Chapter 07.1
Jake rolled over, pushed the covers back, and sat up on the edge of his bed. He looked down at his morning wood which felt a bit more stiff and excited than normal. He then looked behind him at Ryan, who was still asleep and just as naked as Jake.
Jake took a moment to recall the previous night's glory. He and Ryan had enjoyed a marvelous evening of sex and debauchery. They had sucked each other. They had fucked each other. They had tasted each other's bodies and sexual fluids. And when they were done, they had embraced in a passionate kiss before falling asleep together completely nude.
For a brief moment, Jake felt the urge to walk to the other side of the bed and jerk himself off onto his friend. That desire quickly passed and he decided to let his good friend sleep and continue recovering from their magical sex marathon.
Standing up from the bed, Jake made his way over to his dresser. He opened the top drawer and pulled out a fresh pair of underwear: blue bikini panties. Although his erection was starting to subside, he still had to maneuver his manhood so that everything was nice and snug within the confines of his underwear. He then put on a white tee shirt and headed for the kitchen, hoping to find some coffee.
As Jake sauntered into the kitchen, he found his coach and his mother seated at the table eating breakfast.
"Morning, guys!"
"Good morning, cream puff!" Bruce replied with a wave.
"Morning, sweetie." Kathy said, looking over and smiling at her son. "Oh goodness. Did you really not have any shorts or pants you could put on, honey? I can see your whole... package... just bulging out of your underpants."
"Come on, mom. You were prancing around in your panties the other night. I'm not allowed to prance around in mine?"
"He makes a good point, Kathy." Bruce chimed in. "Let the boy flaunt his youth. He has a nice body and he fills those panties out quite well."
"Oh fine. You guys win." Kathy agreed. "I suppose I shouldn't be a hypocrite."
Jake reached for a coffee cup and poured himself some fresh coffee, adding a little sugar and cream.
"So honey..." Kathy started. "... I noticed Ryan's car here last night. And I noticed that it's still here this morning. Does that mean what I think it means?"
"Just means he spent the night." Jake answered with a sly grin.
"Don't play dumb with me, young man. You know what I'm asking." Kathy added with a giggle. "Did you guys talk? Did you fool around together? You don't have any pants on this morning, so I'm assuming you must have had a good visit."
Jake blushed as he took a sip of coffee. He could barely contain his excitement.
"It was a very pleasant evening." Jake answered.
"Quit beating around the bush and answer your mother." Bruce told him with a chuckle. "Don't keep us in suspense! Did anything happen between you and your friend?"
"Yes, Ryan and I took our friendship to a new level yesterday." Jake replied. "We spent the entire night exploring each other's body. Every inch. Every nook and cranny. It was passionate and beautiful. We were both a sticky, sweaty mess when we fell asleep together."
"Oh yay! Honey, that's so wonderful." Kathy exclaimed. "I know how badly you wanted to have sex with him, so I'm happy it became a reality."
"Thanks, mom!"
"Does that mean Ryan is gay like you?" She asked.
"Not exactly." Jake answered, taking another sip of coffee. "He still likes girls he said. But he watched my porn scene and really wanted to experience having sex with another guy, so we basically took turns fucking each other all night long and he really loved it."
"Sounds like Ryan is bisexual like me. I'm proud of you, Jake." Bruce said. "You didn't give up on your dreams and you got your wish. I'm a little jealous I wasn't there to watch you horny boys fucking each other up the ass."
"It was really hot, coach."
"Thankfully I got to plow some quality ass myself last night." Bruce added, smiling at Jake's mother. "Sounds like everyone in the house went to bed happy last night."
Jake took another sip of his coffee.
"So are you two an item now?" Kathy asked. "Are you and Ryan going to start dating now that you're having sex?"
"I don't know if he wants to be my boyfriend." Jake answered. "But we're definitely going to be having more sex together."
"Maybe I should take you boys to my cabin this weekend." Bruce suggested. "I could invite Kevin and Cliff... we could make it a guy's weekend."
"That sounds awesome, coach." Jake said, suddenly imagining himself surrounded by four naked, horny men. "I guess I should go back and check on Ryan. I'll mention the cabin and see if he would be interested."
"Have fun playing with your friend, sweetie." Kathy told her son.
"Here's to a lot more gay sex for you, Jake!" Bruce added, raising his coffee cup.
Jake raised his cup in agreement, swallowing down the final gulp of his coffee. He set the cup down and began to head back to his room, feeling a renewed sense of arousal stirring in his panties.
As Jake approached his bedroom, he noticed that the light was on. He quietly made it to the doorway and pushed the door open. He saw Ryan sitting up in bed, flipping through his gay porn magazine with one hand. Ryan's other hand was under the sheets, which Jake noticed were prominently tented.
"Enjoying yourself?" Jake asked.
"I think that's pretty obvious." Ryan said with a laugh, referring to his pole poking up under the sheets. "Sorry I helped myself to your magazine without asking. I woke up hornier than usual and couldn't help myself."
"No problem at all. Gay porn is something everyone can enjoy." Jake told his friend. "I'm happy to see that you really like it."
Ryan turned the page as Jake tugged the sheets away, revealing Ryan's erect penis and the hand that was stroking it.
"There's that gorgeous cock." Jake said. "Mind if I help you with that?"
"Be my guest."
Ryan let go of his dick as Jake sat on the edge of the bed next to his friend. Jake licked the palm of his hand and wrapped it around Ryan's shaft, gently starting to stroke the penis himself. He noticed that the page Ryan was on had a close up picture of a smooth, bare ass stuffed to the brim with a huge cock.
"That's one of my favorite pictures in the entire magazine." Jake said.
"I can see why." Ryan agreed. "Look at how stretched out that guy's butthole is. He definitely has had a lot of dicks in there if he can fit that monster. And then the size of the balls on the guy fucking him. Wow. Look at that sack!"
"I know." Jake added, still stroking Ryan's cock. "You know that lucky guy got a huge load up his ass."
Ryan turned the page and took in the new set of pictures. There was a picture of an erect penis sticking out of an unzipped pair of slacks. There was a picture of a naked boy at a computer, masturbating while what looked like a father figure was standing behind him and watching, also masturbating. On the other side of the magazine was a full-page picture of three guys on the floor in a circle, each of them sucking the dick of the guy in front of them.
"This is so hot." Ryan admitted. "I think I'm more turned on by looking at cock and naked guys than I realized."
Jake briefly took his hand from Ryan's lap, spitting into his palm and then resuming the handjob. Jake smiled as he felt Ryan's penis throbbing in his hand.
"Maybe I'll see you in one of these magazines one day." Ryan said. "Now that you've started doing porn."
"I'm not so sure about that." Jake replied with a laugh. "That'd be pretty cool though. I never thought I'd be in a gay video, but now that's on the internet for the whole world to see."
Jake worked his hand up and down Ryan's dick. With his other hand, he began to fondle his friend's testicles. Ryan turned the page once more.
The boys observed the next set of photos. There was a picture of two naked men standing up and making out, their erections crossed and rubbing together, their hands grabbing each other's bare ass. There was a picture of a young, smooth twink on his knees. His face was surrounded by six long, fat, beautiful cocks. And finally there was a picture of a threesome. One man was fucking a tight hole while also being fucked from behind.
"Talk about the best of both worlds!" Ryan commented. "Imagine the sensation of being inside of someone's ass while also experiencing the immense pleasure of having someone else in your ass."
"Sounds wonderful." Jake said, still tugging on his friend's erection. "I also wouldn't mind being that twink that's about to get to suck off six different dudes."
"Yeah that's pretty hot too."
"Speaking of a bunch of dudes having sex." Jake added. "Coach Campbell wants to take us to his cabin this weekend. He mentioned inviting a couple of other guys too. I've met them. They're nice."
"Really?"
"Yep. He was eating breakfast with my mom when I was in the kitchen earlier." Jake told him. "They noticed you had spent the night and they asked if we ended up having sex. I told them that we did and they were both really excited and happy for us."
"That's so cool how supportive your mom is." Ryan said.
Ryan set the magazine down to focus on the handjob he was receiving. Jake stroked the penis even faster.
"I'm so close, dude." Ryan announced. "You're gonna make me pop."
"I want to taste it." Jake told him. "Shoot it in my mouth."
Jake kept pumping the cock as he lowered his face, opening his mouth and placing his lips over the head. He jerked Ryan's penis even faster, feeling him twitch and begin to ejaculate. Two large globs of sperm shot into Jake's mouth which he promptly swallowed down. That was followed by a small trickle of sticky leftovers which Jake gleefully slurped up and also swallowed.
Jake released the dick and sat back up, smiling at Ryan.
"Yummy!" He said. "So how about coach's offer? Would you want to spend a weekend with me and three other guys?"
Now it was Ryan's turn to smile.
"That does sound really hot. I'll make you a deal." Ryan decided. "I'll agree to a weekend at the cabin if you return the favor and squirt your load in my mouth right now."
"Deal!"
Jake stood up and pulled his panties down slightly, letting his own aroused manhood swing freely. Ryan laid back with his head on the pillow and opened his mouth. Jake started to play with himself as he stepped toward the head of the bed. He pointed his penis at Ryan's mouth as he began to jerk off.
"Just shoot it directly into your mouth, huh?"
"Yes please. You got to swallow mine, now I want to swallow yours."
"You know what this cabin weekend means, right?" Jake asked as he stroked himself. "Five guys. It's going to be an even longer marathon of horny, nasty gay sex than we had last night. And Coach Campbell is probably going to expect you to bend over so that he can fuck you with his big cock."
"I'm aware of that." Ryan said. "Last night I dipped my toes into the waters of gay sex. Might as well try jumping into the deep end."
"If last night was just dipping your toe in, I'm curious what jumping all the way in looks like." Jake told him. "But for now, I'm just going to stay focused on jerking off into your mouth."
"Sounds like a plan!"
Ryan closed his eyes and held his mouth open. Jake kept his dick aimed at his friend's face as he stroked himself. He sped up his stroking as he knew he was close to orgasm.
"Hold still." Jake said. "Here it comes!"
Now it was Jake's penis that twitched as a sizeable squirt of cum jettisoned from his dick and went straight into Ryan's mouth. A second, smaller squirt followed that as Jake slowed down on his stroking. There were some stubborn, sticky droplets that oozed from Jake's urethra, which he carefully wiped off on Ryan's lips, applying the semen with his cock as if it was lipstick.
Ryan closed his mouth, swallowing the salty load, and then licked his lips as he opened his eyes. Jake stepped back and pulled his panties back up.
"That was delicious." Ryan commented. "Thank you for sharing it with me."
"My pleasure. Thanks for letting me give you a handjob!" Jake replied. "And don't forget our deal. Now you have to go to the cabin with me this weekend."
Ryan swung his legs over the side of the bed and got to his feet, his now-soft penis casually dangling from his waist.
"Don't worry. I keep my promises." Ryan assured him. "I guess I should probably get dressed and head home though. I have some chores I need to knock out."
"Before you go..." Jake stammered. "... I'd really like to kiss you again."
"So get over here and kiss me, silly."
They both smiled as Jake stepped forward. They wrapped their arms around each other and pressed their lips together. Jake lowered one hand and grabbed Ryan's ass. Ryan did the same, squeezing Jake's buns through his panties. They both parted their lips and allowed their tongues to wrestle together. After a few moments of making out and grabbing each other's butt, they broke their embrace.
Jake watched as Ryan got dressed and gathered his things. He then walked him to the front door, where they shared another quick kiss and said their goodbyes.
The next couple of days felt like an eternity as Jake waited for the weekend to arrive. It finally had, and they were now just a few miles from the property.
Bruce had offered to give Jake and Ryan a ride and the boys accepted the offer. The coach was driving while the two young friends were in the backseat.
"We should be there any minute." Bruce said. "Are you guys excited?"
"I'm very excited!" Jake exclaimed.
"I'm really excited too, coach." Ryan chimed in. "I've had a boner for almost the entire car ride."
"I wish you would've said something earlier, Ryan." Bruce told him. "If you had, Jake could've sucked your cock for you. But now we're almost to the cabin and we don't have enough time."
"Sorry, coach."
"It'll be fine. But take this as a learning opportunity." Bruce added. "If you don't speak up about your feelings and desires, you may never get the chance to explore them. You didn't speak up about being horny, so you missed out on a blowjob."
"That makes sense." Ryan agreed. "I'll work on being more open and vocal going forward."
"Good boy." Bruce said. "Now Jake... I think Cliff is bringing some video equipment. Probably more than one camera. I think he wants to get some footage and make a video documenting your first experience with a gay orgy. How does that sound?"
"That sounds fucking awesome!"
The coach chuckled at Jake's genuine enthusiasm.
"That's the reaction I was expecting." Bruce told him. "It's another great opportunity to show the entire world how much of a dirty faggot you can be."
"I'll do my best!"
"I know you will." Bruce added. "But there's also going to be plenty of sex going on in general. Ryan, don't take this the wrong way but I'm also looking forward to giving your little shithole quite a pounding this weekend."
"I kind of figured, coach." Ryan said. "I'm looking forward to it."
Jake reached out and took Ryan's hand in his. They gave each other a squeeze in nervous anticipation and excitement. Bruce turned the steering wheel and pulled into the driveway of the cabin. Kevin and Cliff were already there with their own vehicles parked.
"There isn't another house for a few miles." Bruce said. "So don't be shy about being naked outside or anything like that. Perhaps even having sex outside. No one will see you."
Bruce put the car in park and shut off the engine. They all got out and grabbed their respective bags and suitcases and made their way to the front door. They walked into the cabin and greeted Kevin and Cliff.
Jake introduced the two men to Ryan and then noticed an interesting assortment of items on the coffee table: several bottles of lubricant, plugs, beads, vibrators, various sizes of toy dongs, and even a double-ended dildo.
Jake also noticed that his coach was right about Cliff, as there were multiple video cameras plugged in and charging. Jake greeted Kevin and Cliff himself, giving each of them a hug.
"I'm glad you guys could make it." Bruce said. "Let's give these boys a weekend of unforgettable ass fucking!"
"That's the plan!" Kevin added with a laugh.
Jake and Ryan liked the sound of that as well, turning to each other and exchanging a high five.
"So should we all strip down and just start fucking?" Jake jokingly asked.
The other men had a good laugh at Jake's suggestion and Bruce gave him a smack on the bottom.
"There's going to be plenty of cock fucking your queer ass this weekend. I promise you that." Bruce said. "But first... did you bring anything sexy to wear? Maybe you could go change into something more revealing and try to turn us on. Ya know... you can try to earn the penis rather than us just giving it to you."
Jake smiled and blushed at the challenge.
"I can do that. I have a good idea for a sexy outfit I can put on." Jake told them.
"Mind if I join you, Jake?" Cliff asked. "I could get some footage of you changing and ask you some more dirty questions."
"That's fine with me."
Jake grabbed his suitcase and Cliff grabbed one of his cameras. The two of them made their way to one of the bedrooms. Jake put his suitcase on the bed and opened it as Cliff readied the camera.
"You'll know I'm recording when I start to ask you questions." Cliff explained. "Just strip down and change like you normally would while giving answers."
Jake began sifting through his suitcase and pulling out some items. Cliff began to record.
"Look who's back, guys. It's Jake!"
Jake smiled and waved to the camera.
"Hey, sexy boys." He said. "I hope you're ready for some more hot, nasty action."
"He's not kidding." Cliff added. "Jake is here with four other horny men for the weekend. Are you excited about your first gay orgy?"
"Very excited!" Jake exclaimed. "An entire weekend with four cocks to suck and fuck and service? That's a dream come true for a boy like me."
"I'll bet it is." Cliff said as Jake unzipped his jeans and took off his shirt. "And I imagine you've been servicing men often since we last saw you on camera? If you had to guess... how much cock would you say you've sucked since our last video?"
"I feel like that question only has one correct answer." Jake replied, tugging his jeans down and revealing his purple bikini panties with black, lace trim. "How much cock have I sucked? Not nearly enough!"
Cliff chuckled as Jake pulled his jeans the rest of the way off.
"I love that answer." Cliff said, zooming in on Jake's privates. "Still rocking the panties I see."
"Of course! I love wearing panties." Jake explained. "I should have been wearing them my whole life."
Jake turned around to show the camera his bottom as he pulled down his underwear.
"There's that young, gay ass." Cliff commented. "I can't wait to pump a few loads into that thing again."
"Well that makes two of us!"
Jake turned back around, now treating viewers to a good look at his dick and balls. He then proceeded to pick up the items he had taken out of his suitcase.
"What kind of outfit did you pick out?"
"I wanted to try something fun and cute. I've got some thigh-high stockings, a garter belt, and a thong." Jake answered.
"That sounds lovely." Cliff told him. "And Bruce told me you started a gay OnlyFans account. How's that going?"
"I think it's off to a good start." Jake replied, putting on his black garter belt. "I'm almost to 100 subscribers, so that's cool. It's free right now so that guys can check it out risk-free."
Jake began to put on the first stocking, rolling it up his leg.
"That's great that you're building up a subscriber base." Cliff said. "Has anyone contacted you?"
"Oh yeah, several people have commented or sent me messages." Jake answered, putting on his other stocking. "One was a married guy who said he's still in the closet. He said I reminded him of his son, but that his son wasn't gay unfortunately. He suggested I post a video addressing the camera as "daddy" and talking about what a naughty boy I've been and how I need daddy to teach me a lesson."
"That sounds hot."
"I know. I need to make him that video." Jake added, connecting the garter belt to the stockings. "It sounds like he wants to jerk off to it imagining I'm his son and begging for his cock."
Jake picked up the thong, the final piece of his ensemble. He stepped into it and pulled it up, doing his best to fit his package into the small front.
"How do I look?"
"Like a boy who could use some dick." Cliff answered. "Turn around. Let's see that booty again."
Jake did as he was told, showing off his bare ass cheeks to the camera. Those same cheeks concealing the thin strip of material that was safely nestled in his crack.
"Look at that butt." Cliff said. "I have a feeling that you're going to be riding a lot of penis this weekend."
"I certainly hope so!"
"Let's go back to the living room." Cliff suggested. "Let the other guys get a look at you dressed like a dirty, cocksucking whore."
Jake giggled and made his way down the hallway, Cliff following behind with the camera focused on capturing Jake's buns swaying back and forth with each step.
When he made it back to the living room, Jake was pleasantly surprised to see that Ryan had taken off his pants, leaving him in just a white shirt and a jockstrap that left his bottom completely exposed. Bruce and Kevin were running their hands all over Ryan's body, looking him over and checking out his bits.
Bruce looked up and saw Jake sauntering into the living room and seeing how he was dressed.
"And here's the other faggot now!" Bruce exclaimed. "That's a wonderful outfit, Jake."
"Thanks, coach."
"You look hot, dude." Ryan added.
Jake showed his appreciation for the compliments with a curtsy.
"Kevin and I were just having a closer look at your friend." Bruce explained. "I know how much you love asses. Why don't you get on your knees behind your friend show us all how much you appreciate a nice butt?"
"Yes, sir."
Jake knelt down behind Ryan. Cliff made sure to hold the camera where it could capture the impending action. Jake leaned his face close to Ryan's bare ass.
He started with a long, slow, deep inhale of Ryan's anal fragrance.
"What do you think?" Bruce asked. "Does Ryan's butt smell nice?"
"It smells awesome." Jake answered, taking another quick sniff. "I bet it tastes even better."
Jake pushed his face into Ryan's ass crack, wasting no time licking, kissing, and sucking on his fuckhole. It was as if Jake was starving and Ryan's asshole was the best tasting meal he had ever had. Jake pushed the cheeks open so he had even easier access to his friend's anus.
"He just went right for it." Kevin said, watching Jake eating Ryan's ass. "He didn't hesitate to go right for that butthole."
"You act surprised." Bruce quipped. "You've seen what a dirty fag he is firsthand. We all have."
"That's true." Kevin agreed.
Jake continued to vigorously and aggressively service Ryan's puckered hole, pushing his tongue into its tightness.
"How does that feel, Ryan?" Bruce asked. "How does it feel to have your twink friend sucking your ass?"
"It's nice." Ryan answered. "I really like having his tongue inside me."
Bruce reached out and had a quick feel of the bulge in Ryan's jockstrap.
"It seems your penis is getting excited."
"Oh yeah. I'm definitely getting a boner." Ryan admitted.
Jake was still making out with Ryan's anus, his own dick twitching in his thong as he tasted his friend's hole. He then licked up and down the entire length of Ryan's butt crack.
"Damn you taste good!" Jake exclaimed.
"Thanks, man."
Jake kissed Ryan's anus again before reinserting his tongue. Bruce put his hand on the back of Jake's head, helping to keep his face firmly buried in Ryan's ass. He kept his hand there for a minute or two before pulling it back so Jake could catch his breath.
"Don't forget about all the toys we have, Jake." Bruce said. "There are plenty of things you could stick in Ryan's butt."
"I think Jake needs something in his butt, too." Ryan suggested.
"That's a great idea!" Bruce agreed. "And I believe we have something that will accommodate you both."
The coach picked up the 15" double-sided dildo from the coffee table and waved it around in front of them.
"Why don't you boys get on all fours?" Bruce suggested. "Let us see you having some ass to ass fun together?"
"Sounds good to me." Ryan said.
Ryan joined Jake on his knees and they faced away from each other while Bruce lubed up the dildo. He pulled Jake's thong out of his crack so he could access the boy's anus.
"Here it comes, Jake."
Bruce slid the first half of the dong into Jake's bottom. It went in easily.
"I love how Jake's ass basically sucked that dildo right in." Cliff commented.
"It sure did." Bruce agreed. "Your turn, Ryan. Ready for me to put this in your ass?"
"Yes please!"
Bruce chuckled at Ryan's enthusiasm as he began to insert the toy. Ryan's anus was slightly more stubborn than Jake's, but Bruce was persistent and ultimately successful in injecting the other half of the toy penis into Ryan's asshole.
"Perfect!" Bruce exclaimed. "You each have about seven and a half inches of dildo up your butts. And now you can slide back and forth, fucking yourselves as well as each other."
The boys acknowledged their cue and began to move back and force, each one sliding up and down their half of the dildo. When they pushed back, they went far enough that their butts would briefly touch.
"I just love watching two young, gay friends playing together." Bruce said. "Look at them go! Just slamming their asses on that dong."
Bruce took off his shirt, drawing the attention of Cliff and the camera. Bruce did not disappointing, removing his pants next and revealing his thick, rigid, nine-inch penis. This inspired Kevin, who also went ahead and got undressed.
"Now it's turning into a party!" Cliff said, getting some shots of Kevin's nude body.
Jake and Ryan continued to ride their dildo while Bruce observed them. Kevin quietly made his way over and knelt down, starting to kiss and lick Bruce's amazing cock.
"I like the way you think, Kevin." Bruce told his friend.
Kevin leaned in and kissed each of Bruce's balls. He then opened his mouth and slid it down Bruce's dick.
"Oh yeah. That's the stuff." Bruce encouraged. "Suck my cock."
Cliff zoomed in on Kevin's lips sliding up and down the thick penis with lust and passion. Kevin moaned with delight as he slurped on the magnificent dick.
Jake and Ryan were really bouncing on their shared dildo at this point, both of them heavily panting.
"I think I'm about to cum." Ryan said.
"I definitely am." Jake added.
Kevin happily continued with his blowjob as Bruce watched the boys moaning and climaxing together, soiling their respective underwear.
As the effects of their orgasm waned, Jake and Ryan slowly took the dildo out of their butts and stood up.
"That was intense." Ryan said. "But fun!"
"Now you should trade." Bruce told them. "And lick up each other's mess."
The boys again were agreeable, each of them removing their underwear. Ryan took off his shirt and handed his jockstrap to Jake while Jake offered Ryan his dirty thong. Cliff focused the camera on the boys.
Jake went first, lifting the jockstrap to his face and sucking every drop of cum he could muster from the crotch. Ryan then took his turn, lifting Jake's thong panties up and sucking up his fresh sperm.
"That was really cute watching you guys eat each other's cum." Cliff said. "Would you be interested in more?"
"Of course!" Jake answered.
"If you help me out of these pants, you boys can suck my cock together." Cliff added.
Jake excitedly unbuttoned and unzipped Cliff's pants, pulling them down and helping him get them off. Cliff then took a seat on the couch as the two boys knelt down on either side of him, admiring his erection.
"You have a nice cock."
"Thank you, Ryan. That's very sweet." Cliff said. "Jake certainly enjoyed it the last time we had sex. I bet you'll enjoy it too."
Jake began to suck on Cliff's balls, leaving the shaft to his friend. Ryan licked his lips in preparation and then leaned in, taking the penis into his mouth.
Meanwhile Bruce was enjoying his blowjob, holding Kevin's head with both hands and thrusting his meat in and out, basically fucking his face.
"That's it. Take that dick." Bruce demanded.