The next morning, a bleary-eyed Tommy descended Maddison's stairs and entered the living room, dressed in the short nighty he'd borrowed from her the night before.
Maddison, lounging on the sofa and watching TV, looked up with a smile. “Good morning, Tammy. How did you sleep?”
Tommy managed a small, embarrassed smile. “Okay, I guess,” he replied, glancing down. “Thanks for letting me stay over last night, and… I’m really sorry for calling you so late.”
“Oh, don’t be silly,” Maddison scoffed. “That’s what friends are for. I was just about to make breakfast. What would you like?”
“Thanks, but I’m not really hungry,” Tommy mumbled, folding his arms and shuffling his feet.
Picking up on his mood, Maddison slid over and patted the cushion beside her. “Hey, come sit with me for a minute.”
Tommy nodded and trotted over, carefully folding the flimsy skirt of the nighty beneath him as he sat down. He tucked his smooth legs under him, feeling the warmth of the sofa.
Maddison gently pulled him towards her, letting his head rest against her shoulder as she ran her fingers through his hair. “What happened last night, Tammy? You were pretty shaken up and hardly said a word after I picked you up. I was really worried.”
Maddison’s fingers combing through his long hair felt surprisingly comforting, easing Tommy’s nerves as he began recounting the events of the previous evening. He explained how he’d gone out with Jill and the women from work, how he ended up alone with Dom, and how exposed and vulnerable he’d felt. At first, Maddison asked gentle probing questions, but as Tommy continued, the story started pouring out, and he found himself relieved to finally get it off his chest.
When he finished, Maddison looked outraged. “What? She just left you there?” she exclaimed.
“Yeah… I didn’t know what to do,” Tommy replied, sniffing slightly.
“That’s awful! She sounds like a horrible person. Why did you go out with her in the first place?”
“I didn’t have a choice,” he said defensively. “She basically threatened to get me fired if I didn’t go.”
“And what? You’re that attached to the job?” Maddison asked, incredulously.
“No, it’s not that,” Tommy stammered. “I just… I really need the money.”
“For what?” Maddison pressed.
Tommy hesitated. He’d tried explaining the truth to Maddison before, but she hadn’t believed him. This time, he chose to simplify things. “I need to get away from my sisters. They’re trying to control me - what I wear, what I do. I just… I can’t take it anymore.”
“Oh, Tam, I had no idea,” Maddison replied, looking shocked. “So, because you’ve been brave enough to show the world who you really are, they’re punishing you?” She was visibly upset on his behalf.
“Kind of… but no. It’s complicated,” Tommy answered, wondering if he should try explaining his situation again.
“Complicated how? Tam,” Maddison followed up, her eyes full of genuine concern.
Tommy glanced down, seeing himself in one of Maddison’s nighties, blonde hair spilling over his shoulders. It wasn't the time for the truth. “I'm being silly,” he said with a forced smile. “It’s not that bad. I think they’re trying to help in their own way, and maybe I’m just overreacting because of last night. They did take me in when Mum abandoned me, so I should be more grateful… It’s just hard sometimes.”
Maddison nodded sympathetically. “I get it. But don’t let them control you, okay? I’ve got an older sister too, and trust me, standing up for yourself is important.”
"Thanks, Maddy," Tommy said, turning to look her in the eye, appreciating how supportive she had been. “And… I’m sorry.”
“Sorry? For what?” she asked, giving him a reassuring squeeze.
“That I never made the effort to get to know you better. You’re a really nice person,” he admitted, feeling a twinge of guilt over the years he’d spent fantasizing about her, objectifying her in his mind in ways that felt shamefully similar to how Dom had treated him the previous night.
“Aww, that’s really sweet, Tam,” Maddison replied, sounding touched. “But don’t worry about that. Better late than never, right? I have a feeling we’re going to be best friends from now on,” she added, pulling him into a warm, tight hug.
Four hours later, after an afternoon spent lounging and watching cheesy movies, Tommy, now showered and refreshed, returned to the living room. Finding it empty, he tottered to the centre of the room and called out Maddison's name.
“Coming!” she called back, her footsteps approaching. “Just cleaning up the kitchen. Nothing worse than…” Maddison stopped mid-sentence as she rounded the corner, her gaze falling on Tommy, a smile spreading across her face as she looked him over with an amused expression.
“What? Is something wrong?” Tommy asked, noticing her reaction and suddenly feeling a bit self-conscious.
“No, nothing at all!” Maddison replied with a giggle. “I just can’t get over how different you look these days. In a good way, though.”
“So, why are you looking at me like that?” he asked, worried he’d made some kind of mistake.
“Sorry, I'm just surprised by your choice. That’s my favourite skirt, and you look better in it than I do,” she giggled.
“Oh, sorry! I didn’t realize,” Tommy stammered, glancing down at the black-and-white pleated mini-skirt that ended halfway down his pantyhosed thigh while smoothing his hands over its sides. “It was on your chair with this sweater. I didn’t want to go through your things, so I just put it on. I can change if you want?”
“No need! It looks great on you,” Maddison replied warmly. “I told you to pick whatever you wanted. You look super cute!”
“Er… okay. Thanks,” Tommy replied, feeling a bit awkward and suddenly regretting not searching for a pair of jeans or perhaps some sweatpants instead.
“Oh, don’t be embarrassed! You look amazing,” Maddison teased, giving him an approving once-over before her gaze settled on his feet. “Really into heels, huh? Funny, I dug those old wedges out of my closet yesterday. I wore them to death back in the day, but I was going to donate them. If you like them, they’re yours.”
“Thanks,” Tommy replied, forcing a smile as he glanced down at his feet. It struck him then why these towering wedges felt so familiar - Maddison had practically lived in these during their final year of school, and he’d often watched her gliding around in them, looking incredible. Now, perched awkwardly atop them, he felt anything but graceful. In reality, he’d have preferred a pair of trainers, but he knew that if his sisters caught him returning home in flats, his next forfeit would mean drawing twice. And that was a risk he wasn’t willing to take.
Maddison smiled. “You know, I was a bit shocked when I first saw you at the shopping centre, but now I can’t believe I didn’t see it sooner - You’re definitely a girl - maybe even girlier than me!”
“What?” Tommy blurted out. “Why would you say that?”
“Oh, I don’t know,” Maddison replied playfully. “Could be the hair, or that adorable outfit you put together. Perhaps it’s the six-inch heels you seem to live in now. Or maybe,” she added with a smirk, “it’s that as tired as you were, you still put on makeup before coming down this morning.”
Tommy was at a loss for words. Here he was, finally in Maddison's panties - just not in the way he’d dreamed. He wanted to explain - tell her he wasn’t wearing a stitch of makeup, that the lash extensions and lip plumping just made him look like this now. But instead, he managed only a nervous grin until Maddison spoke again.
“Right, let me grab us some coats and I’ll drive you home,” Maddison announced cheerfully as she skipped out of the room. "Drop it back next time you're over."
Back home that evening, Tommy tried to steer clear of his sisters, but they had other plans. Around 9 p.m., a knock sounded on his bedroom door before Sarah and Monica let themselves in.
“So, are you going to tell us where you were last night? We were worried,” Sarah said, watching him closely from the doorway.
“Really? I didn’t know you cared,” Tommy shot back, irritation flickering across his face.
“Of course we care! We’re family. Where were you? You didn’t even call to let us know you’d be staying out,” Monica said softly, stepping out from behind Sarah with a look of genuine concern.
“I don’t want to talk about it,” Tommy shot back, his tone sharp. “And if you really care about me, then why are you holding that hat?”
Sarah’s expression hardened. “Fine, be like that,” she said, shaking her head. “You’re old enough to make your own choices, but next time, at least send a text. Got it?” She took a step forward, hand extended. “Do you have the rent money?”
“You know I don’t,” Tommy replied, his tone tinged with frustration. It would be weeks before his next paycheck, and they all knew it.
“Then put that pretty little hand of yours in and pick,” Sarah said, holding the hat out with a challenging smile.
Resigned, Tommy reached forward before pausing, his long pink nails hovering over the hat. “There are only two slips in here,” he noted, a bit thrown.
“Well, since you stayed out last night and worried us sick, we decided to give you two very special options this week. One from each of us,” Sarah explained, a wicked grin spreading across her face. She reached in and unfolded the first slip, reading it aloud. “Maid for the week. That one’s mine,” she announced smugly. “Pick this, and you’ll be at our beck and call all week, doing all the housework for a change.”
The corner of Tommy's plumped lip curled as Sarah reached in for the second slip and read it out. “Princess for a week,” she declared, trying to keep a straight face. “That one’s Monica’s. Not sure what ‘princess duties’ she has in mind for you, but it sounds like fun.” She raised an eyebrow, clearly enjoying his discomfort. “So, Tammy, what’ll it be?”