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It had been raining all day long, flashes of lightening lighting up the dark sky. The sound of rain pounded on the roof of your house for hours on end. Eventually, with a flash of light, the house grew suddenly dark, the storm knocking the power out of your house. It was nights like these that were perfect for you to spend quality time with your love, Skips.
“You sure about this?” You chuckle anxiously. Skips side eyes you as he strips his shirt away from his torso, laughing softly.
“I mean, as long as you’re into it?” He replied, dropping his shirt on the floor before turning back towards where you sat shirtless on the edge of the bed. It was hard to see in the darkness of the room, but luckily Skips gave you the go ahead to light up a candle, just so you could see him just a bit.
“I mean. I really really am, but are you?” He comes closer to you, crawling onto your lap, straddling your thighs.
“We’ve talked about this before, penumbra. I’m into whatever you’re into.” You giggle, your hands reaching up to grab his waist. Your eyes can help but wander, looking down at how his V line tucked into his skinny jeans with a faint happy trail peaking out from above his boxers. And well… you know what they say about happy trails.
“Remind me next time I stumble home drunk to never reveal my kinks to you again.” You glance up at him right as he leans down and begins to kiss and nip at your neck.
“Hmmm, I don’t think so. I think I’ll press further next time.” His hands explore your bare waist, his soft lips nipping at your neck gently. You whine, pulling his waist closer to your own. “Who knows what else you could be into? Unless you think this is your worst one.”
“Ohhhh, definetly not my worst.” Skips pressed a kiss to your cheek, “just, not one most people are into.”
“Well I’m not most people, penumbra.” He presses another kiss onto cheek, making you giggle. You push him away, looking up at him sincerely.
“Okay just know… we can stop at any time. You just have to say.”
“I know. I promise I’m just as into this as you are.” He reassures you with a kiss, holding it for a blissfully long time before pulling away. You smile up at him and run your hands across his chest before pushing him off you and onto the bed. He lands with a soft “oof!”
“Okay then, how big are you wanting to go?” You smile, standing to open your bedside drawer. “I have a large assortment.”
“Oh, I’m aware.” He sits up, watching you as you ruffle around the drawer. You pull out a bottle of lube first, then dug a bit deeper to find the token item, a harness. Skips eyes it, biting his lip, slightly nervous. “Uh… I don’t know.”
“Tell me how you like the feel of this one.” You toss him a decently sized toy, a little on the bigger end and semi-firm. He catches it, a blush spreading across his cheeks as he holds it in his hands. He was familiar with the toy itself, knowing it was one of your favorites. But, he’s never thought about what he’d might like… in him. The size made him swallow thickly before he hands it back.
“Maybe something… smaller? You’ve got to remember I’ve only been on the giving end.” He chuckles as you take the toy back. You nod, searching around the drawer once more before pulling out a decent sized toy, though it was a bit on the thicker side. He takes that one and looks it over, turning it in his hand. “Yeah. That’s much better.”
“We have our winner.” You pushed the drawer back in. He places the toy back down next to him as he watches you shed away your pants, looking over your body. He’ll never get over how hot you looked while exposed like this, your soft thick thighs that your underwear hugged so perfectly. He leans back onto his elbows as you slip on the harness adjusting it slightly to your size. You turn your attention back to Skips, smiling. You slink your way back to him, inserting yourself between his legs, leaning over him. “You look so sexy like this.”
“Yeah?” He flushes, looking away. Your hands find your way back to his hips, suddenly tugging him closer to the end of the bed. He stumbles, almost falling off of his elbows but he stabilizes quickly. You lean down, catching his lips with your own as you start to unbutton his pants. You quickly lick at his lips and he quickly accepts. He greedily laps at your tongue, sucking gently. You unzip his pants and snake your hand into them, groping him through his boxers. He was so hard under your hand, the feeling of your warmth against his cock making him moan into your mouth. That’s one thing you always loved about having sex with Skips, he was always so vocal.
You pull your hand away briefly, reaching into his boxers to untuck his cock from their cloth prison. You pull away from the sloppy make out session to latch onto his neck, kissing and sucking harshly. You quickly wrap your hand around his shaft, starting to jerk him at a good pace. He moans, tilting his head back to allow more access to suck a hickey into his soft skin. “F-fuck…” he mumbles.
You continue to rub his shaft, his cock feeling heavy against your hand. Your thumb moving across the his tip, swiping away the precum that began to accumulate there. You pull away from him for just a moment, admiring the way his hard cock pressed against his stomach, precum leaking onto his abdomen as he looks up at you, flushed and panting slightly. “Take off your pants.” You demand.
He smirks at your sudden dominance and does as he’s told, his thumbs hooking on the waist band of his boxers and pants, quickly sliding them down swiftly before kicking them off with your assistance. You immediately re-situate yourself between his legs, kissing him passionately again. You blindly fumble for the lube, slamming the bottle next to him as you further press yourself against his body. Your hands wander his body, feeling all the way up from his hips to his waist to his torso, your thumbs swiping across his nipples, causing him to grind up his hips into your own. You pull away from him once again, leaving him gasping slightly. You grab the bottle of love from next to him, quickly popping open the cap and pouring the contents onto your fingers. You rub them together, trying to warm up the cold gel. You look up at him, finding him staring intently at your hand. “Am I moving too fast?”
“No. No no.” He shakes his head and chuckles, “just a little nervous.”
“Just tell me if you want me to stop, okay?” You place your hand down between where your hips met his, pressing your finger gently against his hole. He shivers against your touch, his hole flexing against your fingertip.
“Okay. I’m ready.” He finally lays down fully, not before pulling a pillow underneath his head. He lays his arms above him, looking up at you intently. You start to press your middle finger into him, watching as his face contorts at the new sudden feeling. “S-shit.” He chuckles nervously, “that feels so weird.”
“Don’t worry, you’ll get used to it.” You hum. You wiggle the digit in him for a second, curling it up, pressing it against his weirdly cold walls. After you feel like he’s gotten use to it, you press a second in to join the first, it pushed a high whine from him, closing his eyes and tilting his head back. You slowly thrust the two fingers inside him, curling them up gently. “Does it feel good?” You ask curiously.
“K-kinda? Yeah. J-just gimme a second to adjust.” You nodded and continue to just slowly thrust your fingers into him. You study his facial expressions, his face contorting slightly at the sensation, his mouth hanging open just a bit as he regulated his breathing. With every press his eyes would scrunch together and soon it began to draw soft moans, barely audible. “O-okay… keep going.”
“Just one more finger.” You place a gentle kiss to his face, “then you’ll be stretched enough to take me.”
You pause the thrusting of your fingers for just a second, giving him a second before slowly inserting a third. Skips bites his lip, a muffled pained moan erupting from him. He pulls away slightly, but eventually steadies himself again. Once it’s fully inserted you give him a moment. Eventually and painstakingly slowly started to wiggle them, stretching him. You grab the lube, pouring alittle bit more into his entrance making him gasp at the coldness. His messy hair clung to his face in sweat and his muscles relaxed around your fingers, allowing them to move freely, stretching him out.
“F-fuck, penumbra…” he murmurs. You pump your fingers in and out of him, watching melt into your grasp as he allows the pain to melt away and the pleasure to take over. His entrance flutters around you as you curl your fingers up into him. “F-feels good…”
“You think you’re ready?” You hum, kissing him on the cheek. He gives it a moment before nodding. You pull your fingers out, wiping them on the already dirtied sheets. A string of pearlescent cum dripped down from his weeping cock. You dislodge yourself from between his legs, allowing them to fall over the edge of the bed as you readjust the harness around your waist. “Get comfortable while I prep baby.” You hum.
He shifts himself in the bed, turning himself so that he lay against the pile of pillows against the headboard. He arranged them the same way always arranged them for you. You grab the dildo from where it lay abandoned, fumbling as you struggle to slip it into the ring of the harness. But, you finally get it in admiring the new appendage hanging from you. You’ve had it used on you plenty of times but you had to admit… it looks so good on you as well. You look over at where Skips has himself adjusted. “We doing missionary?” He asks and you nod in the affirmative. His eye glance down the toy that hung between your legs. You smirk and hold it up for him to admire.
“Looks good on me huh?” You giggle.
“Looks hot…” he mumbled, a blush lighting up his face. You climb up onto the bed, kneeling between his legs as you awkwardly maneuvered his legs around you. You hold onto his thighs tightly with one hand as you lube up the toy, jerking it off slowly in your hand. You grab it by the base, lining up the tip to his entrance, pressing the head. Skips takes a shuttery breath as he feels the cold silicone against him.
“I’m gonna go slow, okay?” You reassure him, “are you ready?”
He nods, looking up at you eagerly. You bite your lip and grab onto his hips as slowly you begin to press the tip of the toy into him. Skips throws his head back, a pained yelp pushing out of him, making you pause to give him a second. His eyes shut tight, mouth hanging open as he pants heavily. “D-don’t stop.” He finally gets out, “j-just keep going, I’ll get use to it.”
“Are you sure? You’re in pain.”
“Y-yes. I-I…” he swallows, his head tilting to the side as he looks at you through his messed up hair, tears pricking his eyes. “It feels kinda good. The stretch.”
You nod, still giving him a moment before continuing to push the toy into him. It struggled to push deeper, Skips flexing tightly around the toy making you stop again. You lean down and place soft kisses on his pale skin, reaching up to push away the loose strands of hair that obscured his face. “Relax, darling.” You mumble against his skin. After a moment of silence and gentle kisses, you can feel Skips body stop tensing up, relaxing under your touch. “Good boy.”
With a small, slow push, Skips finally bottomed out on the toy. He moaned, covering his mouth with the back of his hand as you gave him a minute to adjust. You pressed soft kisses against his neck and chest, hands caressing his bare chest. Finally, you give a small thrust, testing the waters. It punches a soft moan out of Skips and you wait another moment. He doesn’t look at you, his eyes squeezing tight. You see tears begin to fall, making you hesitate.
“Do you want me to pull out?” He shakes his head and takes a deep breath. You feel bad having to check in on him every few minutes, but you just want him to enjoy this as much as possible.
“I’m okay, penumbra. Please, keep going.” He mumbles against his hand. You nod and pull out just an inch or two before pushing back in. You start to set a steady pace of shallow thrusts, watching his face closely. Tears continued to pour from his eyes but his face contorted, his furrowed eyebrows slowly releasing and his mouth opening slightly, letting out soft noises. He looked at you through half lidded eyes, blushing deeper as he saw how closely you were watching him.
“You look beautiful.” You say gently, making him smile. He’s cut off by a moan as you start to increase your speed. “You’re doing so good, baby.”
“F-fuck.” He whines. You lean up and grip his hips tightly, watching as the toy disappeared into him repeatedly, watching how well he’s taking you. His hole greedily shuddered around the silicone, cock bouncing against his stomach, a drool of precum glistening the skin underneath his head. “F-faster…”
You hold his hips tight, pulling him closer with each thrust. Every slap of skin against skin pushed a louder and louder moan out of Skips, his arms flying up and grasping at the pillows above him. His legs held on to you tightly, shuddering. The bed began to rock at the strength of your thrusts as they got deeper, nearly pulling all the way out before slamming back into him. His eyes back into his head, his back arching as he began to let out loud, screaming moans. “Right there! Oh fuck right there!” Bingo.
You leaned back over him, one hand still holding onto this hips while the other gathered his hands, pinning them above him. You were nearly bending him in half, his legs locking behind you. He babbled his coherent noises and moans. Loud “yeses” and “harder!”s. Thank god you lived alone. The headboard slammed against the wall repeated, bed springs squeaking almost as loudly as Skips.
“Y/N… Y/N!” He moaned, looking up at you. “I-I’m gonna- f-fuck! I’m gonna-“
Thick ropes of cum shot out of his neglected cock, landing on his bare chest. His whole body shook as he suddenly when silent, his head fully thrown back and back arching. His ass fluttered around the dildo as you rode him through his orgasm. Finally, as his orgasm began to come to an end, he let out a loud gasping moan. You finally slow down and stop, letting him gasp for air, releasing his hands from your grasp. You lower his hips back down onto the bed, sliding out of him. You look over his face, recognizing the “fucked out” expression on his face as he becomes unresponsive. You kiss his cheek, trying to get his mind from the clouds. “It’s okay.” You reassure him. “It’s okay I’m right here.”
After a moment he finally looks at you, smiling widely. “H-holy shit.” He panted, “holllyyy shit.”
You laugh at his reaction, holding his face in your hands. “Yeah?”
“That was so…” he takes a deep breath, “holy shit.”
“We doing this again, sometime?” You tease, kissing him briefly and he nods frantically.
“Oh fuck yes.”