Relationship With Crossdressing - Office Family, Matter - Chapter 3

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The revised dress code policy sat in Tommy’s inbox like a hard-won trophy, its bold, unambiguous language a stark contrast to the vague corporate-speak he’d grown used to. He read it again over his morning coffee, savoring the words: Employees are free to dress in alignment with their gender expression. No asterisks, no caveats. Just permission finally to exist as himself.

Rachel appeared at his desk with two coffees in hand, her grin sharp with victory. “To not having to burn the place down after all,” she said, clinking her cup against his.

Tommy laughed, but his eyes flicked toward Karen’s empty office. Her nameplate had been removed overnight, her desk cleared with an efficiency that felt more like an erasure than a transfer. “Think she’ll come back swinging?”

“Doubt it.” Rachel sipped her coffee. “Corporate doesn’t demote quietly unless they want the problem to disappear. She’s probably halfway to some middle-management purgatory by now.”

The thought should have been satisfying, but Tommy felt an odd twinge of guilt. Karen had been a nightmare, but she’d also been a product of the same rigid system he’d just forced to bend. He shook it off. Some battles didn’t leave room for sympathy.

Derek from Marketing cornered him near the break room, his usual swagger replaced by an awkward shuffle. “Hey, uh. Got a sec?”

Tommy braced himself. Derek had been avoiding him since the coffee machine incident, their fragile truce hanging by a thread. “What’s up?”

Derek shoved his hands into his pockets, staring at the floor. “I talked to my sibling. Like, really talked.” His voice dropped. “They said they’ve known since they were a kid. Just never told me because” He broke off, jaw tightening. “Because of shit I’ve said. About people like you.”

The admission hung between them, raw and unexpected. Tommy studied Derek’s face the guilt there was real, but so was the fear. Fear of losing someone he loved over something he didn’t understand.

“They’re coming to visit next weekend,” Derek continued. “I was wondering if… maybe you’d wanna meet them? You don’t have to. Just thought,”

“Yeah,” Tommy said, surprising himself. “Yeah, I’d like that.”

Derek exhaled, shoulders loosening. “Cool. Thanks, man.” He hesitated, then added, “For the record, that navy skirt you wore last week? Killer with the blazer.”

Tommy blinked. Derek’s smirk was back, but this time, it didn’t feel like a weapon.

Lisa listened quietly as Tommy recounted the conversation over dinner, her fork pushing peas around her plate in slow circles. “So Derek’s sibling is nonbinary,” she said finally.

“Yeah.” Tommy watched her face, searching for tension. “You okay with this?”

Lisa sighed. “I’m trying to be.” She set her fork down. “It’s just… a lot. First the office, now Emily’s school, and...”

A crash from upstairs cut her off. Emily’s voice, sharp with anger, followed by the thud of a slammed door.

Tommy was up the stairs in seconds. Emily’s bedroom door was locked, but he could hear her muffled crying through the wood. “Em? Open up.”

“Go away!”

He leaned his forehead against the door. “Not happening.”

A pause, then the click of the lock. Emily sat curled on her bed, her face blotchy, her phone screen lit with a TikTok video a clip of Tommy’s diversity assembly, spliced with mocking captions and laugh-track audio. The comments were worse.

Who let this freak near kids?

Bet his daughter wishes she had a real dad.

Tommy’s stomach twisted. He sat beside her, careful not to touch. “Who showed you this?”

“Everyone.” Emily wiped her nose with her sleeve. “Sarah K. sent it to the whole group chat. They’ve been passing it around all day.”

The rage was instant, white-hot. He wanted to storm into that school, demand names and consequences, but Emily’s next words stopped him cold.

“I started a club,” she muttered. “An LGBTQ+ ally thing. After your assembly. Some kids joined, but now,” She gestured to her phone. “They’re calling it the ‘Freak Squad.’”

Tommy’s throat tightened. His daughter, small and fierce, stared down the same cruelty he faced. Pride and guilt warred in his chest. “You don’t have to fight my battles, Em.”

“I’m not.” She lifted her chin, eyes blazing. “It’s not just about you. I’m not gonna let them be awful to anyone.”

Downstairs, the front door opened, Lisa, returning from her walk to cool off. The sound of her footsteps was steady, familiar.

Tommy pulled Emily into a one-armed hug. “You’re kinda amazing, you know that?”

She groaned but didn’t pull away. “Ugh, don’t get mushy.”

Lisa appeared in the doorway, her gaze flicking between them. “Everything okay?”

Emily shrugged. “Just school drama.”

Lisa hesitated, then sat on the bed beside them. “Do we need to call anyone? Teachers? Parents?”

“No.” Emily’s voice was firm. “We’re handling it.”

We. The word settled over Tommy like a balm. For all the chaos, the fear, the backlash, they were still a team.

Later, as he scrolled through the hateful comments on Emily’s phone (screenshotting, documenting, planning), Lisa leaned against his shoulder. “We’ll figure it out,” she murmured.

Tommy closed his eyes. He wasn’t sure what “figuring it out” looked like, not with the office, not with Emily’s school, not with the world outside their door. But for now, in this quiet moment, it was enough to believe her.

The morning of the Henderson account meeting, Tommy stood in front of his closet, fingers brushing against the charcoal pinstripe skirt he’d bought months ago but never worn to the office. It was sleek, professional, and undeniably bold when paired with his tailored blazer. He hesitated for only a second before slipping it on.

Rachel whistled when she saw him. “Damn, Carter. You’re gonna make the rest of us look boring.”

Tommy adjusted his cufflinks, his pulse thrumming. “Too much?”

“For Karen’s old regime? Maybe. For the new world order?” Rachel grinned. “Perfect.”

The conference room was already half-full when they arrived, the Henderson team, a conservative financial group known for their traditional suits and even more traditional views, huddled over their binders. Tommy caught the moment they noticed his outfit: the flicker of surprise, the raised eyebrows, the whispered aside. He braced himself.

Then the lead client, a silver-haired man with a reputation for cutting contracts over unreturned emails, stood and extended his hand. “Tommy, right?” His grip was firm, his smile genuine. “Love the look. Confidence suits you.”

Tommy blinked. “Uh, thanks.”

The man chuckled. “My daughter’s nonbinary. They’d say I’m ‘evolving.’” He patted Tommy’s shoulder like they were old friends. “Now, let’s talk numbers.”

By the end of the meeting, the account was not only secure but also expanded. Rachel shot Tommy a look that screamed I told you so as they walked out.

Lisa nearly dropped her wine glass when Tommy told her. “Greg Henderson complimented your skirt?”

“I know.” Tommy collapsed onto the couch, still buzzing. “I was ready for a fight, and instead I got that.”

Lisa shook her head, but her lips quirked. “Maybe the world’s not entirely terrible.”

The phone rang before Tommy could reply. Margaret’s name flashed on the screen, and Lisa’s smile vanished. She answered warily. “Hi, Mom.”

Tommy could hear Margaret’s crisp voice through the receiver. “We’re hosting Thanksgiving this year. You’ll all come, of course.” A pause. “And Thomas should wear whatever he likes.”

Lisa’s grip on the phone tightened. “Are you sure?”

“I’ve already told Aunt Lorraine to keep her comments to herself.” Margaret’s tone left no room for argument. “Emily mentioned something about a dance? We’ll need to coordinate schedules.”

When Lisa hung up, she looked dazed. “They’re insisting we come.”

Tommy’s stomach knotted. Margaret’s acceptance at dinner had been one thing, but a full-family holiday was another. “We don’t have to.”

“No.” Lisa took a deep breath. “We’re going.”

Emily’s voice piped up from the hallway. “Dad? Can you help me with something?”

She stood in her doorway, clutching her phone. On the screen was a Pinterest board titled Dance Outfits, filled with sleek suits and flowing blouses, none of the glittery dresses she’d favored in previous years.

Tommy raised an eyebrow. “Since when do you like suits?”

Emily shrugged, but her cheeks pinked. “Since I realized they look cool. And, like… I don’t have to wear a dress just because everyone expects it.”

The words echoed Tommy’s own journey so closely that it stole his breath. He swallowed the lump in his throat. “You want to go shopping?”

Emily’s eyes lit up. “Yes. But,” She bit her lip. “Can we go somewhere no one from school will see us?”

The quiet vulnerability in her voice cracked something open in Tommy’s chest. He pulled her into a side hug. “How about that boutique downtown? The one with the gender-neutral section.”

“Really?” Emily’s grin was instantaneous. “They have this jumpsuit I’ve been dying to try,”

Lisa appeared in the doorway, her gaze flicking between them. “What are we conspiring about?”

“Fashion revolution,” Tommy said, squeezing Emily’s shoulder. “You in?”

Lisa hesitated, then reached for her purse with a sigh. “I’ll drive. But I’m vetoing anything neon.”

Emily groaned, but she was already grabbing her shoes, her earlier hesitation forgotten.

The boutique was a riot of color and texture, racks of clothing organized by style rather than gender. Emily beelined for the jumpsuit, a tailored black number with wide legs and a cinched waist, while Tommy lingered by a rack of silk blouses, running his fingers over the fabric.

Lisa picked up a sleek navy suit jacket and held it up to Tommy. “This would look amazing on you.”

Tommy blinked. “You’re enabling me now?”

Lisa’s smile was small but real. “Turns out, I like you happy.”

Emily emerged from the dressing room, the jumpsuit fitting her like a glove. She spun in front of the mirror, her reflection grinning back. “This is it.”

Tommy’s throat tightened. His daughter, fearless and fierce, claimed her own version of self-expression. No apologies, no explanations. Just joy.

The salesperson, a nonbinary teen with a rainbow name tag, nodded approvingly. “That’s a hell of a look.”

Emily beamed. “I know.”

Later, as they loaded bags into the car, Lisa linked her arm with Tommy’s. “We’re really doing this, huh?”

Tommy glanced back at the boutique, at Emily humming to herself in the passenger seat, at the world shifting around them in small, irreversible ways. “Yeah,” he said softly. “We really are.”

The Setback.

The call came just as Tommy was packing up for the day. Sandra from HR’s name flashed across his phone screen, and his stomach dropped before he even answered.

"Tommy, we need to talk about the Grayson account." Her voice was all tight professionalism, the kind that never preceded good news.

Ten minutes later, he sat across from her in the same sterile HR office where they’d dismissed his complaint months ago. Sandra folded her hands on the desk like she was about to deliver a eulogy. "Grayson Industries has requested a different account manager. Permanently."

Tommy already knew why. He’d seen the way Richard Grayson’s eyes had lingered on his pearl earrings during their last meeting, the way the man’s smile had stiffened when Tommy crossed his legs, the skirt he’d worn that day swishing audibly in the sudden silence.

"They cited ‘cultural differences,’" Sandra continued, sliding a printed email across the desk. The words lifestyle choices and client comfort jumped out in bolded corporate jargon.

Tommy’s fingers twitched against his thigh. "So what’s the play here? You reassign me and hope the next bigot plays nice?"

Sandra sighed. "I’m not unsympathetic, but Grayson brings in twelve percent of our annual revenue. Leadership is suggesting… a compromise."

The compromise, as it turned out, was simple: Tommy could keep his job but only if he stepped back from high-profile client meetings. "Just for now," Sandra added, like it was a temporary bandage and not a slow suffocation.

Rachel was waiting at his desk when he returned, her expression darkening as he relayed the conversation. "Oh hell no," she snapped, already pulling out her phone. "We’re calling the diversity council. And the press. And"

"No." Tommy caught her wrist. "Not yet."

The fight drained out of Rachel’s face. "Tommy. You can’t let them do this."

He wanted to fight. God, he wanted to. But all he could picture was Emily’s face when she’d come home last week, her shoulders hunched after another day of whispers in the hallway.

"I need to think," he said quietly.

Lisa knew something was wrong the moment he walked in. She set down the knife she’d been using to chop vegetables and turned, wiping her hands on a towel. "What happened?"

Tommy dropped his bag on the counter with a thud. "Lost a client. Because of me. Because of this." He gestured bitterly at his clothes a modest sweater and slacks today, nothing that should’ve been controversial.

Lisa’s jaw tightened. "Their loss." But the automatic support rang hollow, her fingers tapping a nervous rhythm against the countertop.

"Emily’s teacher called today," she said after a beat. "Some of the kids were teasing her again. About you."

Tommy closed his eyes. "What did she do?"

"Nothing. Just… took it." Lisa’s voice cracked. "That’s almost worse, Tommy. She’s shutting down."

The unspoken accusation hung between them: This is your fault.

Tommy turned away, gripping the edge of the sink until his knuckles ached. "What do you want me to do, Lisa? Quit? Go back to pretending?"

"I don’t know!" The words burst out of her, sharp with frustration. "But could you just tone it down for the parent-teacher conference next week? For her?"

The request shouldn’t have felt like a betrayal. But it did.

"So now I’m the problem?" Tommy’s voice was dangerously calm. "Not the kids bullying our daughter? Not the school that won’t stop it?"

Lisa flinched. "That’s not what I"

"Then what, Lisa? Spell it out for me."

The silence that followed was thick enough to choke on.

Rachel’s text came at midnight, when Tommy was still staring at the ceiling, Lisa’s back turned to him in bed.

Meet me tomorrow. 8 AM. Café. Bring Lisa.

The café was empty at that hour, just the barista yawning over the espresso machine. Rachel had already commandeered the corner table, her laptop open to a draft press release titled "Corporate Cowardice or Discrimination?"

Lisa stiffened when she saw it. "You want to go public?"

"I want him to fight back," Rachel corrected. She turned the screen toward Tommy. "We have the policy. We have witnesses. Now we make sure Grayson and every other client knows bigotry has consequences."

Tommy traced the rim of his coffee cup. Going public would send a message. It might even force HR’s hand. But it would also paint a target on his back and, by extension, Emily’s.

"What if it backfires?" he asked quietly.

Rachel leaned in. "What if it doesn’t?"

Lisa’s hand found Tommy’s under the table, her grip tight. "It’s your call," she murmured. "But whatever you decide… We’ll handle it."

We were tentative, fragile. But it was there.

Tommy looked at the press release, then at Lisa’s tired eyes, then at his phone, where Emily had texted him a selfie that morning, wearing the jumpsuit they’d picked out together.

"Give me two days," he said. "I need to try one thing first."

Richard Grayson didn’t look surprised when Tommy showed up unannounced at his office. Annoyed, yes. But not surprised.

"I assume HR told you our decision," he said, not offering Tommy a seat.

"They did." Tommy remained standing, shoulders back. "But I thought you should hear from me directly. That account you’re walking away from? It’s grown by twenty percent under my management. Because I’m good at my job. Regardless of what I wear."

Grayson’s smile was patronizing. "This isn’t personal, Thomas. It’s about image."

"Whose image?" Tommy pressed. "Yours? Or the clients who’ll eventually realize you’re on the wrong side of history?"

For the first time, Grayson hesitated.

"I’ll make you a deal," Tommy continued. "You reinstate me on the account, no conditions, and I won’t send this to the Times." He slid a copy of Rachel’s draft across the desk. "Because right now, the only thing hurting your ‘image’ is you."

Grayson’s face went very still as he read.

Tommy didn’t wait for an answer. He turned on his heel and walked out, his heart hammering, the ghost of Rachel’s grin in his mind.

Fight smarter.

He wasn’t done yet.