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To be completely honest, Kurt doesn’t particularly like it.
Of course he is all for experimentation, especially when it comes to fashion, but the feminine items in his wardrobe are mainly for collecting purposes; sometimes to be used as gifts, sometimes as inspiration, sometimes because he likes the idea of them in one way or another. Some of the more androgynous (according to him, at least) items have been added to his own ‘wearable’ category, but really, most of the dresses, skirts and blouses are just there.
He doesn’t expect Finn to understand.
When his almost-step-brother sees his wardrobe for the first time (Finn and Carole had come over for dinner) Finn raises his eyebrows but doesn’t say anything, clearing his throat uncomfortably.
Over time it changes.
Finn is ridiculously innocent. He doesn’t know how to phrase his desires, doesn’t really seem to know that they are desires. He just kind of suggests, one day when Kurt is in a frenzy over what to wear to school the next day, that Kurt should wear that black skirt from the back of the closet. Kurt tries to laugh it off, but Finn seems serious enough about it.
Because Kurt is a fool and would probably do anything Finn asks in that clueless, friendly tone of voice, he does wear that skirt to school. It’s more of a kilt, really, and Kurt feels better remembering Alexander McQueen’s own attempts to bring skirts into the male wardrobe but...he still can’t deny that it feels horribly awkward.
The jocks don’t throw him into the dumpsters nowadays, but they jeer at him in the hallways. People look at him both twice and thrice and a few girls give him thumbs up. A normal day, really, but he can’t help but smooth his hands over the fabric of the skirt self-consciously. None of his usual button-up shirts had really worked, so he had gone with a white blouse to perfect the ensemble. It makes him similarly uncomfortable. It is like his own skin doesn’t belong to him anymore.
Kurt can’t deny the tingling feeling in his gut, though, especially when Finn’s gaze lingers on him a bit longer than usual. It is an intense feeling that follows him through the day, even during the classes he doesn’t share with Finn.
He doesn’t like it, but he still kind of does.
Like that, Finn starts to talk him into wearing even girlier items. Sometimes to school; the most outrageous so far is a dark pink headband that had raised more eyebrows than usual and Kurt still feels himself flush at the memory.
There have also been instances of girls’ skinny jeans with false gemstones at the back pockets and tight low-cut T-shirts, all in bright colours that don’t really go along with Kurt’s personal style, but no one seems surprised to see him experimenting (which is as insulting as it is relieving).
In the privacy of Kurt’s basement, things go even further.
Finn definitely has a fetish, he thinks, smoothing out the skirt again. It’s a white, knee-length skirt with light-blue embroidery along the hem; a Nina Ricci vintage design (it would look amazing on Quinn) actually, not that Finn would know. It has been paired with another white blouse and blue headband; he’s barefoot and wearing only white boxer briefs underneath.
He’s wearing only one more thing.
A necklace, silver, in the shape of a heart. Finn had given it to him to wear for these occasions.
Kurt doesn’t have the heart to tell him he doesn’t really like any of it.
He shifts from one foot to the other, brushing his hands over his blouse, this time, to rid it of eventual wrinkles. There is an itch at the back of his neck, following his spine, reminding him of how wrong it feels. Like he’s an impostor of some kind, only not really. He feels a bit silly too, because he knows he doesn’t look like a girl, not really, and he doesn’t get what Finn finds so intriguing about all this.
Finn’s gaze, however. It’s burning hot, and makes that tickling in Kurt’s gut almost unbearable. Had he been alone in the room, he might have rubbed himself through the front of the skirt. Maybe even let his boxer briefs fall to the floor to get better access to his dick.
Now, Kurt merely shifts again, flushing. His hands settle by his sides. “So...what do you think?”
Finn is blushing as well. His jeans don’t cover his bulge, but at least he has learned not to try and speak; he only ever manages to sound like a fool.
Instead he steps closer and they kiss. There is that sweet hesitance at first that Kurt knows so well by now; it never fails to make him melt a little.
Their bodies start to rub against each other and Finn’s hand automatically finds its way to Kurt’s hip, then moving back to cup his ass. Kurt has to moan because his arousal gets some friction against Finn’s leg, at the same time as he is sort-of reminded of the skirt he is wearing and it is, well, a bit embarrassing. Not quite right.
Finn’s hand moves under his skirt while they kiss, pulling at Kurt’s underwear, ghosting over Kurt’s erection; Kurt holds his breath. After all this time, he still wonders if his male parts are going to scare Finn away eventually. Not this time. Instead, Finn moves his hand to press harder against Kurt’s ass, pushing him closer to Finn’s body.
They rub against each other. After a few moments—Kurt knows that Finn won’t last very long—Kurt unbuttons Finn’s jeans and pulls them down somewhat, enough so that he can slip his hand in to comfortably rub.
Finn comes within seconds with a strangled gasp, his eyes flickering behind his half-closed eyelids. It’s endearing in a way. Kurt’s hand and Finn’s underwear are stained and it takes Finn several moments of heavy breathing before he has recovered enough.
He shoots Kurt an embarrassed, crooked smile and starts to return the favour. His hand is big and warm as he takes Kurt’s erection and starts to stroke, a bit more carefully than Kurt does when he’s on his own, but the lack of own control is so enticing; frustrating in a wonderful way.
He relishes in Finn’s other arm, which Finn had raised to wrap around Kurt’s body to pull him closer to Finn, turning him around to press Kurt’s back against Finn’s chest. It is a secure position that Kurt can’t help but lean into. Part of him wants to be taller, leaner and more muscular, but another part of him loves how he fits against Finn’s body so nicely like this.
He sort of hates himself for it. It’s like he is losing his final shreds of pride. Disturbingly, his father’s face appears in his mind at the thought, forcing him to push away fears and personal disappointment. Kurt can just imagine how he looks right this instant, wearing feminine clothes and a headband, held close and taken care of by another boy. Not in any way the son his dad had dreamed of.
Then, Kurt is edging and Finn’s hand just keeps going until Kurt can’t stand it anymore. He comes, his entire body stiffening, bucking his hips forward into Finn’s hand while his back automatically presses back against Finn’s body.
A few seconds later Kurt can think again. Finn has removed his hand; Kurt thinks that his skirt is certainly stained on the inside now. He straightens, patting at the fabric. Yes. Wet stains. Ew. He steps away from Finn to investigate the damage, looking up only when Finn clears his throat.
“That was...nice,” Finn says. Kurt nods, and it is quiet for a moment.
Then, Kurt is surprised when Finn leans down for one final kiss, but opens his mouth automatically for Finn to explore. It’s all tender and sweet and damn it if Kurt doesn’t melt a little again.
When Finn straightens, they’re both smiling. Kurt pulls away to go change.
Kurt exits his walk-in wardrobe wearing jeans and a black-and-white shirt (casual since he’s home) to find Finn lying on his stomach on his bed, skimming through some magazine he’s found.
Finn looks up. “Hey.”
“Hey.” Kurt smiles a bit again. He hesitates only a little before sitting down on the bed, then leaning down on his stomach and elbows beside Finn, squirming a bit to get closer. He is glad when Finn doesn’t ask what he’s doing.
Instead, they settle into a comfortable silence.