#helluvabossfanficiton

Fandom: HelluvaBoss

Rating: M

Pairing: Criminale

Crimson hated when things interrupted his usual schedule a fact everyone knew well hence why many gave the mob boss his space however sometimes it wasn’t a person who interrupted his time. Crimson sat at his massive oak desk in the library casually doing his usual paperwork when he felt the tell-tale signs of his rut starting to creep their way up his spine. Crim irritably growled to himself because of course on the night he had a stack of papers to attend too this would happen luckily Alessio walked through the large double doors to the library just as Crimson was about to pick up the phone to summon him.

“Ale, I require something of you,” Crimson declared catching the shark off guard for a moment before he obediently approached the don’s desk.

“Go to my bedroom and strip down,” Crimson bluntly ordered once again eliciting a surprised look from Ale.

“Um…yes sir,” The answer came with a hint of a question.

“I’m in rut and you know what that means…now go get ready, I’ll be up in a moment,” Crimson elaborated having picked up on Alessio’s slightly confused tone.

“Ah, yes sir, I’ll go now,” Ale obediently stated heading back out the double doors he’d come through moments before.

Now to anyone else this interaction might have seemed strange however to the duo it wasn’t anything new, Crimson had started going into rut regularly after marrying his late wife unfortunately after her…disappearance, he’d not stopped having his regular ruts meaning he needed an outlet. Ale had been the only one Crimson trusted in the slightest, although he wasn’t pleased with having to fuck a guy it was the best option considering getting even a stripper was dangerous now a days. Crimson had dealt with the concept after all it was simply to satisfy an ich once every few months, making Ale no more then a sex doll to Crimson in those moments at least in his mind.

Ale did as he was told heading to the don’s private room where he made certain the door was shut before stripping down. Ale would always be there for anything Crimson needed, ANYTHING, he wasn’t ashamed nor hurt by the fact Crim used him to pleasure himself during his ruts as far as Alessio was concerned this was just another part of his job. A long time ago when he was still foolish, he’d hoped for more from Crim however after years of serving under the don he’d learned better than to hope for anything more then what was already here, speaking of learning Ale had also learnt that Crim didn’t care about his partner getting what they wanted during this time. Ale had brought a small bottle of lube with him into the bedroom and set to work prepping himself, bending over the bed while inserting a pair of lubed up fingers into himself with the hopes he had enough time to prepare before Crimson arrived.

Crimson opened the doors to his private bedroom a short time later revealing Ale just standing in the dimly lit room completely naked as he’d instructed. Pleased Crim closed the large doors behind himself then proceeded to remove his own clothing, draping them over a nearby armchair however this was where the routine changed. Crimson wondered over to his closet where he pulled out a length of rope causing Ale to eye him with both suspicion and curiosity. Crim walked over to stand right in front of the shark with the rope in hand, giving it a snap that made Ale narrow his eyes slightly and furrow his brow.

“Turn around,” Crimson instructed.

Ale did as told although it was a little hesitant, whipping his head around moments later when Crim suddenly yanked one of the shark’s arms behind his back swiftly followed by the second. Crimson proved his skill with rope as he tethered Ale’s wrists to one another, he also proved his stocky stature shouldn’t be taken lightly because the imp was incredibly strong, manhandling Ale to turn him around then shoving the shark backwards onto the bed. Ale grunted as his back hit the mattress, scooting up as much as possible before Crim started crawling up between his legs, shoving them apart aggressively. Ale tipped his head up to the side as a submissive gesture that apparently was welcomed because Crim latched onto the shark’s neck with a series of aggressive bites with undertones of growls. Crimson’s tongue lapped up the blood that ran from the marks he left, moving down to leave a mark on Ale’s chest all of which wasn’t for Ale’s benefit, these were possessive markings brought on by crimson’s rut instincts nothing more. Ale let out a pained groan as the imp sunk his fangs into Ale’s inner thigh right before grabbing onto the sharks’ hips with his talons, pressing his girthy cock right into Ale with no warning or prep fortunately the shark had done that earlier.

“Ugh…shit…” Ale cursed under his breath.

Crimson sunk balls deep in one thrust only to pull almost all the way back out then shove back in. The pace was brutal as usual but as usual Ale just laid there to take whatever Crimson dished out unfortunately with his wrists tied behind his back Alessio couldn’t touch himself like normal leaving both his dicks aching with want. Crim selfishly chased his own pleasure quickly reaching that point of no return, burying himself deep in Ale as he spilled into the shark with a grunting groan however, he didn’t withdraw. Ale braced for what he knew was coming and without fail Crim started up a second round instantly causing Alessio to groan, drawing his bottom lip up between his teeth. Hours passed with crimson spilling into Ale several more times till after about the tenth time when he was finally spent, withdrawing as he panted with sweat beading along his skin in the dim light while Ale panted heavily in turn, cocks flushed the same deep color as his cheeks as they ached for release. Alessio watched as Crimson raked his eyes over him, a small smirk building on his features at watching his own cum leak from Alessio’s ass while pre-cum drooled from the shark’s double dicks.

Ale closed his eyes to await Crimson to leave as he normally did which would allow Ale to take care of himself however tonight Crimson did something for the second time that surprised Ale. Alessio gave a sharp inhale as he felt a hand wrap around one of his cocks, immediately stroking swiftly causing his eyes to fly open to glance down. Crim was smirking as he stroked Ale’s left cock at first eliciting a confused furrow only to have it swiftly fade into a needy upwards furrow as he moaned through soft moans. Crimson grabbed Ale’s other cock with his other hand making sure to stroke in opposite intervals making Ale tip his head back with deep groans that turned into a full out cry when he came, arching his back as his body shook from the orgasm.

fandom: Helluvaboss

Pairings: Blitzo/Stolas, Stolas/original male character

Rating: M

Calus pushed open the clean white door with the golden ‘23’ on it, removing his hat in the process to hang on the coat rack just beside the doorway. The Dracony didn’t bother turning on the light instead he simply trudged towards the bed, stripping off various articles of clothing that he let fall to the floor before flopping down on the mattress in his boxer briefs with a heavy sigh. Barely managing to get comfortable Calus growled at the sound of his phone going off on the table next to the bed, the light from the screen illuminating the room as an image of Blitz appeared. Calus begrudgingly rolled slightly onto his side to pick up the phone with a slightly irritated ‘what?’.

“Hey Calus, hope I didn’t wake you, but I have a big favor to ask,” Blitz hurriedly spoke on the other end.

“What do you want Blitz?” Calus once again irritably asked.

“I’m off on a job that I can’t get back from for at least another week, but Stolas went into heat tonight so…” Blitz trailed off from his explanation causing Calus to arch an eyebrow in curious confusion.

“So…what? What exactly is it you’re asking?” Calus prompted, propping himself up on one elbow while furrowing his brow in confusion.

“I was just wondering if you could go help him out tonight?” Blitz finally asked, Calus’ brow arching upwards in surprise.

“Let me get this straight, you want me to go help fuck your mate through his heat. Is that what I’m understanding?” Calus double checked.

“Pretty much, yep,” Blitz confirmed.

“Well…is Stolas okay with this?” Calus inquired uncertain how to respond fully to Blitz’s request, pinching the bridge of his nose.

“Yeah, Stolas is totally down,” Blitz assured Calus.

“I mean…I guess it’s not a big deal, but it’ll take me about an hour or so to get back to Imp City let alone to the Goetia palace,” Calus informed the imp.

“That’s fine, is Striker with you?” Blitz inquired curiously.

“No, Striker’s off on another job and won’t be back for at least 2 weeks,” Calus answered simply.

“Alright, I’ll give Stolas a heads up,” Blitz explained.

“Sure,” Calus agreed.

With that Blitz hung up the phone followed by Calus doing the same, placing it back on the side table with a disgruntled sigh as he rolled onto his back, running his hands over his face. Calus got up to get redressed so he could check out to get on the road as soon as possible as to not leave Stolas waiting too long.

A little while later…

Stolas lay on the massive fourposter bed in the master bedroom propped against the headboard with pillows, legs spread as he thrust two fingers into himself. Slick sounds filled the air to mingle with Stolas’ panting breaths and whimpering moans, a dildo sitting next to him on the bed. Stolas picked up the large silicone member from the bed, sucking on the tip down the shaft till it was slick with his saliva before gingerly lining it up with his entrance. A moment later Stolas slid the dildo into himself with relative ease, thrusting it at a slow pace while carding the fingers of his free hand through his chest plumage. Stolas’ stomach ached from his heat begging for more then just a fake appendage and after Blitz had informed him that Calus was going to come ‘help’ with his heat it was now nearly overwhelming. Stolas pushed the dildo all the way inside himself with a needy moan just as there was a knock at his bedroom door, he wasn’t sure why he did it however as soon as the knock resonated through the bedroom Stolas grabbed his robe from beside him on the bed to pull up over the front of himself with the dildo still inside him.

“Stolas? It’s Calus, may I come in?” Calus’ voice sounded from the other side.

“Yes, of course,” Stolas permitted in a slightly strained tone.

Calus pushed open the large ornate door, striding inside while removing his hat to toss it on the shay he knew was on the other side near the small library. The room was dimly lit by candlelight and the distinct scent of a demon in heat hit him almost immediately, Stolas was propping himself up by one arm while holding his ratty red robe over himself with a deep crimson blush across his cheeks. Calus shrugged off his duster to throw it over with his hat then started striding over to the bed, stripping his black T-shirt in the process leaving the Dracony in only his jeans as the dim candlelight caused his white scales to emit an iridescent shimmer. Stolas admired Calus’ muscular torso for a moment only to pull his robe closer with a slight wince as his entrance oozed slick around the dildo still inside him, a panged ache radiating from his abdomen.

“I’m going to take it you’re alright if we just get started,” Calus assumed with a light chuckle.

“Um…yes…as long as you are,” Stolas shyly retorted.

“Then would you mind letting me see you?” Calus asked planting a knee on the bed, voice low yet gentle in the request.

“Uh…no…I don’t mind,” Stolas’ blush deepened as he felt slightly embarrassed, slowly shifting the robe away from his body, Calus’ eyes immediately moving to the toy firmly inserted in Stolas.

“Ha-ha, got desperate I see,” Calus lightly chuckled again, crawling up the bed.

Stolas averted his gaze to the side while squeezing his thighs together from embarrassment till Calus’ had wrapped around one of the Goetia’s thighs to spread them again. Calus settled between Stolas’ legs caressing a hand to his entrance where he teased the base of the dildo making Stolas release a gasping moan, slick instantly coating Calus’ fingers as it oozed around the toy.

“It’s fine, we’ll need to stretch you anyways if you want me to fuck you with my dick,” Calus explained in a low husky tone that made Stolas shiver.

Calus started thrusting the dildo casually as he leaned down to press sloppy kisses to Stolas’ stomach, nipping at his protruding hip bones before licking a strip up the princes abdomen. Stolas moaned needily, reaching up to caress his hands over Calus’ shoulders and upper arms as the knot in his stomach twisted further. Stolas was enjoying everything Calus was doing however he wanted to make the Dracony feel good as well, gently pulling Calus up till they could meet in a heated kiss which Stolas released an irritated whimper when he couldn’t quite get to Calus’ belt making him chuckle into the kiss.

“Easy, I’ll let you have a go in a moment,” Calus assured Stolas having immediately picked up on what he wanted to do.

“I…I just want to…” Stolas stammered slightly through panting breaths.

“I know…you want to reciprocate, that’s fine. First let’s get you stretched a little more. Trust me, you’ll need it,” Calus explained again his tone remaining gentle.

Calus gingerly removed the dildo making Stolas shudder then he slipped two fingers into Stolas, pushing against his walls then scissoring them. Stolas spread his legs, clawing at Calus’ back with desperate need as his heat grew worse, fever over taking him and the ache in his abdomen worsening. Calus lathed his mouth along Stolas’ jaw line, nipping occasionally as he started panting lightly and his pants growing slightly tighter.

“Would you like me to knot you?” Calus inquired in a whisper against Stolas’ ear.

“Absolutely,” Stolas confirmed breathily with a twinge of excitement under his breath.  

“Okay, then we need to get you stretched further,” Calus explained briefly, slipping a third finger into Stolas.

“Oh fuck…” Stolas moaned out.

“Luckily your heat is providing more then enough lube,” Calus commented, licking a strip along Stolas’ neck.

Calus continued to Stretch Stolas till the prince was begging to be fucked, his body squirming beneath the Dracony. Calus removed his fingers from Stolas to settle back on his haunches undoing his belt then his jeans before pulling them down to his mid thighs allowing the space to pull himself free of his boxer briefs. Stolas stared for a moment in surprise, he knew Calus was impressive however he’d not expected him to be bigger than Blitz. Maneuvering closer Stolas wrapped a hand around Calus’ base giving a firm stroke upwards earning him an approving hum in turn thus encouraging Stolas to continue. Stolas started stroking Calus’ length at a liberal pace, the Dracony leaning back slightly to brace on one hand as his hips started rocking into the prince’s grasp. Stolas increased his pace as Calus’ knot slipped from his sheath only to be halted by one of Calus’s hands wrapping gently yet firmly around his wrist.

“Whoa, slow down. You keep that up and I won’t last long,” Calus huffed a laugh.

“Oh…right,” Stolas sheepishly stated.

“Now, do you want to ride me, or do you want me to mount you?” Calus asked.

“Uh…um…perhaps riding might be easier,” Stolas assumed.

“If that’s what you’re comfortable with,” Calus stated.

Calus slipped from the bed to remove his jeans along with his boxer briefs, crawling back up to lounge against the pillows by the headboard. Stolas straddled Calus’ hips with the Dracony’s large cock lightly rubbing against his entrance from behind, waving his wrist a magical aura spread over his hand allowing him to open the bedside drawer to retrieve a bottle of lube. Popping the top on the bottle Stolas drizzled some onto his hand then reached behind himself to coat Calus’ cock in it, passing the bottle to the Dracony afterwards. Gingerly Stolas aligned with the head of Calus’ cock then slowly lowered himself onto it managing to get the head inside him, but he trembled with a harsh wince as the girth of Calus’ member started spreading Stolas further than he was used too. Calus gripped Stolas’ hips gently to hold him up as both Stolas’ palms planted on his chest.

“Easy Stolas, take your time,” Calus encouraged rubbing his thumbs in circles along Stolas’ hips.

“R-Right…ugh! You’re…bigger than…Blitz…” Stolas panted out.

“Ha-ha, don’t tell him that,” Calus joked with a soft chuckle followed by a huffed laugh from Stolas.

Calus cupped Stolas’ ass cheeks to help hold him up leaning forwards to kiss a line up Stolas’ torso as slowly the prince started easing down. Stolas was beginning to doubt he’d be able to take Calus’ knot considering he was barely managing to take half of the Dracony’s girth when Calus gently lifted Stolas up before lowering him back down. Stolas allowed Calus to help him ride the Dracony’s cock slowly getting further impaled on it until he was seated just above Calus’ knot. Allowing Stolas to adjust Calus grabbed the bottle of lube, coating one of his hands in it then stroking his knot with it for later. A couple minutes later Stolas started moving slowly, his face relaxing with whimpering moans although his thighs started to tremble from holding himself. Calus stopped Stolas’ movements by sliding his hand under one of Stolas’ thighs while pushing up with his free hand into a full sitting position, gently maneuvering them till Stolas was laying on his back with Calus looming over him.

“Let’s do it this way now, it’ll be easier on you,” Calus explained.

“Alright,” Stolas agreed.

Gently Calus started thrusting at a slow pace allowing Stolas’ slick to lube his cock, easily sliding in and out of the prince with each lazy thrust. Gingerly Calus lifted Stolas’ legs over his shoulders allowing him to thrust a little deeper, Stolas releasing open mouthed moans as he clawed at the bedsheets beneath him. Slowly over time Calus picked up his pace, pressing deeply into Stolas to grind with deep grunting groans and a throaty growl as he started getting close. Calus pressed against Stolas till his knot popped inside making the prince wince with a yelp, groaning loudly at feeling far too full now while Calus continued to shallowly thrust till, he fell over the edge. Calus spilled hot cum into Stolas promptly sending the prince over as well releasing a moaning groan before falling slightly limp against the mattress as Calus braced himself on both hands to either side of Stolas’ torso, panting heavily through his orgasm. Stolas shuddered at the feeling of Calus’ knot slowly pumping hot cum into him, waves of pleasure washing over him from a satisfying orgasm as they both waited for Calus’ knot to recede.  

“Alright, I’ll need to give a hefty yank to pull out,” Calus warned once his knot had softened.

Stolas braced himself as Calus snapped his hips backwards promptly yanking his knot free, but he didn’t pull completely out just yet. Stolas bit down on his lower lip with a slightly pained moan however it didn’t last long as he relaxed after a bit allowing Calus to pull out fully, falling beside him onto the bed on his back.

“Will that tide you over till Blitz gets back?” Calus asked, breaking the silence after a little while.

“Yes…that should most definitely sate me till Blitz returns,” Stolas confirmed with a wide grin.

“Good, well, I’m going to go wash up then head to one of the guest bedrooms for the rest of the evening.” Calus announced pushing up off the bed to head for the master bathroom.

“Very well,” Stolas agreed.

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.