Cheesecake Boys

Welcome to the colorful world of the Cheesecake Boys!

I started this series because I was always fascinated with pinup art from the 40’s and 50’s. It was a more innocent time (at least on the surface), and I love the elaborate scenarios that artists like Gil Elvgren and Art Frahm concocted in order to justify disrobing their subjects. It struck me that male models were never portrayed in the same way. While it was considered sexy for a woman’s skirt to be ripped off before a crowd of oglers, male pinups of that era (beefcakes) were generally only exposed by choice. Times certainly have changed! Guys may have had a free pass on wardrobe malfunctions in the good old days, but now the Cheesecake Boys are here to even the score!



This week's free coloring page is based on a wonderful Cheesecake Boy short story by Suited Westend. Give him a follow on Patreon, Twitter, and Instagram for more pants-dropping fun!

  • Download the coloring page by clicking the image below.
  • Color your pants off! You can print it and bust out the crayons or color digitally using your favorite app (Recolor is one that works well).
  • Join the Cheesecake Boys Discord server and share your work with our community on the Show and Tell channel! Also post it on Instagram and tag @cheesecake.boys or email it to me at so I can share!

Happy coloring!



The Richmond School of Art was just a few weeks from its grand opening and the list of tasks to get done before then seemed to grow by the day. 

The Faculty Director, Stephan Morris, was on his way to a meeting with the rest of the leadership team when he came to a dead stop at the commotion happening in the bright, new atrium. 

Surrounded by a small group that included the Dean and his two assistants, a muscular, young man was bent over in the most brightly coloured briefs he’d ever seen. 

“What on earth is going on?” Stephan asked as he rushed over, unable to resist getting a closer look. 

“Nothing to worry about, Stephan,’ the Dean said with a grin. “This is our new Facilities Manager. He’s just having a little difficulty with moving some boxes.”


Earlier that day . . . 


Sam Whitman desperately needed a job! Since he’d finished his football scholarship at college, he’d spent the following three years working out at the gym and hanging out with his buddies, which he’d loved, but his father was less than keen on his lazy lifestyle. 

“You need to get a job, Sam,” he’d said. “You’re 24 years old and you can’t spend the rest of your life living at home with your ma and me.” 

Sam guessed he was right. 

Other people were usually right when it came to . . . well, anything at all. 

Sam had always been a little slower than everyone else. He got there in the end, but he was very conscious that he didn’t learn as fast as other people. 

“What time is your interview, honey?” 

Sam looked up at his mum and did his standard puppy dog head tilt when asked a question. “It’s at two, I think. I need to check the email.” 

“Okay, well don’t be late and remember to wear the new shirt and slacks I left out for you. Good luck!” 

She ruffled his blonde hair as she left the kitchen and went to work. 

Sam bounded up the stairs and decided that he’d shower and change now so that he was ready. He had a bad habit of getting easily distracted and he definitely didn’t want to upset his parents by missing his interview. 

Sam grabbed his phone off of his dresser and decided to set an alarm for 1pm so that he’d have a reminder to leave the house in plenty of time. But when he opened the clock app, there were already four alarms set . . . 

“Check me out being organised,’ he chuckled to himself, before tossing his phone on the bed and switching on his PlayStation.

It was at 12:45 when Sam’s first alarm went off and he stared blankly at his phone wondering what it was for. 

It was only when the second one went off at 12:50 that he remembered the interview and after turning off his console, he dived into the shower. 

After soaping his muscular frame, Sam repeatedly said the word “interview” over and over to stop himself getting distracted. 

In a matter of minutes, he was out of the shower towelling off, before he opened his underwear drawer and frowned at the small selection that was available to him. 

He guessed he hadn’t done laundry for a while. 

The choices weren’t overwhelming as he rifled through a couple of old jockstraps, some boxer shorts with a huge rip in the back and a pair of briefs that were lime green in colour with blue and pink flowers loudly plastered over the material.

“Hmmm, I guess these would work,” he said with a shrug before dropping his towel and pulling them on. 

Sam was about to yank on his favourite pair of jeans when he saw the navy slacks and white shirt that his mom had laid out for him on the back of his desk chair. 

“Oh yeah! I better not forget to wear those.” 

After dressing himself in his new outfit, Sam checked his appearance in the mirror. He was happy to see the same dopey grin he always had, the same messy blonde hair and the same broad shoulders and thick build. 

“I think I should lay off leg day for a bit,” Sam said with a chuckle as he turned to the side and saw how much his bubble butt was straining against the tight material of his slacks. 

With a happy shrug, Sam grabbed his phone and bounced down the stairs.  

Traffic was mercifully light, and Sam pulled into the parking lot just before 2. He was in awe of the beautiful, historic building as he stepped out of the car and walked up the steps to the impressive double doors. 

“This place sure is pretty,’ Sam said aloud to himself as he stepped through the doors. 

The atrium gleamed. It was all polished marble and shiny wood. 

“Can I help you?” a guy a little older than Sam with big glasses and a stack of books in his arms asked as he dashed over. 

Sam frowned. ‘Ummm . . . I’m here for an interview.” 

“Oh, you must be Sam, right?” 

Sam nodded. ‘Yeah, I’m Sam. Do you need some help?” 

Before the guy could answer, Sam easily took the stack of books from him, his biceps bulging in his white shirt. 

“Wow. Thanks for the help. Follow me and I’ll take you to where you need to be.” 

“Okay,’ Sam said with a grin. 

“I’m Tate by the way, I’m one of the Dean’s assistants.”

“Cool. Who’s Dean?” 

Tate chuckled. “Not Dean. The Dean . . . of the school.”

Sam was confused, but he knew he needed to make a good impression, so he just smiled again and followed Tate up a flight of stairs to a wide corridor where the walls were covered in paintings. 

Tate talked away about how excited they were for the school to open, and Sam nodded along, trying to make sure that he didn’t drop any of the heavy books. 

By the time, Tate led him into a huge room filled with easels, Sam was starting to sweat from carrying the heavy load. He dropped the books down on to a desk and was relieved to stretch out his arms when he was done.

Tate was doing his utmost not to stare, but he was still somewhat stunned by this Adonis that appeared at school, and he couldn’t resist looking at the muscular guy in his tight white shirt that was starting to go a little see-through. 

“Thanks for carrying those for me. The Dean is just down here.”

“I like to help and I’m strong so I’m good at carrying stuff.” 

Tate chuckled as Sam beamed at him. “You sure are.” 

Sam was happy that Tate had agreed with him, and he followed him down another corridor to a big office that was filled with books and mismatched furniture. 

“Well, hello to you.” 

A handsome man in his early forties with a chin dimple and a massive smile walked over to Sam and shook his hand. 

“You must be Sam. I’m Dean Robertson, but you can call me Lyle.”

‘Nice to meet you, sir,’ Sam said with another dopey grin. 

“This will be quite an informal interview, I’m afraid as we’re just weeks away from opening our doors and there’s so much still to do. Have you worked at a school before?” 

Sam shook his head. “No, sir.” 

Lyle slapped him on the shoulder. “Don’t worry, it’s not essential. What skills have you got?” 

Sam tried to focus his brain on the question, but he was distracted by a huge truck that was pulling up outside. 

“I . . . I’m good at lifting stuff, right?” Sam said as he turned to Tate. 

Tate nodded. “That’s true. He is good at . . .” 

Tate was cut off when a young, black guy in a fuchsia pink romper ran into the room. “Not to worry anyone, but we’ve just had a huge delivery and some of those boxes are bigger than me.” 

Lyle laughed. “Don’t worry, we’ll all go down. Sam, this is my other assistant, Maxwell.” 

“Call me, Maxy,’ he said with a friendly smile. 

Sam followed them back down to the atrium where a stack of boxes had appeared near the doors. 

“Well, that’s not the best place for them to leave a paint delivery,’ Lyle said with a sigh. “Sam, would you mind helping us out?” 

Sam grinned. “Sure! Where do you want these boxes? I can move them for you.”

“There’s a storage room through the door behind reception,’ Lyle said. “But we’ll help.” 

“No, no. I got this,” Sam said a big smile. 

Lyle was about to argue when Sam squatted down to lift one of the boxes and they were all treated to the sight of Sam’s firm glutes flexing inside his tight slacks. 

“Maybe, we can let him do this?” Tate said with a barely suppressed moan. 

Maxy slapped Tate on the arm. “Subtle, Tate! Sooo subtle!” 

Sam was completely unaware as he put all of his focus on to the boxes. He carried the first one into the room behind reception and placed it as gently as he could on the floor. The box was incredibly heavy, which made him happy that he’d chosen to focus on strength at the gym recently.

By the time Sam had moved the fifth box, he knew he was sweating through his shirt, but he hoped that the guys wouldn’t mind given that he was helping them. 

“That shirt is like totally see-through, right?” 

“Keep it in your pants, Tate,” Maxy sniggered at the sight of Tate practically drooling. 

“You two are actually . . .”

Lyle was unable to finish his sentence because Sam had squatted down to get the next box and the strain on his tight slacks was finally too much for the seat of his pants. 


As the rear seam on Sam’s pants burst apart, the three guys were treated to the view of Sam’s bubble butt in his exceptionally tight lime green briefs covered in flowers. 

Hearing the noise, Sam immediately let go of the box and jumped to his feet. Surely, that wasn’t what it sounded like. He couldn’t have ripped his pants. He was at an interview! 

Sam tentatively moved his hands to his rump and was mortified to discover that all he could feel was his briefs. 

“My pants!” Sam yelled as he spun around so that the three guys wouldn’t see his undies. 

Lyle, Tate and Maxy tried to suppress their laughter at the sight of Sam blushing furiously. 

“I am so sorry. I have a big butt and these pants were kinda tight and I just wanted to help and I’m really sorry and . . .”

“Sam,” Lyle said kindly. “It was only an accident and we’re all friends here. Please don’t worry.” 

Sam visibly relaxed and shrugged. “Thanks, Mr Lyle. I’ll get back to work then.” 

Lyle, Tate and Maxy were stunned to see Sam turn around and squat down to retrieve another box, his coloured briefs on full show through the huge rip in the rear of his pants. 

“Is he going to finish moving these boxes?” Maxy asked with his mouth hanging open in shock. 

“It would seem so,” Lyle said, completely perplexed by the blonde Adonis. 

Sam came back and squatted down to retrieve another box, but this time, unbeknownst to Sam, the button on his slacks popped off and as he stood up with the box in his arms, the slacks slid down his thick, muscular legs to his ankles. 

“Oh, wow,’ Tate gasped at the sight in front of him. 

Sam moved to carry the box to the storage room, but with his pants around his ankles, he tripped and fell headfirst over the stack of boxes that remained, his brief clad butt in the air. 

 “What on earth is going on?” Stephan Morris, the Faculty Director, asked as he rushed over.

“Nothing to worry about, Stephan,’ the Dean said with a grin. “This is our new Facilities Manager. He’s just having a little difficulty with moving some boxes.”

Sam got to his feet and put his hands over the front of his briefs as he turned to face the growing group. “New Facilities Manager?” 

Lyle chuckled. ‘Yes, Sam. After this performance, it would be hard not to give you the job. You’re hired!” 

Sam grinned. ‘Thank you, Mr Lyle!” 

Tate and Maxy high-fived. ‘Welcome to the team!” 


What comes after dessert? More dessert! Here's a collection of some extra Cheesecake Boy goodies for you to enjoy.