"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.
