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Bet Gone Bad (JennaRP & LustfulSins)

JennaRP

JennaRP

Star
Joined
Apr 28, 2018
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Casey’s alarm went off and he groaned as he reached for the phone to quiet it. He’d been dreading this day - Halloween - for over a week, ever since he lost the bet with his roommate. That allowed his roommate to choose Casey’s costume, and based on the shopping bags and packages that had been arriving at the apartment, the slender 20 year old already had a sinking feeling about all of this.

Those thoughts were only confirmed when he saw the bag waiting for him on his dresser. His heart pounded as he began pulling the items out. On top were some pink platform high heels in his size, a lump instantly forming in his throat as they set an awkward tone. Things only got worse as he pulled out a skimpy white satin thong, white thigh highs with pink lace tops, matching gloves and a skin tight pink dress with cut outs on the sides. It looked straight from a porno. If that weren’t enough, there was a bottle of hair dye that looked pink. His cheeks pulsed the same shade of pink as he couldn’t even look through the rest of the bag.

“No way. No fucking way” he mumbled. But the bet had been so hyped up, he couldn’t back out. He stormed out of his room, figuring this all had to be a practical joke and surely there would be a real costume somewhere else in the apartment.
 
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The day is here. Halloween, the day Casey would wear Max's chosen costume. They hadn't laid any rules regarding what could be chosen, so Max went ahead and picked out a skimpy pink dress and matching accessories for Casey. No question about Max's sexuality, he's absolutely gay. Whether or not Casey has picked up on that is another story altogether. As for the costume choice? Well, Max may be gay, but he still likes the way a dress can hug even a man's frame.

Max smirks when he hears Caseh's alarm go off. He had set the bag of items on his roommate's dresser last night while Casey was sleeping. And he can hear Casey cursing and heading for the kitchen of their apartment, where Max is currently making coffee. The platinum blond male turns and leans against the counter, grey blue eyes watching the doorway.
 
Casey saw Max in the kitchen, his cheeks still a rosy pink from what he’d just seen in the bag. He wasn’t entirely sure who Max was - they were just randomly paired together as roommates, after all. He figured the guy was maybe gay, or at least bi.. but he never seemed to make a pass at Casey, so it never came up. Casey was still telling himself it was a joke as he entered the kitchen.

“Very funny, Max” he said, hoping to see Max turn around and laugh at the trick. “Now seriously, where’s the costume I’m wearing tonight? The real costume!”
 
Max doesn't answer until his mug of straight black coffee is poured. He's still leaning against the counter, but now he holds hot coffee in his hands. There's a sly smile on his face. "What do you mean? I left your costume in a bag on your dresser."

Max raises the mug to his lips, sipping the hot liquid. Even though it's fresh and very hot, it doesn't seem to burn his tongue. He's smiling almost innocently, the twenty two year old taking pleasure in the frustration Casey is showing. "Come on, Casey, a bet is a bet. I'll even do your makeup for you."
 
Casey felt the air sucked out of him as Max showed no signs of joking. The slutty, girly costume was for him. The icing on the cake cake when Max so nonchalantly mentioned he’d do Casey’s makeup for him, leaving the brunette fidgeting, searching for some way out. If they weren’t roommates then he maybe could have fake an illness or just ghosted Max... but those were impossible as roommates.

“It’s gonna look stupid...“ he whined, though he wasn’t entirely sure. The clothes were all his size, even the heels. Max surely seemed confident. “Fine, I’ll make an appearance in that costume, but there’s no way I can wear those heels all night without breaking my neck.”
 
Max grins victoriously when Casey gives in. He can't wait to see the other male in the outfit. When the heels are mentioned, Max waves one hand. "Did you look through everything? There's pink flats in there too. But the heels will let you be taller than my 6'4, for once."

Max sets his mug down, tilting his head. "I'll be wearing a flashy purple suit and gold tie. Since you'll be dressing skimpy, I figured it only fitting we go as a paired costume. You'll be the slutty woman, and I'll be your pimp." Max laughs, smirking. "I bet we'll even win the costume contest."
 
Casey was pissed, but he had no leverage. If he backed out he’d be ridiculed and mocked... he convinced himself his best path forward was just to go along with it. Everyone could make fun of Max for choosing such a perverted costume. He could make that work, right?

“Fine” he muttered as he walked back, grabbing the hair dye and walking into the bathroom to take his morning shower. He applied it to his hair as he showered as the instructions said. He just assumed it was the cheap stuff from a department store or something.
 
Max is still smirking as he sets to making pancakes, a sort of peace offering. But he certainly plans to do more than just have Casey wear this pink outfit.ax had been eyeing up the handsome, almost pretty boy for months. He had just been very subtle about it, so Casey had never caught on. Max never came out and said he is gay, but he never tried to hide it either.

Pancakes made just as Casey is finishing his shower, Max sets the table. He would shower after breakfast. This evening, they would get dressed and head to the college Halloween party at the local club. They were sure to catch attention, but Max only wants Casey's attention.
 
When Casey dried his hair, he saw the the pink highlights had applied. He began to be concerned when he ran a hand through the mostly dried hair and no pink came with it, like the dye had seeped into his roots.

He wasn’t about to put the costume on yet when they weren’t going to the party until the evening. He tied a towel around his waste, as was customary, as he walked out and saw breakfast on the table. Least Max could do, he figured, walking out and having a seat, his shirtless chest showing as he took a bite of pancakes. “Thanks for making breakfast” he said, not trying to ruin the entire day - though the party loomed on his mind.
 
Max waves a hand dismissively, sitting down to eat with Casey. His eyes are looking at the brown and pink hair, the pink so vibrant. Casey hadn't complained about the dye, which means he hadn't seen that it's permanent. Max had purposely chosen pink due to it's stereotype as a female color. Humiliation is part of his goal, but with luck, alcohol, and maybe a little force, Max intends to to get Casey into his bed by the end of the night.

Once finished, Max stands and rinses his plate in the sink. "I made breakfast, so you get to wash dishes." Max makes a peace sign and leaves the kitchen. Shortly after, the shower can be heard running. As with every time he showers, Max leaves the door open an inch. It's an unspoken invitation to join him, whether Casey realizes it or not. Steam curls through the door.
 
Casey did his part with the dishes as Max walked off to shower. As he finished he walked back towards his room, noticing the cracked door. It had weirded Casey out at first, catching glimpses of his roommate in the bathroom... but now he just seemed to write it off as something Max did. Casey certainly wasn’t barging in.

He spent the majority of the day in his room, wishing something would happen the cancel the party. He even considered calling in a bomb threat to have the club closed down... but he chickened out.

In the late afternoon he decided he should start getting ready, if Max was to have time to do his makeup. He pulled everything out and began to get dressed, his nude, shaven body showing in his room as he situated the outfit. He’d started shaving his body years ago on the swim team and just never stopped. Now it seemed like he’d done it for the outfit.

He sat down and pulled on the stockings, feeling them glide up his legs to mid thigh. The gloves came on over his elbows. The thong... it was interesting. He wiggled some and felt the string push between his ass cheeks, his smallish cock stuffed easily in the crotch. The dress was a mystery as he eventually figured out how to get the straps. He put on the flats for now, looking at himself in the mirror and feeling the lump in his throat. He looked like a slutty twink or something as he tried to pull the dress lower.

Without even considering that he was dressed in the lewd outfit, he walked out. “Max! I think the dress needs to be... like... longer” he said, noticing that even with a slight bend, the bottom would ride up and show either the cleft of his ass cheeks or the crotch of the thong.
 
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Max's day is spent working on college classwork. He's a diligent student, top of his classes. Yet he still maintains a healthy social life. When it's two hours to the party, Max sets down his work and stands, stretching. Then he fetches the brand new glittery purple suit from its bag hanging in his closet. He can hear Casey moving around in his own bedroom.

When Casey calls, Max steps out of his room, dressed in a white button shirt, the purple slacks, and gold tie. The glittery purple jacket is still laid out on his bed. Max stops dead when he sees Casey and bites his lip. It takes a lot of self control not to show just how pleased he is with how his roommate looks. "It's supposed to be that short, Casey. Come on, I'll do your makeup now."

Max reaches out and grips Casey's wrist, tugging him into the bathroom. He sits the boy on the toilet, eyes briefly glancing down to watch the dress hem ride up. Then he moves away to his toiletries bag, where he had stashed the makeup he bought just for tonight. Max is no stranger to makeup; he's helped female classmates fix theirs enough times. Concealer, foundation, contour, highlight. Max gives Casey slightly thicker eyeliner to make his eyes appear bigger, then blends two shades of pink eyeshadow to make it look like smokey pink above the boy's eyes. Max pulls a few stray eyebrow hairs, adds the pink lipstick, then ends with a light spritz of setting spray. When he steps back, Max has to exert that self control again. "Damn. You look hot, Casey."
 
Casey could just feel Max’s eyes on him. It was hard to explain, but it was just a different feeling that he couldn’t quite categorize. As he was pulled through to the bathroom, he saw the bag with makeup practically spilling out of it. Enough cheerleaders and sorority girls had been to their apartment asking for damage control from Max for Casey to know his roommate at least dabbled in makeup, as strange as it sounded to Casey.

As he sat down, he could feel the dress riding up, the coolness of the chair on the bottom of his ass cheeks telling him as much. He took a hard swallow as Max went to work, fully expecting to look like some kind of whorish clown for everyone to have a good laugh at. But... when Max was done and called him hot, Casey was confused. He was spun around to look in the mirror and, for a second, he didn’t even recognize the reflection. His lips a plump, glistening pink. Eye shadow like it was professionally done in a magazine. His skin even looked soft and flawless. It was a shock, Casey just staring at it for a moment. He wasn’t sure his friends would even recognize him.

“Holy shit” he finally whispered, leaning forward for a closer look. Standing and looking at the whole picture, he did look like a kind of sorority slut with a pixie pink cut. He wasn’t quite sure how to feel about it, now feeling like he needed the heels to ‘complete’ the outfit. “Um... okay... well... I just need a little while to finish getting ready” he stammered as he walked back to his room. He slipped off the flats and, with some work, got the heels clasped on. They raised his ass up, lengthened his legs... it completed the look. After a YouTube tutorial and about 20 minutes of work, he could at least walk in them.

He walked out, getting perhaps a bit caught up in the startling moment and forgetting he was heading out in public dressed like this. “How’s that?” he asked Max, even so confident to do a small, slow turn for the full look, unaware his roommate had some very sexual thoughts when looking at Casey.
 
Max is smirking at Casey's reaction to his reflection. Perfect. He wants the boy to see how good he looks like this. It would still take a lot of alcohol to get past Casey's inhibitions, though. Max laughs quietly when Casey retreats to his room again. Max does the same, though it's mostly to fetch his suit jacket. One last trip to the bathroom to style his jaw length platinum hair back from his face, then he walks to the living room to wait for his roommate.

When Casey comes out in the heels, Max stands to watch him walk. Maybe a little unsteady, but he would get lots of practice tonight. And when Casey turns, Max's eyes drop to his ass. "You look so hot, Casey. We're going to win the costume contest for sure. Ready to go? Need me to carry your wallet and phone since you don't have pockets?"
 
Shit... his wallet and phone. He hadn’t even thoughts about pockets. How did girls manage? Oh, of course.. a purse. He didn’t have one, so it was only logical for Casey to grab his wallet and phone, then give them to Max to hold for the evening.

He walked back into his room, ass swaying as his hips shifted back and forth. He was starting to grow fairly nervous... he wouldn’t have his ID or phone. “What if we get separated? How will I find you or get home?” he asked, seeing that giving these items to Max would essentially require him to be glued to Max’s hip for the evening.
 
"Well, I guess we better not get separated then." Max smirks, eyes taking up and down Casey's body again. Then he holds out his arm with a grin. His next words are chosen purely to tease his roommate. "Shall we go, my pretty pink prostitute?"

Whether or not Casey takes his arm, Max leads the way out of their apartment, locking the door. Downstairs, then out of the building, Max heads for his classic Ford mustang, even holding the door open for Casey. "Just think how many guys will be watching you, girls too. The guys will want you, and the girls will want to be you."
 
Casey furrowed his brow as Max called him a pink prostitute and began walking out. Casey walked out of the door and heard the door lock... essentially locking Casey out until Max came back with the key. As such, Casey did take Max’s arm so he didn’t fall down the stairs in the heels. Max wouldn’t slow as they moved outside, Casey feeling the cooler night air on his exposed thighs and running through the thin material.

The mustang at least was much warmer as Casey slipped in. “Just a few drinks and then home” he said as Max teased him about how many guys and girls would be checking ‘her’ out. He wasn’t sure if he should believe it, but not a moment later a group of three guys walked by and all three seemed to gawk at the stocking clad legs and short dress as they walked by. Casey’s eyes widened as he pulled the door closed, keeping his thighs pressed together and tugging the dress down as far as he could... which was just to the tips of the stockings.
 
"Sure, sure. Just a few drinks." Max has no intention of keeping his word. He's going to get Casey fairly drunk first. Getting behind the wheel, Max pulls out of the campus parking lot and heads for the club. It's not too far, but Casey's in heels after all.

At the club, Max provides both their ID's to get in, and keeps Casey on his arm as they move through the crowd. There's some definite whistles, and a lot of stares. It's still more or less obvious Casey is male, but still. Max takes Casey up to the bar, standing quite close as he gets them started with a round of three shots each. "Cheers! It's an hour before the costume contest, so let's have fun for a bit."
 
As the car stopped outside the club, Casey was nervous. It was packed, hundreds of college students and young adults partying in revealing costumes. But as Max stepped out and started heading in, Casey had no choice, having to get out and catch up, taking his roommate’s arm. He could feel the stares, initially it seemed men were attracted but then some would notice he was actually a guy. Still, there were a LOT of stares and guys ‘accidentally’ bumping into him, their hands pressing against Casey’s ass. How did girls deal with this?

When they got to the bar, he could feel Max close to him... which was better than a stranger, he figured. Max - his pimp and bodyguard - ordered up a line of shots and Casey was shocked. He was definitely a lightweight when it came to drinking. Those shots would be enough to keep him at least buzzed for hours. But he wanted to be drunk to get through this evening. So he tossed the first shot back, seeing a light ring of pink lipstick left behind, as it was on the others as he drank them as well. His eyes clenched tight as the alcohol slid down his throat, the bartender thoughtfully giving him a cosmo to ‘wash it down’ with. He took a sip without even realizing it was more alcohol... but it sure did taste good.
 
Max laughs lightly at Casey's expression toward the shots. He hadn't actually been drinking with his roommate before, they usually have different friend circles. So Max doesn't know Casey's alcohol tolerance. He does pass his credit card to the bartender to open a tab. Most college kids aren't allowed a tab, but Max comes here often enough, he's known to be reliable. The cosmo makes Max grin as he gets a whiskey on the rocks for himself.

"See, Casey, the stares aren't so bad. You even got some whistles when we came in." With the bar crowded fast, Max stands sideways, facing his scantily clad roommate. Twice, young women come up to hit on Max, but he respectfully turns them down with whispers in their ears. What he whispers are his plans for Casey, and each woman just bursts into giggles as they leave.

At one point, a guy presses up against Casey's backside as he leans to order a drink. Max nearly chokes on his whiskey at Casey's expression, but doesn't come to his rescue.
 
Casey gave a hard roll of his eyes as Max talked about the stares and whistles. It wasn’t as bad as he’d anticipated, though the girls laughing and looking at him after talking to Max was definitely awkward. He was about to ask Max what he’d been saying to the girls when he felt a hand on his hip, being eased backwards until his ass felt something... hard.

He craned his neck to see a man, hulking and strong, leaning over to order a drink. “Sorry babe, let me just.. squeeze in here” he said, pressing harder against Casey as he ordered his drinks. Casey’s cheeks were a deep red under the makeup, frozen and unsure what to do. He thought about yelling at the guy, but that felt like an overreaction and would just draw attention. So, against his better judgement, he just endured it. “Sure... its, um.. pretty busy tonight” he said, using a higher pitched, softer voice. He found himself inching forward slightly towards Max, sandwiched between the two as the man behind worked to get the bartender’s attention. Casey was already feeling a bit tipsy from the shots, now just mindlessly sipping on the cosmo, only pushing him further down the hole.
 
Max's eyes move between Casey and the man behind him. The man still has his hand on Casey's hip as the other waves for the bartender. He finally gives his order, being told to wait a moment. There's about an inch of space between Max and Casey, so the boy doesn't really have anywhere to go when the man's fingers start exploring the slits in the side of Casey's skimpy dress.

With Casey's back to him, the man doesn't seem to realize the outfit is just a costume. It's convincing enough to his buzzed mind. Max is there watching, but again, doesn't come to Casey's rescue. When the man's drink is delivered, he pays the bartender, then turns his attention to Casey. "Come join me and my friends. We'll show you a good time." The man's hips roll, rubbing his groin, and his obvious erection, against Casey's nearly exposed ass. "We'll pay well."
 
Casey glared at Max, trying to nonverbally tell him to make the man stop touching his ass. But Max seemed to resist, making Casey fend for himself as the man kept touching and grinding, pushing him closer to Max. When the drinks finally came, Casey figured the moment was over, only to be pulled tight, an offer to come be a whore for him and his friends put on the table. He really was clueless that Casey was a guy. Casey was unsure if it was simply because he was drunk or if he truly couldn’t tell. From behind, it was even more difficult, but with Max’s work, Casey was feeling plenty of stares from in front as well.

When he felt the man start to grind, he let out a gasp and turned, pushing the guy back which only resulted in pushing himself back into Max. He quickly tried to calm himself and even faked a smile, not wanting to cause a big scene. “Sorry... my, uh.. Daddy here wouldn’t allow it” he said, nudging Max with his elbow to finally step in.
 
Max had, of course, heard what the man had said. He's trying not to smirk at Casey's situation, and only antagonized it when Casey spins and pushes himself back against him. Max drapes his arm around Casey, his hand low on the boy's abdomen. "Sorry, man. Casey's not working tonight. We're celebrating together."

The man looks disappointed, but lifts his drink in a cheers before heading off. The space is quickly filled by a pair of young girls, forcing Casey to stay up against Max. Seeing as Casey's cosmo is nearly empty, Max waves to the bartender for another round of shots for them. "Enjoying yourself, Casey?" Max's voice is teasing in the boy's ear.
 
The problem with getting drunk is that it encourages you to keep drinking. So, as Casey finished the cosmo, he couldn’t think clearly enough to know to stop himself. He felt good, the man walking off and, at least in Casey’s mind, the threat. He wasn’t thinking that the bigger threat was Max.

As the shots arrived, Casey just began drinking them, becoming certifiably drunk in the process. His speech would begin to slur a bit and his balance was noticeably off, having to lean more on Max to keep himself standing without swaying. He laughed when Max asked if he was enjoying himself. “It’s not so bad” he said back, his voice still soft.

“Alright y’all! It’s that time! Anyone entering the costume party, make your way behind the stage and line up for your chance to flaunt what you got!” the DJ said through the speakers.
 
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