Confidence Boosting (Rias/Gasper)

Heyyo, my awesome patrons. Decided to write this after rewatching some episodes of High School DxD. Is it a weird pairing, well yeah, but I usually tend to like the crack pairings sometimes. This was just a little warmup thing before I get to work on whatever wins the next vote. Looks like Sultry Saiyan Supremacy and Knights of the Lewd Republic are tied by the time I'm typing this up. Hopefully within the next two days someone becomes the deciding vote. If not, then I'll end up having to decide. If so, whatever I choose to write first, the "second place" fic I will write afterwards.

As for this DxD fic, eh, I kind of liked writing this. I'll probably continue this at another date. There's plenty of sexy DxD women to go around ;)

Anyhoo, I hope y'all enjoy!

Disclaimer: All characters who participate in lewd or sexual acts are above the age of consent.

Gasper hated being outside. He hated having to make conversation with people. Or feel the scalding rays of the sun beam on his pale skin. If he had to choose, he’d much rather stay holed up in his room, playing video games or reading his favorite novels. However, this was his paradise before Lady Rias came into the picture and decided to upend his entire introverted livelihood. Recently, the crimson-haired devil had taken upon herself to “boost his confidence” so to speak. Akeno had apparently come up with the idea, which made a lot of sense considering what Rias would end up doing with him behind closed doors.

Right now, the dhampir was curled up in his bed playing the newest Super Smash installment. “Come on, get him Zelda! Agh, wait wait, no transform! Erm-no dodge! I-AGH NO, NOT THE SMASH BALL!!! Ahhhhhhhhhhh!” He wailed, watching the Hylian princess fly up into the air and disappear. “That was my last life too…darn it.” Gasper’s pointy ears flopped despairingly. Suddenly the sound of his bedroom door unlocking was heard, and he quickly jumped under the covers before Rias could see him. ‘Maybe if I pretend that I’m asleep, then she’ll leave me alone.’

“Gasper, I know that you’re faking it. This is the fifth time you’ve tried this. Either get up or I’ll call Koneko to throw garlic at you.” Rias would of course never do such a thing, but Gasper didn’t need to know that. She giggled, seeing the small dhampir hurriedly toss the blankets away from him. Her smile grew larger as she watched his eyes widen to the size of saucers, knowing that it was due to her current outfit. At the moment, Rias was wearing a magenta-black lingerie duo, consisting of a frilly brassiere with floral-like designs along both the bra and panties. “You like?” she asked, turning around to wiggle her tush in the direction of the blushing vampire hybrid.

Gasper tried his best to cover his crotch, knowing that her seeing his erection would only escalate things further. But it failed spectacularly, noting the hint of glimmering lust sparkle within her eyes. His doors slammed shut, quickly being locked by the devil heiress. By now he knew that his fate was sealed, sighing bleakly, and went to work stripping off his clothes. That seemed to make Rias happy by the way she smiled at him, making his cock twitch. It wasn’t fully erect yet, so his penis simply hung there, waiting for Rias to touch him. The dhampir scooted to the edge of the bed, sitting patiently, while the crimson-haired beauty got to her knees in front of his penis.

“Mmmm, so adorable~.” Rias cooed, blowing softly on the dhampir’s small penis. “I love watching it grow. Can you make it big for me, Gasper?”

“…O-Okay.” Gasper nodded obediently. ‘The quicker this is over, the faster I can get back to playing video games. Hmm…maybe Rias will want to play too?’ He didn’t want to get his hopes too far up. Usually after his “confidence-boosting” session, the crimson-haired demoness needed to leave due to her packed schedule. Sometimes after sex, she’d stay and cuddle with him. That always felt nice. Zeroing in on Ria’s immaculate and gigantic rack, Gasper gulped nervously, his hands shaking in the air.

Rias couldn’t help but laugh at the young man’s clear captivation with her breasts. “Go ahead, you can touch them, Gasper. I give you permission.” She waited as the dhampir unsteadily moved his hands towards her bosom. Mewling, the scarlet devil shuddered as Gasper’s hands touched down, quickly digging underneath her bra to further grope her chest. “Mmmm~” She murmured, seeing the dhampir’s dick spasm, growing larger with each squeeze. ‘If I’d known that Gasper was hiding such a sizeable phallus…then I’d have thrown my Orc dildo out months ago.’ At first, when Akeno had first mentioned this type of perverted training for Gasper, Rias was against it. Knowing how terrified the vampire hybrid was of the outside world, she very much doubted that sex would help to conquer his fears.

“Confidence does wonder for the soul. Throw sex on top of that and there’s no doubt that Gasper will be able to escape his terror. Trust me, I read this in Succubus Weekly.”

Rias could still hear the cheery voice of her vice president ringing in her ears, remembering the lecherous smile that came with those words. ‘Something just tells me that she has a kink for vampires.’ Feeling a tad hypocritical at the moment as drool leaked out near the corner of her mouth, the Gremory heiress gave the dhampir her own perverted grin. “Ohhh, it’s so big, Gasper. Are you that horny for your president?”

Gasper didn’t know how to answer that, choosing instead to look away.

“There’s no need to be ashamed. I’ve seen tons of boys stare at me with those lusty eyes, wanting nothing more than to see me naked and fuck them until their balls ran dry.” Rias chuckled, seeing a bit of jealousy flare up in Gasper’s face. She pressed her lips against his tip, kissing it gently in a fit to appease him. “Not that I ever would, of course. Why on Earth would I ever want a wimpy human cock when I can have a big, thick vampire dick?” The crimson-haired devil felt Gasper shudder as she kiss his dick, lapping up every side of it with her tongue, drenching the shaft with her saliva. “That’s a good boy, Gasper. Get hard for me. Show me that your dick is the only one for me.”

“Don’t forget to give him plenty of dirty talk too! Let Gasper believe every word you speak, even if you don’t mean it.”

‘But I do, Akeno. I really, really do.’ Rias’s heart began to beat like crazy as she enveloped the dhampir cock with her mouth. The taste of precum gushed onto her tastebuds, driving her pussy wild and felt her juices leak out and drip down out of her panties. She heard Gasper squeal out her name, almost sounding feminine by how high-pitched his voice sounded. That almost made her laugh again, but pushed it down, focusing on deepthroating the dhampir dong. Rias didn’t stop, not until her nose touched his pelvis, swallowing every inch of his vampire cock. Caressing his thighs softly, the Gremory heiress had to hold him steady, feeling him tremble intently. She sighed through her nostrils, sensing that he was close to ejaculating already. ‘We really need to work on his premature ejaculation. *sigh* All in good time, I suppose.’

“Rias!!!!” Gasper grabbed both sides of Rias’s head, bunching her scarlet hair up with his hands, and came instantly. He squirmed within the crimson-haired devil’s grasp, finding it difficult not to buckle under the intense pressure of his own ejaculation. “Don’t stop…please…” The dhampir begged with a whisper, wanting nothing more than his cock to live forever inside of Rias’s mouth. Waiting until the Gremory heiress was finished gulping down his semen, he started counting to one hundred to kill time. It wasn’t until he made it to five-hundred and seventy-five till Rias finally stopped sucking him off. As soon as she was finished, Gasper collapsed onto his back, breathless. He whined despairingly once his red-haired master removed her lips from his dick.

Rias, gulping down the remaining cum stuck in her mouth, patted her chest and moved to remove the bra. Reaching around her back, she unhooked it and watched it fall down to her feet, allowing her flawless tits to jiggle forth. “There, that’s better.” She picked up the brassiere, smelling the faint mixture of her perfume and sweat, and handed it off to Gasper. “Go ahead, I know you want-” Rias didn’t even get to finish her sentence before the dhampir swiped the bra from her hand, stuffing both cups onto his face and loudly began inhaling her lewd scent. ‘…I’m beginning to think that Akeno and I are a bad influence on little Gasper.’ Shrugging her shoulders nonchalantly, she went to work jerking his flaccid penis to once again go another round.

This time, once it hardened, Rias stuffed his cock between her bouncy tits, covering every inch of Gasper’s dick with her boob-flesh. “Happy?” She looked up to see the dhampir’s cheeks flushed with blood, showing his embarrassment. Hesitatingly, he nodded and waited until she began to move. “Go ahead, Gasper. This time you can take control. Thrust to your hearts content.”

“R-Really?!”

‘He’s so cute when he gets excited. I’ll have to make sure I keep him safe from the other women in school. As his master, him and his cock belong to me…on loan occasionally to Akeno too.’ Rias giggled again, nodding.

Gasper wasted no time and went to town pumping his hips forward. “So soooooooooft…” He moaned euphorically, gripping the Gremory heiress’s breasts as he fucked them. While Akeno had Rias beat in breast size (not that he’d ever have the balls to admit such a thing), the crimson-haired devil’s rack still was amazing to feel sandwiched around his cock. “Rias, your boobs feel…r-really really good!” His eyes shut, body squirming as that embarrassing truth escaped from his lips. Feeling Rias’s heavy tits ripple with every thrust, Gasper already felt himself on the brink of ejaculation once more. “Rias…”

The crimson-haired devil sighed again, shaking her head. “Already?”

“S-Sorry…” Gasper hung his head low, knowing that he was disappointing his master with his lackluster stamina.

Ruffling the young vampire’s hair in an attempt to appease him, Rias smiled towards the dhampir. “Don’t worry. This is only the second week. Give it some time and I know you’ll start to improve.” She still could remember the first time herself and Gasper were naked alone. The poor dhampir ejaculated the second she removed her bra, revealing her breasts to him. “Go on, cum, Gasper. Then we can move on to actual sex.” Rias had to fight the drool from leaking out of her mouth as she said that.

Gasper shakily nodded, increasing the speed of his thrusts. It only took a few more moments before he finally came, spraying his semen all over Ria’s gorgeous face. Some of his cum managed to sprinkle on the top of her breasts as well, staining them with his white syrupy fluid. The Gremory heiress opened her mouth, managing to catch a few ropes of sperm with her tongue, and swallowed the load down her gullet with a hearty gulp. “Naughty Gasper. Just look at what you’ve done to your master’s body.” Her left eyelid was covered with semen which left only her right to peek open towards the mortified vampire hybrid. Before he could hastily apologize to her, Rias swiftly pushed the dhampir onto his back. All the while using her free hand to catch all the remaining semen on her face and bosom, sticking her semeny fingers into her mouth, and slurped up every drop.

The ribald sight made Gasper’s dick harden once more, throbbing painfully as his devilishly beautiful master crawled on top of him. Cowgirl, that was what Akeno had told him the position was called. Out of the few he’d tried with the two women; this was his favorite at the moment. It was rather nice to see Rias and Akeno bounce on top of him, their humongous breasts swinging in the air. Sometimes he’d find the courage to reach up and grab them, suckle them too if he was feeling really brave. As soon as he felt the familiar warm tightness of Rias’s vagina, her inner walls coiling around his shaft, Gasper gripped his hands firmly, trying his best not to cum too quickly this time.

“You’re so cute when you’re trying to hold back, Gasper.” Rias cooed, gyrating her hips on top of the small dhampir’s pelvis. Lowering her head near the vampire’s lips, she gently rubbed her mouth against his. She did it over and over, waiting for him to make the next move. She easily could have made the move to kiss him, but Rias wanted for Gasper to do it. This was how he’d gain more confidence. If not, then he’d forever remain a weak and cowardly bishop. ‘Come on, Gasper. Kiss me. Show me how much you want this.’ Her blue eyes looked deep into Gasper’s pink irises, patiently awaiting what he did next. Finally, after what felt like eons, the dhampir pressed his mouth against hers, kissing her fully. Rias waited a few moments before inserting her tongue into Gasper’s mouth, after of which she took complete control of their kiss, swapping saliva with her beloved bishop.

‘Nonononoooooooo! I’m going to cum! No, I have to hold on! Just a little while longer!’ Gasper inwardly pleaded with himself. Ashamed as he was to admit it, he loved sex. Specifically, he loved having sex with Rias. And Akeno too. Being able to be sexually active with the of the most beautiful women he’d ever seen (technically speaking since he never actually went outside to meet other people) was something he never thought possible. As his kiss with Rias deepened, becoming more and more aggressive and passionate, the dhampir hastily reached for his master’s boobs, clasping them with his petite palms. They felt like they weighed more than his entire body weight, fondling the tits awkwardly, while the nipples began to harden thanks to his gropes. His thumbs accidentally brushed over the erect nubs, eliciting a cute mewl from the crimson-haired devil, Gasper proceeded to tickle them again and again, wanting to hear more of Rias’s adorable moans.

“Mmmm~! Gasper!! Yessssss, keep touching my nipples! You’re making me so wet!” Rias confessed, licking the side of Gasper’s cheek animalistically. Squeezing the young vampire’s head with her hands, she looked deep into his eyes again, lust and desire burning inside of them. “You’re bringing out the devil inside of me, Gasper~. I’m so close…” She kissed him again, gnawing on his lower lip. “…Shall we cum together this time, sweetie?”

Gasper felt like his head was going to swivel off by how fast he was nodding. Another few more seconds of Rias’s bouncing and he was sure to cum. At least now he could be proud of being able to cum together with his master. “Riassssss! Riasssssssssssss!! You’re even tighter now! Eeeeeeeeeeee, I can’t hold it any longer!!!” His body spasmed from underneath the crimson-haired demoness, thrusting his hips upwards one final time as he ejaculated deep into her pussy. Gasper’s hands intertwined within Rias’s, feeling hers massage his softly with the gentle affection she always showed him. ‘Rias…I love you.’ Childishly, the dhampir thought this to himself, knowing that he’d never have the courage to actually confess his deepest love for his master. After all, this was all being done solely to build his confidence so that he wasn’t a detriment to her team. It wasn’t as if Rias genuinely had feelings for him. Same went for Akeno.

At least, that’s what his dilapidated self-confidence led him to believe.

Rias’s eyes rolled upwards as she felt Gasper’s semen flood her womb, filling it solely with his vampiric seed. Even after three ejaculations, the young dhampir still had plenty of semen to pack her pussy to the brim with his sperm. It was honestly fascinating how someone with such low confidence and lackluster stamina could contain a nearly limitless pool of cum. “Gasperrrrrr~” She murmured lowly, sounding almost like a feral growl. Layering the dhampir’s face with affectionate kisses, along with animalistic licks, the crimson-haired devil felt his penis soften again within her cunt. Pouting cutely, she looked down at the panting vampire hybrid, “Awww, are you tuckered out already?” She was honestly disappointed, wanting to go just a bit more. After this, it was Akeno’s turn for the next few days, which meant that she’d have to go without Gasper’s amazing cock.

“I’m sorry, Rias.” Gasper apologized, rubbing his hands against her supple, sweaty thighs. “I’m a little tired now. Maybe we can take a break?”

“Oh fine.” Rias sighed, still pouting. She still had at least another hour to kill before she had to meet up with Sona. A devilish smile perked up near the edges of her lips as she shifted upwards off Gasper’s crotch. Cooing softly at the abundant amount of cum oozing out of her cunt, the crimson-haired devil crawled backwards, getting on her knees until she was eye-to-cock with Gasper’s flaccid penis. “I suppose I can clean you up while you relax. How about that?” She saw his cock twitch lightly from her words, nearly smacking her nose. Taking a few whiffs of it, Rias felt her womanhood moisten from the raw stench of sex emanating from his semen-covered dick. Enveloping the soft penis inside her mouth, she began sucking away at it to clean up the remaining residue that was stuck to his vampiric phallus.

Gasper stifled a moan by biting his lips, watching as Rias sucked him off voraciously. Her pillowy breasts were touching his legs while her head bobbed between his thighs. ‘At this rate, I’ll be hard in no time.’ In the meantime though, the dhampir reached for his gamepad and started it up again. ‘Might as well get another game in before we have sex again.’