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English
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Part 1 of Chariot's Kinktobers 🍆💦
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Published:
2025-10-01
Completed:
2025-10-31
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70,891
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31/31
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Kinktober MMXXV

Chapter 31: Gentle Things for Ruined Men ✨ Basil Stitt

Summary:

Prompt: Day 31: Wild Card.
Pairing: Basil Stitt x MTF!Reader.
Tags: Anal sex, creampie, dirty talk, dom/sub, established relationship, handjobs, mommy kink, nipple play, praise kink, prostitution, trans character, trans female character.

Notes:

(See the end of the chapter for notes.)

Chapter Text

You stand outside Basil's apartment, leaning slightly against the wall, hands slipped into the pockets of your coat. You don't mind the waiting. You've always been good at waiting, at letting things come in their own time.

Basil's place is on the third floor. The building is old, like so many others in this part of the city, but it has its charm; faded, like an old photograph, worn and smelling of dust. He's not like the others. He doesn't need the usual artifice. He doesn't demand anything from you that isn't real. And over time, that has made this — what you do for him — something that feels almost sacred.

He's been through more than most people could bear but you see him in a way no one else does. It's a side of him that only you're allowed to see; the side of him that's still raw, still vulnerable and in need of care. You know the scars are more than just physical; they go deeper than the skin. The thing about Basil is that, despite the rage and the hurt that cling to him, he trusts you. He trusts you in ways that no one else does.

The door creaks open and you see his silhouette in the doorway. He's still wearing the bag over his face, like he always does when he's out in public. But when it's just the two of you, he lets it slip. And you're the only one who gets to see him without it. His eyes are weary when he meets yours but they soften when he sees you. He doesn't say anything at first — he never does right away — but the look he gives you speaks volumes. It's a wordless welcome, an invitation.

You smile at him, soft and warm, and push yourself off the wall. You move toward him, the sound of your wedges on the veneer a small, steady rhythm.

"I was starting to think you forgot about me." You tease, voice light, though you can see the tension in his shoulders. Basil doesn't smile but the smallest flicker of something — relief, maybe — passes through his gaze. He steps aside to let you in, his movement almost mechanical, like he's already rehearsed it. You walk into his apartment, the familiar smell of pizza and burning greeting you. It's small and cluttered but it's his. And, in that way, it's enough.

Once inside, you slip off your coat and hang it carefully on the hook by the door before turning to face him as he pulls the bag off his head. "Hey there, sweetheart." You smile softly and his frame seems to lose some of its tension as he leans against the doorframe.

"Hey." He replies softly, voice small, gentle. You're much taller than him, especially in your wedge heels, making him eye-level with your generous bust, currently on display with the low neckline of your dress. It's not overly revealing, not like some of the outfits you wear to work. It's professional and mature, making you feel almost like a mother coming home from her office job. He likes it too.

"How've you been?" You ask and he peers up at you, swallowing hard, his hands twitching slightly by his sides as he resists the urge to touch you already.

"I-I've been okay." He manages and you lean down, keeping his gaze.

"Come and give Mommy a kiss then, Basil." His eyes widen slightly but he doesn't hesitate, stepping closer and resting his hands on your hips before pressing a soft kiss to your lips, leaving slight red smears from your lipstick. When he pulls away, his cheeks are flushed in that cute way he gets whenever you're around. You thread your fingers into his hair, manicured nails lightly scratching his scalp, and you slide your tongue into his mouth, pulling his body flush against your own. There's a little moan against your mouth and his arms wrap tightly around your waist. He's sucking on your tongue and tasting your lipstick as well as the glass of wine you had with your last client.

When you finally release him, you smile and pet his hair, his chin resting on the soft swell of your cleavage. "Come on, let's sit on the couch and you can tell me how your week's been, okay?" He likes how you direct him, never demanding obedience but he gives it anyway. He nods, allowing you to lead him into the familiar depths of his dark apartment, the world feeling so much safer with his hand in yours.

You sit down on the couch and he does the same, though he lies down with his head in your lap, laying on his back and gazing up at you, dark eyes lidded and brimming with adoration. You cup his face, gently running your knuckles along the fading, puckered scar across his face. He doesn't mind when you touch it. You soothe him, wherever you touch, and his scar is no different. "So what've you been up to?" You ask and he sighs contentedly, eyes fluttering shut.

"Not much, really. Spent most of my time reading." He answers. He never leaves his apartment but you always ask, on the off chance that he might've attempted to step foot outside. Not today though, it seems. Your hand moves to the centre of his chest, slowly rubbing along his sternum, through his t-shirt, between the panels of his button-up.

"But you've been alright?" And he nods.

"Yeah, I've been alright. Just...lonely, you know?" He admits, looking up at you wistfully. His hand finds your own on his chest, linking your fingers together. "It's so much better now you're here though." Your smile widens and you lean down to kiss his forehead, leaving a lipstick stain there. He likes them; looking in the mirror and seeing lipstick kisses on his forehead, cheeks and neck. He doesn't like pain so hickeys don't work but he still likes evidence to remind him that you were there.

"I missed you too, sweetheart." His eyes light up at the gesture and the nickname, his fingers squeezing your own.

"I missed you more." He murmurs, his voice barely more than a whisper. Your hand leaves his and drifts down to the hem of his shirt, lifting it slightly, to rest your hand on his bare stomach, lightly playing with the soft, downy hair that disappears under the waistband of his pants.

"Were you a good boy for Mommy? Did you make sure you took care of yourself every day?" And he nods again.

"Yes, Mommy. I ate all my meals and took my vitamins like you told me to. I even went to bed on time every night." He tells you proudly.

"Good boy. But did you take care of yourself?" You ask and his cheeks flush a handsome shade of pink.

"I-I... Uhh... Yes, Mommy..." He stammers out. "I took care of that too. Everyday, just like you said." And you beam at him warmly.

"Good. It helps with stress, you know. And I know how anxious you get when I'm not here to help." He nods again.

"It really does help." He admits. "I jack off every morning in the shower and before bed too. It...calms me down." He hesitates before speaking up again. "It's not as good as when you do it though." Your hand moves a little lower, rubbing his inner thigh.

"What do you think about when you do it?" You ask and he catches his bottom lip between his teeth.

"You. I think about you a lot when I jerk off, Mommy. I imagine your hands on me instead of mine. Or your mouth..." You lightly drag your nails along the seam of his pants. He's slowly getting harder, blood rushing south as you follow this line of questioning, touching him all the while.

"Do you last long when you think about me?" He shakes his head quickly.

"N-No, Mommy. I never last long when I think about you." He swallows hard. "Just the thought of you touching me is enough to get me hard and I usually cum in a few minutes, i-if not seconds..." You place your palm against his crotch, feeling the slow pulse there as he thickens, hearing his breath hitch as his hips involuntarily push up against your hand.

"Good boy, Basil. Mommy thinks about you too when she does it." You tell him and a shiver rushes through him at the thought. You gently squeeze him through his pants.

"You do? What do you think about when you jack off, Mommy?" He asks and you smile, running your fingers along the outline of his erection through his pants.

"I think about my precious boy, of course. I pull down my panties and pull out my big, thick cock and I stroke it while thinking about you, begging for it in your pretty mouth or in your tight, little hole." You tell him, the filthy words at odds with your soft tone, his cock throbbing under your hand.

"D-Do you cum a lot when you think about me like that?" You give him another squeeze and he bites back a desperate whine.

"Mhmm. It feels really good."

"M-Mommy, please..." He whimpers, hips bucking as you squeeze him through his pants. "If you keep doing that, I'm gonna get really hard and really close to cumming already." His cheeks redden as he worries his lip between his teeth, trying to stave off the heat flooding his lower half.

"That's okay, sweetheart. Mommy's here to help get rid of aaaall that nasty tension." You keep teasing him through his pants. He's not overly big but you don't mind.

"Feels so good when you touch me like this... You know how I get all turned on and uncomfortable when I'm stressed out?" You nod, tilting your head as you gaze down at him. "I get so hard, Mommy." He whispers, voice trembling slightly. "And I just wanna fuck o-or get fucked so bad. Sometimes I just lay in bed at night and jerk off to thoughts of you fucking me until I tire myself out." As you listen, you unbutton his pants and slide down the zipper, gently pulling him free of his boxers. He's leaking a lot already, stringy trails of pre sticking to your fingers as you run them along his bare cock. He gasps, his pushing up into your grip.

"I bet that feels really good, sweetheart."

"Mommy..." He spreads his legs a little wider and you give him a slow stroke, watching him leak.

"Mmm~ Look how big you are already, hm?" You tease and he whines.

"Please touch it more..." He pleads and you wrap your fingers around the shaft a little tighter before starting a slow rhythm, watching the foreskin dip up and down with every movement. "Ahh, fuck... Mommy..." He squirms slightly, his breath growing heavier with each stroke. "Your hand feels so much better than mine..." You lean down and press another kiss to his forehead.

"Because I know just how you need to be touched, sweetheart." You tell him and he nods before reaching up hesitantly, cupping one of your breasts through your dress and squeezing lightly.

"You're doing it perfect. Just like you always do..." He arches into your touch, a moan escaping as he squeezes your chest, pawing at you like a needy puppy. He's leaking almost continuously now, making the slide slick and easy over his cock. "M-Mommy... I'm getting close..." He warns breathlessly and you pull down the neckline of your dress along with your bra. His fingers immediately go to play with your nipples, rolling and pinching them, earning him a soft, contented sigh from you.

"You like them?" And he nods quickly.

"Mhm. I love your big, soft tits." He huffs and your free hand cups the back of his head, bringing him closer. His lips part before sealing around one of your nipples and you let out a low moan as he suckles, swirling his tongue around the sensitive bud. He bucks up into your hand, his breath coming in hot gasps against your breast, as you run your fingers through his thick, dark curls.

"Ohh... Good boy. Such a good boy for me." You sigh as he kneads and massages your other breast with his hand.

"Mmmph... Mommy..." He feels so safe, here with you. Wrapped in a cocoon of maternal affection, gentle touches and soft, warm flesh. It's all the attention he could ever ask for, safe in the knowledge that you'd never judge or shame him for his scar, his behaviour or even his neediness. His cock throbs heavily against your palm, the head a deep pink as he grows close. "Gonna cum..." He sighs, the words half-muffled by your breast.

"Go on, sweetheart." You encourage him and he doesn't hesitate.

Basil lets out a muffled curse around your nipple, body tensing as he spills into your hand. You keep stroking him through his orgasm, his cock pulsing and twitching, spilling thick ropes of cum onto your fingers. His eyes roll slightly but he still keeps suckling at your breast, quiet whines and whimpers huffing against your skin.

Finally, he pulls away with a soft, slick pop, gazing up at you with glazed, satisfied eyes. You pull your hand away, your fingers glistening in the low light, sticky with his load. "Mm. You made such a mess." You tell him and his brows knit slightly.

"S-Sorry." He manages, his breath still shuddery.

"It's alright though. Mommy can clean it up." You lift your hand to your lips and lick your palm clean before sucking his spend from each of your fingers, swallowing down all you gather on your tongue. He watches with wide eyes and moans softly, his spent cock twitching weakly.

When you finish, you look down at him. "Now, did you get yourself nice and ready before I arrived?" You ask and he nods eagerly. "Good boy. Can you get up and take off your pants for me?" And he swallows hard, standing up on shaky legs. He hooks his thumbs into the waistband of his pants and underwear, leaving himself in just his t-shirt and button-up. "Let me see all of you, sweetheart." You stand and help lift off his shirt, kissing his scarred cheek as you fold up his clothes and place them on the arm of the couch. "Mm. Such a pretty boy." You reach back and unzip your dress, unclasping your bra and lowering your panties, leaving you in only your wedge heels, your large cock hard and bobbing up against your stomach.

Settling back down on the couch, you cup one hand around a breast and curl the other around your cock, pumping slowly. "Mmm... You get Mommy so excited, Basil."

"Y-You're so hot, Mommy..." He breathes as you reach onto the coffee table to grab the bottle of lube that lies there. You squeeze a generous amount into your palm before slathering it along the length of your cock, giving yourself a few more slow strokes before lifting your gaze to his.

Does my precious boy wanna come for a ride, hm?" You ask and he nods eagerly.

"Yes, Mommy." His cock is already filling out again, despite having just spent itself. He steps closer, dark eyes fixed on your slick, shiny shaft. "Can I... Can I get on top?" He asks softly, already knowing the answer but wanting to hear it from you.

"Of course, you can, sweetheart. It's waiting for you." You purr in reply and he nods, climbing into your lap, knees on either side of your hips. He reaches back to guide your cock against his rim, his other hand holding onto your shoulder for support, biting his lip as he slowly sinks down onto you.

"Holy...fuck..." It took a long while to get him ready for you when you first started coming but he's used to it by now, sinking down easily onto your cock.

"That's it. Mmmnn... It's so warm and tight inside you." You sigh as he turns back to face you. Your hand falls to his abdomen, as if willing to feel yourself inside him. "Does it feel good, Basil? Having Mommy's big, hard cock inside you?"

"So fucking good..." He whines, head falling back as he starts to bounce his hips in a slow, deep rhythm. He loves the feeling of being completely filled up by you, your cockhead pressing against his insides, sliding across his prostate and sending tingles all throughout his body. "Your dick's so big, Mommy..." Your hand finds his hip, guiding his movements. "So deep... Like I can feel it all the way in my belly..." With your free hand, you pull him closer, lips pressing against his, lipstick smearing across his mouth as you kiss him deeply.

Eventually, you pull away and tuck his face against your neck.

"Let Mommy take over." His body relaxes perfectly against your own and he nuzzles the side of your neck, planting little kisses there as his arms wrap around your neck. He gives up control, stilling his hips, and you hum in approval. "Good boy."

Your hands grasp his hips and you roll your pelvis up to meet his. The angle change is everything, focussing on sliding your cock against his prostate just the right way. His eyes roll back and he clings to you tightly, his mouth falling open.

"M-Mommy... F-Fuck... Right there..." He whines against your neck, his cock already leaking again, leaving sticky strings on your stomach. "So good... So fucking good..." He's reduced to whimpers and moans now, his body jerking with each deep thrust, drool dripping down his chin as his mouth hands open. "G-Gonna cum already..."

"That's okay, sweetheart." You pant out, your own breath hitching as you relish the sensation of being inside him, his body tight and warm around you. "You can cum. Mommy's gonna finish soon too." His movements become a little more erratic as he climaxes again, cum spurting up onto your stomach and chest. He cries out, burying his face into the crook of his neck, clenching down around your cock as his body goes stiff, milking you desperately. "Ohh, you're squeezing me..." You leave a trail of kisses along his neck, pressing more lipstick stains onto his skin. "Get ready, sweetheart. Mommy's about to cum..." He only moans in response, taking in deep, shaky breaths, as you keep rocking your hips against his.

Your fingers curl tight around his hips as you sink deep inside him. He's still pulsing around you, little spurts of cum oozing down his shaft, as he reaches the end of his orgasm only for it to be prolonged as you finish inside him, coating his insides and warming him from the inside out. His eyes widen in shock and pleasure, mouth agape as he savours the sensation.

"F-Fuck, Mommy...!" He feels you pouring yourself into him, filling him. "Mmmmnnn... So much... Too much... It's leaking out... Mommy, it's too much..." He whimpers and you roll your hips, pushing your load deeper inside him, lewd squelching noises filling the room as you fuck your load into him, rubbing the small of his back.

"Such a good boy, Basil. Taking all of it like this..." You praise him and he keens into the touch, his body limp as it rests against your own.

Finally, you stop moving as your cock starts to soften. Eventually, it pops free and a good amount of cum leaks out onto your thighs and onto the floor. You hold him close, turning his head and kissing his drool-covered lips. He's completely out of it but he kisses you back sloppily, his tongue lazily tangling with yours, as he melts against you, his body still giving occasional twitches and jerks from the aftermath.

You sit there for some time, savouring the afterglow and letting him languish in your arms for a while, completely fucked-out, every one of his movements sluggish and slow. He seems to come back to himself, slowly but surely; his breathing levelling out again. "When you feel like it, I want you to go and get ready for bed while Mommy cleans up and gets dressed, alright?" You whisper in his ear, pressing another kiss to his temple.

"Mhmm..." He nods slowly. "Thank you, Mommy." He finally manages to push himself up onto unsteady legs. "I'll...go get ready for bed now."

"Good boy." You praise him and he staggers slightly as he heads toward the bathroom, your load leaking down his inner thighs as he goes.

You're quick and efficient; standing and wiping yourself down before slipping back into your clothes and touching up your makeup. You make sure to clean up any wet spots on the floor, dropping any dirty tissues in the trash. You hear him getting in the shower and brushing his teeth as you fix your hair and spritz yourself with a little perfume from your purse. You look perfect again, as if nothing even happened.

Walking into his bedroom, you busy yourself with making the bed and getting out a clean set of pyjamas for him to wear, laying them out at the foot of the bed, now fully made.

He steps out of the bathroom a few minutes later in a towel. His steps are still a little bit wobbly as he approaches, though a lazy, contented smile quirks at his lips, his eyes still glazed over with post-orgasmic bliss.

"Mommy." He calls out and you turn around after pulling back a corner of the comforter.

"Mhm?" And he pauses.

"Nothing. Just thank you." He pulls on the fresh pyjamas, climbs into bed and settles down, his hair still a little damp from the shower. You tuck him in and stroke his scarred cheek, brushing a couple of loose curls from his face.

"Mommy has to go to work now, okay, sweetheart?" You tell him and he turns his face into your touch, nuzzling your hand.

"Mmm... Okay, Mommy. Love you." He's halfway asleep, his voice sleepy and soft. You press your lips to his forehead one last time, leaving a lipstick kiss there for him to smile about tomorrow.

"Sleep well, alright?"

"Mmhm..." He murmurs before he drifts off completely, curled under the blankets.

You quietly step out of his bedroom and close the door with a soft click. Passing by the kitchen, you pick up the folded-up bills on the countertop; the usual payment for your visits. Plucking up your purse and coat from beside the door, you slide the bills into your purse and open the door.

You'll be back next week.

Goodnight, Basil. Take care of yourself.

Notes:

👻 HAPPY HALLOWEEN!! 🎃

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