Work Text:
You swear your intentions were pure at first; it was just you trying to shoot the shit with Daryl and a cowboy hat, but you hadn't expected him to look so… natural with it on.
Walking around the shopping mall you, Glenn, Daryl, and Maggie were scouring through, you had come across a plain black cowboy hat lying on the floor alone. It appeared to be relatively spotless besides a little dirt and dust on it. You bent over and picked it up, your hand patting away the grime as you examined it. You couldn't help the shit eating grin that split on your face, your eyes flaring mischievously as you made your way back to your poor unsuspecting boyfriend who was searching through the camping department.
Sneaking up behind him, you quickly placed the hat on his head, eliciting a surprised grunt from the man in front of you.
"There," You said with your hands placed on your hips. "Now you're a real cowboy." He turned around to look at you with a glare. "Ain' no cowboy." He grumbled, and your breath caught at the sight of him. Every witty comeback you had been curating in your mind had suddenly died in your throat along with your ability to speak. "Wha'?" Daryl asked at your sudden silence. You swallowed nervously, "You look great, real sexy."
“Shuddup.” He scoffed, taking the hat off and placing it on your head so that it slightly obstructed your vision. He continued further into the department. “I’m serious!” You called out with a laugh as you chased after him.
“Wild west movies used to really get me going, you know!”
He didn’t see you shove the thing into your bag, or the fact that you were biting back a smirk the whole ride back to the prison.
You hadn’t forgotten about the way he looked in it, nor the fact that every time you passed by your bag, the hat felt like it was going to burn a hole right through the floor. You were waiting for the perfect opportunity to bring up its potential use in the bedroom until one fell into your lap - more like his.
You were sitting on his lap as he had his back pressed against the prison wall, his lower half resting on the two mattresses the both of you had pushed together to make a makeshift double bed. His fingers dug into the skin of your hips, your hands tightly clasping his cheeks, holding his lips onto yours as you made out fervently. Your body was slightly raised above his when you remembered the cowboy hat. You pushed a finger in between your mouths as you separated with a smirk.
“Wait.” You breathed. “You okay?” He asked in concern, searching your face and eyes for any sight of discomfort. “I got something I wanna try, if that’s fine with you.” You nodded gently. “Wha’ is it?” Your smirk formed into a wide smile at his question.
He watched you with a mix of curiosity and anticipation as you leaned over and unzipped your backpack, his palms that rested on your hips continued to keep a firm grip on you as reached for what you were looking for. His eyes nearly bulged out of their sockets when they caught sight of the brim of that stupid cowboy hat.
“The hell?” He couldn’t help but say. It wasn’t full of disgust, but rather surprise. You laughed, “I may or may not have brought it back home with the intention of asking you to wear it while we have sex.” The sides of his lips quirk as he takes the hat from your hands. “I guess ya really were serious about wild wes’ movies gettin’ ya goin’.” But nonetheless, he puts it on, and you bite your lip.
“Like I said, you’re the sexiest cowboy I’ve ever seen.”
He tilts his head up as your lips lock in an amorous embrace, and you grind your hips down on his hard-on. He groans against your lips, gripping and pressing your body down to receive maximum pressure from your cloth covered cunt. Your kisses trailed down his neck, nibbling on his scruff and unbuttoning his sleeveless shirt to push off of his shoulders, which he helped you do. Your greedy hands trailed through the patch of hair on his chest, following the hair down to where it disappeared into his jeans. You unbutton them, moving your butt down a little bit so that you could take him out of his underwear.
He hissed in pleasure as you pressed down on his leaky tip, rubbing his precum around before you bent forward, adjusting your body so that your ass was raised and arched, licking a stripe from the vein on the underside of his cock to the tip, twirling your tongue around it.
“Shit!” He let out a raspy whimper, burying his thick fingers gently gripping onto the roots of your hair. The pressure on your scalp was welcomed as you took him further down your throat, swallowing around him and fondling his balls with your free hand. Daryl desperately tried to keep himself quiet, seeing as though the walls of the prison weren’t thick, and anyone could hear him, and that was something that he didn’t think he would be able to live down.
He could feel himself nearing his climax with every suck of your devilish mouth, and he knew that you could feel him too. You peered up at him through your eyelashes, watching his shirtless chest rise and fall heavily, he looked dark as he practically gazed into your soul, the cowboy hat adding a shadow over his features that turned you on beyond comprehension. You pressed your thighs together to desperately relieve the growing tension between your legs, and when the fat of them put pressure against your clit, you whined, the noise shooting up your boyfriend’s spine.
“Fuck, sweetheart. ‘M gunna cum.” He warned, his back arching and hips chasing your warm mouth. You only pulled off to say, “Down my throat.” Your words were heavy and breathy, but you didn’t care, taking him back into your throat and stroking what you couldn’t swallow. He gulped, allowing his head to lean back on the concrete cell wall, biting on his bottom lip so hard in an attempt to stay silent that he could’ve sworn he tasted the metallic tang of blood.
“Yeah?” He asked with a breathless groan. “‘Wan’ me to paint that pretty little mouth of yours white?” You whined at his dirty words, and he felt your noises burn through his veins like fire. He didn’t hold back from occasionally bucking his hips, his thrusts growing sloppy before he pressed your head down, shooting his load deep down your esophagus.
You swallowed his cum, which caused him to hiss due to oversensitivity. You pulled off of him, licking your lips before sticking your tongue out to show him that you hadn’t wasted a drop.
“God damn, girl.” He grunted as you crawled your way up to his lips to place a deep kiss on his lips, allowing him to taste himself. “Are ya tryin’ta kill me?” He asked when you pulled away. You giggled, dragging playful fingers up and down his chest. “Maybe?” You said, biting your bottom lip with a smile.
He just scoffed, kissing you once more as you avoided knocking your head against the rim of his hat. “Let me ride you, cowboy.” You heaved.
He nodded, allowing you to stand and take your clothes off as he rid himself of his pants and underwear.
You clambered back on top of him, allowing your soaked slit to gently caress his hard cock.
“Fuck.” He cursed, the grip on your hips turning bruising due to your teasing. You mewled at the feeling of his heated skin brushing your sensitive clit, your self control slipping as you reached down and lined his cock up to your entrance, slowly sinking down due to the lack of foreplay and prep. The initial stretch of his tip hurt, your nails digging into the skin of his tanned shoulders, a silent cry leaving your lips as your head fell back.
Daryl gave you a moment to adjust to his size, distracting you with his calloused thumb, which rubbed comforting circles onto your tiny bundle of nerves. Your muscles loosened as you moved, slightly bouncing until you found a rhythm where your ass met his thighs. He aided you in your riding, guiding your body up and down.
“So fuckin’ wet.” He grunted, rolling both of his lips between his lips as he watched where your bodies joined together, as though he was in a trance. “‘S all for you, D.” You slurred. His cock repeatedly brushed against that sensitive spot inside of your body. He was already sensitive, which made him all the more determined to help you reach your peak first.
“Put yer hands on the wall.” He rasped. You placed your arms on either side of his head, your breasts pretty much shoved in his face when his hips rose up, fucking themselves into you harshly. You yelped in surprise, pressing your palms harder against the walls as he pounded into you from below. He raised his head, his eyes searching for yours from under the hat.
His irises swam with lust and need, but also a hidden determination that only he knew about.
“‘Gunna make you cum real good, pretty girl.” He huffed a ragged breath. “Promise.”
“Please, Dar. I need it!” You cried.
He looked away from you, focusing on his thrusts which were unforgiving, bruising your cervix with every slam of his tip. Your arms grew shaky as you neared your end, almost causing you to fall forward if you hadn’t laid your head on the cool rock.
“So close,” You breathed, “‘M so close, baby, please.” You begged. “I gotcha. ‘Gunna cum with ya, sweet cheeks.” Your body flushed with relief at his words.
Your bodies worked together to help reach your climaxes, and when you did, you held back a loud moan, and Daryl hid his in between the valley of your breasts, which lightly bit into. There might be a mark there tomorrow, but who cares?
You shuddered through your world shattering orgasm and he worked you through it, lazily thrusting into you until you muttered the words, ‘no more.’
You slowly sat back down, wincing seeing as though his softening cock was still shallowly buried inside of you.
“Holy fucking shit.” You laughed deliriously. “If I knew ya would’a been all pent up like this over some hat I would’a worn it sooner. Maybe even take ya righ’ then and there in tha’ mall.”
You smirk in amusement at his daring words, “Is that so?” You asked with a mischievous smile. “Mhm.” He hummed with a grin, his hands descending to gently massage your outer thighs whilst you cupped his cheeks, both of you falling into a blissful, giggly kiss.