A Princess's New Kitten

Elizzyviolet here: this story has romantic elements, but might not necessarily count as a proper romance due to the exact nature of the relationship between the rich girl and the crossdressing protagonist. Check the tags before reading, and enjoy!

~~~~~ ~~~~~

Lionel signed the last of the papers, dreading what exactly this role would entail. He was just hired as a butler for one of the richest girls in the country. He was twenty, he knew nothing about this girl or even how she got her money, and the only job he ever had was delivering pizzas. And now he was in the private library of the biggest mansion he'd ever seen with his own eyes. Half of these books were a century old, and he was sitting at a table on the second story of the warmly lit chamber.

"Are you okay?" the older woman sitting in front of him said. She was fairly tall, making her a bit intimidating to the short Lionel. She was the rich girl's lawyer, and even though it made sense to fill out all the paperwork with her... why was this lawyer also the one who interviewed him? There was a head butler coordinating all the various servants, but he had nothing to do with any of the interviews. Maybe he was just busy or something.

"I'm fine. It's just... it's all a bit much.," he said, unconsciously running his fingers through his long brown hair out of stress.

"You're completely done; no need to worry. You have the job, and I assure you, you're perfectly qualified. Everything about you makes you ideal for this role. Now, there is one last paper; I assume you're familiar with NDAs, correct?"

He was googling "common job documents" the day before to try and prepare for today's interview, but got distracted by femboy porn. In retrospect, he probably should have looked up the rich woman he would actually be working for.

"You'll handle some particularly sensitive tasks for Miss Linington, so this document is an agreement to disclose nothing whatsoever about the position to anyone. Your job title is 'Butler,' and that's all you can say about it; even to the other staff here, you should only talk about what you do when it's absolutely necessary. They won't ask unless they absolutely need to know something."

He signed the NDA, then mustered the courage to ask.

"And what sensitive tasks will I be doing?"

"It's entirely up to Miss Linington and what she needs at the time."

He tried getting clarification a few more times, but with no results. Whatever he was going to do, he'd find out later, and not now.

"So," the lawyer said, "You said you could start tomorrow, so be here by one in the afternoon. You'll be taken to Miss Linington's room, and you can finally meet her."

After concluding the process, he was escorted out of the building and back to his car. Although he was excited, he was even more terrified. He thought about refusing all this and just keeping his pizza delivery job. He liked driving and he liked pizza. This job had neither.

Once he got back to his apartment, he plopped onto his pink bedsheets, thought about it for a while and let out a deep sigh. There was no way he could pass this up. The pay was too good. He called his manager to tell him that he probably had a new job and wouldn't be showing up tomorrow, and then he relaxed by finding some good femdom hentai.

~~~~~ ~~~~~

He arrived fifteen minutes early, but it still felt wrong to arrive at work this late in the day. Miss Linington's erratic schedule meant that he'd be working some strange hours from now on.

That lawyer--he was terrible with names, so he already forgot--led him through the mansion's hallways. He had to leave his phone, wallet, and keys near the entrance for "privacy reasons".

"You should get the hang of the layout after your first day," she said. "But if you're lost, just ask someone. Miss Linington just got back from Philadelphia, and she should have just finished a few calls."

The lawyer stopped outside a large mahogany door with an old brass knob.

"And you can go on in; you shouldn't need me, but I'll be here until late tonight. You're all hers until nine; come and see me once you're done."

The lawyer started walking away, and Lionel cautiously turned the brass handle and stepped through.

Miss Linington's bedroom was the size of Lionel's whole apartment, and it had a wonderful pink and red theme. Between the rose-hued canopied bed, the pink beanbag chairs on the beige carpet, the enormous red curtains which must have cost a fortune, and the two rose-gold laptops on the desk in the corner, Lionel felt kind of jealous. He decided that he would style his room like this if he ever had the money for it.

Miss Linington emerged from her closet, wearing a long-sleeved frilly pink dress and a pair of long white socks. She wasn't that tall, but she was still taller than him. He did everything he could not to stare, but she did look good--especially with the pink streaks of dye in her long brown hair. She didn't look like a multi-millionaire; she just looked like a girl who was really into cutesy stuff.

It took all his effort to avoid succumbing to anxiety and to say his prepared line.

"Good evening Miss Linington," Lionel said. "I'm the new butler."

She nodded. "You can just call me Lillian. Have a seat, make yourself cozy, and just relax," she said with a smile as she gestured to one of the beanbag chairs by the TV.

He sat down. This was a good beanbag chair. It had enough bulk to hold him up, but it was soft enough for him to sink into. She sat down on the other chair and pulled her phone out of a hidden pocket in her dress. Maybe this wouldn't be such a stressful job after all.

"So," Lillian said, "I learned a lot about you over the last few days. Yesterday morning, you left a comment saying, and I quote, 'oh god i wish that were me' on a video titled 'Cute femboy gets dominated by tall lady?' And later that evening, you watched two hours of dominatrix femdom videos with both male and female subs? In full?"

Lionel wanted to jump out the window, but instead he sat perfectly still in terror. His heart pounded. His face felt warm. She seemed... intrigued and excited?

He briefly overcame his terror to speak. "How did you know?" he said as he sank into his chair.

"My tech people didn't have anything else to do at the time, so in addition to all the other incredibly invasive spying we did, I had them put spyware in a few of the email attachments my lawyer sent you last week. Honestly Lionel, you have great taste!"

So that was why they kept getting flagged as malware! The lawyer told him to ignore it during their emails.

He wanted to ask why, but he was frozen with terror again. And his stupid humiliation fetish was making him hard. She probably knew about that one too. And the crossdressing. And all of the others on the list.

Lillian giggled. "But yes, I hand-picked you since you were into everything I liked. And you're cute too. I think you ought to get that hair dyed sometime, you'd look great with turquoise in there. I assume my lawyer was vague about what you would actually be doing?"

"She said pretty much nothing," he said.

"As I expected. Anyway, I spend a lot of time on flights, meeting with boards, handling finances, managing companies, arranging deals... and ugh, it's a lot. Those guys in Philadelphia have no idea how to run a business, let alone sell one, and their bullshit isn't the worst I've dealt with. I want a little someone here I can have fun with."

"Um... are you saying..."

"Yes. And once that anxiety goes away, you'll love it. I made sure you would before hiring you."

He did fantasize about all the things he watched, and he wished it would happen to him. But here? Now? It was all too sudden...

"How about we start with you picking out an outfit?" Lillian asked. "Come with me. I have a couple of things in your size."

She got up, put her phone on her nightstand, and started walking to her second closet. Lionel stood up and almost fell over from his wobbly legs and general clumsiness. He slowly and carefully followed her, and she opened the closet door.

What he saw in the brightly lit closet were racks and racks of the prettiest clothing he'd ever seen. There had to be dozens of dresses, blouses, skirts, and shoes, and a gorgeous collection of jewelry was proudly presented in a series of shining display cases. Socks, bras, and underwear were all neatly tucked in glass drawers, and there were even chokers, garter belts, arm warmers, cat ear headbands, and every other kind of accessory he could name.

"I might pick something out for you, but try on whatever you like."

This heavenly trove of clothes was all his to try. So many options...

"It, um, I might take a while..." Lionel stuttered out.

"No worries! Take your time. I don't mind watching you experiment. And when you undress, feel free to put your old clothes in that corner. You won't need them for a while."

His anxiety started transitioning into giddy excitement as he dug through the closet. He picked up an excessively long red skirt before his attention was grabbed by a flower patterned turquoise one. Then he picked up a simple yet soft white skirt before noticing a puffy ball gown...

He eventually picked up a sparkling white dress and held it in front of him. It had short sleeves, a short skirt, tons of lace, and the design prominently showed off the chest. This would fit. And he would feel so cute...

"That one? I know a few things that go with it..."

Nervousness flooded back into him when he remembered that someone else was in the room. Lillian brought him two long white stockings, as well as some lace panties and a heavily padded bra.

"And take all the accessories you like."

He definitely wanted the white leather choker, so he grabbed that. And maybe some jewelry... The silver necklace with a gorgeous ruby drew his gaze, and so did the simple silver ring with a small diamond in it. Then a difficult decision came up. Cat ear headband or no cat ear headband? He decided to ignore the headband this time, and he went with a little white bow he could put into his hair.

"And you can grab shoes if you want. I don't mind you wearing them here."

Then there were shoes... The heels were all fine, but the little white boots with pink stripes looked so cute! He needed them.

The outfit was assembled. All he had to do was undress and put it on. He slipped off his shoes and socks, then unbuckled his belt and took off his suit and undershirt. Now shirtless, he felt vulnerable and naked. The pants weren't even off yet.

He quickly took off his pants and underwear, and then he noticed her looking at his cleanly shaved legs and groin. Wanting to save himself the embarrassment of her looking at his erection for too long, he grabbed the panties and slipped them on as quickly as possible. Comfort and arousal spread through him, but it wasn't enough. Then the bra went on, and it took some time to get the clasp hooked.

When it was tightly on his chest, he looked down at himself. Once the dress was on, it would give him a nice, prominent chest. Next were the socks, and those went all the way to his thighs. The tightness of these slightly transparent socks filled him with a warm and cozy feeling.

Now the dress. It took some time to figure out how to slip it on, but when he finally put his arms through the sleeves and adjusted everything, it felt almost heavenly. He picked up the choker and looked at it.

"How about I put it on for you?" Lillian said, once again reminding him that he wasn't alone. He gave her the choker and turned away, and she reached up to his neck, moved his long brown hair aside, and slipped the choker around him. The snap fasteners clicked shut, and a tingle of arousal went through Lionel.

Next were the ring and necklace. He put the ring on his left hand, and Lillian slid the ruby necklace over his head.

Finally, the short white and pink striped boots. He slipped the left one on, enjoying how it felt, then put the right one on. He took a short walk around in the closet, and Lillian followed him to the mirrors.

Lionel looked at himself in the prism-like matrix of reflections in front of him. He was stunned by how he looked from the front. He didn't actually think he could pull this off; he looked a lot like a bride, but the shoes and jewelry gave him a playful, casual feel too.

He peeked at the side reflection of himself and was surprised by how his chest looked. The transition from a completely flat chest to decent breasts was astounding.

Lillian examined his body. "Ah... now this is how more people should dress these days. Would you like to see the garden with me? I don't think you've visited. And maybe you'd love to take a walk in those clothes."

This mansion had a garden? As long as nobody outside the mansion saw him...

"Um... sure," he said.

"Don't be nervous; the staff won't mind."

He emerged from the closet as an almost completely different person, and followed her out of the room. She grabbed her phone on the way out and texted someone, but Lionel didn't peek to see what she sent.

She led him through a familiar hallway, and then took a turn at a different staircase and went down a floor. A little more walking, and she led him through a pair of glass double doors.

He stepped out into the brilliant sunlight and into a maze of shining greenery. High stone walls surrounded the garden, and the summer sun was almost directly overhead.

She held his hand as they walked through the cobblestone path, passing by a lone gardener who paid them no attention. After passing under a few trees, they came to vibrant beds of tulips that softly bobbed in the calm, warm wind. Bushes of plum-purple and sapphire-blue hydrangeas were nestled in between the beds, and Lionel stopped to examine them.

These puffy clusters of petals looked almost like delicious fruits, and he only just now realized how hungry he was. Every other splotch of color in this garden suddenly looked like a bell pepper or a peach or any of his other favorite tasty treats. He even found himself staring not just at the roses, but at the moist brownie-like mulch underneath the plants.

Lillian enthusiastically told him about some of her recent business dealings; he had less financial knowledge than a cat and understood almost none of it, but he nodded along anyway. Eventually, her hobbies came up.

"So I haven't played any video games in months; again, it was just too much of a time sink. And I tried collecting fine art like my cousins, but I just couldn't get into it. I kept looking at them as investments instead of actual art pieces, and I couldn't even do anything to control their value. Art markets are just fucked. Then I bought some bean bag chairs for a thousandth of the price and my life instantly got better."

"They were nice chairs. I'd rather sit on one of those than the Mona Lisa."

"I doubt it would be very comfortable. And anyway, these beanbag chairs gave me the idea to renovate the bedroom. It's quite the upgrade from its old beige look."

A maid showed up with something on a small platter.

"Ah, finally!" Lillian said. "The sundaes."

There were two strawberry sundaes on the platter, and the hungry Lionel was absolutely enthralled by them. Alternating layers of ice cream and syrupy strawberries were in the parfait glasses, and the sundaes were topped with waffle cone pieces, sprinkles, and whipped cream.

The maid handed them their sundaes, and they kept walking, talking, and admiring their surroundings as they ate. Lionel delighted in every spoonful of sundae, and the crunch of waffle cone made the creamy, fruity dish even better.

"And I assume you love it?" Lillian asked.

"Ymmph!" he said while chewing on a sprinkle-coated strawberry.

By the time they were both finished, they were almost done with their walk. Lillian showed him the last few unique flowers she had, and then they went back inside into the mansion. They set their parfait glasses on a table by the door and walked through the crisp, air-conditioned interior.

When they made it back into Lillian's bedroom, they took off their shoes, and then she sat on her bed and leaned back.

"Ah... you know, I have to be in Philadelphia again by eight tomorrow, and I am sooooo looking forward to being done with this whole deal. I buy the company off these morons. I fix it up so it's not shit anymore. And then it's another good revenue stream that I only have to manage every now and then. But honestly, tomorrow is going to be a headache."

"Anything I can do?" Lionel asked.

"Oh yes!" she said. "An afternoon of rough activities should help me sleep."

His calm contentment was replaced with nervous arousal once more.

"And hmmm, let me think about what I'd like to do with you..."

He had a seat on one of the beanbag chairs while she thought. After a minute, she sat up.

"Oh yes, that'll do nicely. Stay there while I grab a few things from my closet."

She opened her first closet and closed the door behind her. He heard her root around in there for a few minutes, and was both eager and anxious to see what she would walk out with.

She emerged with a leather bag in her arms. It was absolutely stuffed with things, and three pink dildos were sticking out of the top.

"Alright," Lillian said. "I'll need you to take off that choker. I have something better."

She pulled out a pink collar with a stainless steel chain attached to a ring on the front. It was much thicker than the white choker he was wearing, and instead of a clasp, it had an actual lock with a key.

He stood up and took off his choker. The thick, tall collar was placed around his neck, and then with a powerful click, it was snapped in place. Lillian turned a key in the back and locked it shut. This tight, domineering pink collar was out of place compared to the rest of his outfit, which just made it all the more arousing. His chain was hanging loose, but he knew that she would pull on it eventually, and he knew exactly how he would feel.

Next, she took one of the pink strap-on dildos out of her bag, and Lionel's ass clenched in anticipation. She reached under her dress and attached it to the outside of her underwear, and now she had a girthy, pink erection underneath her dress.

She sat down on a beanbag chair.

"I'm not going to put it in you just yet. For now, just have a seat on top of me."

Lionel carefully sat down on top of her. The beanbag chair squished a little further under their combined weight, but it was big and sturdy enough to hold them. He felt her legs through the two layers of dress fabric, and her dildo gently poked the underside of his right thigh.

She reached in front of him and started groping his bra-clad chest. She moved her hips around, sliding her dildo between his thighs. His erection pulsed with excitement.

She whispered into his ear while playing with his chest. "I can't wait to put this in you," she said. "Imagine it inside you. Just buried deep in there. Nothing to worry about. Nothing you need to think about. Just enjoying me going in and out."

"I can't wait either," he whispered back with a little nervousness.

"Is this your first time?"

"Yes."

"With anyone?"

"I hope you don't mind... but yes."

"Ah... you haven't really had a chance to be a slut, have you?"

The word made him shudder.

"You can be as slutty as you want around me," Lillian said. "I'd love it. Just a little playful kitten I can have fun with."

She pulled up both of their skirts, sliding the strapon between his bare thighs and pressing it against the rear of his panties.

"And then you'll go home every night, and then I'll pull on your chain and bring you back, where you can be my playful pet."

She gently tugged the chain on his collar, then she reached down the front of his dress, underneath his bra, and started running her fingers across his sensitive nipples.