Interracial

Uncovering His Identity Chapter 7:

Jake experiences another imagined scenario.

Spankmasters
May 17, 2024
35 min read
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Discovering Himself Ch. 07
Discovering Himself Ch. 07

Uncovering His Identity Chapter 7:

Jake roused out of bed, pulled back the covers, and sat up at the side of his mattress. He glanced down at his morning erection, which seemed a bit stiffer and more energized than usual. Then, he glanced behind him at Ryan, still asleep and as naked as Jake.

Jake took a moment to recall the previous night's events. He and Ryan had spent a fantastic evening engaged in sex and debauchery. They had given each other oral. They had had intercourse with each other. They had tasted each other's bodies and sexual fluids. And when they were through, they had shared a passionate kiss and drained off to sleep completely undressed.

For a second, Jake had a desire to walk over to Ryan's side of the bed and masturbate onto his friend. That desire quickly receded, and he opted to let his trusty companion rest and recuperate from what had been a sensational sex-a-thon.

Standing up from the bed, Jake proceeded toward his dresser. He opened the upper drawer and extracted a fresh pair of undies: lilac bikini briefs. Although his erection was starting to wane, he still had to maneuver his masculinity to fit snugly within the confines of his underwear. He then donned a white t-shirt and made his way to the kitchen in search of coffee.

As Jake strode into the kitchen, he found his coach and mom sitting at the table eating breakfast.

"Good morning, dudes!"

"Morning, boy!" Bruce replied with a wave.

"Morning, sweetie." Kathy said, peering at her son and smiling. "I see your entire... endowment... is reasonably visible through your underpants."

"Jeez, mom. Are you seriously getting nitpicky about my outfit?"

"Hello, pot. You're kettle shouldn't be calling black pot black." Bruce quipped. "Let the young lad flaunt his body. He looks great in those panties."

"Fair enough." Kathy said, agreeing. "I probably shouldn't be judgmental, right?"

Jake picked up a coffee mug and filled it with hot, steamy coffee, adding a tad of sugar and cream.

"So, honey..." Kathy commenced. "I noticed Ryan's car here last night. And it's still here this morning. Does that mean what I believe it means?"

"Just signifies he spent the night." Jake said with a naughty smirk.

"Don't try to evade it, lad. You know I'm asking. Did you engage in a conversation with him? Did you have quality time by yourself?" Kathy added with a chuckle. "If you're not wearing pants, I must assume you had a fantastic encounter with your mate."

Jake turned crimson as he sipped his coffee. He could hardly contain his excitement.

"It was an extremely gratifying experience." Jake commented. "We spent the entire night discovering one another's bodies. From head to toe. Every crevice and hollow. It was passionate and breathtaking. We were both exuding sweat and stickiness when we conked out together."

"Yay! You and Ryan! That's delightful!" Kathy stated. "I'm overjoyed that your fanciful goals were realized."

"Thank you, mom!"

"Is Ryan gay like you?" Kathy inquired.

"Not exactly." Jake answered, taking another swig of his coffee. "He likes females he said. However, he viewed your porn scene and desired to experience intercourse with another guy, so we essentially took turns screwing each other the entire night, and he truly relished it."

"Cool!" Kathy remarked. "So Ryan is bisexual like me. I'm pleased you, Jake."

"Thanks, mom!"

"So, are you two an item now?" Kathy asked. "Are you and Ryan going to start dating since you're having sex?"

"I don't know if he wants to be my boyfriend." Jake replied. "But we're definitely going to be having more sex together."

"Maybe I should take you chaps to my cabin this weekend." Bruce suggested. "I might invite Kevin and Cliff... we could make it a testosterone-fueled weekend."

"That sounds superb, coach." Jake noted, imagining himself surrounded by four completely naked and horny blokes. "I should probably check on Ryan. I'll mention the cabin and ascertain if he'd be interested."

"Have a great time pleasuring your friend," Kathy told her son.

"Here's to more homosexual sex for you, Jake!" Bruce added, drinking from his coffee cup. "It's going to be a guy's weekend!"

Jake held his cup in salute before releasing a trace of his coffee. He resumed his walk, returning to his bedroom. There, he could discern Ryan's silhouette in the darkness, fanning through his homosexual pictorial. Underneath the blankets, Ryan's hand moved with more enthusiasm than discretion; his manhood made a bold cylindrical shape.

"Having a good time?" Inquired Jake.

"Obviously!" Ryan taunted. "I couldn't help it; I woke up aroused as hell and your magazine was handy."

"No biggie." Repeated Jake with cordiality. "This publication is intended for stimulation and your interest is well taken. Sometimes I think there's a bit more homosexuality in me than I care to admit."

Ryan set the magazine aside and received the sheet that was shielding their friend's nudity. Instructionally, Jake raised the rag, exposing Ryan's member.

"Jesus, check that out!" Jake exclaimed. "What a glorious phallus."

Ryan eased his appendage from his grasp. Jake positioned carefully on the mattress adjacent to Ryan. Jake moist his palm with spittle and began to administer the lube by engulfing Ryan's penis in its slipperiness.

"Always thought you'd like it rough," mused Jake.

Ryan chuckled. "I hadn't before, but if you're gonna do it, that's what I would prefer. Stroke the fuck out of this."

Jake casually bent his hand into a fist and emulated powerful jacking motions. Ryan's penis throbbed fiercely in Jake's hand. They discussed the picture he previously laid eyes on, the first one of a dude with a gargantuan posterior, which seemed to comfortably contain a prodigious cock.

"I've never seen a butthole that stretched like that before," mentioned Jake. "I wonder how that guy managed such a feat."

"The amount of male dicks within and outside of her ass, for sure!" Agreed Ryan. "There's a certain degree of endurance and formidable talent associated with that gent. It blows my mind in the very best sense."

Jake then shifted his dexterity to the testes of his friend, provoking a passionate reaction. He also reviewed the following few images: one of an erect penis projecting from slacks, another of a nude lad beside a laptop, working on his pole, and the last of a threesome in which one man sandwiched in between two others, both penetrating him.

"I can't fathom the pleasure of participating in such activities," pondered Ryan.

In unison, both of them considered the concept of interchanging roles. "Getting penetrated while also fucking sounds out of this world." Jake insisted. "I also wouldn't mind seeing many cocks in my mouth."

Ryan delighted in having his jerk-off administered. Increasingly Jake sped up his performance.

Ryan sank down and approached climax. "I'm going to come!" he cautioned.

"I want to taste it." Urged Jake. "Cum for me and I'll eat your stuff."

Jake's grip on Ryan's pole became fervent, and he took Ryan's entire tool into his face. Jake's mouth slid over the head, the pictures of male arousal and excited bodies serving as a background. Jake's tongue poked deeper and deeper, until he began to taste the semen and Ryan's quivers wracked him. Slick, nauseating juices infused inside Jake's mouth and soon surpassed. Upcoming was a sticky gush that Jake used with fervor to curtail any redundant loss. His tastebuds were overwhelmed with the juicy, overwhelming flavor of sustenance to him the next few minutes, as he ingested a little more residue.

Jake sped up his jerks and the visuals in the masculine pictorials progressed simultaneously. Ryan foraged among the array of erotic acts and selected one of two men sharing a passionate embrace in a sincere, tender, oral exchange. They also observed a youth on his knees busy with the cocks of intermingling males. Ultimately, a final threesome, of one man penetrating and another receiving.

"I truly admire those pairings; however, the concept of a butt penetrated simultaneously by two individuals is oh so tantalizing!" Fresh arousal overwhelmed Ryan.

Jake's motions intensified; the video rapidly neared the moment and he used all strength in his wrist to compel Ryan to emit a copious substance. Ryan began his release. Jake jerked harder. Jake's mouth quickly captured incoming cum, the liquid deposits being slurped and swallowed. Ryan's cock jerked expressing the final fate of his spent penis, and Jake took it in his mouth to claim the remainder.

"I never thought I'd want to film porn, but today here I am," declared Jake.

"Well, if you ever do, maybe we can help you find those kinds of thrilling experiences," encouraged Ryan.

Jake continued to service Ryan. A threesome wherein one act penetrated a bottom while another accosted the same individual. Ryan started to pound on the bed in ejaculation and suddenly collapsed, https://casinodaddy.com/online-bingo/ exhausted. Both craved each other's faces, in an embrace and spoke passionately about what they'd just witnessed.

Jake took his dick out and sat back, grinning at Ryan.

"Mmm, tasty!" He declared. "How about this coach's proposal, Ryan? Would you be keen on spending a weekend with me and three other men?"

Now it was Ryan's turn to wear a smile.

"That does sound super sexy. I've got an idea." Ryan said. "I'll agree to this cabin retreat, but only if you return the favor and ejaculate into my mouth right now."

"Agreed!"

Jake stood and pulled his panties a tad lower, exposing his hard member. Ryan lay on the pillow with his head resting on it, opening his mouth. Jake started touching himself as he moved towards the headboard. He pointed his penis towards Ryan's mouth as he started stroking himself.

"So should I just shoot it straight in there?"

"Yeah, that would be great." Ryan replied. "And after swallowing mine, I want to swallow yours too."

"Sure."

Jake asked, "You understand what this weekend entails, right?" while he jerked off. "It's going to be a longer orgy of dirty gay sex than we had last night. And Coach Campbell probably expects you to bend over for him so he can fuck you with his big cock."

"I get it, I got a taste of gay sex last night. Might as well dive straight in." Ryan said. "But for now, I'll focus on you and your release."

"I'll comply with that request."

Jake quickened his stroking as he knew he was close to climaxing.

"Freeze." He commanded. "Here it comes!"

Jake's penis spasmed as a substantial amount of cum ejaculated from his penis and went directly into Ryan's mouth. A smaller squirt followed, with Jake slowing the jerking motion. Having left some sticky drops of semen in his urethra, Jake dabbed them with his finger and smeared them on Ryan's lips.

Ryan closed his mouth and swallowed the salty paste. Then he licked his lips as he opened his eyes. Jake pulled his panties back up.

"That was great." Ryan remarked. "Thank you for sharing it with me."

"Obliged. Thanks for letting me pleasure you with my hand." Jake said. "And remember our agreement - you must come with me to the cabin this weekend."

Ryan stood up, his soft penis hanging loosely, and began to put on his clothes.

"No worries. I'm a man of my word." Ryan summed up. "Though I'd better get started on my chores. I suppose I should be getting home sometime."

"Before you go..." Jake hesitantly interjected. "... I'd like to kiss you again."

"Then don't waste time! Say it and do it!" Ryan urged.

Smiling, they embraced and locked lips. Jake slid his hand down Ryan's backside, squeezing his buttocks through his pants. Ryan grabbed Jake, his hands moving under the smooth fabric of the coach's underwear, pressing against the bottom his butt cheeks. They parted and worked on each other's tongues before breaking their hug.

Jake waved goodbye to Ryan as he got dressed and picked up his things.

The following two days felt like forever as Jake waited for the weekend to arrive. Eventually, it did, and they were just a few miles from the property.

Bruce offered to drive Jake and Ryan and they both accepted his offer. Bruce was driving while Jake and Ryan were on the back seat.

"We should arrive any moment now." Bruce informed. "Are you guys excited?"

"I'm really excited!" Jake beamed.

"I'm really excited as well, Coach." Ryan concurred. "I've had an erection for almost this entire ride."

"If you'd only mentioned it earlier, Jake, I could've given Ryan a blowjob." Bruce mentioned. "However, since we're approaching the cabin, we don't have enough time to do that."

"Sorry, Coach."

"It's fine." Coach Bruce said. "But see this as a teaching moment. If you don't speak about your feelings and desires, you'll never have the opportunity to uncover them. You didn't express your horniness, so you missed your chance for a blowjob."

"That makes sense to me." Ryan agreed. "I'll work on being more forthcoming in the future."

Coach Bruce heartily laughed. "Excellent, boy. Now Jake, I presume Cliff is bringing some recording equipment. Probably more than one camera. He wants to film video and make a documentary of your first time engaging in a gay orgy. How does that sound to you?"

"That sounds fucking incredible!"

Bruce commented, "That's the response I anticipated." He confided in him. "This is yet another opportunity to demonstrate to the world how perverse you can be."

"I'll give it my best effort!"

"I trust you," Bruce added. "And there's also going to be a lot of sex happening throughout the weekend. Ryan, please don't get the wrong idea, but I'm anticipating giving your asymptotic rectum quite a thorough spanking this weekend."

"I'd guessed it as well, coach," Ryan replied. "I'm looking forward to it."

Jake reached out and took Ryan's hand, embracing each other. Bruce turned the steering wheel and parked in the driveway of the cabin. Kevin and Cliff were already there with their cars parked.

"There's no other house for miles," Bruce said. "So don't hesitate to be naked outside or anything like that. Maybe even have sex outside. No one will likely see you."

Bruce turned off the vehicle and everyone exited, grabbing their personal belongings. They approached 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: various lubes, plugs, beads, vibrators, toy cocks of various sizes, and even a double-ended dildo.

Jake also realized that Bruce was accurate about Cliff, as several video cameras were plugged in and charging. Jake greeted Kevin and Cliff with a friendly embrace.

"It's wonderful you were able to attend," Bruce remarked. "Let's give these boys an unforgettable weekend of anal".

"Definitely the goal!" Kevin added with a laugh.

Jake and Ryan shared the same enthusiasm, exchanging a high five.

"Should we all undress and just start fucking?" Jake jokingly asked.

The other men had a hearty laugh at Jake's suggestion, and Bruce swatted his bottom.

"There'll be plenty of cock easing its entrance into your slutty rectum this weekend," Bruce retorted. "But first... did you bring something seductive to wear? Attempt to stimulate us rather than simply receiving."

Jake grinned and blushed at the challenge.

"I can do that. I've got a fantastic idea for a suggestive outfit I can put on," Jake said.

"Mind if I accompany you, Jake?" Cliff inquired. "I could capture your outfit change and ask dirty questions."

"Go ahead."

Jake took his suitcase and Cliff took one of his cameras. The two of them proceeded to a bedroom. Jake placed his suitcase on the bed and unzipped it, while Cliff prepared the camera.

"You'll know I'm recording when I begin asking you questions," Cliff clarified. "Just remove your clothing and change as you usually would while answering."

Jake began pulling out items from his suitcase. Cliff began recording.

"Welcome back, gents! It's Jake!"

Jake smiled, waving at the camera.

"Hi, hunky men," he said. "I hope you're prepared for more scorching, luscious activity."

"He's not fibbing," Cliff added. "Jake's here with four other lusty men attending an overflowing orgy." Are you thrilled to experience your first gay orgy?

"Extremely excited!" Jake proclaimed. "An entire weekend with four cocks to suck and fuck with mercy? That's a childhood dream for a lad like me."

"I can attest to that." Cliff chimed. "And Jake started a gay OnlyFan account, how's that going?"

"Fantastically well," Jake answered.

Jake pulled down his jeans and removed his shirt.

"So, how much cock have you sucked since our last encounter? If you had to guess," Cliff enquired.

"To answer that question, there's only one option," Jake replied, tugging his jeans down and displaying his purple panties with black lace. "How much cock have I sucked? Not nearly enough!"

Cliff snickered as Jake took off his jeans completely.

"That response is delightful," Cliff complimented. "Still donning those panties? I can't wait to reload some cum into that arse once again."

"And me, too!" he responded.

Jake turned around, providing the camera with a glimpse of his bottom as he removed his underwear.

"Here's Jake's juvenile, gay rump," Cliff commented. "I can't wait to bury my cock deep into that thing again."

Jake faced the camera again and picked up the items he had removed from his suitcase.

"So, what kind of outfit did you choose?" queried Cliff.

"I wanted to try something enjoyable and cute. I brought some thigh-high stockings, a garter belt, and a thong."

"That sounds fascinating," Cliff approved. "And Bruce informed me you began a gay OnlyFans account. How's that progressing?"

Jake chuckled, "I think this whole venture is off to a good start." Scheduling his stockings, he was close to hitting the 100-subscriber milestone. Currently, it was running free, allowing potential fans a secure chance to check it out.

Beginning with the first stocking, he rolled it up his thigh.

"A developing subscriber base is awesome." Cliff weighed in. "Has anyone reached out to you?"

"Ah, yep, a couple people have made comments or messaged me." Jake recalled, adding the second stocking. "One guy is married but hiding in the closet. He said I reminded him of his son but unfortunately, his son wasn't gay. He advised I record a video addressing the camera as 'Daddy' and discussing how I've been a naughty boy and needed Daddy to chastise me."

"That sounds kinky."

"Yeah, I need to create that video for him." Jake mentioned, hooking up his garter belt to the stockings. "It sounds like he's ready to tug away while envisioning me as his son and me pleading for his cock."

Gathering the thong, Jake slipped it on, fighting to squeeze his package into the front of the garment.

"How do I look?"

"Like a teenage guy who'd love some cock." Cliff responded. "Rotate around. Let's examine that ass again."

Jake obeyed, showcasing his nude butt cheeks, leaving everyone to view the thin waistband tucked in between his cheeks.

"So these are your assets." Bruce grinned, "Jake, join us in the living room. Allow the others to observe you dressed as a horny, dirty slut."

Jake giggled and moved toward the hallway, where Cliff trailed behind, the camera poised to capture his swaying buns.

Returning to the lounge, Jake found Ryan had removed his pants, leaving him draped in only a white shirt and a jockstrap that revealed his whole rear end. Bruce and Kevin were distracting Ryan, palpating all over his torso and examining his male parts.

"Bruce, here's your street urchin!" Bruce abruptly declared, observing Jake's ensemble. "You look brilliant, Jake."

"Thanks, coach."

"You look fucking hot." Ryan agreed.

Jake curtsied in gratitude for their compliments.

"How about exploring your friend's butt, Jake?" Bruce proposed. "Given your love for rears, how about you get behind Ryan, presenting him how you adore a fabulous ass?"

"Yes, sir."

Jake kneeled down behind Ryan's posterior. Cliff held his weapon at the right angle to film the action. Jake snuggled his head into Ryan's gaping rump.

He initiated with a deep inhalation of Ryan's anal odor.

"Bruce, how's Ryan's butt smell?" Inquired Bruce. "Does it smell delicious?"

"It's heavenly." Jake replied, sampling Ryan's butt again. "I imagine it tastes even better."

Jake plunged his face into Ryan's crack, licking, kissing, and tonguing his asshole. It seemed as if Jake was dying of hunger, with Ryan's asshole being his ideal dish. Jake worked on opening Ryan's cheeks to access his friend's anus more readily.

"Does that feel right, Ryan?" Checked Bruce. "Knowing your friend is licking your asshole?"

"It feels fine." Ryan conveyed. "I appreciate having your tongue inserted into my anus."

Bruce caressed the engorged tent in Ryan's jockstrap.

"Your trouser snake is growing."

"Indeed. I'm getting a hardon." Ryan verified.

Jake persisted championing Ryan's puckered hole, tonguing it with great passion.

"How does it feel, Ryan?" Asked Bruce. "How does it feel to have your friend tonguing your asshole?"

"It's okay." Ryan responded. "I enjoy having his tongue within me."

Bruce held the back of Jake's skull, assisting in keeping his face in Ryan's backside. He extended his grip for a minute or two before releasing it, enabling Jake to catch some breath.

"Don't forget all the items we possess, Jake." Bruce instructed. "We've got numerous things suitable for your and Ryan's butts."

"I think Jake could use something in his butt, too." Ryan recommended.

"That's an excellent thought!" Bruce acknowledged. "And we've got an instrument that will suit you both."

The coach picked up the 15-inch double-sided dildo from the coffee table and waved it in front of them.

"Let's all get on all fours," Bruce suggested. "Watch us have some ass-to-ass fun together."

"Go for it," Ryan replied.

Ryan joined Jake, both of them on their knees and facing away from each other. Bruce lubed up the dildo, pulling Jake's thong aside so he could reach the boy's anus.

"Here it comes, Jake," Bruce said.

He inserted the first half of the toy into Jake's bottom, which slid in easily.

"I love how Jake's ass just sucks that dildo in," Cliff commented.

"Yup, it did," Bruce agreed. "Now it's your turn, Ryan. Are you ready for me to put this in your ass?"

"Yes, please!"

Bruce chuckled at Ryan's eager tone as he began to insert the toy. Ryan's anus was slightly more stubborn, but Bruce persisted and managed to insert the other half of the toy penis into Ryan's asshole.

"Great!" Bruce exclaimed. "Each of you has about seven and a half inches of dildo up your butts now. Go back and forth and fuck yourselves while you're at it."

The boys began to slide back and forth, each one sliding up and down their half of the dildo. When they pushed back, their butts briefly touched.

"This is just amazing," Bruce remarked. "Two young, gay friends having fun together. Watch them go - they're really slamming their asses on that dildo!"

Bruce removed his shirt, catching Cliff and the camera's attention. The next thing he did was take off his pants, revealing his large, rigid, nine-inch penis. This prompted Kevin to undress as well.

"This is turning into a party!" Cliff exclaimed, filming Kevin's naked body.

Jake and Ryan continued riding their shared dildo while Bruce observed them. Kevin gently moved over and knelt down, kissing and licking Bruce's incredible cock.

"Well done, Kevin," Bruce praised his friend.

Kevin leaned in and kissed each of Bruce's balls. Then he opened his mouth and slid it down Bruce's dick.

"Yes, suck my cock," Bruce urged.

Cliff zoomed in on Kevin's lips sliding up and down the thick dick with desire and passion. Kevin moaned with pleasure as he indulged in the amazing dick.

Jake and Ryan were now really bouncing on their shared dildo, both of them heavily panting.

"I think I'm about to cum," Ryan stated.

"Me too," Jake added.

Kevin continued his blowjob as Bruce watched the boys moaning and climaxing together, soiling their underwear.

As the effects of their orgasm subsided, Jake and Ryan removed the dildo from their butts and stood up.

"That was intense, but fun!" Ryan said.

"Right," Jake agreed.

Bruce told them to swap their cum-soaked underwear. Jake 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 was the first to drink cum, lifting the jockstrap to his face and sucking every drop he could find from its crotch. Then Ryan took his turn, lifting Jake's thong to his face and drinking up Jake's semen.

"That was adorable, watching you guys drink each other's cum," Cliff said. "Would you be interested in more?"

"Absolutely!" Jake answered.

"If you two can help me out of these pants, you can suck my dick together," Cliff added.

Jake took the initiative, unbuttoning and unzipping Cliff's pants, helping him get them off. Then Cliff sat on the couch as the two boys knelt down on either side of him, adoring his erection.

"Wow, you have a nice cock," Ryan said.

"Thanks, Ryan," replied Cliff. "Jake certainly enjoyed it the last time we had sex. I bet you'll enjoy it as well."

Jake started sucking on Cliff's balls while Ryan aimed for the shaft.

Meanwhile, Bruce was still receiving a blowjob, holding Kevin's head with both hands and thrusting his meat into his mouth.

"That's it. Take that dick." Bruce commanded.

Bruce groaned and Kevin gagged for a second before swallowing Bruce's entire load. Kevin disengaged his mouth from the cock.

With the blowjob over, Kevin then turned his attention to the boys sucking each other. His gaze then shifted to Jake's exposed ass, more defined by his garter belt and stockings. Kevin crawled over, aimed, and slid his entire penis into Jake's bottom.

Jake was a bit taken aback by the suddenness, but quickly relaxed and began to enjoy the penetration.

"Jake, he just rammed his entire dick in there in one thrust and you didn't even flinch," Cliff remarked. "I'm impressed, Jake!"

Here's your paraphrased text:

Bruce chimed in, "That's how you recognize a guy who's taken a lot of cock up his tight hole."

As Jake and Ryan kept bobbing their heads up and down on each side of Cliff's shaft, Kevin was pounding his dick repeatedly into Jake's booty. Bruce took one of the cameras to film this spectacle. Cliff's other camera was also recording the pair taking turns blowing each other's cocks. Bruce also filmed Jake's cock and balls bouncing with each push from Kevin's dick.

Jake took a moment to hold Cliff's penis still, allowing Ryan to move from his emergency stop to parking on it. Jake could then suck Cliff's dick with all his might.

"This cock feels fucking incredible in my ass!" Jake yelled out. "Don't be scared; use me as hard as you want."

Ryan switched from sucking on Cliff's schlong to his sac, giving Jake a go at sucking off the tall guy's penis. Kevin upped the intensity, slamming his dick further and harder into Jake's butthole.

Jake loved having both his holes chock-full of thick, stiff cocks. He munched on Cliff's big dick while getting his rear tampered by Kevin. Jake tasted Cliff's precum on his tongue, spurring him to suck even harder.

"Go on, Jake. I'm close." Cliff encouraged.

Jake maintained his lock on Cliff's dick, his mouth sealed around the shaft. He felt Cliff's dick jump just before releasing a thick, creamy load into his mouth. Another rich shot of semen joined the first.

Jake kept the semen in his mouth and climbed off the fetish-loving lad's dick. He turned to Ryan and leaned over, sharing a slobbery kiss with his pal. They shared Cliff's stash of cum as Kevin drilled Jake's rear with unrelenting force.

"Watching you guys make out is adorable." Bruce said. "After all, remember that there's another load you can share?"

Jake and Ryan broke contact. He looked back at his mentor.

"What do you mean?"

"Remember Kevin just busted a nut inside your hole." Bruce calmly explained. "You should sit on Ryan's face, pushing the cum out of you."

Jake nodded and turned back to Ryan.

"Do you want me to fart Kevin's load straight into your mouth?"

"Yes, dude!" Ryan replied. "I want to taste cum from your ass."

The amigos shared a heated smooch.

"So sweet and homoerotic." Cliff commented. "Lasting sights for the memory bank."

Jake rose up and perched above Ryan's face. He hunched his buttocks over the gay guy's mouth, letting the cum slide out. With minimal effort thanks to his loosened ass, Jake expelled a large gob of semen into Ryan's open mouth. After his friend got up, the duo remained intertwined, returning for another make-out session, and tongue-swapping of a new batch of sperm.

"Check out that nasty duo. Jake and Ryan sharing jizz coming straight out of Jake's asshole." Bruce proclaimed. "Isn't that divine?"

Jake and Ryan embraced with asses in their hands.

"Lovely young, homoerotic courtships." Cliff remarked, placing his gear down.

Ryan peered at Bruce's quivering tool right below his waist.

"Anything wrong?" Bruce asked, putting his camera down.

"No, coach." Ryan answered, unsettled at the massive tool. "I'm just excited and a little nervous that you're about to take my virgin hole. I see Cliff’s and Jake’s holes are stretched from all their use. I place my faith in their experiences."

Bruce chuckled at Ryan's angst.

"It'll be fine. Jake takes it up his ass often. Easily." Bruce assured. "I'll be gentle with you at first. Until you're ready for a more intense experience."

"That's true." Ryan affirmed with a relieved heave. "It's just a cock, right? A big, long, thick cock."

"Woohoo!" shouted Bruce.

"I could definitely use something to drink," stated Kevin.

"You've got it figured out, my friend." said Cliff. "Let's check out the fridge."

Kevin and Cliff made their way to the kitchen. Jake didn't miss the opportunity to admire the two of them as they walked away. As soon as they were out of sight, he turned back to his coach and buddy.

"Wow, you're looking good in that garter belt and stockings, Jake." Bruce stated. "They highlight your submissive nature. Maybe you should explore different kinds of clothing like nightgowns, bodystockings, and various crotchless underwear so you can show off your penis."

Jake blushed at the praise and the salacious recommendations.

"I'd be interested in expanding my wardrobe and trying those things." he said. "Or perhaps even a costume, like a naughty schoolgirl who needs to be punished."

"Sounds nice," Bruce agreed with a grin. "You could dress up as a French maid and do some chores for me. I imagine you on your knees scrubbing my toilet with your [cheeks] wagging in the air, begging for me to slide my penis in."

"I can imagine that." Jake replied. "Of course, I'd probably overlook a spot or two and need some discipline. So you'd give me a spanking to ensure I learn my lesson before cleaning your penis, ass, and balls with my tongue."

"Your dirty mind amazes me," Bruce said.

"Me too, coach." Jake responded. "Let's get Ryan involved. Perhaps he'd like to try out your cock?"

Bruce viewed the proposal favorably.

"We could certainly make room for him." he offered.

Ryan leaned forward, thrilled by the idea.

"Please allow me to play with it, sir." Ryan requested, already stroking Bruce's semi-erect penis when Bruce motioned to sit next to him.

Jake observed how Ryan held Bruce's erection in his hand and concentrated on its width.

"Would you like to see if you could get it to stand up tall?" Bruce encouraged.

Ryan seemed unable to speak, only nodding yes. He kept his hand on Bruce's penis as if stroking it.

Cliff and Kevin returned to the living room. "It's about time we record this!" Cliff announced. "Give me the camera and I'll capture it."

He moved to capture Ryan's hand moving up and down the substantial shaft.

"How do you find that, Ryan?” Cliff asked, "That cock in your hand?"

"It's a nice penis." Ryan responded, still stroking Bruce's manhood. "I've heard so many good things about yours from Jake. Now I get to experience it first-hand."

"Why not continue your hand job on your knees in front of Bruce?" Bruce suggested. "So Jake can lube your butthole before we all have a turn to fuck you."

Ryan obeyed, climbing back onto the floor while rubbing Bruce's cock before him. Ryan was clearly enthralled by its size, so much so that he decided to kiss the tip as he stopped stroking.

Cliff zoomed in on Jake pouring some lube onto Ryan's butthole. He then worked the lube into it with his hands, ensuring that ample lubrication was used to prepare Ryan's anal canal.

"It does look adorable drunk," Cliff joked.

Jake squirted more lube onto Ryan's rear and began probing his butt.

"It seems that the size of your partner's penis was nothing compared to this," Jake said, making sure Ryan was slick and ready for gay intercourse.

Cliff focused the camera on Ryan's hand, still gently stroking Bruce's fully erect penis, and his other hand groping Bruce's impressive testicles.

"Looks like a great pair of balls," Cliff commented, impressed by their fullness. "I guess we'd better empty them then."

"Do you want to help me empty my balls, Ryan?" Bruce asked. "Pour some here."

"I think so," Ryan answered.

Bruce had used this position before to introduce his cock to Jake. "Remember, take it slow," Bruce reminded. "Allowing yourself to lower yourself down my cock as you're ready gives you control."

Jake made certain Ryan's backside was oiled up. "We believe you have a pretty little bottom, don't you think?” he asked his friend. “I look forward to watching you with this massive cock."

Ryan appeared excited, kneeling down and allowing Bruce's penis to slowly slide into his anus.

Jake continued to apply lube to Ryan's ass, ensuring that everything was lubed.

"Nice ass," Cliff told Ryan.

"I like it too," Jake confirmed, entering Ryan from behind.

"Now it's your turn to film," Bruce requested, as he and Jake burned some lines in Ryan's desperate ass.

Cliff positioned himself behind Bruce to film the action as Ryan struggled to accommodate them.

Rylan moved over Bruce's legs, facing the coach. His hand gently rested on Rylan's hips as he prepared for what was about to follow.

"Jakie, sweetie, would you mind assisting me by guiding my penis into your friend's rectum?" Bruce asked.

"Absolutely!" Jakie replied, instantly reaching towards Bruce's erection and gripping the base of it.

Rylan started to sit down a little, feeling the tip of Bruce's cock press against his anus. He took a deep breath and paused for a moment.

Bruce offered some reassurance to his student. "Easy does it, dear. There's no need to hurry. It's just a regular penis going inside your anal cavity. You want my penis in your ass, right?"

"Yes, I do. I really want your penis in my ass." Rylan replied confidently.

The head of Bruce's shaft slowly entered Rylan's opening, making him gasp slightly from the sensation.

"Perfect," Bruce said. "Don't stress about it too much. All you need to do is relax and welcome the penis."

Jakie had some memories of his own. "Can't say I'm not feeling some nostalgia, Cliff. This is reminding me of when both of you fucked me together."

"I'm sure we can recreate the experience," Cliff suggested, giving him a nudge.

Jackie couldn't help but think about two guys fucking him at once. "Good lord, Cliff. I've thought about it before, but I never really imagined I'd ever get to enjoy having two cocks in my butt."

In the meantime, Cliff undid the spare Condom Paak from his jeans and handed it to Kevin. "Now's your turn, buddy."

Kevin smirked, stepping closer to the couch and aligning himself with Rylan's backside. Grabbing the base of his erection, he lined it up with Rylan's stretched-out anus and began to thrust patiently and gently.

"Now," Cliff declared, positioned behind Jake, "I'll go next."

As Cliff started to enter Jake, Rylan was almost fully seated on Bruce's cock. The feeling of the thick dick inside him gave Rylan a sense of achievement.

He glanced back at Jakie as if sharing the sentiment. "This feels amazing."

"I'm not surprised. You've had a lot of practice with it." Jakie grinned. "I hope your sweet hash brownie is enjoying himself."

"Who are you calling a hash brownie?!" Rylan joked, clenching his hips and pumping up and down on Bruce's phallus.

As Bruce stared lovingly at Rylan, he looked over at Jakie and wittily stated, "You know, I was thinking... Jake, you really enjoy getting fucked by big men."

"I'm not usually against it," Jakie admitted and giggled,"It never hurts to dream a bit about being fucked by two big guys with huge dicks at once."

Ryan embraced Jake's hand and beamed in delight as he rode Bruce's cock. Kevin and Cliff were vigorously fucking him one after the other, giving his ass a satisfaction it had never experienced before.

"I'm almost there, coach." Rylan reminded.

Bruce, feeling his climax approaching as well, said, "Go ahead and cum, Ryan."

Rylan began to buck back and forth, damn near fucking Bruce's cock out of him.

"Hold on! We're not done yet!" Bruce exhorted his protégé.

"I'm not stopping until you've covered me!" Rylan pleaded.

To stop him, Bruce firmly planted his hand on Rylan's back, pushing him slightly upwards, making him semi-erect before lowering him back down.

"Good boy," Bruce praised. "Now you've got your coach's cum all in your butt."

Jakie added, "You should also feel Kevin's dick fucking you in the back."

Rylan giggled nervously, "Yes, and I can hear Cliff getting ready to thrust into me as well."

Bruce quipped, "Well, it seems we have a couple of horn dogs who are about to enter the fray."

Kevin and Cliff both became far more forceful with Jake, thrusting his cock inside him so deeply that it produced an orgasmic gasp from him.

Four of them remained silent, immersed in their pleasure.

"Dear Jake," Bruce said, "I think I'm about to come."

"Do it, Coach," Rylan encouraged. "Fill my ass with your hot sperm."

Hearing Rylan's words, Bruce climaxed, filling him up. All the while, Cliff added his involvement, pummeling Jake's anus with his stiff shaft. Eventually, Cliff also released with an audible shout as he came. Kevin wasn't far behind, adding his own nut to the mix. All three men had filled Jake's butt with cum.

Still gripping hands, the five of them remained in place for a few moments, relishing the post-coital calm.

It was then that Ryan, sprang back into action, "Well, I think I made you come, Coach."

"You surely did," Bruce confirmed. "Come here. We have to clean up."

And together, they cleaned up the mess that was left behind.

They exchanged hugs and there was chatter about future sexual escapades.

"So many fun things we can do together," Jake exclaimed. "Who knows? This might become a regular thing."

"It might," Cliff agreed, obviously anticipating the thrill. "I'm sure our experiences tonight just goes to show how much we all enjoy each other.

As the evening wound down, all five men exchanged tribbing stories about who had played in which holes, about how many guys each had fucked, about who had had their asses reamed the hardest, and so on.

All the men became more and more brazen, but they also became more confident and mature, realizing and accepting their bisexuality, pushing themselves beyond the boundaries they once considered epitomized masculinity. They understood now that there were no boundaries in consensually loving each other.

Ryan hugged Jake tightly as he bowed his back. Bruce's cock stayed within Ryan's intestines. Bruce slapped Jake's bare butt one final time. Ryan's penis twitched, seeping semen onto Bruce's abdomen.

"Well done, son!" Bruce exclaimed. "Now it's my turn."

Ryan maintained his position, allowing Bruce's penis to stay inside his bowels as Bruce began to release his sperm deep within him. Watching Bruce and Ryan attain their gay climax encouraged Kevin and Cliff to thrust into Jake more forcefully.

Due to the extra stimulation from being double-fucked, Jake could no longer prevent himself from climaxing, moaning as he smeared the couch cushions with a fresh splat of jizz. Cliff and Kevin were also near their breaking point, their dicks throbbing in sync.

"Sure you wanna fuck this hole?" Cliff inquired.

"Hell yeah!" Kevin confirmed.

Both men rammed their cocks deeper inside Jake a few more times before emptying their balls into his anus. Jake savored the feeling.

When they finally extracted their cocks from Jake's anus, Cliff wanted Jake to remain in position so he could better view his damaged, gaping hole. Cliff knew that this sight would please the future viewers.

"The sphincter is so broken! What a naughty little boy!" Cliff observed.

Jake strained to push the cum from his rectum, the camera capturing it sliding out past his balls and pooling beneath his scrotum.

"This is magnificent!" Cliff added, finally putting the camera aside.

Having completed the previous night's incredible gay sex reenactment, they all agreed to take a break. Jake removed his garter belt and stockings, and the five of them enjoyed a pleasant, casual meal together without any clothes on.

Following the meal, the men were content to just relax and stroke their penises as they watched Jake and Ryan engage in an intimate 69.

They spread some covers and pillows around the living room so that they could all sleep naked within the same room. Jake drifted off to sleep, pondering the number of kinky acts that the day could hold in store.

***

The next day, Jake awakened to the aroma of freshly brewed coffee and bacon. He observed that Ryan, Cliff, and Kevin were still sleeping. To prevent waking them, he got up quietly and wandered to the kitchen.

Jake encountered Bruce cooking in the kitchen, only half-clothed. Jake was fascinated by the sight of his coach's hairy bare butt, which the apron allowed to peek out.

"Good morning, pup."

"Good morning, coach!" Bruce smiled at Jake, pivoting to focus on his cooking. "How do you feel in the morning after the rough ride you gave your bottom yesterday? It seemed you enjoyed it."

"Feels wonderful." Jake replied, pouring himself a cup of coffee. "I wouldn't mind getting another good dicking today."

Bruce giggled at Jake's eagerness for more group gay sex, particularly more intense buttsex.

"I talked to your mother on the phone earlier." Bruce shared. "I told her how good you've been. She sounded a bit envious when I mentioned how receptive you've been to all our visitors. But she was nevertheless thrilled to hear how much interest you show in other men's cocks."

"I'm sure you should arrange a gangbang for her." Jake suggested cheekily.

"I was actually considering that." Bruce replied. "She may be interested after seeing how much you enjoy having so many large cocks in you."

Jake attempted to prevent the image of his mother engaging in a gangbang with a group of eager men from entering his mind. Just visualizing a bunch of naked men, however, was quite stimulating.

"Do you want some food?"

"Yes, please!" replied Jake. "I'll need to regenerate my energy for another day of sucking and being fucked."

Bruce served a portion on a plate for Jake and also brought him a fork. Jake was content to see scrambled eggs and crispy bacon.

"I hope you like bacon."

"I adore bacon!" Jake enthused. "Additionally, I wouldn't mind tasting your large member in my mouth."

"I know, Jake. Eat first, and we'll do other things later." Bruce reassured him. "Regarding your affection for cocks... Ryan indeed appears to appreciate it. He seemed to adore my dick. Perhaps you moved some long-repressed feelings in him when you got his ass blown out."

Jake took a bite of his eggs.

"Haven't pondered that before." Jake admitted. "And recalling the journey we had together with Ryan makes me even more eager."

Bruce chuckled again.

"I don't believe anybody on earth desires cock as much as you do." Bruce explained. "But the way Ryan used my dick indicated he's extremely biased toward males. Maybe you helped Ryan accept his true sexual proclivities."

Jake took another bite of his bacon.

"Wow, I hadn't considered that." Jake remarked, contemplating the magical night he'd shared with Ryan, when they'd made passionate love.

"You're not that different," Bruce stated. "Remember when you visited and I asked about your sexuality? You were timid, apprehensive, and uncertain. But then, you let loose sexually... anal... and you soon discovered you were a complete homosexual deep down. Not a hint of heterosexuality in your body."

"You're right, coach," Jake confessed. "Once I had the opportunity to play with your amazing penis, it confirmed what I'd always suspected about myself. Maybe Ryan needed the same experience."

Jake picked up a forkful of scrambled eggs, eaten in contemplation.

"It's fantastic to have a trustworthy friend you can engage sexually with," Bruce commented. "That's a connection you guys will always cherish."

Jake smiled and completed his breakfast. Bruce cleared the dishes for him while the other three men entered the kitchen.

"Did you two start fucking without us?" Cliff asked with a smirk.

"Not at all," Bruce responded. "I made some breakfast, and Jake and I were simply conversing. Are you hungry?"

They all agreed breakfast seemed appetizing. They sat down and Bruce served everyone a plate. The talk with his coach left Jake horny and yearning for something naughty. Luckily, he'd thought of a great plan.

Jake slipped into the living room and coated his ass in lube. He snatched a vibrator from the coffee table and attached a suction cup base. Hastily returning to the kitchen, Jake set the toy on the kitchen table to stand vertical. Climbing onto the vibrator, Jake settled onto it with ease.

Ryan, Cliff, and Kevin digested their breakfast while Jake masturbated on the table in front of them. The guys eating their meals hardly seemed affected by the somewhat erotic scene unfolding before them.

Jake fucked himself with the vibrator until he reached orgasm; the room filled with Jake's spurted jizz as it hit his stomach and the dinner table beneath him. He got off the vibrator and retook his seat.

"Jake's rear is presumably ready for more action," Kevin conjectured, amused. "Who wants to be the first to fuck him?"

They all concurred it was time to continue the group sexual escapades. The following hours were filled with vigorous homosexual intercourse: penetrations, blowjobs, and spent balls.

As the afternoon approached, the men prepared to leave. Jake, gratified by the uninhibited sex with four amazing men, was pleased that Cliff had another idea.

"I think Jake should get on his knees and let the rest of us cum on his face." Cliff proposed, eliciting laughter. "Is a gay orgy complete without the glorious bukkake finish?"

No one objected to this suggestion, and Jake eagerly changed into a cute pair of pink panties.

"I have an idea," Bruce proposed. "Jake should don a new pair of panties first. Then, he can touch himself while we cum on his face, but he must leave his penis inside its underwear. This ensures, if Jake has an orgasm, his underwear will be full of cum as well."

Their plan met no opposition. Jake paraded back to the bedroom, returning with a pair of frilly panties that accentuated his bulging erection.

Jake knelt down, eager for what was about to happen. The four naked others surrounded him, Cliff positioned strategically with a camera to capture the memorable fulfillment.

Jake couldn't contain his excitement. His weekend included uninhibited sex with four fantastic men, and now he was on his knees surrounded by cocks aimed for his face.

Bruce slapped Jake's cheek with his penis, prompting the others to do the same. Jake delighted by complimenting their actions - flicking each with his tongues.

"Is this what you've yearned for, Jake?" Bruce inquired. "To be on your knees, with so much dick to welcome the world to your faggotry?"

"There are no words to express how enthused I am." Jake replied. "I can't wait for all of you to paint my face with sperm!"

Cliff swiped some precum from Jake's cheeks, leaving a sticky strand. Jake chuckled, operating his tongue on Cliff's head before sharing an analogy with Ryan.

"You have a great dick inside your mouth," Jake told Ryan.

Ryan grinned, inviting his friend to partake. Jake obliged, tonguing Ryan briefly before he pulled back, smacking Jake's cheek with his erect penis.

"Jake's craving a cum shower," Kevin leaned in. "I think it's time to load him up."

Cliff captured the ensuing frenzy, his camera focusing on the group's grand finale.

"Jake," Bruce demanded, "confirm that your fantasies have come true: being at the mercy of a dick-loaded horde."

"This weekend has surpassed my wildest dreams," Jake crowned. "I can't wait for you guys to spunk all over my face!"

The four men intensely massaged their erections. Jake reached between his legs and began to push and rub on the bulge in his underwear. He closed his eyes, anticipating his forthcoming reward.

Kevin initiated, directing his penis towards Jake's face. A few more strokes brought him to orgasm, a substantial strand of cum shooting out and landing across Jake's face. A second, thinner strand followed, hitting him on the chin. He wiped the remaining drips across Jake's lips and then moved back so the other three could also share their semen.

The warm, sticky load only increased Jake's enthusiasm for rubbing himself further through the material of his underwear. He maintained his eyes closed, recognizing more jizz was headed his way.

Ryan and Cliff came close to simultaneously orgasming, their cum-filled additions covering Jake's face and slipping down his cheeks. With them finished, Bruce stepped closer.

Bruce informed Jake, "Just me left, buddy." He stroked himself for several inches.

Jake's three recent lovers' sperm on his face and sensing his coach about to add a fourth was sufficient to push Jake over the edge as he savorably created a sticky mess in his pink underwear.

Cliff zoomed in on Bruce using his hand on the back of Jake's head and holding his substantial cock very close to the child's eye. A powerful blast of semen spattered against Jake's eyelid. When Bruce slightly shifted, he released an equally generous discharge to the other eyelid. To conclude, Bruce tapped his penis on Jake's forehead until every last drop of sperm had been expelled.

"Check out this face!" Bruce exclaimed comically.

The boys provided Jake with some space now that they'd deposited on him. Cliff lowered the camera and got a good shot of the large damp spot in Jake's underwear.

"Well, Jake," Cliff begun. "...you've got four creamy loads dripping from your face. Would you say it was a successful weekend?"

Jake smiled and nodded his head.

"It was even more thrilling than my wildest masturbation fantasies. I had a lot of fantastic sex with four fantastic men, and now I'm enveloped in their semen!"

"You certainly are." Cliff replied. "That's a cute appearance for you."

"How did you feel about the sexual encounters leading up to this?" Cliff requested.

"It was amazing. The blowjobs were enjoyable. The anal sex was divine like always." Jake responded. "I even took pleasure in playing with various dildos and dongs."

"Real or artificial, you have a distinct predilection for penile objects." Cliff stated. "Speaking of the toys, I found it was sexy to see you and Ryan riding that double dildo together, one on top of the other, and both of you coming simultaneously."

"Yep, I can't wait to watch that and see how we looked sharing that toy together. It was hot in the instant but I want to view how it appeared with both our butts stuffed at the same time."

"From my standpoint, it was very erotic." Cliff shared with him. "And as for Ryan, you two truly seemed to possess tremendous fondness for one another. I believe you two make an adorable duo."

"I'm unsure whether he has any actual interest in being together." Jake mentioned. "But it's been entertaining having sex with him and sharing this weekend with him."

"I don't know. Ryan clearly had a lustful expression in his eyes whenever he was with you." Cliff added. "What would you claim was your preferred part of the gay orgy?"

"Sticking with the subject of Ryan, I was so happy for him for experiencing our coach's considerable cock up his pouch." Jake commented. "However, for me personally, my preferred highlight was obviously you and Kevin simultaneously penetrating my butt."

"That makes sense. And yes, that was your first time having two dicks simultaneously?"

"One and the same." Jake acknowledged. "However, I certainly hope this isn't the final time."

"I enjoyed your rectum appearing like a massive, gaping, semen-oozing hole after being reamed." Cliff declared. "It felt like I could view all the way into the vastness of your rectum."

Jake chuckled at the thought of Cliff and others witnessing his anus' interior after receiving a deep butt-fucking.

"I'm grateful your first gay orgy was a resounding achievement." Cliff stated. "Any final words for our viewers?"

Jake smiled and surveyed the camera through his semen-matted face.

"If you're watching this, I wish to thank you." Jake began. "I anticipate you boys enjoyed viewing me being fucked as much as I relished being fucked by all of these men this weekend. Remember to check out my OnlyFans for more of my amateur, gay content. Please feel free to send me messages detailing requested actions. Outside of that..."

Jake planted a cum-kiss on the camera lens.

"...stay hard, fellas! Who knows, maybe one day we can hook up in person and I could open up for you." he winked.

Jake smiled once more and waved goodbye. Cliff put down the camera.

Once the party was over, Jake took a brief shower to tidy up. He slipped into some clean pants and got ready for home. He thanked Kevin and Cliff immensely for taking the time to partake in their amazing sex-packed weekend. They all went their different ways, each returning to their respective residences.

Jake and Ryan resumed their place in the backseat, still holding hands the entire journey. Every now and then, the two would turn to each other for a deep, passionate kiss.

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