Art's New Life

Art goes on a date with Jake that ends well for both of them.

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  • 22 Min Read

Arthur laid on his bed for a while taking in the cool breeze from the near window. Thinking over the events of this morning, he kept having to fight down the creeping thought that they were moving too fast. He didn't realize it then but Jake was along the same line as he went about his day.

"u 2 married yet?" Ellie texted, the notification rousing Art from his train of thought.

"Yur such a bitch."

"Endearingly?" She asked.

"Of course." Art said. "Wanna get coffee when you're free?"

Ellie got off work about 2pm and met Arthur at a little coffee shop downtown. They found a quiet corner and sipped their lattes. Ellie seemed like her normal self but Art was fidgety and she could tell.

"What's the matter?" She asked.

"Nothing."

"Art, com'on."

"I've just got that butterfly thing in my stomach."

"I'd think so." She said taking another sip. "Especially after sneaking out of my house at the crack of 8am."

"So you saw..." Art said with a tinge of blush coming to his cheeks. "Nothing happened!"

"That's you're business. I just saw you as I was getting ready for work. Also, you have about a half dozen hickies."

"Well. We are doing pretty good together."

"I'm happy to hear it." Ellie said with a knowing grin. "I would ordinarily want to know all the details but in this case, you can leave me out of it."

Art gave a little laugh then contemplated his coffee. "What was it like, when he came to you after I left the other night?"

"He started by just asking if we had a good time." Ellie started. "That was already odd to take such an interest in my social life. Usually he doesn't care too much."

Art listened intently. "He seemed kinda off, a little jumpy. Like you right now."

"Hey!" Art imposed.

"Let me finish!" She said batting at his hand. "It was after a little chit-chat that he grew a pair and just said it outright. I wasn't exactly shocked but it was still a surprise. He said that seeing you, being open about it as you are, made him think he could do it."

"That's... So sweet." Art said imagining the hulking man making his brave confession to his little demon- sister, he meant.

"It was!" She said. "I actually had to dry my eyes. Then again, I cry at Pixar movies."

"So as sweet and loving as that it was, how did he end up being my date?"

"Jake and I talked about it more the next morning and he made another confession."

"Well??"

"I asked him if he was seeing anyone and he said no. I asked about crushes and your name might have been brought up."

"I never paid attention to him that way before I met him at the gazebo." Art said. "Now I think I must have been blind."

"So I texted you and set you up for my own amusement." She said downing the last of her coffee.

"I'm glad you did. I'm just scared of getting too deep too quickly."

"Have you caught feelings?" She asked with sarcasm and genuine sympathy.

"Maybe."

"He has too." She said bluntly. "It's only been like, three days too."

"How do you know?" Art questioned, letting his drink grow cold.

"He hasn't told me but it's like something is different about him. There's a light on that wasn't there before."

Arthur's heart was melting at this. The two finished their coffee and parted. Ellie had a date of her own that evening and Jacob had texted that he was gonna be out late. That left Arthur all on his own for the rest of the day. It was nearing the end of the week and a Saturday off was approaching in his calendar. Having confirmed with Jake, Art was gonna spend the day with him.

Such plans resulted in that Thursday and Friday dragging on and on. Saturday might never come at the rate Art's job was going. Mountains of paper were all waiting for him to scan so they could get on to other business. He was distracted by his love life which didn't help the speed of his accomplishments. Jake would take periodically throughout the days checking in, discussing the weather like true Midwesterners, an making plans. Mini golf might have been on there bill of fare, as was a hike or bike ride. When one has a whole day to spare, it's hard to tell what to do. Just sitting and talking would have been plenty of entertainment for Arthur. Jake was learning what buttons to press to get the best reaction out of his boy and Art was eating it up.

Jake made one thing plain though. They didn't do anything that Arthur wasn't comfortable with. They both recognized that they were running fast and knew the perils that spelt in most relationships. Neither wanted a hookup from this interaction and to get the most out of it, they had to tread somewhat carefully. Everyone is on a different wavelength but these two seemed pretty well tuned into each other.

Saturday morning had rolled around and Arthur was eager to get moving. He was dressed and ready to go when Jake pulled his car up to the curb.

"Good morning, Arty." Jake called out from the open window as Arthur approached.

"Good morning. Where are we off to?"

"Just a little place I know?" Jake said beaming. "Eat yet?"

"No. I kind of forgot to."

"Good. I've packed a picnic for us."

They sped off down the road in Jake's sporty little car. Art couldn't help but notice how Jake seemed to fold himself into the driver's seat yet he handled the car beautifully. He also noticed how well Jake dressed. Previously, Jacob had only worn joggers and a tank-top or hoodie. Now he had stuffed his tree trunk legs into some bootcut jeans and had a nice red flannel buttoned up half way just to show off his hairy chest and his sleeves rolled up over his forearms. The drive was a nice one along a scenic route. A river on one side, rolling hills and some granite formations on the other. Eventually they came up to a grassy spot at the end of a little private drive.

"This is my uncle's property." Jake said, extending his legs from the car and climbing out. "We won't be disturbed up here."

"It's beautiful." Arthur said getting out.

Jake had gone to the trunk of the car and removed a blanket, the picnic basket, and a cooler. Carrying everything, Arthur offered to help but Jake just marched up the hill like his hands empty. Art followed.

"Do you come up here often?"

"Only when I want to relax." Jake said picking out a nice flat spot. He set the stuff out and the two spread out the blanket. Arthur looked up at Jacob in amazement. His was even taller in his cowboy boots and as dashing as could be. The flannel was tight in all the right places and showed off his massive biceps and wide back. Jake resembled a cobra when he flexed his lats and traps.

"You've been making it pretty easy for me to fall for you." Art said over his early lunch.

"Have I?" Jake said, mouth half stuffed.

"You know you have." They both gave a devilish smile.

Jake and Art sat in the shade for an hour or so just talking. With every passing minute, they grew closer and closer.

As Arthur reclined himself onto Jake, his head in his lap, he looked up at the man who in turn stroked Art's curls and looked into the longing eyes. Jacob gave a little giggle at a thought.

"What?" Art asked.

"I only thought, How is this boy a virgin still?" Jake chuckled.

"Hey!" Art complained jokingly.

"I only mean that you're so adorable, I'm lucky no one else got to you before I did."

"It didn't sound like you had too storied of a past." Art said poking at Jake's belly.

"True." He said, gripping the curls sliding through his hand. "But now there's you." Jake leaned down and kissed Arthur's forehead. 

"You definitely know what I like." Art said.

"A domineering man with self esteem issues?"

"Don't be mean!" Art teased. "I'd like to help with both of those."

"I'll let you." Jake said, craning down for another kiss. This one meeting on the lips.

They stayed in that position for a while before it was time to get going. A movie was gonna round out the rest of their time together once they got back to the basement hideaway. After putting the picnic stuff away in the trunk, Jake gently pushed Art against the car and dove in for kiss. Their tongues entwined and seemed to wrestle for dominance, of course Jacob won. His strong arms pinned Arthur against the car while Art's hands felt up the warm, muscular mass in front of him. Once his hand made it to the beltline, he felt the bulge snaking down to the left. It was throbbing, seemingly in time with Jake's kisses.

Jake reached a hand up and caught Art just under the chin. "Come on, we better get going before we get to carried away."

Art slapped Jake's ass for a response and slowly made his way over to the passenger side. Jake followed.

"I might get you for that one." He said with a sly grin. He pushed Art against the car again with one hand on the back of his neck. Art was flattened against it as Jacob took a swing at his ass. The smack was a hard one and Arthur gave a little gasp. He didn't expect to like it so much.

"Just reminding you who's boss." Jacob growled, going in for one more kiss before opening the door for Art. "Next time, I might just have to paddle you."

Art smiled and got in the car more aroused than ever. His cock leaking precum as was Jake's. The drive back was quiet. The two watched the scenery fly by till they were back at Jacob's and absconding to the basement, unseen by the rest of the household.

"Wanna get steamed up?" Jake asked, opening the door of the sauna. "It won't take too long to get warm."

"Yes Please!" Art replied. He went into the bathroom and undid his belt. In the mirror, he saw Jake standing outside the doorway looking in, checking out the goods. "See something you like?"

"I didn't mean to stare." Jake said, obverting his gaze.

"You aren't bothering me."

Jake watched as the shirt was dropped and the pants slid down revealing Art's soft white trunk style underwear. He would have been drooling at the corners of his mouth if he had less self control. Arthur's perky little ass filled out his underwear nicely. The definition of his back seemed to draw the eye down right to it. Art turned and stepped out and Jake took his place.

Following Art's lead, Jake stripped down to his underwear, some dark, long boxer briefs with a pouch that cradled his massive tool. Though only at a semi, the waistband appeared to be struggling against the weight as it was constantly pulled down in the front. Jake shut the door to use the toilet and Arthur meandered in the bedroom for a moment. Sticking out of a half opened dresser drawer were the straps of a bright blue jock with yellow piping around the edges. Arthur pulled it out and looked it over. The size was extra large and had a stretched out pouch.

"You like it?" Jake asked, having snuck up to the bedroom doorway.

"It's hot." Art said tossing it at Jake.

"Go get in the sauna. I'll be right there."

A moment later Jake joined him and as Art had hoped, had changed into the jockstrap.

"Holy fuck." Art exclaimed, eyes bulging out of his head. "That thing is about to blow!"

"It's pretty tight." Said Jake, adjusting the payload. "Glad you like it though."

Jake approached and heaved his foot on the bench next to Art giving a nice wide view of the goods. Arthur slowly crept his hands up the leg to the bulge and began to fondle it.

"Maybe you'll get too warm in that." Jake said.

Art took the hint and stood up, embracing Jacob's mass and slid the waistband down over his ass. His cock popped up as the band went down revealing his mast standing at attention. Jake took the spot on the bench and viewed the sight before him.

"You sure you're okay with this." He asked Art. "We could even make a safe word if you want it."

"I'll be fine. You're just so unbelievably hot."

"Speaking of hot." Jake said, dashing some water on the stones. "Come take a seat."

He spread his legs wide taking up the whole bench. Arthur sat down on his lap feeling the bulge press between his ass cheeks like a hot rod of iron. The thin fabric of the jock did nothing to conceal the throbbing heat Jake exuded. Jake's arms wrapped around his prey like a python and held Art tight. It was so warm and comfortable, they could have stayed like that all night. 

Jake began to nibble at Arthur's ear lobe, whispering occasionally the things he wanted to do to him.

"When you want it." He started, "I'll pound you so hard you won't walk the next week."

With every word, he ground his shaft into Art's ass, rubbing the sweat and the precum now soaking through the jock, right up against the hole.

"I want you in me." Art whispered through his labored breathing. He tried to touch his cock but Jake grabbed his arms and restrained him.

"Not yet." He said teasing. "If you want it, I'll help you get ready. I'll be gentle for your first time."

"What about the second time?" Art said laughing a little.

"No mercy then." Jake laughed. He began to stand and instead of letting his new toy slide from his lap, he picked up Art and carried him to the bathroom. It was a new world to Art and Jake for that matter too but they were gonna learn it together. Jake helped Arthur get squeaky clean before they had a quick shower to rinse off the sauna sweat. Jake left Art in the bathroom and went into the bedroom.

"Oh my god." Arthur thought to himself. "It's gonna happen." He was getting nervous. His first time was gonna be with a monster of a cock but at least it was attached to someone like Jake. There was a trust between them, still young mind you, but growing stronger and that meant more to Art than anything else. He stepped out of the shower and dried off.

Upon entering the bedroom, Jake was no where to be seen but he had been busy. A couple of candles were the only light in the room, there was lube on the nightstand, and the covers were stripped from the bed. Jake had been clearly looking forward to this and Arthur was nervous. Jake came back into the room from the closet with a couple towels and laid them on the nightstand. He had lost the jock.

Before Art's eye was Jake in all his glory. The python between his legs had grown to nearly it's full potential. "I've gotta be honest with you, I couldn't find a condom at the gas station that fit."

"We'll manage." Art said, quaking at the knees.

"I'll pull out if you want."

"You're the boss here." Art said slowly approaching.

"Get on your knees then." He ordered with a smile.

Arthur did as he was told and came face to face with his new best friend. The foreskin had pulled back revealing the shinning head, dripping with precum. He leaned in and began to make love to it. He tonged ever bit of it seemingly trying to lap up ever drop of pre. Jake enclosed his hands behind Art's head and began to pull, not very hard but noticeably.

"Ah fuck dude." Jake said in a hushed tone. "Fucking suck on that bitch."

He was enjoying himself immensely. Art was having a fun time of it too. He felt like this was where he belonged and was loving every second, every inch. Slowly the head disappeared into Art's willing mouth. Just the tip was filling the whole cavity but it kept on coming. Art sputtered a bit as the shaft reached is throat and shoved his uvula out of the way.

"Come on, boy." Jake said. "You're doing so good."

It was then he let Arthur up for a breath but not letting his cock leave entirely. Art breathed around the head then pressed back down. This was repeated over and over till a change in position was necessary.

"Get up. Lay down on the bed. Hang your head off."

Jake had ordered and Art complied as quick as possible. Looking at the waiting beast upside down, he began to wonder how far he could get down the shaft. Surely no one had ever gone to the base but if he could get around the widest part, he'd be proud of himself. Jake moved forward and began to tease his play-thing. The massive tool draped across Art's face was just comical. It was so big, everything was made smaller in comparison. It poked at his lips and Art began to lick at it.

Jake teased him. Every time it seemed like it was going to go inside, he pulled away and slapped Art's cheeks with his heavy member. Soon though, enough was enough and he entered the waiting hole. He kept pushing and pushing until Art pushed against his meaty thighs. jake pulled out and let Art breathe before diving back in. Each thrust brought the head deeper and deeper. Arthur would sputter a little but recover and keep going. It went on for half an hour still. Jake was in most exquisite euphoria as was Arthur. Jake would occasionally reach down and toy with Art's cock or tweak his nipples a little. Every time he did it, he could thrust a little deeper into the tight throat.

Art had sucked down about 8 of the 12 or 12.5 inches when he finally couldn't go deeper. It was the most anyone in Jake's limited experience had done and he was proud of his boy.

"Get up." He said as he pulled out slowly, a string of spit and mucus dangling from his cock to Art's mouth. "Lay flat. Now prop your ass up and arch your back."

Art did as he was told and braced himself.

"Mmm. Good boy." Jake said, popping the cap off the lube. "I'm gonna open you up a little."

Jake applied some lube to his fingers and gently pressed his middle finger in first. It was tight and Art gave a quiet moan as it slid in.

"Fuck. You're so fucking tight." Jake said withdrawing. "I'm gonna fix that soon. Here's another."

He pushed in again, two fingers and stroked them in and out till a third could be pushed in. Art was beginning to moan louder.

"I got an idea." Jake said leaving a moment. "Here, bite on this and shut up."

The harsh words turned Art on as the blue jockstrap was stuffed entirely into his mouth. 

"That should keep you quiet." Jake said returning his fingers to the tight pink hole.

It was different this time, a little easier. That is, till his pinky start to wriggle in. Four of Jake's meaty fingers were pushed into the hole helping expand it to receive the main course.

Art bit tight on the jockstrap till his hole was released from the intruder. He felt something else now at his hole. Jake's scruffy chin and tongue were digging in with all the strength he could muster. His strong hands had gripped Art's side and weren't letting go. His strong, massive tongue kept at it till Art's ass was truly soaked and his cock was leaking like a faucet.

The cold air was a shock to him when Jake's face left. Something hot soon replaced it. Art's hole was being pushed in on by a large, blunt object. Jake's cock pushed and pushed till at last, the head gained entry. Art shook a little.

"Just breath." Jake said adjusting his death grip on Art's waist. "If you want me to stop, just spit the jock out and say it."

Art nodded understanding and braced himself. Jake began to pull the twink onto his ridged cock, one slow inch and a time.

"Try to relax." Jake said in a calming tone. "Let go. Open up for it."

Arthur did his best and Jake sank deeper. After what felt like ages, Art could feel a bush beginning to press against his ass and Jake's slight belly rest on top of him. he was seeing stars but was determined.

"Congrats bud." Jake said grabbing the back of Arts neck and lifting a little. "You just lost your cherry."

On that note, Jake began to pull out and drizzled a little more lube on his cock. He pushed again and met less resistance bottoming out. Art was drooling through the jockstrap now as the anal assault continued.

"Fuck yeah. Take that cock." Jake growled. "You're a pro already."

He began to loose the gentleness that he started with. Jake would pull all the way out then drive it back home over and over just to watch Arthur squirm. Using his powerful arms, he twisted Art around to be on his back all without leaving his ass. He took an ankle in either hand and pushed them forward, folding the flexible little swimmer in half.

"You love that dick don't you?" Jake said, staring into Art's eyes. "You look so fucking cute and pathetic right now. How's that jock taste,  boy? What? Can't hear you."

He went on a little faster and a little harder. Arthur was beginning to melt under the treatment he was getting.

"Are you Daddy's boy?" Jake said gripping his chin. He gave a playful little slap. "Fuck yeah you are."

The fucking continued for almost 45 minutes in multiple positions. In each one, Art was as helpless as the last. He was experiencing a new sensation slowly creeping up though, like someone punching a button over and over till he was at the brink. A massive cum shot burst from his little cock covering his abs. Jake saw this and growled in approval. He stopped a moment and pulled out, scooped up what he could with his fingers and rammed them into Art's widened hole.

"First person to breed you was yourself." He chuckled a little and pushed his cock back in. He pulled out the jock from Art's mouth and replaced it with his cum covered fingers.

"That's right, boy." He said with a sadistic smile. "Taste yourself."

He began hammering away, harder than ever. Art's prostate was getting rammed every half-second and it was driving him wild. Soon, he felt another explosion from inside but nothing but a small amount of watery cum dribbled out. Jake still didn't let up. How he could keep up the stamina was a mystery to Arthur who was already reduced to a putty in his Daddy's hand.

Eventually all good things must come to an end and Jake began to slow down. What he lacked in speed was made up for in force and he made a resounding smacking noise with each thrust. Arthur was thrust forward several inches till he came close to the edge of the bed. At this point, Jake grabbed him and dragged him back. A final pile drive left Arthur under Jake's entire weight as he suddenly stopped. Art felt the massive member throb in his lower abdomen, pumping his cavities full of hot cum.

Jake put one arm around Art's neck and propped them up with the other so that Jake was kneeling and Art was suspended by the neck and shoulders. The massive cock was still pumping it's load and Jake would occasionally thrust in.

"Look at yourself." He ordered, pointing Arthur's head at the mirror across from the bed. "You're such a cock whore."

Art looked over and saw a pitiable sight. He was well run through. He felt his lower stomach and when pressed, he could feel the cock inside him. As one last show, Jake moved towards the edge of the bed and began to stand up. Arthur was starting to freak out but was held in place by the meaty arms wrapped around him. He was positioned in front of the mirror and Jake thrusted himself forward making a visible bulge in Art's tummy.

"Jesus fuck." Art said breathlessly.

"You won't be moving for a while." Jake said, turning back to the bed.

As a demonstration of his strength, Jake lifted Art at the shoulders and removed him from his still nearly rigid cock. Art was thrown down on the bed and maneuvered so that his head was once again hanging. Truth be told, Art didn't have the ability to even lift it.

"I'm gonna cum one more time." Jake said lining up with the waiting hold. "Swallow every drop."

Jake pumped his cock using the cum from Art's hole as lube and was soon at the brink once again. He started to moan and aimed his nozzle. Spurt after spurt shot into Art's mouth till it was almost full. Art swallowed what he could but he felt truly glazed. Jake wiped his cock off on Arthur's tongue and slid him over, sitting down next to him.

Arthur was a mess and Jake started to clean him up. Some baby wipes were produced from a drawer and the hulking man cleaned his toy with a gentleness you wouldn't expect from the man responsible in the first place. Upon rolling Arthur over and inspecting his ass, Jake was happy to see his handywork. A gaping hole stood when before a tight, pink, virgin had been before. Cum oozed out and was swiped up with a finger. Jake once again made Art lick it off and went about getting him ready to sleep.

"You did so well." Jake said with pride.

"I'd be very surprised if no one heard us." Arthur said, propping himself up a little.

"When I moved down here, I put in some sound-proofing before finishing the rooms off."

"Then why the jock?" Art asked.

"Because I like seeing a hot guy choke on my underwear." Jake said, punctuating his statement by slapping Arthur's ass.

Art rolled over and pulled Jake in with him. There they stayed till morning, Art using Jake's mass like a weighted blanket.

Once he woke up early the next day, Arthur tried to move but couldn't without pain. His joints hurt, his ass was raw, everything seemed well used. He could hear a banging noise coming from the next room and found Jacob working out. He had earbuds in so didn't notice his audience for a few minutes.

"Oh hey there." He said pulling a bud out. "How ya feeling this morning?"

"I think you know." Arthur said in jest.

"If you can walk the morning after, clearly I need some more practice." Jacob joked. "Come here. Let's see if I can put my schooling to good use. The weight bench will have to do."

Jake was studying to be a chiropractor like his father and was always up for the practice. He was either going to help Art or break him completely. Either way, Arthur was gonna be around for a while. Jake had been giving deep tissue massages to his fellow footballers and now he was going to do the same to Arthur only, more delicately. Art was a lot smaller than what he was used to.

Art's arms and legs were worked first, then his torso. One muscle group at a time, Art was massaged. It was indescribable the kind of intertwining pain and pleasure he was feeling. As a finale, Jake laid down on top of Arthur who was face down. Jake's weight shifted in just the right way to make a popping noise. Arthur moaned and went nearly limp.

"That's it." Jake said. "Now you're gonna feel like a million bucks in a few hours."

"I'll take your word for it." Arthur said, attempting to stand but failing miserably.

"I'll take you to the bathroom. Take a hot bath and relax."

Before Art could respond, Jake picked him up and carried him bridal style over the threshold of the bathroom. He was set down on his feet and helped over the wall of the tub.

Arthur had never been so at peace, especially after such an experience as last night. Jacob had proven himself to be sweet and kind as well as a full on dom. He was definitely a top that knew what he wanted and Arthur was realizing that he was falling very comfortably into a submissive role. After 20 minutes, the bathroom door opened and Jake came in completely nude. Judging by his color and the sweat, Art could tell the sauna had been running.

"Scoot up." Jake said taking a step over the tub wall.

He placed himself so that Art had to sit between his legs and on his cock if they were to both be in the water.

"This has been so much fun." Art said leaning back against the mass behind him. "If we do this more often, it might kill me though."

"You just need to get used to it." Jake said pulling Arthur in close. His cock was sandwiched in his tight ass crack.

"Maybe." Art said thoughtfully. "You were pretty rough though."

"Babe, that was easy." Jake retorted. "I have some kinks I could work out that would scare you off."

"I haven't runaway in terror yet. What's your worst kink?"

"I wouldn't say worst." He said thinking. "I'm just pretty dominant and there's a lot that can go with that if you were willing."

"I'd hear you out."

"It's not a deal breaker either, I just wanted to throw that out there." Jake said.

"What do you want most?" Art asked settling back a little further.

"I'd want to make you mine." Jacob said "I want you to have a physical reminder of who you belong to."

"I think my throbbing ass has already accomplished that."

"Somewhat. I like to have control though." Jake said. "It takes a lot of trust though for something like that so I want to wait, until you're sure."

"I understand." Arthur said sympathetically.

A mutual respect and trust was already there and growing ever moment they were together. Jake's hesitance drove a burning curiosity in Arthur to know what was in the works.

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