Please don't forget to read the previous installments if you haven't already. Constructive criticism and feedback is strongly encouraged, please let me know how I can improve as a writer. Cheers, and enjoy!
Jake had only meant to rest his eyes for a second, but realized he had dozed off when the credits of the movie they were watching were scrolling across the screen.
“Hey sleepy head,” Katie cooed into his ear,
“Sorry I passed out,” Jake replied groggily.
“Oh it’s okay, we found a way to occupy the time” Katie said.
Jake’s vision cleared up a bit and he could see Chloe between Katie’s legs, gently lapping away at her friend’s clit.
“Here take this,” Katie whispered softly to his ear as she handed him a pill and a bottle of water.
Jake dutifully obeyed in his half-asleep state and swallowed the pill and chugged the water before excusing himself to brush his teeth and take a piss. When Jake came back into the room he was sporting a raging boner.
“Kate, what did you give me?” He asked.
“Just a little pick me up, figured you needed something to help keep you awake for the rest of tonight’s festivities. Plus, we did tell you we planned to ride that big fat cock of yours all night long.” Kate said with a smile. “Now get over here and shove that cock down my throat.”
Jake needed no further invitation, and climbed onto the bed next to his girlfriend who was waiting for him, mouth open and tongue out. His aimed his cock towards her hole and quickly shoved his cock down her throat, causing her to gag slightly. Jake just put his hands on the back of her head and kept sliding his cock down her throat until her lips were wrapped around the base and his balls were resting on her chin. He gauged her reaction while she adjusted her throat to his member and started to slowly withdraw his prick only to thrust it right back in. As Jake started to face fuck his girlfriend, Chloe removed her mouth from Katie’s snatch began kissing her way up Katie’s body. She stopped momentarily to pay attention to her friend’s nipples, which were now standing proudly, and suckled on them. She kissed her way up and brought her face next to Katie’s. With her mouth wide open, she gave a knowing wink to Jake to use her mouth like he was using Katie’s. Jake obliged, and withdrew his cock from Katie’s mouth then shoved it down Chloe’s throat. He alternated jamming his cock down each of their throats over the next five minutes before he gave them directions.
“Chloe, get on the edge of the bed, feet on the floor” He commanded. “Katie, you get on her back with your feet in the air.”
The two teens eagerly obeyed, and Jake moved into position behind them with cock in hand. He gently slapped the lips of their pussies with his cock before lining its head at Chloe’s entrance. In one fell swoop he entered her and bottomed out, he gave her a few quick pumps before pulling out and doing the same to Katie. He was giving enough pleasure to stimulate each of the girls, but not enough to give them the amount of pleasure they truly craved. He alternated between each of their pussies before they cried in agony.
“Fuck us already,” Chloe called out “Stop being such a tease.”
“You’re the ones that gave me a this thing, I don’t care what you want, I’m fucking you however I see fit” Jake commanded, “And I’m going to fuck each of you in the ass”
The girls squealed in delight at the suggestion. Katie removed her butt plug for the first time tonight and begged to be fucked first. Jake lined his cock up at the already stretched ass of his girlfriend, and entered her. After a few minutes of thrusting, Jake moved to Chloe’s asshole, and entered it for the first time. She was much tighter than his girlfriend was, but that was to be expected as she just lost her anal virginity less than two hours ago. Jake’s hands roamed over his girlfriends tits as they bounced around as he fucked Chloe’s ass, “She is taking this like a champ” Jake thought to himself before increasing his pace on the brunette’s ass. Within a few minutes, Chloe’s moans of passion echoed throughout the room.
“Jesus fuck, Chloe! I know his cock is nice, but you’re going to wake up the whole hotel” Katie said as she got off her friend. Laying next to her on the bed and kissing her in an attempt to muffle her screams of passion.
Less than a minute later, a series of loud banging came from the door.
“Jesus Christ, you’ve done it now,” Katie reprimanded her friend.
Katie got up and without covering herself went to the hotel door, peeking her head around the door as she cracked it open. She was greeted with the same woman from the front desk who had checked them in.
“Hello, my name is Emma, and I am from the front desk. Sorry to bother you, but we’ve received a few noise complaints from guests on the floor, and I’m just checking in to make sure everything is alright.”
“Oh yeah, sorry about that we got a little carried away.” Katie replied “We’ll try to keep the noise down”
“Thank you. I know it is prom so I completely understand. I remember my prom, it was a wild night” The woman responded with a smile as she got caught up in her own nostalgia.
A devilish idea popped into Katie’s head. She opened the door a little wider and stepped out from behind it. “Why not relive it?” she asked with a grin.
The redheaded woman was initially taken aback as the naked blonde stepped into view, but the shock quickly faded as she admired the teenage body before her.
“I would like that very much,” Emma said. Truthfully, she had eyed up the three teens as they had checked in and all night let her mind drifted off and wondered what the three were up to. Which is why, after receiving the noise complaint, she opted to personally knock on the door instead of calling their room. She had secretly wanted to join them, but never thought it would actually happen.
Katie invited the redhead in and gently closed the door behind them, silently motioning for Emma to stay out of sight from the bed. Emma got the hint, that was going to be a surprise for the other two teens in the room.
Katie rejoined the two on the bed and whispered into Chloe’s ear about her plans for the redheaded employee. Chloe nodded in approval before the girls told Jake to lay on the bed. He grudgingly removed himself from Chloe’s ass and did as instructed. Jake’s hips were now at the edge of the bed with his legs resting on the floor. Chloe swung her leg over Jake’s face and lowered her pussy onto his mouth while Katie knelt between Jake’s legs and immediately began cleaning off her friend’s anal juices from her boyfriend’s cock. Once she was satisfied she looked over towards the entryway and summoned Emma to join her.
Emma had removed her heels while she waited, but otherwise remained in her work uniform, consisting of a blazer, white collared shirt, knee high skirt and thigh high stockings. As Emma neared the trio of teens, her eyes were drawn to Jake’s cock. She immediately was impressed by its girth, licking her lips in a mix of approval and anticipation of wrapping them around it. She got on her knees next to the naked Katie who had transferred her mouth to Jake’s balls, offering her boyfriend’s cock to redheaded employee to suck on. Chloe moved her hips off of Jake’s face as she figured the jig was soon up, and opted to join on the action at Jake’s groin.
Once Jake had realized that three mouths on his cock, he lazily lifted his head to see the redhead from the front desk had joined in. Propping himself up on his elbows and watching as the three women pleased his dick.
“You want to ride him?” Katie asked Emma.
“Mmmm, fuck yes I do” Emma replied lustfully as she stood up and started removing her uniform. “I’m just happy I wore matching underwear today,” she thought to herself as she stepped out of her skirt and threw her jacket on a chair before finishing unbuttoning her collared shirt and adding it to her clothes pile. She was soon standing in front of the three teens wearing a matching black bra, thong and her stockings. She straddled Jake’s hips as she got on the bed, and began grinding her panty clad pussy lips across the huge rod that was wedged between their two bodies. She leaned down and lightly kissed the cute guy beneath her. “Do you have any condoms?” She asked gently.
“Um, no. We don’t use them” Jake said.
Emma kept grinding her hips across Jake’s rod as she ran the dilemma through her head. She hadn’t had sex in a few months, and hadn’t had a cock as big as his in a few years. Yes, she wanted him badly but also didn’t care for an unwanted pregnancy or an STD.
“You promise you’re clean?” She asked.
“Yeah, we all are,” Jake said, and the two teens nodded along.
“You can’t cum in me.” Emma mandated, giving into her carnal desires.
“Well no shit princess, I’m not letting my boyfriend blow his load into every girl he meets” Katie spat back.
Emma looked down at Jake, who nodded his head as he agreed to her terms, before resuming the slow rhythm of her hips on Jake’s rod. She reached back and unclasped her bra before adding it the rest of her pile of clothes. She gave herself one last thrust of pleasure before standing up and removing her panties, revealing her trimmed bush to the room. She licked her fingers and ran them across her slit before re-straddling Jake’s hips. As she got into position, Chloe gently grabbed the hand Emma had used to lubricate herself with and sucked on her fingers.
“She tastes good,” Chloe said to Katie before moving in and kissing her.
The teenage friends swapped tongues and reveled in the light, tangy flavor of the redhead who was now easing herself down on the thick cock that stood erect between her legs.
“Yeah she does,” Katie cooed back before two resumed kissing.
It took Emma a few strokes to get used to Jake’s girth but once acclimated she was soon riding him to her heart’s content, eliciting moans of approval as a result.
Katie lay down next to her boyfriend and raised her knees up, resting her feet on the edge of the bed. She summoned Chloe over before she lay her head back, closed her eyes and played with her clit. Emma’s pace slowed once Katie got on the bed, and she had moved a hand down and started tracing her fingers along the teen’s inner thigh.. She gently rubbed her fingers around the slit, coating them with Katie’s juices, before sticking a finger inside Katie’s cunt. A soft moan of pleasure emanated from Katie as the receptionist’s finger explored her depths.
Chloe knelt between Katie’s open legs, assessing the situation before her. “Can’t play with the clit, since Katie’s already got that. Can’t lick her pussy since Emma had that.” So she took the only open hole available, and with her arms she raised Katie’s legs off the bed, and exposed Katie’s asshole. She licked her lips, tilted her head sideways and began licking her friend’s sphincter.
“Oh my you are a dirty bunch,” Emma said to no one in particular.
“Takes one to know one,” Katie said between moans. “Last… I… Checked” Katie got out before the first wave of an orgasm hit her. “Last I checked, you were the one who wanted to personally stop by a room with three high school seniors, that makes you a dirty old pervert.”
“I never said that I wasn’t,” Emma said with a wink, lifting herself off of Jake’s cock and kneeling between his legs.
She immediately wrapped her lips around the head of his cock, and swallowed his cock.
“OH FUCK!” Jake exclaimed, as Emma had just deep-throated him in the blink of an eye.
Jake quickly brought a hand to the back of her head and held her down on his cock as he savored the feeling of being buried in her throat. As she started to gag, Jake let her back up and asked, “Jesus fuck, where did you learn to do that? That was amazing”
“I have a few toys, but not as big as you,” She said with a smile. “I have an idea, how about you” she paused; now pointing to Katie. “How about you get on top of your boyfriend, so I can suck his dick and lick your pussy. And you can eat my pussy while I do that.” Now motioning towards Chloe.
The three teens got into place and Emma’s improvised plan played out in front of her. She would bob on Jake’s cock for five or six times, then run her tongue across Katie’s pussy five or six times. This carried on and eventually morphed into Jake getting his dick sucked then sliding it into his girlfriend’s snatch when Emma focused on Katie’s clit. Chloe was content at the back of the line, and was merrily lapping away at Emma’s neatly trimmed cunt.
*Bzzzzzt* *bzzzzzt* *bzzzzzt*
“Oh shit, my pager!” Emma said with a tone of alarm in her voice, and quickly vacated her place, digging through her clothes to get to it.
Jake had resumed fucking his girlfriend, and Chloe had assumed Emma’s place and was now gently tonguing Jake’s balls as they bounced up and down with the rhythm of his thrusts.
“I’ve got to get going,” Emma said, stepping into her panties and then clasping her bra and putting it into position.
“Are you going to cum soon?” Emma inquired, mentally weighing the outcome of continuing the fun here versus possibly losing her job.
“Oh…Fuck… I’m.. Right there,” Jake said with between thrusts.
“Where do you want him to cum?” Chloe asked Emma as she looked over her shoulder.
Emma quickly returned to the edge of the bed, and took Chloe’s spot between Jake’s legs.
She grabbed a hold of the base of Jake’s cock and as Katie raised her hips, she pulled him out and put his head in her mouth.
“Let me know when you are going to cum” She said before she resumed sucking on Jake’s tip.
A few short strokes later, and Jake gave his warning. Emma quickly removed her mouth, to Jake’s dissatisfaction, and pointed his cock towards Katie’s belly. She jerked him off as fast as she possibly could until Jake’s load shot out, spraying his girlfriends torso with his cum. He was astonished that he was able to cum nearly as much as he did based on the amount of orgasms he had that night. Emma seemed equally impressed at the amount as she quickly kissed her way up Katie’s body. She lapped up the cum that was dribbling down her torso and pooled it in her mouth. She moved up and kissed Katie, sharing the cum she had collected with the girl who had invited her in. As the two finished kissing Emma thanked them for the evening, and insisted that she really had to go. As she finished getting dressed, Chloe finished licking up the traces of cum that remained on Katie’s body. Once Emma had gotten dressed, she gave Katie a quick one over, “Damn you’re sexy, and it looks like I missed a spot” she said as she scooped up a small glob of cum that was dribbling down Katie’s side and brought it to her mouth. “One for the road” Emma said with a smile before she left the room.
“Holy fuck that was good!” Katie panted in exhaustion. “I feel like I can sleep for a week.”
Jake looked down and despite cumming a truck load, he was still rock hard thanks to the pill his girls had slipped him. “Uh are you really going to leave me like this?” He asked his girlfriend with a laugh.
“Sorry babe, I’m exhausted, I’m taking a shower then passing out.” Katie proclaimed as she made her way to the bathroom.
Jake turned his attention towards Chloe, “How about you?”
“I’m in,” She said with a devilish grin before lying on the bed and spreading her legs.
Jake climbed between Chloe’s legs and lined up his cock at her entrance, which was dripping thanks to the show she had just witnessed. At the behest of Chloe, Jake was insisted to forgo a slow and steady pace and quickly assumed a rapid pace hoping that it would force another orgasm. The two teens continued fucking at a furious pace until Katie stepped out of the shower. “Sorry love birds, I’m turning the lights out, try to keep it down please.” As if it was a natural thing for a girlfriend to say as her boyfriend’s cock was buried inside her friend’s pussy.
The lights went out, and they slowed their pace, trying not to shake the entire king bed with their motions. After a few minutes, Jake whispered into Chloe’s ear. “I’m not going to cum like this, we need to change positions”
“Fine, roll over, I’ll climb on top” She insisted.
“No, I want you on your stomach” He countered.
She rolled over, spread her legs and lifted her hips up as he entered her from behind, forcing his entire weight into her. This was getting him closer, but still not quite over the edge, so he started giving her long strokes, pulling out until just the tip of his head was inside her, and then bringing it back home. A few more strokes like this and he was at the cusp of another orgasm.
“I’m going to cum,” He said softly.
“Do it, cum in me,” Chloe whispered harshly
Jake emptied his balls into Chloe for the second time that night, and started feeling his dick soften inside her. “Finally!” he thought to himself. He pulled out of Chloe and offered to let her go to the bathroom and get cleaned up.
“No need,” she said and despite it being dark in the room, Jake could see the faint outline of Chloe scooping the cum that was dripping out of her pussy up and bringing it to her mouth.
With Chloe cleaning herself up, Jake excused himself to the bathroom, where he relieved himself and washed up. He was drenched in sweat and coated with cum, so he opted for shower before bed. He cleaned his body in his normal routine, and once he got to his groin, his cock instantly sprang back to life. “What the fuck!” he said, his voice fortunately drowned by the water cascading around him. He rinsed the soap off his body before stepping out of the shower, and dried himself off.
Jake cursed his two girls for giving him the pill as his erection proudly stood at attention. He walked back out to the bedroom; he heard the feint snores of Katie and Chloe signaling they were already asleep. “Well fuck,” Jake thought to himself since both of his girls were already passed out. He’d have to go find another way to get rid of his erection.
He rummaged through Katie’s bag, and found a T-shirt and Sweatpants that she had packed for him and threw them on. The loose fitting sweats did nothing to hide his glaring erection, so he tucked it in his waistband before he grabbed his phone and left the room.
Jake made his way down the empty hallway towards the ice machine and filled a bag of ice, hoping to force his erection into submission. He turned around with a bag of ice on his cock and was immediately greeted by Candice who was wearing a similar outfit as he was.
“Rough night,” She asked, noticing the ice pack.
“Yeah you could say so,” He replied.
“Damn, that’s too bad,” She said, pausing slightly “and here I was, thinking how nice it’d be nice to have another go.” She said with a devilish grin.
Jake’s only other opportunity would be to try to get Emma away from the front desk again, which would be slightly awkward walking up with a glaring erection or a bag of ice covering his crotch.
Jake simply dropped the ice on the floor, and pulled down his pants which caused his erection to flop down and settle pointing straight at Candice.
“Well let’s do it” Jake said.
Candice smiled as she got to her knees and started sucking on his member. Her mouth quickly warmed his cock, which was barely cooled due to the ice, and began sucking him in earnest. She had definitely improved from the first time she had taken him into her mouth at his teacher’s house; she really seemed to take the coaching that Jake gave her in his living room. The chubby blonde started making quick work on his cock and even was able to take him completely down her throat. She was taking a breather, and licking his balls when they heard the elevator down the hall ding causing the two of them to freeze momentarily. They heard the soft patter of footsteps getting closer and scrambled to regain their clothes and composure and just barely got in a decent state before a member of the hotel staff walked around the corner.
“That was close, come on, let’s go to my room” Candice said with a sense of urgency.
“What about Alexis?” Asked, remembering their plans to share a hotel room.
“Fuck, good point.” Candice replied. “What about your room?”
“No good, Katie and Chloe are there.” Jake said.
“Well I don’t want to get caught out here, and Alexis is a pretty heavy sleeper. So we’ll just have to be quiet.”
The two teens nodded in agreement and quickly made their way to the door. Candice opened the door slowly, and motioned for Jake to stay outside as she made sure Alexis was still sleeping. Jake waited outside for a minute before Candice brought him inside. Once the door closed, it was pitch black and Jake immediately felt his pants being pulled down and immediately felt Candice’s mouth engulf his cock. She gave him a few sucks before telling him to fuck her from behind. He knelt down and felt around in front of him before he found his mark and pulled her hips in towards his, he felt that she had already taken off her pants and he aimed his cock between her thighs, and after a few light hip thrusts he found her cunt and entered her.
“Just make sure you pull out” She whispered before Jake started slamming his hips into hers and continued to pick up the pace until her round ass started clapping with every stroke. Both of them suddenly became aware of the noise they were making, and Jake withdrew his cock from the wet hole between Candice’s legs.
In the few minutes of being in the dark, Jake’s eyes had adjusted and he was able to see the outlines of the room. He could see Candice was now on her back with her legs spread open. He guided his missile towards her entrance and shoved it back in eliciting a soft moan from underneath him. Jake quickly used a hand to cover her mouth and stifle any additional moans as he picked up his pace and his cock slid along Candice’s velvety walls which were slick with her juices.
“Oh come on, come for me, let me taste that cum” Candice pleaded from underneath his hand.
Jake cursed his stamina, as he tried willing himself to cum for the fifth time that night. He continued pounding away at Candice’s cunt, which got slicker and slicker with each of his strokes. Candice’s cunt soon clamped down on Jake’s cock as she had her own orgasm. The contractions nearly brought Jake to his own orgasm and he rapidly withdrew his cock and straddled Chloe’s body and stuck his cock between her breasts. Candice got the idea and brought her hands to each side of her heavy tits and held them together as Jake slid his cock between them using her own cum as lubrication. He sharply thrust his cock between the pillowy tits beneath him and soon was at the brink of what he hoped would be his final orgasm of the night. The tingling in his balls let him know his orgasm was fast approaching, and sensing it would be a good one, he grabbed his phone to document the night’s grand finale.
“Oh fuck, I’m going to cum” He stated softly.
With the glow from his cell phone, Jake could see Candice angle her head towards his cock with her mouth open and tongue out. With another few thrusts, Jake was over the edge and despite it being his fifth load of the night; he fired rope after rope of hot jizz out of his cock, and splashed Candice’s face and tits. The camera’s flash lit up the room as Jake snapped a picture of Candice holding his shaft, and kissing it with her cum covered face.
“I want a copy of that,” She said nodding towards his phone.
Just as Jake was about to respond, they heard movement coming from the bed.
“Oh shit,” they whispered in near unison as they realized that Alexis was stirring.
Jake quickly grabbed his clothes and made the split second decision to risk being caught nude in the hallway over explaining to his sister that he had just fucked her friend. Fortunately for Jake, he made the right decision, the hallway was clear, and he quickly put his clothes on. Just as he was about to head back to his room, he heard a muffled conversation from the outside of the door.
“Is that cum on our face? You fucking slut!” Alexis chided
“Yeah, we were trying to be quiet; we didn’t mean to wake you.” Candice responded.
“Oh I was awake for most of it, I heard you two come in. I have to admit, I got pretty hot hearing you get fucked a few feet away from me.” Alexis confided.
“Oh, you were playing with yourself?” Candice asked.
“Yeah, I contemplated joining in, but didn’t want to scare him off. How was his cock? Was it big?” Alexis asked, completely oblivious that she was inquiring about her own brother’s cock.
“It made me cum, so I’d say it was good” Candice said, suddenly aware of how awkward it is describing Jake’s genitals to his twin sister.
“Well he tastes good,” His sister said.
Wait a minute; Jake thought to himself, did his own sister just lick his cum off of her friends face? He had a momentary flashback to his 18th birthday, and Alexis being forced to eat his cum out of Ms. Dyers’ pussy.
“Come on and eat my pussy Candy, I’m all wet from hearing you two fuck. And leave that cum on your face, it’ll be so hot seeing it as I fuck your mouth” Alexis said.
The gears kept rolling in Jake’s head. Both him and his twin are sleeping with Candice? Is that why they went to prom together? It was too much for Jake’s sleep deprived mind, he looked at his phone and it was nearly 3 am. Jake quickly made his way back to his room, quickly undressed and jumped into bed with his girls.