"So, um, look," Emily said, biting her lower lip anxiously as she struggled to find a way to push past the pause and get to some difficult admission Chris could only imagine. "Before we go any further, you should know that, um, I... I mean, I'm not saying I've never been with a guy before, because I have, but I'm not exactly what you'd call, well... you know. Experienced. In the bedroom. I know you're probably used to girls who are into all kinds of kinky stuff, and I mean, that's fine, but I, uhh, I'm kind of vanilla, you know?"

Chris very much didn't. He'd connected with Emily on a website called KinkLife, after all, which had as its highly unsubtle slogan, 'The Kinky Hangout Where Kinky People Share Their Kinks'! And in addition to several beautiful photos of the lithe, winsome blonde exposing pretty much her entire alabaster body to the camera, there was also a list of fetishes on her personal page including but not limited to 'wax play, pet play, anal sex, anal toys, sex toys, massaging vibrators, bondage, fisting, flogging, caning, intoxication, exhibitionism, public nudity, facials, public facials, double penetration, triple penetration, two cocks in one hole,' and something called 'katoptronophilia' that Chris actually had to go and look up.

All of which made him a little confused to see Emily looking at him with her wide blue eyes, staring at him earnestly with a vulnerability that somehow managed to make him feel protective and horny at the same time, as she slipped out of her thigh high skirt that had been giving him and everyone else in the restaurant little winking glimpses of her shaved pussy all night and said, "I hope I'm not disappointing you. It's just that I have limits, you know? Some people are into some really weird and freaky shit--not that I'm judging or anything, I'm sure it's all fine between consenting adults, but I just couldn't do the things they're into. Do you think we could maybe, um, stick to the stuff I'm already okay with for our first time together? Maybe once we hit it off, I'll get a little more adventurous next time."

Chris opened his mouth. For a long moment, no sound came out. Finally, just as Emily took a buttplug out of her purse and began to spit-lube it, he managed to make himself ask, "Like what?"

Emily's eyes went distant with silent contemplation, even as she worked the squat sex toy in and out of her mouth like she was giving it the world's most enthusiastic blowjob. For a moment Chris wondered if she was doing a bit of some kind, but her expression seemed so sincere and the contrite, embarrassed tone in her voice so genuine that he couldn't quite bring himself to believe she was kidding even though it was the most logical explanation for what was happening right now. "I suppose, um, I could suck your dick?" she said at last, popping the buttplug out of her mouth and slipping it almost effortlessly into her anus. "I know that's kind of boring, but, um, I'm kind of a boring girl."

She took off her shirt and casually pulled a pair of nipple clips out of her purse, clamping them down onto her stiff nips with a wincing hiss of masochistic pleasure. "I know, you're probably used to someone a little more adventurous," she added, reaching out and tugging Chris's pants down around his ankles before practically tackling him onto the bed. "But I swear, I can make you feel just as good as any of those kinky chicks you're into if you just give me a chance. Like, um, you know, maybe I could--"

Her words broke off into a muffled groan of submissive delight as Emily knelt down between Chris's legs and spread his asscheeks, diving in and rimming his anus with her tongue. "Unnfff, unnnhh, uhhh, mmmm," she mumbled, as though she somehow expected him to make out what she was saying with her mouth absolutely plastered to his asshole, slurping enthusiastically away while her hands reached out and began to caress his cock and balls until they tingled with hot, urgent pleasure. Christ could feel the precum beginning to dribble out as she worked her fingers up and down the shaft in a practiced caduceus motion.

"And I mean, um, if a rimjob is too vanilla for you," Emily continued, lifting her mouth from his asshole and rubbing her face along the length of his stiff prick, "maybe I could, y'know...." Emily's lips engulfed Chris's shaft, swallowing all nine inches in a single smooth gulp to effortlessly deep throat him without so much as a single splutter. Emily was right, Chris was very experienced in the scene and had been with many women who were similarly free-wheeling and sexually adventurous, but he'd be hard pressed to think of a single one whose throat so casually accommodated his entire length. The cognitive clash practically locked up every single gear in his brain, and what was happening to his cock right now didn't exactly help him think.

Emily didn't come up for air for almost two full minutes, and when she did it was with a nervous, slightly expectant look on her face like she was an anxious puppy who'd just done her first trick and needed to hear that she was a good girl. "Did, um, did you like that?" she asked, punctuating her sentence with a long, flickering lick back and forth across Chris's frenulum. "Only, I mean, I know deep-throating is pretty vanilla these days, and I guess I was just thinking a guy like you was pretty used to it by now. It's boring, right? It's okay, you can tell me."

Chris opened his mouth, but just then Emily did another long, plunging dive onto his prick that left him gasping for air as his eyes crossed and uncrossed with an urgent lust that left him struggling not to simply shoot his load straight down her throat before their evening had really started. All he managed was a series of choked, strangled yelps of ecstasy as his hands clutched the sheets and he focused his entire mind on holding back his climax. Emily didn't even seem to notice. Her whole attention seemed to be centered on swallowing his dick.

She slid back off gasping for air, but otherwise seemingly entirely untroubled by her marathon fellatio session. "If, uh, if this isn't doing anything for you, um, hang on, I...." She reached back into her capacious purse and pulled out a pair of padded cuffs. "They're only velcro, I know, and a guy like you is probably used to something more.... uh, y'know, adventurous, but if you'd like we could--" Emily gave the cuffs a practiced tug to open them up, then rewrapped them around her wrists before putting her hands behind her back. She turned around to offer up the clasp for him to lock them together.

"A lot of guys like that sloppy, hands-free kind of blowjob," she murmured, casually manipulating the clasp with her thumbs and snapping it together while Chris stared at her in stunned bewilderment. She turned back around and began to lick and nuzzle his balls, smearing drool and precum all over her face in a lewd and messy display of phallic devotion. "I know you're probably into harder shit, but, um, I... I kn'w wh' li', ykn'w?" Emily's speech became slurred and incoherent as her attention focused ever more fully on worshiping his hard shaft and heavy, aching testicles. Chris felt like he was about to practically shower her with jizz.

"Mmm, gllk, mmm, glllk, if, uh, if you... sssssllllp, sllppp, sllllp... if you want something kinkier, slllppppp... w-we can take the plug out and you can fuck me up the ass... I mean, mmm, y-you can have my pussy too, f-fuck me bareback, but, glllmmm, glllllm, a guy like you gets bored by that, right? I... mmmm, I want to try for you, w-want to be a good girl and... mmmmmmmmm...." Emily deep-throated him again, her mouth once more fully engulfing the entire length of his shaft, and Chris would have laughed if the whole thing hadn't been so utterly bizarre. He'd barely even gotten a word in edgewise, and she was already offering anal sex as a compromise?

But she sounded so desperately sincere the whole time. She didn't act like she was kidding. Emily legitimately sounded like bondage and hands-free blowjobs and buttplugs and nipple clamps were all vanilla by her standards, and Chris couldn't help but wonder... exactly what were her limits, then? And who else did she play with to make her think that she was still somehow the vanilla one in the group after all this? Chris didn't know, but judging by the way his cock throbbed he was eager to find out.

She pulled off of him again, leaving him almost desperate to cum, and rubbed her face all over his cock like she was luxuriating in the feel of it against her pale cheeks. "Muh, muh, maybe you juss' wanna watch for a little while?" she mumbled, sounding almost drunk on lust as she wriggled against him and Chris heard the nipple clips jangling slightly with each swaying motion of Emily's body. "I, uhh, I got a remote control toy in my bag, you... you could shove it in my pussy and, um, and tease me until I beg you to let me cum. I know you probably got bored with that, uh, years ago, but, uhhh...." Her gaze went distant, as though the effort of thought was getting to be too much for her. Perhaps it was.

"Oh!" she exclaimed, finally resurfacing from whatever erotic reverie she'd drifted into. "You could get out my vape pen, um, and maybe use the vibe to get me so needy that you, uhh, you could make me take a hit every time I want to cum? And, like, then just keep telling me I'm not stoned enough yet, and trick me into vaping more and more until I'm half-asleep and then you could fuck my pussy like that? That's not too kinky. I could do that for you." Chris's eyes widened in shock. He'd never even thought about doing that with someone, it brushed right up against the limits of even risk-aware consensual kink, and Emily was once again suggesting it as a concession to some imaginary fetish of his.

And she kept right on going. "Or, um, do, do you maybe wanna hypnotize me?" she asked, her eyes wide and meek and glassy as she nuzzled his cock. "I, uh, I'm real easy to drop, you, you could even tell me to hypnotize myself and I'd just stare at my own finger until I tranced out to it. And I... I'm so suggestible, sir. You could do anything you wanted to my mind. Give me triggers, mess with my memories, make me, ummm, make me think that every kinky thing I'm into is so dull and boring that I have to keep offering you more and more and more until I'm acting like the most depraved slut imaginable and I still think it's not enough to please you. I... ohhh, fuck...."

Emily dove back onto his cock, sucking and slurping as though it was the only way to relieve the erotic tension building inside her befuddled brain. When she rose back up, her eyes were glazed and heavy-lidded, almost not even really seeing Chris anymore, and even though he had only the barest understanding of hypnokink he knew she'd willed herself most of the way into trance already. "I--you--did you do that already, or was that... ummm....?" Her brow furrowed in vacant perplexity, but Chris was finally beginning to understand. He knew now exactly what Emily was into. And it was even hotter than the kinks she listed on her website.

He settled her onto the floor in front of the bedroom mirror, pushing the vibrator he found in her purse inside her sloppy wet cunt and turning it up to full. There was also a suction-cup dildo in the bag, and Chris sealed that onto the silvered surface before removing Emily's buttplug and sliding his cock into her accommodating ass. "Is this--is this kinky enough yet?" Emily asked, her tone meek and simpering, and Chris playfully shook his head as he guided her lips onto the silicone shaft and began to fuck her in earnest. It didn't take her long to milk the cum out of him. But it also didn't take her long to get him hard again, either.

THE END