Making of a Sissy Whore

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Jeff finds out everyone has to earn their way.
1.9k words
4.25
46.3k
49

Part 1 of the 3 part series

Updated 06/09/2023
Created 07/16/2019
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Jeff was speechless as he sat in the chair across from his boss. Fired? He thought everything had been going fine. Sure, he was late a few times. Okay, maybe he had missed a few too many days after a long night of partying. But fired?

Well, he thought as he packed his few personal items, fuck them. This was a bullshit job anyway. He would get a better one within a week or two, right?

But in the back of his mind, there was a small fear growing. Jeff lived payday to payday and had about 38 dollars to his name at the moment. The bullshit job he was walking out of paid him in cash, which his boss had told him when they hired him 3 months ago was a good thing. Said it would mean he earned more and didn't have to worry about taxes. Now Jeff realized he would have a hell of a time proving anything for unemployment, or even work history.

He waited at the bus stop a block away from work, his small cardboard box of stuff sitting next to him as he thought through the situation. Rent was due in a few days for the room he rented from Kayla and Brad, but they would have to wait a couple of weeks till he got another gig. Wouldn't they?

As the bus pulled up, Jeff stood and pulled out cash for the fare. Okay, make that $36 for his total life savings. Shit.

Later that evening, Jeff sat on the couch in the living room of the 2-bedroom apartment and played xbox mindlessly, trying to forget about the situation for a while. Suddenly, the front door opened, and Kayla walked in holding a bag of groceries. Jeff looked over and waved, then continued his game. He knew he would have to tell her about the job thing, but it made him a little nervous. Kayla never really seemed to like him much. Though god knows he had tried.

She was hot as hell, with cocoa skin, gorgeous dark eyes and heavy tits that always seemed about to spill out of her top. Her thick lips and curvy hips made Jeff hard just thinking about them, and it didn't help that he hadn't gotten laid in months.

Jeff felt a light slap on his head, bringing him out of his spontaneous daydream about Kayla.

"Hey loser, remember rent is due this week. I need your money tomorrow."

"Hey Kayla" Jeff smile weakly, trying to think of how to tell her "about that. I, umm...lost my job today, so it might be a few weeks until I get another one."

She smirked. "You couldn't even keep that shitty job you had? You really are a loser, aren't you?"

"I told you I can get another one, I just need a little time."

"Well, the landlord isn't going to give us more time to pay the rent so you better figure something out or your ass is out of here!" Kayla was clearly upset and Jeff decided the best option was not to argue the point. After all, he wasn't even on the lease, so technically they could toss him out anytime they wanted.

He tried running through his options again, but stopped himself. He had already been over this a hundred times: no friends in town (let's be honest, no real friends back home either) and no "support network". He had only been here 4 months, having moved when Brad told him about the job opening he just got fired from. Jeff and Brad had gone to high school together, but when they graduated 5 years ago Brad had gone off to college and Jeff stayed in town.

He had stumbled from one part time job to another, and then seen a posting from Brad on Facebook mentioning that he and Kayla had moved to the city. Jeff asked him how the job market was and next thing you know he had made the move and agreed to rent a room from Brad and Kayla. The city was crazy expensive and he was getting off cheap at $400 a month for the room.

"Looooseeer...Hey!" Kayla was speaking and Jeff realized he had drifted away again "you owe me $50 for last week's groceries. You ate plenty and didn't buy shit!" She was holding out her hand, waiting for payment.

Jeff pulled out his wallet and grabbed the $36 in cash there. "Kayla, this is literally all I have..." as he spoke, she snatched the bills from his hand and turned to walk away.

"Hey! That is all my money. I need to look for a job and stuff." Even as he said it, Jeff realized how whiny his voice sounded.

Kayla turned her head and spoke as she walked away to her room "Not my problem. Everybody in this place has to pay their way."

The door slammed as she entered her and Brad's bedroom, and Jeff contemplated what just happened. Now he was truly broke. When he moved here, he sold everything he owned (which wasn't much) just to pay for the trip and expenses while he looked for a job. He could pack his entire personal belongings in a duffle bag...if he owned one. He sank back into the Xbox to escape.

An hour later, Brad got home. He gave Jeff a quick head not and kept going into their room. Jeff could hear them talking and Kayla raising her voice. It wouldn't take much to get Brad to agree on the idea of kicking Jeff out. They were just acquaintances from high school, not really friends.

In a while, Brad and Kayla came out and went into the kitchen to prepare dinner. They sat together on the other couch, to Jeff's left and began munching on hot dogs and chips. Brad had changed into a Deadpool t-shirt and basketball shorts, while Kayla had already prepped for bed in a silky robe that obviously had nothing on underneath judging from her hard nipples.

The smell of the food reminded Jeff he had not eaten all day and suddenly he was starving. Pausing the game, he walked to the kitchen and opened the fridge. Almost immediately, Kayla spoke up.

"What the fuck are you looking for, loser?"

Jeff hated how she called him that. "Just grabbing a bite" he said.

"The hell you are. Until you buy some groceries, there is no food in there that is yours."

He stood there, dumbfounded. Was she serious? Jeff closed the fridge and walked over to the couch, standing in front of them.

"Kayla, you can't be serious. I just lost my job today and you know I'm broke." He looked at Brad as he talked, his eyes pleading for support.

Brad swallowed and opened his mouth to speak "Bro, she's right. You've been here 4 months and you don't contribute shit. Which should mean at least you have some money saved, but no. You blew it all on partying and now reality is hitting."

Overwhelmed, Jeff sank to his knees there on the carpet and tears began to flow. "Please guys, I just need a little time."

Kayla chuckled and said "I told you he was a little bitch."

Jeff looked up and saw a strange expression on Kayla's face. She seemed almost...turned on? What the fuck? Was she actually getting off on his suffering?

He couldn't believe what she said next. "Suck his dick."

Jeff was so surprised, he stopped crying. "What?"

"You heard me. Suck Brad's dick. You do that and you can have dinner, plus we'll give you two days to come up with the rent."

She couldn't be serious. Jeff wasn't gay. Shit, Brad wasn't either...was he? As Jeff's mind tried to find something to hold onto, he watched Kayla reach into Brad's shorts and pull his cock free.

Jeff had never seen another dude's cock up close, but he knew right away that Brad was big. Kayla stroked it and spoke as it grew. "All you have to do is put it in your mouth."

Her voice had grown huskier, thicker with excitement.

Kneeling there, Jeff looked up at Brad and silently pleaded. All he got back was a grin and raised eyebrows.

Brad's cock had grown to probably 8 inches, and was now leaking a drop of clear fluid from the tip as Kayla stroked it. With her free hand, she reached out and grabbed the back of Jeff's head pushing him towards the dick. "Suck it, or get out" she said.

Jeff felt surprise as the velvety, slick head of Brad's penis touched his lips and coated them with precum. It was as if he were watching somebody else do this.

Then it became very real and he was fully back in his body as Kayla pressed harder on the back of his head, forcing Brad's shaft all the way in until it hit the back of Jeff's throat and he gagged a little. She then let him slide it back out, but immediately drove him right back down on it.

"Good boy, that's how you do it" she whispered.

Sliding around behind him, Kayla dropped to her knees and quickly pulled down Jeff's sweatpants to reveal his 6 inch cock. It hardened instantly with the touch of her hand, and sent waves of pleasure through Jeff's body.

It had been so long since he felt any touch there other than his own hand, he almost exploded on the spot. Kayla's other hand continued pressing on the back of his head, bobbing him up and down on Brad's stiff cock which was now slick with spit and precum.

Jeff felt Brad swelling in his mouth, the head filling the back of his throat every time he went down. At the same time, he could feel the urgency of his own orgasm building and his balls tightening in response to Kayla's soft hand jerking him off. Her other hand let go of his head, but she warned him not to stop sucking.

Brad said "Here it comes, bitch." He grabbed Jeff's head with one hand to control the speed of sucking, and as Jeff looked up at Brad's face he saw Brad was holding a cell phone and recording.

Right then, Jeff's orgasm ripped through him and he began shooting ropes of cum from his cock as Kayla continued to stroke. Brad spewed his thick, creamy spunk a second later filling Jeff's mouth until it leaked out the sides and ran down his chin. "Swallow it like a good girl" Kayla whispered.

He had no choice, as Brad held him forcefully onto the cock. Jeff swallowed again and again until finally the flow subsided. As Brad stopped the recording, Jeff let the dick pop free from his mouth and sat back on his heels to catch his breath.

Kayla raised her free hand, picking up a paper plate she had set on the floor in front of Jeff as she stroked him. On the plate was a single hot dog, drenched in Jeff's sperm. "Here you go, loser. Dinner is served." Brad and Kayla both laughed as he shook his head.

"Well, it's all your getting tonight, so you better eat it. If you don't, I am sure Brad can find someone to send that video to."

Defeated, Jeff picked up the cum covered hot dog and slowly took a bite.

"Looks like we found a job that it's okay for you to suck at" Kayla laughed "Maybe you can earn rent after all..."

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3 Comments
Claudia69Claudia69about 4 years ago
I Hope Jeff Likes Cum!!

I've never had a hot dog served with CUM.....Going to have to try!

rtsmith1976rtsmith1976almost 5 years ago
Poor jeff

Can't wait for this story to continue.

AnonymousAnonymousalmost 5 years ago
Hot

I wanna be in Jeff's position

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