Pretty Boy

It was the kind of day where the only thing worth doing was to stay indoors. It was storming something brutal, rattling the windows of the tiny apartment and threatening to blow Kit’s plants right off the fire escape. Kit came back in absolutely soaked after rescuing their plants, and stood dripping somewhat miserably as they looked over their cactuses. There was no way the poor things weren’t overwatered now.

Nothing for it, though. Kit shivered and sighed and grabbed their phone before trotting off to shower.

Half an album of Bowie, an orgasm, and most of the hot water later, Kit emerged towel-wrapped and feeling much better. The storm hadn’t let up. They watched it from the window for a while, nature’s sheer power, before it occurred to them they had no idea where their boyfriend was.

He must be in the house, they reasoned. A wicked idea came to them. With an elegant flick of their wrist they had shed the towel, tossing it across their shoulders, and were on the prowl. Kit themself might be sated, but something about masturbating always made them want to give head. They would find Clare and surprise him, and then they might have to take another shower, but they could drag Clare with them this time. It was a win-win.

Silently they picked their way through the apartment, easing open the few doors to the place and finding them empty. That of course left the bedroom, which Kit had already checked—but it was possible that he was in the absurdly large walk-in closet. Sometimes he liked to nap there.

There was yet again no one in the bedroom, but the closet door lay open. Quietly, Kit crept toward it.

Clare was in there, all right. But he was not asleep.

A mirror stood in the back of the closet, and past Clare, Kit could see themself. Moreover, so could Clare. Kit scarcely noticed their reflection, however. Their eyes were fixed on their boyfriend, and on the elegant, ill-fitting lingerie he wore: stockings and garters, and lacy orange panties. His hand was on his hip, fingering the silk fabric, but he tore it away after he realized Kit was there. He turned, and Kit realized they had never seen him look so genuinely frightened before. “Clare…?”

He did not answer, staring at them like a deer in the headlights and steadily flushing crimson. Kit tried again. “Clarence, what—”

They never finished their thought. Clare scrambled for the door handle and threw it shut.

Kit gaped a moment longer. Timidly, and without really thinking about it, they tried the handle. It turned—there was no lock—but he must have been leaning against it to keep it shut. From within Kit could hear shuffling, fabric being hurriedly pulled off of skin. “Sweetheart?” Kit called. “Please open the door?”

“N-no thanks.”

“What’s going on?”

“Nothing,” Clare said, sounding miserable. “Please go away?”

“No, I’m not going to go away. Are you okay?”

Silence. Then: “Well, I—I’m so embarrassed that I kinda want to die, but that’s all, I guess.”

“Okay, well. I’m glad that’s all it is. You can’t die of embarrassment, though. I’ve tried. Please let me in?”

“… You … if I do, you can’t laugh.”

The way he said this made Kit’s heart ache. “I would never.”

It seemed like nothing happened for a long time, after that. But finally the door did open. Clare had stripped down entirely, the stockings lying in a pool beneath him with the garters on top. The panties dangled from his hand. He looked small and fragile, and Kit could feel the mother hen instincts swelling up in them.

“Come here,” they said gently, stepping forward with arms outstretched. Clare seemed to hesitate—but he fell into it a moment later, burying his face in their shoulder. “There you go. I love you.”

Muffled: “Love you too.”

Carefully, Kit guided him to the bed. They sat him down, and sat down next to him, drawing the blanket over his lap. No one liked to be naked and ashamed, they reasoned. “Can we talk about it?” they asked.

Clarence looked as though he might chew a hole in his lip. His face was still brilliant red. “Dunno what there is to talk about. I mean, you … saw everything.”

“I did. I’d like to know what it means, though.”

“Just. I dunno. I … I like dressing up like that. In, um. Girl’s clothes.” He cleared his throat. “It … it feels good, I guess.” Kit nodded, waiting for him to continue. It took him a bit, but he did. “I dunno. It’s, shit, I’m sorry…”

“Sorry for what?”

“Aren’t … I mean. You, you’re … I’m not, not like you. That’s not why I wear it, I mean, so …” He swallowed. “It’s too weird.”

“You’re dating ‘too weird’,” Kit said firmly, wrapping their fingers around Clare’s. He still wouldn’t look at them, eyes glued to the floor. “I don’t care if you like dressing up like that.”

Clare mumbled something, and glanced at them. Kit raised an eyebrow. He groaned. “But it’s just—it’s different from you, ain’t it? I like being what I am. I don’t got, like, a persona or alter ego or whatever, I don’t want to be a girl.”

“I believe you,” Kit said. This did not seem to satisfy Clare: he remained abashed and red-faced. “Starlight, it’s okay. If it makes you feel good, who cares?”

“What about … don’t, don’t you care?” he asked nervously. “You like guys. You like masculine guys—”

“I love you,” Kit interrupted with a pointed look, and took him by the shoulder. “I love you and I love whatever makes you happy. What on earth gave you the idea that it would upset me, of all people?”

This time Clare did at least reach up and take their hand in his own, his fingers cold to the touch. “You just, I dunno. You hate girly clothes so much. Skirts and whatever. I thought you’d get mad, or you’d, you’d think I was making fun of you…”

The hapless, disbelieving laugh that escaped Kit cut him off. “Babe, no, never! Oh my gosh. I don’t like girly clothes on me. That’s all. And I know you would never make fun of me like that …”

“… still not normal,” Clare mumbled. “They don’t even make me look good. I-I dunno. I don’t—with my arm I just …”

Oh, their poor Clare. Kit looked him over, then got to their feet and crossed to the closet. They retrieved the lingerie, presented it to Clare, and said: “Put it back on for me?”

He gave them a doubting look. Kit tilted their head to one side, then knelt and tugged the blanket off his knees. Gently, they worked the undergarments back onto his hips and legs, and guided him to his feet before stepping back.

“Well,” they said, “honey, orange isn’t your color at all. And I think the stockings are too big … they’re sagging, there, see?” Kit knelt again, pulling the stocking back up his calf. “No one would look good like that. We can get you things that fit.”

“… Kit, no, you don’t gotta …”

“Gotta what?”

“You don’t have to try and make me feel better.”

“I’m telling the truth,” they said firmly. “You’re extremely hot to start with, and you’d look even better in things that fit you. Go ahead and get dressed. There has to be somewhere in town that sells nice underwear in your size.”


Mercifully, the storm had begun to let up by the time Kit finally coaxed Clare out of the house. Rain drummed on the umbrella, providing a much-welcomed buffer of noise as Clare haltingly detailed the depths of his crossdressing. “I’ve been doing it a long time,” he said as they made for the street with the railway station. “Since before we met, just off and on. Um, I think my sisters started it. They always liked dressing me up when I was little.”

“I think that’s cute.”

“If you’re five, I guess. Not when you’re twenty-something—”

“Clarence Vogel,” Kit said, “I forbid you from saying one more mean thing about yourself for liking something completely harmless.”

“Okay. Okay, boss,” Clare said sheepishly. “Uh. Well. I, I dunno. I like … feeling pretty, I guess. Handsome is okay, but …”

“Not the word that feels right?”

“Yeah. I like … I like putting the effort in. I’ve always liked the idea of makeup, I been watching some of those tutorial videos. I’ve got … maybe, haha, m-maybe if we’re already out we could—I dunno, get some eyeliner, or something—”

Without another word Kit veered the two of them around, backpedaling to the corner drug store they had just passed.

Kit knew very little about makeup. They did know about looking intimidating enough that no one gave them a second glance when Clarence was awkwardly trying to find a shade he liked, that would match his skin. That was something. And they took the eyeliner and let him scuttle outside with the umbrella, content to subject themself to the well-meaning cashier’s miss and this’ll look lovely on you. For Clare’s sake.

Next stop: Frisky Business, where Kit had once accidentally toppled an entire shelf of dildos and was now a recognized customer. They and the owner, Stacy, went and got lunch sometimes. Clare balked when they reached the storefront. “Sweetheart, I don’t know about this.”

“Well,” Kit said, stopping. Peering into the window, they could see the large bookshelves that blocked the rest of the store from the streetview. “I won’t make you do anything you don’t want, but … I dunno. I’d like to explore this with you. If anywhere won’t judge it’d be this place.”

Clarence looked at them then, hard and long and a little disbelieving. Kit smiled back, and leaned in to kiss him. He leaned into it, and Kit’s heart fluttered a little when he slipped his fingers through their hair as rain pattered over them. When they took him by the hand and led him into the store, he did not resist.


Clare’s least favorite employee had been the only one working: Rex, a thirty-something blond with a punk aesthetic. Kit was not exactly sure what his problem with Rex was, but they definitely felt him stiffen when he noticed. As the door chimed shut behind them Rex looked up, gave the pair of them a welcome smile and nod, and went back to focusing on whatever he was busying himself with at the counter.

Rex seemed like a perfectly nice guy, in Kit’s book.

“Wish it wasn’t him,” Clare mumbled to them once out of Rex’s earshot, as Kit was picking through racks of silk underwear. “Dunno how I’m gonna live that down.”

Kit exhaled, picking out one last pair and turning to him. “Okay. First lesson, love. It doesn’t hurt anyone. It doesn’t do anything but make you feel good. You don’t have to be ashamed of it.”

“But—”

“Look, I like it when you tie me to the bed and pull my hair and call me your slut.” Their eyes wandered over to the counter. “I’ve come in here and told them I need better cuffs because mine make me bruise when I’m wearing them for over an hour, and they just show me where the better ones are. I think that’s a little more damning than what kind of underwear makes you feel pretty.”

Clare gave them that that was true, eventually. Even so, he did not drag his feet much less. Eventually, Kit picked out one set: teal and shimmery, with white stripes, and matching thigh-highs. “And … oh, you’d look so good in this,” they murmured, pulling a strappy corset in the same fabric off the rack. “Oh, honey. Please try this on.”

They looked at Clare and found him staring, his face once again crimson. He wet his lips, glanced at them, and then with a steady and resigned kind of sigh took it from their hand. “Okay,” he said, “but you gotta get the dressing room key.”

Kit was happy to do this. They trotted off to the register and said hi to Rex, who was as always happy to see them. They got the key with a limited amount of small talk, and alluded that Clarence had lost a bet as a way of giving him an out, which was met with laughter. Something about this made them uneasy, but they could not pin down why. Despite this they made their way back to their boyfriend, key in hand, and ushered him into the lone dressing room.

Kit was allowed in just long enough to help start the corset’s zipper. Upon being kicked out they paced a bit outside, both eager and nervous. They went and looked at the collars, and then at the vibrators, trying to find patience and instead only finding silicone.

“Kit?” called a voice, and they looked back to find Clare sticking his head out of the doorway. He gestured to them to come over before disappearing back into the stall. Kit slipped in after.

They were not expecting what they got. Clare was stripped down to his boxers and the teal corset, standing before a mirror. This much they expected. They had not expected the sheepish grin on his face. “Well, whaddya think?”

“I told you it would look good on you,” Kit said admiringly. “What do you think?”

“I—it’s really nice. I like it a lot, just—it’s real spendy. And I don’t think I’d use it much?”

“Well, I’m buying all of this, so we’re getting it,” Kit said, wrapping their arms around him and giving him an approving once-over in the mirror. “You’re so pretty! You’re so pretty, babe.”

Clare was an absolutely vivid shade of pink, but he was beaming.


There was a little making out as Kit helped Clare out of the corset. Just a little, until he had his clothes back on. Clare seemed uncharacteristically flustered and speechless as the two of them headed to the register. Kit had made sure to have the clothes visibly in their own hand as they approached, and neatly laid them out on the counter to be checked out. “Nice,” Rex drawled as he ran the scanner over him—and then his gaze darted to Clarence. “Gonna be a sissy for the weekend, huh?”

Clare’s smile melted instantly. “Um … what?”

“Just always looked like Kit here oughta be wearin’ the pants,” Rex went on lightly. “Careful, I saw her bite a guy’s head off in here once over rope techniques—”

All of Clare’s joy had evaporated. Kit could feel it without so much as looking at him, but look they did: he was small again, more hunted-looking, with his eyes glued to the floor. The casual “her” was just insult to injury, when they knew Rex knew better. Rage billowed up in their chest like gasoline on a fire, and was met by a scrabbling cloud of anxiety. Together it seemed to glue their mouth shut. Finding their tongue was a fight—but seeing Clarence reduced to shame again got them through it. “Rex?” they started, barely aware of what they were going to say before they said it. “I don’t—I don’t think it’s any of your business why we’re buying those, and I don’t appreciate you calling my boyfriend names.” They swallowed. “And please don’t call me ‘her’.”

Rex looked up. Far from the cowed expression Kit would have liked to see he looked outright bored. “Sorry,” he said in a voice that suggested he was not sorry at all. “Just making conversation. Debit or credit?”

The rest of the exchange was something of a blur. Soon Kit found themself standing outside in the rain, which was pouring again, with their wallet clenched in one fist and the shopping bag in the other. Their pounding heart had lodged inconveniently in their throat. “I can’t believe,” they started, as Clare opened the umbrella, “I cannot believe—that asshole! Clare, I’m so sorry …”

“S’fine.”

“It is not fine. Stacy’s going to hear about it.”

“We got what we came for, can we just go home already?” Clare said, his voice laden with annoyance. Kit detected it instantly, and could not help but feel like it was directed at them. “I have a headache.”

“… Okay.”

They walked in silence until they reached the light rail station, where that silence gave way to more silence. The tram home was the same, and to Kit it felt like the pressure was simply building and building until they stepped into their apartment. They stood awkwardly in the hall as Clare kicked off his shoes and muttered something about ibuprofen and a nap.

“That could have gone better,” they whispered to themself, after the bedroom door clicked shut.


Kit had been a mechanic. Kit had great experience as a repairman. Kit knew all about fixing things.

Kit did not know about fixing Clare’s ego, though. It was normally enormous enough on its own, well aware of its own weight and able to stand by itself. This was the first time they had actually seen it truly bruise, they reflected over their tea a bit later. Poor Clare.

Well, they’d be damned if they let it topple now.


The bed was warm. Clare tended to take up as much space as possible when he had a mattress to himself, and that was the case now. Kit shivered a little as they slid in under the covers beside him. To their relief, he stirred. “Hey,” they murmured, getting in close enough to trace their hands down his sides from behind. “Sleep okay?”

“Mmgh,” Clare said, not rolling to face them, but shifting to hook his ankle back around theirs. “Not really.”

“That’s too bad.”

“Yeah.”

Kit pondered their next words, letting their legs be entangled and scooting forward enough to spoon him. It was becoming abundantly clear that they had no idea what to say, so … “Do you feel any better?”

Clare grunted, to which Kit bit their lip. “Well,” they said after a moment, “and I don’t want you to feel pressured, but I’m still excited to see you in everything. No rush.”

This was met with a sigh. Finally, Clare rolled over to face them. He looked exhausted. “I dunno,” he said as Kit drew his head against their neck. “I guess … nnm. I just … worry.”

“About what?”

“You … about you, I guess. I mean! I’m your dom, I’m the top—I know you aren’t into women …”

“You don’t stop being a man when you put different clothes on.”

“I know! I know that, I just—I don’t want you to look at me differently afterwards. I don’t want to ruin anything. I read about this stuff online and I see people like, ‘I thought it would be fine but now I want to break up.’ What—what if you change your mind?”

This last was scarcely audible. Clare had all but disappeared into Kit’s neck. Kit had taken to kneading circles into his back, biting back sighs. “You know I felt the same way the first time I asked you to dom me?”

“That isn’t …”

“It is so, hush up. I was scared out of my head. Here I was, big bad Kit, just about able to bench press you, and I wanted to be tied to the headboard and whipped. All so you could take care of me afterward. I was so sure you would think I was some sick bastard for it.” They curled their hands up to catch his hair. “I’m not going to think differently of you. I’m not going to start seeing you as something else. I just want to see you happy.”

Against them, Clare sighed. Kit’s nervousness ratcheted up again, or it did until Clare levered himself up on his arm and gave them a tired smile. “I’m being pretty stupid, huh?”

“Mmm … maybe a little,” Kit smiled back, and tugged on his ear.

“Nah. Stupid. Okay. Lemme shower. Then we’ll do a fashion show.”


The shower did something, alright. It must have been a cold shower, because Clare came out of it kicking. “Sweetheart, you wanna get me the tablet?” they heard him call through the door a second before it opened, and they were treated to the always-glorious sight of him naked. “I gotta put on my face.”

“You mean your eyeliner?”

“My face,” Clare repeated dramatically, and clapped the door shut again.

He opened it again, laughing, to get his tablet, and the bag with his lingerie. And then Kit was left fidgeting on the bed again, wondering why eyeliner took so long. Maybe he was doing something insane like those incredible winged looks they’d seen online.

Well, that was fine. Kit had other things they could do to help. By the time the bathroom door squeaked open again, Kit had cleaned up the messy bedroom, made the bed, and discreetly made sure the lube was in easy reach, just in case. They had changed into fresh clothes, too, putting on the pretty, strappy sundress they liked so much but didn’t dare wear in public. (This was somewhat ironic, they realized as they admired the way it settled on their hips, but no matter.) And just for good measure, they dabbed on their colonge. “Kit?” came Clare’s voice from the hall.

“Clare?”

“Uh … haha, okay, can you bring me the shoebox on the closet shelf? The white one?”

“The one with your prosthetic parts?”

“Yeah, um, except that was a lie.”

Kit quirked one eyebrow to themself as they fished the shoebox down. They couldn’t help it: they pulled the box off just as Clare added, “And you can’t look, you’ll see what’s in it in a second!”

Kit stayed put for a moment, considering the box’s contents. Gently, they put the lid back down, and wondered how long he’d saved up for it.


Clare got his box. Or rather, he made Kit put the box down outside the door and then leave. Anxiously—but a good sort of anxious, for once—Kit settled down on the edge of their bed and waited.

The clicking of soles on the faux-wooden floor of the hallway made them look up. Music drifted into the room, a snappy electro-swing with a crooning tenor. And then Clare, nothing but skin and shimmery teal fabric, and a pair of blood-red heels that put an extra two inches on him. He leaned on the doorframe, his damp hair carelessly hanging in his eyes but failing to obscure the amateur-but-ambitious job he’d done with apparently more makeup than Kit had been aware was in the house. It was a little clumsy, but it was damn good for a man with one arm.

And anyway, Kit had been right. They realized this as the grin spread over their face and their cheeks flushed pink without their permission. They did the only thing that seemed appropriate as Clare sidled into the room: they wolf-whistled.

“Yeah?” Clare said, grinning brilliantly and redder than Kit was. “Thanks for waiting.”

“Oh, honey, it was worth it. Turn around? Do a spin, do your little dance on the catwalk.”

Clare laughed and obliged, inexpertly making a stab at a few poses. It was clumsy and silly and Kit was taken fully off guard by just how incredibly attractive they found his joy. That, and what his corset did to his hips. “Fucking encore,” they said admiringly when he paused, getting up and crossing to him to put their hands on his waist. “I love the heels. But how am I supposed to kiss you when you’re all the way up there?”

He was still smiling, but the glint in his eye took a decidedly sharp edge. Before Kit knew it he had wrapped his hand up in the collar of their dress and forcefully walked them back to the bed, pushing until the backs of their knees hit the mattress and they toppled. “Like this,” he purred as he climbed on top of them. Kit’s surprised laughing was cut short as he pressed a hard kiss to their lips.

It was funny, Kit remarked to Clare some twenty minutes later, that the lingerie was so expensive and they hadn’t even tried to keep it clean. He was still in all of it, if you counted the fact his underwear was hanging off one leg. For Kit’s part, they were still decent. Mostly this was because the dress did a good job of hiding stains, and they hadn’t been wearing any underwear beneath it in the first place anyway.

Clare laughed, again, and it just made Kit happy. He had been all light and excitement for the act, showing off, a perfect peacock in his flashy clothes. Even now he was dripping sweat and seemed to have no intention of getting undressed, and something about this—well, it was certainly hot, but it was also just charming.

Sore and tired and light-hearted, Kit leaned heavy against his chest and found his eyes with theirs. “Pretty-boy,” they said fondly, pressing a finger against his lower lip. “Pretty, pretty boy that fucks like a train. Mine.”

“How does a train fuck, though?”

Kit considered this, then leaned over him to reach for the tablet that had wound up abandoned on the bedside table. “I don’t know,” they said, unlocking it and finding their way to the browser. “But I bet there’s some Thomas the Tank Engine fanfiction that can tell us.”

“I want a divorce.”

“You’ll have to marry me first,” Kit cackled.

Under them, Clare exaggerated a horrifed moan and covered his eyes with his arm. A moment later he had reached up to slide his hand through their hair, and tugged them down next to him. “Hey.”

“Hey.”

“Thank you. Really.” He paused. “D’you think Stacy will give us a discount on more panties if we tell her about Rex?”

“She’d better.”