i don’t. know if i’ll ever go anywhere else with this so. posting it here as a ficlet because i need it out somewhere so it doesn’t rot in my drafts. concept of jim’s outfit heavily inspired by this sabrina carpenter look
roughly 900 words of joel dressing jim up and feminizing him under the cut
When Joel presents him with the panties, he foolishly thinks that’s going to be it. They’ve done the whole… feminizing bit once or twice, and Jim was honest when he said he liked it. He maybe just wasn’t honest about how much he liked it. (“Too much” is the answer. Too much that he’s willing to risk Joel turning it into something to make fun of him for.) Regardless, it’s not surprising that Joel’s going for it again. Joel’s always liked pretty and dainty. Doesn’t matter that Jim’s got some height on him, or that he’s fairly athletic. As long as he can manhandle him as he likes (and God, can he) he doesn’t seem to mind that Jim’s not exactly what he wants.
So after Joel’s diligently run a razor up and down his legs (not letting Jim lift a finger to help) and then proceeded to rub lotion into them until Jimmy was almost painfully hard and then fingered him open with the single-minded intensity of the fucking sun—
Jim doesn’t even have the brain power to think about the soft lacy cotton being slid up his bare legs, only enough mind to whine about the light pressure on his straining cock.
“Why are you dressing me?” He gasps out. “Seems— hah, seems counter-productive.”
“Don’t worry, sweetheart,” Joel soothes him, running a hand up his smoothly shaven calf in a way that makes Jim’s muscles jump. “I promise you’re going to like this. Don’t worry your pretty little head about it.”
And— okay. That’s nice, admittedly. Jimmy can do that.
He lets Joel pull him up to a seated position on the edge of the bed, only keeping himself upright through sheer force of will really. The sheets feel nice on his skin. He didn’t know shaved skin could feel so nice. Maybe he’ll do this again on his own time.
“Arms up,” Joel instructs, and Jimmy follows with barely a thought. He’s so hazy on everything that he doesn’t realize something’s being slid over his head until it’s blocking his vision, and it takes a second after it fully settles on his torso to realize what exactly it is.
“Is this—“ he swallows down a strange wash of emotion, fingers immediately playing with the little satin bow on the neckline. “Is this a nightie?”
“It’s cute, right?” Joel asks. He might be looking for an answer, Jim can’t tell, but in the moment he’s too stunned to give one.
It is cute. It’s made of poofy tulle and lace and ribbons, and it has to have been ordered custom for him because it hits right at the top of his thighs. It’s so thick it obscures everything underneath, not even a hint of skin peeks through the fine mesh. It’s baby blue, and ridiculously soft, and Jimmy feels like he’s too dirty to wear it even though Joel started this whole thing by running Jimmy a rather lovely floral-scented bath.
“I knew this color would look nice on you,” Joel keeps going, casual, like Jimmy’s not hanging on his every word while he tries not to move. “I had to guess on the length, but Lizzie is a genius with these things. It shows off your pretty legs so well — you know you’ve got legs for days, love. I liked the bust part too, not too tight so it’s not trying to highlight the tits you don’t have.”
That tears a whimper out of Jim’s throat. He bites his lip, finding his eyes suddenly humiliatingly wet. He tries to hide his shame, but Joel tuts at him and a warm palm on his chin guides his pathetic little pouty face up. He expects a reprimand, or the sting of a tease, and instead he gets something much worse.
“Oh darling,” Joel purrs, “don’t cry, I love your small tits. They fit you so perfectly, and they look so good in your little nightie. You’re so pretty, you know that?”
“Pretty?” Jimmy can’t help the broken whisper that crackles out of his throat as a stray tear slides down his cheek. It’s quickly thumbed away by Joel’s attentive hands, and the sensation makes his insides shiver. Interestingly, he’s not any less hard than he was when the panties went on. If anything, it might be worse now.
“So pretty.” There’s a softness in Joel’s voice, like coaxing a frightened animal. It makes Jim feel small and fragile, makes him press his thighs together and tug at the short hem of the dress. “So, so pretty all dolled up for me. Precious, simply darling.”
Jimmy whimpers again, chest heaving under lace and tulle as he fidgets with the soft material in his hands. His lashes flutter, gaze darting down to see Joel straining at the front of his trousers. Something about it — about seeing the evidence of Joel’s arousal from him, from seeing him in a frilly little dress — it’s so much. It’s good, but it’s so much.
His line of sight is broken by Joel reaching down to palm himself, massaging in a way that makes him hum and makes saliva pool in Jimmy’s mouth.
“Do you want me to show you how pretty I think you are?” Joel asks, voice pitched low and suggestive. “You want me to fuck you in your cute little dress?”
Jimmy swallows thickly, feeling his throat bob with the motion. “Yeah—“ he gasps, “yes, please.”
“Good girl,” Joel says, and Jimmy’s brain whites out.
