The Unlucky Adventures of Steven Pt. 01

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Steven Caster's life is full of surprises.
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Part 1 of the 2 part series

Updated 01/27/2024
Created 01/24/2024
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The Unlucky Adventures of Steven Caster - The Beginnings

CHAPTER ONE

At the age of 18 after graduating from high school Steven Caster moved out of his parent's house in an attempt to live on his own and be self sufficient. He had worked all through school saving his money up to get an apartment which he shared with two other guys he had known from school that had been a grade or two above him. He enrolled himself into a local college and worked as much as he could to pay the bills.

Unfortunately by the end of the first year Steven was running low on funds and was considering moving back in with his parents. Steve's parents had told him time and time again how proud they were of him for being so independent and grown up which made it harder for him to admit defeat and ask to move back in.

Steven knew he would have to tell his friends soon that he would be moving out so they could find a new roommate to help pay rent. One night while he was at the apartment after work he mentioned to his roommates that he would soon be unable to pay the rent and would have to move out. A little over a week went by before the situation had been brought up. Steven had held off calling his parents because he didn't want to look like a failure but he knew he would have to call them now with the lease ending for him soon.

Just then there was a knock on his bedroom door and the voice of his roommate Josh could be heard through the door.

"Hey Steven you in there?" he asked.

"Yeah come on in." Steven replied from his seated position on his bed.

The door opened and Josh along with Steven's other roommate Lucas walked into the room. The two guys stood in the doorway with Josh running his hands through his redish-brown hair and Lucas with his left hand in his pocket and his right holding a paper bag.

"Hey guys whats up?" Steven asked looking at the two of them who were taller then him normally but even more now with Steven sitting on the bed.

"Well Josh and I have been talking about you not having enough money to stay and needing to move out-" Lucas said trailing off at the end as if waiting for someone else to finish the sentence.

"Yeah, I'll pay for the next two months but then I'm gonna have to go. Between work and school I just manage this right now." Steven explained.

"So -- we were thinking we could help you out a bit. We don't mind paying a bit more a month and let you stay here if you were willing to help us out a bit more around the apartment. Josh suggested.

"What? No guys -- would you really do that for me?" Steven said shocked at the offer.

"Of course -- but you are going to have to earn your rent almost like a second job for us." Josh added with a smile.

"Well what did you guys have in mind?" Steven asked.

Steven didn't like the idea of handouts but if he was working off the rent in some other way then that seemed fine. Plus that meant he didn't have to run back to his mom and dad looking like a failure for not being able to live on his own.

"So -- here is the idea that Lucas and I came up with. We will pay your rent every month in full in exchange for your services when we require them. That could mean a few times a week or a few times a day depending." Josh explained purposely being vague,

"My services? What do you mean?" Steven inquired a little confused and uncomfortable with the way Josh decided to word it.

Lucas then tossed the paper bag he had been holding to Steven. Who looked inside to see an assortment of odd things such as a girl's dress, a wig, handcuffs, tape, ringgags, and so on.

"What the hell Is this shit?! Steven asked even more confused and uncomfortable then before.

"We want you to be our slave -- sex slave" Josh replied bluntly.

"What?!" Steven said standing up from the bed and tossing the bag aside.

"Hey no pressure. It was just an offer. You don't need to take it but we are offering you free housing in exchange. You can stay here rent free and you don't have to move back in with your parents." Lucas added trying to justify their proposal.

"You still have two months to decide before you have to leave so you can think it over. We can even do a trial run or two to see if you are comfortable with it. Just let us know." Josh said.

The two older guys then looked at each other and headed out of the room leaving Steven alone with the paper bag to think about their offer.

--

Almost a full month went by since Josh and Lucas had made the strange offer to Steven of paying his rent in exchange for sexual favors. The younger guy had not brought it up to them once since their chat but knew that time was a factor before he had to move. He had tried several things including looking for better paying jobs to pay the rent but was unable. With only a month or so left he was running out of options. He really didn't want to move back in with his mother and father and look like a failure but there did not seem to be any other option -- unless he took the offer Lucas and Josh had suggested.

For almost a full week Steven thought abut the offer Josh and Lucas had offered. When he should have been sleeping he was looking up at the ceiling thinking about it and he had even searched the idea online many times. Steven read articles about sex slaves and servants even watching videos. The more he researched and pondered the idea the more interested he became. One late night he was in his bed on his laptop watching a video of a young man around his age being treated as a sex slave chained up and gagged, as he watched the video he found himself getting hard and then stroking his cock. He later fell asleep and had dreams of being used and abused by Lucas and Josh which only increased his interest making him think about the offer all day and night both while he was awake and asleep.

After a little over a week he decided to approach Josh while Lucas wasn't in the apartment and question him more about the offer and what it entailed.

"Hey Josh can I ask you some things -- about that offer you and Lucas made me about staying here?" Steven asked blushing as he sat down on a chair across from the couch Josh was sitting on.

"Sure -- what kind of questions do you have?" Josh asked rather calmly.

"I'm not quite sure where to start." Steven admitted looking down at the floor a bit embarrassed.

"Just ask whatever it is that you want to ask and don't worry about the questions being weird." Josh replied calmly with a smile on his face.

"Well --- when you two say sex slave what do you mean? I just feel like I need more details on the entire offer." Steven said with a slight stutter.

"Hmm--- well I think it is pretty straight forward. Lucas and I will pay your entire rent each month and in exchange you serve us. Sometimes that might mean that when we get home from a long day well ask you to give us handjobs or blowjobs, other days it might be a bit more then that." Josh said.

"But --I'm not gay" Steven replied.

"Everyone is a bit flexible when they want or need to be. If you want you can try a trial run for the next few days and see how you feel about it and if that works then you can agree if it does not you can go back to your parents" Josh said knowing that last part would hit Steven hard.

"Okay well how do we star-" Steve began to ask only to be cut off by Josh who lunged at him from the couch kissing him.

Steve was shocked but excited at the same time as he locked lips with the slightly older red haired man. Steve felt Josh's tongue force it's way into his mouth and thrash around. Steve could feel one of Josh's hands around his neck and the other sliding down into his pants grabbing Steve's hardening cock.

"Looks like someone is enjoying themselves" Josh said his fingers gripping Steve's excited manhood.

Steve blushed a bit as he felt Josh's hand around his erected dick. Josh began to stroke the young man as they continued to kiss and the grip on Steve's neck got tightened. Steve moaned as Josh stroked his cock while they remained on the chair in the television room.

"That feel good Steve?" Josh asked as he continued to play with the 18 year old's cock.

"Y=yes" Steve groaned his face beet red from embarrassment.

Josh continued to stroke Steve's rock hard erection faster and faster. Steve could barley contain himself as he bit his lip feeling his orgasm coming closer. With a loud gasp Steve climaxed shooting his hot white load up into the air and back onto himself. Steve took several deep breathes as he processed what had just happened. The brown haired man then looked as Josh who was looking back with a grin on his face. He then walked back over to is seat on the couch and unzipped his pants pulling them and his boxers down to reveal his own raging hard-on.

"I made you cum now return the favor" Josh said pointing at his dick.

Steve hesitated for a moment and then stood up from his chair and walked over to Josh. Steve then kneeled down in front of Josh and wrapped his hand around Josh's penis and began to stroke it.

"No. Suck my cock." Josh ordered.

Steve looked up at Josh who was staring right back. Steve took a deep breath and then moved his lips closer to Josh's manhood. Steve hesitated at first then slowly licked the penis like a popsicle not really knowing what to do. Then without warning Steve felt Josh grab his head and force his cock into Steve's mouth.

"Come on you have seen porn. You know what to do." Josh said.

Steve began to bob his head up and down as he licked and sucked Josh's hard cock. Steve gagged several times as Josh thrusted making his dick hit the back of Steve's throat.

"Good boy" Josh said tauntingly.

Steve continued to please his roommate for over half an hour until Josh stood up. The man towered over Steve as his hung package dangled right in front of his face while Steve remained kneeling.

"Close your eyes and open wide" Josh commanded.

Steve now obeying better did as he was told. Josh then jerked his own cock until he climaxed shooting ropes of cum into Steve's mouth and all over his face. Steve proceeded to lick his lips and swallow Josh's seeds.

"This is only a small part of what will happen if you agree" Josh stated looking down as the cum covered face of Steve.

"I think I would like to continue our trial for now" Steve said embarrassed of what he had just done.

"Okay we can consider the next few days to be a trial run. I'll let Lucas know." Josh said with a smile as Steven headed back to his bedroom his face still red as a rose.

--

Steve looked up at the ceiling as he laid down on is bed thinking about what he had just done. He had cleaned himself up but he still felt dirty. Somehow he felt what he did with Josh was wrong but at the same time if had felt so amazing. The young man looked over at the clock on his nightstand and noticed that it was already morning. He had been laying awake in bed for hours and was unable to sleep. Steve decided to get up and walk to the fridge to have an midnight snack despite it being past midnight. Steve walked out into the dark hallway of the apartment in his boxers and t-shirt and over to the kitchen. He opened the fridge looking through it for something to eat.

"Cant sleep?" asked a voice behind Steve.

Steve turned to see Lucas standing in the doorway linking the kitchen to the hallway.

"Ya." Steve replied looking back in the fridge.

"You been thinking about the deal and what you and Josh did earlier?" Lucas asked.

"What did he tell you?" Steve asked looking back at Lucas and blushing.

"Just all the good details. Like how he wacked you off and you sucked him. Apparently we are doing a bit of a trial run for you." Lucas said.

"Ya well -- umm ----" Steve stuttered.

"He also mentioned you looked pretty cute with cum all over your face." Lucas mentioned stepping closer to Steve.

"He did?" Steve questioned shocked and embarrassed.

"Yes, and I'm a bit jealous he got to play with you first." Lucas said.

"It was nothing personal. He was just here when I asked about the deal and well it just happened." Steve replied.

"Well now I'm here--" Lucas said moving closer to Steve.

Steve felt a chill run up his spine and then stitching coming from his cock as he became aroused once again. Lucas moved closer again pinning Steve against the counter. In one quick motion Lucas slammed the refrigerator door closed and moved in kissing Steve. Unlike before when Steve had been caught off guard by Josh he was more prepared for Lucas and accepted the situation faster as their lips and tongues locked together. Lucas wasted little time before getting Steve to kneel down in front of him on the cold kitchen floor. Steve obediently opened his mouth as Lucas revealed his large pulsing cock. The entire piece of man-meat was stuffed into Steve's mouth making him choke a bit.

"Be quiet. Lets not wake up Josh." Lucas said as he slammed his cock into Steve's mouth over and over.

Steve tried to be quiet but he was not used to sucking dick yet and continued to gag and choke. For several minutes Steve licked and sucked off Lucas covering his cock in spit and drool.

"You ever taken anything in your ass Stevie?" Lucas asked looking down at Steve as he continued to suck.

"noahhh" Steve mumbled with Lucas's cock still in his mouth.

"I think you lubed me up enough. Lets have some real fun." Lucas said pulling out and standing Steve back up.

Steve slowly pulled down his boxers revealing his tight virgin ass.

"Wow -- that thing looks so sweet." Lucas complemented as he turned Steve around bending him over the counter in the kitchen.

"Really?!" Steve asked blushing more.

"Yes -- I cant wait to get in there" Lucas said lining himself up behind Steve.

Steve felt Lucas grab is waist and press his hard cock up against his bare ass. Little by little Steve felt Lucas slide his cock into his ass causing him to let out moans. To stop Steve from being to loud Lucas quickly looked around for something to keep Steve quiet. Lucan grabbed a green apple from a bowl on the counter and put it in front of Steve's mouth. Steve opened his mouth wide and bit down on the apple using it as an effective dad as his roommate slid deeper into his ass.

"Mmmpphhhh" Steve moaned into the green apple as Lucas thrusted his cock in and out of his pet's ass.

As Steve felt Luca's every thrust causing him to moan and grunt he also felt Lucas wrap his arms around his body. Lucas had one hand around Steve holding his neck while his other hand grabbed Steve's hard cock and stroked it. As Lucas stroked Steve's hard dick and pounded his tight ass Steve's eyes rolled up in pleasure. Steve had never felt more insane pleasure in his life as Lucas took complete control. Pre-cum drizzled from Steve's cock and drool dripped from his apple gagged mouth as he lost control and completely gave in to Lucas.

"God you are ass is so tight. This is amazing." Lucas whispered into Steve's ear sliding his cock back and forth in his butt.

"Mmmpphphh" Steve whimpered in pleasure with beads of sweat dripping from his face.

With a quick series of rapid thrusts Lucas finally exploded inside Steve's read causing him to climax as well. Steve ejaculated onto the cabinets and floor near the counter he had been forced against. Lucas chucked and slowly pulled out of Steve the green apple still in the young man's mouth. Lucas turned Steve around to look at him and grinned.

"Did you enjoy that little ass pounding?" Lucas asked.

Steve replied with a nod of his head not even thinking of removing the apple from his mouth.

"Good. I really hope you agree to our deal, I think if will be fun for all of us." Lucas said as he fixed himself up arraigning his boxers and t-shirt.

Lucas then walked out of the kitchen and back into his bedroom leaving Steve standing in the kitchen with his boxers around his legs, cum dripping from his cock and ass, and the apple still jammed in his mouth. After a minute or two of just standing still Steve pulled up his boxers and headed to the bathroom where he decided to take a shower and touch himself thinking about Josh and Lucas and their offer which he was finding more and more enticing.

CHAPTER TWO

A few days had passed since Steve had agreed to the trial of the offer Lucas and Josh had made. He had already had a few encounters with both Josh and Lucas which were very pleasurable and with the deadline for his decision coming ever closer he had finally made up his mind. Before he had left for work he texted Josh and Lucas telling them that he wanted to discuss the deal when he got home from work that night. During his shift at work he got relies from both of them saying they would be at the apartment when he got home from work so they could talk.

To Steve it seemed that work could not go any slower. His heart raced as he anticipated the conversation between himself and his roommates. He was very worried about making his choice but also very excited. Both Josh and Lucas had always been helpful and kind to Steve which made this decision a bit easier to process. It also helped that they were both attractive men.

When Steve finished work he headed right t the apartment with tunnel vision. He unlocked the front door and walked in to see Josh and Lucas sitting down watching television waiting for him to get back from work. As calmly as he could Steve closed the apartment door and walked over to his roommates sitting down on the couch and chair.

"I have made my decision about your offer," Steve said feeling his skin turn red.

Lucas and Josh remained quite waiting for Steve to continue and say what his choice was.

"I will agree to your terms." Steve said.

Josh pointed to a small stack of papers on the table in front of the couch Lucas was sitting on.

"That is the contract. Once you sing that it will be official and will last one year. Once the year is up the contract expires and you and either renew it or figure something else out." Josh explained.

Steve walked over and looked at the stapled packed. The title page said 'Roommate Agreement' but he knew it was a bit more then a simple roommate agreement. Steve opened it up and began to skim through reading section headlines and skipping some areas.

"Once you sign that you cant back out of the deal." Lucas said to Steve as he turned the last page where he was expected to sign.

"I understand" Steve said grabbing a pen from a side table and signing and dating the forms.

"I guess this is official now. The contract begins at the start of the month. Until then you are not bound by any part of the contract." Josh explained taking the now signed document from Steve.

"So -- Ummm- what now?" Steve asked a bit squeamish.

"We can celebrate you signing the contract with us." Lucas said standing up and putting his arms around Steve kissing him.

Josh walked out of the room for a moment as Lucas and Steve continued to kiss with one of Lucas's hands reaching into Steve's pants for his already hard cock. Josh walked back into the room to see Lucas jerking off Steve and joined in. The three men made their way into Steve's room loosing clothes on the way. The three men quickly found themselves stripped of all their clothes with Steve bent over his own bed. Josh and Lucas wasted little time as they stuffed their cocks into Steve. Josh took Steve's ass while Lucas jammed his cock down Steve's throat. Steve was overwhelmed by the sensation from Josh and Lucas penetrating him from both sides. Josh and Lucas looked at one another and began kissing as they continued to stuff Steve's holes with their erect cocks. After what seemed to be an eternity of bliss the two men climaxed inside of Steve filling his mouth and ass with their seed. The men pulled out shooting a bit of their loads onto Steve's face and ass.

The men then began to get dressed as Steve panted and swallowed. Without saying a word Josh and Lucas both finished dressing and walked out of the room leaving Steve alone still panting from the excitement.

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