The Date (Tumblr Original)

She was a hell of a catch, that’s for sure. Tall, blonde, with stunning curves in all the right places and a voice that could make a stone weep, Renée had more sex appeal in her little fingernail than most women dreamed of. Not in my wildest fantasies had I ever imagined such a woman would be remotely interested in a guy like me - I mean, I don’t really consider myself that svelte or jaw-droppingly handsome. But what could I say? After increasingly flirty exchanges on Tinder, we’d agreed to meet up at the local Starbucks - and good God, I was not ready for how amazing she was. After only an hour of low conversation and electrifying touches under the table, things were already getting decidedly steamy… and so, heart thumping, I’d eagerly agreed to meet her at her place next Friday night.

Oh, I was excited. It had been three months since my last romantic relationship had ended on the rocks, and, well, getting off to porn just isn’t quite the same as a real, warm, sensual human being, is it? I was so goddam ready to get into her panties, and given how into me she seemed to be, it actually seemed like a real possibility. I had a couple of condoms on me just in case, tucked neatly away in my jacket pocket. No sense in being caught without them, you know…

Renée met me at the door in one of the most low-cut and provocative little black dresses I’d ever seen. “Welcome to my humble abode,” she breathed, leaning forward to kiss me on the cheek. “Why don’t you come in and sit yourself down? Make yourself…comfortable?” No second invitation needed, of course - when you’re given that sort of nerve-tingling welcome, a guy would simply be an idiot to not comply.

We had an amazing supper - though God knows I would never have expected her to be the cooking type. Maybe she ordered it in or something, I dunno. It was incredible, as was the wine that flowed copiously, and the scotch afterwards. Oh, I was flying high; Renée was laughing warmly, those beautiful eyes of hers shining in the soft light, her incredible curves straining to be free from the confines of that sexy black dress… We ended up on the leather sofa first, and it wasn’t long before she’d playfully pushed me down and leaned over me, eyes sparking seductively. “Why don’t we move this somewhere more comfortable?” she whispered in my ear. “Somewhere we can, you know, spread out…”

It was kind of a blur after that, to be honest. I remember fumbling with my trousers - the alcohol hadn’t been kind to my coordination - and her helping me out of them, then leading me assertively to the bed, where all kinds of miraculous sensations began to unfold. I remember her dress slipping easily to the ground beside the bed, those gorgeous breasts slipping free from their restraints… I remember her leaning down, pressing me against the heavenly-soft pillows, grinding provocatively on my erection while she lowered her full, tantalizing breasts toward my face. “Hush now and relax,” she commanded in that low, magically silky voice of hers. “I’m going to ride you now, big boy, ride you like a pony. Why don’t you show me just how well you can please me?”

Oh, I remember trying. It was incredible, the feeling of slipping easily inside her, of her bearing down on me, of seeing her grinding and bouncing as she smiled sexily down at me, of hearing her heave an occasional deep sigh of womanly pleasure. Maybe it was the alcohol. Maybe it was those three damned months of loneliness. Whatever it was, I came hard and fast…before she’d even begun to moan… “Sorry,” I managed to slur out, some second later, feeling the post-orgasm drowsiness creeping up on me as my dick faltered limply down, thoroughly spent. “Iss jus, you so dam sexy…” And then I must have drifted off, with Renée still smiling strangely down at me… Maybe I dreamed it - or maybe not. But as I drifted off, I seem to recall hearing her purring quietly in my ear: Sleep tight, little guy. You have no idea what’s about to happen, do you?

***

I woke - disoriented, cold, and strangely uncomfortable. What the actual hell? Why were my hands stretched up over my head? And my legs spread out like this? A few experimental tugs later, and it was clear even to my alcohol-fogged brain: I was apparently cuffed, bound spread-eagle on the bed, seemingly naked except for…what? I was wearing something odd, something thick and soft and puffy… Yet before I could fully grasp my situation, a shadow fell across my face. It was Renée - and, oh my God. She was stark naked, with a sly smile on her face and a gleam in her eye.

“Hey, baby,” she purred, running her cool fingers along my sensitive, naked torso. “Looks like you can’t handle your liquor all that well, can you? Or your women, for that matter…” She laughed softly and leaned closer. “I’m afraid you’ve failed my little test, baby. You see, I like my men strong and capable; I need a man who can actually make me cum at least once before he finishes himself. It’s surely not too much to ask… But honey, you just couldn’t manage, could you? I was barely getting started, and there you were losing it not five minutes in, like some hormone-crazed teenage virgin! By rights I ought to kick you out of here for such a shameful performance. And yet…” and here her smile deepened. “Because I rather like you, I’m not going to immediately send you packing. No… I’m going to give you a second chance to be my boyfriend.” My heart leapt. What? Really?

She tossed back her golden hair, her bare skin gleaming seductively in the lamplight. “You may have noticed you’re wearing a diaper, baby. Yes, that’s right. A diaper! Why, you might be wondering? Well, because I want you to! I think it’s the only appropriate kind of underwear for a guy who can’t even make a woman cum without spurting everywhere, don’t you think? Besides, I actually like the idea of having a little diapered baby boyfriend around the place sometimes… And so, that’s the chance I’m giving you, sweetie…” She grinned, and I now felt her hands beginning to persuasively stroke my dick through what I now knew, to my horror, really was a diaper - my diaper. “You like me, right? You think I’m sexy? You probably want to see me naked like this a whole lot more, don’t you?” Well, what could I do but nod? It was the honest truth, after all…

She laughed softly. “Of course you do, baby. Of course you do. So here are your choices. First option, you leave now and head out that door, never to see me again. You’ll be lonely, but who knows? Maybe you’ll find some mediocre, pimply, bucktoothed gal out there who will have you, who will put up with such an equally mediocre guy… Or, you stay here. You stay here with me all weekend, and come over whenever I want you to from now on, and I’ll train you to be my own little baby boyfriend. Oh, you won’t get to fuck me, not a chance. You blew that opportunity earlier tonight, baby…” As her soft, derisive laughter rang out I felt my cheeks reddening in embarrassment, aflame with the humiliation of having been so clearly inadequate…

But she wasn’t done. “But listen, baby! You will get to go out with me sometimes. We’ll let all your friends see you with such a gorgeous woman. They’ll be so envious of you, so admiring, so jealous of you and your sexy girlfriend. They’ll be thinking such envious and dirty thoughts, wondering how amazing it must be for you to have sex with such a goddess… But of course they won’t know the half of it, baby; they won’t know that here at my place, you’re not even allowed to think of touching me with your dick. They probably won’t even be able to tell that under your clothes you’ll be wearing a nice thick diaper - the diaper that I put on you, the diaper that I make you wear every single day and every single night…” She cocked her head to one side in amusement at the expression of growing horror on my face. “Aww, why so upset, baby? You’ll also get to have me take care of you! I’ll feed you, and tease you, and play with you in such lovely, naughty ways. I’ll cuddle you and change your diapers, and I’ll even let you suck on these lovely big boobies, just like I know you want to right now. You won’t be making love to me exactly as you want, of course, but you’ll be pleasing me, honey, pleasing me so very much… And isn’t that what we both want?”

She grinned and climbed atop me, grinding her bare pussy slowly, deliberately against the front of my diaper - inside which, to my horror, my dick was already stiffening and straining to be free. “And who knows?” she whispered now, her hands caressing her beautiful breasts right before my widening eyes. “If you do well for me, if you actually manage to bring me a few orgasms with that drooly little tongue of yours, who knows? I might even let you cum…inside your diapers, of course. I’ll grind on you just like this, and I’ll watch as my little baby boy whines and moans and eventually makes a cummy, sticky mess in his diapers for me, just like a dirty little baby boyfriend should. Who knows? After enough times, you might end up liking it so much you won’t be able to cum any other way…”

Oh. My. God. I tugged at my restraints, opened my mouth to speak, closed it, squirmed in humiliation as the full weight of my predicament bore down on me. I wanted to escape so badly…and yet somehow, I didn’t. This was nothing like I’d ever experienced before - and I had no idea what to do. She was so strong, domineering, bold…so beautiful, too. Before her I felt so helpless, tied up like this, quailing at the idea of letting this gorgeous, confident woman force me to act like…like a literal baby… I shivered as the diaper crinkled under me, reminding me of what my life would be like if I accepted her offer. She wanted me to pee myself, pee my pants, and maybe even…? No, I couldn’t, not really. I had my own life to lead. There was more to life than sex. I had more dignity and self-respect, after all…

And yet, there she was - so beautiful, so nude, so alluring, with that incomparable smile on her face as she watched me intently, all the while never giving my aching dick a moment’s peace with her seductive stroking. I would never again find a woman like her, not in a thousand years. Wouldn’t it be better to give in, to let Renée make me her “baby” or whatever, than to say a cold goodbye and never experience such beauty again? And after all, she did say she was going to cuddle me, let me touch her, let my lips touch her breasts and her most intimate places… Oh, God. I wanted it. I wanted it and hated it, and hated myself for wanting it so badly…

But in the end, after what seemed like hours but must have only been a minute or two, I knew my answer. I knew I would probably regret it, but I wouldn’t be able to bear it if I answered any other way than this…

I nodded.

And oh, even just the glorious smile that lit up her face was worth it. So incredibly worth it.