Work in Progress (untitled) updated 17 February 25

1 - Stacy

The kitchen was small, its surfaces perpetually cluttered despite Edward’s best efforts to maintain order. Stacy stood by the stove, stirring a pot of pasta sauce with one hand while swiping through her phone with the other. She’d insisted on making dinner, as usual, dismissing Edward’s protests with a playful eye-roll.

“Honestly, Eddie,” she said, tilting her head to glance at him. “You’d starve if I didn’t show up. You can’t survive on sandwiches and takeout forever.”

Edward leaned against the counter, tie loosened and sleeves rolled up after a long day at the office. He watched her with an amused smile. “I think I’d manage. But I’m not about to stop you if it means fresh pasta and sauce instead of reheated pizza.”

Stacy stuck her tongue out at him before turning back to the pot. “Exactly. Just admit I’m good for you.”

She was right on target - Stacy’s visits had that effect, her presence lifting the place out of its usual humdrum three-guy apartment routine. She came by once or twice a week, sometimes more, staying over with Edward.

Dave Pérez jogged up the stairs two at a time, cheap bottle of red wine in hand. He knew Stacy would be there - she always was on Thursday nights - and he hoped, with quiet anticipation, that she’d be cooking pasta. The rich aroma of cooking tomatoes confirmed his theory. He hesitated for a moment, adjusting his grip on the wine bottle and smoothing down his work shirt.

“Dave!” Stacy greeted him as he entered, “you’re just in time. Dinner’s nearly ready.”

Dave smiled, his cheeks colouring slightly at her warmth. Stacy had a way of drawing people in, her friendliness toward him often skirting the edge of flirtation but never actual flirting. “Wine,” he said, holding up the bottle in case she might not have recognised the word. “Thought it might go with…whatever smells so good.”

“Oh, perfect!” She set the spoon down and crossed the small kitchen to take it from him, “you didn’t have to, but I’m glad you did. Edward, get some glasses, will you?”

“On it,” he said, opening a cupboard.

They sat down to bowls of spaghetti and sauce twenty minutes later, Stacy sprinkled grated Parmesan over each plate with a theatrical flourish like those television chefs, earning a brief kiss from Edward. They fell into easy conversation as they ate. 

Stacy steering the talk with her usual mix of charm and sharp humour.

“So, Dave,” she said, pointing a chunk of ciabatta at him as if there was more than one Dave. “How’s life at the café? Still pulling heart shapes in lattes?”

Dave chuckled, shaking his head. “Hearts are overrated. I’ve been trying to get good at swans, but they always end up looking like, I don’t know, aliens with wings.”

“Well, I think aliens with wings sound adorable,” Stacy replied, flashing him a grin. 

Edward groaned in mock agony. “Please don’t encourage him,” he said. “Next thing you know, he’ll be naming them.”

“Like you wouldn’t,” Dave shot back, a rare spark of teasing confidence in his voice. The conversation shifted after that, flowing easily as wine bottle emptied and plates grew lighter.

Later, dishes soaking in the sink later, Stacy and Edward settled into the couch in the living room to watch a movie. Dave lingered in the kitchen for a moment before quietly doing dishes. That was the routine - Stacy cooked - Dave did dishes - Edward did nothing. And third roommate Chuck was usually at gym.

Dave weighed up the prospect of joining the couple, he liked their company, but sharing the lounge room created a thirdwheelness in him. “I’ve got some work to finish,” he said casually as he passed the living room on his way to his room. “You guys enjoy the film.”

Stacy’s teasing trailed after him. “What work does a barista have to do at home, huh? You grading coffee beans?”

He glanced back and saw her smirking, her head resting against Edward’s shoulder. Edward shook his head, grinning. “Don’t mind her, Dave. She’s had too much wine.”

Dave gave them a tight smile and disappeared into his room. Hours passed. From his desk, Dave listened to the muffled sounds of the movie, followed by quiet laughter and conversation as Edward and Stacy retreated to the bedroom. He waited, the faint glow of his laptop screen the sole illumination. He wasn’t waiting for any specific sound, but for the absence of them - the heavy, unmistakable quiet of the apartment settling down for the night.

When the clock struck one, Dave decided it was safe. Like a teenager smoking in the bathroom he opened a window wide before applying a layer of bright red polish to his fingernails. He slipped out of his work clothes and into the outfit carefully hidden in his dresser drawer: panties, hose, miniskirt, crop top, padded bra, and blonde wig. 

The wig was far from glamorous - a cheap, synthetic one from a costume store -  but Dave had a buzz cut when he purged a few weeks before. It was a full on discarding of every single item of female clothing, the buzz cut a ‘never-going-back’ move. 

He knew that day he would never crossdress again. 

He knew the next day he would never crossdress again.

He knew for the next week he would never crossdress again.

Then…

He knew he just had to have that crop top - it was sooo pink - it was sooo shiny - it was sooo slutty… 

Dave stepped up into heels that came to him as once-worn - no point in buying new ones. This was only a slight relapse. The sort of relapse quitting smokers have. One cigarette is not failing they say at smokers anonymous. And one outfit is not failing either.

He adjusted his wig in the small mirror above his desk, brushing the synthetic strands into place. He entered his username: Poppy275 and scrolled through the usual forums and blogs, his freshly painted nails catching the light as he tickled the keys. 

There were new pictures - sam:antha had posted more miniskirt and heels pictures and, boy, was that skirt short. Dave zoomed in, sam:antha had a bulge back between her legs, a gaff Dave guessed. That was new.

Dave stood, angled the screen to exclude his face and folded the waist of his miniskirt over until his panties almost showed. Click - eat your heart out sam:antha!

The heels pinched slightly as he posed for another picture, but discomfort was a small price to pay for these fleeting moments of freedom. Then he heard it: the faint creak of Edward’s door opening. Dave froze, his heart pounding. A second later, there was a soft knock at his door.

“Dave?” Stacy’s voice was a whisper, barely audible “you awake?”

He didn’t answer, holding his breath. Maybe she’d go back to bed.

“I heard your keyboard,” she continued. “I can’t sleep, please let me in.”

‘Heard your keyboard?’ Through two closed doors? Did Stacy have bionic hearing or what. Dave assessed his predicament - she could just open the door - he could hold it shut, that would mean crossing the room and she would hear his footsteps. In the absence of a better plan he squeezed his eyes shut and, using the power of his mind, willed her back to Edwards bed. 

Then, the other side of the door, she said it -  her tone light but laced with mischief: 

“What ya wearing?” She teased

His heart dropped into his stomach.

“I’m in bed,”

“No, you’re not,” Stacy replied, her voice now playful. “Come on, don’t be shy. What are you wearing, sweetie? Pyjamas? Nightie? Something more interesting?”

Dave stayed silent, his mind racing. Stacy waited a moment, crossed her fingers and added, “It’s okay Dave, promise I won’t tell.”

Reluctantly, Dave stood, the heels clicking softly against the floor. He cracked the door open just enough to peek out. Stacy’s eyes widened, she pushed the door a fraction wider. Dave expected the same ridicule he had gotten when Edward caught him. Instead, she broke into a wide grin.

“Oh my God, you look adorable,” she whispered. “A little slutty, maybe, but adorable.”

Dave flushed, hesitating. “You’re not…freaked out?”

“Freaked out? No.” She glanced down at his outfit, then back up at his face, her expression equal parts curiosity and delight. “But you have got to tell me how long this has been going on.”

They moved to the kitchen, Stacy careful to keep her voice low. 

Dave was still on edge, but her easy acceptance had disarmed him enough to answer her questions. Over mugs of tea, he told her how he only dressed up when Edward and Chuck weren’t around. He said (lied) Edward had found out by accident the second time he ever crossdressed. Said, once he had fished laughing, Edward had been surprisingly cool with it, and how Chuck could never, ever know.

“No kidding,” Stacy said, shaking her head. “Chuck’s a caveman. But Eddie? Of course he is okay with it. He’s a softie.” She smirked. “Although I don’t think he’d look as good in a skirt as you do.”

“Edward spilled the beans” Dave smiled, his tension easing slightly. “U-huh” Stacy leaned forward, resting her chin in her hand. “So…do you have more outfits? Or is this your go-to?”

“Just this,” Dave admitted, his cheeks warming. “I keep everything hidden. Closets aren’t just for clothes, you know.”

She laughed quietly, then reached over to give his hand a reassuring squeeze. “Well you are out of that closet now, you are braver than you realise, Dave. And for the record? You rock those heels.”

As the conversation turned to lighter topics, Dave realised he felt more comfortable with Stacy than he had with anyone in a long time. When she finally headed back to Edward’s room, she gave him a wink.

“Night, sweetie. And don’t worry, Edward will not dare breathe a word to Chuck - promise.”

Dave watched her go, his heart lighter than it had been in ages. For once, he didn’t feel quite so alone.

2 - The Set-up

The apartment felt crowded the moment Dave stepped through the door. Voices  and clatter of pots in the kitchen blended with the faint strains of a soccer commentator on the TV indicated the third roommate was home. Chuck was apartment odd-man-out. Chuck was a scaffolder, he never passed up a chance to call it a mans job thereby setting himself apart from those who did ‘womens jobs’ - namely barista Dave and office worker Edward. 

Dave tightened his grip on the paper bag he carried - Italian bread and a bottle of wine and steeled himself. This was the first time all four of them would sit down together since the night Stacy saw him dressed, and his nerves were still not letting him forget it.

He stepped into the kitchen, Stacy sautéing vegetables in a pan, Edward grating cheese into a bowl. It may have been paranoia but Dave saw Stacy’s sly look of amusement.

“Dave! Perfect timing. Did you bring something to go with dinner?”

He held up the bag, managing a small smile. “Wine and bread. Figured it couldn’t hurt.”

“Perfect, go keep Chuck company while we cook” Stacy said, taking the bag from him she leaned in just a touch closer than usual, voice low enough that only he could hear “Relax, sweetie.”

Dave joined Chuck in the living room, he was sprawled on the couch, one arm draped over the backrest as he scrolled through his phone. The TV played a soccer match, but Chuck seemed more invested in grumbling.

“Dating apps are a scam,” Chuck declared as Dave sat down in the armchair. “Women just want a free dinner. Swipe right, get a steak, ghost you. Same story every time.”

“Maybe if you acted less like a scaffolder and more like a human being, you’d have better luck,” Stacy teasingly called from the kitchen. 

Chuck scowled “what’s that supposed to mean?”

“It means,” she said, stepping into the doorway with a hand on her hip, “that most women don’t find grunting and crude jokes appealing. Take a leaf out of Eddie’s book, try saying something nice once in a while.”

Edward chuckled but wisely kept his head down, stirring the sauce.

“Nice?” Chuck repeated, incredulous. “You mean all that fake sweet-talking nonsense? I’m not doing that.”

“Then enjoy being single,” Stacy shot back, breezing back into the kitchen.

***

Dinner went about as smoothly as it could with Chuck involved. He complained about the wine being too “fancy” and made crude jokes about pasta shapes, but Stacy handled him effortlessly, tossing barbs that would have earned a punch if they came from anyone else.

Once the plates were cleared, Edward and Chuck drifted to the living room, beers in hand, to watch the second half of the soccer match. Stacy stayed behind to help Dave with dishes, shutting the kitchen door behind.

“Don’t want Chuck yelling for another beer while we’re working,” she said with a wink.

They worked side by side in relative silence, the clink of plates and running water filling the room. Then Stacy turned to him, her tone conspiratorial “Chuck is away the weekend and us three have no secrets.”

“No Stacy!” Dave said “look it is something I tried a couple of times in private.”

Stacy laughed, raising her hands in mock surrender. “Relax! I was teasing. Back to serious for a moment, don’t you ever leave the apartment?”

“I don’t pass and…” Dave hesitated, scrubbing at a stubborn spot on a pan. “I don’t know. It’s…complicated.”

Stacy leaned against the counter, studying him with uncharacteristic seriousness. “I get it, the lack of confidence but with a little guidance you could so pass” she said softly. “But you shouldn’t be feeling trapped, Dave. I mean it.”

Dave glanced at her, unsure what to say. Before he could think of a response, she brightened, her usual teasing smile returning. “I left a bag on your bed. My friend Jilly’s about your size, and she’s not such a slutty dresser. You might like some of her hand-me-downs.”

He stared at her, his jaw dropping. “Jilly? You told her?”

“Of course not,” Stacy said, laughing. “I told her I had a friend who needed some wardrobe help, and she was happy to pitch in. She has no idea it’s you.”

Dave let out a shaky breath. “For a minute, I thought - Edward, you, and now Jilly.”

“Nope. Just me, Eddie, and…” She paused, her grin widening. “Okay, fine, maybe Jilly. And my friend Monica… And Alexia. Oh, I cannot help myself, Dave, having a crossdresser friend is so cool! You’re not angry with me, are you?”

Dave stared at her, his heart racing. Then, despite himself, he laughed - a short, breathless sound. “You’re unbelievably forgivable.”

“And you’re adorable in that slutty outfit.” She bumped his shoulder playfully. “But seriously, take a look at the clothes. If nothing else, it’s nice to have options, right?”

When Stacy finally left the kitchen, heading back to Edward, Dave stood alone for a moment, his mind swirling. She was a whirlwind, Stacy - too much sometimes. But she cared. And for the first time in a long time, he felt like someone really saw him.

3 - The Agreement

The bedroom was in pre-sex mode, the only illumination coming from the soft glow of a bedside lamp. Edward stretched out in the bed, his head resting on a pillow as Stacy busied herself, always the same pre-bedtime routine: fold, fold, fold, iPhone to charge pad, fluff pillow three times, pull hair into a loose ponytail. 

Edward had learned not to rush her; she’d get to him after the ponytail bit.

Finally, she climbed into bed beside him, sliding under the covers. Edward reached for her, but she pressed a hand against his chest, stopping him mid-motion. “Hold up tiger,” she said, her tone semi-serious. “There’s something I want to talk about first.”

Edward sighed, already sensing that any chance of getting his way tonight depended on how well he navigated this conversational minefield. “Okay,” he said, folding his arms behind his head. “What’s on your mind?”

Stacy turned on her side, propping herself up on one elbow as she looked at him. “It’s about Dave.”

Edward blinked, thrown by the shift in topic. “What about him?”

“I want to have him over,” Stacy said, her words measured. “Like, at my place for a Saturday evening.”

Edward’s brows furrowed. “Why? He’s not exactly the life of the party.”

Stacy swatted his arm. “Be nice. I like Dave. And so do my friends. They’ve heard about him…”

“Wait,” Edward interrupted, sitting up slightly. “They’ve heard about him? What are you telling them, exactly?”

“Nothing bad!” she said quickly. “Just that he’s sweet and shy and…unique. Now they’re curious is all.”

Edward tilted his head, studying her. “Curious how?”

Stacy hesitated, then shrugged. “They think it’s cool that I know someone like him. You know, a part time crossdresser - closet door open just a teeny tiny bit and peeping out. They want to meet him.” Even in the half light Stacy recognised Edwards ‘yea, right’ face. “Okay, okay, Mr Smartypants, I admit it, I want to show Dave off.”

Edward’s lips twitched into a smirk. “So, what, you’re his fag-hag now?” The words barely left his mouth before he realised his cock blocking mistake. 

Stacy’s expression darkened, her playful tone now recent history. “Excuse me?” she said, her voice icy. “Did you just call me a fag-hag?”

Edward raised his hands defensively. “It was a joke, Stacey. Relax.”

She sat up fully, glaring at him. “Oh, I’m sorry, I must have missed the part where being supportive of someone makes me the punchline of your lame jokes. Who even are you, Chuck mark two?”

That stung, and Edward winced. “Whoa, hey. That’s not fair. You know I’m not like him.”

“Could’ve fooled me,” she shot back, crossing her arms. “You’re supposed to be Dave’s friend, Eddie. He’s already dealing with enough without you acting like his life is some kind of sitcom.”

Edward sighed, running a hand through his hair. “Okay, okay. I’m sorry. I didn’t mean it like that.”

Stacy’s glare softened slightly, though she still looked annoyed. “Good. Because if you think I’m going to let you - or Chuck, for that matter - make Dave feel ashamed of who he is, then I’ve got news.”

Edward nodded, his tone quieter. “Okay, I get it. I’ll be better.”

She eyed him for a moment longer, then leaned back against the pillows with a sigh. “Good. So, you’re okay with him coming over, then?”

“Sure,” Edward said. “If it makes you happy, then it makes me happy.”

Stacy smiled, leaning over to kiss his cheek. “Thank you. And for the record, my friends are going to make sure he has fun. He just needs a little push.”

Edward reached out to pull her closer. “Now that we’ve got that sorted, can we get back to where we left off?”

She laughed softly, shaking her head. 

Edward lay quietly after sex - if Stacy had a superpower it had to be getting what she wanted, and if getting to fuck Stacy meant Dave spending an evening surrounded by her lively, overbearing friends, then so be it. Good luck, Dave. Edward couldn’t shake the nagging feeling that, as wild as Stacy’s plan seemed, it might actually be just the kick in the pants Dave needed.

***

Dave and Edward sat in the living room, a rare moment of calm in their often chaotic apartment. The dishes from last night’s dinner still sat on the coffee table, and the faint hum of traffic drifted in through the open window. Dave shifted in his seat, toying with the hem of his hoodie, before finally breaking the silence.

“I’ve been thinking,” he began, his voice quieter than usual. “About Stacy.”

Edward looked up from his phone, raising an eyebrow. “What about her?”

Dave hesitated, then took a deep breath. “She didn’t just happen to discover me, did she? Like you did. You told her.”

Edward chuckled, though a flicker of guilt crossed his eyes. “Keeping secrets from Stacy? Impossible, mate. She sees right through everything.”

Dave narrowed his eyes. “So, you also told her the rest -  about our little arrangement? How I have to clean the apartment in exchange for your sealed lips?”

Edward winced, his cheeks flushing pink. “Yeah, about that…”

“Have you told Chuck?” Dave said, crossing his arms. “Or are you still holding that over me so that I’m still stuck cleaning the entire apartment - except Chuck’s room of course, because even I have a limit.”

Edward raised his hands in mock surrender. “Alright, alright. I admit it. It is a little unfair. But hey, the place has never looked better! And honestly, if Stacy found out, she'd probably have you cleaning her place, too. Go ahead, spill the beans if you want.”

Dave shook his head, exasperated. “Unbelievable.”

Edward smirked and leaned back in his chair, clearly unbothered. “Speaking of Stacy, she’s got this idea for Saturday. Wants you to spend the evening at her place.”

Dave blinked, caught off guard. “What? Why?”

Edward shrugged, feigning casualness. “She thinks it’d be good for you. Don’t quote me but I’m guessing she might want to give you a bit of a makeover.”

Dave groaned, sinking further into the couch. “A makeover? Are you serious?”

“Relax, let her pamper her pet crossdresser. And stop pretending Dave” Edward said, waving a hand dismissively. “I bet you will have fun.”

Dave eyed him skeptically. “You’d better not be setting me up for something.”

Edward grinned but said nothing. It took more convincing - and a promise that Chuck wouldn’t somehow get involved - but eventually, Dave agreed. With a nod of satisfaction, Edward grabbed his phone and called Stacy. “It’s all set,” he said. “Dave’s coming over Saturday. Just…maybe don’t mention anything about your friends, he might back out.”

“Got it,” Stacy replied. “Put him on. I want to check something.”

Edward knocked on Dave’s door, handed the phone.

“Hi, Stacy,” he said cautiously.

“Hey, sweetie!” she said, her voice full of warmth. “Have you tried on the clothes I left you yet?”

Dave hesitated, but Stacy’s tone was so casual that he found himself answering honestly. “Yeah. They fit…tell Jilly thanks and I like them.”

“Good,” she said, a smile evident in her voice. Then she dropped her tone, turning conspiratorial. “Don’t mention this to Edward, but I want you to bring the black panty grazer skirt and shiny pink crop top you were wearing that night.”

“I was thinking this calf length skirt and…”

“WAIT! - you are wearing it? FaceTime” Stacy over enthused a little, she screen grabbed the image, forwarded it to Jilly - ‘looking sooo cute, recognise your pencil skirt?’  

“Just trust me on this Dave - pack what I said in your bag and bring them on Saturday.”

Dave hesitated, his grip tightening on the phone. “Why those, specifically?”

“Oh, come on,” Stacy said, her tone dripping with playful mischief. “Because your legs looked amazing in that little skirt. And the crop top? Let’s just say it screams ‘fun.’ I’ll soon have you looking your best.” 

Before he could respond, Stacy upped the ante. “Or…” she began, a sly edge creeping into her voice. “If you really want to impress me, you could wear them to my place instead of packing them. I mean, why not? They’re comfy, aren’t they?”

Dave’s jaw dropped. “What? No way!”

Stacy burst out laughing, the sound bright and unrestrained. “I’m just teasing, but seriously, it’d save time. Think about it - you’d turn a lot of heads on the way here.”

“You’re improbable,” Dave muttered, though a faint, reluctant smile tugged at the corner of his mouth.

“Improbable am I?” Stacy chuckled, clutching her chest with mock drama. “I’ll have you know I’m a statistical miracle. 

“Fine, I’ll pack them.”

“Good” Stacy said, the grin wider than ever.

4 - Makeover Night

Dave arrived at Stacy’s apartment a little after seven, still wearing his café uniform,  his backpack slung over one shoulder. The small but stylish space smelled faintly of vanilla and lavender, the scent mingling with whatever lotion Stacy always seemed to use. She greeted him with her usual enthusiasm.“Long day?” she asked, wrinkling her nose.

Dave set his shoes neatly by the door. “Cafés don’t exactly slow down on the weekend.”

“Well, you’re here now, and I’ve got big plans for you. But first…” She leaned closer, scrunching her nose playfully. “Shower, no stepping into my evening sticky from work.” Dave flushed, mumbling an apology, but Stacy waved it off with a laugh and pointed him toward the bathroom. “Stacy’s top tip before you hop in, hairy legs and hose - ugh!” she added, her tone casual, “there’s hair removal cream in the cabinet if you’ve not shaved yet. We have all the time in the world tonight. Convincing Edward tested my womanly charms to the max so tonight is probably a one-time event.”

Dave hesitated in the doorway, turning to face her. “You think I should?”

She shrugged with a mischievous grin. “Why not? You’re not seeing anyone right now, are you? Then no-one is going to notice. Trust me, getting smooth is so worth it.”

His heart thudded in his chest, a mix of reluctance battled with eagerness in a sea of curiosity that was churning inside him. He’d read countless stories online and crossdressers always removed their body hair for a makeover. He’d even thought about it himself, but something had always stopped him. Now, with Stacy’s encouragement and the sense of an opportunity he might never have again, he nodded.

“Okay, sure” he said softly. “Why not.”

The bathroom filled with steam. Dave stepped out of the shower, his skin slick and pink from the hot water. He’d gone all in, slathering the cream over every inch of his body from the neck down and marvelling at the smoothness it left behind. Towelling off felt strange - almost softer somehow, his skin hypersensitive to the fabric of the towel. It was exhilarating and disconcerting all at once. He opened his backpack, took out his gaff from Friends of Dorothy (the crossdressers emporium) and situated his cock before cock bending was no longer an option. The gaff had been expensive, more than he wanted to spend, but a pink so perfect a match to his crop top meant price was not an issue.

As he finished, he heard Stacy talking, thought she was on speakerphone, but as he opened the door, he saw three shadows in the hallway.

“Dave!” Stacy called as he emerged in the borrowed bathrobe she’d left hanging on the bathroom door. “Meet the girls.”

Standing beside her were two women he didn’t recognise. One held a round hat box that immediately piqued his curiosity, while the other carried a large makeup tote slung over her shoulder.

“This is Jilly,” Stacy said, gesturing to the one with the hat box. “Jilly’s a hairdresser. And this is Monica, beautician extraordinaire.”

Dave’s mouth went dry, and his instinct was to retreat back into the bathroom like a tortoise sensing danger. But part of him - a small, deeply buried part - thrummed with anticipation. Was there a crossdresser alive who hadn’t fantasised over this exact scenario? 

Three beautiful women fussing over him - a full makeover? Bring it on!

He managed a shaky smile, unsure if it was excitement or nerves making his hands tremble. “Hi,” he said weakly.

“Relax, Dave,” Jilly said, her voice warm and inviting. “We’re going to make you look amazing.”

“And don’t worry,” Monica added with a wink. “Jilly and I have done this before.”

The next hour passed in a blur. Dave sat in a chair in Stacy’s bedroom, legs clamped together, trying to stop his hands from trembling. Monica laid out her makeup kit with the precision of a surgeon preparing for an operation.

“You’re shaking too much,” Stacy observed, handing him a glass of wine. “Here, drink this. And take this too - it’s a Valium. Nothing sketchy, I swear. Just something to help you relax.”

“It’ll take the shake out of shakeover” Monica laughed at her own joke “makeover - shakeover, get it?”

Dave accepted both. As the wine warmed and the pill began to kick in his shoulders eased, the tremor in his hands stilled. Slowly, he started to enjoy the experience. Monica worked fast, painting his nails and applying layer after layer of makeup with practiced ease, all the while chatting and laughing, Stacy watched and documented the transformation on her iPhone.

Jilly unpacked the “hat box,” and began styling the long, dark wig while Monica and Stacy chatted in the kitchen. “How far along did you say he was?” Monica tested.

“Two, no, must be almost three weeks now.”

Monica leant close “Dave kept pulling his bathrobe together as if he was hiding something.” 

“U-huh, probably falsies or his bra.”

“Here’s what happened” Monica loved gossip “well I ‘accidentally’ got my brush caught - I tell you he is wearing a thong Stacy, that your doing?”

“Oh, stop it Mon, I don’t know. Probably got the idea from the internet.”

“Probably frightened of displaying a hard on more like.” Monica smiled.

“Don’t spoil the evening Monica.” Stacy laughed softly.

“Just go have a look.” Monica laughed “it’s like those and adult version of those books for kids - where’s willy.”

Stacy laughed, calmed “Sure… like I’m gonna go and rip his bathrobe open. Let it go Mon.”

When Jilly called the others and stepped back Dave barely recognised himself in the mirror. His reflection stared back, eyes wide beneath expertly blended eyeshadow and fluttery lashes. His lips were painted a glossy, natural pink, and the wig framed his face perfectly, softening his features.

Dave smiled “so this is what outside the closet looks like” but that might have been the Valium talking.

“Gorgeous,” Stacy declared “get dressed. We’re dying to see the whole look.”

Dave changed in Stacy’s bedroom, he put on his black add-a-size bra before slipping into the skirt and crop top she’d requested. 

The panty grazer skirt barely covered his new gaff. 

The pink crop top shimmered with every breath. 

The shoulder straps of the black bra, visible at his neckline, for added sluttiness. 

Dave stood in front of the full-length mirror, he couldn’t help but fall in love with the transformation as he snapped a few quick selfies. He looked like someone else entirely - no need to blur his face before he posted. Beat that sam:antha !

Stepping out into the kitchen, where Stacy and her friends waited in their own party clothes, was a different story. The sight of them made his confidence falter, and he hesitated in the doorway, tugging down the hem of his skirt that had been too long a few steps ago.

Stacy noticed immediately and crossed the room to him. “Hey,” she said softly. “Don’t overthink it. You look incredible.”

“Too slutty?” Dave asked nervously.

“Not even close,” Stacy said with a grin, turning to the others. “What do you think, ladies?”

Jilly and Monica let out approving ooh’s and ahh’s, clinking their glasses together in celebration of what they had created.

Dave smiled, unsuredness banished thanks to Valium. He let himself enjoy the moment.

***

Dave hesitated in the kitchen doorway, still self-conscious despite the compliments. His heels clicked softly against the tile floor as he joined the others at the counter. Stacy handed him a glass of wine, the same large size they were drinking from. He took a sip but immediately tipped back a larger gulp, his nerves demanding something to take the edge off.

“Whoa there,” Jilly said with a laugh, raising an eyebrow. “Slow down, honey. The night is young.”

Dave nodded, setting the glass down but not letting go of it. “Sorry, just…this is all new. I mean, girls’ night.” He gestured vaguely around the room. “What do you even do? What usually happens?”

Monica burst into laughter, nearly spilling her wine. “Oh, sweetie. If you’re picturing pillow fights in our underwear, let me stop you right there. That only happens inside men’s heads.”

Jilly and Stacy laughed along, nodding in agreement. “Yeah,” Jilly said, smirking. “That’s some frat boy fantasy nonsense. Real girls’ nights are a lot more... wild.”

Stacy rested her chin in her hand, smiling as the other two began throwing out suggestions.

“We could watch a movie,” Jilly said, swirling her wine. “Something cheesy, maybe one of those bad romance flicks.”

“Or binge a series,” Monica added. “Find something juicy and gossip about the actors.”

“Or just stay in and chat,” Jilly said. “Gossip is half the fun anyway.”

Dave was starting to relax, picturing the low-key evening of wine and lighthearted conversation. But then he noticed Stacy’s smile shift, that slightly mischievous look appeared - like when she prised him from the safety of his bedroom at one in the morning. The other two noticed it too, and after a brief pause, they burst out laughing.

“Wait,” Monica said, pointing at Dave. “Stacy never told you?”

“Stacy !!!” Jilly chimed in, grinning like a cat with an entire bunch of trapped mice. “We’re all dressed for a night on the town, sweetie.”

Dave froze, his grip tightening on his wineglass. “What?”

Stacy’s phone pinged loudly on the counter. She picked it up, glanced at the screen, and her grin widened. “Taxi is outside.”

“Taxi?” Dave repeated, his voice rising slightly. “Wait, I didn’t agree to…”

But before he could finish, Stacy looped an arm through his, and Monica the other. “Oh, hush,” Stacy said cheerfully. “You’ll love it.”

“Trust us,” Monica added, steering him toward the door. “Downtown Ashminster is way more fun than pillow fights.”

4 - Club Time

Dave barely had time or, in all honesty, desire to protest. They whisked him out of the apartment. Within moments, he was tucked into the back of a taxi, sandwiched between Stacy and Monica, Jilly climbed into the passenger seat.

The city lights of Ashminster blurred outside the window as the taxi sped along - destination downtown. Dave sat stiffly, trying to collect his thoughts, but Stacy nudged him gently with her elbow. “Relax, we’ve got you. Just trust us. Tonight is all about having fun.”

Dave exhaled slowly, forcing himself to lean back against the seat. Part of him wanted to demand the driver turn around and take him back to the safety of Stacy’s apartment. But another part - the chemically enhanced brave part - screamed tonight will be something he’d remember forever.

***

The atmosphere in the taxi was electric, filled with the playful banter of Stacy, Jilly, and Monica. Dave sat wedged between Stacy and Monica, doing his best to appear as playful despite the whirlwind of new experiences. The driver, a cheerful man in his forties, seemed right at home with the lively group.

“So, what’s the occasion tonight, ladies?” the driver asked, glancing at them in the rearview mirror. “You all look like you’re ready for something special.”

“Oh, it’s a big night,” Jilly said, leaning forward. “We’re taking our crossdresser friend out for the first time.”

Dave froze, his cheeks flushing as the driver chuckled. Stacy gave Dave’s knee a reassuring pat, her smile radiating confidence.

“Lucky friend, getting to hang out with you three,” the driver said, glancing at Dave again. “And looking pretty good, I must say.”

Dave smiled “Thanks,” 

Jilly quickly chimed in with a laugh. “For the record, I’m Dave’s unofficial fag hag,” she announced dramatically, gesturing to herself. “Right, Dave?”

Monica snorted. “Please. If anyone’s the fag hag here, it’s me. Just look at her face and nails.”

“Both of you can step aside,” Stacy said with a grin. “I’ve been here from the beginning. I’m clearly queen of fag hags.” All three burst out laughing.

Even the driver couldn’t help but chuckle, shaking his head as he glanced at them in the rearview mirror. “You four are something else. Poor Dave’s got his hands full.”

“Speaking of hands full,” Monica said glancing at Stacy with a mischievous grin, “we’ve got an important task before the club. We can’t call her Dave all night - that’s a travesty. She needs a name as fabulous as she looks.”

“How about Davina? Do I look like a Davina?” Dave looked pleased with himself, his self femnaming surprising everyone.

“Absolutely not!” Jilly cut in, waving a dismissive hand. “Be quiet, nameless one. We get to name you - it’s our sacred right.”

“Exactly,” Stacy chimed in. “And ‘Davina - where did that come from Dave? it’s so... yawn. We need something that sparkles!”

Monica leaned forward, tapping her chin theatrically. “I’m feeling bold. What about Scarlett? It’s sexy, powerful - a total showstopper.”

Stacy cut in “we need to see the whole picture, what is your family name?”

“Pérez” Dave smiled “Dave Pérez.”

“Or Veronica, Veronica Pérez” Jilly added, gesturing with an imaginary martini. “Sophisticated, but still approachable. A woman who owns the room.”

Stacy tilted her head, scrunching her nose. “Hmm. Good, but... I don’t know. They don’t quite fit. She’s not a Scarlett or a Veronica. Both sound a little too transvestity”

The women spiralled into a whirlwind of suggestions - Claudette, Isabelle, Trixie - with each name drawing giggles and dramatic vetoes.

Finally, Stacy snapped her fingers, her face lighting up. “I’ve got it! Poppy. It’s perfect. A little fun - just like our newly minted girlfriend.”

A beat of silence fell over the taxi as the name sank in. 

Jilly nodded, a satisfied smile spreading across her face. “Poppy Pérez. Yes. It’s perfect.”

“Wait - Poppy?” Dave blinked, his cheeks flushing, out of all the thousands of names how had Stacy accidentally hit upon his online name. “I really don’t get a say in this?”

“Absolutely not, Poppy Pérez” Stacy said, looping her arm through his and squeezing playfully. “The council has spoken. Welcome to the world, Poppy!”

The taxi erupted in cheers and laughter, with Dave - Poppy - laughing nervously but unable to hide a shy smile as the name settled around him like someone else's still warm but unfamiliar, coat.

Besides, I just messaged Edward, he said Poppy suits your look.” Stacy lightly kissed Poppy's cheek “I sent him a couple of pictures of you getting your makeover.”

Dave’s eyes widened. “You what?”

“Relax,” Stacy said with a wink. “He said Poppy looks and sounds adorable.”

Dave groaned, sinking further into his seat as the three women laughed again, their voices full of camaraderie. The driver smiled as he slowed the taxi and destinated at a bustling street corner bathed in neon light.

“Well, Poppy,” the taxi driver said, glancing back with a playful wink. “Looks like you’re in for a good night. Enjoy yourself.”
Poppy mustered a weak smile, her stomach twisting with a mix of anticipation and dread. As they climbed out of the taxi, Stacy hooked an arm through hers, steady and reassuring. “Come on,” Stacy urged, her grin as radiant as the neon signs reflecting off the slick pavement.

King Street in Ashminster’s club quarter was alive—bright lights blinking like stars fallen to earth, the rhythmic thud of bass lines vibrating through the air, and crowds of people dressed to dazzle, moving with purpose toward packed venues.

“We’ve got this,” Stacy whispered, leaning close as they approached the sleek, velvet-roped entrance of Pulse, the district’s most coveted club.

As Poppy stepped inside, the music hit him like a wave, walls pulsed with light, and the air was electric with the thrill of discovery. Poppy’s nerves melted just a fraction as Stacy guided him to the bar, with Jilly and Monica trailing behind, already laughing and trading teasing remarks.

***

The four women claimed a corner of the bar, leaning into each other to make their drink orders over the thundering beat. Stacy ordered Poppy a cocktail - something sweet and fruity. Monica was already scanning the room, her sharp eyes hunting for the next story-worthy encounter.

“This is your coming out night,” Stacy said firmly to Poppy as she clinked her glass against his. “Just enjoy it. You deserve this.”

Poppy took a sip, the alcohol warming his chest and dulling the edge of  his nerves. “It’s loud,” he shouted back, to which Jilly grinned.

“That’s the point!” Jilly dragged him toward the dance floor, leaving Stacy and Monica to fend for themselves.

At first, Poppy was stiff, movements uncertain as he navigated the writhing crowd. But then, something shifted. The beat seemed to sync with his pulse, and for the first time, he really was not overthinking. He let go feeling lighter than he had in years.

***

The night sped past Poppy in a blur of laughter, dancing, and even fleeting conversations with strangers. Stacy remained Poppy’s anchor, always nearby, ensuring he wasn’t overwhelmed.

When the clock struck two, and the night began to thin, Stacy took Poppy’s hand. “Come on, let’s get out of here. Jilly and Monica are crashing at Jilly’s place.”

The cool night air was a relief as they flagged a taxi. Poppy slid into the back seat, feeling the night settle over her like a comfortable weight. Stacy climbed in beside him, “Edward is expecting me Poppy.”

“How did you come up with the name Poppy?”

“You don’t like it?” Stacy was suddenly alert. Dave shrugged. Stacy smiled “I could call you starting Poppy…” she looked out the window a while.

Dave thought sticking with Poppy was safest. “I like Poppy.” He eased his key in the lock, only the feint refrigerator hum greeted them. Poppy and Stacy slipped off heels in the hallway, she gave him a quick hug before heading to Edward’s room.

As he removed the layers of makeup in front of his small vanity, Dave caught his reflection - a faint smear of glitter clinging to his cheekbone the only evidence Poppy ever existed. 

From the moment Stacy opened her apartment door the night had been a never ending series of terrifying events. But he couldn’t deny the flicker of pride at how he’d handled going out in public for the first time.

5 - Morning After

The smell of coffee wafted through the apartment, pulling Dave out of a dreamless sleep. He threw on a loose t-shirt and sweatpants, padding out to the kitchen. Edward was at the stove, making a morning after bacon and eggs breakfast, Stacy was perched on the counter mug in hand, her hair still tousled from sleep.

“Morning,” Dave said, his voice hoarse. He grabbed a cup and poured himself some coffee.

“Morning, Dave or Poppy - what is protocol for bathrobe?” Edward replied, glancing over his shoulder with a grin. “Heard you had quite the night.”

“Dave is good, always Dave. We don’t want Chuck getting a shock” Dave smiled. “Thanks for lending me your girlfriend for the evening. She was literally incredible.”

Stacy rolled her eyes with a laugh. “Oh, please. I was just there to make sure you didn’t bolt. You were amazing, totally rocked it - even when that horrible pig-man tried to call you out.” Despite what he told Eddie, Stacy wanted to call him Poppy and so she avoided using either.

Dave paused, the memory flashing in his mind: the man’s sneering face, the accusatory tone. For a second, he’d been paralysed, but Stacy’s sharp retort had shut him down, and the support of the group had kept him steady.

“Yeah,” Dave said slowly, a wry smile tugging at his lips. “That was… something, thanks for having my back.”

“Always,” Stacy said, hopping off the counter to grab a plate of eggs Edward had just finished. “And for the record, you handled that like a champ. Way better than most out for the first time would’ve.” She set the plate on the table, then turned to Dave, a mischievous glint in her eye. “Now, speaking of closets…”

Dave theatrically groaned.

Stacy grinned. “So, are we finally admitting you’ve outgrown yours?”

Dave stared into his coffee for a moment, then looked up with a small but genuine smile. “You know what, Stacy? You’re right. You’ve led me so far away from the closet, I couldn’t find my way back even if I tried.”

“Good,” Stacy said, her tone surprisingly gentle. She gave his shoulder a reassuring squeeze. “Because you’re way too fabulous for hiding.”

Edward set down a second plate and took a seat, raising an eyebrow. “Does this mean I need to start clearing space in the bathroom for extra makeup?”

6 - Chuck

Edward and Stacy had just left for a trip to the mall. Dave sat at the kitchen table, nursing the last of his coffee when Chuck burst in, still breathing heavily from his run. He grabbed a protein shake from the fridge and leaned against the counter, his broad shoulders filling the small space.

“Morning, Dave,” Chuck said.

“Morning. Good run?” Dave asked.

Chuck hesitated, then took a swig from his bottle. “Yeah. Speaking of runs, I ran into a mate. Said he saw Stacy and her crew at Pulse last week.”

Dave’s stomach dropped, the coffee in his hand suddenly feeling too hot. He managed a weak nod. “Oh?”

“Yeah. Bob said there was someone new, a slutty chick in a pink crop top and miniskirt, hanging around them. Sounds interesting.” He tilted his head, his expression sharpening. “Didn’t know Stacy had a new friend. You ever meet her?”

Dave froze. The words caught in his throat like barbed wire. Every instinct screamed at him to deflect, but, it was only a matter of time. He set the coffee cup down, steadying his breath. “Last weekend, that… was me,” Dave said, his voice barely above a whisper. “I was the one wearing the crop top and miniskirt.”

Chuck’s brow furrowed deeply. He let out a short, incredulous laugh, shaking his head like he was trying to dislodge the thought. “Fuck off, Dave. Don’t start with me this early.”

“I’m serious.”

Chuck’s laugh morphed into a sneer. “You? In a miniskirt?” He let out another humourless chuckle. “Stacy wouldn’t be seen within a country mile of a fucking tranny.”

The words stung, but Dave stood abruptly, his chair scraping against the floor. Without a word, he walked out, his heart pounding in his ears. In his room, Dave pulled Poppy’s outfit from it’s hiding place. For a moment, he hesitated, his fingers trembling over the fabric. Then, with a sharp breath, he slipped into the clothes. Standing before the mirror, he adjusted the wig. Poppy stared back at him.

Squaring his shoulders, Poppy walked back to the kitchen.

Chuck was eating bacon straight from the pan when Poppy stepped into the room. The colour drained from his face, his mouth hanging open.

“Now do you believe me?” Poppy asked, voice steady despite the storm raging inside.

Chuck blinked, his jaw tightening. His eyes scanned her, taking in the wig, the heels, the outfit. For a long moment, he didn’t speak. “Shit,” he muttered under his breath, rubbing a hand over his face. Turning to the window, he stared out as if the answer to this puzzle might be written in the sky.

The silence was unbearable. Poppy stood rooted, unsure whether to stay or retreat.

Finally, Chuck turned back, his face twisted in a mixture of disbelief and frustration. “Look,” he said, his tone hard. “You know my feelings about… this sort of thing.” He gestured vaguely at Poppy, his lip curling slightly. “If this is some sick joke, you’re pushing it too far. But if it’s not…”

He trailed off, then took a step away, holding out an arm full stretch. He clenched his fist, the veins in his forearm bulging. “You stay this far, got it? I don’t want you getting too close or friendly. This…” he shook his fist “is as close as we’re ever getting, understand?”

Poppy swallowed hard, throat dry. “Yeah. I get it, Chuck.”

Chuck gave a short nod, his jaw still tight. “Good. Just… keep it out of my face, alright?” He grabbed his protein shake and stormed out of the kitchen only to return a second later “and don't be telling anyone I know, this is between us, right?.” As the door to the shower slammed shut, Poppy felt like someone who had escaped a beating by a whisker and went to change back into Dave clothes. 

It wasn’t acceptance, not even close. 

But it was one step further from the closet.

***

Mid week the posse - Jilly, Monica and Stacy - met up in The Bean Scene for a debrief. 

“Finally, there you are,” Stacy said waving Monica over, Stacy sat alone in a corner booth. “I just ordered for us. You’re still a caramel latte girl, right?”

Monica gave a cautious smile as she slid into the booth. “Does a leopard change it’s spots? What’s got you so chipper this morning?”

Stacy leaned in, her voice low but brimming with enthusiasm. “Poppy. I think she’s really starting to come into her own! The night out was such a big step forward. Don’t you think?”

Monica’s eyebrows rose slightly. “It’s good that Dave, I mean Poppy, felt comfortable enough to go out, but… maybe don’t push too hard?”

Stacy tilted her head, her smile faltering. “Push? I’m not pushing. I’m just being supportive. Isn’t that what friends are supposed to do?”

“Of course,” Monica said, carefully. “But I’ve seen you get a little… overzealous before. Remember that time with the yoga retreat? Or the pottery class? You threw yourself in so hard that it overwhelmed everyone else involved.”

Stacy rolled her eyes. “This isn’t pottery, Monica. This is someone’s identity. If he hides away Poppy will be like I was…” she gave her friends hand a squeeze “before we all became us.”

At that moment, Jilly arrived, jangling of bracelets announcing her presence like a two legged wind chime, she slid into the booth beside Monica. “What’s all this about identity?” she asked, snagging the latte the barista delivered to their table.

Monica shot a look at Stacy. “We’re talking about Dave. Or Poppy as Stacy calls him now, I guess.”

“Oh, right. The pet crossdresser project,” Jilly said, raising an eyebrow. “How’s that going?”

Stacy’s enthusiasm reignited. “Amazing! Sunday afternoon, when Chuck’s out, she walks around in those sport leggings and top you gave her, Jilly, without a care in the world.  I’m just… so proud of how far she’s come.”

Monica shifted uncomfortably, her fingers tapping on the side of her cup. “Stacy, maybe just… take a step back? You’re really enthusiastic, and that’s great, but if you’re not careful, you might end up alienating Edward.”

Jilly nodded, her lips curving into a wry smile. “Yeah. Eddie might be fine with the occasional girls’ night, but if he feels like Poppy’s getting all the attention… well, that’s still another guy in the picture, no matter how she’s dressed.”

Stacy waved a dismissive hand. “Oh, please. Edward’s fine. He’s cool about all this.”

“Are you sure?” Monica pressed. “Because it kind of sounds like you’re… well, all-in with this whole Poppy thing. And maybe Edward’s picking up on that as well.”

Stacy’s laugh was sharp and defensive. “Jealous much? You were both like this back in school when I got that hamster."

“So, having a pet tranny is like that, how?” Jilly asked, arching an eyebrow.

Stacy blinked, momentarily caught off guard. Then she grinned. “You know, I kind of like the sound of that. Maybe I’ll call her my little tranny when it’s just the two of us.”

“just the two of us - fuck sakes Stacy” Monica looked appalled. 

Stacy’s smile softened. “I’m just being supportive. And that costs nothing, right?” She scooped the froth from her latte. “You two worry too much. Everything’s fine. Dave is like a baby learning to walk, once he gets confident in public I’ll be done. You’ll see.” But as the conversation shifted to lighter topics, Monica couldn’t shake the feeling that Stacy might be pushing things further than anyone - including Dave or Poppy - was ready for.

7 - Film Night

A few days had passed, and Dave had been keeping a low profile. Stacy, mindful of Jilly and Monica’s concerns, hadn’t mentioned Poppy to anyone, not even Edward and especially not Dave. Chuck, meanwhile, had taken a cautious approach when alone with Dave, occasionally throwing out questions like tiny fishing lines.

“You wanna be a woman?”
“No.”

“Gonna dress up like that all the time?”
“No.”

One or two inappropriate questions were enough to satisfy Chuck until he thought up two more.

One evening, with Stacy and Edward out, Dave decided to embrace a bit of quiet freedom. He slipped into the calf-length skirt and blouse Jilly had given him, the soft fabric settling comfortably against his skin. After adjusting his wig and makeup, he settled in the living room with a glass of water, flipping through channels until he landed on an old comedy film.

The sound of Chuck’s door opening made Poppy tense, but he stayed put, determined not to retreat to his room like a guilty secret.

From the kitchen, Chuck called out, “Want coffee, Dave?”

Poppy hesitated for a moment. “Sure.”

A few moments later, Chuck appeared in the doorway with two mugs in hand. He stopped short, his brows lifting slightly as he took in Poppy’s outfit.

“Well, that’s different,” he muttered, setting the mugs on the coffee table. He didn’t comment further, just dropped into the easy chair across from the sofa where Poppy was sitting.

“Thanks,” Poppy said, picking up the mug.

Chuck grabbed the remote and turned up the volume on the film. They watched in silence, a tense truce hanging over the lounge room. When the credits rolled, Chuck stretched and glancing over at Poppy said “you got a name for… this?” he asked, gesturing vaguely at the room.

Poppy hesitated, then smiled. “Poppy.”

Chuck said it under his breath, as if testing the sound. “Poppy… Poppy.” He nodded slightly. “You want me to call you that when you’re dressed like this?”

Poppy’s heart skipped. “Yeah, if you’re okay with that.”

Chuck shrugged, his expression neutral. “Alright, Poppy.” He smirked slightly, leaning forward with his elbows on his knees. “You’d look better with some tits, though. Just sayin’.”

Poppy blinked, caught off guard. For a moment, she debated whether to let it slide or speak up. She decided to take a risk. “Can you… not be so crude when I’m dressed like this?”

Chuck’s eyebrows shot up, but after a moment, he nodded. “Fair enough Poppy. My bad.”

Poppy stared at him, amazed. “Thanks, Chuck.” Poppy laughed, relaxing a little. “Yeah, breast forms cost a lot. There’s this place called Friends of Dorothy, it’s a crossdresser’s shop. They have some really good ones, but…” She shrugged. “Not exactly in the budget right now.”

Chuck leaned back in his chair, eyes fixed on the absent tits. “Tits are expensive, huh?” Chuck’s brow furrowed in thought. “How much are we talkin’?”

Poppy hesitated. “The good ones? A couple hundred, at least.”

Chuck let out a low whistle. “Damn. That’s a lot for a pair of fake tits.”

Poppy couldn’t help but laugh again, shaking his head. “You’re impossible, Chuck.”

Chuck smirked, but there was a glimmer of something softer in his eyes as he stood up. “Well, Poppy, I wasn’t gonna stick around with you looking like that but it worked out okay.”

Poppy smiled, taking the win. “Thanks, Chuck.”

As Chuck disappeared into his room, he stopped in the doorway, glancing back at Poppy. “Hey… Eddie or Stacy know about all this? That I know?”

Poppy shook her head. “No. Like you said it’s between us.”

Chuck’s lips curled into a mischievous smirk. “Let’s keep it that way for now.”

Poppy raised an eyebrow. “Why?”

Chuck leaned against the doorframe, his expression unreadable. “I’m getting an idea, MTF.…” Chuck smirked  “more to follow.” He waved a hand dismissively and disappeared into his room, leaving Poppy with a mix of curiosity and unease. Whatever Chuck had in mind, it was sure to be both interesting and, probably, rather crude.

***

Chuck nearly walked into Jilly when he emerged from the elevator scrolling his iPhone - she made zero avoidance effort. She couldn't have timed her visit worse, even if she'd tried. Chuck said 'everyone' was home, but to Jilly, that somehow sounded like bad luck - the hot, muscly hunk was out, and the rest were home  - Jilly loved the idea of a bit of rough. Just the idea of. As she rode to 8, Jilly inhaled the essence of Chuck – soap and a hint of a deodorant already unfashionable a decade ago.

Inside the apartment, Dave and Edward were hunched over a chessboard, while Stacy sat on the arm of the couch, furiously messaging someone.

At the sound of the doorbell Dave was off the sofa at the speed of a greyhound coming out the trap. “I was losing anyway,” he said, “three moves from checkmate.”

Jilly grinned, tossing her bag onto a chair. “You’re hopeless, Dave. No strategy, no patience.”

“Thanks for the pep talk, Jilly,” Dave replied, giving her a wry look as he grabbed an extra coffee mug for her.

The four of them settled into easy conversation over coffee, the mood light and familiar. Stacy half-listened, occasionally chiming in between text messages.

It wasn’t until Jilly stood to leave that she casually dropped the reason for her visit. “Oh, by the way,” she said, adjusting her scarf, “I came to invite Poppy over tomorrow night. Got some clothes I don’t wear anymore, thought she might want to take a look.”

Dave smiled, a crossdresser - even a part time one - could never have enough clothes.

“Monica will be there too. It’ll be like a little girls’ night - not the clubbing kind this time. More, you know, pillow fights in our bras and panties.”

Edward perked up instantly. “Pillow fights?”

Jilly caught his look and smirked. “Down, boy. I meant jokingly. You’d probably just spill your beer trying to peek in the window anyway.”

Stacy shot Jilly a sharp look, then turned to Edward, her tone indignant. “Oh, and I’m not invited?”

Jilly shrugged, pretending to think it over. “You wanna come? Sure. The more, the merrier.”

Stacy huffed theatrically, crossing her arms. “I don’t know… maybe I’ll just stay home.”

Edward rolled his eyes. “Stop being huffy. Just go, Stacy.”

Stacy’s faux pout melted into a smug little grin she couldn’t quite hide. Inside, she was thrilled. Jilly, Monica, and her plan to make it seem like Edward’s idea had gone off without a hitch.

“Well, if you insist…” she said, her tone light but triumphant.

Jilly chuckled, grabbing her bag. “Great. See you both tomorrow then, bye Poppy,” she said, pointedly using the name.

Dave nodded, trying to hide his nerves. “Yeah, sure. Tomorrow.” 

He made a call, switched to early shift and began listing the things Poppy needed to buy on his iPhone - hair remover, moisturiser… he closed his eyes, tried to remember what else had been on Stacy’s bathroom shelf. Dave and Stacy arranged to take the tram to Ivycross together. Edward suggested it was a perfect opportunity for Poppy, “Chuck has football practice, and you’ve only been outside the apartment once.”

Stacy lit up instantly. “A plan, Eddie! Love it. What do you think, Dave?”

Dave thought a while, it would be light outside, more chance of being made, more risky, more exciting… “well… Jilly did invite Poppy” he said slowly, his lips twitching into a small smile. “Jilly did not invite Dave.”

Dave discreetly let Chuck know the plan to avoid any accidental reveals.

“Don’t worry, I’ll steer clear. But Poppy is gonna owe me,” Chuck said with a sly grin.

“What now?” Dave asked warily.

Chuck’s grin widened as he pulled out a drug dealer wad of bills. “I figure you’ll need the cash if you’re serious about those breast forms.” He counted out six fifties and tossed them onto the table. “Here. A loan. Pay me back whenever you can.”

Dave blinked at the money, stunned. “Seriously?”

“Yeah. Call it my good deed for the year. Perhaps the decade. Next time I meet Poppy I wanna see her new tranny-tits.” Chuck  laughed kindly “her - have I got that right or are you still he?”

“She/her is perfect Chuck, if in doubt go by the clothes.” This was not the time for Dave to set him right about ‘tranny’

8 - Friends of Dorothy

Poppy asked Stacy if they could leave a bit earlier for Jilly’s.

“I’ve saved enough to get breast forms,” Poppy said, his cheeks slightly pink. “And I was hoping for some moral support.”

Stacy could barely contain her excitement. “Of course! Oh my god, Poppy, this is so exciting!”

The bell above the door jingled as Poppy and Stacy stepped into Friends of Dorothy. The shop was exactly as Poppy remembered it from his last visit—a cozy, brightly lit boutique with racks of glittering dresses, towering shelves of shoes, and a glass counter displaying every accessory from crossdresser through to drag queen could dream of - little wonder everyone called it THE crossdressers emporium in online forums.

Behind the counter stood Amanda, her short, vibrant pink hair as eye-catching as ever. She glanced up from her phone, her eyes lighting up with recognition. “Well, look who it is,” she said with a teasing smile. “Damn gurl, your name just slipped from my memory bank for a second - am I embarrassed or what?”

Poppy hesitated, his cheeks flushing. “Uh, it’s Poppy now.”

“I knew it! Poppy, cute, not toooo sparkly. Dave could not work with that look! You were in here a while back for a gaff, weren’t you?” Amanda’s grin widened. “So, how’s that working out?”

Poppy’s face turned a deeper shade of red. “Uh… good. It’s fine.”

Stacy snickered softly behind him, and Amanda shot her a glare and shook her head.

Amanda leaned on the counter. “Well, look at you. Moving up in the world, huh? So, what are we shopping for today?”

“Breast forms,” Poppy said, his voice barely above a mumble.

Amanda straightened, clapping her hands together. “Oh, honey, you came to the right place. Follow me!” She led them to a small display near the back of the store, where a variety of breast forms were neatly arranged by size, shape, and price. “Time to get all hands on, babe, go ahead - grope ‘em like you own ‘em.”

“These,” Amanda said, pulling down a box with a flourish, “are our top-of-the-line forms. They’re silicone, super realistic, and come with adhesive nipples.” She flipped the box open to reveal a smooth, lifelike pair, complete with interchangeable nipples of varying sizes and shapes.

“Adhesive nipples?” Poppy’s eyes widened at the sight of what looked like a serial killers trophy box.

“Oh yeah,” Amanda said, pulling out two. “See, you’ve got options. Like when you open your AirPods Pro box. No nipples for daytime - when a gurl wants to fly under the radar. These ones,” she held up a smaller, pert set, “are what I like to call ‘warm day nipples’- perfect for when a gurl is feeling all teasy in her summer dress. Is that even a word? Teasy?”

Stacy avoided giggling and leant in for a closer look. “It is now. What about those?” She pointed to a larger, more prominent pair.

Amanda smirked. “These bad boys? These are for when you’re hitting somewhere like Mirages.”

Poppy tilted his head. “What’s Mirages?”

Amanda looked genuinely surprised. “Are you even born? It’s the club for us gurls and their fans. Glitter, glam, and as much, or as little, attention you could ever want. Don’t tell me you’ve never been, Poppy.”

“Uh… no,” Poppy admitted, feeling slightly overwhelmed.

“Well, put it on your fucket list,” Amanda said, winking.

Stacy chuckled, pointed to the last pair. “You could hang a coat on those bad boys.”

“Please don’t,” Poppy shook his head. “I’m not planning to go that far.”

After some deliberation - and Stacy’s enthusiastic input - Poppy decided on the top-line breast forms. “Audience free event” Amanda said to Stacy as she closed the curtain behind her and Poppy. In the changing room, Poppy removed the forms from their box, he opted for the “warm day nipples,” thinking they’d be noticeable enough for Jilly, and Monica to notice but not over-the-top. “36C forms are just perfect for you.” Amanda enthused “and once they warm up they even feel real. Go ahead” She thrust her breasts at Poppy.

He groped Amanda with enthusiasm, they felt real in every way, the nipples hardened. 

Amanda gave a soft moan then burst out laughing “you’ll need hormones if you want a pair like mine.” 

Staring at his reflection in the mirror, he adjusted the forms until his new breast forms sat perfectly in his bra. The weight, the feel, the subtle tug on his bra straps as he swung side to side, even loose in his bra, it was surreal. With the adhesive it would feel like they were his! He smoothed his blouse over his overflowing bra, then stepped out to meet Stacy, who gave him a beaming smile.

The price tag ate up nearly all the money Chuck had lent him, but the lifelike quality was worth it. With the small amount of cash left over, Poppy added breast form adhesive and two more gaffs to his purchase.

“A gurl can never have too many gaffs” Amanda said as she bagged “are they are so easily lost or what?”

“Ready to turn some heads?” Stacy teased, when out of range of Amandas hearing. They walked out into the evening sunlight. Poppy couldn’t help but glance at his reflection in every shop window they passed, feeling both nervous and exhilarated.

They made their way to the tram stop, the air was filled with a mix of excitement and nervous energy. Poppy clutched his bag of gaffs and adhesive, feeling both exhilarated and self-conscious about the bold step he’d taken today. He couldn’t stop from checking his reflection in every shop window they passed. The slight tug of breast forms on bra straps was exhilaratingly unfamiliar.

“You’re going to walk into a lamppost if you’re not careful,” Stacy teased.

Poppy let a shy laugh escape, adjusted blouse across tits. “It’s just… how they tug at my bra and move as I walk. Do real breasts feel like that?”

“Not my little titties” Stacy chuckled. “You’d have to ask Monica or Jilly for a proper comparison.” On the tram, they took seats across from each other. While Stacy idly scrolled through her phone, Poppy occasionally let out small laughs. Stacy’s curiosity quickly got the better of her. “What’s so funny?” she demanded, lowering her phone. “Show!”

“Nothing to show,” Poppy replied, sounding casual, “just thinking about how Amanda glared at you earlier. You were this close to being put on the naughty step.”

Stacy huffed, though she couldn’t hide a smile. “She’s intense, huh? Naughty step - that some sort of a tranny euphemism?”

“Amanda’s serious about her store being a safe space,” Poppy said. “There are tales online about her shutting people down - we’re talking big time.”

That piqued Stacy’s interest. “Where online?”

Without thinking it through Poppy opened the Ashbourne LGBT website on his phone and handed it to her. “Here. There’s a whole section about…” He froze mid-sentence as Stacy’s expression changed.

“Poppy275” she said, her tone shifting to amusement. “Now, I wonder who Poppy275 is in the real world” She chuckled, holding the phone up like a woman presenting evidence in the Tranny Supreme Court.

Poppy’s heart sank. “Give that back!” he said, lunging forward to grab the phone.

Stacy was too quick. “Just how many other Poppys’ are there?” She leaned back, scrolling with one hand while fending him off with the other. “Oh, no way. You’ve been a member for years!” She tapped on ‘my pictures’ and let out a laugh when images loaded. “Look at this! These pictures are from three years ago. You were already at this long before Eddie saw you last month.”

Poppy felt his cheeks burn as he sat back, defeated. Stacy’s grin widened. “Oooh - Poppy is one slutty gurl,” she teased, unable to resist.

“How long have you known I call myself Poppy?”

“Since the first night, when I saw your username on your screen.”

“Can you please keep this between us?” Poppy asked, his voice a mix of pleading and mortification.

Stacy finally stopped scrolling and handed the phone back, her face as smug as a wife who had just discovered her husbands stash. 

“Alright, alright. I’ve had my fun. I won’t say a word… but my silence, my dear Poppy275, has a price.”

Poppy groaned. “What does that even mean?”

As they stepped off the tram and headed toward Jilly’s apartment, Stacy turned to him with a playful smirk. “Oh, you’ll see. Just remember, you need to keep me sweet, Poppy.”

***

When they arrived at Jilly’s apartment, Poppy felt his confidence waver just a little. Jilly greeted them both warmly, Poppy watched closely, expecting - well, more hoping - for her gaze to linger on his chest like the man’s had on the tram. Yet, there was nothing. Not a single comment, no flicker of acknowledgment about his new, more pronounced chest. How could she not mention it? Feeling a little cheated he wondered if should have gotten a bigger pair.

Jilly ushered them inside as if she were welcoming brandy smugglers to The Dockside Pub in the dead of night. Soon Jilly was deep in her closet, sorting through clothes she’d worn in a season or two. She handed Poppy items to go while Stacy, ever the critic, passed no-filter judgment.

“That’s a definite no,” Stacy said, waving off a sequin-covered top.

“Too flashy?” Poppy asked, holding it against himself. He took the evening not just as free clothes but as a fashion lesson - Stacy and Jilly had style in spades.

“Too everything,” Stacy shot back with a grin.

The rejected clothes were folded into a donation bag, while the rare items that both Stacy and Jilly approved were carefully folded and placed in Poppy’s bag.

“What size bra do you wear?” Jilly asked suddenly, catching Poppy off guard.

Poppy felt as if his ears might burst into flames. “Uh… 36. Amanda at the store said to get 36c.”

Jilly arched an eyebrow. “Well then,” she said, rummaging through the pile of lace and satin. “Here… I can - not believe I’m bra-buddying with a man.” She dropped a few bras into Poppy’s bag before pausing, her expression softening. “I’m so sorry, Poppy. That was… unforgivably rude.”

Poppy laughed, his embarrassment melting away. “Don’t be so precious about it. Dave says a man wearing a bra needs to develop a thick skin pretty fast.” Stacy was impressed by how fast Poppy distanced Jilly, and himself, from the thoughtless remark. 

Finally, Jilly dusted her hands and announced, “That’s it.” She flicked hangers back and forth, hesitated for a moment before adding with a wry smile, “Oh, no, I won’t be needing these ever again.” She pulled two fancy-dress costumes from the back of the rail and held them up for dramatic effect: a revealing cheerleader outfit and a risqué maid uniform. Michell felt a pang of desire that came directly from his inner Poppy.

Stacy burst out laughing. “You’re not wrong. No one needs to wear a slutty cheerleader or a slutty maid costume once let alone twice.” She paused, eyeing Jilly skeptically. “Actually, I can’t even imagine you wearing those once.”

Jilly snorted. “What can I say? I was younger and drunk.”

Closet tidying done, they settled in for tea, chatting and laughing until it was time to leave. Poppy glanced toward the bedroom. “I just need to get my bag from your bedroom,” he said quickly slipping away.

In the bedroom, he looked at the donation bag sitting by the bed. His heart raced as his eyes landed on the cheerleader costume perched right on top. It was his for the asking - only the embarrassment that would come from asking for the cheerleaders costume barred his way. 

It was so, so, so slutty and Poppy wanted it - so, so, so badly. 

He had an idea he could slip the cheerleader costume in his backpack - burry it under the other clothes like a covid hiding acorns in early fall - but it was too on-display - Jilly would definitely notice if it went missing.

9 - The Bean Scene

The trio gathered around a corner table at their favourite café, their mugs of coffee steaming between them. Monica leaned in eagerly, sensing there was gossip to be had.

“Alright, spill,” Monica said, her eyes darting between Jilly and Stacy. “What exactly did I miss at Jilly’s?”

Jilly took a deliberate sip of her cappuccino, savouring the buildup. “Oh, not much,” she said lightly, “only Poppy’s new look.”

Monica raised an eyebrow. “We’re talking of the breast forms?”

Jilly nodded with mock solemnity. “The very same. And let me tell you, Monica, they came with nipples.”

Monica almost choked on her drink. “No way.”

“Oh, yes,” Jilly replied, a wicked grin spreading across her face. “And not just any nipples - we’re talking summer and winter nipples here.”

Stacy groaned, hiding her face behind her mug. “Oh my God, I can’t believe we’re talking about this.”

“Why not?” Jilly asked innocently. “You were the one who approved them.”

Stacy’s face turned pink. “I didn’t approve the nipples specifically! Amanda at the store said the forms were the ones to go for, and I just agreed.”

Monica smirked, clearly enjoying Stacy’s discomfort. “Uh-huh. And you didn’t think, for even a second, that those little ‘glass cutters’ might draw some attention?”

“No! Jilly is being her usual overdramatic self” Stacy protested, she pointed at Monica. “They looked like those, they look realistic!”

“Personal!” Monica crossed her arms over her chest “Realistic? Or ‘realistic enough to turn heads? Come on, Stacy, you’re no innocent.”

Jilly jumped in, grinning. “Exactly. What’s next? Parading Poppy through the mall with those perky little things poking through her top?” Jilly was enjoying roasting Stacy.

Stacy wagged a finger at them. “You two are the worst! Seriously, such bitches sometimes.”

“It’s a gift,” Monica quipped, grinning.

Stacy leaned forward, her tone softening just a touch. “I’ll say the same to you as I told Jilly and Eddie - act as if they are invisible, he must be feeling really self conscious. You okay with that Mon? 

***

The apartment was quiet, Dave had the whole place to himself. He carefully transformed into Poppy. He slid the new breast forms into his bra, adjusting them until they felt just right. Sitting at the vanity Poppy began applying makeup. The constant switching - Dave - Poppy - Dave - Poppy - had one unexpected benefit, what once took hours now took a few minutes. With a final swipe of lipstick he moved onto lip-matching polish, alternating between a rather camp wrist waving  and blowing on nails. 

He turned side to side one last time - still thought the miniskirt could be shorter, the top tighter. 

He checked the time, it would have to do, he stepped into heels, let out a soft, almost disbelieving laugh that he was taking such care.

With Eddie safely at Stacy’s apartment time had come to show Chuck what his money was invested in. To keep it casual, he half-made coffee, he glanced at the door every few seconds. When he heard the clatter of keys, his heart raced. “Perfect timing, coffee Chuck?”

Chuck barely glanced at Poppy at first, but when he did, he froze mid-step. Chucks eyes took their own sweet time examining Poppy from the ground up. Poppy smiled, turned away to pour their coffee. Poppy could feel the heat of Chuck’s gaze through his 15 denier seamed stockings.  “Whoa,” he said, eyes flicking to Poppy’s chest as he turned. “Those are… uh… bigger than I thought they’d be.”

Poppy flushed, unsure if he should feel embarrassed or flattered. “Yeah, um, 36C. Amanda at the store said they’d be right for my body size.”

Chuck nodded absently, his gaze lingering longer than Poppy expected. “Well, she wasn’t wrong. Those puppies look... real.” He sat at the kitchen table, smirked. “So, what do they feel like?”

Poppy hesitated, the question catching him off guard. But Chuck had lent him the money, and the man had always been blunt. “Well,” he began, adjusting his stance nervously, “they’re silicone, so they’re soft. They warm up to body temperature after a while. And they, uh, move like real ones when you walk.”

Chuck tilted his head, sensing the chance for some fun. “Huh. That’s… something I guess only your boyfriend can confirm.”

“There is no boyfriend Chuck, crossdresser is not another word for gay.” Poppy laughed nervously. “You can feel for yourself if you’re curious.”

Chuck recoiled slightly, though his expression was more amused than horrified. “Nah, I’m good. But thanks for the offer, I guess.” He stood up, brushing past Poppy to grab a bottle of water from the refrigerator.

As he turned back, they were suddenly closer than either had anticipated - not the beyond punching distance but mere inches apart. Poppy looked up, his nerves taking over. A suicidal impulse gained control, he tiptoed and pressed his breast forms against Chuck. As if that were not dangerous enough a quick kiss to Chuck’s cheek followed. “Thank you, for these Chuck” Poppy said softly, his voice trembling with sincerity. “I don’t know how I can ever repay your kindness.”

Chuck froze, pushed Poppy away, “Get the fuck away from me you… CUNT.”  If anger had a colour it would be the colour Chuck’s face chameleoned into. “This close, this close! is that really too hard to remember?” Chuck held out what Poppy imagined to be his punching arm.

Poppy readied for a physical reaction, but Chuck stepped further away into the doorway, scratching the back of his neck. “Uh… yeah. Just pay me back what you can each week, like we said.” He glanced at Poppy, then had an idea, Stacy was forever on his case, two birds one stone - “If you’re really that grateful, you could… I don’t know, clean my room or something. But not when I’m home. Or when the other two are here.”

“I’m sorry, for the hug and doing that…”

“Nothing happened, nothing right?” Chuck either smiled or readied to bite.

Poppy’s gratitude bubbled over. “Deal. Saturdays while you are at football.” Poppy laughed, Chuck snorted. “Yeah, well, don’t forget who’s doing who a favour here, Poppy.”

Sitting alone in his room he could feel himself colouring, he quietly said “what the fuck was that about Poppy?” Dave was not gay so why had he flirted? And there was no pretending he hadn’t. Dave tossed the wig on his bed, roughly removed his makeup, this was exactly why crossdressing was a bad, bad, bad idea. Crossdressing was about looking slutty NOT being slutty Dave told himself. 

Dave felt that old feeling of shame and regret that came just before a need to purge. He double bagged everything ready to put in the next buildings dumpster. Took the elevator to ground, heaved the bag over the side, his hand locked on as tightly as a man-overboard gripping a lifebelt. Try as he might Dave could not let go. “If not for the cost of the breast forms I would have” Dave told himself as he replaced Poppy’s clothes in the closet.

***

Stacy and Edward came back late from a night out. Edward, as usual, was asleep almost the moment his head hit the pillow. Stacy, wide awake, wandered the apartment, annoyed by her own restlessness. Passing Dave’s door, she noticed light shining from underneath. Curious, she knocked lightly.

“Poppy? I’m making tea. You want some?”

“Sure, why not?”

When Dave appeared in the kitchen, Stacy raised an eyebrow and smirked. “I expected Poppy,” she teased, leaning against the counter.

“Poppy only visits when Chuck’s out.”

“Talking of Chuck, I noticed the apartment is smelling sweeter recently, someone fumigate his room?”

“I cleaned it while he was at soccer - it made sense - cost and benefits.” Dave said.

Stacy raised an eyebrow, chose not to press further. Instead, she shifted the conversation to herself. “He makes me mad sometimes, Eddie, falls asleep right after sex. It’s so unfair, sometimes, I just want... more, you know?”

Dave burst into laughter. “I’ll take your word for it.”

“Behave, I’m not talking about more sex,” Stacy joked, grinning. “Try acting like Poppy for a moment.”

“Okay, Poppy’s here in spirit if not clothes.” Dave swiped a teaspoon over himself like a magician.

Stacy tilted her head, thinking. “Well, maybe it’s time Poppy stepped out a bit more. What about on a rest day? No Chuck, no Eddie. Just Poppy and me.”

Dave hesitated, already feeling the nerves creep in. “Daytime’s a bit too big of a step.”

“I’ll chaperone,” Stacy interrupted confidently. “We’ll grab lunch at a café. You won’t be alone.”

Dave considered it for a moment, then nodded reluctantly. “Okay... let’s do it.”

Stacy Cheshire-catted a while. “Hey,” she said suddenly. “How’s the voice training coming along?”

Dave switched into what he called femvoice . “It’s... okay, I guess. I’ve been using this app. It’s like Duolingo for crossdressers.”

“Who said that” Stacy said, sitting up straighter, genuinely surprised, suitably jaw dropped. The voice was light, smooth, and so convincingly feminine that for a moment, she barely recognised it as Dave. “Oh my God,” she said, eyes wide. “That is literally incredible. You sound nothing like yourself.”

Dave grinned sheepishly, feeling a rare spark of confidence. “Thanks. It’s still a work in progress.”

Back in Edward’s bed, Stacy found herself unable to sleep. But this time, it wasn’t because of Edward’s immediate post-fuck-coma. Her mind raced, forming a plan - one she intended to keep entirely to herself.

As the plan solidified in her head, a mischievous smile tugged at her lips. Only then did sleep finally take over.

10 - Lunch in Ashminster

Dave reflected on the conversation with Stacy. He felt a need to test his voice training on someone unexpecting, someone who knew him. Deciding on a suitable victim he picked up his phone. “Hi, Jilly. It’s Poppy.”

There was a brief pause before Jilly responded, her voice warm with recognition. “Poppy, is that you? I did not recognise your voice for a second. What’s new with you?”

Poppy smiled because the app said to. “I just wanted to thank you for the clothes, sorry for not calling sooner. They’re... really nice, and it means a lot.”

“Oh, I’m so glad you like them,” Jilly replied. “Did everything fit?”

“Uh-huh, the pencil skirt is to die for…”

“How about…” Jilly paused leading him along like little bow peeps lamb for a second “the fancy dress costume, what was it - a maid costume?”

Poppy’s voice slipped, Dave said. “Oh... Jilly, I’m so sorry about the maid costume. I shouldn’t have taken it without asking…”

“Relax,” Jilly interrupted gently, her tone kind. “You don’t have to apologise. Honestly, making such a big show of pulling those costumes out was a bit of a test.”

Poppy was back. “A test?”

Jilly chuckled. “I’ve read about crossdressers and skimpy costumes, you know. I used them as bait, and it looks like I caught myself a crossdresser.”

Poppy couldn’t help but laugh, nerves easing. “You’re not mad?”

“Mad? Of course not,” Jilly said warmly. “We can keep this between us. And as for the cheerleader costume, don’t worry, it’s safe with me.” There was a pause, then Jilly added with a playful edge, “Maybe you’ll swing by sometime and check if it fits.”

Poppy blushed but smiled. “Maybe I will.”

“Good,” Jilly said with a laugh. “Talk soon, Poppy.”

***

Jilly paced her living room, phone in hand, unable to stop thinking about her conversation with Poppy. His voice had been incredible - smooth, feminine, and utterly convincing. She dialled Stacy, who answered on the third ring.

“Hey, Jilly, what’s up?”

“You didn’t tell me Poppy’s voice was that good,” Jilly said without preamble.

Stacy chuckled. “Oh, you mean Dave’s voice app? Yeah, he can say a few things. It’s getting there.”

“A few things?” Jilly’s voice rose an octave. “We talked for twenty minutes, Stacy. Twenty. Minutes. And there wasn’t a single slip. I swear, you’d never know!”

Stacy let out a low whistle. “Wow. I mean, I knew he was practising, but... twenty minutes? That’s impressive.”

“I kept forgetting I was talking to Dave. It was all Poppy.”

Stacy grinned to herself. “Well, Poppy is meeting Edward lunch tomorrow.”

Jilly blinked. “Lunch? What lunch?”

Stacy froze, realising she’d let it slip. “Oh, uh... just a casual thing. I’m taking Poppy out for pizza, the usual place. No big deal.”

Jilly hid her excitement. “I’ll expect a word for word report. Have fun.”

Jilly speed-dialed Monica. “You’re not going to believe this,” Jilly began as soon as Monica answered.

Monica chucked. “Got goss?”

“Yes,” Jilly confirmed, her tone brimming with intrigue. “Stacy’s taking Poppy to lunch tomorrow. Our pizza place, they are meeting Edward. We are NOT invited!”

“He has lunch at one” Monica perked up. “We crashing?”

“Absolutely,” Jilly said. “But play it cool. Stacy doesn’t need to know we’re coming.”

“Done,” Monica replied, already planning her outfit. “This is going to be fun.”

***

Stacy arrived at Dave’s apartment in plenty of time. Poppy was already dressed - black wig, breast forms with discrete nips, stylish floral blouse, a pencil skirt, white sneakers. He looked nervous but ready.

“You look great,” Stacy said, giving her a quick once-over. “Head to toe lunch break secretary style, that will be like a cloak of invisibility in lunchtime Ashminster.”

“Thanks,” Poppy said, smoothing down his skirt.

With time to spare, they decided to window shop on the way. Poppy relaxed a bit as they wandered, occasionally stopping to admire shoes or accessories. Stacy kept the conversation light, making sure Poppy felt at ease.

***

They arrived at the pizza place first and settled into a booth by the window. Poppy fidgeted with napkin, nerves returning.

“Deep breaths,” Stacy said. “You’re doing amazing.”

Edward and Alan arrived shortly after. Edward greeted them with his usual confidence, made the introductions and slid into the booth next to Stacy, while Alan sat across from Poppy.

The server brought menus and water, and they started chatting about movies and work. Alan seemed friendly and relaxed, Poppy found herself enjoying the conversation.

Just as the server took their order Jilly and Monica walked in.

“Well, well,” Jilly said, her eyes twinkling as she spotted the group. “What a coincidence!”

Stacy groaned softly. “Oh no.”

Poppy turned, eyes widening as Jilly and Monica neared. “Hi,” he said nervously.

“Mind if we join you?” Monica asked, not waiting for an answer before sliding into the booth beside Alan. Jilly took the remaining spot next to Poppy, who was now sandwiched between her and Edward.

***

“So, Poppy,” Jilly began, “you’ve been keeping busy, huh?”

Poppy blushed. “Uh, yeah. Thankful it is my rest day. Stacy had a day free and here we all are.”

“Meeting up like this, coincidence or what,” Monica chimed in, grinning. “You look amazing. Who’s your stylist?”

Stacy shot Monica a warning glance. “Don’t tease her.”

Alan, oblivious to the teasing, complimented Poppy’s hair. “It really suits you. Great choice.”

Poppy murmured a thank you, confidence growing slightly, though he couldn’t shake the feeling that Jilly and Monica had an agenda.

As the server started topping off coffee cups Edward and Alan had left for the office. Poppy went to freshen his makeup.

“Talking about you two gate crashing can wait”  Stacy said. "You leave first. Poppy's ready to be cast adrift."

Jilly raised an eyebrow. "You sure?"

Monica smirked. “If what I just witnessed is anything to go by he’ll be fine, next time Stacy, we pick the venue."

Jilly and Monica said their goodbyes, leaving Stacy and Poppy alone.

"Okay, Poppy," Stacy said as they stood outside on the sidewalk. "I’ve got things to do, enjoy the rest of your day."

Poppy blinked, panic flashing across her face. “Wait, how will I get home? I can’t walk across town like this!”

Stacy chuckled, leaning in to kiss Poppy on the cheek. “You’ll be fine. Trust me.”

“But Stacy”

“You’ve managed just fine for the past couple of hours. You made it here, monopolised Alan - a stranger, for half the meal, and you didn’t miss a beat.”

Poppy opened her mouth to protest, but Stacy held up a finger, teasing her. “And don’t think me and the girls didn’t notice you flirting with Alan… and the wine waiter.”

“What? I wasn’t” Poppy stammered, cheeks turning crimson.

“Oh, please!” Stacy laughed. “Ooh, no more wine for me, I won’t be able to control myself, followed by a casual forearm touch? Classic. You even leaned into it with Alan. Slutty Poppy!”

“Feminine gestures Stacy, I wasn’t trying to flirt!”

“Sure, you weren’t,” Stacy teased, winking. “Look, you’ve had just the right amount of wine, and you’re dressed like the cutest secretary in town. Trust me, no one’s going to give you a second look on your way home. Browse, have a coffee, enjoy - you’ve so got this.”

Poppy sighed, nerves settling just a bit at Stacy’s confidence. “You really think so?”

“Know so, now, go enjoy the rest of your day, and I’ll see you Thursday when I come over to cook dinner. Twenty minutes walk from your closet  and you’re going to love every second.”

Poppy took a deep breath, glanced at her reflection in the window, straightened her blouse, undid one more button. “Here goes nothing.”

***

Poppy watched Stacy’s figure disappear into the crowd, aloneness hit like a wave. He felt an all consuming urge to run after her, to call her back. But Stacy was right - Poppy had handled himself faultlessly so far. He adjusted his purse and took the first step. Every glance in his direction seemed to linger a fraction too long, every one felt like scrutiny. Was his wig crooked? Was his makeup smudged? Poppy’s mind raced, imagining every possible reason someone might stare - except the fact he was a man wearing a skirt and blouse. But as shop window after shop window passed with no incident, his confidence grew. By the time he neared the mall, the lure of the bright windows and bustling shoppers was too strong to resist. He turned into the entrance, thankful he had not worn heels that morning - clicking on tiles would have had heads turning.

***

Poppy drifted shop to shop, he noticed how the hologramness of his reflection in the glass made him look like a day-tripper from a different dimension. A sweater in one window caught his eye, and he imagined himself wearing it. He returned smiles of passing strangers, savoured the thrill of undiscovery. Confidence suitably buoyed he wandered toward the food court, feeling bold enough to order a coffee and sit at one of the open tables.

He had just taken her first sip when a small voice piped up nearby.

“Mummy, why is that man wearing a skirt like yours?”

Poppy froze, the cup trembling slightly in his hand.

“Shh!” the mother said, clearly flustered. “Don’t be rude to that lady.”

“But it is a man, Mummy” the child insisted, staring at Poppy with wide, curious eyes.

The mother leaned closer to her daughter, whispering harshly, “That’s enough! You apologise this instant!”

Poppy’s face burned as the mother turned to her, an awkward smile plastered across her face. “I’m so sorry. I don’t know where kids get these ideas.”

“It’s... it’s fine,” Poppy managed, forcing a smile.

The mother herded her daughter away, still scolding the child. Poppy steadied her breathing. A few minutes later, Poppy noticed a man leave the counter, his eyes catching hers briefly, he smiled and walked over.

“Mind if I join you?” he asked, gesturing to the empty seat across from her.

“Uh, sure.”

He sat down,“I thought I recognised you, from the mall - we smiled - in the mall.”

Poppy’s heart raced, her fight-or-flight instinct on high alert. “Oh, uh, did I? I guess I was just... being polite.”

The man chuckled, leaning slightly closer. “Well, it made my day. Are you from around here?”

Before Poppy could answer, a familiar voice cut in.

“Poppy? Is that really you?” Jilly appeared beside the table, her expression one of surprise despite trailing Poppy since lunch. “Wow, what a coincidence running into you here!”

Poppy smiled with relief. “Jilly! Hi!”

“Mind if I join?” Jilly asked the man sweetly.

“Uh, sure,” he said, visibly deflated by her arrival.

Jilly let the man continue his clumsy pickup attempts, offering Poppy a reassuring smile now and then. Poppy, desperate for an out, said “actually, I’m waiting for my boyfriend. He should be here any minute.”

The man’s expression soured slightly, and he stood. “Well, it was nice meeting you.”

Before he was even out of earshot, Jilly said. “Boyfriend, huh?”

Poppy groaned. “Desperate situations - desperate measures.”

Jilly laughed. “And who might this mysterious boyfriend be? Alan from lunch, perhaps?” Poppy blushed deeply, laughing despite herself. Jilly’s tone turned teasing. “By the way, are you ever coming by to try on your cheerleader costume?”

Poppy peeked at her from between her fingers. “I don’t think it’ll fit. Isn’t it the same size as the maid costume?”

Jilly’s smile widened. “Oh, so you did try the maid costume. Knew it.”

Poppy blushed furiously, but Jilly only laughed kindly. “You’ll need the corset that goes under both. Tell you what - why don’t you come over one morning, stay for lunch, let’s work out a day when you’re on rest?”

“I would like that Jilly” he said softly.

“Perfect,” Jilly said, standing. “Come on, let’s head home… I mean if you are finished picking up strange men that is.”

***

As Poppy and Jilly strolled away from the mall they fell into easy conversation. “You seem different this afternoon, since the food hall” Poppy said, glancing sideways at Jilly.

Jilly raised an eyebrow. “Different how?”

Poppy shrugged, hesitating as he searched for the right words. “Just… different. Like us being alone has let you relax in some way.”

Jilly laughed softly, but there was a hint of something guarded in her tone. “A lazy lunch and a glass of wine will do that,” she said lightly.

Poppy shook his head. “It’s more than that. Almost like… without Stacy here, you’re, somehow, more yourself.”

Jilly’s pace slowed for a beat, and Poppy felt her studying him out of the corner of her eye. When she finally spoke, her tone was carefully neutral. “What has Stacy told you?”

“Nothing,” Poppy said quickly. “It’s just… I see the way Stacy looks at you when she thinks no one is watching.”

Jilly stopped walking, her shields visibly snapping into place. “That everything?”

“And I notice it is no one-way thing, that’s everything,” Poppy assured her, his voice calm.

For a moment, Jilly said nothing, then she let out a low sigh. “It’s not just the clothes with you, is it? You notice things. Stuff most men wouldn’t.”

Poppy smiled, a little sheepishly. “I get called observant sometimes.”

“Observant?” Jilly let out a small laugh, shaking her head. “You’re like Sherlock Holmes. Do me a favour and try not to solve every mystery you see, okay?”

“Only the important ones?” Poppy teased.

They walked on, a gentle silence settling between them. But as much as the conversation had veered away, Poppy couldn’t shake the sense that there was more to Jilly and Stacy’s history than either of them would ever openly admit.

Jilly glanced at Poppy, she didn’t know why, but she felt an urge to tell him everything - things unsaid for a long time. She broke the silence with a hesitant laugh. “You know, there’s something about you, Poppy. I feel like I could talk to you about stuff I don’t usually talk about.”

Poppy waited for her to continue.

“Okay, here we go…” Jilly took a deep breath. “Stacy and I… lived together for a couple of years.”

Poppy’s eyes widened slightly, but he stayed silent, sensing there was more to the story.

“Stacy left,” Jilly said, her voice softer now. “Said she wasn’t sure if she was just... experimenting.” Jilly paused, glanced away as if searching for the right words. “And then Edward came into the picture, swept her off her feet, and that was that. Now I’ve lost her forever.” 

Jilly wished words had an unsay option like emails - Now I’ve lost her forever - why the hell had she said that? 

Poppy gave Jilly's hand a gentle squeeze. “That must be so hard. I mean when one partner moves on like that.”

Jilly turned the hand squeeze into a holding of hands that lasted for the hundred or so yards to the building. She thought what she would make them for lunch when he visited, thought Poppy will do just fine.

***

“You must come in for some tea” Poppy said “I never have guests."

Jilly hesitated for a moment, but curiosity - and the chance to spend more time alone, assessing Poppy ‘in the wild’ without Stacy sealed the deal. “Sure, tea sounds great.”

They made their way upstairs, and Poppy unlocked the door, pushing it open. The sounds of DOLL$BOXX drifted out from the kitchen. As they walked into the kitchen, Jilly froze in her tracks.

Chuck was sitting at the table, seven-tenths empty mug in hand, flipping through a weight-training magazine. His gaze flicked up to the doorway, and Jilly braced herself for the explosion. She knew Chuck’s reputation for bluntness, and after Stacy’s repeated warnings, she fully expected Chuck to lash out at seeing Dave crossdressed.

But instead, Chuck simply smiled. “Hi, Jilly. Hey, new outfit Poppy. Been somewhere exciting?”

Poppy leaned casually against the counter, “we’ve been out for lunch,” he replied, shooting Jilly a smirk. “Then I get hit on at the mall.”

Jilly’s jaw nearly hit the floor. She tried to process what she was seeing and hearing. LGBT-phobic Chuck whom Stacy had insisted knew nothing about Poppy was not only aware of her but seemed completely unfazed. No, more than that - Chuck was behaving friendly!

“You get his number?” Chuck teased with a grin, taking a sip of his coffee.

“Nope,” Poppy replied with a playful toss of her hair. “Didn’t need to. He got the hint when I said I was waiting for my boyfriend.”

“Classic cock-block” Chuck let out a hearty laugh, shaking his head. 

Jilly finally found her voice, though it came out all croaky. “Wait, what exactly is happening here? Chuck, you know about Poppy?”

Chuck shrugged, looking amused by her reaction. “ ’Course I do. Poppy lives here, doesn’t she? Figured it out weeks ago.”

“Weeks?” Jilly stammered, her mind reeling.

“Yeah,” Chuck said, setting down his mug. “I mean, it was kind of obvious. Came home early one day, saw Poppy walking around. It’s not a big deal. She’s paying rent, does her thing.”

Poppy shot Jilly a conspiratorial wink as she busied herself with the kettle. “Chuck’s been a real sweety.”

“Sweety? Fuck you” he feigned anger for Jillys benefit but winked at Poppy. “Now, if you two are making tea, pour me another cup, would ya?” Poppy had instigated a prank ten times more exciting than his intended prank on Eddie and Stacy - Poppy was acing it.

The moment Jilly stepped into the elevator, she pulled out her phone. The second the call connected, she launched into a breathless tirade. “Stacy, you will not believe what just happened!”

11 - Back into the Wild

Poppy was as restless as a Meerkat, he had walked the city streets alone and now the apartment felt claustrophobic. He needed to go - anywhere. He thought over what Amanda at Friends of Dorothy said and changed into his miniskirt and the little pink crop top. He worried his breast-forms might just plop out of such a revealing top - right there on the pavement - but a few star jumps proved that was not going to happen. Chuck shouted for Poppy stop “you got dancing hippofuckingpotamuses in there?"
Poppy lingered in front of the mirror, his hands trembling as he made minute adjustments to his eyeliner. His reflection stared back, there was nothing more to do apart from go out. 

This was it.

Sliding AirPods in, he selected the playlist with a flutter of anticipation and dread. He’d named it “Ladyboy” on a whim - every song title, bar one, was ‘Ladyboy’ - created the playlist half-joking, half-daring himself to ever need it. Tonight, it was neither. He pressed play, and Lindemann’s gravelly voice filled his head ‘black lips, brown eyes, wet flesh, good thighs… ladyboy… he is my toy boy…’ 

The elevator felt claustrophobic, each second passed like an hour as he descended. He could feel his pulse thrumming in time with the bassline. Every mirrored surface felt like an accusatory gaze, but Lindemann’s lyrics seemed to whisper back, "Own it." The moment the doors slid open to the lobby, Poppy stepped forward, bracing himself against a tidal wave of second thoughts. The first notes of Nemophila’s Back Into The Wild surged through his ears as he pushed the glass door open to the street. 

The night air hit him, crisp and bracing, as if daring him to step further. He hesitated, but the song's energy wouldn’t allow him to stop. Sterling Street waited ahead, Poppy held his head high, his nerves still bubbling beneath the surface but kept in check by the steady stream of music, Redi Bōi thrumming in his ears with a gritty determination that seemed to infect his stride.

Heels clickety-click-clicking, Poppy crossed the intersection, by the time the Long Tall Texans gave way to the Pink Street Boys, a spark of exhilaration began to ignite in his chest. The punk edge of Armitage Shanks tipped the balance entirely, Poppy felt invincible. The music wasn’t just a soundtrack; it was armour.

He was back into the fucking wild.

***

Partway along Sterling Street the playlist looped one more time. It was in sight - the neon sign - Mirages. Poppy felt the power of the sign drawing him ever closer - like a version of gravity that affected only crossdressers. 

AirPods to charging case.

He checked his reflection in the darkened shop window near the club and began a pre-club checklist beginning with a wriggle: breast forms snug under pink crop top - check, miniskirt swishing across thighs - check, heart beating 1000 times a minute - check. 

“If you can make it here you can make it anywhere” Poppy told himself as he walked in. 

He expected a dance club, pulsating bass, writhing bodies. 

He got a club that was intimate, a scattering of tables, a small dance floor, soft lighting, and a long bar where a handful of customers chatted quietly. Poppy hopped onto a stool a safe distance away, the bounce of his breast forms reminding him of their presence. Behind the counter, a striking woman - "Doris Demontré” the name tag announced - heavily made-up and with a platinum blonde wig so big and bold  Poppy thought she must have scalped a drag artist.

“Well, don’t you look just fabulous!” Doris said, her voice pure tranny purr. She leaned on the bar, her crimson lips curving into a grin. “Pink, bold for a first-timer at Mirages. WE like bold.” Said the gurl who seemed not to know unglittering clothes even existed.

Poppy smiled shyly, tucking a strand of his long black wig behind his ear. “I’m Poppy by the way, Poppy Pérez.”

“Oh, Poppy honey, the pleasure is all mine,” Doris slid a martini toward him with a dramatic flourish. “I just know we’re going to be thick as thieves by the end of the night.”

Poppy sipped his drink, the tang of lime and gin steadying his nerves. They chatted easily, Doris punctuating ever more unlikely stories with animated gestures. She was magnetic, her laugh infectious, and her confidence contagious.

“So,” Poppy asked after a while, “how long have you worked here?”

“Seven months,” Doris said, leaning casually against the bar. “Which is a lifetime in Mirage years, trust me. Don’t get me wrong honey, Wilma Wilkinson, the owner, is amazing. But not everyone takes to the whole ‘crossdressed in public’ job, you know? It’s a lot for some people. Mind you, others” she gave Poppy a pointed look “fit right in.”

Poppy accepted the look as a compliment and smiled, a warmth spreading through him that had little to do with the alcohol, he liked her - a lot.

After finishing his drink, Poppy decided to call it a night. It was still early and yet the chill of the night air contrasted sharply with the club’s warmth. He took a deep breath, shop windows lining the darkened streets reflected his silhouette just perfectly. Poppy took the scenic route home.

***

Wilma Wilkinson, perched on the stool Poppy had vacated, chatting with Doris Demontré. Wilma, dressed in a sleek black jumpsuit with glittering belt, watched Doris mix a drink. “So, what’s the story with the newbie you were chatting with earlier?”

Doris, dressed silver hot pants and  clingy top, shrugged, perfectly lined lips curling into a smirk. “Names Poppy, clearly a new gurl. Cute, but…” She trailed off, tossing a glance over her shoulder to make sure no one was within earshot. “A little slutty for her first time here, don’t you think?”

Wilma arched a perfectly groomed eyebrow, her lips twitching with amusement. “So says the barmaid wearing silver hot pants,” she shot back, voice dripping with playful sarcasm.

Doris froze mid-pour, then burst into laughter, the sound rich and unapologetic. “Okay, you got me,” she admitted, placing the drink on a tray and turning to face Wilma.

Wilma leaned forward, resting her elbows on the bar. “Now tell me, Doris,” she said, her tone shifting slightly. “Was that a criticism or a compliment?”

Doris hesitated, then grinned. “Maybe both,” she said with a wink.

Wilma laughed, stood, smoothed her jumpsuit. “Good answer.” With a parting chuckle she catwalked toward the back of the club.

12 - Fight Night

Tension settled over the apartment like a storm cloud as Stacy started cooking. By the time all three flatmates - Dave, Edward, and Chuck - gathered around the dining table with Stacy, Dave, meeting her for the first time since the prank on Jilly, couldn’t shake the feeling that something was brewing.

“So,” Stacy began, breaking the silence, “Jilly mentioned she stopped by the other day. Said you and Poppy had some fun, Chuck.”

Chuck looked up from his plate, calm but wary. “We did indeed, what about it?”

“Oh, surprised you thought it was so funny,” Stacy said, her tone sharp enough to cut a red onion. “Using Poppy for your amusement like that. Real classy.”

Fork mid plate to mouth Chuck paused, still calm. “Using Poppy? It was a joint effort. And do you think we’re not allowed to have fun?”

Dave froze, his fork halfway to his mouth. Edward kept his head down, focusing on his food. He knew from experience baiting Stacy “in one of her moods” never ended well.

Chuck continued, his voice steady. “You’ve been pushing Poppy into situations she’s barely ready for. What about that lunch you set up, abandoning her in the city centre, Huh?”

Stacy’s eyes narrowed, she picked up on Chuck’s choice of pronouns, hiding her surprise, she followed his lead. “I’m helping her build confidence, not treating her like a toy. And don’t think for a second I do not know all about making her clean your room?”

Chuck shrugged, only Edward could have told Stacy that. Game on! “That’s different. It’s a private arrangement Poppy and I agreed on.”

Stacy turned to Dave, her voice rising. “Is that true?”

Dave nodded. “It is Stacy. It’s okay to tell her Chuck.”

Chuck sighed. “Fine. I lent Poppy money for something she really wanted, and we agreed she’d pay me back in part by doing some chores. That’s it. It’s not like I’m the one blackmailing her to clean.”

Stacy’s jaw tightened. “Blackmail? What are you talking about?”

Chuck glanced at Edward, who suddenly looked very interested in the remnants of his dinner. “Why don’t you ask your boyfriend,” Chuck said, his voice laced with sarcasm.

In search of a fall guy Stacy rounded on Edward, he shifted uncomfortably in his seat. “What’s he talking about, Eddie?” Stacy’s glare fixed him in place. 

Eventually, he sighed and admitted, “Fine. I made Poppy clean the apartment - and my room - in exchange for not telling Chuck about her, but that’s history now.”

Stacy’s face turned red with anger. “Are you serious? While I’ve been helping Poppy build confidence, you’ve been blackmailing her? Un-fucking-believable.”

Edward stood, trying to calm her down. “Stacy, it’s not like that anymore”

“Don’t,” she snapped, cutting him off. “You don’t get to justify this.”

She stormed past him, grabbing her coat from the rack. Edward trailed behind, his voice pleading. “Stacy, wait…”

“You’re supposed to be my supportive boyfriend, Edward! Not some manipulative jerk making Poppy’s life harder! How dare you!”

Stacy stormed out, her coat in hand. Edward followed, “Stacy, wait—”

But she was already gone, slamming the door behind her.

In the silence that followed, Chuck leaned back and exhaled. “Well, that was fun.”

Dave gave him a look. “You didn’t have to stir things up.”

Chuck shrugged. “Maybe not. But she needed to know the truth.”

13 - The Corset Virgin

In Jilly’s apartment, Poppy stood in the bedroom, cautiously eyeing the black satin waist-training corset in the way a grizzly bear might eye a moose. If a black shiny satin could be described as opalescent then the corset was opalescent. Its wide, rigid shoulder straps and heavy boning made it look both beautiful and intimidating, Poppys inner Poppy chanted; put it on - go on, go on, put it on, go on…

“This is what will get you into the cheerleader uniform, and don’t worry if you’ve not corseted before, I’ll help you.” Jilly said, holding it up the corset with a smile.

“Alright, but be gentle with me.”Poppy barely hesitated before undressing down to his gaff, his eyes locked on the corset.

Jilly’s laugh was soft, confident. “Oh, Poppy, gentle is so not what this is about. Corseting is surrender. Hold still.”

As Jilly clipped the busk together Poppy felt a flicker of excitement. The fabric felt soft and cool against his skin and had the feint smell of new clothes. But nothing prepared Poppy for the sensation of the boning pressing firmly against his body. It was unlike anything he had felt before.

Jilly began working the laces - top to waist, bottom to waist. All the while her fingers maintained the sort of steady tension on the lace loops that a rider would use on a wayward stallions rein. The first pass drew a small gasp from Poppy as the corset began to hug him like a needy girlfriend. “Wow, that’s… snug,” Poppy managed while sucking in his stomach even more.

“It’s supposed to be,” Jilly said, voice low and steady, feelings hint of satisfaction. Little by little she worked the laces tighter - top to waist, bottom to waist - Poppy as if he slipped a little further under Jilly’s control with each pass. “Trust me, Poppy, you’ll love the shape it gives you. Ready for the final pass?”

Poppy steadied herself. “Do I have a choice?”

Jilly worked the laces - top to waist, bottom to waist this time gaining mere millimetres - single figure millimetres at that. Poppy let out a soft exhale surrendering body to the control of corset. He looked at his reflection, a dramatic curve lead to his waist. With the laces tied off Jilly situated Poppy’s breast forms into the cups and adjusted the wide, rigid shoulder strap.

Poppy stood, fingertips exploring the slick satin, tracing the metal bones of the corset, marvelling at how it had transformed his figure. And the fabric… so innocently thin and so delightfully shiny and yet with a grip of steel. He had read all about crossdressers fantasies and always considered the fuss they made over corsets was laughably far fetched. But here - live from inside his own corset - he realised mere words did not have the capacity to describe what wearing a corset truly felt like “This is… amazing. I feel like I can’t bend at all.”

“That’s the point,” Jilly said, stepping back to admire her handiwork. Her voice softened, taking on a slightly possessive edge. “The first step to giving up control is letting the corset do the work. It holds you, shapes you reminds you that you’re not the one entirely in control.”

Poppy shivered slightly, unsure if it was from the constriction or the thrill of what Jilly was implying. As Jilly tossed a pack of sheer black stockings onto the bed, her smile widened. “Here,” she said. “These will complete the look.”

For Jilly, lacing Poppy into the corset she had crafted for him felt like seizing a fragment of the power that Stacy had once exclusively wielded over her pet crossdresser. 

Poppy, in turn, had zero desire to resist the intoxicating attraction of surrendering to Jilly. The corset made reaching his toes impossible. “Uh… we have a problem,” he said, laughing.

“Oh, for heaven’s sake,” Jilly said, rolling her eyes playfully. “Sit down. I’ll do it.”

Poppy perched on the edge of the bed, watching as Jilly knelt in front of him and carefully rolled the stockings up his legs. The sensation of sheer stocking sliding over hairless skin sent a shiver up Poppy’s spine and set off other feelings inside his gaff. 

“There,” Jilly said “fasten your suspenders while I go get the costumes.”

Poppy fiddled with the garters, feeling both excited and a little self-conscious. When Jilly returned holding the two costumes - cheerleader and maid - Poppy looked up, unsure.

Jilly smiled asked if he was getting accustomed to being corseted, Poppy was, said it felt exhilarating to be held so tightly “now that the shoulder straps are tightened there is no way I could release myself.” He demonstrated by reaching as far back as possible. “See?”

“You like being corseted by a strong willed woman… Is that the best or what? Jilly tested - Poppy didn’t miss a beat before agreeing it was! 

“What is it to be - cheerleader or maid - which one first?”

 “Cheerleader, no, maid, no… I can’t decide,” Poppy admitted. “You pick.”

“I was thinking cheerleader first as well, but, you put the cheerleader costume on, then what?  We don’t have pompoms and who could you cheer even if we did. I guess the maid costume could involve some role play…”

“I’ve decided, maid.”

“Because it is scandalously short?” Jilly teased “now, who was it told me you like to dress a little slutty” Jilly tapped her chin dramatically while holding up the maid costume. “Might that have been Stacy?”

A few minutes later, Poppy stood in front of the mirror, tugging nervously at the hem of the impossibly short maid costume. The ruffled apron and lacy Alice band completed the look.

Jilly stepped back, her eyes lighting up with amusement. “I might make you my maid for the rest of the day Poppy. You’d look perfect dusting shelves in this get-up.”

Poppy turned to her, a faint blush on his cheeks and, to Jilly’s surprise, he said softly, “Okay, I would like that, Jilly.”

Jilly’s teasing smile faltered - she had not expected that response. “Okay, let me find some chores for Maid Poppy.” She laughed but inside there was a hint of something that suggested she wasn’t entirely joking.

***

Jilly had a mischievous glint in her eye. "Alright, Poppy, the house isn't going to clean itself, is it? Time to get to work."

“I’m ready Jilly," he replied, voice soft but obedient.

Jilly said. "Good, I want you to start by dusting the shelves. And don't forget to wipe down the kitchen counters when you're done in here. I want everything spotless. You know I can't stand a messy house."

Poppy nodded again and unnecessarily cleaned undusty shelves and undirty countertops. He felt the burn in his thighs as he crouched down, each movement reminding him how strictly the corset controlled its occupant. The feeling of being trapped in the uniform, the metal boning digging into her sides with every breath, was thrilling and suffocating at the same time. But Poppy didn’t dare complain, fearing Jilly would declare the game over.

Jilly watched him work, the faintest hint of a smile on her lips. "That's it," she said, her tone firm. "Now, after you're done with that, make lunch. I’m feeling hungry. Don’t make it too complicated, I just want something simple.”

"Jilly..." he began as they ate lunch, “a part of me feels trapped in this uniform - like an actual maid.”

Jilly raised an eyebrow, clearly amused by Poppy’s admission. "Oh, really?" she said, her tone light but with a bit of a teasing edge. "Isn't that exactly what you crossdressers long for? To be trapped, controlled, under the command of a strict woman? To be forced to rely on someone else for your release?”

Poppy’s cheeks flushed as he looked down, embarrassed but also secretly aroused at the idea. After just a couple of hours there was a part of him, hidden deep down inside, that liked the feeling of being controlled, of not being in charge, of letting someone else decide. He didn’t want to admit it out loud, but the thought made his heart race. He blushed even deeper, glancing up at Jilly. "You might know me a little too well,”