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A Night to Remember

Summary:

A perfect opportunity arises for the force to get information on a dangerous suspect, and Chief tasks Dog Man with the job. His mission? Go undercover as a patron named Gretchen and get as much information on the suspect as he can. And all is going well! The suspect is taking the bait, and with the information Dog Man has received, this guy will be in jail in no time! But everything shifts when a figure comes to the table. A figure that could ruin all of Dog Man’s hard work and get him caught. A figure who himself should be in jail right now. Petey The Cat. Now, just what does he think he’s doing?

AKA: Dog Man goes undercover in drag, and Petey tries to crash the party. Oh, what chaos is to come?

Notes:

CW for mentions of drug-slinging.

GRETCHEN'S BACK BITCHES! WHOOOO!

So, I began writing this instead of working on my AUs because it was eating away at my brain. I hope y'all ordered more Dog Man in drag, because that's what you're getting! Enjoy, my lovelies!

(See the end of the work for more notes.)

Chapter 1: Completing the Mission

Notes:

EDIT 2/28/2026: Small edits and paragraph spacing changes!

Chapter Text

“Alright, listen up, Dog Man! We're so close to taking down Cyrus. We just need a little more information about his next plan, and then we can finally put him behind bars!” Chief declared, looking at the hybrid who stood in front of his desk. Dog Man nodded, focused and ready for whatever task he was getting.

 

It was past his normal work hours, and normally he would be home with Li’l Petey and 80-HD. Playing games, watching movies, eating dinner, then going to bed to start a brand new day. However, Cyrus, a ginger Ragdoll Maine Coon, has been a thorn in the police force’s side for a good two months now; for Dog Man, one.

 

Cyrus was a drug slinger. It wasn’t Dog Man's jurisdiction, but after a month of failed attempts to stop the feline, he was pulled into the case. And while the hybrid's help had been extremely valuable, it still took another month for them to get to this point. This meant that Dog Man had been working longer hours, sometimes even having to go back to work during the wee hours of the night.

 

Luckily, Sarah was more than happy to look after the little kitten while Dog Man did this.

 

A wave a relief flowed through him at Chief's words. If they could finally take Cyrus down, it meant he could go back to his normal routine and make up for lost time with Li’l Petey and 80-HD! He would do anything for that goal and to not have to do these late nights anymore. He’d rather take a million baths than work like this ever again.

 

So, what are you thinking?” Dog Man signed, eager to hear what Chief had thought up.

 

“Well, earlier today I got a tip that he’ll be at a cabaret bar tomorrow night called the ‘Sweet Cream Café.’ I’m thinking if you go in there undercover, you'll be able to get the information we need. Then, we can make a plan to send this cat to jail where he belongs!” Chief explained profoundly. “And don't worry, we'll make the wiretap minimal; that way if anything goes wrong, you can hide it easily.”

 

Dog Man took a couple of minutes to process this information. He’d heard of the Sweet Cream Café before but never been inside. It seemed like a nice place from the descriptions he’s gotten, and it would be a place where Cyrus would let his guard down. The performances, the atmosphere, the alcohol: the perfect recipe to get the dangerous feline to come clean.

 

Besides, it’s been a while since Dog Man’s gotten an undercover mission. And he loves doing them! So why not just go for it?

 

Okay, I’m in. What's my persona and how will the wiretap work?” Dog Man signed. Chief smiled at the hybrid’s answer.

 

“That's what I like to hear! Now, for your persona, I've decided to bring out your Gretchen profile. I believe she's the best option to get the job done.” Dog Man smiled at this, his phantom tail wagging softly behind him. It’s been a while since he's been Gretchen, and he loved being her.

 

He always felt so much more… confident and sexy when he was her. Like, he was finally seen as a normal, attractive, and capable adult when he became Gretchen, and he loved every second of it.

 

“For the wire, I’m thinking of doing a small, clip-on microphone that wirelessly connects to a discrete recording device. Again, so if something goes awry, it’ll be easier to hide them. I’ll make sure everything is ready to go for tomorrow night. You sure you're down for this?” Chief asked point blank.

 

Yes, I want to do this!

 

“Great! Then go home and get some rest. We’ll finalize everything tomorrow.” Dog Man saluted before making his way out of Chief's office and began the journey home. As he walked, he grabbed his phone out of his pocket and sent a text to Sarah, asking how things were going and explaining that he would need her help again tomorrow night.

 

Almost instantly he got a reply back, saying that all was well and that she could, of course, help again tomorrow night. A grateful smile came to Dog Man’s lips. He really didn't know what he'd do without Sarah's generous help this past month. He made a note to himself to give her something as a thank you for everything when this was over.

 

Dog Man then put his phone away, looking up at the night sky as he continued his journey home. Thank goodness this would all be over soon though. He really was getting tired of all these late nights, especially the ones where he had to come back to work at ungodly hours of the night.

 

All he wanted after a long day of work was to spend time with his family, and Cyrus was messing all of that up! Well, soon that would be over. He would no longer have to worry about the dangerous cat, and he could focus on his other work and his family.

 

Like it should be.


‘Wow. They really went all out this time.’ Dog Man thought to himself as he looked at the large, full-body mirror in front of him. He was getting ready for the mission and had changed into the costume he'd wear to become Gretchen. And they really pulled out all the stops with this one. Whoever picked out this costume didn't skimp on any details.

 

This has to be one of the most lavish costumes he's ever worn.

 

The dress comprised a black velvet bodice and a navy blue sequin mermaid fishtail skirt that touched the floor. Said bodice was fitted, displaying a sweetheart neckline, and attached were a pair of off-the-shoulder sleeves that rested comfortably on his forearms. The skirt snugly hugged his hips, and the bottom portion was slightly ruffled and poofy, but not enough to ruin the look or make walking difficult.

 

Along his neck was a white pearl choker with a sapphire in the middle that covered his stitches. Dog Man assumed the pearls and sapphire were not fake, given how they looked and felt against his neck. Covering his arms were black velvet gloves, which reached the bottom of the sleeves of his dress. On his feet he wore a pair of black one-inch heels that fit him perfectly, especially with the black stockings that adorned his legs.

 

Every part of this costume hugged all the right places and emphasized every feature of Dog Man’s body. In other words, he was irresistible.

 

‘Might have to see if they'll let me keep this one.’ Dog Man thought to himself as he reached for the small makeup kit next to him. He always did his own makeup when playing Gretchen. The first time around… well, let's just say there was a lot of growling and snapping that day.

 

So, it was quicker and easier for him to just do it himself. Besides, he's become quite good at applying makeup! To add a little more color to the outfit, Dog Man decided on a simple shimmery gold eyeshadow with winged eyeliner. Simple but effective!

 

Once he finished his makeup and sprayed his face with a little setting spray, it came time to put the last piece in place: his wig. The wig was a dark brown, so dark it looked black, and reached his shoulder blades. Soft beach waves styled the hair, and the bangs were side-swept to the right, allowing his dark brown eyes to be seen. It just brought the whole look together!

 

Dog Man gently grabbed the wig and placed it onto his head, adjusting it so it fit exactly where it needed to be. When he finished, he took another look at himself in the mirror, soaking in the look in its entirety. His heart swelled with confidence and pride at the sight. It was always a rush when he became Gretchen, and tonight was no different.

 

In fact, these feelings were doubled by the knowledge that he would finally take down the menace known as Cyrus. And he'd be doing it while playing the confident, sexy, and ever so loving Gretchen.

 

He couldn't have asked for a better undercover mission.

 

‘Alright, let's get the wiretap placed and get this show on the road! Better watch your back, Cyrus. I’m coming for you.’


The Sweet Cream Café. A beautiful, newly built cabaret bar on the north side of the city that is constantly packed. Hell, people and anthros from other cities travel just to get a taste of the experience that this bar offers. But tonight Gretchen wasn’t out for fun. No, she's on a mission; a mission to find the dangerous criminal Cyrus and find the way to his downfall.

 

And that's exactly what she's going to do.

 

As she drew closer to her destination, she could see the neon sign that displayed the name of the bar. She could also see a very long line of people waiting to get in. Luckily for her, she had a VIP pass tonight. You see, one of the bouncers is a good friend of Chief's from college and was more than happy to let Gretchen inside as soon as she got there.

 

All was set for this plan to go well. Once she reached the entrance, Gretchen’s eyes immediately locked onto the woman standing guard in front of the left-side door. Bingo! That must be Chief’s friend.

 

Gretchen gracefully walked over to the woman, confidence lining every part of her being.

 

Hello, my name is Gretchen. I’m the one Chief told you about. I was instructed to give you this as my VIP pass.” She signed to the woman before handing her a photo she pulled seemingly out of nowhere. The woman smiled as she read the sign and took the photo, a chuckle escaping her.

 

“Yep, I should’ve expected this picture. Go on in, Gretchen. Welcome to the Sweet Cream Café.” The woman said as she opened the door. Gretchen nodded a thank you before walking into the bar. And, as was to be expected, the bar was packed with people and anthros. However, Gretchen was taken aback by the atmosphere that made up the bar.

 

Lit in a gorgeous red hue, the room was lined with velvet and string lights. All over the floor were tables and chairs, and booths filled the right side of the room. Near the base of the stage were a few half-circle chairs.

 

Speaking of the stage, it was glorious! It was lit up brightly by the stage lights, and a performance of music and dancing played out for the patrons to enjoy. Above and pulled to the sides of the stage was a large, burgundy-red velvet curtain with gold trim. The stage itself was made of brown wood, which was stained and was quite large. It rested on the back wall of the room and took up the entire wall.

 

Finally, on the left side of the room was the actual bar, which displayed a lovely array of alcohol. The bar took up most of the wall, but there were still sections on either side that led to other places in the building. Likely the bathrooms. In front of the bar counter was a line of bar stools, the seats made of cushiony, plush velvet.

 

And of course, the bar was packed with patrons. Two bartenders worked hard, getting everyone their drinks, and every couple of minutes, a new server would come to collect drinks or bring back empty glasses. Overall, it was like walking into a wonderland.

 

A glorious wonderland that promised wonder, indulgence, and excitement.

 

‘Wow. This place really exceeds the praise it’s been given.’ Gretchen thought to herself as she continued to soak everything in. But she couldn’t let herself get too distracted! No, she needed to complete her mission. She’s inside, and now she needs to find Cyrus.

 

So, Gretchen began looking around for the feline, turning some heads as she did. She didn’t pay them any mind, though she would be lying if she said she didn’t appreciate the attention. After a few minutes of looking, she finally spotted Cyrus, sitting at a table close to the bar and near the half-circle seats.

 

Target acquired! Time to capture her prey.

 

Gretchen fixed herself up before walking over to where Cyrus was sitting. When she got there, she barked at the feline gently to get his attention. It worked, and the cat looked up, his sapphire-blue eyes widening at the sight before him. Gretchen gave Cyrus a sweet smile before gracefully signing:

 

Is this seat taken?” She batted her eyes gently after signing. The cat sat there for a few seconds before standing up and pulling the seat across from him out.

 

“It is now.” Cyrus replied, gesturing for Gretchen to sit down. His voice was smooth as silk and soft as rain. He wore a cream button-up shirt, a royal purple suit jacket with matching pants, and a black bow tie. In the lobe of his right ear was a sapphire stud earring.

 

Gretchen let out a huffy giggle and took a seat, allowing Cyrus to help scoot the seat in. She signed him a quick thank you as he sat down in his seat.

 

“Well, this is certainly a welcoming surprise. What’s your name, pretty puppy? I’m Cyrus.”

 

Gretchen. It’s a pleasure to meet you, Cyrus,” Gretchen signed, her sweet smile still plastered on her face.

 

“It’s an honor to meet you as well, Gretchen. I must say, I never expected to be greeted by such a lovely lady. What brought you over to my table?” Cyrus asked, looking into Gretchen’s beautiful eyes.

 

You just… look like the kind of trouble I’d like to get into.” The feline smirked at the canine, showing off his fangs, one of which was gold. But before either of them could get another word in, a waitress walked up to the table.

 

“Good evening and welcome to the Sweet Cream Café! Can I get you two anything to drink?” The server asked, pulling out her notepad. The two turned their attention to the server.

 

“I’ll have a Black Russian. What about you, lovely?” The feline looked at Gretchen.

 

A Manhattan, please and thank you,” Gretchen signed sweetly.

 

“A Manhattan for the lady, please and thank you,” Cyrus said, looking back at the server.

 

“A Black Russian and a Manhattan, delightful! I’ll be back with your drinks soon.” And with that, the server walked away to get them their drinks. A soft, huffy giggle escaped Gretchen’s lips as Cyrus once again turned his attention to her.

 

Such a gentleman. I definitely picked right tonight,” Cyrus chuckled a bit at her words.

 

“What can I say? My mama raised me right. Now, why don’t we get to know each other a bit?” Cyrus suggested, his smirk widening. And so they did. For a good two hours they talked, going over each other’s backgrounds, what they do now, and whatever else came to their minds. Light banter, teasing, and flirting lined their conversation, especially the more Cyrus drank.

 

Gretchen watched herself, sticking to slowly sipping her first drink and very gingerly drinking her second. And everything was going swimmingly! She was getting way more information than she ever expected to get. Information that was certain to aid in the clueless cat’s downfall. Not only was she learning about Cyrus’ latest drug-slinging plan, but she was also learning about the ins and outs of his drug operations as a whole!

 

Hell, she even now knew where his hideout was and all the infrastructure that went into it.

 

Yes, this cat was spelling his own doom so easily. By now, Cyrus was tipsy, though he didn’t seem to care, as earlier he had ordered a glass of water to sip on between his alcoholic drinks. Something the canine was grateful for. She didn’t need the feline getting blackout drunk; that would ruin her plan.

 

Gretchen couldn’t be happier with the outcome of her work and the results she was getting! Sure, she came in knowing her mission, but this… this was more than she ever expected from something like this! Hell, if she left now, the force could take down Cyrus in the next few days. That’s what kind of results she was getting.

 

It was absolutely glorious. Nothing could ruin this moment! Or so she thought.

 

“Well, well, well. What do we have here? A little date?” The persona snapped at the voice that stood before the table. Dog Man’s eyes widened, his body freezing a bit.

 

‘No… no, no, no! It can’t be…’

 

“Petey! What a pleasant surprise.” Cyrus said with a bright smile. Dog Man slowly turned his head to see none other than Petey The Cat. His archrival, father of Li’l Petey, his co-parent. A cat who should be in Cat Jail right now and not standing next to him in a bar all dolled up the way he is currently.

 

He wore a white button-up shirt, a scarlet red suit jacket with matching pants, and a black tie. In his ears were a few gold earrings: a pair of dangle earrings with small emeralds interwoven within the earrings in his lobes and a hoop ring in the helix of his left ear. Dog Man had to admit that he looked stunning.

 

But what the hell is he doing here? And why did he come over to the table? I mean, he wouldn’t come over here and cause trouble, right? He’s not even supposed to be here! And he promised he’d begin reforming for Li’l Petey’s sake. So, there’s no way he’ll do anything heinous, right?

 

Right?