Billy's Halloween - pt 2

(Find all parts to date here)

Billy walked very carefully down the stairs of his house, one tentative step at a time.

He’d made this journey many times before, even in heels; but now he was wearing Louboutins on his feet, and was a little scared that with one errant step, he was going to break them, and possibly himself too. Combined with the restrictive dress he had on, it meant he descended quite slowly, hearing the vague sniffling of his mother from the living room.

As Billy reached the bottom of the stairs he heard Linda call out. “Is that you?

“Yes,” Billy called back, still using his own voice for now. “You have some explaining to do, mother,” he added.

Feeling more confident now he was on solid ground, Billy strode through the house and into the living room, making a theatrical entrance as he threw his arms up and posed in the doorway. “Ta-daaaaa!”

Linda blew her nose unceremoniously, barely looking up. “You look great, honey,” she said, tossing another disposable tissue into a nearby wastebasket. “Good job. At least with the ‘getting ready’ part.”

“Thanks!” Billy replied, again using his own voice. “I have to admit, I think the heels definitely help. And that is what I need you to explain, mom.” He pointed down at his hose clad feet, standing gracefully in the ‘So Kate’ heels he’d discovered. “When the hell did you get these?”

Linda looked at him, really for the first time. Her eyes widened. “Oh shit,” she said.

Billy suddenly felt embarrassed, as if his mother didn’t know about him, hadn’t given her express permission for him to impersonate her. “I’m sorry,” he said quickly, “was I not supposed to touch these? I know they’re yours, but I figured you wouldn’t mind, considering–”

Linda interrupted him, sighing. “You weren’t supposed to touch them, but not because they’re mine,” she said. “They were going to be yours, because they were a Christmas gift, nosy!”

Billy felt himself flush beneath his mask. “Oh my God – I am so, so sorry!”

“They weren’t exactly easy to find, were they?“ Linda said, grinning. “I was trying to hide them because I knew it was possible you’d go looking through my closet at some point, for some reason.”

Billy nodded along as she said this, feeling deeply embarrassed that he’d managed to inadvertently discover what was a very generous Christmas present. “Mom, honestly, these are too expensive for me anyway,” he said. “Maybe you can take them back?”

Linda shook her head and blew her nose again. “No, you’ve worn them now. And besides, I’m paying them off in installments. C’mere, let me see you in them.”

Still embarrassed but also excited to show off his new look, Billy stepped into the living room properly, turning in a pirouette, feet as light as a dancer. The dress flared up slightly as he turned, showing off his legs, making him wonder if he’d be on the dance floor later that night. After allowing Linda to observe the Louboutin heels in action, he stood still, placing his hands lightly on his feminized hips. “Well, what do you think?“

“I have to admit,” Linda said, “they do look very good on you.”

“They look good on you too,” Billy said. “I’m pretty sure I’m living proof of that.”

Linda began to laugh, which caused her to break into a coughing fit. “Oh God,” she said, regaining control of her breath, “please don't make me laugh!”

“Sorry,” Billy said, putting an innocent grin on Linda’s face.

“I’m just glad they fit,” Linda continued. “At least we have a good reason for you to wear them before Christmas.”

“Honestly, I don’t think Elvira ever actually wore Louboutins,” Billy said. “Did they even exist back then?”

Linda shrugged. “I have no idea. I didn’t buy them for the Elvira costume, obviously. I just bought them for you because I figured you’d like them. They’re kind of iconic and, I mean – it’s pretty obvious you love heels.”

Billy had to nod. “Well, whether it was for Elvira or just for me, they’re fantastic.” Billy carefully stepped near his mother, leaned down – feeling the weight of his breast forms – and kissed her on the top of the head. “You’re the best, mom.”

“I know,” Linda said with a chuckle and another sneeze.

“I also have to admit,” Billy said as he walked back across the room, his confidence in the new heels increasing with every stride, “they make me feel incredibly sexy.”

He stopped and turned, allowing one dark leg to be exposed by the dress’ high slit, imagining for a split second that Linda was an excited observer of his impersonation.

Instead of applauding or giving a wolf whistle, however, Linda just rolled her eyes. “Okay, thank you… I don’t need to hear all of your thoughts on this.”

Billy chuckled. “You do remember how I tend to be a lot more honest when I’m dressed like this, right? Wasn’t that a sort of benefit to me telling you?”

Linda moaned theatrically. “I guess… god.” She smiled and dabbed at her nose. “You don’t have to tell me everything about everything, though.”

“Fair,” said Billy. He moved to the couch, a respectable distance away from his mother, sat down and crossed his legs. Unsurprisingly, the dress fell open all the way up to his thigh, exposing a generous measure of his dark hose. He looked down at his leg and shrugged. Elvira never seemed to worry about that sort of thing.

“You do look very good,” Linda said with a sniff. “We should talk about the party though.”

“Yes,” Billy said, turning slightly towards her and leaning back into the couch, allowing his very prominent chest to become even more prominent.

Linda noticed. “Hang on,” she said, narrowing her eyes suspiciously. “What did you do?”

Billy smiled. “You noticed? I have to admit, I use one of my own bras. They just needed a little bit of extra oomph. After all, Elvira was pretty well known for, well–”

“I know, I know,” Linda said, cutting him off. “Don’t remind me. I know I told you that–”

“You’re convinced you’d make more in tips, right.” He pulled a quizzical Linda face. “That was ‘tips’, right? I heard that–”

“Stop it now,” Linda said with a laugh. “Anyway. Yeah. You’re gonna get… tips.”

“And that’s why I’m prepared,” Billy said. “Now, tell me all about this thing.”