living with a goth and tomboy

Summary:One man's sexcapades with his goth and tomboy roommates.

Chapter 1: Meet The GangNotes:(See the end of the chapter for notes.)

Chapter TextWanted to get started on this project, so let's introduce the roommates.

The Goth:

Full name: Lilith Raven 

Occupation: Tattoo Artist

General Description: Stands at 5 foot 8.5 inches. Ghostly pale skin. Black hair that's almost constantly dyed with purple streaks. Piercings on ears, nose, tongue, belly button, and nipples. Tattoo of a black rose on left arm and a black butterfly tattoo just above her ass. D-cup breasts. Huge bubble butt. A little chubby but not super fat(Use this picture for a general vibe as to what she looks like: https://rule34.xxx/index.php?page=post&s=view&id=3604679 )

Personality: Generally moody and cynical, but can be playful towards those who can get close.

The Tomboy:

Full name: Ashley Jordan

Occupation: Mechanic

General Descriptions: Tall at just over 6 feet. Bright red hair in a high-top ponytail. Skin covered near head-to-toe in freckles. Lightly tanned except on breasts and butt. C-Cup breasts. Firm and toned but still plump butt. Often wears bandages around her arms, solely for decoration.

Personality: Outgoing, energetic, sporty and playful. Likes to be rough but cares deeply for those closest to her. Isn't one to tolerate others being pushed around.

The Male:

Full name: Chase Nicholson

Occupation: Freelance Web Designer

General Description: About 5 foot 8 inches in height. Fair skinned with dark hair. Rather skinny but not emaciated. Rarely seen without glasses. 8 inch long penis. Looks a bit like Allister from Pokemon Shield.

Personality: Introverted and keeps to himself. A bit of a horny idiot, but not to the point of letting it get out of hand. Has a wealth of pop culture knowledge.

It's really late, so I'll get to the good stuff later.

Notes:Edit: Changing the names and occupations.

Chapter 2: Wake Me Up When It's All OverSummary:How a day commonly starts in their apartment.

Notes:(See the end of the chapter for notes.)

Chapter TextChase moaned slightly as light shone through his window, opening his eyes to a familiar sight: his roommates Lilith and Ashley sucking him off. The three of them are childhood friends who several years ago agreed to a relationship of friends with benefits, so waking up to a blowjob was far from uncommon. Chase had no reason to complain, especially seeing how their bodies contrasted each other, with Ashley's lean muscles vs Lilith's somewhat heavy-set frame. Lilith definitely had her extra pounds, but carried them phenomenally, shown by her huge bubble butt hoisted into the air next to Ashley's. Ashley's butt was somewhat smaller than Lilith's, but still very sizable, with her athletic lifestyle making it toned and firm. 

Moving forward, out of nowhere, the two of them stopped the blowjob with an exaggerated slurp from them both. Chase whined and asked, "Hey what gives?", to which Lilith replied, "Sorry Chase, but we've got work to do today, so let's cut to the good stuff. Some of us have jobs that require us to leave the house, you know." The three of them had jobs that meant they had to rush through their morning fun. With that, they climbed into position, with Ashley lowering herself onto Chase's massive cock and Lilith sitting on Chase's face, smothering him with her thick ass. With that, they got to work.

"Ah, ah, ah! Fuck that feels so fucking good! Why do you have to have such a huge cock?", Ashley cried out as she bounced herself on Chase's 8 inches. Lilith moaned as Chase licked and lapped at both her pussy and her asshole, and in between moans she said, "Hard to believe you're always shocked, given how many times you've taken it, you dumb cock slut!", to which Ashley replied, "Look who's talking, you fat ass whore!", giving Lilith's fat ass a rough smack, leading to the goth giving Ashley's bottom a rough smack and saying, "Don't act like you don't have some serious cake yourself, okay?". Chase would've weighed in, but his mouth was a little occupied at the time.

After a while of this, the three of them hit their limits, with Chase firing his load in Ashley's slit, which gushed around him, and Lilith's pussy squirted all over his face. The two of them got off and now it was Ashley's turn to get on her back with Lilith on top of her in a 69 as they ate each other's pussies. Chase was far from idle, forcing his massive dick into Lilith's tight asshole, and started pounding away. Whatever parts of his cock that wasn't inside of Lilith's rectum, Ashley gave a good licking to.

This went on for a little longer, but soon they remembered that they were on borrowed time, so wrapping things up, Chase fired off a load into Lilith's asshole before pulling out, at which point Lilith and Ashley untangled themselves and got on their knees before Chase, who stroked himself a bit before spraying both of their faces with what was left of his seed, which they two of them licked off of each other as they made out. Once their faces were totally cum free, Ashley looked up and said, "Thanks for that, Chase. We needed that", to which Chase replied, "Happy to help, guys". Lilith then said, "I don't know about you guys, but I'm starving, so let's get some actual food in us before we leave." And with that, they all left Chase's room, with Chase enjoying the sight of his roommates' bubbly bottoms sway to and fro as they walked.

Don't be fooled. The three of them weren't lovers, and there was no envy or possessiveness for any of them. They're all just friends, just with benefits. Lots and lots of benefits.

Notes:This is more of a test chapter. Comment if you want me to continue.

In the future, if I decide, the three will get some one-on-one time with each other in some chapters.

Chapter 3: I Want It Painted BlackSummary:Chase and Ashley visit Lilith at work.

Notes:Might make a trend of song lyrics being chapter titles, who knows?

Edit: Severely overhauling a couple chapters with new occupations and names.

Chapter TextChase and Ashley walked together into a local tattoo and piercing parlor, called the Reaper's Inkwell. It's not their usual hangout, but they were there for Lilith. Lilith was a tattoo artist and piercer there. She didn't mind the work and got glowing reviews from customers, and actually was a customer there herself once. Lilith still gets a little wet recalling the day she got her butterfly tramp stamp and the afternoon she shared with the artist who gave it to her, but that's a story for another day.

It was a slow day in the early afternoon when Chase and Ashley arrived. Lilith noticed them quickly and smiled, saying "'Sup, guys?". Chase spoke up first, saying, "We didn't have anything to do today, so we thought we'd stop by. Looks like a slow day today." Lilith responded with, "Yeah, but it's okay. You know I like my peace and quiet I'm actually on break and finished lunch." Ashley spoke next, saying, "Maybe we can help you pass the time until your break's up." Lilith grinned even wider and said, "You read my mind." With that, Chase and Ashley got on their knees, with Ashley in front of Lilith and Chase behind Lilith. Lilith then unzipped her jeans and pulled them down, along with her underwear, baring her huge bubble butt. With her bottom exposed, Ashley and Chase got to work, with Ashley licking Lilith's pussy and Chase licking her asshole.

Lilith moaned and squealed loudly as her friends devoured both of her lower holes. "Holy shit that feels good, guys! Don't stop! Don't you dare fucking stop!", Lilith wailed at the top of her lungs. Her friends obeyed, forcing their tongues into her holes as far as they could possibly go, lapping and swirling around the inside of each hole. They never stopped, even for a moment, fucking the goth with their tongues like their lives depended on it. It's a good thing they've had so many years of practice.

It wasn't long before Lilith let out another cry and came, her pussy gushing onto Ashley's face, who slurped it up happily. The two pulled away from Ashley's holes with a slurp and let her catch her breath. Once they felt ready to go on, Lilith bent over to produce a large strap on(one can only guess how she snuck that into work), which she quickly donned and ordered Ashley to mount her, which she did without hesitation, sinking her tight pussy onto the plastic. The tomboy moaned out happily as Lilith pounded her slit, which only got louder when Chase stepped behind her and forced his 8 inches into her tighter asshole, making her shriek in pleasure as she was fucked in both of her lower holes.

"Ah, ah, ah, ah! Don't stop, guys! It feels so fucking good!", Ashley wailed happily. Indeed, neither of them intended to stop, even for a second. Lilith, enamored by the sight of Ashley's bouncing tits, latched her mouth around one of her nipples, sucking on it like a nursing baby, making Ashley cry out in even greater pleasure. The tongue piercing Lilith got so long ago was definitely worth every penny. Chase, not to be outdone, made a grab for Ashley's bouncing ass and gave a series of rough smacks, turning her buttocks as red as her hair.

After a while of this, Chase moaned as he fired his load into Ashley's rectum as she squirted all over Lilith's strap on. Going for one final round, Ashley got onto all fours and spread her butt cheeks to reveal her gaping and cum-filled asshole, which Lilith didn't waste a moment in sinking her strap on into. Chase came up behind the plus-sized goth and forced his still hard cock into her asshole, making her shriek in joy. It didn't take very long to establish a good rhythm, wherein every time Chase thrust his hips forward, Ashley forced her plump ass backwards, and whenever Chase reared back, Lilith thrust forward. Nothing was held back from any participating party and that's exactly how they liked it.

Eventually, they all reached their limits once more, with both girls' pussies gushing out and their assholes spasming around whatever was in each one, and Chase unleashed a load to flood Lilith's bowels. Pulling apart, they saw that break time was over, so they quickly got dressed and Chase and Ashley left, and as they did, Lilith merely stated, "You guys sure know how to make a slow day a lot more exciting."

Chapter 4: Shut Up And DriveSummary:Lilith and Chase visit Ashley at the body shop and play with her.

Notes:Changed Ashley's job.

(See the end of the chapter for more notes.)

Chapter TextAshley's place of business was at a car and motorcycle mechanic place. Some assume that because Ashley falls under the tomboy archetype, she's not very bright, but that's far from the truth. As a kid she always had a fascination for cars and machines, and loved doing tinkering projects with her father. Rather than a normal jumpsuit, Ashley's work uniform was a tied up plaid shirt and rather skimpy jeans shorts, though (for clear reasons) nobody has seemed to complain.

Chase and Lilith found Ashley bent over, working under the hood of a customer's car. The two roommates found themselves less interested in the work and on their friends' jeans shorts-clad bubble butt. Eventually she finished and the customer paid and left, when Ashley turned to see her friends watching her. "Hey guys", Ashley said, "I'm guessing you two enjoyed the show." "That we did", Lilith said, "now what's say we have a little cool down?". Ashley grinned and put away her tools and said, "Hell yeah", and the three went to the break room.

The three of them went into the thankfully empty break room, kissing and feeling on each other. In a flourish, all 3 of them were left completely naked, and Ashley decided to take the lead, sinking herself onto Chase's 8 inches and bouncing herself wildly on top of him. Not wanting Lilith to feel left out, she ordered her to lick both her pussy and whatever of Chase's cock wasn't inside of it, which she did happily.

"Ah, ah, ah, ah, ah! Fuck that's good! Don't stop, either of you!", Ashley wailed at the top of her lungs as she rode Chase with everything she had. Her friends were glad to obey, with Chase grabbing the tomboy's plump yet firm backside, giving an occasional spank, and Lilith licking both of her friends' private parts, putting her tongue piercing to excellent use. Determined not to be the only one with untouched parts, Lilith slipped a hand down to roughly finger her by now soaking wet pussy, desperate for when she'll get some action.

It wouldn't be long, and with a moan from everyone, Ashley's pussy gushed all over Chase's cock, which responded by firing a load of cum into her slit, and Lilith's own pussy squirting all over her hand. Ready to go again near instantly, Ashley dismounted and grabbed a strap-on, slipping into it and ordering Lilith onto all fours. With minimal warning, Ashley shoved the entire strap-on into Lilith's asshole and started pounding away. Lilith moaned out happily, which only got louder when Chase got under her and drove his hard on into her tight pussy, which she happily accepted. Every time Ashley thrusted forward, Chase then did the same, acting as a well-oiled machine DP'ing their somewhat heavy-set friend. Lilith could only shriek at the top of her lungs, begging her friends to fuck her stupid, which they were all too happy to.

After a while of this, the three of them hit their limits again and Lilith's pussy gushed around Chase's cock, which dumped a fat load into her cunt. Chase pulled free and left Lilith on all fours, with Ashley kneeling next to her as their friend jerked off to fire off one last load onto their faces, which led to the girls making out, licking up and swapping the cum that coated them. Once it was all gone, Ashley saw a new car coming in and sent her friends on their way, happy to have some friends to spice up her day.

Notes:The next couple chapters will feature Chase getting one on one time with each of the girls.

Chapter 5: Get Your Game On, Go PlaySummary:Chase is alone with Lilith and plays video games with her, but soon finds himself interested in a different game.

Chapter TextSitting on the bed in Lilith's room, Lilith and Chase have their Nintendo Switches out and are playing some online Mario Kart 8 Deluxe. Ashley was out for the day working at the shop, so Lilith and Chase were all by themselves. Video games were a favored past time for all 3 roommates, but Lilith was probably the most avid gamer of the trio.

This was proven by Lilith curb-stomping Chase over and over, until eventually he got bored and set down his Switch and sat back to watch Lilith play alone. Chase's focus quickly shifted away from gaming and instead on Lilith's prone form. The plus-sized goth was clad in a simple purple pair of panties, but they looked at least a couple sizes too small for her, given the way her enormous bubble butt seemed to devour her underwear greedily. It wasn't long before Chase found himself growing hard and his mouth watering and found something new to play with. Without warning, he reached down and roughly clamped his hands down on Lilith's huge butt cheeks, making her jump a little, but clearly not impeding her playing. Taking things further, Chase began basically playing around with her fat juicy rump, squeezing, kneading, and sometimes smacking her thick behind. Lilith let out a tiny round of soft moans, but otherwise took it all without complaint and clearly her playing wasn't affected. "Let's see how you handle this", Chase muttered under his breath, too softly for Lilith to hear him, and pulled the crotch of her panties aside to show her tight pussy, and without warning, his shoved himself into it.

Within seconds, Chase established a quick and rough rhythm of pounding Lilith's slit. Lilith had seemingly been more partial to anal sex, so her pussy was sometimes neglected, making it feel near virgin tight, even though he knew for a fact that she was the furthest thing from a virgin. Chase didn't hold back, ruthlessly fucking her without an iota of restraint. Enjoying the sight of her bubble butt jiggling around, he gave a series of rough smacks to turn her buttocks red. Normally Lilith would be crying out at the top of her lungs and begging for more, but aside from soft moans, she seemed to barely react, taking it all without problem. However, she did eventually squirt around Chase's cock, more than once as Chase didn't relent even for a moment.

Eventually, Chase hit his limit and gave one more balls-deep thrust as he blew his load, flooding Lilith's pussy with his seed. Even still, Lilith remained stalwart in her gaming efforts. Taking things further, he moved her panties further aside and spread her butt cheeks to reveal her tight puckered asshole. With his cock still slick with both of their juices, Chase forced his cock up her ass, going balls-deep in one go. It took very little time before he re-established his earlier rhythm, viciously pounding Lilith's ass and continuing to grope and spank her massive booty. Lilith's moans were slightly louder, but she kept herself laser focused on her game, even as Chase picked up the pace, not slowing down for even a moment.

After a while of this, Chase couldn't take it anymore and fired off another load to fill Lilith's rectum. Just then, the race was over, with Lilith in first place of course. She turned her head and smiled at Chase saying, "Thanks for that." Chase then said, "No problem. Surprised you could play so well with me fucking you like that", to which Lilith replied, "Same. Now let's see if you can take it", shifting herself to put her head between his legs, stroking and licking his still hard cock as he started the race.

Chase wasn't sure if he could keep up the same focus Lilith showed, but damn if he wouldn't try regardless.

Chapter 6: Let's Get PhysicalSummary:Ashley takes Chase for a run, and has a special cool down with him.

Chapter TextNobody would call Chase a particularly athletic person, especially compared to his roommate Ashley, but she somehow managed to talk him into going on a run with her. He lagged behind and struggled to keep up, but it's wasn't all bad. Being behind her gave him a great look at her plump ass bouncing, wiggling, and flexing about, encased as it was in a pair of tight bike shorts, and even from behind he got a look at her boobs bouncing around in her sports bra. Lilith may have the edge in sheer size when it came to butts, but nobody with functional eyes would call Ashley's backside flat.

Their run brought them underneath a bridge that run over a creek, with Ashley having her hands on her knees, giving Chase a nice view down her sports bra, and it didn't go unnoticed the way Chase stared at her tits, nor the raging boner in his own shorts. Ashley licked her lips and approached Chase, saying, "Thanks for coming out with me, Chase!". Chase breathlessly replied, "It's nothing." Ashley then said, "You know, running isn't the only way to work up a sweat", making no secret of the way she stared at Chase's bulge, and without a word, she pushed Chase down to place him in a sitting position, yanking off his shorts to reveal his achingly hard 8 inches. Ashley lifted up her sports bra to show him her bouncing breasts, and then lowering her shorts to reveal her tight and already somewhat wet pussy. With no more delay, she mounted Chase, lowering herself until his cock was fully engulfed by her slit, and with that, she got to work.

"Ah, ah, ah, ah! Fuck this feels good! Don't stop, please!", Ashley moaned out loudly, no longer giving a fraction of a rat's ass if anybody could see or hear what was going on. Chase had no interest in stopping her, knowing that he probably couldn't even if he wanted to. He took some initiative and latched his mouth around one of her nipples, while letting his hands go south to grope, squeeze, and sometimes spank her bottom. Chase was always turned on by the way Ashley's body was lightly tanned, but her tits and her butt were near ghostly pale similar to how Lilith was near head-to-toe, so Ashley kept up this tanning pattern.

Ashley's riding had gotten more than a couple orgasms out of her, and Chase fucked her through all of them before finally he himself came, firing a load into Ashley's pussy and making her shriek happily. Ashley dismounted and got onto all fours, pointing her tight round butt in Chase's direction, wiggling her bottom and spreading her cheeks to bare her asshole. Seeing as how his cock was still slick with their shared juices, Chase didn't waste another second in forcing himself into her rectum, balls-deep on the first go.

Chase very quickly got to work mercilessly pounding Ashley's tight ass, holding nothing back as he tore into her. Ashley seemed to enjoy if at all indicated by her loudly wailing and playing with her cum-filled pussy, saying, "Harder, Chase! Fuck my ass harder! Show my butt no mercy!". He gladly obeyed, savagely pounding her pucker and re-establishing a rhythm of spanking her big round bottom, holding absolutely nothing back. He knew from experience that a rough-and-tumble girl like Ashley loved the rough stuff, to the point she pretty much hated gentle sex, and he knew every sweet spot to hit to get her gushing.

After a while of this, Ashley hit another orgasm, her pussy squirting against his balls and her asshole spasming around his cock, which triggered his own orgasm as he flooded her bowels with his seed. Satiated, they separated and got dressed, with Chase noting how Ashley made a show of bending over to pull her shorts back up. Once they were both decent again, they headed back for home, with Chase's gaze never leaving Ashley's behind, noting the way his cum started to dampen her shorts as it leaked from her holes.

Exercise never felt so good.

Chapter 7: Girls Just Wanna Have FunSummary:When Chase is away, the girls will play.

Notes:If you're confused, tonight I went back and changed all their names.

Chapter TextLilith and Ashley were sitting around in their apartment, bored out of their minds. Chase was out with one of his web development clients, who insisted on meeting in the flesh over lunch at a diner, meaning he wouldn't be back for a while. Lilith sat on the couch and scrolled on her phone idly and Ashley did stretches in front of her. Lilith couldn't help but notice the way Ashley's sleep shorts stretched around her firm toned butt cheeks, which gave her an idea.

"Hey Ash", Lilith called out, "Why don't we make a little bet?". Never one to say no to a bet, Ashley asked, "Sure thing. What's the wager?". Lilith smiled and said, "You and I will 69 and eat each other's pussies. Whoever cums first loses, and the winner gets to fuck the loser up the ass with a strap.". To be honest, it soundly like a win-win for both of them no matter who won, so Ashley smiled and said, "You're on, Lil!". With that, Ashley took Lilith's place, laying on her back on the couch as Lilith straddled her face, pulling down her panties, before discarding Ashley's own shorts and underwear, leaving both girls naked from the waist down. With that, the two of them got to work.

Lilith and Ashley ate each other's pussies feverishly, licking and lapping as if it were their last meals on Earth. They'd been playing together for years, so they knew exactly which buttons to push to get each other gushing on their tongues. However, both also possessed exceptional sexual stamina, able to go a while without orgasm and have multiple before getting tired. They lapped and swirled inside of each other's slits as deep as their tongues could possibly go. Ashley found herself interested in Lilith's giant butt smothering her face, so she took things a little further and started fingering the goth's asshole. Lilith moaned into Ashley's pussy at the feeling, and not to be outdone, decided to return the favor and fingered the tomboy's asshole as well, both of their moans muffled by their pussy licking.

It was a tightly contested game, but in the end, Lilith prevailed, feeling Ashley's pussy squirting on her face as her own cunt did the same seconds later. Lilith pulled away and said, "Looks like I win, and now I'll be claiming my prize", and with that, she got off of Ashley and quickly ran off to fetch her strap-on, already wearing it once she got back. Ashley accepted her loss and bent over, pointing her toned bottom at Lilith, who gave the shapely cheeks a rough smack, making the tomboy cry out happily. Spreading Ashley's plump buttocks to reveal her pucker, Lilith wasted no time sinking the plastic cock into her rectum and getting to work.

Ashley moaned and cried out happily as Lilith pounded her ass with the strap-on. "Yes, ah, fuck that's good! Fuck me, Lilith! Fuck my tight little ass with your fat cock!", Ashley moaned and cried out happily. Lilith was more than happy to fulfill her request, hammering into her tight rectum with all her might. The pitfall of having a strap-on and not a real cock meant she couldn't feel the inside of Ashley's ass the way Chase or any other AMAB person could, but it was still enjoyable to use her like this, especially since the toy was double-ended, letting Lilith have something inside of her at the same time. Lilith grinned and smacked Ashley's muscular butt cheeks, which possessed just enough fat to them to still be jiggly. Bending over, Lilith whispered into Ashley's ear, "You know, you and Chase are always talking about my ass, but don't act like you don't have some serious junk in the trunk yourself", giving said junk in the trunk a series of merciless spanks to turn Ashley's butt cheeks as red as her hair, perfectly timed with the savage ass pounding she was giving, coupled with yanking on the tomboy's ponytail like the reins of a race horse. Ashley could do nothing but cry and whine in pleasure at the relentless pounding she was getting, loving every single second of it, of course.

All this became too much for the poor redhead and she wailed at the top of her lungs as her pussy released a gushing orgasm as Lilith did the same. Lilith removed her toy and she and Ashley cuddled on the couch, exhausted. Even as just friends(with loads of benefits of course), they and Chase still liked to snuggle once finished fucking each other silly. The two of them saw a text, saying that Chase's meeting went a little longer than expected and wouldn't be back for a while. The girls smiled at each other, preparing to go another round with each other.

Even on a seemingly boring afternoon, with roommates like these, dull moments rarely last for long.

Chapter 8: Rain On MeSummary:After a hard day's work, the three friends shower together to save water. Yeah, let's go with that.

Chapter TextChase quickly discarded his clothes and began to shower. People think people like him who work from home most of the time have lackluster hygiene, but that's not even close to true. As he scrubbed himself down, he was greeted by the sight of his roommates, Ashley and Lilith. The three of them always showered with the door open, inviting anyone to join. The girls knew that Chase had a voyeur fetish, so it would be hypocritical of him to discourage them to engage in it. As such, Chase barely reacted to the sight of his friends watching him, casually saying, "You two like what you see?", to which Lilith replied, "Obviously". "Why don't you join me? It'll save water.", Chase teased, playing with his already half hard cock. Ashley and Lilith immediately agreed and quickly stripped naked before getting into the shower with him.

Quickly, the three of them began kissing and feeling on each other, as Chase's cock quickly hardened to its full 8 inches. Ashley and Lilith immediately got on their knees and gave their friend a double blowjob, with Ashley focus on his cock as Lilith helped herself to his balls, though every once in a while they would switch which part of Chase's junk they sucked and slurped on. Chase himself enjoyed it, moaning out, "Fuck that feels good, guys. Don't stop". Indeed, neither of them felt like stopping at all, hoping to coax Chase's load out of him.

They wouldn't have to wait much longer as Chase moaned and came, spraying cum onto his friends' faces, which they lapped up off of each other hungrily before the shower water washed it off. The two girls got up and bent over, putting their hands against the wall, shaking their asses to invite Chase to fuck them. Chase decided to start with Lilith, but rather than her ass, he went into her pussy. Normally for these things, he'd take Ashley's pussy and then Lilith's ass, but he decided to switch it up. Lilith seemed to appreciate it, if at all indicated by her moaning happily as Chase hammered away at her pussy. The plus-sized goth's cunt was often neglected in favor of her asshole, due to what a fat and juicy ass she had, so her pussy was rather sensitive, making it feel all the more enjoyable to take a cock there. "Ah, ah, ah, ah! Harder, Chase! Harder!", Lilith moaned out happily, forcing her butt back to take more of him. Chase happily obeyed, pounding her pussy with all he had. Even if he wouldn't be fucking her ass this time, Chase still enjoyed seeing Lilith's huge booty jiggle about, showing that by repeatedly spanking her, making her cry out with every rough smack to her enormous butt cheeks. Not wanting Lilith's asshole to be totally neglected, Chase started to finger it, making her shriek in joy even louder. Ashley remained bent over but snaked a hand down to finger her pussy to the sight of her friends fucking, eagerly awaiting her turn.

That turn would arrive with a loud moan from the duo next to her as they came, Chase blowing his load into Lilith's tight pussy, which gushed around his 8 inches. Chase quickly pulled out, letting Lilith sink to the shower floor, letting the cum leak from her pussy and down the drain, and he stepped over to Ashley's slightly smaller but still plump backside. Giving said backside a smack, making the tomboy squeal in delight, Chase forced his still hard cock into Ashley's asshole, making her shriek with joy, which only got louder as Skylar got to work.

"Ah, ah, ah, ah! Fuck that's good. Fuck my ass, Chase! Don't hold back!", Ashley moaned in pleasure as Chase pounded her ass. He was more than happy to do so, hammering at the tomboy's rectum with all his might, not at all going easy on her. Taking things up a notch, he grabbed her hair and yanked on it with one hand, and using his other hand to finger her pussy, making Ashley's screams get louder and louder, but clearly having the time of her life. He let go of her hair and began spanking her, getting even louder shrieks. It's honestly a miracle the three of them haven't had any noise complaints before. No longer content to be left out, Lilith got up and bent over to lick both Ashley's asshole and whatever of Chase's cock wasn't inside of it, and clearly both of her friends appreciated the attention.

Eventually, Chase forced himself balls-deep and came inside of Ashley's asshole, flooding her bowels with his cum and making her moan loudly as her pussy gushed out. Pulling free and satiated, the three of them focused on actually getting clean, and once cleaned up, they left the bathroom and left for their own bedrooms, going to bed already excited for when morning came and they'd get to play again.

Chapter 9: I Think I Found Myself A CheerleaderSummary:Ashley and Lilith surprise Chase with a cheer show, with a special ending.

Notes:Edit: I've finally settled on calling the male in this story Skylar. It's a cool name, and could fit for if I decide go for the rewrite of making him a femboy.

Chapter TextChase sat in his room scrolling through his phone, bored out of his mind. As he contemplated finding something to do, in came Ashley and Lilith. He wasn't surprised to see them, but was surprised to see what it was they were wearing. They were clad in cheerleader outfits, with Ashley's red and white and Lilith's black and purple, but extremely skimpy cheerleader outfits, with very tight tops that left a great deal of underboob showing, and extremely short skirts that may as well have been really wide belts, along with very tiny thongs underneath, very visible from both the tops and bottoms of their skirts.

Chase struggled to find his voice, and when he did he merely asked, "What are you two wearing?". Lilith spoke first, saying, "To start, for an IT guy your computer password should really be more secure. Anyway, Ash and I found a huge folder of cheerleader porn, so we figured, why should you settle for jerking off when we can give you the real deal? That's what friends with benefits are for, right?". Chase felt he should be a lot more upset with his roommates for invading his privacy like that, but right now, seeing them in their tantalizingly slutty approximations of cheerleader uniforms made him less angry and more horny. Seeing the bulge in Chase's boxers, Ashley and Lilith knew that he was on board, so they decided to get to work.

The two girls put on the sexiest cheer routine they possibly could, bouncing their tits, shaking their asses, and gyrating their hips this way and that for their friend's viewing pleasure. Even with Lilith's rather heavy-set frame, she was still able to keep up with the much sportier Ashley. Chase was certainly enjoying the show, if at all indicated by the straining bulge in his boxers. This did no go unnoticed by the girls as they shook their pom poms and their asses around. Taking it up a notch, they took turns sitting on Chase's lap, rubbing their plump behinds into his crotch. "You know you can touch if you want", Lilith said, an invitation Chase happily accepted, squeezing and sometimes smacking Lilith's fat juicy ass, and doing the same for Ashley when she took a seat.

Eventually the girls got insanely horny, as indicated by how utterly drenched their tiny thongs now were, so they decided to move onto the good stuff. "Since this was my idea, I'm going first!", Ashley said, moving her thong aside and roughly plopping down onto Chase's cock, riding it with reckless abandon. "Ah, ah, ah, ah, fuck that's good!", Ashley moaned out happily as she bounced herself with everything she had. No longer content to merely watch, Lilith discarded her own thong and stepped in front of Ashley to smother the redheaded tomboy with her fat bottom, making her eat out her tight holes, which Ashley was more than happy to do, feasting on the chubby goth's holes as if they were her last meal.

This went on for a while until the three could take no more and came in a chain reaction, with Lilith's pussy squirting in Ashley's face, Ashley's pussy squirting on over Chase's cock, which then fired a load of cum into Ashley's slit. Untangling from this set up, Ashley laid on her back on the bed, inviting Lilith to eat out her cum-filled pussy, an offer she gladly accepted. As she did this, Lilith pointed her huge bottom in the air, so Chase knelt behind her and spread her enormous buttocks to reveal her tight pucker, which he immediately sank his cock into, quickly establishing a rhythm of roughly pounding Lilith's ass, often spanking and smacking her thick jiggly booty, making the goth moan in Ashley's pussy, adding on to the pleasure the tomboy felt.

After enough of this, the three friends reached their limits once again and all came, with Ashley's cunt gushing in Lilith's face, Lilith's pussy gushing over Chase's balls, and Chase firing a load into Lilith's rectum. As they untangled themselves, they cuddled together, with Ashley eventually saying, "Hey man, sorry again for going through your computer, but if there's any fantasies you want to live out, you can just tell us instead of settling for jerking off." Chase replied, "I'm over it. Besides, this did spice up an otherwise boring afternoon." Lilith said nothing, already sleeping off their latest romp, with her roommates soon joining her.

In his dreams, Chase was already thinking of what fantasies he'd like to share with his friends once they woke up.

Chapter 10: Hit 'Em With Your CatwalkSummary:Chase has a secret crossdressing kink that Ashley and Lilith happily support.

Notes:So a few things:

1. I've finally settled, no more changes, the male will be called Chase.

2. I'd been bouncing back and forth on making Chase a femboy, but decided not to do it full-time, so I just did this as a one off. If you'd like to see more crossdressing Chase chapters, drop a comment.

3. The title is pulled from a song by RuPaul, keeping with the crossdressing theme.

4. Lastly, NGL, I got a bit lazy on the final round of sex near the end.

(See the end of the chapter for more notes.)

Chapter TextChase wasn't sure why he agreed to the bet with Ashley and Lilith, but he ultimately lost the game of Smash Bros they'd played, so now he had to cross-dress for the two of them, whether he liked it or not. He'd actually had a bit of a curious about it, so he figured it wouldn't be the end of the world.

One day, Ashley and Lilith had called on Chase to fulfill his end of the bet, and eventually he came out in a fairly slutty outfit. A tight belly shirt with an open jacket for the top, and on the bottom a very short skirt that did little to hide some colorful panties. Ashley and Lilith clearly enjoyed the sight, cheering for their friend and taking pictures with their phones, enjoying the view of him twirling and bending, his tight(and admittedly girlish) behind on full display.

"Beautiful Chase, just beautiful!", Ashley said, to which Sky just shrugged and smiled at them. "Your little display has gotten us worked up", Lilith said, "and it looks like we're not alone", noting the large bulge in Chase's panties, which he tried to pull his skirt down over. Before he knew it, the girls tackled him and pinned him to the bed on his back, their bottoms rubbing into his crotch. "We better do something about this", Ashley noted, to which Lilith nodded, and they moved down and removed Chase's panties, revealing his hard and big dick.

Ashley focused on sucking off her fuck-buddy whereas Lilith took a different approach, the goth finding Chase's asshole and licking it, making him cry out. Chase didn't play with his asshole all that often, so it was very sensitive, luckily for Lilith, it was still clean, making it enjoyable to lick. "Don't give me that look, Chase", Lilith said, "you've pounded my ass and Ash's so many times, it's only fair we get a turn with yours every once in a while." Chase wasn't even complaining, this all felt very good, and he knew he wouldn't last much longer.

Indeed he wouldn't and with a loud moan, he came, filling Ashley's mouth with his spunk, which she gladly gobbled up. "Don't think we're done yet", said the tanned tomboy, "we've got something special planned for you", the two girls running off and coming back wearing their signature strap-ons. Sky knew exactly what they had in mind, and knew he couldn't stop it if he wanted to. Ashley, with a devious grin, said, "You wanna dress like a girl, we'll treat you like a girl!", and without warning, the girls spit-roasted him, with Lilith in his ass and Ashley in his mouth.

The two girls held nothing back as they pounded their friend with their respective strap-ons. "Fuck this is good!", Lilith said, to which Ashley replied, "Agreed. We should've pegged him a while ago, give him a taste of his own medicine." "Sometimes I wish we had real dicks so we could actually feel being inside of his holes", Lilith said in response. Strap-ons get the job done, but it's often hard to compete with the real deal.

Eventually Chase could take no more and he came, spurting cum all over the place, and the girls came on the ends of their straps that were within their pussies. Pulling free, the two of them discarded their strap-ons and bent over the bed, sticking their bubble butts up in the air. "We used you like a whore, now return the favor!", Lilith said, the chubby goth shaking her thick rump, side to side. Quickly, Chase brandished his still hard cock and fucked his two friends, going back and forth between the girls and their lower holes, leaving load after load in each pussy and asshole, to their delight.

They eventually got on their knees for his final round of orgasming, spraying half of his final load on Ashley's face and the other half on Lilith's, the goth and tomboy kissing and cum-swapping as they slurped up his spunk. After this, the three of them cuddled on the bed, with Chase saying, "That wasn't as bad as I thought". "Told you you'd like it", Ashley said. Lilith spoke up next, saying, "Maybe you should wear girly clothes and let us peg you more often", to which he replied "Don't count on it, Lil". With that, the friends all fell asleep, knowing that they'd play again once rested.

Never before had Chase been so happy about losing a bet.

Notes:If this doesn't work out, I have another story in the chamber with a full-time femboy bottom and his futa tomboy top girlfriend.

Chapter 11: Ocean Man, Take Me By The HandSummary:Ashley, Chase, and Lilith spend a day at the beach.

Notes:(See the end of the chapter for notes.)

Chapter TextIf there was one thing about summer that softened the blow of the excruciating heat, it was spending time at the beach. Chase and Lilith would normally prefer to stay in their air conditioned apartment, but Ashley talked them into it. Ashley was clad in a red and actually fairly conservative bikini, covering a good deal of her breasts and butt, so she could keep up her tanning pattern, and Lilith wore a black and purple string bikini with skulls on them, normally nothing special, but it looked smaller on her somewhat chubby frame, the bottoms being all but devoured by her ass crack until they looked like a thong. Chase wore some simple trunks patterned after Spider-Man, one of his favorite superheroes, and staring at his friends made those trunks grow increasingly tight.

The three friends set up their site in a secluded area of the beach far away from most of the public, so no one could see what would inevitably occur, and they had their fun. Lilith stayed on a chair reading some dark romance books off of her phone, as Ashley and Chase frolicked in the nearby sand and water. "Come on in, Lil! You can read all you want at home!", Ashley called out, and eventually Lilith caved in and joined her roommates' splash fight in the waters around them.

The girls returned to their resting areas when Lilith pulled out some sunscreen and said, "Hey Chase, care to lotion me up?", turning over onto her stomach to show off her enormous ass. "Gladly", Chase said, quickly smacking the goth's huge butt cheeks, making them jiggle and Lilith herself squeak, clearly enjoying the spank. Chase slathered the protective cream all over Lilith's heavy set body, paying extra attention to her huge tits and fat ass, not that Lilith had any problem with that, indicated by her wet pussy bleeding through her bottoms. Ashley called him over to give her the same treatment, which Chase happily did, much to the delight of them both.

Of course, feeling on such gorgeous girls made Chase grow hard, which they quickly took notice of. Before Chase could say a word, they made a move to remove his trunks, his fat cock freed. In seconds, Ashley and Lilith began giving the man a double blowjob, taking turns going back and forth between his cock and balls, making him moan in joy. "Fuck that feels good, guys", Chase moaned, already aware he wouldn't last much longer.

Indeed he wouldn't, as he let out a moan and spurted a fat load onto his friends, who eagerly gobbled it all up. From there, Chase got onto his back and Lilith moved her bikini aside to reveal her pussy before roughly dropping her huge ass down, her tight slit engulfing Chase's huge cock. "Ah, ah, ah, ah!! Fuck that's great, Chase! Don't you fucking stop, ever!", Lilith moaned as she bounced herself on his cock, giving him a great view of her fat ass jiggling around, which he started spanking, much to the goth's delight. Ashley, tired of being left out, bent over to place her smaller but still very ample bottom in Lilith's face, inviting her to eat her out, an invitation that she happily accepted.

This went on for a while until the three of them reached her limit and Chase fired his load into Lilith's pussy, which gushed around his rod, and Ashley's pussy squirted into Lilith's face. They untangled with Lilith getting on all fours, offering Ashley to eat the cum out of her slit, which Ashley does without hesitation. This places the tanned tomboy onto all fours, pointing her plump ass in Chase's direction, prompting Chase to drive his cock into her tight asshole. Chase held nothing back, mercilessly pounding her ass with all his might, much to Ashley's delight, making her moan into Lilith's pussy as he ate her out, making the goth moan as well. "Having fun with her tight ass, Chase?", Lilith asked, to which Chase replied, "God yes. You may be a real butt slut, but so is this one", smacking Ashley's firm but jiggly ass, earning another pleasurable squeal from the redhead.

After enough of this, the three had enough and they all came in a chain reaction, Lilith's pussy gushing in Ashley's face, Ashley's pussy squirting against Chase's balls as her rectum spasmed around his dick, which triggered him to shoot his load into her bowels. Pulling free, they saw that the sun was starting to set, so they called it a day, gathered their stuff, and headed back to the car.

The one thing none of them were looking forward to, it's cleaning the sand out of their private areas, but for sex, that was a small price to pay.

Notes:Due to my inability to decide if Chase should be a full-on femboy, I'm considering making an AU of this fic with Chase as a femboy, and this will continue as normal with Chase as a fairly traditional male. Drop a comment if you'd like to see that.

Chapter 12: That's How A Superhero Learns To FlySummary:Ashley, Chase, and Lilith visit Comic-Con, and do I need to spell out what comes next?

Notes:There's another convention happening near me this weekend. If you're anywhere near Oaks, PA, it's Liberty Comic Con. If you're there, look for me in an Optimus Prime costume.

(Though don't mention AO3; my dad will be there with me and he knows nothing about AO3, and I'd rather keep it that way.)

(See the end of the chapter for more notes.)

Chapter TextIf there was one time of year that Ashley, Chase, and Lilith always looked forward to, it was Comic-Con. Good food, fun panels, cool if wildly expensive merch, and seeing people dressed as all their favorite fictional characters. They usually did group costumes, and this year was no different, with this year's costumes being Chase dressed as Spider-Man(traditional red and blue), Ashley dressed as Mary-Jane's web-slinger persona Spinneret, and Lilith dressed as Spider-Gwen. They were quite popular in the convention, with people stopping them for pictures, not that they had a problem with that.

In the middle of the day, the trio had taken numerous photos and carried around a bunch of merchandise, and were sitting at one of the few open tables to catch their breath. Of course, Chase couldn't help but stare at the way his roommates' costumes clung to their curves, and the girls quickly took notice of the bulge in Chase's costume. "What are you looking at?", Lilith said, gesturing to Chase's hard cock. "Sorry guys", Chase said, to which Ashley replied, "Don't be so nervous. How else should a guy react to a pair of hot girls in skin-tight outfits. Now, according to the schedule", Ashley said, pulling out the pamphlet they received at the door, "we've got some time until our next panel, so why don't we let off some steam?". Lilith said nothing, but nodded in agreement with her roomies.

They managed to slink off to a secluded part of the convention center to have their fun. Due to them being both pressed for time and where they technically didn't belong, they had to make this quick. Ashley and Lilith bent over and pulled their pants down, revealing their thick bubble butts and wet pussies, wiggling their hips to invite Chase to fuck them. Taking the invitation, Chase quickly forced his cock into Ashley's pussy, fucking her roughly. "Ah, ah, ah!! Don't stop, Spider-Man, don't stop!", Ashley moaned, unable to stop herself from referring to Chase by the name of his character. Chase didn't mind, pounding the tomboy's cunt all the harder, occasionally spanking her jiggling butt cheeks to turn them as red as her costume. Lilith, tired of being left out, got in front of Ashley with her fat ass spread to show off her puckered asshole. "Lick my ass. Get me ready for my turn", Lilith demanded, demands that Ashley happily fulfilled. The chubby goth moaned as her friend licked and lapped at her asshole, preparing her for when it would be her turn to take Chase's dick.

That time would come as Ashley, with a moan muffled by Lilith's enormous backside, came, her pussy tightening further around Chase's cock, which responded by letting out a fat load inside of the tanned tomboy's slit, and Lilith's own pussy gushed in Ashley's face. Changing gears, and noting that the clock was ticking for their next panel, Lilith moved backwards, quickly engulfing Chase's cock with her tight asshole. Chase didn't waste a second and roughly pounded Lilith's asshole with all his might, roughly spanking and smacking Lilith's massive bottom, turning the juicy cheeks as red as his and Ashley's costumes. Ashley had taken a seat in front of Lilith with her legs spread, offering her cum-filled pussy for Lilith to lick, an offer that the goth happily accepted, much to the tomboy's delight.

After a while of this, in a chain reaction, Ashley's pussy, cleaned of Chase's load, gushed in Lilith's face, Lilith's pussy gushing against Chase's balls, and Chase shooting his load into Lilith's asshole, flooding her bowels with his load. Ashley quickly ate out Lilith's rectum of Chase's load, earning one final orgasm from the goth, before the three quickly redressed and hurried to where their panel was being held, making it inside just as things were getting started.

The three friends truly loved Comic-Con, and the weekend was just getting started.