All characters depicted are 18+. This story contains the following themes: feminization, sissification, and spanking.

Victor couldn’t believe it. There was a light ringing in his ear, his vision was blurred, and his heart was racing. He sat like this for almost five minutes straight…the television droning on in the background. Once he came to his senses, he shook his head and looked down. In his hands was a slip of paper, something he bought on a whim.

              Looking up, several flashing numbers were still being displayed while the newscaster discussed a solvent shortage. Looking down, he compared the numbers on his paper against those on the screen again.

              04 20 69 80 08

              All of them matched up, he wasn’t dreaming…he even got the lucky ball which was needed for the biggest jackpot of all time…over two billion dollars…

              “YEAHHHHHHHH!!!!!” Victor ran around his messy apartment screaming in joy, not caring if he got kicked out now. Empty energy drinks rolled everywhere, takeout containers flew, and dirty clothes were thrown around as some form of confetti. He had a blast just thinking about the fact that he wouldn’t need to clean anymore, not that he ever did so in the first place.

              “I can get myself a hot babe to clean up after me now! Hell yeah, some bimbo with a huge ass and hips, massive knockers, big ol’ red lips, and a slutty maid’s uniform. I’ll be able to pay her enough that she won’t care if I grab her ass or grope her tits, not like those waitresses who banned me from…well most places around here. Won’t need to deal with any annoying nag like Emily pestering me about not cleaning anymore either, that’s a girl’s job! She’ll regret dumping me now, if she wanted the place clean, she should’a done it herself.”

Emily was one of Victor’s many exes, of course. Since high school, Victor had a long string of failed relationships which he found odd. As he opened another energy drink and chugged it, he considered the fact that he went to the gym every day, got paid enough to buy as many video games as he wanted, and was even cultured enough to tell women how they should dress for him. Wiping his mouth, he threw the empty can at the trashcan and missed. Thinking about Emily sent him on a quiet barrage of insults directed towards women and people in general.

He would like to see the look on the faces of people like Emily, his family, and other exes…but he also didn’t want to have to share any of his hard-earned wealth with them. Emily might want refunds for the great new game console she got him for his birthday, his family will want to bring him back into the fold to pay off their bills, and…well let’s just say Victor was sure at least a few of the restaurants in the area may try to sue him. Then of course there was money owed to some people…who might be more aggressive in getting what he owed to them.

No, he had to keep this a secret from everybody. He would cash his lottery ticket, close down all his old accounts, buy a massive mansion, hire a gorgeous maid…or maids, and live out his new life on a beachfront property. Hell, he’d throw massive parties for all his newfound friends and share the wealth…maybe.

“We’re getting reports that today’s winning numbers have been matched! One lucky participant has bought a ticket with all matching numbers and can claim the $2,091,465,450 prize. Who is this lucky person? Well, we’ll find out soon, as state laws require all winners to claim their prizes in person. So you can bet we’ll be staking out the place 24/7 to sneak a peek at the lucky new billionaire. Also, important to remember is that taking the cash prize means only getting about ONE billion instead of two-”

Victor changed the channel, annoyed that his plans were already being ruined. You could say it was because he’s an only child but he was just selfish. At least that what some of his exes told him. So he needed to claim the prize in person, which he could understand. At least one worker would need to see the winning ticket, but how to get around anyone else recognizing him on tv…

Flipping through the channels while lost in thought, a flash of bright colors gave him pause. “And welcome back to Kimchi’s Drag Bake-off, featuring special guest judge Madame Kawaii!” A tall queen walked out, wearing what looked like a massive caricature of a little girl’s pink-purple-and-orange dress. Aside from the massive bow atop their head, what stuck out to Victor was the person’s doll-like mask. It made them look like a 3D anime character…and totally hid their actual face. That got Victor thinking…

              Stepping out of the rental car, parked about half a mile from the lottery office, Victor took a minute to get his balance right. He was perched atop a pair of pink stilettos, which extended into pastel green latex thigh-highs ending in pink frills. He was starting to sweat a bit in his frilly pink latex shorts and top, the former puffing out with his silicone hip padding. A bit of his tight tummy poked out below a small bow, which itself was affixed below the well-endowed breastplate he was wearing. Puffy sleeves were tight around his shoulders, making it difficult to raise his arms, forcing him into a sort of sissy prance. He made sure his long, latex gloves were being worn correctly, as it was difficult to hold the girly purse containing his ID, keys, a piece of paper, and winning lottery ticket.

              Checking his reflection in the rental’s mirrors, his wig was a cute black bob which was long enough to cover his sides and neck. Two adorable bows held up equally cute pigtails. He picked this hairstyle because it reminded him of something that he couldn’t put his finger on.

But the piece de resistance was the mask. Taking a cue from Madame Kawaii, who Victor spent a good amount of time studying in the past week, he was wearing a kigurumi mask which completely hid his face. Although his vision was a bit limited, it was clear in the mirror that his disguise was perfect. No one would think that a manly man like him was under this elaborate drag queen, anime-esque costume!

              Empowered, Victor made his way to the office. Sashaying along the sidewalk, he was getting plenty of attention from passing cars who honked at him. Even though these mannerisms completely went against his manly nature, he played everything up for the disguise. His family and exes would never even think it could be him.

              At the office doors, he saw the media ready to go. As soon as they spotted him, cameras and reporters surrounded the tottering latex drag queen. They tried to ask “her” questions, getting “her” to discuss their identity, and attempting to get any picture that could reveal anything about the winner. But Victor gave nothing away, he just waltzed past everyone, being sure to give them a shimmy of the hips.

              Once inside, Victor got some relief. The latex was sweltering in the midday sun but at least there was AC on full blast in here. Reading a map, he found the route to the necessary office and felt excitement build as he was nearing his goal. After this was done, he would drive back to his hotel, get out of this stupid get-up, throw it away, and go back to living the top dog lifestyle he was used to…and more!

              Entering the “Lottery Office” doors, there was a sole worker sitting behind a desk. She was wearing a cloth mask and also had a blue bob with two bowed pigtails framing her face, coincidentally like his own wig! Slightly surprised by this coincidence, he paused before prancing over to her. She looked up right as he was struggling to open his purse with his squeaky, slippery gloves. After a few minutes of her staring at him bemused, he pulled out the ticket and slammed it down in front of her.

              “Two billion dollars, I’ll take the cash option, here is my bank account information, make it snappy!” He stood triumphant in all his anime, drag queen glory before the lowly office worker. She couldn’t see him gloating under the mask but seemed to understand based on “her” body language.

              “Well. Congratulations. But I need your ID,” she held out her hand, Victor feeling a bit deflated over how she wasn’t fawning over his winnings. She examined his ID, an eyebrow raised as she looked back at him. “Mask.”

              Victor began sweating again under his mask. “Uhhh…what?”

              “Mask. I need to verify your ID. You can’t claim a prize for another person and you’re wearing a giant mask obscuring your entire face. Take it off. If you want to claim the winnings that is.” She looked at him sheepishly, moving her hands in a way that he couldn’t follow with his limited vision.

              “Shit…” he thought as he moved his hands to the straps behind his head. “It’s only one person, she won’t matter at all…just wish I had put on makeup now…”

              He pulled the mask off, revealing his very bare face, now framed by his perfectly-styled wig and incredibly feminine outfit. She grinned as she stood up and held his ID high.

              “Alright, look at the card so I can get a good look at you. It’s so hard to match your face with that gorgeous wig…Victor was it? Just keeeeeeep looking anddddd there we go. Perfect match beautiful!” After craning his neck for this dumb ID check, he looked down to see her hand moving under her desk and the other handing him his ID.

              “Th-thanks…” he responded sheepishly as he placed everything back in his purse and she noted all his information and tapped away at her computer.

              “Alrighty sweetheart, feel free to put your mask back on and expect your winnings in 4-6 weeks as we verify everything on our end. Congratulations.” She gave him a wide smile as he donned his mask again and walked out of the office. He felt so odd about that encounter…there was something off about the woman.

              But he didn’t care! As he tottered outside again, past the mob of cameras again, he yelled in his car. He was a billionaire! Well, soon enough he would be. For now, he had decided to sell off everything he could and cut short his lease agreement so he could live a while in the luxury of a nice hotel.

              Thinking about what he could spend his money on first, he made it all the way back to his hotel room and started to disrobe. He’d taken off his mask and wig when he heard a text message come in. Looking down to see he who needed to block first, he was met with a picture.

              It was a picture of himself wearing his latex drag outfit…without his mask on. Mouth agape, he looked at the number it was sent from. Jane. “Who was Jane?!?” he wondered as another text came in.

              “Wowwwwww. You look amazing Victor! Or should I say Vicky?”

              “Wtf is this?!?”

“Omg. You really were and still are the worst person I ever dated. You seriously didn’t recognize me? You even wore my hairstyle today.”

              It was then that Victor remembered who Jane was. She was one of his first girlfriends, someone who constantly nagged him for not dressing well for meeting her parents, not paying her back, and worst of all…for never cleaning up after himself. He also dumped her and left town after borrowing money from her cousins…who happened to be in a gang. Great times. She must have gotten this picture while she made him focus on the ID.

              “Oh yeah. Jane. How’s it going?”

              “HA! How’s it going? I lost my chance at going to college because of your dumbass. I’m still working off that debt to my cousins you left me with. But let’s get to the point. You owe me. I know you also owe ALOT of people money. I bet you thought that disguise would keep everyone from knowing you hit the jackpot. Well guess what honey, it looks like I hit the jackpot too. If you don’t do exactly what I say from now on, I’m leaking this picture everywhere. ESPECIALLY to your exes and my cousins. You don’t think I know you were cheating on me back then? Me and Emily are still in touch, I’m sure she’d LOVE to get back at you. And you owe interest. So if you want to keep that money a secret, text me where you’re staying. And keep the outfit on, Vicky. <3”

              Victor stared down at his phone. He mind was blank as he thought about what to do. Could he just hire a lawyer to deal with this? He couldn’t afford one until the money cleared…and Jane’s cousins were scary dudes. All he could think to do was send a short reply and put his mask and wig back on, sitting on the bed until he heard a knock at the door…

Victor looked up after having been on all fours for what seemed like hours. Catching a glimpse outside, he was in awe of the beachfront property. Tucked away on a private beach, the mansion had sole access to the perfectly soft, sandy beach and clear water. He admired the floor-to-ceiling windows in this massive living room for a second before his depth perception shifted to the reflection in front of him.

              The buxom woman wearing a black latex maid’s outfit before him was surely his ideal eyecandy. Hips filled out her dress before it ballooned into a frilly show and apron. Large breasts swayed as she re-positioned herself to better clean the baseboards. She pushed her hair back with her gloved hands, making sure the black bob stayed immaculate. Her frilled white collar kept her neck dry and behind her, a pair of shiny black thigh-high boots made sure she was heard throughout the luxurious household.

              She checked that her crimson lipstick was in place, not wanting to anger her mistress. In all ways, the maid was exactly who Victor would’ve wanted to clean his new home. *SMACK* He was brought back to the present as he felt a sharp wallop to his exposed ass. Turning around, he looked up and saw Jane looking down at him. Mistress Jane that is, if he was addressing her.

              “Well, well, well. Looks like Maid Vicky was caught up in her own reflection. Enjoying yourself a bit too much? I know you look exactly like the bimbo you wanted me to be, how was it you always described your dream girl? Some bimbo with a huge ass and hips, massive knockers, big ol’ red lips, and a slutty maid’s uniform? Well, don’t get too entranced by those lovely lips, you’ve still got work to do before tonight’s party.”

              Victor nodded and got back to scrubbing the floor. He didn’t want to anger Jane as she had what amounted to mountains of blackmail on him. After the initial picture, she forced him into photoshoots, with and without his mask, with the threat of releasing said photo. That turned into more embarrassing photos and videos, with him in various outfits clearly showing a painted face or the mask. That turned into signing over control of his new income and new accounts to her, with the promise that after she got her fair share, it would all be turned over back to him. Plus, nothing would get out regarding that first photo. So, as he moved and jiggled on all fours, getting slapped on his ass again, he focused on how soon enough this mansion would all be his.

The wine cellar where he was sent to retrieve expensive bottles for Mistress’ guests. The bedroom where he made up her enormous, soft bed every morning. The sports cars he was made to wax and shine once a week. The closet that held all the fashionable clothes that Jane wore. It would all be his! …Soon. He could always sell the clothes…at least after he secured his own wardrobe. For now, he would endure the groping and spanking from both her and the guests she kept inviting. She would never turn back on her word…right?

He heard the front door ring as Mistress Jane called out, “Oh! Looks like the first guests are arriving Vicky. Finish up and go clean yourself up, remember no speaking unless you’re spoken to my maid. Oh my gosh, Emily! It’s so good to see you, how have you been?”

Victor gulped as he heard the chattering at the front door, wondering if this was that Emily. Maybe Mistress Jane would allow him to don his mask tonight…if he promised her a larger share of his winnings? He clattered to his feet, grabbing his cleaning supplies. Making his way to his chambers, he realized that Mistress would also be more amenable to a deal if he extended his time as her maid. Maybe she'd even let him wear a longer skirt that didn't showcase his padded ass. He sighed, catching another glimpse of himself in the mirror. At least he did get his dream bimbo…even if she had a bulge on full display.