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There was nothing out of the ordinary in Flynn rushing up to Judy, panic in his big blue eyes and sweat in his stupidly-gelled hairline, and bleating at her, "Can I ask you something?" But perhaps, that day, Judy was tiring of the ordinary.
"Is it whether I'll sleep with you, Doctor?" she replied bluntly. A devilish sense of satisfaction filled her at his reaction. Turned out it was possible for him to look even more stressed.
"What? N-no!" he stammered, eyes darting about in search of assistance, or perhaps in fear of witnesses.
"Oh. Don't you want to sleep with me, Doctor?" she asked, in the same matter-of-fact tone.
"I - well - of course I do!" he blurted out, his self-preservation instincts as compellingly poor as ever. "But not like that!"
"Not like that?" Judy said innocently. "Not like what, Doctor?"
It was almost too easy. Flynn's cheeks had turned scarlet, and he was fiddling with his precious stethoscope hard enough to break it if he wasn't careful. "Not... not in an actually-doing-anything-about-it kind of way," he admitted weakly.
"That's a shame," Judy tutted. "Because I do quite want to sleep with you."
Flynn's big scared eyes got even bigger, and even more scared. "You do?!"
"Well, yes, Doctor," she replied, in the closest manner she ever got to kindly. "On one condition."
"What is it? I'll do it. I mean... I'll consider it. I mean... oh, Judy, I'll do anything! For you, Judy," he added hastily, "anything for you..."
Silly little desperate boy. Oh, how she could mould him. "I only want to sleep with you," she said firmly, "if I can go on top."
Flynn's eyes lit up, and he nodded so forcefully his fringe almost broke free from its prison of product. "Of course!" he exclaimed. "That would be fine! That would be... great, actually!"
Judy smiled. "Come to the nurses' flat after your shift?"
"Yes!" Flynn beamed. "Oh, yes, Judy, I will! I absolutely will!"
Judy kissed the tip of her finger, then pressed it to his mindlessly flapping lips. He quieted instantly, his soft mouth slack and warm beneath her touch. He was melting already, poor little thing. What a pleasure it would be to have him under her.
"So what were you going to ask me, Doctor?" she said abruptly.
He frowned. Then an urgent beeping sound started up in the direction he'd come flapping over from, followed by a clamour of voices.
"Oh, shit," he wailed, and dashed back into the ward, leaving her finger still raised in the air, hot from his breath.
Now, there, Judy reflected, was someone who could clearly do with some stress relief. Just a pity he'd gone to the very worst person for the job.
For the rest of his shift, Flynn could barely concentrate. There was nothing out of the ordinary in that, given his usual levels of anxiety and sleep deprivation. But what was out of the ordinary was the imagery filling his caffeine-addled head.
Judy, naked... well, that was quite an ordinary thought for him to be distracted by... but the idea that he was actually about to experience it, oh, good heavens... and specifically, Judy naked, on top of him, riding him... her beautiful breasts bouncing up and down as she worked herself on his so-long-denied erection... the view of her gorgeous body from below, her bearing down on him, everything on display as he lay back and enjoyed the show... and with the best possible kind of audience participation...!
He couldn't believe it - he couldn't wait - he couldn't shake the suspicion that this would end in some kind of prank, Terry leaping out of Judy's bedroom cupboard just as he'd got himself undressed - and frankly he couldn't bring himself to care. Just the merest hope that this was for real was worth risking all manner of humiliations. And why wouldn't it be? Was it really so strange to think she might find him sexually attractive? Maybe she'd always just assumed he wouldn't want to... accommodate her preference. People could be funny about that sort of thing, he knew. But not him! And certainly not when it came to Judy! Oh, sweet, sweet Judy... from her, he'd take anything.
And now here he was, finally, in her bedroom, both of them stripped to their underthings, her lace-clad curves already a sight he'd treasure for the rest of his days, and then, and then, there was what would come next...
...Judy smiled at him sweetly, turned and opened a drawer, and pulled out a tangle of straps, attached to a shockingly lifelike dildo.
"Well, Doctor," she purred, "would you like to help me get it on, or shall I do the honours?"
For a long moment, all Flynn could do was stare.
"Oh," she said sympathetically, "haven't you taken one this big before? Don't worry, we can go gently."
He hadn't even seen one that big before. Certainly not on himself. But that was far from his main concern.
One condition, she'd said. On top, she'd said. And now, horribly belatedly, he understood - correctly - what she'd meant. There were, he feared, only two ways this was likely to go, and one of them was in.
"I'm not gay!" he blurted out, practically on reflex at this point.
Judy looked at him strangely. "Am I a man, Doctor?"
"N-no..."
"Do I look like a man, Doctor?"
There it was, that familiar edge to her tone that warned him how close he was to a slap in the face. "No!" he replied hastily. "No, of course not!"
"Then there's nothing gay about this, is there, Doctor?"
Flynn eyed the long, thick, veined, flesh-toned strap-on, and quivered. He was sure there was at least a bit that was gay about it. But he didn't dare say it.
"Unless... well. Oh, Doctor. Is that what you've been trying to tell me?"
Judy's eyes were, suddenly, alight with an adoration Flynn had never seen radiating from them before. He had no idea what she was talking about, but he would eagerly go along with whatever lie he might need to spin if it meant she kept looking at him like that.
"Oh, Doctor," she continued, sympathy suffusing her tone. "Oh, no wonder you're nervous. Well, I think you're very brave. Have you told anyone else?"
"Um... no?" Which, at least, was true.
"It's okay, I understand. I know lots of girls like you," she smiled.
For a minute, Flynn thought - with astonished elation - that she meant she knew that lots of girls liked him. When her true meaning hit, it was with the force of a defibrillator.
"It must be very confusing," she cooed. "But don't worry. It doesn't have to mean you're gay if you don't want it to. And it doesn't make me any less attracted to you."
The look on her face corroborated her words. In fact, if anything, she seemed even more attracted to him, her eyes flitting over his petite body and reddening face with a new hunger. Flynn ducked his head as it swirled with shame. He'd always been self-conscious about his small frame, his effeminate features, the long dark lashes and soft, full lips... and now, just his luck, the love of his life was getting more turned on imagining him as a girl than she ever had thinking of him as a man...!
"Please don't... tell anyone," he found himself saying, because apparently, he still hadn't found a depth he wouldn't stoop to if it meant the chance of sex with Judy.
"I won't, Doctor," she promised. "I know it must be hard for you. But perhaps I can make it a little easier." She cradled the dildo in one hand, and caressed it teasingly. "I can think of one thing that might help, for a start."
Flynn gulped. "Look, Judy, I'm really not sure - I mean, I've never - I've never..."
"Taken it in the pussy?" Judy finished for him, and he let out a small, strangled noise.
"I'm not sure I'm ready to start calling it that," he said weakly - again, quite truthfully.
"The back passage, then," she offered breezily.
"That implies the existence of a front passage," he squeaked.
"Never say never," she smiled. "Anyway, whatever we're calling it, it's meant to be very pleasurable."
"I could do it to you, then!" Flynn exclaimed hopefully.
"Oh, Doctor," Judy smirked, "surely you know from your training that that wouldn't work nearly as well. After all, you lucky thing, you've got something other girls haven't got."
"I'm very aware of that," Flynn whimpered. No matter the maelstrom his mind was going through, his body was still insistently focused on the presence of a beautiful, nearly-nude woman merely inches from it, and had been throughout the whole torturous conversation.
"I meant your p-spot, silly," Judy rolled her eyes. "After all, I wouldn't dream of asking you to get the... front end involved. I'm sure it's a painful matter."
"It's getting rather painful, yes," Flynn groaned. He'd take what he could get, but it was devastating to see 'what he could get' being narrowed down to such a small, well-defined point. Well, admittedly not that small. But certainly, in some respects, worryingly pointy.
"Look, why don't I get this on," Judy said, brandishing the strap-on, "and then maybe you'll feel less self-conscious?"
She didn't wait for an answer, climbing briskly into the harness - without even taking off her knickers, Flynn lamented - and tightening it with the same practised efficiency she displayed in her work. He stared at the resulting effect, the hefty pink dildo jutting proudly from her pubis, and a confused, uncomfortable warmth started to flare in his gut. He was still staring, frozen, when she stepped closer, pulled at the waistband of his boxers, and sent them dropping to his ankles.
"There we are," she said kindly. "All girls together."
Flynn blushed harder under her gaze, naked and vulnerable next to her lace-covered modesty and monster erection. He'd never before felt like he was failing to live up to both sets of gender standards at the same time.
"Come on, Doctor," she soothed, "just relax."
She moved closer still, her hand sliding round the back of his neck, and then finally, finally, they shared the kiss he'd always dreamed of... although never in those dreams had there been a stiff, girthy protuberance pressing insistently against his groin.
"Now, be a good girl for me," Judy smiled, gazing into his dazed eyes, "and get up onto the bed."
Flynn scrambled to obey, almost tripping over his forgotten boxers in his haste, trying not to think about why a good girl was something he was so eager to be for her - and then realising, as his backside touched the duvet, quite why she needed him to be up on the bed.
"How should I, um..." he faltered.
"Hmm," she replied. "I think doggy style will probably be best. You know, for a beginner."
Flynn nodded meekly, as his last faint hope of watching her bouncing beautifully above him finally drained away. In its place came another wave of apprehensive embarrassment as he slowly, tentatively clambered onto all fours, presenting the full expanse of his arse for her perusal.
"Oh," she breathed, from somewhere unsettlingly close to his anus, "aren't you pretty?"
Then - the sound of a cap being popped, and a faint, smooth squirt - and moments later, Judy, wonderful, gorgeous Judy, touching him intimately for the very first time, and it was to press a soft, wet finger somewhere even he had never pressed before...
"Ahhh!" he whined, feeling suddenly helpless, trembling, a puppet held up by the merest centimetre of her flesh pushing into his tense, panicked body.
"Come on, Doctor," Judy chided, swirling the lubed nub of her fingertip in minute circles against his clenched ring, "surely you've done this dozens of times!"
"Yes," Flynn gasped, "but never on the receiving end..."
"I told you," she said fondly, reaching up with her other hand to stroke the pert swell of his cheek, "just relax."
As if that was easy at the best of times - never mind in the mess of a situation he'd somehow got himself into! He wanted so desperately, despite everything, to please her - and yet his desperation was the very thing standing in his way.
"Be a good little girl for me," she purred, without warning, "and let me open up your pretty little hole."
A sudden, shameful stab of arousal welled up within him, punching its way out as a mortifying moan. He sagged, his body melting into limpness, doing its best - without his conscious mind's signoff - to do as it was told. And, sure enough, as Judy patiently worked her finger against what he had never previously thought of as his entrance, sliding slowly in and out, rubbing coaxingly around the rim, it started to loosen up - to open up, just as she'd wanted, just for her...
"Oh, there's a good girl," she praised breathily, pushing deeper inside him, squishy little sounds of lube punctuating her movements. "Oh, well done. What a gorgeous little pussy. We'll soon have it good and slick and gaping."
Flynn wailed, overcome with bewildered excitement at her words. Apparently, now, he was ready to start calling it that.
And slick and gaping it soon was, under her touch - an experience quite unlike anything he'd felt before - his usually drawstring-tight anus probed and stroked and stretched into slack, heady relaxation, its muscly walls slippery and wet with lube from the now multiple fingers Judy was able to thrust inside, ready and able and eager to accommodate anything she wanted to give it.
Yes... even that.
"Are you ready, Doctor?" Judy asked, pressing the firm, smooth, lubed-up tip of the strap-on against his soft, yielding ring.
"I hope so," Flynn mumbled - which, again, was completely true.
"You've been doing so well," Judy murmured, nestling her warm, strong thighs close to his. "My good, sweet girl. You can take it, I know you can. You want to take my big, hard cock in your pretty little pussy, don't you?"
"Oh-h-h God-d-d!" he howled as she slid her way inside, both from the burning stretch of the dildo filling him, and from the humiliatingly powerful effect of her praise. What the hell was wrong with him? Why was he getting so turned on at being called a girl - at the thought of Judy fucking his pussy?
And the most important question of all: who on earth cared, now that she'd finally eased all the way in, skewered him to the hilt on her enormous cock, and was, indeed, properly fucking him - his Judy, his wonderful Judy - fucking his sluttish, virginal pussy for real?
He was just getting used to the sensation, just on the verge of regaining rational thought and dissolving with shame once more at his perverted arousal, when the angle of Judy's thrusts changed ever so slightly, and hit a spot that practically made his brain melt out of his ears.
"Oh, Judy!" he screamed, writhing with the sensation, desperately twisting to try and line that little bundle of nerves up against her once again. "Oh, please! Just like that! God, please!"
"Beg me again, Doctor," Judy grinned, grinding relentlessly into him, her shaft missing his prostate on every stroke, deliberately keeping that particular source of pleasure just out of his reach. "Beg me like a good little girl."
"Oh, fuck," Flynn whimpered. "Please, God, Judy, I need you to f-fuck my pussy harder... please, make me take your huge, throbbing cock deeper... I'm desperate for it, Judy, I want it just like you did it just then, I want you to... pound my... c-clit...!"
He was certain the BMC would make him retake his anatomy module if they heard him - or simply laugh him out of the profession for being so pathetically needy - but as far as Judy was concerned, it seemed, he'd aced it. With a chuckle of delight, she shifted just a little inside him, and suddenly the rough ribs of her thick, veined strap were rasping against that deliciously sensitive spot in a rhythm so thrilling it was almost unbearable.
Now he was moaning wildly with every rock of Judy's pelvis, his arms sapped of the strength to support him, slowly collapsing face-down into the duvet. He pressed his scarlet cheek into the cool cotton, conscious of his degrading position, the gorgeous view he was missing, the frustrated leaking of his own neglected cock, and yet, somehow, unable to care about any of it. How could he? After all, he was getting his anal cherry popped so spectacularly, unable to believe how good it felt, to have a hard, thick length shoved inside him, firm thighs slamming against his own, strong fingers grasping his hips, keeping him just where they wanted him.
But naturally, even when he was half-senseless with pleasure, the other half was primed and ready for spiralling into anxiety. And God knew he had plenty to be anxious about. How on earth was he going to keep this up? He was finally having sex - after a fashion - with his perfect, beloved Judy, and it was - unexpectedly - incredible, and all signs pointed to her being extremely into it too... and all he had to do, if he ever wanted to do it again, was maintain the charade that he was secretly a girl.
He'd known it wasn't the best idea to get involved with one of his work colleagues. Turned out there were infinitely many more ways it might go wrong than he'd ever thought of, and they were all opening up before him as distinct possibilities...
It had started out as a joke, and become real.
As Judy gazed down at Flynn spread out before her - his smooth, lean back, the soft curves of his waist and hips, his slim arms sprawled limply by his sides - she reflected that this was definitely his more attractive side.
Oh, he was fun to fuck, for sure. And - as she'd known very well already - very fun to tease. Perhaps it was mean of her to have pretended she thought he was coming out. But really, he'd walked right into it. And if he had the merest hint of a spine, he wouldn't have been so pathetic as to go along with it.
Pathetic was part of his - for want of a better word - charm, of course. Just as it was with most of the needy, desperate, bug-eyed boys who seemed to keep throwing themselves at her, purely by virtue of her having two breasts to rub together. Putting them in their place was a piquant pleasure. But you could hardly expect her to respect them. To see them as equals. They certainly didn't see her as an equal, after all. A beauty to be admired, a goal to be attained, a goddess to be worshipped - but not a person.
And the more she'd indulged the fantasy of pretty little Flynn as a girl - the more she'd trained this entertaining new lens on his traits, both physical and character - the more she'd found herself thinking just how much... nicer it would be.
Perhaps she really was tiring of the ordinary.
Just then, Flynn came with a groan, all over her nice clean sheets, and she sighed. She was certainly tiring of the mess.
No sense letting a little thing like an epiphany get in the way of an eminently achievable orgasm. Judy redoubled her thrusting, relishing the pressure and friction of the strap-on against her, and the overstimulated way Flynn moaned and squirmed under her. She fondled his delicious little peach of an arse, imagined herself reaching lower, down to his chest, groping soft, plump handfuls of -
- there it was...!
She collapsed on top of him with another sigh, this time of deep, blissful satisfaction. He was whining a little, pressed into the wet patch with her cock still stiff and proud inside him, but he could wait, and let her enjoy the moment. He'd have a lot more to whine about in a minute, after all.
Eventually, she eased her way out, marvelling at the slick gape of his hole, how it could almost pass for what she'd been calling it, and propped herself up ready for some pillow talk. She believed in, as it were, lancing the boil.
"I enjoyed that a lot," she smiled.
"Me too," Flynn panted earnestly, dragging his red face up to gaze at her. "Oh, God, Judy, me too. I can't... can't even tell you."
"But, Doctor," she continued, gently stroking his sweaty cheek, "I have good news, and I have bad news."
He stared at her, his gormless face just as slack as his rear. "What's the good news?"
"I know you weren't really trying to tell me you're a girl."
"Oh?" He frowned, the cogs of the brain that had somehow got him through medical school visibly turning. "Oh!" he exclaimed, his expression brighter than she'd seen it in... well, ever, although it wasn't a high bar to clear. Then those twitchy little eyebrows started to furrow again. "So... what's the bad news?"
"Well, the thing is, Doctor," she replied airily, "I'm gay."