That Smile
Negan x TransMale!Reader (GN pronouns)
Synopsis: Negan offers some very Negan-esque support when he discovers that the Reader has had to deal with some transphobic issues at the Sanctuary.
CW: transphobia, no slurs used, Negan being very Negan, Negan being suggestive (as per usual), no pronouns used for the Reader though it is specified that they are trans male.
Requests are: OPEN
“Oh, fuck,” Negan says, looking almost like he’s about to panic. Which is decidedly not a common occurrence for him. “Shit, handsome- I didn’t mean it. I was just breaking your balls a little bit.”
You might have made a mistake here. Of all the people you could have screamed at- the leader of the Sanctuary was probably not the smartest choice. Oh, but you just couldn’t help it.
Not everyone stared, and not everyone was rude. There was pockets of kindness here and there- people who understood who you were and respected you for who you were.
As always, though, there were people who did not understand. People who looked at you weird or avoided you in the market. Negan had set out rules for basic respect, but that didn’t stop the occasional hate-speech or threat. It was the end of the world, after all, not Utopia.
“You have no idea what this is like, Negan,” you say with a sneer. He sets his jaw but doesn’t reply, letting you vent. “Every day someone makes a comment just loud enough that I can hear, or someone shoves into my shoulder. Or, hell, just the other day- someone called me something that was… absolutely vile.”
You point an accusatory finger at the man, whose gaze is getting darker with anger by the second.
“And you!” You start to raise your voice, and Negan’s lips twitch as if he’s trying not to grin. “You let it happen. And I am so sick of everyone’s fucking shit!”
Negan rubs a gloved hand over his chin, chuckling darkly as he does so.
“You done, gorgeous?” He asks, or tells, really. There’s no room for argument with the way he unclenches his jaw. “Because I have something to say, and you? You are gonna listen.”
Negan places Lucille carefully leaned against the table before rounding it to stand before you. You swallow thickly, not sure where this is going, but not sure you like it either.
“I need you,” he says slowly while raising a finger to brush your temple softly. “To cast your big ‘ol brain back a few days and really think about what I’m about to ask you.”
You stumble over a few attempts at speech before he shushes you softly.
“The fuckhead that broke the rules? Called you something he really shouldn’t have…” His eyes flit between yours, lips spreading out into a grin that would send molten heat through a celibacy-practicing nun. “...when did you see him last?”
You let out a little ‘uh’ sound, trying to order your brain to stop tumbling around and work out the answer. It had been three days since the slur, and… now that you were really thinking about it. You hadn’t seen him since. Usually he was always lurking around to get another shot in.
The realisation must have shown on your face, because Negan let out a throaty chuckle.
“See? Now you’re gettin’ it,” he says, leaning back against the table and crossing his arms. “Now, I know you wouldn’t want me killing anyone, so, don’t worry. He’s not dead.” You bit back the sarcastic comment that threatened to spill out.
Negan runs his tongue over his bottom lip as if savouring something very sweet. Your eyes track the movement, and you know he knows it.
“But that doesn’t mean he’s having a good time, either.”
“What did you, uh, do to him?” You ask, voice breathy with desire. No one had defended you quite like this before. And if you didn’t know any better, you’d think Negan was flirting with you just to make a point.
But it had been like this for months. Negan putting on all the charm when you were around, and doing his damndest to get you to open up to him. He didn’t care that you were trans, he liked you for you.
You liked him too, of course. How could you not? Big strapping man with big dick energy, a leather jacket and a phallic bat? What wasn’t to love?
“Oh, you know,” he chuckled. “Threw him the hole for a few days. Shit, I think he’s still in there.”
You stifled a smile, knowing that the asshole was now suffering for his crimes. Well, shit- turns out Negan did give a shit about your rights. It was almost like he was an active protestor for Trans Rights. The thought made you laugh.
“I’ll have to make a trip down there to see if he’s learned his lesson yet.”
This time you can’t bite back the smile, and he draws out an appreciative noise.
“Oh, there he is,” he brushes your chin with his thumb. “There’s that handsome smile. Fuck, you really turn me on, you know that?”
Your grin splits wider and blood rises to your cheeks.
“I’m serious!” He defends himself. “My dick is so hard right now- I could cut diamonds.”
You role your eyes at his theatrics, but he knows that you enjoy his crude comments. He knows you want him. His gaze softens for a moment, and the sincerity you see there almost makes you melt.
“No more hiding things from me,” he says. “Something happens- someone breaks the rules? You come find me.” Negan lets out a huff of a sigh, caressing your jaw now.
“Can’t have my handsome man upset, can we? I just live for that smile.”
You don’t even notice the grin spreading across your lips this time.
“Yeah, that’s the one…”
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Cherry 🍒
S7 Negan x Virgin Female Reader
Summary: You sneak into Negan’s bed in the middle of the night and seduce him into ‘popping your cherry.’
Warnings: 18+, smut, age-gap (reader is 18, Negan is mid 40's), unprotected sex, Negan taking your virginity & being sweet with you, mentions of family death, bleeding during sex, oral (both receiving), sitting on Negan’s face, breeding
Note: this is pure filth. If you’re uncomfortable with extreme age-gaps, please don’t read.
You shivered as your bare feet quietly shuffled down the cold hallway, stopping right outside the leader's bedroom door. The sounds of Negan's light snoring filtered through the cracks as you softly pushed the door open, pleased to find it unlocked. You tiptoed your way over to the empty side of his bed before sliding underneath his soft white sheets and inhaling the unique scent of him - leather and fresh linen.
You've always felt comfortable with him. Negan welcomed you to the sanctuary with open arms about a year ago when you were seventeen, after your father passed away. His men found you walking along the road one day and brought you back to Negan, who immediately took you under his wing and made you feel safe for the first time since your father died.
You're not like his wives. More like the daughter he never had and he's made that boundary crystal clear on more than one occasion. You've made several subtle advances towards Negan in the past.. All of which he has politely rejected by changing the subject or blatantly ignoring you.
Still, this doesn't stop you from quietly moaning his name when you touch yourself at night.
"Negan.." You whispered cautiously as you snuggled into the sheets. This wasn't the first time you crawled into his bed at night, feeding him lies about nightmares you never even had. However, this time.. you were determined to get what you wanted.
During your recent previous attempts, you'd remain on your side of the bed and Negan wouldn't even know you were there usually until the next morning - lecturing you when you woke up about how sneaking into his bed is inappropriate. You hated when he used that word. Like a strict school teacher.
A few moments of silence passed until you boldly shuffled closer to him, wrapping your hand around his arm and snuggling your face into his bicep. You breathed in the intoxicating aroma of his soft skin as your legs delicately pressed into his underneath the blanket.
"The hell are you doin' y/n?" He asked, his sleepy voice deeper and raspier than usual and it made your heart flutter.
"Can't sleep."
"I think we both know you're lyin', doll. You know you can't stay in here. We've had this discussion. It's ina-"
"Yeah yeah I know. Inappropriate, geez." You interrupted him, rolling your eyes in the dark.
"Exactly, so why are you in my bed?"
"My.. dreams. They keep waking me up."
"Nightmares again?" He asked, using a softer tone this time.
"No.. no nightmares this time. Just.. dreams."
Negan shifted uncomfortably next to you, scooting up a little in the bed and wrapping his arm around you in the process. "What kinda dreams, doll?"
You snuggled into the nook of his armpit, getting practically drunk off his manly smell as your hand carelessly glided over his shirtless, hairy torso until settling on his lower abdomen.
Without missing a beat, Negan placed his hand over yours, moving it higher on his torso. "Y/n.." He said like a warning, sternness dripping from his tone.
You ignored him, refocusing your attention back to his previous question. "I dunno.. they're just.. like.. sexual dreams, and then I wake up and I'm all frustrated because I don't know what I'm doing-"
"Stop." He sighed with frustration, running a hand down his face. "Fucking christ, y/n. You cannot say shit like that in front of me."
"Why not? It's not like you're my daddy or anything." You teased him, sliding your hand to his lower stomach once again. You almost whimpered when your fingertips brushed over the soft curls peaking out of the waistband of his boxers and your stomach fluttered when he didn't stop you this time.
He let out a long sigh, glancing down to your hand that teased the sensitive skin under his waistband. "Baby...fuck. We can't." He said almost painfully.
"Okay.. I get it." You said defeatedly, removing your hand and shifting to turn over before he stopped you, pulling you back in.
He sighed, like he was about to regret asking you this. "What happens.. in your dreams?"
With the moonlight beaming through the window, you managed to catch a glimpse of the lust that flickered in his gaze before his hazel eyes dropped to your lips.
"You treat me different.. like.. one of your wives."
"Yeah? And how's that, baby?" He asked curiously as his lips hovered next to yours.
"You.. kiss them." You stated hesitantly, hoping it was dark enough in the room that he couldn't see your cheeks burning red.
"Oh? Are you jealous, doll?"
"...a little." You admitted, making him chuckle.
He tilted your chin up, lightly gripping your jawline as his eyes dropped to your lips. He stared at them as if he was contemplating if he should give you what you want.
"One kiss, y/n." He said, closing the gap between you and pressing his soft lips to yours. You whimpered into his mouth, earning a slight smirk from him as he pushed his talented tongue past your lips. You couldn't believe you were finally tasting him and you savored every second of it.
He kissed you until your lips were sore, tangling his fingers through your hair and groaning every now and then, making your panties soaked.
You slid your leg over his until his muscular thigh was pressed right up against your aching center and you couldn't help but grind against it, desperate for some friction.
"Y/n." He warned, knowing what you were doing beneath the covers.
"Please, Negan."
His solid erection pressed into your stomach each time you moved your body against his and you imagined the way it would feel inside of you.
“Please what?” He said in between kisses, allowing you to use his thigh to get yourself off.
“Please let me come."
"I'm not touching you, y/n. But I can't stop you from coming."
And that was all the permission you needed to grind against him harder and bring yourself to an orgasm just from humping his thigh.
You buried your face against his neck and rode out your high, whining and whimpering as you soaked through your panties. "Oh my god, oh my god, Negannnn."
"Satisfied now, doll?" He chuckled.
"No.. I need this." You said, pressing your palm against the hard bulge in his boxers. "Please."
"You don't know what you're asking for, sweetheart."
"I do, Negan. I know exactly what I want.. And I've wanted you for so long." You kissed his neck as you rubbed his cock through the material. "I see the way you look at me. I know you want me too."
He sighed, accepting that you were right. "Maybe. But we can't always get what we want, doll."
You grinned, taking that as a challenge as you slid lower beneath the blanket, kissing his chest. "Why not?"
"Baby.."
"If you tell me to stop, I'll stop." You said, wanting to earn his consent before climbing over his legs and settling in between them. He sighed again, turning all the way over on his back to allow you better access.
You licked a line from the bottom of the trail of hair that led up to his belly button, earning a moan from him as he slightly lifted his hips in response. "Baby, you don't have to-"
"You said you wouldn't touch me, but you didn't say I couldn't touch you." You explained, pulling his boxers down slowly. You watched closely as his cock sprung free, and your mouth practically watered at the sight of it. You wondered how you'd fit it in your mouth, much less your pussy.
"It's so.. big.." You said, wrapping your hand around it. Your mouth fell slightly open at the velvety feeling of it as you stroked it up and down in your palm.
Negan was propped up on his elbows as he watched you through heavy, lust-filled eyelids. For once, he was speechless, waiting for your next move.
You lowered your head, taking the tip of him into your mouth and wrapping your lips around it softly. You sucked on just the tip as you looked up at him through your brows and watched his head fall back while the prominent vein in his neck bulged against his skin. Lowering yourself deeper, he let out a long groan when he felt himself in the back of your throat.
"Fuuuuuck, baby. Feels so fuckin' good."
You bobbed your head up and down on him until your jaw ached, wanting to make him proud. Finally, he pulled your head off of his length, and you watched as the precum leaked from his red, swollen tip. His breaths were heavy as he looked down at you. "Fuck, that's enough. You're gonna make me come, sweetheart.
"I want to taste you, Negan.. please?" You begged, looking up at him innocently.
"Yeah? You want me to come in your mouth?"
You nodded as wrapped your lips around his thick length again, tasting the bead of salty precum. You moaned at the new taste, sucking firmly over and over until you felt more of his warm liquid spurt out, coating the back of your throat. You moaned around him again, not taking your mouth off of his cock until you swallowed every drop.
Sweat ran down the side of his face and his chest rose and fell heavily as he watched you. "Goddamn. What happened to my sweet, innocent girl, huh? When did you learn to suck cock like that?"
"Just now. That was my first time." You shrugged, shuffling up his body until your legs straddled his waist and you pulled your shirt over your head, tossing it on the floor and exposing your perky, bare breasts to him.
You pinched your own nipples teasingly as you bit you lip and stared down at him.
"Fuck, you are so beautiful.” He said, watching you play with your nipples.
"You don't wanna touch?" You pouted, sticking out your bottom lip.
"Of course I wanna fuckin' touch you, y/n. You have no idea. I wanna touch every inch of you." He sighed, leaning up on his elbows again until his face was inches away from your chest. "But, I can't."
"Then don't use your hands.. lick me instead." You insisted.
He looked up at you through his brows before his gaze returned to your breasts. You leaned forward, brushing your nipple against his beard until it hardened even more. When it brushed his lips, he instantly took it into his mouth and groaned, sucking it gently. After a few moments, he switched to the other one, flicking his tongue against it. Your head fell back while your fingers intertwined in his slick, black hair.
"Negannn." You breathed out, and he finally pulled away.
"Take those panties off and sit on my fucking face. Now." He demanded, laying flat on his back.
You eagerly obeyed him, quickly removing your panties and climbing over his face before lowering yourself down slowly. You hovered over him lightly, not wanting to press all the way down until his hands roughly pulled you closer.
"I said, sit." He said before burying his face in your cunt. The tip of his nose pressed against your clit as his tongue devoured your dripping hole and he moaned with approval.
You lifted slightly, being too sensitive too his touch, but he leaned forward, taking your clit between his lips and sucking. You cried out as your orgasm instantly rushed through you and you soaked his face. You came hard and fast, but he didn't mind as he moaned loudly, lapping up your juices. You tried to climb off of him, but he held you in place, still licking you like his life depended on it.
"Negan.." You blushed.
"Hm?"
"That's enough." You giggled.
"I'll never get enough of this sweet pussy, doll. You wanted me, now you've fuckin' got me."
His words made the butterflies somersault in your chest. You hoped he meant it. You hoped he loved you the way you loved him.
"Lay down for me." He said, finally letting you climb off of him.
You did as he said, getting comfortable on your back as he crawled over you and settled between your legs. Looking down, you noticed he was rock hard again and he rubbed the tip of his cock teasingly in between your wet folds.
"Negan.. I need to tell you something."
"Hm? What is it, doll?" He asked, leaning over you and holding himself up with his palms on either side of your head on the mattress.
"I-I've never done this before."
He smirked, looking into your eyes. "I know."
"What do you mean you know?"
"I hear everything in this place, y/n. I've heard you talking about me to your friends." He pressed his lips to yours before looking at you again. "I've heard you moaning my name at night in your bed while you touch that pretty pussy. I know everything about you, doll. I pay attention, even when you think I'm not."
You blushed at his words as you stared up at him speechless, making his smile widen. "So adorable when you're embarrassed."
He kissed you again, so hard that it took your breath away and in that moment, you knew you were head over heels in love with this man. You just wondered if he felt the same.
“What else happens in your dreams, baby? Do you let me fuck this little pussy?” He whispered in your ear, causing a chill to run down your spine.
“Y-yes.” You managed to choke out, making him chuckle.
He leaned back up, placing one of your legs over his shoulder as the other fell open for him.
“You ready for me to break you in, sweetheart? Pop that sweet little cherry?”
"Fuck, yes. Please." You whined, scooting closer to him until the tip of his cock brushed against your sex.
Negan chuckled lowly, pressing the head of his cock right against your hole. He watched you intensely as he pushed just the tip in, stopping before he went any further.
“You good, baby?” He asked, making sure you were good to continue. Once you nodded, he slid slightly deeper, feeling resistance before pushing through with a force.
You cried out at the sudden ripping sensation, making him stop again.
“No.. keep going.” You urged him, already aching from how he was stretching you, but you needed him to fill you completely. So he did, pushing himself all the way in with one swift thrust.
Your mouth fell open silently as he pressed against your cervix and let out a growl.
He fell over you again, kissing your lips as he thrusted into you at a steady pace. “You did it, baby.” He praised you softly. “I am so fuckin proud of you.”
He moved slowly, making you deliberately feel every inch of him. He repeated this motion until your face was on fire and your lower abdomen tingled.
"Fuck, y/n. You are so fucking tight." He said through gritted teeth, looking down between the two of you as he leaned back up on his knees.
"Oh fuuck, look. at. that, doll."
You leaned up on your elbows, looking down and widening your eyes when Negan pulled out of you, revealing his blood covered cock.
His thumb reached down to swipe a trail of your blood off his dick before bringing it to this mouth. You watched him enamored as his eyes rolled to the back of his head at the taste of you and he moaned with satisfaction. You blushed hard at the sight of Negan tasting your blood.
“Who do you belong to?”
“Negan.” You answered without question, following it with a moan as he pushed back into you without warning.
“That’s right, doll. This pussy? Is mine now. Understood?”
“Y-yes sir.” You cried, as he pumped into you faster.
"Ow. Ow, fuck. It hurts."
“I know baby. I know. You want me to stop?”
“No.” You said quickly. “Please don’t stop. I want it harder.”
He smiled down at you proudly as his hips bucked into you harder and your eyes clenched shut as your fingers gripped the sheets.
Looking down between the two of you again, he groaned at the sight of your blood completely coating his cock and leaking out of you with each thrust.
You whined and whimpered, desperately wanting to come again. He grinned knowingly, pressing his thumb to your clit and making your body shutter. "You gonna come on my cock, sweetheart?"
You nodded as tears flooded your eyes and his finger started working over your clit more intensely.
"Yes, yes. Please make me come."
He fucked you fast and rubbed your clit in perfect circles, watching you come undone around him. Once your walls were done convulsing around him, he fell over you again, kissing your neck and groaning in your ear. "That's it. That's my good girl."
Wet noises filled the air as he fucked you unforgivably hard. "You gonna let me cum in this pussy, baby?" He asked, biting your earlobe.
You couldn't speak, so you nodded as your vision went cloudy and his thrusts became more erratic until he stopped suddenly, pushing himself balls deep inside of you as his dick pumped you full of cum and he growled in your ear.
"Fuck, fuck, fuuuck, baby." His thrusts started again, soft and light this time as he pushed his seed deeper inside of you. He kissed your jawline, then your lips, before pulling back slightly to look into your eyes.
"Y/n... I love you. I love you so much, sweetheart. And goddamn I love this pussy."
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