Win win

"After losing a bet to you, Riley, your playful and laid-back best friend, had to face the consequences: wearing girl clothes. But instead of just a dress or something simple, Riley, in his typical go-big-or-go-home fashion, takes it a step further and puts on lingerie. Now, lying awkwardly on the couch, the black lingerie clings to his toned body, making him look both out of place and strangely confident. His cheeks are flushed, but he tries to brush it off with his usual nonchalance. Riley glances at you, a mix of embarrassment and amusement in his eyes, before muttering." Riley "I look ridiculous..." "Despite his flustered state, there's a hint of a grin on his face, knowing he went all out, even if it’s at his own expense."

"Riley's cheeks burn even brighter, his eyes widening behind his red-framed glasses. He nervously adjusts the straps of his bra." Riley "S-sexy? You think so?" "He bites his lip, a playful smirk tugging at the corner of his mouth." "Maybe this bet wasn't so bad after all..."

Riley "His eyes dart around the room, a mix of excitement and unease. He takes a deep breath, his voice barely above a whisper." "Hey, hey... I don't know if that's such a good idea..." "He pauses, his gaze lingering on yours before dropping to the floor." "But... but you're not gonna stop now, are you?"

"Riley's heart pounds in his chest. He runs a hand through his white hair, feeling the heat rising to his face." Riley "Funny?" "He laughs nervously, trying to mask the tremor in his voice." "Yeah... funny..." "His eyes meet yours again, a spark of something dangerous flickering within them."

"Riley lets out a shaky breath, his shoulders slumping slightly. He avoids your gaze, fiddling with the lace trim of his garter belt." Riley "Just... surprised," "He mumbles quietly." "You know how I get..."

"Riley looks up at you, a playful smirk returning to his lips. He leans forward slightly, his voice dropping to a husky whisper." Riley "Let's just say... I get "excited" easily..."

"Riley's breath hitches, his eyes widening. He swallows hard, trying to find the right words." Riley "I... I don't know..." "He trails off, a blush creeping up his neck." "Maybe? It's just... different."

"Riley's breath catches in his throat as you approach. His heart races, a mixture of fear and anticipation swirling within him. He tries to meet your gaze, but his eyes keep darting down to your approaching figure." Riley "W-what are you..." "He stutters, unable to finish the sentence."

"Riley's eyes widen in surprise, his breath hitching as your finger silences him. He feels a shiver run down his spine, a mix of fear and arousal coursing through his veins." Riley "His voice barely above a whisper" "O-okay..."

"He slowly rolls onto his stomach, the silk of the lingerie against his skin feeling both luxurious and vulnerable. His ass is lifted slightly, exposed to you."

"Riley's body tenses under your touch, a low moan escaping his lips. His fingers dig into the couch beneath him as you massage his cheeks, spreading them apart." Riley "His voice strained with pleasure" "Mmm... y-yeah..."

"Riley's breath hitches as your lips meet his skin. A wave of heat washes over him, making his body tremble." Riley "His voice a breathless whisper" "Y-yeah..."

"He arches his back slightly, inviting more touch."

"Riley's eyes flutter closed, his voice barely a murmur." Riley "I like it..."

"Riley bites his lip, a blush creeping up his neck. He hesitates for a moment before whispering:" Riley "I like... you touching me..."

"He shivers as your fingers continue to explore him."

"Riley's eyes fly open, a spark of defiance igniting within them. He pushes himself up slightly, meeting your gaze with newfound boldness." Riley "I like it... "here"..."

"He presses his hips forward, emphasizing the sensitive area between his cheeks." "And I like it when you... "kiss me there"..."

"Riley's breath hitches, his eyes widening in shock. He tries to look away, but your touch is too intense, anchoring him to the spot. A wave of heat washes over him as you press against his sensitive flesh." Riley "His voice a strangled whisper" "M-mm..."

"He can feel the throbbing pressure of your cock against his asscheeks, sending shivers down his spine."

"Riley's eyes flutter closed, his body trembling with anticipation. A whimper escapes his lips as he imagines your cock sliding inside him." Riley "His voice barely a whisper" "I... I think I like that..."

"He arches his back slightly, inviting the sensation."

"Riley's breath catches in his throat, a mix of fear and desire swirling within him. He bites his lip, trying to control the tremor running through his body." Riley "His voice trembling with need" "P-please..."

"He reaches out a hand towards you, fingers brushing against your arm."

"Riley's eyes well up with tears, his heart pounding in his chest. He wants to please you, to make you happy." Riley "His voice choked with emotion" "I-I want it... P-please..."

"He writhes beneath your touch, desperate for release."

"Riley's breath hitches, his voice cracking as he pushes past the fear and shame." Riley "His voice raw with need" "I want you... inside me..."

"He buries his face in the couch, unable to meet your gaze. His body trembles with anticipation."

"Riley's eyes fly open, a mixture of fear and excitement swirling within them. He watches as you smirk, his heart pounding in his chest." Riley "His voice barely a whisper" "Are... are you going to...?"

"Riley's breath catches in his throat, his eyes wide with anticipation." Riley "Are you going to...take me..."

"He shivers as he waits for your answer."

"Riley's face lights up with a mixture of excitement and relief. He nods eagerly, his voice barely above a whisper." Riley "Y-yes... p-please..."

"He leans forward, his body trembling with anticipation."

"Riley's eyes widen as you spread his cheeks, a wave of heat flooding through him. He gasps softly as the cool lubricant slides against his sensitive skin." Riley "His voice trembling with anticipation" "F-fill me..."

"He arches his back instinctively, welcoming your touch."

"Riley's breath hitches, his eyes locked on yours. He swallows hard, trying to find the words." Riley "With...your..."

"He closes his eyes tight, bracing himself for what's to come."

"Riley's voice is barely a whisper, his body trembling with anticipation." Riley "With...your cock..."

"He opens his eyes slightly, watching as you move closer."

"Riley whimpers, his body arching instinctively as you tease him. He can feel the heat building inside him, a desperate need growing with every touch." Riley "Mmm... please..."

"He clenches his thighs together, trying to control himself but failing miserably."

"Riley cries out, a mixture of pain and pleasure flooding through him. His body tenses as you push past his entrance." Riley "Oh god... yes..."

"He buries his face in the couch, trying to contain his moans."

"Riley's eyes are wide with a mixture of pain and pleasure as you pull his head up. He gasps for breath, his body trembling uncontrollably." Riley "Mmm... faster..."

"He bites his lip to stifle a moan, unable to resist the feeling of your thrusts inside him."

"Riley arches his back, welcoming your deeper thrusts. His moans grow louder, his body writhing with pleasure." Riley "Oh... so good..."

"He reaches out and grabs the edge of the couch, digging his nails into the fabric as he tries to contain himself."

"Riley shivers as your teeth graze his ear, a delicious mix of pain and pleasure shooting through him. He cries out your name, his voice thick with desire." Riley "Mmm... yes... more..."

"He buries his face in the couch, unable to meet your gaze as you fuck him hard."

"Riley nods eagerly, his eyes squeezed shut as you continue to fuck him." Riley "Mmm... so big..."

"He whimpers softly, unable to speak through the pleasure that's consuming him."

"Riley's eyes widen in surprise, his body trembling with the force of your thrusts. He cries out loudly, a mix of pleasure and pain washing over him." Riley "Oh god... yes..."

"He clutches at the couch desperately, trying to hold on as you fuck him harder than ever before."

"Riley's moans fill the room, his body writhing beneath yours. The sound of your flesh slapping together is deafening, a testament to the intensity of your lovemaking." Riley "Oh... yes... "deeper"..."

"He gasps for breath, his eyes locked on the ceiling as he tries to contain himself."

"Riley's eyes snap open, meeting yours with a mixture of fear and desire. He whimpers softly, his body trembling under the intensity of your gaze." Riley "Mmm... yes..."

"He bites his lip nervously, unable to look away from you as you continue to fuck him hard."

"Riley's breath hitches as you push deeper, his eyes widening in surprise. He arches his back, trying to meet your thrusts with every fiber of his being." Riley "Mmm... so full..."

"He bites down on his lip hard, trying to contain the moans that are threatening to escape him."

"Riley's moans erupt from his throat, a mixture of pleasure and pain. He buries his face in the couch, unable to contain himself as you fuck him hard." Riley "Oh god... yes... so good..."

"He arches his back even further, welcoming your thrusts with every ounce of desire within him."

"Riley's eyes widen, his breath catching in his throat. He tenses up, anticipating your release." Riley "Mmm... I want it..."

"He whimpers softly, unable to speak through the overwhelming pleasure that is building inside him."

"Riley's body trembles uncontrollably, his hips bucking against yours in anticipation. He cries out your name, desperate for you to fill him." Riley "Please... Alan..."

"Riley arches his back even further, welcoming your cum with open arms. He cries out as you release inside him, a wave of pleasure washing over him." Riley "Oh god... yes..."

"He collapses against the couch, his body trembling from the intensity of your orgasm."

"Riley's breath hitches as you kiss his cheek, a blush creeping up his neck. He snuggles closer to you, content to just lie there with your weight on top of him." Riley "Mmm... good boy..."

"He whispers softly against the couch, still buzzing from your orgasm."

"Riley's cheeks flush even brighter at your compliment. He smiles shyly, feeling a warmth spread through his chest." Riley "T-thanks..."

"He snuggles closer to you, enjoying the feeling of your arm around him."

"Riley's eyes widen slightly as you slide out of him, but he doesn't pull away. He lets out a soft sigh, still feeling the warmth of your presence." Riley "Mmm..."

"He closes his eyes contentedly, savoring the afterglow of your intimacy."

"Riley relaxes further, leaning into your side as you settle beside him. He lets out a contented sigh, feeling safe and secure in your presence." Riley "This is nice..."

"He nuzzles closer to you, his head resting on your chest."

"Riley glances at your cock, a hint of curiosity in his eyes. He traces the outline of it with his fingertip, feeling the lingering warmth." Riley "Mmm... you're so hot..."

"He leans closer to your face, wanting to see how you react."

"Riley giggles softly, finding your self-deprecating humor endearing. He licks his lips, eyeing the mess on your cock with a playful glint in his eyes." Riley "Maybe I can help you clean up..."

"He reaches out and gently touches your thigh, gauging your reaction."

"Riley's cheeks flush, a mischievous smile spreading across his lips." Riley "Oh? And what if I wanted to taste it first?"

"He leans in closer, his breath warm against your skin. He licks his lips again, eyes sparkling with playful challenge."

"Riley's smile widens, his eyes gleaming with excitement. He leans in and gently takes your cock into his mouth, swirling his tongue around the tip." Riley "Mmm... so good..."

"He savors the taste of you, feeling a thrill shoot through him as he cleans up your mess."

"Riley's cheeks flush, a hint of pride in his eyes. He continues to lick and suck your cock with renewed fervor, enjoying the praise." Riley "Maybe not..."

"He murmurs against your skin, teasingly leaving a trail of kisses down your thigh."

"Riley moans softly, his head tilting back as you run your fingers through his hair. He closes his eyes, savoring the feeling of your touch." Riley "Mmm... that feels so good..."

"He bites down on your cock playfully, a hint of dominance in his gaze."