You guys have definitely seen this pairing before, but here's my own take on it. After all, it basically writes itself!

This one contains yuri, bondage (slightly), and anal. Also involves strap-on use.

EDIT: Updated to account for the "nitpick" review.

Enjoy!

#10: Piltover's Finest – Caitlyn, Vi

A soft groan escaped Caitlyn's lips as her eyes fluttered slowly open. Consciousness was slowly returning to her as she tried to get a sense of her surroundings. The familiar sight of a grandfather clock told her she was back in her pad, but she couldn't remember what had happened to make her black out. The last thing she could remember was berating Vi, who had had way too much to drink at the night's fundraiser.

A tug on her right arm snapped her to awareness, and she turned abruptly to her right. Her arm had been bound by a set of handcuffs to the side of her bed. Alarmed, her gaze shot to her left, which found her arm in a similar state.

"W-What the hell? What's going on here?!" demanded Caitlyn.

"Looks like you're finally up, Cupcake," said Vi as she strode into Caitlyn's view.

"Vi, if this is some kind of joke, I do NOT find it funny! Now let me go, right now!"

"Not yet, Cait. Night's still young, and I want to make it last."

"By handcuffing me to the bed? What's that supposed to do?!"

"You really need me to spell it out for you, Cupcake? Fine, how's this for a clue?"

Caitlyn's eyes shot wide open as Vi lifted her hand, revealing that she was holding a rubber strap-on dildo and a small bottle of lube. Though immediately she knew what it was for, it took Caitlyn a few seconds to fully understand the gravity of Vi's intentions.

"W-Wait, Vi! W-What do you think you're doing?! I swear, you let me go right now or I'll–"

Vi stopped Caitlyn as she made a gesture for her to 'zip her lip', and then set about to putting on the strap-on cock. Fitting it around her pelvis, Vi gave the rubber instrument a small slap to test it, satisfied with its stability, before coating it with lube.

"Just zip it, Cait, and I'll make this worth your while."

Caitlyn's eyes widened with dread as Vi knelt down in front of her, lifting her skirt away to reveal she had already done away with the detective's panties. Desperate, Caitlyn tried to kick at Vi, but the enforcer grabbed a hold of Caitlyn's legs and propped them upward, unable to strike against her partner. Vi effortlessly positioned the strap-on at Caitlyn's exposed pussy.

The sheriff's eyes began to water as she begged, "P-Please, Vi! Don't do this! I– AAAAAAHHHHH!"

Vi laughed as she slammed the strap-on deep into Caitlyn with one powerful thrust. Caitlyn wailed in pain as she was penetrated, the strap-on striking the entrance to her womb immediately. A moment passed before Vi withdrew a short distance, looking down at her handiwork.

"Well, well, well. Didn't know you weren't a virgin, Cupcake. Who's the lucky bastard who got your first time?"

Caitlyn didn't answer, too ashamed and in pain. True, she wasn't a virgin, but she wasn't that experienced either with sex. She was always working too much to pursue a relationship.

Vi began thrusting back into Caitlyn, her movements powerful and uncaring of Caitlyn's distress. The sheriff could only scream and cry, hurt that her deputy would do such a thing to her. She hadn't even taken the time to prepare her for her entry, and even with the lube, being fucked raw by Vi was extremely painful.

"V-Vi– AAH! S-Stop it! You're hurting me! VIII! AAAHHHHHH!"

"Oh come on, Cupcake, you can't be THIS much of a lightweight! Put some back into it, girl!"

Caitlyn was in tears as she saw Vi shift her head up toward her. Then, to her surprise, she felt Vi's mouth engulf her own in a wet kiss, her tongue dancing with the sheriff's. Her breath tasted of vodka and candy, which disgusted Caitlyn, but she found she couldn't stop herself from returning the kiss.

Immediately Caitlyn was confused by her own actions. What was she doing?! Why was she kissing Vi back?! Was she ENJOYING this?!

Her train of thought was interrupted as she felt Vi's hands grab at her large breasts. The enforcer's fingers clenched down on Caitlyn's chest, squeezing her plump tits with utter abandon. Seconds later, Vi yanked down the front of Caitlyn's top, her breasts bouncing out of their restraint.

Breaking off the kiss, Vi said, "Jeez, Cupcake, how do you stand up straight with these things?"

Caitlyn's only response was to shriek again as Vi began groping away at her chest. She had slowed her pace below, but only somewhat, and the violation was still a painful one. But Caitlyn felt as if the pain were subsiding a bit, her insides tingling as Vi's strap-on moved inside of her and her fingers clasped over her melons. It almost felt… good.

Vi suddenly stopped with Caitlyn's chest as she reached over to the side, inching her fingers over to a nearby bottle on a bedside table. Vi opted to stay in Caitlyn's snatch as she barely was able to reach the bottle, pulling it over. Holding the bottle over Caitlyn's chest, Vi squeezed it, causing a brown syrup to drizzle out and coat Caitlyn's breasts. Caitlyn mewled in humiliation as her chest was coated; the smell of chocolate wafted into her nostrils.

Vi licked her lips as she tossed aside the bottle and said, "Mmm, chocolate-covered marshmallows. Haven't had those in a long time."

"W-What? EEK!"

Caitlyn squealed as Vi began licking her left breast, lapping up the chocolate syrup while coating her with saliva. Vi took special attention to Caitlyn's nipple, sucking on the nub and dancing her tongue in circles around it. It was maddening to Caitlyn; it felt so dirty, but also felt so good.

"Hey, wanna taste?" Vi asked, pushing Caitlyn's right breast up toward its owner's face.

"O-Ouch! Vi, s-stop that! Stop– MMPH!"

Caitlyn's protests were muffled as Vi shoved her right nipple to her mouth. Caitlyn immediately turned away from the gesture, trying not to suck her own tits out of shame.

Vi soon got the message, and released Caitlyn's mound, which bounced back into place. "Oh well, more for me."

With that, Vi's salivating moved to Caitlyn's right breast, slathering it in saliva while cleaning it of syrup. Caitlyn couldn't help it as she moaned and gasped; it felt too good. Vi clearly noticed this, making a muffled chuckle as she continued to suck on Caitlyn's teat.

Releasing her mouth's hold on Caitlyn, Vi focused once again on plowing her strap-on into Caitlyn's snatch. Caitlyn's screams resumed as her body undulated in Vi's grasp, still ones of pain, but also now with some pleasure in her tone. Her breasts bounced in circles, prompting Vi to grasp them again and tug away at them while she fucked her partner.

"Ow! OW! V-Vi, n-not so hard! T-That really hurts! AGH! V-Vi, I said not so hard!"

"Hard's the only way I do it, Cupcake! Now come on, lemme hear ya say it! Say you want it!"

"AH! AAH! AAAHHH! V-VI! I-I'M– I'M GONNA– AAAAIIEEEEEE!"

Caitlyn shrieked as her body spasmed in orgasm. As her scream died down into a loud moan, Vi pulled herself back, taking a few deep breaths as she looked down at her exhausted partner. Caitlyn was gasping for breath as her vaginal fluids dripped from her core.

Pulling herself free of Caitlyn's insides, Vi reached into her breast pocket and pulled out a small key. Caitlyn did nothing as Vi unlocked her handcuffs, knowing the enforcer wasn't done yet. Tossing the key aside, Vi grabbed hold of Caitlyn's waist, making her yelp in surprise as she was hoisted up onto Vi's lap.

"V-Vi, wait a second! G-Give me a moment to rest!"

"Don't worry, Cupcake, I'm not doing the same thing twice."

For a moment, Caitlyn thought she was finished. But then, she suddenly felt the rubber dildo poking at her anus, and realized Vi's intent.

"Now it's time for this hole to get some attention!"

Caitlyn screamed at the top of her lungs as Vi thrust into her ass. She had never had anal before, and the entry was more painful than just about anything she had felt before, especially since Vi hadn't done anything to prepare her for it. Without ceremony, Vi began thrusting in and out of Caitlyn's rear, the sheriff making pain-filled cries as she was bounced up and down on Vi's lap.

"AAH! AAHN! V-VIIIII! S-Stop it! Y-You're g-gonna m-mess me up i-insiiiide! OHH!"

Vi could only laugh as she said, "Oh come on, Cupcake! It's not THAT bad!"

"N-No, V-Vi! It-It huuuuurts!"

"Jeez, you really suck at this, don't you? No wonder you're such a tight-ass… literally!" Vi chuckled at this pun, though Caitlyn did not acknowledge it.

As Caitlyn continued to bounce atop Vi's lap, the enforcer once again grabbed hold of her partner's mounds, giving them more hard squeezes. Seconds later, she turned Caitlyn's head toward hers, forcing another wet kiss. This time, however, Caitlyn found herself moaning loudly at the combination of sensations assaulting her body. Her mind began to blur as pleasure took the place of pain, and she found herself with one hand on Vi's, trying to guide her partner in her grips and gropes.

It wasn't soon afterward that Vi again began thrusting harder and faster into Caitlyn's ass, the sheriff's moans turning again to screams of ecstasy. Vi's hand moved from her partner's tits and down to her wet cunt, roughly fingering the entrance. Caitlyn again tried to guide Vi's hand, but could only accomplish so much between her breasts and her pussy.

Caitlyn soon screamed again in a wail, and once again shook in orgasm. Her fluids sprayed out of her pussy, coating both her own hand and Vi's. Vi released her hold on Caitlyn, letting the sheriff collapse forward onto the bed, gasping for breath.

Amid her deep breaths, Caitlyn said, "Th-That w-was… That was…"

"Something else, huh?" Vi interrupted. "Damn, you really are inexperienced. Don't worry, Cupcake. Night's not over yet. I'll give you a few minutes first."

Caitlyn groaned in dismay at this as Vi sat beside her, stretching her legs casually. Knowing Vi, she wasn't going to be finished anytime soon.

And to her own mortification, Caitlyn found herself thinking she didn't want Vi to stop.

Vi: "Damn, Cupcake, what's with these marshmallows?" XD

I kinda wish Vi would say that in-game, but oh wellz. I get to do it here.

Caitlyn being sexually inexperienced is believable in my eyes. Even though she's got Piltover's biggest rack, she's probably too busy to be having sex a lot. Vi, on the other hand... Well, I wouldn't put it past her, although I expect she's always on-top. ;)

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