#helluvabossreaderinsert

Fandom: HelluvaBoss

Pairing: Striker / Trans reader

Rating: M for swearing and sexual content

Downtown Imp City was always loud however when you pay for a penthouse suite in the core luckily sound proofing was included as a standard. Trudging from her modern office a medium sized imp with long black hair with grey streaks, almond shaped yellow eyes, large crescent shaped horns, and a white scar across her nose made her way to the living room. (Y/N) flopped down on her white couch with a heavy sigh just as her phone went off causing the furrow to deepen on her brow mainly because she knew who it would be. Checking her phone revealed it was exactly who she thought, Striker was an imp she’d met at a bar over 6 months ago and apparently, she’d left an impression with the short conversation they’d had because he started showing up randomly. Eventually one evening Striker had brought dinner right to (Y/N)’s door with the invite of eating together for the first time, since then they’d done that several times along with going out to bars, going places together basically…well…dating. Unfortunately, there was one thing they’d not done yet that most couples usually had by this time in their dating and that was sex, Striker had obviously made advances, laid hints, even initiated heated make out sessions, but every time they got close to that moment (Y/N) would shut it down. Staring at her screen the text message written there was asking for another dinner meet up which was fine however (Y/N) knew that the potential of things escalating were highly probable and it wasn’t like she didn’t want to sleep with Striker after all the pale imp was hotter than literally hell, but she had a secret she wasn’t certain how he’d react to.

Against her own better judgment (Y/N) replied with a ‘ok’ before getting up to go take a shower so she could start getting ready. A few hours later there was a knock at (Y/N)’s door that she promptly walked over to answer wearing a bright yellow sundress with her hair straightened. Opening the door Striker was standing holding a couple white take out bags along with that wide smirk he always wore, (Y/N) quickly invited him in with a big smile.

“Good to see Ya Darlin’,” Striker greeted giving (Y/N) a peck on the cheek on the way by.

“Same,” (Y/N) responded closing the door once Striker was inside

Striker laid the food out on the marble countertop in (Y/N)’s kitchen while she got the plates allowing them to each grab what they wanted for food. They took their food into the living room where (Y/N) put on some music in the background that way they could talk while eating sometimes they’d watch a movie however because they’d not seen each other for a while tonight was a talking sort of night. Eventually (Y/N) switched the music to a TV show for them to watch after they were finished eating, Striker had shed his jacket as well as popped the buttons on his vest while propping his feet up on the coffee table to relax. (Y/N) curled up beside Striker resting her head on his chest when he casually leaned down to nuzzle her hair instantly drawing the imp’s attention upwards, Striker smirked slightly then leaned in to press their lips together in a gentle kiss. As the kiss progressed Striker caressed his hand along (Y/N)’s thigh barely sliding it under her dress before (Y/N) suddenly grabbed his wrist while pulling from the kiss only to avert her gaze, brows furrowing upwards in an apologetic way.

“I-I’m sorry…” (Y/N) whispered out, releasing Striker’s wrist

“It’s fine…look this ain’t the first time Ya have stopped me…is there somethin’ wrong?” Striker asked gently caressing his knuckles over her cheek.

“Not wrong necessarily…I…I’m worried that once you see me…you won’t want to date me anymore,” (Y/N) worriedly explained.

“Is that all? Darlin’ I don’t care whatchya look like under these cloths…I promise I won’t judge Ya,” Striker assured (Y/N) with a light chuckle.

“Really? I’m not sure…” (Y/N) trailed off in surprise

“Look, I won’t continue if Ya don’t want me ta…but…might I suggest we try,” Striker suggested with the lightest and gentlest touch to (Y/N)’s bare knee. (Y/N) considered it very carefully, but seeing the tender look on Striker’s face she finally relented leaning in for another kiss.

Striker moved from (Y/N)’s thigh to her covered side, sliding his hand around to the small of her back to pull the other imp closer. Deepening the kiss Striker brought his free hand to (Y/N)’s chest, gingerly kneading from one breast to the other making her moan into his mouth. (Y/N)’s hands caressed along Striker’s chest down his sides then back up, loosing herself in the sensations of finally indulging in the touch of another. Striker started nipping along (Y/N)’s jawline to her neck as he started caressing her thigh again, sliding from front to back occasionally sliding to her ass.

“Hmm, a thong huh? Didn’t figure Ya for that,” Striker seductively chuckled against (Y/N)’s pulse point making her shiver.

(Y/N) let out a breathy moan as she slid her hands down to palm Striker through his jeans, sliding along the outline of his member eliciting a long moan from the pale imp. (Y/N) used nimble fingers to pop the button on Striker’s jeans followed by pulling down his zipper providing some much-needed relief however this prompted the pale imp to slide his hand around to (Y/N)’s crotch and immediately he stopped. (Y/N) instantly froze with eyes wide at realizing she’d been so lost in the moment she hadn’t even noticed Striker moving in that direction. Striker had a look of surprised confusion laced all over his features as his hand rested on what was obviously a half hard cock and not a vagina like he’d been expecting, he began to pull away ever so slightly.

(Y/N) immediately flushed bright red as her eyes turned glassy, standing abruptly she covered her mouth with one hand then headed swiftly in the direction of her bedroom. Striker stood moments later quickly snatching the other imp’s forearm as gently yet firmly as he could to get her to remain.

“(Y/N), Darlin’…what’s wrong? Hush,” Striker wondered as he noticed she’d started crying, pulling her close.

“I-I’m sorry…I should have told you sooner…I was afraid you’d leave though…guess it doesn’t matter now…” (Y/N) sobbed, holding Striker at arms length

“Why? Because Ya got a dick? Got news for Ya, I got the samethin’,” Striker chuckled in a reassuring manner.

“Y-You…don’t care?” (Y/N) furrowed her brow in confusion as she met Striker’s gaze

“Ha-ha, (Y/N), I’m a hitman who travels everywhere in hell do Ya really think I haven’t slept with every kind of hell being there is? I can’t really be picky, if it’s good sex then who cares? And if Ya care about someone…what’s in their pants shouldn’t matter,” Striker explained ending with such a loving gaze it nearly melted (Y/N) from the core out.

“So…your okay with this?” (Y/N) asked seeking confirmation

“Darlin’ I know my way around a dick as much as a pussy and it don’t matter which Ya have,” Striker once again assured her with a smile.

Relief didn’t even touch the feeling (Y/N) had in this moment as she lunged forwards to crash their lips together, one hand immediately finding it’s way into Striker’s hair while the other slipped under his long sleeved black shirt to caress over his abs. Striker chuckled into the kiss then pressed close to (Y/N), slipping his knee between her legs while pressing one hand to her lower back as the other went back to kneading her breasts. A few moments later Striker pulled from the kiss leaving (Y/N) with a pink blush across her face.

“Lift Yer dress,” Striker instructed, pulling back.

(Y/N) nodded in approval as she stepped backwards before pulling her dress up causing her blush to deepen as Striker released an approving hum at what he was seeing. Striker stepped forwards then took a knee in front of (Y/N), placing his hands on the backs of her thighs. (Y/N)’s cock was straining against her thong, tip barely peeking out the top as a bead of precum sat on it. Leaning forwards Striker licked across the peeking head, pressing the tip of his tongue into the slit before swiping across it once more making (Y/N) shudder. Striker caressed his hands up (Y/N)’s thighs to hook his thumbs on the strings of the thong, gingerly pulling it down allowing his tongue to follow the fabric down (Y/N)’s cock.

(Y/N)’s hands clenched on her dress while she bit down on her lower lip as Striker started sucking on the head of her cock. Striker brought a hand to (Y/N)’s mid shaft stroking while he sucked down, caressing his other hand over her firm ass quickly eliciting moans from (Y/N) causing her hips to start thrusting forwards. Striker choked slightly when (Y/N) gave a thrust forwards taking him off guard, moving his hand to (Y/N)’s hip to stop her thrusting he pulled off.

“Whoa, easy there Darlin’,” Striker chuckled with a slight cough

“Are you alright?” (Y/N) asked a little breathlessly with an embarrassed look on her face

“Yeah, I got a bit too much gag reflex for Ya to throat fuck me though,” Striker responded teasingly

“Oh…sorry, I didn’t even realize…” (Y/N)’s blush grew 5 shades deeper

“Its fine,” Striker assured her, gently stroking his one hand along her member while sliding his other hand along her ass. Striker leaned forwards to kiss along her lower abdomen as his fingers of the hand on (Y/N)’s ass slipped between her crack to teasingly rim her hole. Releasing a shuddering moan (Y/N)’s knees nearly buckled as her breathing came in heaving pants. Striker slipped a single finger into (Y/N)’s hole.

“Yer tight…Ya ever been fucked before?” Striker asked, nipping lightly at (Y/N)’s lower abdomen

“N-No…I-I’m a…virgin…ah!” (Y/N) breathed out

“Alright…come on,” Striker stated shifting both hands to scoop (Y/N) up into his arms bridal style making her yelp in surprise. Striker carried (Y/N) into her bedroom where he put her down at the foot of her bed.

“Bend over the bed,” Striker instructed gently

“Okay,” (Y/N) agreed, following Striker’s instruction

Striker pulled the dress back up to reveal (Y/N)’s ass, squeezing the firm flesh in his hands before spreading her cheeks causing (Y/N) to bite on her index finger of one hand while gripping the sheets with the other hand. Striker leaned in with a single swipe of his tongue across her entrance, rimming it then sucking liberally at the ring of tight muscle eliciting a series of shuddering moans from (Y/N), getting louder as Striker started pressing his tongue into her. (Y/N) was swiftly rendered into a moaning mess at the mercy of Striker’s talented mouth, experiencing the most incredible sensations that she hadn’t ever felt. Striker was alternating between caressing her thighs, balls, back, and ass while he continued tongue fucking her entrance. Striker pulled off (Y/N) making her whimper in disapproval, body quivering as her cock drooled precum between her legs.

“Do Ya have any lube lyin’ around?” Striker asked

“Y-Yeah…side table…drawer,” (Y/N) panted out, glancing over her shoulder

“Perfect, stay put. Ha-ha,” Striker chuckled as he swatted (Y/N)’s ass playfully

Opening the drawer Striker found the bottle of lube that appeared to have been barely used, turning around with the bottle in hand Striker stopped for a moment to admire (Y/N). The other imp was watching him with lidded lust filled eyes, face flushed while breathing heavily all wrapped up in that gorgeous little yellow sundress. Humming in approval Striker moved back behind (Y/N) except this time he remained standing, drizzling some of the lube onto two of his fingers before swiping them between her cheeks right across (Y/N)’s entrance to assure it was slick. Gently the pale imp pressed one finger in to the first knuckle eliciting a small inhale from (Y/N), his other hand caressed up underneath the dress along her back.

“Hmm, yer so beautiful,” Striker complimented sometime later as he worked (Y/N) open with two slick fingers, body draped partially over top of (Y/N) with his free hand currently caressing along her torso while his mouth nipped and kissed at every piece of exposed flesh it could find. After being able to easily insert a third finger Striker massaged around for a few minutes then pulled his fingers free resulting in a very disapproving whimpering groan from (Y/N).

“Striker…fuck me…please…” (Y/N) pleaded into the mattress where her face was currently buried

“Easy Darlin’, get on the bed and lay on yer back,” Striker instructed

(Y/N) crawled onto the bed then flipped over to lay on her back giving her the perfect view as Striker removed his vest then pulled off his jeans. (Y/N)’s eyes went wide as Striker pulled himself free of his boxer briefs not only was he thicker then she’d expected but his cock had spines running along the sides. Striker crawled onto the bed to settle between (Y/N)’s legs, gingerly sliding his hands up to slowly remove the sundress leaving (Y/N) completely exposed prompting her to instinctually cover her breasts making Striker chortle at the cute reaction.

“Hmm, prettier than a sunrise on the wrath plains,” Striker complimented

“Um…thank you…but um…” (Y/N) trailed off as she looked pointedly at Striker’s cock

“Hm? Oh, don’t worry Darlin’ they’re not as dangerous as they look,” Striker smirked running his hand over his own cock revealing the spines to be malleable like hair that’s a little stiffer.

(Y/N) gave a nod prompting Striker to move into position, pressing the head of his cock to (Y/N)’s entrance making her tense for a moment before forcing herself to relax. Striker gently pushed forwards to slip the head of his cock into (Y/N) eliciting a sharp inhale from the other imp, Striker massaged his free hand along (Y/N)’s thigh in a soothing manner.

“Relax, it’s goin’ ta hurt a lil,” Striker warned

“Right…” (Y/N) breathed out

“Don’t worry…I’ll go slow,” Striker assured (Y/N), caressing his hand up to her stomach where he splayed his fingers.

Striker stayed true to his promise pressing forwards inch by inch making sure to apply lube for each inch to assure (Y/N) was comfortable. (Y/N) did wince a little as Striker slipped his first set of spines into her but the further, he slid in the further she stretched making it easier with each inch to take Striker till he was fully seated inside her just waiting for her to adjust. (Y/N) moved her hands to the bedsheets revealing the imp’s voluptuous breasts, her nipples were a pale pink and perky.

“I don’t want Ya to be surprised but when I cum my spines flare so Ya might be a little uncomfortable,” Striker informed (Y/N).

“Okay,” (Y/N) responded still breathless as she waited in anticipation for him to move

Striker peppered kisses along (Y/N)’s torso before pulling back to pull off his black, long sleeve shirt revealing his muscular torso. Leaning back down he placed his hands on the mattress to either side of (Y/N)’s body, eyes trained on (Y/N)’s face as he gave an experimental roll of his hips earning him a wanting moan from (Y/N). Striker started a slow gentle rhythm occasionally speeding up or changing his angle to test (Y/N)’s reactions which for the most part were open mouthed moans and whimpers of pleasure.

“Striker…please…I want to cum…” (Y/N) pleaded as she felt her orgasm approaching

“Ya will…come on Darlin’,” Striker assured her, his southern drawl deeper then before.

Striker leaned down to latch his mouth around one of (Y/N)’s perky breasts, grazing the nipple lightly with his teeth as one of his hands wrapped around her shaft. (Y/N) let out a series of whimpering hums as she bit down on her bottom lip, head tossing backwards at the multiple sensations.

“Tell me…whatchya need…faster? Deeper? Both?” Striker asked, nuzzling against her breast

“D-Deeper…please…” (Y/N) responded breathily

“Alright,” Striker confirmed pressing deeply before pulling slowly back out only to press in again, stroking in time with his thrusts.

“Oh…fuck…that’s…that’s good…” (Y/N) panted out

“Feels good?” Striker asked with a grunt as he snapped his hips forwards

“Y-Yes…c-could you…go a little faster?” (Y/N) asked

“Anythin’, you want Darlin’,” Striker confirmed instantly picking up the pace

“Oh…fuck…Yeah, I’m close…” (Y/N) panted out

“Good…cum for me, come on Darlin’…. cum with my dick up yer ass and my hand on yer cock,” Striker encouraged

Moments later (Y/N) arched her back with an open-mouthed moaning cry as she spilled cum all over Striker’s hand as well as her own stomach, his hand gingerly milking her through the orgasm while he continued to thrust. Striker removed his hand from (Y/N)’s cock after a few moments to place it on the bed, his grunts were getting louder as his tail rattled and his thrusts became sloppy. (Y/N) reached up to caress a hand along his cheek while still panting heavily drawing the pale imp’s attention back to her face.

“Cum Striker…cum inside me…” (Y/N) encouraged

Striker gave a guttural groan as his eyes squeezed shut and that’s when (Y/N) felt it, gasping she felt Striker’s spines flare inside her and his hot cum spill along her insides. (Y/N)’s hands flew to grab Striker’s upper arms with a series of muffled uncomfortable whimpers as she felt far too full and was being stretched further. Still working through his waves of pleasure Striker quickly caressed his hand up (Y/N)’s side then cupped her face while making soothing sounds.

“Sshh, hush Darlin’…I told Ya it would be uncomfortable…are Ya in pain?” Striker asked, furrowing his brow up in concern.

“Not really…I’m so…full…” (Y/N) stammered

“Okay, just breath and try to relax...you’ll adjust, and I’ll be able to pull out soon once my spines smooth back out,” Striker reassured (Y/N) as sweat beaded on his flesh.

“O-kay…” (Y/N) breathed out trying to relax

Striker pressed gentle kisses to (Y/N)’s cheek to her jawline then down her neck before nuzzling just underneath her ear. After only a few minutes Striker started gently pulling out till he easily slipped free eliciting a relieved little sigh from (Y/N), sleepily watching as Striker slipped from the bed to walk out of the bedroom only to return moments later carrying his duffle. Striker stopped in the on-suite bathroom upon re-entering the bedroom, running some water for a few moments before returning with a damp cloth, tossing his duffle on the bed. Striker pulled out a tube from his duffle before crawling back up on the bed to start gently cleaning (Y/N) up with the warm cloth, making (Y/N) hum appreciatively. Once Striker finished cleaning (Y/N) up he squeezed some cream out of the tube he grabbed.

“This’ll help,” Striker simply stated before gently applying the cream to her over stretched hole eliciting a slight hiss at the little bit of aching pain that flared from the touch.

“Oh…right,” (Y/N) flushed slightly from realizing that probably in a few hours her ass was going to be a little tender from having had sex for the first time.