Quite the Tour (Patreon)

Oh, dang. Talk about a good looking woman! Now she's exactly the kind I'd love to try: a perfect MILF…

Jason shouldn't have been thinking such lustful thoughts, of course. Fantasizing about older female customers was most definitely not within his job description as college tour guide. Hitting on them… well, that was even further from it. But there was no denying the spiciness of his thoughts, nor the sweetly polite, almost condescending glances she was giving every time he happened to catch her eye…

"And over there is Hobson Hall, one of the oldest buildings on the original campus. Did you know it housed not one, not two, but three future senators?" He was doing his best to stick to the script, of course. Had to at least do the basics. But maybe he could edge closer toward that lady. She was there by herself, after all. Nancy, she'd said her name was. Lovely brown hair, cascading down past her shoulders. Amazing, low-cut top that put those generous bosom on display. And of course, a nice tight skirt that showed off an ass that was still way more shapely than it had any right to be.

Yeah, she was hot, he conceded, even as she happened to catch his eye once more and flash that smile. His stomach somersaulted – his jeans tightened – and as his pulse hammered, he cleared his throat and spoke, lowering his voice to a more intimate register. "Not, ahem, going too fast for you? I hope I'm not… boring you?"

Oh, the cock of that head! That searching glance, that friendly gesture, that intake of breath that set her lovely bosom rising before his eyes! "No, not at all," Nancy purred – or at least, that's how it sounded to Jason's smitten ears. "You're doing an amazing job, young man. And don't worry – I still know how to keep up with young folks like you…"

God, she was- flirting. Or was she? Jason wasn't sure anymore – but for the moment it didn't matter. All he needed to do was gulp and nod and somehow find his voice again: leading the tour on, trying his best to ignore the still ache between his legs and the shivers of delight that rippled through him whenever he felt Nancy's quietly amused gaze resting on him…

***

He had to be dreaming. This had to be a wet dream – a hormone-fueled fantasy. Any moment he'd wake up and find himself grinding into his mattress with a sticky wet stain in his boxers.

But… no. Even once he'd blinked repeatedly, Nancy was still standing there in the glow of the streetlight, gazing at him with that same amused expression she had worn that afternoon. Now it was late evening, and here she suddenly was, looking more luscious than ever. "Aww, Jason! I really can't thank you enough for that wonderful campus tour today," she was telling him, and with every syllable his heart hammered louder in his ears. "You were such a good guide, really. Though I did have a few more questions for you – if you have the time, that is. I really would hate to ruin your evening if you were headed somewhere…"

Headed? Somewhere? "Oh! Uh, no- no, not at all! I was, uh, just out for a, you know, a stroll," he stuttered, and before he could quite find the words for a more confident response she was beaming and stepping closer. "Wonderful! Now, I was actually thinking we'd have a far more enjoyable conversation back in my hotel room. I know it may seem a bit forward, though, so if you'd rather go find a coffee shop somewhere-"

"No, no, that's- that's fine!" he blurted, blushing despite himself even as she laughed softly and motioned him before her. "Well, then, it's settled! Come on, my amazing tour guide. Why don't you show me the way to the Madison Hotel, hmm?"

Madison- ooh, that fancy place? Yes, puh-lease! Gotta be a dream, gotta be a fucking dream-

A dream from which he didn't ever want to wake.

Once there – once she'd clicked through the lobby and invited him into the elevator and led the way into her tastefully decorated, luxurious suite – he was practically quivering. She most definitely had something on her mind. She wanted to frolic – wanted him – wanted a luscious, virile young guy to satisfy her. Was he about to- to-

"What makes you think you can flirt with an older woman, Jason?" The question came unexpectedly: almost harsh in its tone and wording. "Come on, no more playing around. You were quite forward this afternoon for a, what? 21-year old?" "Almost 22," he responded, his lips suddenly dry with anxiety. "I- uh- but… But you were flirting too-"

Nancy's smile deepened, and she stepped closer, towering over his five-foot five self with her own impressive and heel-augmented stature. "Oh, you really think I was flirting? You really are a dirty-minded young fellow if you think that was me flirting with you! Whatever makes you think that I would be interested in a young, inexperienced child like yourself, hmm?"

Child?! Now that was taking things a bit far! But still, she was so close, and the scent of her perfume was filling his nose and mind, and all he could do was stutter and blush up at her in uncomfortable surprise. "I- uh, well, I'm sorry-" And he meant it – kind of. He certainly didn't want to do anything that might jeopardize his chances with this sexy goddess…

"Then again…" she cocked her head, and now her finger was under his chin, tipping his blushing face up toward her own searching gaze. "Young or not, I suppose it wouldn't hurt to show you a few things. You know, after all…" and here she smiled mysteriously. "You were such a sweet tour guide for me today. I suppose it's only fair that I take a little tour of you as well, don't you think?"

Jason never was quite sure exactly how it had happened, those next steps. The blood was rushing in his ears, and he was nervously complying with the low orders she issued, and all the while feeling about to pass out – or vomit – from the excitement of what she was about to do with him. But before he knew it, he was standing before her in only his boxers, hands clasped in front to conceal his aching hard-on…

And as for Nancy? She was laughing, stepping forward once more, now wearing nothing but a dark green brassiere and matching, generously cut panties. She was no college student anymore, that was certain – but the straining fullness of her D-cups and the sexy smirk on her face more than compensated for the few stray wrinkles around her eyes. "Come here, you naughty boy," she smiled, and her fingers closed around his forearm and tugged his hands away from his crotch. "Let Miss Nancy see what you've been hiding down there!"

"I- uh-" "On the bed, honey. Now." He scrambled to obey, and even before his head sank into the depth of the feather pillow, her hands were running suggestively over the aroused bulge of his manhood. "Oh, my. Someone's super happy to be here! Now, let me take a closer look. I want to see what happens if I press here… and maybe rub a bit here…"

He was in heaven. Her musical laughter was rippling through the room, while his entire body was shaking in delight at her touch. She was pleasuring him, her fingers stroking and squeezing around his cock, pressing and clutching more deftly and expertly than any of his own masturbation had ever been. Every time he cracked open his eyes, there she was: bending over him, smiling with a glance so confident and sweetly condescending that he felt he might faint from pleasure.

"Oh, you like that, hmm? Maybe my sweet little tour guide wants a tiny bit more of this – or maybe this…"

And then, before he quite knew it, he was cumming: spurting uncontrollably into his boxers, convulsing under her touch. Stifled little moans of pleasure escaped his lips despite his best efforts, and as her soft giggles compounded with the sensation of his own warm, sticky mess trickling over his skin, he gulped and shuddered with shameful pleasure. He- he was cumming for this woman-

"Aww, you're such an adorable little thing, aren't you? Just a tiny bit of teasing, and you're already making a sticky mess in your pants! Whatever am I going to do with you now, hmm? I really can't have you making a mess of my sheets – and we're just getting started! After all, you still owe me as good a time as I've given you…"

No- god, this was so embarrassing! But she'd- she'd teased him- made him cum- it wasn't his fault-

The whimpering apologies on his lips died away as the almost inaudible rustle of thick fabric caught his ear. "Here, this will be better," Nancy calmly remarked, and before he could object she was stripping his cum-stained boxers from him. "Now lift up, dearie." Which he did: upon which he felt the strangely thick, cotton embrace of what had to be one of the room's beautifully soft and luxurious towels. Wait, what?!

"There, this should keep you in check," she smiled – and only then did he realize what she had done. Around his waist there now clung that thick towel, fastened tight and shaped for all the world like an infant's diaper. "See? Now you can make all your sweet, cummy little messes you want and it will all be safely contained!"

His cheeks flamed. His eyes squeezed shut in humiliation. But even so, he lay there, quivering and nodding shamefully as she laughed and planted a quick kiss on his forehead. "Now then, my sticky little tour guide! Why don't you stay there and let Miss Nancy show you something else? Somehow I think you're going to find it very enjoyable… and tasty…"

As Jason's eyes blinked open and caught sight of her panties slipping away, her laughter sounded out once more. "Oh, don't worry! I know you've probably never tasted a woman like this before, but don't worry, sweetie. I'll guide you every step of the way. Here, I'll make it easy for you! All you need to do is open up… and lick…"

And so he did. Not for the last time that unforgettable night.