Billy's Halloween (pt 9)

Billy entered the house but didn’t yell out his usual greeting—not least because his usual greeting was in his own voice. Linda would potentially be asleep, and he didn’t want to wake her up.

Closing the front door softly behind him, he gratefully removed his heels, then padded softly through the house. He found Linda, still on the couch, bundled up under blankets with several discarded tissues around her. Billy was about to turn around and leave when Linda’s eyes opened.

“Oh good,” she said, “you’re back. What time is it? I was out like a light.”

“Before midnight, but not by much,” Billy said. “The party was in full swing, but I’d done my time, so figured I’d get out of there. Or rather, I did your time.”

“Congratulations,” Linda said, reaching for a tissue automatically. “So how was it? How were you, I guess?”

“Well, I think it was fine,” Billy said. “I didn’t hear any complaints. Julie, that contact you gave me, was quite nice. Little intense.”

Billy wasn’t sure he wanted to tell Linda about the conversation with Martin. At least, not the specific details. He felt like he had to say something though, given what had happened.

“I spent some time talking with the CEO.”

“Oh, really? He was there?”

“Yep. Interesting guy. About your age, actually.”

“Makes sense,” Linda said. “What did you two talk about? I can’t imagine I’d have a lot in common with a software CEO, but maybe you did.”

“He mostly wanted to talk about Guardian Girls,” Billy said, which was a white lie at worst. “As you might have guessed, he was the one who asked for you specifically. And also specifically, he asked for the Elvira outfit. He’s a fan of you and a fan of hers, so I guess he wanted to combine the two into one.” He shrugged. “See what would come out the other side.”

“I bet he never expected to get a secret ingredient like you,” Linda said, her chuckle enough to trigger a small cough.

“No, I don’t think he did,” Billy said, wondering if that was exactly what Martin (Jonathan?) had expected. “He didn’t suspect anything, though.” He hoped.

Linda nodded, blew her nose again and said, “Great… and again, thank you. You saved my ass. Speaking of my ass… how was the tip?”

Billy laughed. “Good – great, I think, I haven’t counted it. I probably would have gotten more if I had my Venmo written across my butt, but I still got a lot of cash.”

Dipping into ‘his’ purse, he produced the cash-stuffed envelope. “Plus Julie gave me this,” he said as he handed it over.

Linda took a quick look inside and whistled softly. “That looks big,” she said. “Probably isn’t as much as they paid me, but might be close. Still, it’s a heck of a nice bonus.”

She handed the envelope to Billy – but kept her hand on it.

“Come to think of it,” she said, “I should probably put some of this towards your early Christmas presents. You know, the ones you wore out the door?”

“Uh, sure, if you want to,” Billy said, realizing he’d lose hundreds of dollars in tip money if it went towards the shoes. “Seems fair.”

“I mean,” Linda said, “You won’t have many opportunities to wear them between now and Christmas, right? So maybe we should just let them sit in the box for a couple of months. And we can put the rest of this towards your college fund!”

“Yeah, uh, sounds good,” Billy mumbled.

Linda made him suffer for a second, then broke into a smile. “God, are you going to roll over that easy?” she laughed. “Fight for your tip! What am I, your pimp? Oh, wait, don’t answer that. Yes we should put some money aside but c’mon, you worked tonight, you deserve to get paid.”

Billy grinned. He would have happily pretended to be Linda for a lot longer than a night for free, so any money he might earn was a cherry on top.

“Okay, now go get me off,” Linda said, then groaned. “That sounded terrible. You know what I mean. Just take that thing off. I want to see my son again.”

Billy nodded. “No problem. Can I get you anything?”

“More hot tea would be lovely, but change first. And hurry up! Get your butt back down here so we can watch TV.”

“Be right back,” Billy said with her smile.

///

Walking with confidence, Billy returned to his bedroom, Louboutin heels in hand.

He padded across his floor and sat back down at his dressing table, looking, as he had so many times before, into the face of his mother – although this time, she was made up to look a little different than normal.

Carefully, he reached up and removed the Elvira wig, which was sitting on top of his existing Linda wig, attached to the mask. It felt odd to be removing, effectively, a disguise layered over another disguise.

“Well, it’s been fun,” he said in his own voice, “but it’s time to put you away for now. Hopefully you’ll get to come out and play soon.”

Linda gave him a sideways glance and said, “Oh, I expect you’ll find a reason to have me come out to play, especially considering those heels. I bet Kate would love them.”

“She can’t have them,” Billy replied with a grin. “They’re all mine.”

The removal of his Linda disguise was fairly routine by this point. He would get rid of excess makeup, remove the dentures and the contact lenses, and then finally, at least with the first version of the mask, use solvent to loosen the latex. Now, with his incredible Secondskin mask, all he had to do was apply one line of solvent near his throat and then take the mask off, free and clear.

While the process of removing the disguise was routine, the moment of actual unmasking never was. He never tired of watching Linda’s face slowly being removed, the illusion being dispelled.

So after he had removed his makeup, the dentures, and the contact lenses, Billy took a moment to watch as Linda reached up, plucked the wig cap from her head to free her hair, then dug her nails in at a nearly hidden seam along her collarbone.

“You did great tonight,” she said. “I think a lot of those guys will remember meeting ‘Elvira’ for the rest of their lives.”

Billy chuckled. “Yep. I know some of them definitely enjoyed themselves.”

His fingers relaxed at his collarbone as Linda spoke again. “How many guys do you think are going to go home and jerk off because of you?” Billy could imagine Linda actually asking that question, which made it all the more exciting.

“Probably a decent number,” he said. “This outfit? These tits? My legs in these heels? It leaves quite an impression.”

“I don’t blame them,” he replied to himself as Linda. “Back in the day Elvira made me kind of horny too.”

“Really,” Billy said, wondering if this was something Linda had mentioned in passing, or whether it was just his own imagination.

“She’s sexy, powerful, take charge,” Linda said. “She doesn’t take any shit from men. Of course I had a crush on her.”

“Are you saying being Elvira turns you on?”

“Well,” Linda said with a smile, “I guess that’s up to you.”

Realizing that the real Linda expected him back soon – and with tea – Billy moved quickly. Reaching under his bed, he pulled out a shoebox, popped the top and pulled out his very own Hitachi Magic Wand, cordless and fully charged as usual. This ‘massager’ had brought Billy, Kate and “Linda” a lot of pleasure since Billy had acquired it. He’d been told it was the best, and it turned out it absolutely was.

Before climbing onto the bed he looked down at the dress he still wore, at the dark, hose-clad legs of Elvira. “Uh-oh. Looks like a few things are missing,” he said in Linda’s voice.

After slipping on the Louboutin heels once more, he picked up the Elvira wig and let it settle back on Linda’s head. He hadn’t even bothered with the wig cap, but that was okay. A glance in the mirror told him Linda still looked good. It wasn’t perfect, but was more than enough for his imagination to run riot.

Grabbing his phone with one hand and the Magic Wand with the other, he lay down on his bed, slightly propped up by some pillows.

Slowly he drew one leg up until the heel was digging down into the bed spread. The dress had fallen around his legs, leaving them fully exposed, just as Elvira’s might have been in some old photo shoot. His fingers slid up and down his hose covered thighs for a moment, their slight touch feeling incredible, an electric sensation as he thought back to earlier in the night. Entering the company’s building for the first time. Being seen by the crowd. So, so many selfies… hands touching him, eyes staring at him. None of them aware. None of them knowing.

His cock was beginning to throb, harder and harder, deep within his disguise.

Opening his phone, he looked up ‘Elvira’ on Instagram, hoping to find some cosplay or pictures of Elvira, wanting to imagine himself actually being in those pictures.

To his surprise, he actually was in some of the more recent images.

It looked like some of the partygoers had been pretty quick to upload their photos from the night. One of them had uploaded their selfie with ‘Elvira’ and also some other snaps of Billy as he circulated, plus a couple from when he’d been dancing with the CEO. They’d used a hashtag related to the company but also #Elvira and #ElviraImpersonator, so he knew they’d get some traffic. He realized that while some had credited Linda in their captions, most just called their subject ‘Elvira’.

It irritated him somewhat that Linda wasn’t getting credit for the images, even though he was actually pictured in them. If Linda was going to get more appearance work she needed to be seen. Unfortunately Linda didn’t even have an Instagram account – at least, not one that was publicly known. She did maintain an account but it was strictly to look at other posts, including Billy’s own, innocuous fare.

Billy of course had multiple accounts, including one that he used to just look up mask and disguise related content and another which he sometimes used to post pictures of himself ‘dressed up’. He’d never shown Linda’s face on that account though; that, he felt, would be a step too far.

Part of him really did want to leave a comment on these photos with an account name, suggesting Linda get tagged… but he didn’t think that was too smart.

Instead he went down a brief hashtag hole, finding as many pictures of the party as he could. Between drunken selfies and group shots, he saw more and more pictures of himself-as-Linda-as-Elvira. A suitable hashtag wasn’t always used, with some captions even confused about who was in the picture (the Uber driver’s “sexy witch” comment came back to haunt him). It didn’t matter though. He actually found himself completely distracted by the images, feeling happy he’d been able to bring a little bit of enjoyment to their evening.

Gradually though, his mind kept returning to Martin. To how confident and mature he seemed. How interested he was in Linda, which of course felt like an interest in Billy.

Now his mind filled with the moment he had practically pounced on Billy in the back of the limo, mouth biting down on Elvira’s neck, weight pressing on him, hands on Billy’s legs, talking about how turned on he was. The memory sent a shiver through him.

He pressed a button and the wand buzzed to life.

There was something about Martin, he had to admit. A presence. Almost commanding. Not unlike a vampire, he thought with a sly smile.

As he continued to scroll, continued to look for more images of himself-as-Elvira, his mind kept wandering back to Martin, his strong hands, his rugged features, his winning smile. Billy didn’t meet many men like him on a day-to-day basis. Nor did Linda, he thought. Perhaps she could meet him again.

In fact, he guessed that many people didn’t get a one-to-one audience with someone like him. And here was Billy, having shared a limo with him, and more. He was special. No; his impersonation was special. His version of Linda. His delicious deception….

His heel slid back down the bed, legs spreading apart as he moved the wand into position, pressing down between his legs. There, beneath the panties he’d picked out, the hose he wore and his favorite girl shorts, his hidden cock was able to feel the vibrations of the wand, a subtle sensation but one that had brought him to climax before. He was sure it would tonight.

The bulbous head of the wand was pressed gently but firmly against his feminine mound, the buzz sending waves of pleasure through the latex-silicone vagina and right to his dick. He stifled a groan as his legs closed on the wand for a moment, the vibes transferring to his legs.

Slowly his mind slipped into a fantasy.

He was in what he imagined as the CEO’s office, looking at the man as he unbuttoned his immaculate white tailored shirt, then pulled it apart, exposing a body even Billy was envious of. Even from where Billy was, he could see the man’s erection, pressing hard against his pants, desperate to be free. His hand raised, beckoning Billy to come towards him.

Billy moaned as he imagined the scenario, thinking about being commanded by this man, this man who certainly seemed to like the idea of Linda being imitated – not just by anyone, but by a man, perhaps Billy specifically. Something about Martin’s presence made him feel submissive, almost servant-like; he imagined walking behind the desk and being swept into Martin’s arms, his kiss ferocious, his touch all-encompassing. He’d be pushed back against the desk, Martin insistently kissing him, hands all over his outfit, whatever it might be.

The wand moved up and down now, stroking and teasing him, the vibrations penetrating down to his cock as he felt it grow, pushing back against his disguise.

As he imagined Martin leaning over him, he remembered his touch in the limo, his hand sliding over Billy’s leg. Now he imagined the same hand moving between his thighs, touching his wet pussy like the vibrator was touching it now. He couldn’t help but bite his lip in anticipation, and in his mind’s eye saw Linda doing the same.

She was moaning too, her arousal starting to overwhelm her, because Billy was moaning as her, his instincts kicking in. Somehow he was a surrogate for her, as if it was his job to be seduced by handsome men while the real Linda stayed in the background, aloof and professional.

In his fantasy however, Martin knew exactly what was happening, knew who was behind the mask of Linda’s face – and he loved it, loved the idea of being with a woman who was simultaneously a man. It made him want ‘Linda’ even more, made him want to command her, to order her to do his bidding. Billy imagined walking around Martin’s office in some sort of maid outfit, cleaning and dusting, allowing him to watch as Billy would bend over in just the right spots to give the CEO a clear view of his ass.

The wand pressed down harder, Billy groaning even louder in Linda’s voice.

Suddenly he was imagining the scenario he’d concocted in the limo – that Martin was actually Jonathan in disguise, a possibility that turned him on even more. Given that Jonathan had already managed to seduce Billy by fooling him into thinking he was Linda, anything was possible.

In the end it didn’t matter. Whether Martin really was interested in Billy being Linda, or if Jonathan was somehow the CEO, either of those fantasies were unbearably erotic. His wand was pushed down harder, the fake feminine anatomy reacting to the pressure, his dick pushing back beneath it.

“Oh, fuck that feels good,” he said, losing control for a moment, his own voice coming from Linda’s lips.

While he felt sure he’d eventually climax this way, he was on a clock here. One hand slipped inside his hose and panties, fingers sliding into the fake vagina, as if he could stimulate a fake clitoris. While it could never work the performance was still erotic to him, as if he was maintaining his impersonation in the most intimate of scenarios. As he drew his fingers out, he replaced them with the vibrating head of the wand, the broad round surface parting the fake folds of Linda’s pussy.

Calling out Martin’s name softly, he began to imagine the man kneeling down in the back of the limousine, putting his head between Linda’s legs. Instead of lapping at her pussy though, he would pull her panties to one side to gain access not to Linda’s pussy, but instead to Billy’s rock hard cock.

The image of Martin taking Billy into his mouth without any concerns was almost enough to push Billy to climax, but then he added one more twist.

Somewhere in the middle of his expert blowjob, the CEO would reach up to the back of his head, never releasing Billy’s cock from his mouth. His fingers would dig into the back of his head, burrowing into his hair, and then to Billy’s surprise those fingers would find seams – seams that would be ripped apart, his mouth increasing its suction as the mask would be separated at the back, rippling down and over his head as Martin’s face was removed, and Jonathan would be revealed to have been masquerading as the CEO all along. Jonathan would release Billy’s cock only long enough to peel off the remainder of Martin’s face, leaving the flattened rubbery face of the CEO draped across Billy’s cock. Then Jonathan would grip him forcefully and slowly stroke Billy to an enormous climax, Linda bucking and groaning in the back of the limousine.

That fantasy, that image of Jonathan’s unmasked face smiling as he jerked ‘Linda’ off was what finally drove Billy over the edge, gasping and moaning aloud in his own voice. His hips bucked upwards, pushing against the vibrator, feeling the pressure on his cock which built and built, until hours of pent-up sexual tension finally released into the interior of his rubber pussy as he came again and again.

///

A little more than ten minutes later, Billy arrived back downstairs, feeling a pleasant afterglow from his much anticipated orgasm. He had transformed back to his real self, the Linda mask, Elvira outfit and other clothing left behind in his room.

Now in sweat pants and a t-shirt, he made up some hot tea in the kitchen and then brought it to Linda, who was still sniffling on the couch, but had her phone in hand.

“Thank you,” she said, taking the tea gratefully. “Took your time.”

Billy said nothing. Linda could probably guess what he’d been doing.

“I was bored,” Linda continued, “so I looked up the company? I know you don’t know anything about them, and frankly I didn’t pay much attention either.”

“Funny you should say that,” Billy replied. “The CEO thought I might use one of their products. Who knows.”

“Apparently most of what they do is some sort of ‘cyber security’. Corporate stuff. Very dull. There’s some sort of consumer product too… maybe you use that.” Linda scrolled her phone a bit more as she sipped tea. Billy began to exit, thinking about a snack, when Linda said “Oh” in a way that made him pause.

“What?”

“Nothing, really. Just typical corporate stuff. Basically they got caught with their hand in the cookie jar. Got fined for some sort of privacy thing. Sounds like there was a lawsuit. Maybe you should look into that, perhaps we can get some money!”

Billy chuckled. “I think we got enough of their money tonight, don’t you?” He turned to head to the kitchen.

Linda called after him. “Apparently their software was snooping a bit,” she called out. “Nothing too sensitive, but in theory it could get access to your webcam, it says here.”

Billy paused. “What’s the name of the software? It’s like, an app, right?”

“Says it’s an app and a program? Like on phone, PC, that sort of thing. Uh, it’s called ‘Protego’.”

Free with your purchase. That’s what Billy remembered; when he’d bought a new laptop earlier that year, there had been some offer on, where you got a copy of Protego and a one-year subscription to it for free. Free was a good price. He said yes.

Forgetting about his snack for a moment he ran back upstairs, finding his phone, searching for Protego and the word “lawsuit”.

And there it was. A series of news stories talking about how Protego users had been filmed without their knowledge. Their internet history monitored. Even access to files, if users gave it permission. According to the story a very small number of people had been affected – less than a hundred – but apparently enough for a lawyer to take their case.

That app was on his laptop. He was sure of it. He looked through the apps on his phone, too. There it was. Protego.

An app that could, potentially, access your webcam and search history.

Suddenly his conversation with Martin in the limo took on a much more sinister undertone. He wasn’t Jonathan. He didn’t need to be. If his company’s software was on Billy’s devices… perhaps he knew Billy was Linda, because he already had the evidence to prove it.

The card with Martin’s number on it was on his nightstand. He picked up his phone, and dialed.