The Wardrobe Malfunction

The tales of sexy men put into compromising positions due to untimely wardrobe malfunctions.

  • Score 8.7 (28 votes)
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  • 1428 Words
  • 6 Min Read

Ashley

Ashley O’Shea is a strikingly handsome young man who is completely clueless about his sex appeal. A rather nerdy black college student who prefers to work out rather than socialize, his bespectacled baby face does little to disguise the fact that he looks like a jock on scholarship. His chiseled, 5’9” tall, swimmer-like frame is usually highlighted by his slim fit shirts and tailored slacks. Unfortunately, as a (still growing!) college student, Ashley hasn’t had the budget for new clothes… resulting in some interesting moments on and around campus.

You see, Ashley loves leg day and it shows. His jeans & pants sometimes lack the strength to contain his athletic thighs and supple bubble butt. In fact, that’s where this story begins…

* * * *

“Good Morning, Mr. Katerra.” says Ashley, as he gazes into a mirror. He’s slightly nervous about his first day at his new job as a brand ambassador for Rainbow Brewing Company, but you couldn’t tell. His boyish, innocent looking smile and firm shoulders exude confidence. Still, this is a new experience for him - one that doesn’t require his normally reserved self to remove any clothing like his last job. As much as he secretly got a rise out of being a local clothing model who was constantly being ogled by women and men alike, he was still a shy guy. Besides, he was too busy focused on other things like school to notice how easily he aroused others. As he checked himself out one last time before he headed out, he was pleased with how his white button down shirt accentuated his  chest and biceps. Even more pleasing was how his stretch skinny chinos hugged his every curve - no matter how well worn they were. He could’ve sworn that he saw a seam starting to fray - and there was definitely heavy wear in between his thighs - but he shrugged it aside as he began his journey to his office.

* * * *

Ashley parked his truck and took a deep breath. “Here we go.”, he said to himself, as he checked himself one last time in the reflection of his blue Ford F-150. He spotted a loose thread from his slacks hanging off of his left ass cheek. “Fuck! Glad I saw that!” he said as he yanked it off. Little did he know that his fabric was more threadbare than it seemed, especially with the unbearable stress of holding in his milk chocolate melons. A small hole appeared near the back seam of his pants, revealing a tiny speck of brown skin against the foreground of slightly faded and very taut black cotton blend. 

His stride into the office building was confident. His slacks strained with every step as this thighs and ass tested the limits of the already failing fabric. Many employees took notice as Ashley walked into the building, talking amongst themselves about the surprisingly hot guy who must unsurprisingly be the new brand ambassador. His new boss, Quincy Katerra, is known for this. He hires attractive men to be the face of his brewery, which caters largely to gay bars all over the Tri-State. He is bisexual himself, but seems to have an “eye” for male “talent” when it comes to promoting the brand. Ashley approaches Mr. Katerra’s office and without hesitation, the boss is sizing up his newest employee through his office window.

“Good Morning, Mr. Katerra!” Ashley says, more confidently than he practiced at home.

“Good Morning, Ashley! And please, call me Q. Mr. Katerra makes me sound so old.”, Q says with a bit of nervous laughter at the end. Q could barely keep his composure while trying to gaze at Ashley’s masculine beauty.

“Sure thing, Q! I mean… you DO look pretty young! Can’t be over 40!” Ashley replies.

“Ha! Thanks… I wish. Running this place makes me feel older than I actually am. Fortunately I feel a lot younger than my 50 years. Just gotta work out and take care of your health.” says Q. For an older man, Q is in great shape. His muscular frame proves that he’s a gym rat, possibly a former bodybuilder. Q’s slightly tan shade results from his tanning at the beach and his Italian background. Ashley notices his boss’s well kept body encased in his tight polo shirt that looks like he was poured into it.

“Good Lord, those arms….” Ashley thought to himself as he tried to focus on Q’s words and not his piercing hazel eyes. He caught himself as Q was explaining where his office was.

“So yeah… until we finish the expansion, your office is up there.” Q says as he points up a dark and steep stairwell towards the second floor. “Business is booming and we need more room. It’s getting pretty tight around here.” Q adjusts his pretty tight crotch as he watches Ashley begin to walk up the stairs. “Be careful… I know some of these steps are a little rickety.”

* * * *

As Ashley walks up the stairs, Q is closely behind him, helping to guide the way while getting an up close and personal look at his ass. “Those pants won’t make it through the day with all that ass.” Q thought to himself. He stayed close to Ashley, keeping his face within inches of that legendary ass - to the point that Ashley could have sworn that he felt his boss breathing on his form fitted backside. Ashley slips a bit and Q quickly catches him at his waist, slowly inching his hands further down until they’re resting on the top of Ashley’s ass.

“Sorry about that. Just didn’t want us to fall.” Q said as he quickly removes his hands and licks his lips.

“No problem. Thanks. These stairs are terrible!” Ashley replies. At the top of the stairs is a door that leads to other offices. Ashley reaches for it as Q is still moving forward up the stairs. Q’s face smashes right into Ashley’s ass, leaving a wet lip print on his left cheek.

“I’m so sorry!” exclaims Q while trying to wipe his saliva off of Ashley’s fabric covered rear. He’s not making it any better, just spreading it slightly and making it more noticeable. Ashley seems unbothered as he lets his new boss basically fondle his ass. “Uh… shit happens, I guess.”

Q finishes cleaning/feeling up Ashley and attempts to return to normalcy by getting back on track. “Umm… so yeah, there’s your office right here. All of your paperwork is on your desk and your itinerary is posted on your calendar. Did you have any questions?”

“Not yet, but I’m sure I’ll be bugging you in a few minutes.” Ashley says, oblivious to his boss’s huge bulge that’s attempting to bust of of his khakis. “Did you need anything from me?”

Q’s mind ran away with that question, but he was still able to muster up a “not at the moment” while still mentally salivating over Ashley’s ass. “Oh, and some important files are in the box on the floor. All of the information about your clients and customer base should be in there.”

“Okay, I’ll get right to it!” Ashley affirmed as he looked at the big box and secretly worried about over exerting his heavily taxed chinos. He didn’t worry too much, though, as he began to bend over to pick up the box. Q’s eyes stayed fixed on the chocolatey bubble butt nerd as he bent over almost seductively, nearly teasing his horny boss. It didn’t take long before an abrupt RRRRRRRIP filled the room, exposing Ashley’s jock strap-clad ass to a mentally excited boss. “Oh no!” yelped Ashley, as he dropped the box and moved his right hand to the largely parted seam that had been hanging on for dear life for years.

“Oh yes!” thought Q, as he quickly rushed into action. “This happens around here a lot. There should be an emergency sewing kit in your desk. You may need help with that.” he says as he stares into the dark brown abyss that’s between Ashley’s round cheeks. “That’s a pretty bad rip.”

“How bad!?!?” Ashley asks excitedly, hoping for the best but being fully aware of the worst case scenario.

“Well….” Q starts off, before placing his hand over Ashley’s ass, caressing the rip and gripping his left cheek. “I see that you’re a fan of jock straps, so there’s that.”

“Fuck!” says Ashley. “I’ll have to go home! I can’t walk around in these!”

“Relax… let me help you out with that.” says Q as he slips a finger in between Ashley’s cheeks. “Maybe we can fill this hole somehow…”

To be continued….

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