Chapter 14.2
John gave Lily's rear a few more thrusts before finally erupting and flooding her asshole with a fresh batch of warm spunk. Finished, he retracted himself from the anus.
Lily continued to grind on Steve's penis for several more minutes until they climaxed together, Steve's sticky cream coating the inner walls of Lily's cunt. Satisfied, Lily climbed off of his lap and stood next to her boyfriend.
"Thanks, guys." She said. "That was a great way to start the day."
"I'll happily fuck that sweet pussy anytime." Steve told her.
John and Lily headed to the bathroom to get cleaned up and shower. As Lily started the shower water, John took a seat on the toilet.
"Sometimes I get so jealous of you." John said.
"Why? Because I was fucking your dad?"
"No." John added with a laugh. "It's so easy for girls to get fucked by multiple guys at the same time. I wish I could have two guys fuck me at one time."
"Like in your butt?" Lily asked. "You could totally do that, babe."
"I don't know. I think I'm too tight to fit a second one in there."
"Don't be silly." Lily said. "Remember when you didn't think you could take all eleven inches of that black dick?"
"I do."
"But you kept at it. You persevered." Lily told him. "And eventually every single inch of that gigantic penis was inside of you. And now it's one of your favorite memories."
"That's true." John admitted.
"If it's your dream to have two dicks inside your ass at the same time, I say we make that happen." Lily added. "I will help you make that a reality. And I'm confident you'll be able to fit two or maybe even more cocks into your sweet little hole, babe."
"Okay. Thanks, dear." John said.
"Now. Should we shower?" Lily asked. "Or do you want to be a good boy and eat my creampies first?"
"Creampies please."
Lily turned her back to her boyfriend and held her ass cheeks open. John leaned in and began to lick, suck, and clean his girlfriend's dirty, soiled fuckholes.
Later that afternoon, John and Lily were the first guests to arrive at Khloe's house. Lily was looking ravishing in a black one-piece swimsuit with a thong back, allowing her buns to sway freely.
Lily introduced John and Khloe to each other. Khloe was absolutely beautiful. Dark, shoulder-length hair. Brilliant eyes and smile. Ample breasts and a superb ass.
Khloe was wearing a white bikini top and matching bottom. Despite her also wearing cutoff denim shorts, the shorts being unzipped and open allowed for onlookers to confirm the matching white bottom piece.
John had on a rainbow-colored bikini and a white tanktop.
They were in the kitchen, watching Khloe mix up some frozen margaritas. Any time she turned her back, John tried to catch a glimpse of her backside. To be fair, Lily was also checking out Khloe's body.
"So you just sucked him off right there in the bathroom?" Khloe asked.
"That's correct." John confirmed. "And I got so turned on by the whole thing that I came in my panties."
"Sounds hot!" Khloe said.
"I imagine he's going to want to have sex at some point when he's here." John told her. "I hope that won't cause any problems."
"Lily has told me plenty about you, John." Khloe said with a wink. "You guys are more than welcome to fuck anywhere you like. Hopefully you won't be the only one getting laid this afternoon. Judging by how much ass Lily is flaunting in her swimsuit, I'm thinking there might be some serious sex happening."
"If you've got it, flaunt it, right?" Lily asked.
"Absolutely!" Khloe agreed. "I don't mind. Sun's out, buns out, girl."
"John's showing some ass too."
"You're not wrong." Khloe said. "That bikini looks really nice on him. I might have to give your boyfriend a rimjob!"
"I promise you he would enjoy it." Lily told her. "We should probably wait for Tommy and Dylan to get here before we start sucking each other's ass though."
"Fair enough." Khloe added. "The drinks are ready. Who wants margaritas?"
Khloe poured each of them a glass of frozen margarita. Once again John admired Khloe's round buttocks in her denim shorts. When they each had their glass, they lifted them up and clanked them together.
"Here's to good friends." Khloe said.
"And great sex with those friends!" Lily added.
They each took a sip of their drink. Lily reached out and playfully squeezed John's bulge through his bikini.
"Careful." John warned. "If I get hard, I'm liable to bend you over, pull that thong out of your crack, and fuck that sexy butt."
"That's fine. You'll be getting bent over soon enough by Dylan, babe."
"Hopefully." John added.
Dylan and Tommy arrived shortly thereafter. Tommy was sporting typical black swim shorts while Dylan walked in wearing a very cheeky black speedo. As he walked past the others, John couldn't help but comment on his muscular buttocks.
"What an incredible ass!" John exclaimed. "How did I not notice that thing last night?"
"You were too busy stuffing your face with my cock." Dylan quipped.
"That's valid."
They all got their drinks and headed out to the pool. Dylan and Tommy got in the pool while Khloe and Lily set out some towels. John chose to remain next to his girlfriend for the time being.
"Have you gone back to The Club since you got accepted?" Lily asked.
"Not yet, but hopefully soon." Khloe answered. "I'm just kind of nervous, you know?"
"No reason to be nervous." Lily told her. "No one will judge you."
"Yeah and with a body like that, there will be tons of guys that want to have sex with you." John added. "Myself included."
"Well thank you." Khloe said, blushing. "That's sweet."
Khloe took another sip from her beverage. John took off his tanktop and set it aside. With the alcohol loosening everyone up, he was getting excited at the naughty thoughts running through his mind.
"Why don't you ask Dylan to rub some sunscreen on you, babe?" Lily suggested.
"Not a bad idea."
John got up and walked over to the pool to talk to Dylan and ask for his assistance.
"If they're wanting to have sex, I should go grab some lube." Khloe said, also getting up and heading inside.
Dylan and Tommy climbed out of the pool, rejoining Lily along with John. John got on his stomach next to Lily and handed Dylan the sunscreen. Dylan got behind John and straddled him from behind, the bulge in his speedo resting directly on John's buns.
"Thanks for helping my boyfriend." Lily said.
"My pleasure." Dylan replied.
Dylan squirted some sunscreen onto John's shoulders and then began to spread it over his back. About that time, Khloe returned, setting a bottle of lube on the ground next to John.
"There's some lube for when you guys decide it's time to fuck." Khloe told them.
Dylan methodically continued to work the sunscreen into John's back, moreso massaging his back rather than rubbing the lotion into it.
"That feels really good dude." John said.
"Yeah?" Dylan asked. "It's going to feel even better when I drive my hard cock deep into your hungry little asshole."
As he rubbed the lotion in, Dylan put more weight on his pelvic area, forcing the expanding bulge in his speedo deeper against the crack of John's ass.
"Quite the tent you're pitching, Tommy." Lily said with a snicker.
"What do you expect?" Tommy asked. "My best friend and this cute dude are rubbing on each other and talking about dicks in butts."
"I was just teasing you." Lily added. "I'm pretty wet myself. What about you, Khloe?"
"I'm starting to get a little aroused, too."
"Do you want Tommy to take off his swimsuit?" Lily asked.
"That might be cool." Khloe said sheepishly.
"Come on, Tommy." Lily suggested. "Show Khloe your dick!"
Tommy pushed his swim trunks down, revealing his erect penis to the group. Khloe smiled when she got a look at the hard flesh.
"Touch it!" Lily instructed her friend.
Khloe reached out and took Tommy's dick in her hand, examining its hardness. She cupped his balls and even extended a finger to graze across his anus.
"Cute penis!" Khloe told him.
Lily took it upon herself to get up onto her knees next to Khloe. She then looked at Tommy in a way that he instinctively moved closer to the girls, his cock waving in front of their faces. Lily kissed the tip of Tommy's penis and Khloe followed suit. It wasn't long before the two girls were happily sharing and taking turns giving Tommy a blowjob.
"That's so cool." Dylan remarked. "Your girlfriend is blowing your best friend and you're about to get buttfucked yourself!"
Lily and Khloe continued to orally service Tommy. Lily allowed Khloe to be more and more involved, until she naturally backed off so that it was just Khloe sucking Tommy's dick.
"Mmm yeah. Suck that cock, girl!" Lily told her friend.
And suck it she did. Khloe even moved her hands onto Tommy's ass, pulling him toward her so he could fuck her face even faster. Lily took the opportunity to remove her swimsuit, joining Tommy in being naked.
"I know I said I'm mostly into fucking other guys." Dylan said. "But you have a really beautiful twat."
"Glad you like it." Lily replied, parting her legs to make sure he had a better view.
Tommy was breathing harder as Khloe vigorously sucked him into her mouth. He held the back of her head, pumping her face with his cock.
"Oh fuck, I'm cumming!" Tommy announced, emptying the contents of his testicles into Khloe's mouth.
Khloe kept her lips sealed around Tommy's twitching penis until all of his semen had been released and subsequently swallowed.
"Nice job, you two." Lily said. "But now Tommy and I are the only ones that are naked. I think that needs to change."
Dylan climbed off of John and stood up, happily pulling down his speedo and freeing his erection.
Khloe also stood up and turned her back to the group, removing her bikini top. She dropped her shorts, giving everyone a wonderful view of her ass in her white bikini.
"I have a riddle for you guys." Khloe said. "What's better than three hard cocks?"
"What?"
Khloe pushed her bikini bottom down and turned back to face them.
"A fourth one!"
John's jaw dropped as she turned around, revealing the fact that she was packing a beautiful penis. Khloe gave everyone a few moments to take in this surprise.
"I'm trans." She said. "I hope that's not a turn off."
"Are you kidding me?" John asked. "You look fantastic, and your cock looks delicious."
"See?" Lily added. "I told you they'd be cool with you being transgender."
Khloe blushed as everyone continued to look at her dick. "Thanks. I just get nervous sometimes about being judged."
"Guess it's my turn to get naked." John told them. "I've been hard from feeling Dylan's boner against my ass this whole time."
"Before you take off your bikini, I think you should tell everyone what we talked about this morning, babe." Lily suggested.
"What do you mean?" John asked as he stood up, the bulge in his bikini obvious to the onlookers.
"That thing you said you wanted to do."
"Really?" John asked.
"Hell yeah, babe." Lily added. "Khloe was nervous about showing you guys her dick, but that went well. Just tell them."
John took a deep breath as he pulled down his rainbow bikini, his penis now exposed along with the others.
"Well, as I'm sure you're all aware, I've been fucked in the ass countless times over the last few years." John explained. "And I've had a blast, no pun intended. But lately I've really wanted to try taking the next step. I don't know if I'd actually be able to do it, or handle it, but I really want to try getting fucked by two cocks at once."
"There's nothing wrong or weird about that." Khloe said.
"I agree." Dylan added. "Let's do it!"
"What? Right now?" John asked in disbelief.
"Sure." Dylan answered. "There's plenty of dicks here to accomplish your dream. I say we help you live out your fantasy right here, right now. Khloe, will you help me blow out John's asshole?"
"I'd be happy to help!" Khloe said.
"This is so exciting!" Lily exclaimed. "Babe, you're finally about to experience two cocks working together inside of your butthole."
John's head was spinning, and his cock was twitching, with excitement. He couldn't believe he was about to get to try his coveted activity.
"We need to get those dicks lubed up and also John's rear." Lily said, taking command of the project. "Dylan, if you'll prep my boyfriend, I'll take care of your manpipe. Deal?"
"Deal."
Khloe squirted some lube into her hand and began to get her penis nice and slick. Lily also got some lube to prep Dylan's cock. Dylan applied a healthy dollop to John's crack as John spread himself and held his buns apart.
"Look at that hole." Dylan commented. "A hairless, smooth man cunt. My favorite."
"Lily helped me shave it yesterday."
Dylan rubbed the lubricant around and into John's backdoor. Lily continued to lube Dylan's shaft while Khloe took care of herself.
"Okay. I think Khloe should get on the towel so John can sit on her lap in a cowgirl position." Lily suggested. "And then Dylan can be behind him and come from that angle when he's ready."
No one argued with her suggestion and they began to get into place. John straddled Khloe and held her shaft, guiding it between his cheeks. His anus offered little resistance as he eased himself down onto cock. Khloe smiled at him as his anus gripped her erection.
"Feel free to hold onto my tits if you need to." She offered.
"Thanks."
With John safely impaled on Khloe's lap, Dylan knelt down behind him. John leaned forward slightly, aiming to give Dylan a better target. Dylan moved his hips forward, holding the tip of his cock against John's already-stuffed hole.
"Are you ready?" Dylan asked.
"No clue." John replied. "But there's only one way to find out."
John lifted himself up Khloe's shaft slightly as Dylan began to push himself between John's sphincter and Khloe's penis. It took a few moments of careful, dedicated maneuvering, but John gasped when he felt Dylan's dickhead successfully pop inside.
"I'm in." Dylan said.
"Yes." John muttered. "Yes you are."
"I need a picture of this. Or some video." Lily said, finding her cell phone. "I can't wait until your parents see this."
Dylan held steady, letting John's rectum get comfortable with having a second phallic probe in his rear. Lily made sure to get some closeups of her boyfriend's initial voyage into double anal penetration.
"This looks so sexy." Lily told him.
Dylan very delicately began to insert more of his penis, further stretching open John's backdoor. John took Khloe up on her offer, holding onto her breasts as he tried to relax and permit entry to both dicks.
"Just relax and let it happen." Khloe suggested with a calming smile. "Allow your dreams to come true."
John squeezed Khloe's tits as more of Dylan's cock slid between his rectal wall and Khloe's shaft.
"I'm just about all the way in." Dylan announced.
"Take it, babe." Lily encouraged. "Take those cocks. I believe in you and I know you can do this."
John took a deep breath as Dylan added the rest of his penis to the party inside John's asshole. Lily giggled seeing both erections fully inserted into her boyfriend. John was pleasantly surprised at how quickly his rectum was adjusting to his first double penetration.
Dylan and Khloe began to slowly work their erections back and forth inside of John, alternating their strokes. As Khloe's shecock slid out, Dylan's was sliding in, and vice versa. This made for a harmonious seesaw of buttsex between the two slabs of meat.
"That looks really cool." Tommy said.
"I'm impressed by how stretched out his butthole is." Lily commented. "My pussy is soaking wet right now."
John gave Khloe's tits another firm squeeze as the two cocks continued with their mission. Lily got on all fours next to John, but positioned herself so that she had a perfect view of his anal devastation.
"Come fuck me from behind, Tommy." Lily demanded. "I need a dick in my twat."
Tommy obeyed, getting on his knees behind Lily, grabbing her hips, and easily inserting his penis into her moist vagina. He began to fuck her hungry clam as they both watched the anal assault continue on her boyfriend.
Khloe and Dylan had found an amazing rhythm of making love to John's rectum. In, out. In, out. John was moaning with pleasure as they thrusted into his manhole.
"Those dicks feel incredible!" John exclaimed. "Don't stop fucking my ass."
John looked into Khloe's eyes as her penis continued to swiftly fuck his ass alongside Dylan's prick.
Lily reached between her legs to play with her clit as Tommy fucked her, both of them still focused on watching John's double-barrel assblasting.
John's throbbing erection was bobbing and swaying in the air as he rode the two incredible specimens.
"You look so hot right now, babe." Lily said. "Taking both of those thick dongs right up your horny ass."
"Thanks honey." John told her. "This is amazing."
The cocks continued to blow open John's backdoor. The combination of being fucked, rubbing her clit, and watching her boyfriend receive passionate gay sex overwhelmed Lily. She squealed in delight, orgasming and squirting her pussy juice onto her towel beneath her.
Tommy pulled his cock out of Lily's snatch, jerking his shaft and spraying her asscrack with several generous ropes of sticky cum.
"Thanks, Tommy." Lily said. "That was exactly what my cunt was needing."
"Happy to help." Tommy replied.
"My turn." Khloe whispered, winking at John.
The first domino had fallen, and the friction between John's rectum and Dylan's rigid manhood left Khloe in ecstacy. She moaned as she enjoyed her release, pumping her sweet semen deep into John's bowels. As John felt her cum inside him, his own penis twitched, shooting a forceful spray of jizz that landed over Khloe's breasts.
Dylan smacked John's ass cheek as he forced his cock inside and contributed to the pool of sperm Khloe had started. Dylan arched his back as he ejaculated into the loose hole.
"Fuck yes." Lily said as she watched. "Fill that tight ass with cum."
"I don't think it's very tight at the moment." Dylan joked.
Lily giggled as Dylan pulled out of the ruined hole. Khloe gently guided John off of her penis. John lowered himself onto his towel, on his stomach, exhausted from the buttfucking. Lily took the opportunity to get another picture on her phone: a close up of John's red, gaping, semen-filled fuckhole. In his loosened condition, he couldn't help but let the cum ooze out and down his scrotum, and then over his testicles.
"Your asshole looks so sexy right now, babe." Lily told him. "I'm so happy that you got to experience your dream of being fucked by two cocks at once."
"That was intense and incredible." John muttered, still exhausted. "Thank you both so much."
"I promised you my dick in your ass." Dylan told him. "I don't joke around about sex."
"Happy to help you with your dirty little fantasy." Khloe added. "I enjoyed fucking you."
Lily reached over and scooped a blob of the cum mixture from her boyfriend's anus, then brought her finger to his face so that John could have a taste.
"Delicious." John told her.
Lily scooped another blob so that she could also have a taste.
"Yummy!" She agreed.
After a few more moments, Khloe offered to refill everyone's margaritas. Tommy went with her to help, leaving Dylan with John and Lily.
"Thanks for sharing your boyfriend with me." Dylan said.
"Anytime!" Lily promptly replied.
"I've heard you guys mention some club a few times. What is it? Like a gay club?" Dylan asked.
Lily snickered.
"It's basically a members-only sex club." Lily answered. "A lot of members are families. All kinds of sex happens there, but yes, gay sex is also frequent. That's where John took those eleven inches of penis. Right in front of a crowd of people, men and women, cheering him on. His mom even held his hand while he was getting assfucked. It was awesome."
"Sounds like my kind of place." Dylan said. "Any chance I could join?"
"I can't guarantee anything." Lily told him. "But my mom runs it. I can definitely ask her about it and let you know."
"That's cool." Dylan added. "No hard feelings if it doesn't work out. It just sounds like a good place to go and... unload... ya know?"
"I totally get it. And there are plenty of guys, or girls, who would help you unload those balls." Lily said.
"I don't mind fucking a sexy girl occasionally."
"Maybe you can fuck me?" Lily suggested. "My boyfriend got to feel you in his ass. I feel like I should too."
"I would be happy to fuck you in the ass." Dylan told her. "Maybe your boyfriend could get me hard again?"
"Sounds like a plan to me!" Lily exclaimed. "Can you suck Dylan's penis, babe? So he can fuck me in the butt?"
John rolled over and mustered up the energy to get onto his knees. Dylan took a few steps forward so that his soft dick was dangling directly in front of John's face.
"Okay, babe." Lily instructed. "Put the penis in your mouth just like you did back at the gay bar last night."
John opened up and easily but gently sucked the entire soft shaft into his mouth. As he suckled Dylan's genitals, he also fondled his testicles.
"Good boy." Dylan encouraged.
Lily started to prep her backdoor with some lube as she watched John sucking the cock of their new friend. John's dick also started to get aroused again as he sucked the love stick. Especially since he could taste his own ass flavor on Dylan's member.
It didn't take long for Dylan's penis to expand and stiffen in John's mouth. Dylan gently guided John off of his erection.
"Why don't you hold Lily's cheeks open for me?" Dylan suggested.
Lily got on all fours and John got beside her, holding her buns apart. This gave Dylan a clear line of sight to his puckered target, and he easily inserted his penis into the depths of Lily's rectum.
"Mmm that's nice and tight." Dylan said, winking at John. "Way tighter than your boyfriend's ass is currently."
Lily giggled as her anus was being penetrated. "Makes sense. I just have one dick in my ass instead of two like my wonderful whore of a boyfriend."
John continued to hold his girlfriend's butt cheeks as Dylan fucked her. He watched as the penis slid in and out of her rear, the sight causing his own dick to throb with lust.
"Doesn't he have a nice cock?" John asked.
"It's great, babe." Lily agreed. "I can see why you creamed yourself just from sucking on it."
"You two are too sweet." Dylan told them. "It's just a penis."
"But you could've shared it with anyone you wanted." John explained. "We really appreciate you letting us play with it and experience its glory."
Dylan continued to thrust his shaft in and out of Lily's welcoming asshole.
"I'm going to need to hop in the pool after this." Dylan said. "All this fucking has made me really sweaty."
John let go of Lily's buttocks and made his way behind Dylan. He delicately took a muscular cheek in each hand and parted them, admiring the glistening backside.
"Mind if I have a taste of your ass?" John asked.
"Be my guest." Dylan replied as he continued to fuck Lily.
John leaned his face closer to Dylan's exposed bottom. He couldn't resist the urge to inhale his musky aroma first. John then stuck out his tongue, softly swiping at the moist orifice. He then pursed his lips and planted a kiss on the wet hole.
"Tasty!" John noted.
John went a bit lower, extending his tongue and touching it to Dylan's taint. Slowly, he moved up, licking the length of Dylan's salty, sweaty asscrack all the way to the tip. John grabbed his shaft and gave it a few quick tugs, ejaculating onto the grass below.
"Did you just cum from licking my ass?"
"I sure did." John answered, shaking the last few sticky drops from his penis. "You've got a great flavor back there."
"Guess that means it's my turn."
Dylan sunk his cock as deep into Lily's asshole as he could, erupting in orgasm. Semen coated the inside of Lily's rectum.
Khloe and Tommy returned with fresh margaritas just as Dylan was sliding out of Lily's dripping anus.
"What took you two so long?" Lily asked.
"Tommy wanted to get a closer look at my cock." Khloe said with a giggle. "But he wouldn't stop playing with it until he got to see me shoot a load of cum."
"That sounds like Tommy!" Lily told her.
"Can you blame me?" Tommy asked. "It's not every day you meet a beautiful girl with such a pretty cock to match."
"I'm just giving you a hard time." Lily said.
"Thankfully Khloe gave me a hard time, too." Tommy joked.
The group took a short break, enjoying their margaritas. They also took a quick dip in the pool, swimming together in the nude and cooling off, before further indulging in more sexual debauchery.
Lily continued to grind on Steve's penis for several more minutes until they climaxed together, Steve's sticky cream coating the inner walls of Lily's cunt. Satisfied, Lily climbed off of his lap and stood next to her boyfriend.
"Thanks, guys." She said. "That was a great way to start the day."
"I'll happily fuck that sweet pussy anytime." Steve told her.
John and Lily headed to the bathroom to get cleaned up and shower. As Lily started the shower water, John took a seat on the toilet.
"Sometimes I get so jealous of you." John said.
"Why? Because I was fucking your dad?"
"No." John added with a laugh. "It's so easy for girls to get fucked by multiple guys at the same time. I wish I could have two guys fuck me at one time."
"Like in your butt?" Lily asked. "You could totally do that, babe."
"I don't know. I think I'm too tight to fit a second one in there."
"Don't be silly." Lily said. "Remember when you didn't think you could take all eleven inches of that black dick?"
"I do."
"But you kept at it. You persevered." Lily told him. "And eventually every single inch of that gigantic penis was inside of you. And now it's one of your favorite memories."
"That's true." John admitted.
"If it's your dream to have two dicks inside your ass at the same time, I say we make that happen." Lily added. "I will help you make that a reality. And I'm confident you'll be able to fit two or maybe even more cocks into your sweet little hole, babe."
"Okay. Thanks, dear." John said.
"Now. Should we shower?" Lily asked. "Or do you want to be a good boy and eat my creampies first?"
"Creampies please."
Lily turned her back to her boyfriend and held her ass cheeks open. John leaned in and began to lick, suck, and clean his girlfriend's dirty, soiled fuckholes.
Later that afternoon, John and Lily were the first guests to arrive at Khloe's house. Lily was looking ravishing in a black one-piece swimsuit with a thong back, allowing her buns to sway freely.
Lily introduced John and Khloe to each other. Khloe was absolutely beautiful. Dark, shoulder-length hair. Brilliant eyes and smile. Ample breasts and a superb ass.
Khloe was wearing a white bikini top and matching bottom. Despite her also wearing cutoff denim shorts, the shorts being unzipped and open allowed for onlookers to confirm the matching white bottom piece.
John had on a rainbow-colored bikini and a white tanktop.
They were in the kitchen, watching Khloe mix up some frozen margaritas. Any time she turned her back, John tried to catch a glimpse of her backside. To be fair, Lily was also checking out Khloe's body.
"So you just sucked him off right there in the bathroom?" Khloe asked.
"That's correct." John confirmed. "And I got so turned on by the whole thing that I came in my panties."
"Sounds hot!" Khloe said.
"I imagine he's going to want to have sex at some point when he's here." John told her. "I hope that won't cause any problems."
"Lily has told me plenty about you, John." Khloe said with a wink. "You guys are more than welcome to fuck anywhere you like. Hopefully you won't be the only one getting laid this afternoon. Judging by how much ass Lily is flaunting in her swimsuit, I'm thinking there might be some serious sex happening."
"If you've got it, flaunt it, right?" Lily asked.
"Absolutely!" Khloe agreed. "I don't mind. Sun's out, buns out, girl."
"John's showing some ass too."
"You're not wrong." Khloe said. "That bikini looks really nice on him. I might have to give your boyfriend a rimjob!"
"I promise you he would enjoy it." Lily told her. "We should probably wait for Tommy and Dylan to get here before we start sucking each other's ass though."
"Fair enough." Khloe added. "The drinks are ready. Who wants margaritas?"
Khloe poured each of them a glass of frozen margarita. Once again John admired Khloe's round buttocks in her denim shorts. When they each had their glass, they lifted them up and clanked them together.
"Here's to good friends." Khloe said.
"And great sex with those friends!" Lily added.
They each took a sip of their drink. Lily reached out and playfully squeezed John's bulge through his bikini.
"Careful." John warned. "If I get hard, I'm liable to bend you over, pull that thong out of your crack, and fuck that sexy butt."
"That's fine. You'll be getting bent over soon enough by Dylan, babe."
"Hopefully." John added.
Dylan and Tommy arrived shortly thereafter. Tommy was sporting typical black swim shorts while Dylan walked in wearing a very cheeky black speedo. As he walked past the others, John couldn't help but comment on his muscular buttocks.
"What an incredible ass!" John exclaimed. "How did I not notice that thing last night?"
"You were too busy stuffing your face with my cock." Dylan quipped.
"That's valid."
They all got their drinks and headed out to the pool. Dylan and Tommy got in the pool while Khloe and Lily set out some towels. John chose to remain next to his girlfriend for the time being.
"Have you gone back to The Club since you got accepted?" Lily asked.
"Not yet, but hopefully soon." Khloe answered. "I'm just kind of nervous, you know?"
"No reason to be nervous." Lily told her. "No one will judge you."
"Yeah and with a body like that, there will be tons of guys that want to have sex with you." John added. "Myself included."
"Well thank you." Khloe said, blushing. "That's sweet."
Khloe took another sip from her beverage. John took off his tanktop and set it aside. With the alcohol loosening everyone up, he was getting excited at the naughty thoughts running through his mind.
"Why don't you ask Dylan to rub some sunscreen on you, babe?" Lily suggested.
"Not a bad idea."
John got up and walked over to the pool to talk to Dylan and ask for his assistance.
"If they're wanting to have sex, I should go grab some lube." Khloe said, also getting up and heading inside.
Dylan and Tommy climbed out of the pool, rejoining Lily along with John. John got on his stomach next to Lily and handed Dylan the sunscreen. Dylan got behind John and straddled him from behind, the bulge in his speedo resting directly on John's buns.
"Thanks for helping my boyfriend." Lily said.
"My pleasure." Dylan replied.
Dylan squirted some sunscreen onto John's shoulders and then began to spread it over his back. About that time, Khloe returned, setting a bottle of lube on the ground next to John.
"There's some lube for when you guys decide it's time to fuck." Khloe told them.
Dylan methodically continued to work the sunscreen into John's back, moreso massaging his back rather than rubbing the lotion into it.
"That feels really good dude." John said.
"Yeah?" Dylan asked. "It's going to feel even better when I drive my hard cock deep into your hungry little asshole."
As he rubbed the lotion in, Dylan put more weight on his pelvic area, forcing the expanding bulge in his speedo deeper against the crack of John's ass.
"Quite the tent you're pitching, Tommy." Lily said with a snicker.
"What do you expect?" Tommy asked. "My best friend and this cute dude are rubbing on each other and talking about dicks in butts."
"I was just teasing you." Lily added. "I'm pretty wet myself. What about you, Khloe?"
"I'm starting to get a little aroused, too."
"Do you want Tommy to take off his swimsuit?" Lily asked.
"That might be cool." Khloe said sheepishly.
"Come on, Tommy." Lily suggested. "Show Khloe your dick!"
Tommy pushed his swim trunks down, revealing his erect penis to the group. Khloe smiled when she got a look at the hard flesh.
"Touch it!" Lily instructed her friend.
Khloe reached out and took Tommy's dick in her hand, examining its hardness. She cupped his balls and even extended a finger to graze across his anus.
"Cute penis!" Khloe told him.
Lily took it upon herself to get up onto her knees next to Khloe. She then looked at Tommy in a way that he instinctively moved closer to the girls, his cock waving in front of their faces. Lily kissed the tip of Tommy's penis and Khloe followed suit. It wasn't long before the two girls were happily sharing and taking turns giving Tommy a blowjob.
"That's so cool." Dylan remarked. "Your girlfriend is blowing your best friend and you're about to get buttfucked yourself!"
Lily and Khloe continued to orally service Tommy. Lily allowed Khloe to be more and more involved, until she naturally backed off so that it was just Khloe sucking Tommy's dick.
"Mmm yeah. Suck that cock, girl!" Lily told her friend.
And suck it she did. Khloe even moved her hands onto Tommy's ass, pulling him toward her so he could fuck her face even faster. Lily took the opportunity to remove her swimsuit, joining Tommy in being naked.
"I know I said I'm mostly into fucking other guys." Dylan said. "But you have a really beautiful twat."
"Glad you like it." Lily replied, parting her legs to make sure he had a better view.
Tommy was breathing harder as Khloe vigorously sucked him into her mouth. He held the back of her head, pumping her face with his cock.
"Oh fuck, I'm cumming!" Tommy announced, emptying the contents of his testicles into Khloe's mouth.
Khloe kept her lips sealed around Tommy's twitching penis until all of his semen had been released and subsequently swallowed.
"Nice job, you two." Lily said. "But now Tommy and I are the only ones that are naked. I think that needs to change."
Dylan climbed off of John and stood up, happily pulling down his speedo and freeing his erection.
Khloe also stood up and turned her back to the group, removing her bikini top. She dropped her shorts, giving everyone a wonderful view of her ass in her white bikini.
"I have a riddle for you guys." Khloe said. "What's better than three hard cocks?"
"What?"
Khloe pushed her bikini bottom down and turned back to face them.
"A fourth one!"
John's jaw dropped as she turned around, revealing the fact that she was packing a beautiful penis. Khloe gave everyone a few moments to take in this surprise.
"I'm trans." She said. "I hope that's not a turn off."
"Are you kidding me?" John asked. "You look fantastic, and your cock looks delicious."
"See?" Lily added. "I told you they'd be cool with you being transgender."
Khloe blushed as everyone continued to look at her dick. "Thanks. I just get nervous sometimes about being judged."
"Guess it's my turn to get naked." John told them. "I've been hard from feeling Dylan's boner against my ass this whole time."
"Before you take off your bikini, I think you should tell everyone what we talked about this morning, babe." Lily suggested.
"What do you mean?" John asked as he stood up, the bulge in his bikini obvious to the onlookers.
"That thing you said you wanted to do."
"Really?" John asked.
"Hell yeah, babe." Lily added. "Khloe was nervous about showing you guys her dick, but that went well. Just tell them."
John took a deep breath as he pulled down his rainbow bikini, his penis now exposed along with the others.
"Well, as I'm sure you're all aware, I've been fucked in the ass countless times over the last few years." John explained. "And I've had a blast, no pun intended. But lately I've really wanted to try taking the next step. I don't know if I'd actually be able to do it, or handle it, but I really want to try getting fucked by two cocks at once."
"There's nothing wrong or weird about that." Khloe said.
"I agree." Dylan added. "Let's do it!"
"What? Right now?" John asked in disbelief.
"Sure." Dylan answered. "There's plenty of dicks here to accomplish your dream. I say we help you live out your fantasy right here, right now. Khloe, will you help me blow out John's asshole?"
"I'd be happy to help!" Khloe said.
"This is so exciting!" Lily exclaimed. "Babe, you're finally about to experience two cocks working together inside of your butthole."
John's head was spinning, and his cock was twitching, with excitement. He couldn't believe he was about to get to try his coveted activity.
"We need to get those dicks lubed up and also John's rear." Lily said, taking command of the project. "Dylan, if you'll prep my boyfriend, I'll take care of your manpipe. Deal?"
"Deal."
Khloe squirted some lube into her hand and began to get her penis nice and slick. Lily also got some lube to prep Dylan's cock. Dylan applied a healthy dollop to John's crack as John spread himself and held his buns apart.
"Look at that hole." Dylan commented. "A hairless, smooth man cunt. My favorite."
"Lily helped me shave it yesterday."
Dylan rubbed the lubricant around and into John's backdoor. Lily continued to lube Dylan's shaft while Khloe took care of herself.
"Okay. I think Khloe should get on the towel so John can sit on her lap in a cowgirl position." Lily suggested. "And then Dylan can be behind him and come from that angle when he's ready."
No one argued with her suggestion and they began to get into place. John straddled Khloe and held her shaft, guiding it between his cheeks. His anus offered little resistance as he eased himself down onto cock. Khloe smiled at him as his anus gripped her erection.
"Feel free to hold onto my tits if you need to." She offered.
"Thanks."
With John safely impaled on Khloe's lap, Dylan knelt down behind him. John leaned forward slightly, aiming to give Dylan a better target. Dylan moved his hips forward, holding the tip of his cock against John's already-stuffed hole.
"Are you ready?" Dylan asked.
"No clue." John replied. "But there's only one way to find out."
John lifted himself up Khloe's shaft slightly as Dylan began to push himself between John's sphincter and Khloe's penis. It took a few moments of careful, dedicated maneuvering, but John gasped when he felt Dylan's dickhead successfully pop inside.
"I'm in." Dylan said.
"Yes." John muttered. "Yes you are."
"I need a picture of this. Or some video." Lily said, finding her cell phone. "I can't wait until your parents see this."
Dylan held steady, letting John's rectum get comfortable with having a second phallic probe in his rear. Lily made sure to get some closeups of her boyfriend's initial voyage into double anal penetration.
"This looks so sexy." Lily told him.
Dylan very delicately began to insert more of his penis, further stretching open John's backdoor. John took Khloe up on her offer, holding onto her breasts as he tried to relax and permit entry to both dicks.
"Just relax and let it happen." Khloe suggested with a calming smile. "Allow your dreams to come true."
John squeezed Khloe's tits as more of Dylan's cock slid between his rectal wall and Khloe's shaft.
"I'm just about all the way in." Dylan announced.
"Take it, babe." Lily encouraged. "Take those cocks. I believe in you and I know you can do this."
John took a deep breath as Dylan added the rest of his penis to the party inside John's asshole. Lily giggled seeing both erections fully inserted into her boyfriend. John was pleasantly surprised at how quickly his rectum was adjusting to his first double penetration.
Dylan and Khloe began to slowly work their erections back and forth inside of John, alternating their strokes. As Khloe's shecock slid out, Dylan's was sliding in, and vice versa. This made for a harmonious seesaw of buttsex between the two slabs of meat.
"That looks really cool." Tommy said.
"I'm impressed by how stretched out his butthole is." Lily commented. "My pussy is soaking wet right now."
John gave Khloe's tits another firm squeeze as the two cocks continued with their mission. Lily got on all fours next to John, but positioned herself so that she had a perfect view of his anal devastation.
"Come fuck me from behind, Tommy." Lily demanded. "I need a dick in my twat."
Tommy obeyed, getting on his knees behind Lily, grabbing her hips, and easily inserting his penis into her moist vagina. He began to fuck her hungry clam as they both watched the anal assault continue on her boyfriend.
Khloe and Dylan had found an amazing rhythm of making love to John's rectum. In, out. In, out. John was moaning with pleasure as they thrusted into his manhole.
"Those dicks feel incredible!" John exclaimed. "Don't stop fucking my ass."
John looked into Khloe's eyes as her penis continued to swiftly fuck his ass alongside Dylan's prick.
Lily reached between her legs to play with her clit as Tommy fucked her, both of them still focused on watching John's double-barrel assblasting.
John's throbbing erection was bobbing and swaying in the air as he rode the two incredible specimens.
"You look so hot right now, babe." Lily said. "Taking both of those thick dongs right up your horny ass."
"Thanks honey." John told her. "This is amazing."
The cocks continued to blow open John's backdoor. The combination of being fucked, rubbing her clit, and watching her boyfriend receive passionate gay sex overwhelmed Lily. She squealed in delight, orgasming and squirting her pussy juice onto her towel beneath her.
Tommy pulled his cock out of Lily's snatch, jerking his shaft and spraying her asscrack with several generous ropes of sticky cum.
"Thanks, Tommy." Lily said. "That was exactly what my cunt was needing."
"Happy to help." Tommy replied.
"My turn." Khloe whispered, winking at John.
The first domino had fallen, and the friction between John's rectum and Dylan's rigid manhood left Khloe in ecstacy. She moaned as she enjoyed her release, pumping her sweet semen deep into John's bowels. As John felt her cum inside him, his own penis twitched, shooting a forceful spray of jizz that landed over Khloe's breasts.
Dylan smacked John's ass cheek as he forced his cock inside and contributed to the pool of sperm Khloe had started. Dylan arched his back as he ejaculated into the loose hole.
"Fuck yes." Lily said as she watched. "Fill that tight ass with cum."
"I don't think it's very tight at the moment." Dylan joked.
Lily giggled as Dylan pulled out of the ruined hole. Khloe gently guided John off of her penis. John lowered himself onto his towel, on his stomach, exhausted from the buttfucking. Lily took the opportunity to get another picture on her phone: a close up of John's red, gaping, semen-filled fuckhole. In his loosened condition, he couldn't help but let the cum ooze out and down his scrotum, and then over his testicles.
"Your asshole looks so sexy right now, babe." Lily told him. "I'm so happy that you got to experience your dream of being fucked by two cocks at once."
"That was intense and incredible." John muttered, still exhausted. "Thank you both so much."
"I promised you my dick in your ass." Dylan told him. "I don't joke around about sex."
"Happy to help you with your dirty little fantasy." Khloe added. "I enjoyed fucking you."
Lily reached over and scooped a blob of the cum mixture from her boyfriend's anus, then brought her finger to his face so that John could have a taste.
"Delicious." John told her.
Lily scooped another blob so that she could also have a taste.
"Yummy!" She agreed.
After a few more moments, Khloe offered to refill everyone's margaritas. Tommy went with her to help, leaving Dylan with John and Lily.
"Thanks for sharing your boyfriend with me." Dylan said.
"Anytime!" Lily promptly replied.
"I've heard you guys mention some club a few times. What is it? Like a gay club?" Dylan asked.
Lily snickered.
"It's basically a members-only sex club." Lily answered. "A lot of members are families. All kinds of sex happens there, but yes, gay sex is also frequent. That's where John took those eleven inches of penis. Right in front of a crowd of people, men and women, cheering him on. His mom even held his hand while he was getting assfucked. It was awesome."
"Sounds like my kind of place." Dylan said. "Any chance I could join?"
"I can't guarantee anything." Lily told him. "But my mom runs it. I can definitely ask her about it and let you know."
"That's cool." Dylan added. "No hard feelings if it doesn't work out. It just sounds like a good place to go and... unload... ya know?"
"I totally get it. And there are plenty of guys, or girls, who would help you unload those balls." Lily said.
"I don't mind fucking a sexy girl occasionally."
"Maybe you can fuck me?" Lily suggested. "My boyfriend got to feel you in his ass. I feel like I should too."
"I would be happy to fuck you in the ass." Dylan told her. "Maybe your boyfriend could get me hard again?"
"Sounds like a plan to me!" Lily exclaimed. "Can you suck Dylan's penis, babe? So he can fuck me in the butt?"
John rolled over and mustered up the energy to get onto his knees. Dylan took a few steps forward so that his soft dick was dangling directly in front of John's face.
"Okay, babe." Lily instructed. "Put the penis in your mouth just like you did back at the gay bar last night."
John opened up and easily but gently sucked the entire soft shaft into his mouth. As he suckled Dylan's genitals, he also fondled his testicles.
"Good boy." Dylan encouraged.
Lily started to prep her backdoor with some lube as she watched John sucking the cock of their new friend. John's dick also started to get aroused again as he sucked the love stick. Especially since he could taste his own ass flavor on Dylan's member.
It didn't take long for Dylan's penis to expand and stiffen in John's mouth. Dylan gently guided John off of his erection.
"Why don't you hold Lily's cheeks open for me?" Dylan suggested.
Lily got on all fours and John got beside her, holding her buns apart. This gave Dylan a clear line of sight to his puckered target, and he easily inserted his penis into the depths of Lily's rectum.
"Mmm that's nice and tight." Dylan said, winking at John. "Way tighter than your boyfriend's ass is currently."
Lily giggled as her anus was being penetrated. "Makes sense. I just have one dick in my ass instead of two like my wonderful whore of a boyfriend."
John continued to hold his girlfriend's butt cheeks as Dylan fucked her. He watched as the penis slid in and out of her rear, the sight causing his own dick to throb with lust.
"Doesn't he have a nice cock?" John asked.
"It's great, babe." Lily agreed. "I can see why you creamed yourself just from sucking on it."
"You two are too sweet." Dylan told them. "It's just a penis."
"But you could've shared it with anyone you wanted." John explained. "We really appreciate you letting us play with it and experience its glory."
Dylan continued to thrust his shaft in and out of Lily's welcoming asshole.
"I'm going to need to hop in the pool after this." Dylan said. "All this fucking has made me really sweaty."
John let go of Lily's buttocks and made his way behind Dylan. He delicately took a muscular cheek in each hand and parted them, admiring the glistening backside.
"Mind if I have a taste of your ass?" John asked.
"Be my guest." Dylan replied as he continued to fuck Lily.
John leaned his face closer to Dylan's exposed bottom. He couldn't resist the urge to inhale his musky aroma first. John then stuck out his tongue, softly swiping at the moist orifice. He then pursed his lips and planted a kiss on the wet hole.
"Tasty!" John noted.
John went a bit lower, extending his tongue and touching it to Dylan's taint. Slowly, he moved up, licking the length of Dylan's salty, sweaty asscrack all the way to the tip. John grabbed his shaft and gave it a few quick tugs, ejaculating onto the grass below.
"Did you just cum from licking my ass?"
"I sure did." John answered, shaking the last few sticky drops from his penis. "You've got a great flavor back there."
"Guess that means it's my turn."
Dylan sunk his cock as deep into Lily's asshole as he could, erupting in orgasm. Semen coated the inside of Lily's rectum.
Khloe and Tommy returned with fresh margaritas just as Dylan was sliding out of Lily's dripping anus.
"What took you two so long?" Lily asked.
"Tommy wanted to get a closer look at my cock." Khloe said with a giggle. "But he wouldn't stop playing with it until he got to see me shoot a load of cum."
"That sounds like Tommy!" Lily told her.
"Can you blame me?" Tommy asked. "It's not every day you meet a beautiful girl with such a pretty cock to match."
"I'm just giving you a hard time." Lily said.
"Thankfully Khloe gave me a hard time, too." Tommy joked.
The group took a short break, enjoying their margaritas. They also took a quick dip in the pool, swimming together in the nude and cooling off, before further indulging in more sexual debauchery.