When She Wants Oral… (Patreon)

What the fuck had I just gotten myself into?

I could hear it all in my memory – that fateful, half-joking conversation with my girlfriend Bridget just last month. It had transpired after I’d given her shit for not going down on me like I’d asked. “Like, is it really that big a deal?” I’d griped, watching her shrug herself back into her nightgown. “I mean, don’t get me wrong – PIV with you is fun. But I don’t see what your big hangup with oral is, babe. Don’t you like to make your boyfriend happy?”

Oh, she’d bridled at that. “Speak for yourself, mister!” she’d pouted, glancing suggestively down between her legs. “I sure as hell don’t see you begging to eat me out. Why don’t we say that the day you show me you know how to please me like that, I agree to suck you off?”

I’d laughed and agreed, little thinking at the time that she’d ever take me seriously. I mean, sure – I didn’t exactly have real experience with eating pussy. But it couldn’t be that hard, right? I’d figure it out… if she really wanted me to. In the meantime, I’d have to put up with life without blowjobs. Not the most fun prospect, but hey! At least she was good to me in other ways.

Oh, if I’d only known what she was about to cook up for me!

I gulped nervously and tugged at my bonds now, hardly believing that I’d actually agreed to such nonsense. “Hey, Monica and I want you to come over to her place and hang out,” she’d said – and I’d come over like the idiotic sucker I am. And then I’d found that they’d been drinking. The two had tipsily herded me back to a spare room, and lo and behold, I’d found myself in a room that looked more like a set for that dumb Fifty Shades movie than a typical bedroom.

“Oh, quit squirming,” came the voice of my girlfriend from behind me, and I winced as I felt her palm descend on my bare, exposed ass with a crack. “Ouch!” I yelped, jolting forward on the weird horse-like contraption they’d strapped me into. “Let me out of this, Bridget! I swear, you’re acting crazy tonight. Whatever the hell you want, just tell me-“

“No can do, loser,” Monica slurred, and I craned my neck up from my prone position and found myself staring up at her unexpectedly and fully nude form. “Look. I hear from Bridget here that you need a bit of training in how to eat a girl out? Pathetic, really. But I’m a good friend, you know. I’m not gonna leave her stuck with some useless, prudish excuse of a guy. I-” and here she flashed a dangerous grin and sank down to stare me right in the eye. “I know exactly how to teach you the ropes, lover boy. And tonight, we’re gonna do just that.”

“Hey, what do I do now?” Bridget called, and I flinched again as I felt her hand closing around my still-flaccid and dangling penis. “Slip that thing on, of course!” Monica ordered, and I gasped as I felt what can only be described as a Fleshlight on steroids slipping over my prick. “It’s already on! Now get that pretty pussy of yours over here so we can kick things off. Come on, what’re you waiting for?”

And before I knew it, my girlfriend was before me, stepping easily out of her panties and flashing her closely trimmed lady bits for us all to see. “Now, then – pony on up, girl! Give him a taste of a real woman, why don’t ya?” I bit my lips anxiously, eyes wide, neck recoiling as she stepped closer and my vision filled with her most intimate regions. She was- on my god. She was pressing her pussy up- up against my-

“Open up, loser,” came Monica’s voice, and I did. “Now lick. Suck and lick, like you’re face-first in the most delicious ice cream you’ve ever had…” The pungent scent of my girlfriend's moistening sex was in my nose already, and as I cautiously extended my tongue, I tasted my first – but by no means last – bit of womanly juices.

And then it happened – the shudder and jolt around my cock that made me mumble and grunt into the pink folds before me. “Oh, yeah – bet you liked that, huh?” A ripple of female laughter erupted above me, and I tugged backward in confused panic at what was happening. “Hey, get back here!” Bridget ordered, and then she was pulling my head and face back into her crotch. “Quit whining and please me, honey. Never mind about that little sucker…”

As I reluctantly licked and sucked, I felt the device around my hardening cock purr and tighten once more, eliciting a gasp and grunt of unwilling pleasure from my muffled lips. “Oh, yeah, this is the best part,” I heard Monica chortle over the low sighs and moans of my girlfriend above me. “See, the better he does, the more I’m gonna give him on that pump. And if he actually manages to make either of us cum… well, I might decide to let him cum, too! Maybe. If I'm feeling generous…”

I quickly lost track of time, lying there on the bench with hands and ankles cuffed tight, my face buried in my girlfriend’s genitals, biting back self-conscious moans of disgusted pleasure as the device around my penis throbbed and pulsed as if in time with her low sighs. “Harder, baby. Deeper!” she’d order from time to time, and oh, I’d try. My face was already slick with saliva and pussy juices, I was panting from the exertion and my own growing urge to ejaculate… and yet Bridget seemed no closer to climax than when I’d begun.

“Damn, he really doesn’t do very much, does he?” came Monica’s cutting remark, as Bridget finally pulled back and left me, glistening-faced and panting in my bonds. “Maybe he’ll work harder if we give him another kind of encouragement, huh?” Before my widening eyes I saw her fondling a slim, elegantly curved strap-on: pulling the straps up around her hips…  tightening them down… coating the rubbery prick in a dripping coat of lube…

“No- please- I’ll try! I’m really tr-“ My protests were cut short as Bridget stepped forward again and tugged my face back into her still-wt pussy. “Shut up and eat me out, bud,” she ordered, and in her voice there was a note of command and lust that I had never heard before. “Maybe you really are a wimpy little pansy who likes taking it in his ass. It’s sure worth a try, don’t you think? Or don’t you want to make your girlfriend happy after all?”

I’d never felt anything like that strap-on: the way it slipped greasily between my ass cheeks, seeking my vulnerable asshole, slipping insistently inside, seemingly filling me more and more with every thrust from Monica’s swaying hips. She was purring and laughing the entire time, too: telling me what a good little sissy I was going to become, how sweet it was that Bridget had a dumb little sissy for a boyfriend, how if I’d only be a good boy and give Bridget one tiny little orgasm, then she’d think about making me cum like I’d never cum before…

But between the terrific discomfort in my ass, my horror at being manhandled in such fashion, and my mounting fatigue, even now I couldn’t seem to give Bridget what she wanted. I licked, I sucked, I stuck my tongue as deep inside her as I could and wiggled it around… and yet all I seemed to elicit was more sighs and orders to try harder. I myself was humiliatingly, embarrassingly hard – but every time I felt that I was on the verge of losing it, the teasing suction around my cock would relax, the motion of the strap-on inside me would subside, and I would moan in disappointment at being dragged unwillingly back from the brink of orgasm by these two sadistic women.

“Fuck! He really is pathetic, isn’t he?” came Monica’s voice at last, and I shuddered as I felt the strap-on slide out of my aching bum. “Good god – still can’t get you off even with all that! Girl, you really ought to find yourself someone better. Someone ripped… experienced… hung like a fucking bull…”

I shuddered as Bridget finally withdrew her mound from my mouth and face, but her voice was reassuring… at first. “Oh, I dunno. I really like him, actually. He’s just so sweet and cute and dumb… so perfect for training and ordering around…” At that Monica let out a barking laugh, and I yelped under another affectionate swat to my butt. “Aww, really? Well, girl – if that’s your type, then you do you! Though honestly, if that’s how he’s gonna be, I’m beginning to wonder if we wouldn’t be better off taking another tack. Hang on. I think I got something around here somewhere that'd be just right for a wimp like that…”

What was that strange crinkle behind me? What was the low laughter, and the whispering, and the murmur of feminine voices? What were these freaks about to do to me now? I hadn’t the faintest idea… and I only began to understand when the first cottony sensation brushed over my exposed genitals.

“Try this on for size, ya pathetic little sissy,” came Monica’s jeering voice, and I squirmed as the device around my penis slipped free and I felt a strange, cottony, rustling bulk being drawn up around my waist and ass. “If you’re too inexperienced to even know how to eat a girl out and make her cum… well, it only seems fair to keep your sorry little ass in a fucking diaper!”

Oh, I protested at that. “No! No, please- I- Let me go- I don’t wan-” But once again, Bridget was laughing and forcing my mouth back into her womanly – and now visibly aroused – pussy… and so I doggedly set to work. “Keep on trying, you sissy little diaper baby,” she chuckled, and I felt her hands tightening in my hair as I desperately sucked and licked the slick, pungent folds before me yet again. “God, this must be so embarrassing for you! All tied down, getting teased, and fucked in the ass, and then freaking diapered by your girlfriend and her friend! Ohhhh… Fuck, you really are- so- so pathetic…”

I was pathetic, too. For much as I hated to admit it, it seemed that whatever Monica was doing now to my humiliatingly diapered crotch – and it felt like she was pressing some sort of vibrator insistently against my imprisoned cock – it was most definitely sending me teetering back to the edge of climax.

I still don’t quite know what it was. Maybe I was finally getting better at my technique. Maybe I’d worked Bridget up to that point at last. Or maybe – and deep down I think this was the case – it was the sight and thought of her boyfriend being utterly degraded and humiliated that turned her on so.

Whatever the cause, it came at long last: the convulsive grip of her naked thighs around my head; the sighing moan that shuddered into a series of crying gasps of pleasure; the primal, animalistic thrusting of her spurting pussy into my slick and panting face. My girlfriend was finally cumming… and I – bound, naked, and diapered as I was – was the one responsible.

“Fuck yeah!” came Monica’s voice from behind me – and I let out a strangled, muffled moan of my own as I felt the vibrator kick into overdrive. Oh, my bejeezus-! I was being teased- forced into orgasm- teased and edged and finally, finally being driven into the most humiliating orgasm of my life. An orgasm, that is, that was nothing more than me spurting helplessly into the thick folds of a giant diaper at the behest of my girlfriend’s sadistic friend.

When I finally came out of it, panting with dripping face and shuddering body, I opened my eyes and found Bridget kneeling before me with an indescribable look on her lovely, flushed face. “Well done, buddy,” she smiled, and I gulped and stared back, sagging in my cuffs in wordless, broken exhaustion. “Now, I’m definitely not one to break a promise. Just like I said, I’ll be more than happy to suck you off later tonight…”

She paused and winked boldly into my tired eyes. “Or… maybe tomorrow. You see, I think we’d better give you some time to recover, hmm? And in the meantime, I’m going to see if Monica here can’t tell me a bit more about these diaper thingies. I’d never have thought it, but it seems you clearly have a weird liking for them, after all…” She chuckled wryly and ruffled my tousled hair. “Who knows? Maybe you'll end up liking them even better than a blowjob!”

Did I? Might I? I honestly had no idea, cloudy and confused as my brain now was. All I knew was that I had pleased Bridget… that Monica had forced me to cum in my pants… and that both of them seemed more than capable of finding new and frighteningly devious means of playing with me.

Who knew where it all might lead next?