Inadvertent Indiscretions by Jordan Skythe

Colt entered their dorm room wearing a towel and flip flops, with his dark hair messed in a way that could only result from a quick towel dry after a shower. Brandon gave him a nod while opening his backpack and silently registered their differences.
The first thing he did after a shower was blow dry his hair before ever leaving the bathroom. He liked his long hair and keeping it nice was one of the quirks his secret insecurities demanded. He also thought girls liked his long hair, though he hadn’t had much success lately, finding any specific girl who liked it enough to date him.
He munched on a breakfast bar as he transferred books from their desk to his backpack; maneuvering around Colt as he dried himself between their beds. Colt never seemed to mind what Brandon saw, and though he tried not to look, Brandon had seen everything for the time they lived together in these close quarters.
They were coming to the end of their third semester together and had definitely grown more comfortable with each other. Brandon caught himself smiling. They used to be just dorm mates. They were close friends now, though their relationship was anything but equal.
Colt rubbed his hair again with the towel and Brandon took the opportunity to secretly eye his just washed naked body as the towel blocked Colt from catching him. He knew how long Colt took to run the towel over his hair and diverted his eyes as Colt lowered the cloth.
“Got any plans for tonight?”
Brandon zipped his backpack and moved it from his bed to the desk chair. “The usual. …Nothing.”
“Man, I ain’t ever seen anybody in a slump as bad as yours.” Colt turned after buttoning his shorts. “Have you had a date since we’ve been roomies?”
He slouched over further as he sat on his bed, listening to his friend voice the thought stuck in his head for the last seven months. “Go to hell.”
“Hey. If it makes you feel any better, I haven’t had one since spring break.” He pulled his T-shirt over his head.
“Well, it doesn’t.” He raised his head. “And she only went out with you so she could spend the holiday break down the shore.”
Colt laughed. “Well, it was worth it. You shoulda seen her titties.” He raised his hands and made a feeling motion. “Absolutely gorgeous titties.”
“Don’t remind me.” He held his pillow to his face and screamed.
Colt waited for the shriek to end. “Alright. We can cry together tonight while we play video games. I’ll even spring for the pizza and beer.”
“You mean you’re not going to add to my running tab? …What’s the catch?”
“Hey, can’t a guy treat his Friday night date once in a while?”
Brandon threw his pillow and Colt raised his forearm, deflecting it. “I may make you pay for that later.”
He half smirked. “You’re all bullshit.”
“But you drink my beer and eat my pizza.” Colt stood, then grabbed his backpack and a soda from their tiny fridge. “See you after classes.”
“See you.”
Colt knew why he was being nice. He had something important to ask Brandon and had no idea what his reaction would be. He decided to soften him up with gifts befitting his college friend; pizza, a bag of chips, candy, and beer. And not just a six-pack. Tonight called for a case …good beer. Not the stuff Brandon bought for himself.
He snickered, knowing Brandon would question why he was being nice, but he also knew Brandon didn’t have the money to complain too loudly, which is another reason why he thought his idea was sound. Brandon needed the money as much as he needed to win the bet. Plus the perks were undeniable. Mansion on a coastal island. Free food and drink for the entire summer break. Swimming pool… Horses… Dinners out… Something to do all summer. Okay, it comes with a catch. What in life doesn’t?
Colt strolled toward the cafeteria for coffee. He could feel the wry smile grow on his face as he let his mind wander while looking around. Speaking of catches. Is there a better reason to love the change to nice weather, than the bevy of beauties who’ve put away almost all their winter clothes?
His head spun in every direction. He kept forgetting there were this many females in this school. Another caught his eye. Damn. One nicer than the next. He sighed. …and none of them willing to be my plaything. …Every shape and size and he was open to experimenting with any of them. He sighed again. Don’t tell me life is fair.
Spring always torqued him. It had happened for so many years, he knew it was coming. But that didn’t make it any easier to deal with.
His classes would be easy for the final couple of days. Things were wrapping up for the semester and assignments were either under control or already done; nothing to worry about on that front. And he’d reward himself by spending the extra time studying all the beautiful females wandering around campus. He exited his last class and followed an adorable ass in a delicately thin one-piece shorts thing. The flimsy material barely touched her skin. …Just the right amount of bra showing. No visible sign of panties, though with thongs, who knew?
She went straight at the street corner, toward the parking lot as he made the left and headed toward the liquor store. Damn. If she had turned, he would have asked if she was headed there and started a conversation.
Another missed opportunity, though he was optimistic. Maybe there was still time to meet someone by the end of the semester. He had a lot to offer but knew it would be no fun if he used his means to hook up. He always hated when he thought a girl liked him just because his family had some nice things, but he was running out of time. And not showing up at home with a guest for the summer was just flat out not an option. He hated that he loved this bet with his brother, and he hated that there was no way to break it without losing his entire manhood …not to mention, a fortune.
He was just so tired of always losing to him. Yeah, Tre was older, but not that much. And things were starting to turn in his favor. He was now taller than him, and his brother had a few extra pounds he didn’t have, which made him finally glad not to be him, but it took long enough. He had been chasing him in everything from sports, to grades, to girls for what seemed like his entire life, but he wasn’t about to lose their bet this year. He could always take the chance Carlton wouldn’t bring anyone home either, but it wasn’t worth the risk or the worry.

Brandon still wasn’t back when he walked into their room. He threw the snacks on the desk before loading as many beers as he could into their small fridge; removing a half dozen water bottles to accommodate enough to get them both good and drunk tonight. Plying Brandon with food and alcohol was just part of the sales pitch. His father didn’t teach him much, but what he taught, he taught well.
He stared at the fridge and the reality regarding how little time remained before the summer break, finally set in …which meant he knew he had one more shopping trip before he could put his plan into motion. He glanced at his watch then grabbed his car keys before heading out to buy more gifts.

Brandon walked into an empty dorm room, threw his backpack under the desk and spotted the plastic bag filled with snacks. He was always amazed at how Colt just couldn’t understand he didn’t have the money for luxuries like this. He sighed, then shook his head as he lie on his bed.
He couldn’t remember the amount he owed Colt. He knew Colt didn’t keep complete track either, but he felt funny always mooching off his friend. It was why he insisted Colt start their ledger. He knew Colt had the money. Hell, his truck alone was worth more than he made in his life so far, but it was the principle. He wasn’t a freeloader. He just wished Colt understood the feeling he got when Colt treated him without asking, since he could never reciprocate.
The door suddenly opening, woke him. “Hey, bud.” Colt threw a movie on his chest then bent at the side of his bed and stuffed shopping bags underneath.
“Damn, Colt. I was sleeping.”
“Not anymore.”
Among other shortcomings, Colt wasn’t very aware of those around him. He wasn’t ignorant or selfish. He was anything but. He just struggled noticing others. Brandon brushed it off though. He knew most guys their age were the same way. He actually thought Colt was doing better than most their age, especially considering his family structure. His father owned a few companies, a few houses, and more than a few cars, and figured most guys would be pretty full of themselves if their future looked as bright as Colt’s.
“What are you an old man? Need a nap before your Friday night?”
Brandon sat up. “I’m not tired as much as bored …and I outlast you almost every Friday night.”
Colt turned and grinned. “Would you like to place a wager on tonight?”
Brandon shook his head. “Does everything have to involve a wager with you?”
He raised a finger. “Speaking of which, we have to discuss a bet I have with my brother that could be very lucrative for you.”
Brandon chuckled. “How come every time you say that, you seem to make out with all the perks and I get far less than the sales pitch offered?”
Colt grabbed the folded throw blanket they spread on Brandon’s bed when they converted it to their sofa. “You seem to have done alright from our friendship over the last two years.” He pointed to the fridge filled with beer, and snacks resting on top. “…including tonight.”
Brandon’s head twisted. “Tonight’s share isn’t going in the ledger?”
Colt smiled as he held the blanket at the edge of Brandon’s bed. “Are you grabbing this with me or not?”
Brandon reached for the edge and they spread it over his comforter, then pulled sofa cushions from their various hiding places, and lined them up against the wall along his bed. “I told you this morning, tonight was my treat, didn’t I?”
Brandon’s voice softened. “You did, but I still always feel guilty.”
“Well, I don’t ask you to.” Colt opened the small fridge and removed two beers, then handed one to Brandon and each opened their beer before saluting.
“Besides, I have something you can help me with that’ll not only make us even, but also put some nice spending money in your pocket.” Colt slid the board they used as a table from under his bed, then placed it on the comforter and set his beer on it.
Brandon sat against the cushions before taking a long swig, then placed his beer on the nightstand separating their beds. He glanced at Colt staring at the TV mounted in the far upper corner. The air shaft next to it prevented Colt from watching unless he sat on Brandon’s bed.
He scanned the center walkway which led to the exit at the foot of his bed, and the wall cluttered with two thin metal closets separated by a laminated shelf with a chair and small refrigerator under it. They called it their desk, but only college dorm-mates would. The room was small but after two years, they considered it a comfortable set-up.
Colt turned on a sports news show and spread his arms across the tops of the sofa cushions. “I love Friday night. Don’t you?”
Brandon registered Colt’s inhale and sentiment. “Yeah.”
Colt finished his beer as they watched TV, then eyed Brandon. “Ready for another?”
Brandon drank the rest of his, then nodded. “Sure.”
Colt ordered pizza and they enjoyed another beer and a half before he breathed deep and placed his bottle on the makeshift table. “Do you have any plans for summer vacation yet?”
Brandon made a face and promptly finished his beer. “You’re a fucker.”
Colt laughed. “Okay, that might have sounded a little mean, but I promise it isn’t.”
Brandon sat up as if Colt’s promise meant he had to be on guard.
Colt smiled at his reaction. “Damn, Brandon. Am I that big an a-hole?”
Brandon chuckled and relaxed. “No. You’re actually a good guy, but sometimes our lives are so different, even your non-offensive shit makes my life seem fucked up. Sorry if there’s times, that makes me suspicious.”
Colt slid off the bed and reached for another two beers. “Well, I really do try to take care of you almost always. I’m sorry sometimes it doesn’t work out as good as I think it’s gonna.”
He opened both beers and held one toward Brandon. “Tell you what. I’ll let you think about this proposal for days …hell, we’ll negotiate this one until you’re sure you’re going to get what you want from it. …How’s that?”
Brandon sat up again. “Damn, Colt. I don’t mind the idea of taking care of you without getting something out of it. I already owe you more than I’m comfortable owing.” He paused, then smiled. “What is it?”
Colt inhaled before glancing at him. “I did a stupid thing two Christmas breaks ago that didn’t work out the way I hoped and it’s about to cost me a whole lot and I need your help to make it go from a beat-down to a win. In fact, right now, you’re the only one I can think of that can help me not get good and burnt and I want you to benefit if you decide to help.” Colt placed his fist on his chest. “Honest.”
Brandon’s eyes widened. “Christ, Colt. You’re like my best friend and fucking college roommate and even though I don’t offer much in return, I kind of always hoped there’d be something where you needed me and I could come through for you.” Brandon took two steps off their make-shift sofa and grabbed the bag of chips.
“And I wish I could think of another way, because this may still sound pretty fucking strange.” Colt gulped his beer.
“Colt. You’ve been taking care of me for almost two years. It’s okay if it’s good and strange.”
He snorted, “Hold that thought.” then stood and grabbed the bag of pretzels. He popped the bag open, and the pizza guy knocked as soon as he sat.
“I got it.” He jumped up, opened the door, handed the guy a twenty after taking the box, “Keep the change.” then laid the pizza on his bed.
He shut the door and faced Brandon. “You hungry or do you want to hear what I’m thinking?”
Brandon sat up. “We can eat later.”
“Need a beer?”
Brandon chuckled. “Colt. Are you really that nervous about telling me?” His eyes narrowed as he twisted his head. “Are you planning on paying me to take your place for a beat-down? Am I in for an ass-whooping from a bookie or some girl’s dad?”
Colt shook his head. “No. No, I promise. …No threat of physical harm. It’s just a little crazy, that’s all.”
“I’ve heard crazy from you before…” Brandon pointed at him. “But you said we can negotiate this one.”
Colt raised his hand. “I promise.”
Brandon motioned him to start explaining, and Colt inhaled. “Okay …what you get…” Brandon snorted and Colt paused before continuing. “…You come home with me and spend all summer break at my family’s shore house.”
“You know I can’t afford that. I can’t quit my waiter job and lay around all summer.”
Colt’s eyes widened. “Would you like to though …if you could afford to lay around all summer?”
Brandon’s voice turned sarcastic. “Who wouldn’t? But I’m not a Colton.”
Colt continued without acknowledging the snide comment. “I’ll not only match your summer earnings, but I’ll give you more than you would’ve made all summer.”
“You’re going to pay me to live at your family’s summer shore house?” Brandon shook his head. “You must really be in trouble.”
Colt’s breathing intensified. “And you get to enjoy all the amenities of the house …the pool, the horses, the local shopping …and dining out, as my mother likes to call it. And we’ll do things together …a lot of things together, my treat.” Colt motioned to the parking lot outside their dorm window. “You can even use my truck or one of the other family cars when we’re not hanging out together.”
Brandon laughed. “You’re a kick-ass salesman, you know that?” He shook his head. “Any other perks before I sell my soul to whoever you owe yours to?”
“That’s up to you, remember? If what I’m offering isn’t enough, then you tell me what other perks you need, and we’ll negotiate.”
“Damn, Colt. You’re good.”
“I wish I was as confident about my sales abilities as you.”
“Stop already.” Brandon smirked as if whatever he had to do was already agreed to, then motioned with his hand. “Well…”
Colt took the last sip of beer and placed it on the table. “I have to pee.”
Brandon hopped up. “Me too.”
They headed down the hall together, pausing the discussion completely.
When they re-entered the room, Colt opened the fridge and held out another beer toward Brandon, then opened his. “My brother and I made a bet a couple of years ago, between semesters while we were home, that I thought I could win easily, but winning the bet isn’t as easy as I thought.”
Brandon adjusted on their sofa. “What’d you bet?”
“Five thousand dollars.”
“Five grand?” Brandon raised his hand to his forehead. “Jesus Christ. What was the bet?”
“I know. But he’s such an asshole. That’s the number and I had no choice.” He reached under his bed and removed one of the large shopping bags. “The loser pays five grand to whichever brother brings home a girl for the summer.”
Colt cringed as he extended the shopping bag.
Brandon’s eyes narrowed as he took the bag and glanced inside. “You’re not suggesting…” The sweet fragrance confirmed what his eyes couldn’t quite identify.
Colt’s face contorted. “Please consider it?”
Brandon’s mouth dropped as his breathing intensified. “You want me to…” He looked in the bag again, then felt his heart jump. “You want me to be a girl… the entire summer?”
“There’s a lot of perks! More if you need more.”
“Colt, there’s no way I pass for an entire summer.” He shook his head. “No way.”
“So you’re not against the idea completely? You just don’t like how long?”
Brandon glimpsed at the items inside the bag. “It’s insane.”
Colt held up his hand. “First; you’re thin up top, light hair that’s already long, and your features are kind of…”
Brandon’s eyes widened. “Kind of what?”
“Kind of sharp.” Colt pointed at him. “Your nose is small and thin. …And your eyes are blue.”
Brandon squinted. “What the hell does that have to do with anything?”
“Colt’s voice lowered. “I just think maybe you’d make a convincing girl, that’s all.” He pointed to his laptop. “I found a feminization spa retreat online that isn’t far away, and I’ll pay for a full instruction vacation. They teach everything you need; hair, make-up, how to dress, how to walk …talk, and I’ll buy you all the clothes and shoes you want.”
“Girl clothes and shoes?” Brandon’s heart jumped as he registered the strange pleasure, the sentence produced. “Do I look like I want girl clothes and shoes?” His sentence sounded softer than he hoped.
“Please at least think about it a while? I just can’t lose another bet to that asshole; especially this one. I’ve been losing to him forever and I need to do whatever I can to not lose this one.”
Brandon felt his heart quicken as Colt pleaded, and the idea secretly intrigued him. He had thought more than once about dressing like a girl, but for a crazy one-night Halloween-type event, not an entire summer. There was an excuse and permission to do it for Halloween, but if he was exposed during the summer, how would he explain it? What was confusing him at the moment though, was the fact he found Colt’s repeated soft insistence curiously sensual. Would he have to do anything else as his pretend girlfriend? Would Colt make him explore all the aspects of being a girl?

Buy Book

Date Published 7/11/19

Author’s Website

Write a Comment

Your email address will not be published. Required fields are marked *