An Evening to Remember (Patreon)

"So it's all pretty straightforward, really," he repeated, casting an admiring sidelong glance at the attractive brunette beside him as they gazed together into the darkened nursery. "Her bedtime's at nine-thirty, of course, so she's gonna need a bath and story before that. And of course, everything you need is in here: sleeper, socks, plenty of diapers…"

Mila smiled knowingly as she surveyed the sight before her. "Oh, of course, Jerry! Believe me, this isn't my first time taking care of a Little. You ought to know that as well as anyone. Wasn't it at last month's munch I was telling you about how I dealt with Aaron when he was being a little brat?"

To which Jerry only shrugged apologetically and flipped off the light as they turned to head back into the living room. "Yeah, I know, I know! It's just that- well, I've never left her alone as a Little before, and I want to… you know… make sure she's in good hands." He fumbled in his pockets absently for his keys. "You'll call me if anything comes up, right? Anything at all?"

Mila chuckled and shook her head in amusement. "Jerry, go on. You're only gone for an evening with your coworkers – not to freaking Mars! Willow's gonna be perfectly fine with me, I promise." She gestured toward her Little charge and gave him a confidential wink. "Look, I'll give her a wonderful evening – an evening she won't forget. Just a Little and her babysitter, chilling and enjoying their time together!"

Jerry sighed and nodded, then stepped past her and bent down to plant a kiss on the upturned face of the onesie-clad, pigtailed form squatting on the floor amid a heap of blocks. "Okay, you be good for Miss Mila tonight, okay? Daddy will be home before you know it!" The upturned, pacified face of his Little wife almost made him reconsider, as did her lisping assent. "Otay, Daddy," she responded, clearly immersed in the innocent delights of her Littlespace. "Wuv oo!"

"Love you too, baby," Jerry sighed, smiling despite himself. "Love you too."

And then he was out the door at last, slipping into the blue Toyota and easing out the driveway into the street. He had thirty minutes to get there – no problem, as long as the traffic on Route 38 wasn't backed up… Okay, good, he mused, his eyes flitting over the center navigation screen. Map was showing only a bit of traffic. Should be a piece of cake.

Yet even as he drove onward, Jerry's mind was still busy with thoughts of the two he'd left behind. Oh, yes. The whole concerned Daddy side of him was no act; he really was anxious about leaving Willow at home, and all just to go out on a company dinner night. But they'd talked it over rationally last week, and she'd urged him to go, and they'd finally struck a compromise: one in which he would go out as expected, and she would get to spend the evening with Mila, their kinky friend who had practically jumped at the chance to play Mommy…

Oh, yes. Playing Mommy. Jerry knew her well enough – had even played with her once before meeting Willow – and he knew full well that Mila would be down for pretty much anything kinky. And as he drove onward, in his mind were some very delightful images: images of him stepping through the door, and finding some imaginary fault with Mila's babysitting, and telling her in no uncertain terms that he would need to discipline her. Images of her stripping guiltily before him, of him bending her over his knee and spanking her quivering ass as Willow, mute and regressed in her babyish state, would stare with widening and longing eyes at her babysitter getting spanked so humiliatingly…

Dammit. Maybe he should have become an erotica writer instead.

***

The dinner was… well, it was what it was. The usual blend of bad jokes, and people trying to talk shop and outdo one another, and snarky comments that only hinted at the simmering interdepartmental feuds – and all crammed into a din-filled pub that left everyone virtually shouting to be heard. Not to mention that the food was heavy and far too salty, and the portions were twice the size any reasonable person could down. To top it off, Jerry was driving – which meant he couldn't even blunt the evening's trauma with a margarita.

Yeah. Fun stuff.

But it was the socially acceptable thing to do, he consoled himself amid the hubbub, and here he was, doing it. So just as soon as these clowns could settle how to split the bill seventeen different ways, he'd be on his way back home. Home to Willow… and to Mila, the babysitter who would very likely need him to set her straight…

Oh, he would, he mused as he stepped at last out into the comparative calm of the twilit street. Home he'd go, there to assume the air of a Daddy who must be obeyed, who would set that bratty babysitter straight for ignoring his precious baby girl…

And so, it is perhaps understandable that once he had at last slipped into the driveway and turned off the engine and strode firmly up to the door and turned the key in the lock and stepped in, that the sight that met his eyes was enough to send those keys dropping to the floor in shock.

There indeed knelt his sweet wife, on the very living room rug where he'd left her. But gone was her paci, and the blocks, and her pretty unicorn onesie. Around her neck there was now a pink leather collar, and in her mouth a matching bit gag, and she was drooling gently as she stared up at him in glee. "Thaa-eee!" she burbled from behind the gag, wriggling in inarticulate delight. "Thaa-eee've howme!"

"Yes, he is, isn't he?" came the response from the leather-clad figure standing imperiously beside her. "It's so good that he made it back!" Mila – for Mila it was, of course – chuckled knowingly at Jerry's shell-shocked expression. "Oh, what's the matter, honey? Don't mind us – we're just having a bit of fun! Little Willow wanted to play puppy instead of baby, you see. And of course, as a good babysitter I couldn't deny such a sweetheart…"

"You know," she went on, running the leather leash through her hands suggestively. "I bet my dear little puppy would love to have a friend. Wouldn't you, puppy? Oh, of course you would! So come on, now. Get those nasty clothes off. I'm sure I've got another collar in my bag that will fit you perfectly…"

***

And so it was that, half an hour later, any neighbor nosy enough to peer through the slits in their living room blinds would have seen a most unusual sight: Jerry and Willow, husband and wife, former Daddy and former Little, bending submissively on the rug wearing nothing but collars and matching gags. And they might have even heard, too, the voice of their leather-clad, strap-on-wielding former babysitter explaining exactly what they were about to do…

"My little girl puppy needs some training, doesn't she? Now go on, boy. Sit. Sit! Good boy. Stay. Yes, stay. You're going to stay right there and watch mistress train her puppy. Come on, good girl. Good puppy. Now hold still for mistress… hold still… Oh, yes. That's a good puppy! Isn't that nice? Doesn't it feel so nice when mistress trains you? I bet my other puppy will like it, too!"

At which Jerry, watching as Mila's strap-on slipped in and out of his wife's swollen pussy, could only whine and ponder with clenching ass just how quickly his plans for the evening had run amok. 'An evening she won't forget,' Mila had said. Well, he mused as Willow's moans became muted little gasps and grunts of delight, at this rate neither of them were going to forget it anytime soon.