Freshman Project: Jason

[Rillion]

Freshman Project: Jason (Part 5)

 

Jason crawled out of bed, his hard five inch cock tenting his dark blue cotton briefs. Growing up his parents had only purchased plain white briefs, but one of the first things he had done after arriving out west was to go to the local department store and buy some new clothes. It had cost him quite a bit of his savings, but he didn’t want to look like a total hick. Blake had mentioned taking him shopping soon up in the city. Jason just hoped he could save up enough money from his job in the cafeteria to afford some sexy clothes for Blake.

Jason’s roommate, Dennis, had a Friday morning class, so Jason had a few moments of privacy in the room. He picked up the plain black backpack Blake had sent home with him and set it on the bed then plopped down next to it. He opened it up and dumped the contents onto the bed. There was a dildo, a butt plug, an enema bulb, some lube, one of Blake’s dirty jockstraps, a baggie with a few gummy weed edibles, and a short note. The dildo was probably about five inches long and thinner than Blake’s thick cock. He picked up the note, it read ‘I will text you with instructions, enjoy’. He picked up the jockstrap and give it a long sniff, his already hard cock started leaking pre-cum as he smelt the combination of Blake’s musk, piss, and cum. His phone chimed with a notification, interrupting his enjoyment of Blake’s scent.

Jason picked up his phone and saw he had a notification that he had received a text from “Master”. He remembered that at the end of the night as Blake was sending him home that he had asked to see his phone for second so he could enter his information. Jason unlocked the phone and read Blake’s text.

Master: Be at my place after you are done with work on Monday. Text me when you’re on your way. I have a swim meet this weekend. I expect you to use your two new toys over the weekend while I’m away. Do you remember the homework I gave you Boy?

Jason thought back to and recalled Blake telling him that he needed to research how to clean out his ass and also figure out of if he was going to let Blake bareback him when his ass was ready. Jason tapped out his reply.

Jason: Yeah, learn how to clean my ass and decide if I want you to fuck me without a condom

He waited several minutes and was surprised Blake had not responded. He read the message again and realized his mistake.

Jason: Yes Master, I remember. Sorry Sir

Master: Good Boy See you Monday

Jason checked the time and realized he had about an hour until Dennis would be back from his class, so he went to his desk and opened up his laptop to start on the first part of his homework assignment for Blake, researching how to douche.

Unfortunately with classes and work, Jason was not able to put the research to use until Saturday. Fortunately though his roommate chose to drive back to his hometown of Santa Cruz that weekend, so Jason had the room to himself from Saturday morning to Sunday evening. After he got done with his lunch shift, he returned to his room for an afternoon and evening of exploration. He ate a weed gummy and took the douche bulb Blake had given him and went to the showers.

The dorm showers were individual showers with doors so they had some privacy. He followed the instructions he had found on the internet and cleaned himself out. By the time he was done, he was starting to feel the effects of the edible. He went back to his room, locked the door, and fired up his laptop. He loaded up some of his favorite porn that he had downloaded then grabbed the dildo and lube. He put a towel down on the bed, piled up some pillows so he prop up his back in position to reach down to play with his ass as he watched the porn on his laptop.

Jason had played with his ass a few times when he had a brief opportunity to be alone at his family’s house. He would use a carrot and some vegetable oil. Afterwards he would destroy the evidence by chopping up the carrot and dumping it in the garbage disposal. So he knew the basics, and even though the dildo was not very big, it was thicker than any of the carrots he had used. He poured some lube onto his fingers and started working the lube into his ass.

The videos he had loaded up were all bareback, most were twinks in twosomes or threesomes, and a few had older muscle men fucking skinny twinks. Jason had originally started out watching videos were the guys were using condoms, but one day he was feeling especially horny and had clicked on the bareback section of the website. He soon discovered that it was so much hotter to see guys fucking bare than using condoms. There was also a difference in the way the videos were filmed that he found hotter. The bareback videos showed more close ups of the tops’ cocks thrusting in an out of the bottoms’ assholes. This turned Jason on more than the full body shots that didn’t show the penetration which were more common in the videos with condoms.

Jason felt the effects of the pot, it was making him feel his horniness in his body. He pressed the head of the realistic cock shaped dildo to his ass then relaxed his ass as slipping the lubed up head into his still virgin ass. It hurt a bit as it stretched him. He pulled it back out, applied more lube, then slipped it in again. He did this several more times, slipping the head in then pulling back out and putting it in again. Eventually he was able to get the head in without feeling any pain. A small puddle of pre-cum had leaked out of his hard cock and pooled in his belly button. He reached down with his other hand, scooping up the pre-cum with his fingertips then licking them clean.

He fucked himself with the dildo for a long time, making sure not to play with his stiff cock, because he knew if he had an orgasm he would not want to continue. He also pulled Blake’s used jock strap over his face with the pouch covering his nose and mouth. Eventually though the dildo sliding back and forth across his prostate had him on the brink of cumming. He was tempted to jack himself off, but wondered if he could bring himself to cum hands free. He sat up and put on a video with his favorite scene, queuing it up to the climax scene then pressed play. He leaned back and started thrusting the dildo into his loosened up ass hard and fast, drilling his prostate. On the screen in front of him he watched three older men taking turns cumming in the ass of a young twink, the twinks ass getting cummier and cummier, as the each daddy shot his load into and on the hole, using their cocks to feed the escaping cum back into the young man’s hole. Jason shoved the dildo in all the way to its base as he started to cum. On the screen in front of him he watched as the cum loads of three men leaked out of the gaping hole of the young twink. Jason’s own cum shot out of his throbbing cock for his first, but certainly not last, hands free orgasm.

After he had recovered from his orgasm, Jason grabbed the butt plug, lubed it up using his own cum that had sprayed across his chest, and then worked the plug into his ass. It was thicker than the dildo, but Jason only felt a slight discomfort as the thickest part of the plug stretched his ass ring as it slide into him. He cleaned up the room a bit then spent a few hours listening to music and watching Tik Toks as he let the effects of the pot gummy wear off. He grabbed a light meal at the cafeteria for dinner, then returned his room, took another gummy, cleaned his ass out again, then fucked himself with the dildo for the rest of the night while watching bareback porn. He did not feel like he could cum hands free again and instead wanted to see how many times he could cum that night while fucking himself with the dildo. He finally gave up after his third cum of the night, fourth of the day, as both his cock and his ass were starting to get sore.

On Sunday, Jason worked the morning shift, then alternated between using the dildo for a bit, then putting the plug in and studying for a bit. Since he had to do some classwork he refrained from taking another of the gummies. Also after cumming so much yesterday, he refrained from cumming, instead saving up for tomorrow when he would get to hang out with Blake after class. He made sure he had cleaned up and aired out the room before his roommate returned that evening.

Monday morning when Jason woke up, he saw there was another text message from ‘Master’. ‘Clean your ass out and wear the plug when you come over today. Don’t worry, you aren’t getting fucked today, you haven’t earned it yet’. Jason worked the breakfast shift, then had a late morning class. He skipped lunch, instead using that time to clean himself out and put the plug in before his afternoon class. He wanted to get to Blake’s apartment as soon after his class as possible so he could spend as much time with his new master as possible. It was hard for him to focus during class with the plug up his ass and his cock hard. He counted down the minutes until he could get of there and see Blake.

Finally what seemed like the longest day of his life ended and Jason was standing outside the door to Blake’s apartment. Blake opened the door and motioned Jason inside. Blake had come straight from the team’s afternoon weight training session and was wearing a pair of skin tight compression shorts with a workout shirt, both visibly wet from sweat. Blake shut the door behind Jason then walked past him and sat down on the couch. “You ready to continue your training bitch?” asked Blake as he reached down and cupped his large bulge in his hand, giving it a shake.

Jason swallowed before squeaking out, “Yes Sir.”

“Good, strip and get between my legs,” ordered Blake as he manspread his legs out on the couch.

“Yes Sir,” said Jason, a little more composed and confident. He quickly stripped, dropping his clothes haphazardly on the floor then rushed to kneel between Blake’s legs. His eyes immediately were drawn to Blake’s package that stretched out the fabric of his shorts. Blake was not hard yet, but it still made a large bulge. Jason’s cock on the other hand was rock hard.

Jason didn’t see the slap coming, it stung and caused his head to jerk, but it wasn’t hard enough that it would leave a mark.

“Boy, look at the mess you left on my floor,” said Blake as he grabbed Jason’s chin and turned the freshman’s head to wear his clothes were laying in the entry way, “now go over there and neatly fold your clothes and put them in a neat stack on top of your shoes.”

“Yes Sir,” said Jason. He quickly scrambled over to his clothes and did as he was instructed.

“Now get back between my legs on your knees,” commanded Blake. Once Jason was in position, Blake picked up the fully loaded bong off the table. “Time to get you good and stoned,” he chuckled. Blake had Jason take two hits off the bong for every one he took. He also shotgunned his hits into the freshman. Once Jason was baked out of his mind, Blake pulled him up onto his lap.

Jason’s bare cock pressed against the thin fabric that covered Blake’s cock and balls. A shiver ran up his spine as he felt Blake rest his large hand on his naked ass cheeks.

“I’m going to give you ten swats now for making a mess with your clothes earlier. I want you to count them out and after each one say, ‘Thank you Sir, I’m sorry Sir’. Nod if you understand?” asked Blake as he gently ran his hand over Jason’s clenched ass.

Jason’s cock, which had started to soften as he tidied up his cloths, returned to its full five inch hardness as he lay there across Blake’s lap as he anticipated the upcoming spanking. He swallowed hard again and then nodded.

Blake delivered nine sharp slaps to Jason’s tiny pale white ass checks, alternating between the left and right cheek, leaving enough time between each one for Jason to count out the number and say his thank yous and sorrys. Jason felt each spank on his ass and also through the plug pressing against his prostate. For the tenth spank, Blake put more strength into it and gave Jason a hard one that slide across both cheeks. Jason cried out as he pressed his groin down hard and arched his back up raising his shoulders. He quickly remembered to call out, “Ten, Thank you Sir; I’m sorry Sir.”

Blake pulled Jason up to give him a hug, “You were a good boy Jason. You like being dominated don’t you, I can tell, that little dick of yours is hard and leaking all over my lap.”

Jason nodded, acknowledging the truth, “Yes Master, I do.”

“Good, now you get to worship your Master’s body,” he said as he pushed Jason back down between his legs. He quickly stripped of his sweat soaked shirt and put his left arm behind his head, exposing his sweaty smooth pit. With his right hand he grabbed the back of Jason’s head. “Get up here and lick my pit Boy,” he ordered as he guided Jason’s head into his sweaty arm pit.

“Yeah, taste me bitch,” growled Blake as Jason went to work licking and sucking his arm pit. After a couple minutes he switched his arms out and had Jason worship his other pit. Jason was moaning and whimpering as he feasted on Blake’s sweaty pits. Blake gently guided Jason’s head across his torso and to his nipples, letting Jason lick and suck up all the sweat on his chest. Blake reached down and slid off his shorts. He positioned Jason on the couch, kneeling next to his lap.

“Okay boy, suck that cock. I want you to unleash that cock crazed slut I know is in there, show me how much you want, no need, to please a real man’s cock,” commanded Blake.

“Yes Sir,” breathed Jason then leaned over and started sucking Blake’s thick nine and half inch cock. He couldn’t get much more than the head and a couple inches into his mouth at first but did his best to take as much as he could while also working his tongue around on the head between the up and down stokes.

Blake gently rested one hand on top of the teen’s head and ran his other hand down the boy’s sweaty back. He eventually reached the butt plug that was in the freshman’s virgin ass. He gave it a few gentle tugs before pulling it out. Jason came off Blake’s cock and gave a gasp as the wide plug stretched his tight hole as it came out with a plop. Blake reached over to the end table and grabbed the bottle of lube. “I didn’t tell you to stop bitch,” he said to Jason. The boy went back to trying to work more of Blake’s thick cock down his throat. Blake pumped some lube onto the butt plug then set the lube down and slide the plug back into the slim twink’s ass.

Jason gave let out a moan as the plug slide back into his ass, which had felt empty without the plug in it. His eyes were watering and his jaw hurt as he tried to deep throat Blake’s thick cock. Despite the discomfort, he was rock hard. All the years of feeling guilty about and having to repress his desires were being washed away as he sucked on Blake’s cock. He knew he would do whatever Blake wanted, he felt the need to please the upperclassman.

Blake shoved the plug in hard then left it there. The boy’s ass was still tight enough that it held it firmly in place. The jock smiled as he thought about how soon a plug that small would not stay in the boy’s ass after he was done breaking him in. Without saying anything, he pushed himself up off the couch, toppling Jason backwards as the boy tried to keep Blake’s cock in his mouth.

“Bedroom, now,” ordered Blake. He then turned and walked out of the room towards the bedroom. Jason jumped up off the floor and quickly followed Blake to his bedroom, admiring the man’s toned swimmer’s body.

On the nightstand next to the bed were several dildos and a plug that was slightly larger than the one Jason had worn to Blake’s apartment. Blake had Jason get on the bed on all fours with his ass near the edge. For the next hour Blake loosened up Jason’s virgin hole and then slide the larger plug into place. He then had Jason worship his cock again and shot his load down the freshman’s throat. Once Blake had cum he sent Jason home with the larger plug and instructions to be back at his apartment on Wednesday afternoon. Also he let Jason know that he was now no longer allowed to cum unless given permission by his Master.

On Tuesday, Blake had Aiden over to share a bump of coke and breed the sophomore cum dump. After he fucked his load into the boy, the two lay cuddling on Blake’s bed. “How’s it going with the choir boy?” asked Aiden.

“He’s taking to it like a duck to water. He’s going to be begging to take my poz load sooner that I thought. I’m hoping to have to him converted before Halloween so I can introduce him to Daddy Mark and the rest of his family at the annual family reunion,” answered Blake.

Aiden tensed up. Blake felt the boy’s reaction and could see the uncertainty on his face. He gently stroked the boy’s cheek, “Don’t worry Aide, even though this will by your first time at the reunion, you will still get plenty of attention as one of the new boys attending for the first time. Besides you’ve already had the pleasure of meeting Daddy Mark and most of the family at Folsom, which I had to miss because of swim meet.”

“Thank you Master,” replied Aiden.

[Rillion]

Happy Thanksgiving everyone. I hope that there will not be as long a break between 5-6 as there was for 4-5. 

[bootedrbrboi4poz]

It was worth the wait. I'm desperate for the next chapter.

[J-raw]

So glad you're continuing this hot story. I love how twisted it is and your writing. I wish I could have been someone's college 'project.'