“I need to get myself hard,” Louis said.
“And this is doing it for you?”
“Yeah,” Louis said with a shaken exhale. He continued to fondle Jacob’s butt. He gently slipped a finger under the thin strip of lacy red fabric covering Jacob’s asshole, and then he pressed the tip of his finger into that very asshole. “Careful!” Jacob said, becoming tense again.
Louis didn’t reply. He just kept fondling. Jacob could hear him breathing louder and louder. The tension in the room was thick. Jacob tried closing his eyes and counting in an attempt to get his mind away from the fact he was about to be fucked by his best friend. And then he felt the thick warm erection sliding up between his butt cheeks—and reality sunk in: he really was about to be fucked in the ass by his best friend.
CHAPTER XII
There were no condoms in the room, but there was a small bottle of lubricant in the nightstand drawer. Louis squirted a healthy amount on his cock, and then he squirted some more between his friend’s butt cheeks. He felt awkward pressing the tip of his cock against his buddy’s tiny hole, but he was able to calm himself down by looking at Jacob on the bed.
Jacob really did look like a chick. In fact, he looked more feminine than the trans chick he’d been fucking all week. Jacob looked hot. He had the perfect figure and the best ass he’d ever seen. Even his face was amazingly impressive with a bit of eye makeup. How had Louis never noticed before?
“Ready?” Louis asked with his tip pressed against that lubed-up hole.
“I’m ready for it to be over with,” Jacob said. “Just do it.”
Louis began to press in. He couldn’t believe it was actually happening. Did Jacob really want to be in the fraternity this badly? Or was he just doing this for Louis? Jacob knew how badly Louis wanted to be in the coveted frat—was he really sacrificing everything so that Louis could realize his dream?
Louis penetrated Jacob’s asshole. Jacob clenched for a moment and then relaxed. Louis waited until his friend was ready before he sunk in any deeper. It only took a few seconds. Soon enough, Louis had half of his slick cock in his dolled up buddy’s asshole.
“You’re so tight,” Louis said.
“You’re so big,” Jacob said. It sounded like he was clenching, or trying not to moan.
“It feels good,” Louis said. He slowly started to pump his cock back and forth, in and out, feeling Jacob’s asshole stretching wider and wider. “Really good.”
“Yeah,” Jacob agreed, to Louis’s surprise. So Louis let his cock sink a little deeper. Jacob didn’t oppose, so he sunk his cock even deeper. Then, Jacob started to moan gently. He really was liking it. Louis reached down and stretched Jacob’s butt cheeks apart so he could watch his cock sliding in and out.
“Don’t stop,” Jacob moaned. He was clutching the bed sheets, his heeled legs bending as his feet reached back towards his bum.
Louis came down harder and harder, filling Jacob deeper and deeper until his pelvis was slapping against Jacob’s bum. Now Jacob was moaning loudly—groaning and squirming and clenching and trembling. He was in a state of ecstasy Louis had never witnessed before. And he found himself feeling a bit jealous.
“I think I’m going to come,” Louis said, his own voice strained.
“Come inside of me,” Jacob begged. He started pushing his butt back into Louis’s pelvis, making sure he was getting all of that cock inside of his body. “Harder. Fuck me harder.” So Louis held his friend tight and fucked him as hard as he could, pounding his ass, making his pelvis slap loudly against Jacob’s soft butt cheeks.
“This is it! I’m coming!” Louis groaned. Jacob screamed and then Louis unloaded in a series of euphoric blasts. It felt amazing. Louis trembled all over and then he stumbled back, keeping his gaze glued to Jacob’s butthole so he could watch the billowing creampie. “Holy shit,” he muttered under his breath.
The bedroom door swung open and Roger stood in the doorway with a pair of Kappa Delta Pi baseball caps. Behind him stood every member of the Kappa Delta Pi fraternity. “Congratulations to our two newest members!” Roger announced. The members all started cheering. They filtered into the room and gave Louis a firm pat on the back. One of them helped Jacob to his heeled feet. They gave him a pat on the back too. It was strange—as if they didn’t care that their newest members were naked and dripping with sweat and cum. Roger put a cap on Louis’s head and then he put a cap on Jacob’s head, over his wig. Jacob looked even cuter with the cap on.
“Tonight, we celebrate. But now, you guys need to get cleaned up. I have a feeling you’re going to have a lot of fun over the next few years. And hey, if you guys want to share a bedroom, that’s cool. How do you like this one? Is the bed okay? It’s only a king—we can have a California king put in, if you’d prefer.”
“I—I think this is fine,” Louis said. He looked over at Jacob, who was still smiling with rosy cheeks. Maybe they would share the room together. Maybe Jacob would dress up more often—or maybe he could just get dolled up all the time. Maybe he could be the first Kappa member who was also a Kappa Girl.
Louis took a quick shower and then he got dressed in the Kappa adorned suit that was laid out for him. Once he was dressed, the senior members came into his room and lifted him up. They carried him outside and announced him to the crowd of mostly women who came to see who the new Kappa members would be.
Jacob was carried out a minute later. He looked over at Louis with a big smile. “Maybe later you can help me pick out an outfit for tomorrow,” he said. “I’m thinking a skirt, but I really don’t know what would look best on me.”
Louis couldn’t stop the smile from crossing his face.
THE END
BECOMING A TRAP
Ernie just lost his job and his car in the same week. Now, he doesn’t have any money to pay his rent, so it’s looking like he’ll be losing everything. And then he gets a mysterious package, offering him a few hundred bucks just to get dressed up like a girl in the comfort of his own house. He accepts the offer and gets dressed up in the clothes that came with the package.
A few days later, he gets another mysterious offer—this time the sender is offering more money for a slightly more difficult task. And the offers keep getting bigger and the tasks keep getting more difficult.
CHAPTER I
Ernie was realizing very quickly that he’d been given terrible advice. William, his co-worker, had told him, “If you go into the boss’ office and demand a raise, he has to give you one. It’s like a rule with HR.” Ernie was hesitant in believing William, but Ernie was also desperate for money. He was behind on rent and he still hadn’t finished paying off his mechanic—his car was still stuck at the shop and they refused to release it until he paid the full amount.
So Ernie walked into his boss’ office and demanded a raise, and an advance on his salary. And for an entire minute, his boss was completely silent, staring into Ernie’s eyes with a fiery vengeance. “I—Is that okay?” Ernie asked.
And it wasn’t okay. Ernie’s boss looked like he was about to blow a fuse. So Ernie took a step back. “I was told that, uh, if I asked, you had to give me a raise. William told me—he said it’s a rule with HR,” Ernie said. But his boss remained silent, making the horrible moment sting even more. “I don’t want a big raise—maybe just five grand a year. I work hard—you even told me the other day that I was a hard worker.”
“You’ve been here for five months,” his boss said, finally breaking his silence.
“Yes, sir,” said Ernie.
“And you think you deserve a raise? After five months? Most guys don’t get a raise until they’ve been here for over a year. And you think you deserve a raise after five months?”
Ernie felt beads of cold sweat teasing the back of his neck. “Yes, sir,” he said.
“Well you don’t, so you aren’t getting one,” said the boss.
Ernie figured that was his cue to leave the office—cut his losses. But a stubborn little part of him kept hi
m standing in that room.
“Is there more?” the boss asked.
“Well, it’s apparently a rule with HR, that you have to give me a raise if I ask for one.”
“There’s no rule. You were lied to. Now get out of my office.” The boss’ face was beginning to turn a shade of pink. His lips were pressed thin and his hand was inching towards the phone, probably to call security.
“Are you sure about that? Because I’ve heard of rules like that with other companies, and William said—”
“—I don’t give a fuck what William said. Get out of here. You’re fired. I don’t want to see you here again. Go!” He started waving his hand, motioning Ernie towards the door. But Ernie was frozen stiff now, too afraid to move. Was his boss serious? Could he really fire him over this?
Apparently, his boss could fire him for whatever reason he wanted. Ernie hadn’t been with the company for long enough to get the same rights as other employees. After six months, employees earned three strikes, but before six months, they were technically on probation. Ernie learned all of this when he went from his boss’ office to the HR department, to find out if there really was a rule saying whoever asks for a raise gets a raise. “Of course there’s no rule like that. Then everyone would just constantly be asking for raises. Who told you that?” the HR manager asked.
“William,” said Ernie.
“Well why did you listen to William? Why didn’t you just come and ask us here?”
Now everyone in the HR department was staring at Ernie, waiting for his response. But Ernie had no response. He’d been duped. William was probably just playing a prank, which ended up getting Ernie fired.
So Ernie found himself shuffling out into the street with a box full of personal items in his hands. It was a long subway ride back to his neighbourhood, and then it was a long walk from the subway to his basement suite at the edge of town. Ernie didn’t waste any time. As soon as he was home, he started searching through job listings, hoping to find a quick replacement so he could pay his rent before being evicted. After an hour of searching, he found a job with decent pay as a delivery driver. But there was one problem: he needed a car. He called the manager of the delivery firm regardless. “You sound qualified—why don’t you come by in the morning for an interview?” the manager said.
So Ernie got a good night’s sleep and then he took the subway to the delivery headquarters. The interview went smoothly, until the manager said, “And of course you have your own vehicle, right?”
Ernie felt a lump growing in his throat. “Well, I do have my own car, but it’s stuck in a shop at the moment.”
“It’s broken?” the manager asked.
“No, it’s fixed, but I just can’t get it out until I pay the bill. And I’m kind of short on cash at the moment.”
“I see,” the manager said. “But you’ll have the car by Monday, right?”
Ernie was silent for a moment. “If I do have the car by Monday, do I have the job?”
“If you want the job, sure,” the manager said.
“Great. So, um, could I get a bit of an advance on my pay, just so I can get the car out of the shop?”
The manager was silent—a silence which Ernie was all too familiar with. “You’re kidding, right?” the delivery firm manager said.
Ernie forced a big smile.
“You know, I just remembered we have a few more guys coming in for interviews today. We’ll be in touch once we make a decision.”
“A decision—but you just said if I have the car by Monday that I can have the job,” Ernie said, his heart plunging into his gut.
“Right, but then I remembered we have other guys coming in. It was nice meeting you, though.” The manager motioned towards the door, and Ernie realized he wouldn’t be hearing back from this particular company.
Ernie stopped at the mechanic on his way home. He had no money but he was hoping he could make some sort of arrangement. He figured he could pull up to the delivery firm with his newly fixed car and convince the delivery firm manager to give him a job. But the mechanic refused to release the car. “I’ve made this mistake before,” the mechanic said. “There’s a guy out there who still owes me five hundred bucks—from two years ago. I’m not making that mistake again.”
“Please. I don’t have a job right now and I need the car to get a job. You’ve got me in a really tough position here.”
“I’ve got you in a tough position? You’re the one who took your car in to get fixed without having the money to fix it! You did this to yourself.”
“I’m begging you,” Ernie said. He was ready to drop to his knees, if that’s what it took. He was ready to kiss the mechanic’s oily shoes. He was ready to clean around the shop on the weekends if it meant getting his car back. But the mechanic wasn’t interested in giving Ernie a handout.
So Ernie was stuck walking back to the subway. He had to check his bank balance on his phone to make sure he even had enough for the subway fare. He did have enough, but barely. A few more subway rides and he would be officially broke.
CHAPTER II
Francis was stuck in traffic with a girl he wished he would have never asked on a date. She seemed nice in the bookstore, when he first talked to her, and she was incredibly polite and cheery on the phone, when he called her and asked when she was free. But as soon as he met up with her at that café, she was like a completely different person.
She only wanted to talk about herself. As soon as Francis started talking about himself, her face would become blank and it wasn’t long before she was pulling out her phone to text with her friends. The only time she seemed interested in Francis was when Francis was talking about his wealthy parents. As soon as she learned that his parents were still relatively young and healthy, her attention went back to her phone.
Francis ended the date early, by lying about being tired. His date was happy for the date to be over, but freedom didn’t come so easily. Francis started driving her home and then they immediately got stuck in traffic—cars were stopped while a late-night marathon ran through the neighbourhood.
They didn’t talk much while they sat in the car. Thirty minutes went by without a word spoken between them. Francis finally broke the silence by asking, “Is it this left or the next left?”
“It’s the next left,” his date said, and then they went back to being silent. They were on the highway when Francis’s car broke down. He was able to pull it over before it stopped completely and shut itself off. “What the hell is going on?” his date asked. “It sounds like your car is about to explode.”
“It’s been doing this since I had the exhaust fixed two years ago,” Francis said. He pressed his forehead against the steering wheel.
“Well? Aren’t you going to call someone?” the date asked.
“By the time someone gets here, it will be fine. It just takes twenty minutes to cool down.”
“We’re stuck here for twenty minutes? Are you kidding? I don’t even get data out here,” Francis’s date said. She stepped out from the car and tried holding her phone up to get data, so she could continue surfing Instagram. Francis stayed in the car, happy to be away from his torturous date.
She wasn’t the first bust of a date he’d gone on; in the past two months, Francis had gone out with nearly a dozen girls, and he’d found a legitimate reason to hate all of them. One girl was cute and nice, but she had an unusual obsession with cats, and she smelled like cat urine and Francis was too afraid to tell her. It didn’t help that Francis was terribly allergic to cats.
Francis felt relieved once his date was finally dropped off at her home. But once she disappeared into her house, he felt strangely depressed. It was starting to seem like he was never going to find himself a nice girlfriend. Maybe the girls he was dating weren’t all crazy—maybe he was the crazy one. Or maybe he just had ridiculously high standards that were unreasonable.
On his way home his car broke down again. While he was sitting on the side of the highway, he wo
ndered if it was time to settle with the first girl who made herself available. So what if she likes to talk only about herself? So what if she wants to own sixteen cats? Who was Francis to judge?
While Francis was sitting on the side of the road, his phone rang. It was an unknown number. He answered. “This is Francis. Who’s calling?”
“Hey Francis, it’s Tim, the mechanic who fixed your car. I had a customer come in today who made me remember that you still owe me money. I’m still waiting on that cheque you said you would send.”
“I told you I wasn’t going to send any money—the car isn’t fixed. It’s worse now than ever. In fact, I’m sitting on the side of the highway now waiting for the exhaust to cool down so I can drive the damned thing home.” Francis was on his feet now, pacing back and forth, trying to calm himself down. It had been two years and this damned mechanic was still trying to extort him. “So you can either fix my car properly, or I’m not paying a dime.”
“I fixed your car. If there’s something wrong with it, then it’s something you did after picking the car up from me,” the mechanic said.
“Something I did within five minutes of picking the car up? You really think that?” Francis nearly crushed his phone in his hand.
“Maybe—why not? I’m going to get that money from you—and you’re going to regret stiffing me.”
“I’m hanging up,” Francis said, and he hung up. He still had another five or ten minutes to wait before his car was driveable—which gave him five or ten minutes to pace up and down the road, letting off a bit of steam.
Francis unfortunately didn’t have the money to fix the car properly, with a proper mechanic. He probably had enough in his savings account back when he first took the car in to get fixed, but he’d been losing money faster than he could make it since then—now he didn’t even have enough for the parts, never mind the labour.
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