while his weight ground him down harder.
One hand braced weakly against the sheets while the other pressed low against his stomach. He could feel it from inside now, the thick shape filling him in ways his fingers never had. His cock gave a weak jerk, spilling only a few pitiful drops.
A broken whine tore out of him, high and pitiful. Too much. But still not enough.
His hand slipped lower, abandoning his stomach to wrap around his cock, slick and messy where precum and cum already smeared across his skin. He didn’t stop fucking himself on the toy, hips rutting down as his fist moved ruthlessly, pumping fast, desperate. His cock spat watery strings into his hand but he couldn’t bring himself to care. More dribbled out as he jerked himself, watery and weak, sliding over his fist. The sensation made his stomach clench, made his throat work around another desperate noise. For a flicker of a second, the thought hit him. Fuck, I’m going to piss myself. His body felt wrung out, empty, overstretched, on the edge of humiliation. But the thought didn’t stop him. It only spurred him on.
Because even if he did, even if he soaked himself right there, it couldn’t possibly be more humiliating than this: spread open, overstimulated, dripping, riding a toy like it was Lando’s cock, jerking himself pathetically.
His body was wrecked, trembling violently with every thrust, every jerk of his fist. He was far past his limit, his cock spilling nothing but thin, watery dribbles into his palm. His hand slipped over himself, raw and ruthless, as his hips ground down on the toy again and again.
Tears pricked hot at the corners of his eyes, blurring his vision until all he could see was the damp pillow under his face. He whined into it, high and broken, his sobs muffled against the fabric. His body begged him to stop, but his hips refused, rutting down like an animal, clenching tight around the toy as if it might finally give him what he was begging for.
“Please,” he gasped into the crook of his arm, though he didn’t know who he was begging. Himself. The toy. Or Lando
It hurt. His thighs shook, his wrist ached, his cock leaked pitifully across his knuckles, but he shoved down harder, chasing a release his body had nothing left to give. The overstimulation blurred into pain, pain blurred into need, and all of it tangled together until he was crying openly, soaking the crook of his arm, choking on the noises he couldn’t hold back anymore.
And when it finally broke through him, it wasn’t another orgasm but something else. His body giving way as a small, humiliating stream of piss slipped free, warm against his cock, wetting his hand and the pillow beneath him. Just a little. Just enough to make him sob harder, face burning with shame. But he kept moving, hips jerking, ass clenching desperately around the toy. Tears streaked his face, sweat plastered his shirt to his back, his body convulsing with overstimulation and humiliation and the endless, unbearable need that no release could touch.
But even that humiliating trickle wasn’t enough.
With a sob that cracked in his throat, Oscar shifted again, folding forward until his forehead pressed into the soaked mattress. His shoulders shook, collapsing inward, as his other hand moved down too. He pressed his palm flat and firm against his lower stomach, right where the toy pushed deepest inside him. The added pressure made him choke on a gasp, the sensation blinding, unbearable. Too much, too much—
And then his body gave way.
The strain in his bladder snapped, and everything left in him spilled out in a hot rush. He gasped, shuddering as the piss poured freely, soaking his cock, his hand, the pillow beneath his stomach. It hit the sheets, pooling warm beneath him, spreading until it dripped down his thighs.
Tears stung harder, shame biting deep, but beneath it came something dizzying. Relief hit so sharp, it made his whole body tremble. He whined, high and broken, even as his hips twitched, his hole clenching around the toy like his body couldn’t let go.
The stream slowed, stuttered, until there was nothing left. Empty. Finally, completely empty.
And finally, his strength gave out. His hands slipped away, his body sagged limp over the ruined bed, the dildo still locked inside him, stretching him full. His chest rose and fell in shallow bursts, breath shaking, muscles quivering with aftershocks.
Spent. Shattered. Humiliated. Relieved.
He melted into the mattress, sinking into the mess he’d made, nothing left to fight with, nothing left to give. The room reeked of sweat and lube and sex, cloying and heavy, but Oscar barely noticed. His eyelids fluttered, wet lashes dragging against his skin, the haze of exhaustion dragging him down, down, down.