#prompt: crossdressing; me: gender exploration? don't mind if I do

[nsfwordwitch]

Kinktober 2023 Day 24

Prompt: Crossdressing

Pairing: Gale x Halsin

1497 Words

🔞Adults Only Blog🔞

Gale checks his shave in the mirror, thinking it's as close as he can get, though something of a shadow remains. He applies the lightest touch of red to his cheeks, and more than his usual black around the eyes. Finally, he dabs some dusty pink to his lips. His hair he's unsure what to do with, but leaving it the same doesn't feel right, either. Eventually he decides to part it off-center, letting some of it fall across his face. That will do.

He makes sure the dress is on straight. It's not quite as revealing as the robes Weft had received from the Wavemother priestesses years ago, but he had had it in mind when he conceived of this evening. He walks out of his bedroom and calls out to Halsin in the kitchen.

"Are you ready, Halsin?"

"I am!"

"Alright, I'm going outside now."

Gale heads out his own front door and closes it behind him. He pauses for a moment, then knocks.

He hears Halsin hurrying to the door, and smiles at him when he opens it. "Miss Dekarios," Halsin says. "Thank you again for accepting my invitation. Please, come in."

"You have a lovely home," Gale remarks, looking around at his own possessions. "Dinner smells wonderful."

"Let me show you to the balcony, and I can serve us." Halsin gestures, and Gale follows his lead. Halsin pulls a chair out for him, and Gale accepts the gesture graciously. "Please, enjoy the view. I shall be right back."

Gale looks out at the familiar view of the harbor, the salt breeze on his skin. Halsin returns with two plates of food, pan fried fish and garlic potatoes. Gale smiles up at him as he sets his plate down, and Halsin smiles back. "May I pour you a glass of wine?" Halsin asks.

"Yes, thank you."

Halsin continues as he pours. "You look lovely this evening, by the way. That's quite a gown."

"Oh, you are too kind." Gale says. Halsin sits, and Gale looks at him, thoughtful. "You know, a lady might get a certain idea in her head when you invite her to dinner at your home."

Halsin chuckles. "A lady might have a very active imagination. I resolve to be a perfect gentleman."

"Hm," Gale says, picking up his glass. "Perhaps we need not strive for 'perfect'." Halsin smiles, and Gale feels a thrill to see a blush form on his cheeks.

They dine. Without entirely dropping the act, they make small talk about their respective projects, Halsin with the druids and Gale at the academy. Gale is full of questions tonight, letting Halsin steer the conversation.

"I hope you saved room for dessert," Halsin says, pouring Gale's third glass of wine.

"Naturally."

Halsin takes their plates and returns to the kitchen, while Gale sips the wine. A ship is passing through the harbor, and Gale watches it with a detached interest. Why does it feel like a gloom has dropped over the evening?

"A chocolate tart, from your favorite bakery," Halsin says. Gale smiles in genuine surprise. Halsin had kept the dessert a secret and Gale is glad he did. Halsin breaks a piece off of Gale's serving and holds out the fork, and Gale smiles before taking the bite.

"It's perfect."

"I am glad to hear it."

When the tart is finished, Halsin sighs and leans back in his seat.

"I would be happy to walk you home, whenever you are ready to go."

"No, that won't be necessary." Gale lays a hand on Halsin's and gazes out to sea. "I'd like to stay a while, if that's alright."

"Of course."

Gale feels Halsin's eyes, but opts not to make a comment.

"If I may be so bold, Miss Dekarios–"

"Please call me Gale. We've become familiar enough for that."

"Gale. You seem…not quite your usual talkative self tonight. Was the meal not to your liking?"

"Oh, no, it was delicious. You really know your way around a salmon. I suppose you're right, though. Perhaps I'm feeling a touch of nerves about being unaccompanied in a man's home?"

Halsin smiles, but it doesn't quite reach his eyes. "I hope that this evening was…what you were looking for?"

"It was most satisfactory." Gale pauses, and holds Halsin's gaze. "Thank you for all the trouble."

"It was no trouble at all. But, Gale. I wish to remind you of what I said when you first suggested this."

A mild dread creeps up Gale's spine.

"You do not need a special occasion to be a woman. We have friends who chose to change their lives in ways that defied their births. You could do that, too."

"I know that," Gale sighs. "But I'm not…I'm not like them."

"How so?"

"I'm not…I don't wish to change my body. My name doesn't cause me any grief. And I don't feel unhappy when people refer to me as a man. I simply…being a man is a lot of work, sometimes." Gale pauses. "Don't you think so, too?"

Halsin's hand squeezes Gale's. "No, my heart. Being a man is quite effortless for me."

"But…" Gale searches for the words. "But there's so much pressure. To do it right."

Halsin takes Gale's hand in both of his and leans forward, getting closer than he has all evening. "There is no wrong way to be a man. Or a woman, or anything else. Whoever you are, whatever form you wish to take, it is right. I just hope it makes you happy."

The blood in Gale's ears is nearly deafening. Easy for Halsin to say. He's exactly what a man should be, tall, strong, confident. Not like Gale. Gale, who has failed to keep a lover for long without constantly fighting for their approval. What kind of man fails at that?

Yet…Halsin has stayed, in his fashion. Halsin asks so little, even meeting Gale's disparate and somewhat demanding requests, and he makes no demands in return. Perhaps that's a kind of man he can be.

He squeezes Halsin's hand and smiles at him. "You've given me much to think about. From the bottom of my heart, thank you. As for tonight…" Gale bats his eyelashes and holds Halsin's gaze. "This lady would very much like to go to bed with you."

"Hm," Halsin says, a smile crossing his closed lips. "Would it be more gentlemanly to refuse, to preserve your virtue, or to grant my lady's request?"

"I think you should carry me to my bed and damn my virtue."

"My lady's requests will not go ungranted, then." He stands, then scoops Gale up in his arms. Gale gasps and grasps at Halsin's neck, and Halsin carries him to his own bed.

He drops Gale on the bed and kisses him, hands traveling down his body. Gale sighs and abandons himself, letting Halsin's presence overwhelm him. Halsin's hands move to his back and start unbuttoning the dress, but Gale stops him.

"I would rather, I think, leave it on."

Halsin growls in surprise and pleasure, and moves his hands to hike up Gale's skirt. Gale squirms under his hands, and Halsin draws his underwear off slowly, making his erection spring back against him. Halsin spits onto his fingers and slips one of them into Gale's hole. Gale moans and rolls his hips, and Halsin takes the hint and adds another.

"Oh, Halsin," Gale sighs, "please, take me."

"As you wish," Halsin says, and he undoes his pants and pulls out his erection with one hand. He lifts Gale under the ass and swaps his fingers for his cock, and Gale throws his head back in pleasure.

"Yes," Gale breathes, "that's it, I–ah!" Halsin hits him deep, filling him totally. Gale wonders how he looks, now, his hair splayed around his head, his lip color smudged now, surely, his skirt tossed carelessly past his hips. He looks up at Halsin, still in his nice suit. Like they're stealing a moment in public, like they were so overcome with passion they could not wait for clothes to be removed.

Gale feels an orgasm rising, and he presses both hands to his cock. "Don't stop, Halsin, don't stop." Halsin grunts and grips his hips tighter, thrusting harder into him, shaking Gale's whole body. When Gale comes, it lands on the inside of his dress, and in his craze he thrills at the thought of the stain being hidden next time he goes out in public.

Halsin sees him come and moans. He presses hard against Gale, deep as he can, and comes with a cry. He eases out of Gale and sets him down, then collapses beside him.

Gale turns to him, and Halsin draws a thumb across his cheek. "You do look beautiful tonight, Gale. If it would bring you joy, I hope you dress up more often."

"I'm glad you think so," Gale says, smiling. "But truthfully? It's far too much work."