Ruby's New Experience

Story by TikTikKobold on SoFurry

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Ruby Gloom learns about Free Use and Orgies from her friends Iris and Misery, only to fall down a rabbithole to save an old theater.

This is a Ruby Gloom Fanfiction. All characters are 18+.

This is a commissioned piece. If you'd like a commission, please contact me


Life in Gloomville is grimly delightful, especially in the mansion on the hill where the ragdoll Ruby Gloom lives. Over the years, Ruby has grown into a fine woman, the owner of the estate, and quite the beauty, indeed. Despite the passage of time, she is still her chipper self.

In fact, no matter how many things have changed, so many things stay the same. Iris is still her adventurous, energetic self, and Misery is as Misery as ever. However, as one ages through adulthood, the responsibilities one acquires can mean there is less time for friends than in childhood, and Ruby goes through periods without seeing her friends. This just makes the times they do meet extravagant affairs of happiness and excitement—at least when two-thirds of the feminine trio are involved.

One day, Ruby is strolling through town, enjoying the chill air that blows in from time to time, her dress swishing with each step. Her fashion hasn’t changed much, though the curves she has acquired over the years certainly make for delightful sights to those who gaze upon her. One would be surprised to know of her dollishness if they didn’t already know her.

Though as she makes her way down the town, her eyes spot a sight of delight, for Iris and Misery are together, heading down the opposite way from Ruby. With her bubbly excitement, Ruby approaches the two with a spring in her step, waving to each of them and calling out.

Iris is the first to respond, rushing up to Ruby and giving her friend a great big hug, nuzzling up against her, and sighing happily.

Misery taps her fingers together, hunching her shoulders, looking away.

“Hey, Ruby! What have you been up to?” asks Iris.

“Not much,” Ruby admits. “The house is a bit boring nowadays, but I keep everything in working order, no problem.

“It must be really sad in there all on your own,” Misery says, perking up just a little bit.”

“It can be,” Ruby says, rubbing her chin, “But I guess that’s why I go out on these little trips of mine. But speaking of trips, what are you two doing together?”

Iris and Misery look at each other. The two old friends appear more contemplative than a simple response would allow.

“Well,” says Misery, “I don’t think you’d like it. It’s really, uh, different than what you’re used to.”

“Oh, I don’t know,” says Iris, smirking slightly. “Ruby’s always ready to try something new, right, Ruby?”

“With my best friends in the whole world?” Ruby asks, bouncing on her toes. “You bet. So, what is it we’re doing?”

“Oh, I don’t know how to explain it,” says Misery, wobbling back and forth.

“Yeah, that’s pretty tough,” Iris says, folding her arms over her chest.

“You could always just show me,” Ruby suggests. “I’m a quick learner, after all.”

The two friends look to each other once again, Misery frowning deeper than before and shaking her head. “Sorry, Ruby, but no, it’s not something you could just jump into without a proper discussion first. It’s not exactly, uh, safe.”

“You’re doing something dangerous? What are you taking up stunt work? I could see Iris doing that, but not you, Misery.”

“Well, it’s certainly physical,” Iris says, tittering slightly.

“That’s putting it lightly, and I don’t like to put things lightly,” Misery shakes her head.

“Okay, let’s put it like this, Ruby. You know the new shop that opened up last month.”

“Of course,” says Ruby, hands on her hips. “I make sure to know all the goings on in Gloomville.” She adds to a slight scratching of her cheek and adds, “Though, I haven’t really looked into what kind of business they were, or even what they’re called… or where they are.”

“Oh, Ruby, Ruby,” Iris says, draping an arm over her friend’s shoulder. She flutters her eye and shakes her head. “It’s an adult entertainment store and theater.”

“Adult?” Ruby responds, blinking. “What’s so adult about it?”

Iris rolls her eye, grabbing Ruby by the hand. “Come on, I’ll explain along the way. You’re not doing anything, are you?”

“No, not really,” Ruby says, led on by her old friend. Misery takes up the rear, sulking as she follows the two.

“So,” Iris begins, her step light as she heads unabashedly through the streets to their saucy destination. “By ‘adult entertainment,’ You know I mean ‘sex,’ right?”

“Oh? Ooooh!” Ruby gasps. “I mean, yeah, of course!”

Iris shakes her head, sighing. “Well, they have a special section there. Ever hear of something called ‘Free Use?”

Ruby shakes her head.

Misery is the one to speak up this time, sniffling slightly to announce her presence. “It’s where someone gives up all of their autonomy and lets their body become the plaything of any number of total strangers. They will ravage you however they wish, and you have to take the whole thing.”

“Yeah,” Iris says, shrugging. “Misery and I have been going a few times a week for the last month or so. It’s an excellent way to burn off the excess energy.”

“Or to get thrown about and used and abused,” Misery says.

“Only if you sign up for that,” Iris says. “There are still rules there to make sure people are still having fun, after all.”

Ruby clasps her hands to her mouth. “Oh, wow, well, no wonder you were taking so long to get to the point.”

“Yeah,” Iris says, stopping. She lets go of Ruby’s hand and smiles apologetically. “So, if it’s not something you’re interested in, we both understand.”

Ruby stands there for a moment, her head hanging low. The two friends look to each other apprehensively, but she smirks and lifts her head, smiling with her Ruby Gloom smile. “Sounds like fun. Let’s go!”

The three companions travel through the town, arriving at an old theater where the sex shop has set up its wares. As they passed through the entrance, Iris waved happily to the clerk stocking up on various toys and the like, and he waved back with a chipper smile and a “how do you do?”

“Wow, people here sure are friendly,” says Ruby.

“Why wouldn’t they be?” asks Iris. “They’re all here to have fun, after all.

“I guess you’re right,” says Ruby. “So, where is this all going down?”

“Back here,” Misery says, pointing to the back of the shop with her sleeve. The three of them make their way back there to what was once the main stage. Passing through the door was like being transported to a whole different world, as Ruby's senses were immediately filled with the coppery smell, the heavy, musky air, and the sight of many bodies writhing around. She’s basically paralyzed as she stands at the entryway, blinking to make sure she is seeing what she’s seeing.

“Something the matter?” Iris asks, and when Ruby turns to look at her friend, she immediately blushes, as Iris had already lifted her shirt completely off, showing off her whole upper half, tits and all.

“I… I just never saw anything like this,” Ruby admits.

“Aw, come on. The first time is always the weirdest,” Iris says, grabbing Ruby by the hand. “You just need to come over and get used to things. Here, I’ll show you.”

Iris leads Ruby away from the door and deeper into the orgy before them. She waves and leaps in the air, her tits bouncing for all to see. “Yo, everyone! Iris and Misery are here, and we brought a friend today!”

Many of the partiers lift their heads from their copulations to give Iris a friendly smile and wave, their eyes locking onto the three women as they make their way to the center.

“Now, it’s really easy. You just have to make yourself available to anyone and everyone, and you’ll have fun.”

“It seems so strange. What if someone tries something… I dunno… harmful.”

Misery perks up and scoots in. “Oh, I hope they do,” she says, shuddering. “That’s the best part, after all.”

“Aw, don’t you worry about that. Everyone is friendly here,” Iris says, hooking her hands to her leggings and pulling them down. “Here. I’ll show you.” This leaves her only in her stockings as she leaps onto a mattress, wiggling her butt. “Come and get it!”

It isn’t long before one of the random people shows up. To Ruby’s surprise, it is another woman who approaches Iris. The stranger gets down on her knees and buries her face right between the cyclops’s cheeks, the loud sounds of slurping and sucking audible even in the cacophony of moans and groans happening all around them.

Blushing slightly, Iris blinks up at Ruby with a smile. “See? It’s that easy.”

Iris moves her hand behind her, grabbing the woman by the back of the head, and she pushes the stranger in. “Come on, that’s the good stuff, get deep in, ha, there. Right in my.. Yeah, my ass!”

Ruby clasps her cheeks, and she can’t believe it when another woman approaches Iris. This one stands on the mattress in front of her and pats Iris on the head. She turns around and dives right in between the woman’s thighs, her own eye closed and her tongue slurping up and down along the woman’s already aroused slit.

“Oh… oh wow,” Ruby gasps, watching the scene before her. “Look at her go. And with so many women. I never thought… I mean, I knew, but…”

“Iris really is popular with the ladies here,” says Misery, and when Ruby turns to see her other friend, she has to gasp as well. Misery has removed her dress and stands before the ragdoll with fingerless sleeves and a choker. The shape of her friend’s body is like that of an incredible model. Ruby can’t help but clasp her hands to her mouth, her eyes sparkling. “Misery…”

“What?” asks the perpetually crying gal. “Is something wrong? Oh, please tell me there is.”

“It’s not that,” says Ruby, gulping and pulling her hands away. “It’s just that… you’re so beautiful.

Misery pokes her index fingers together. “Oh, well, you don’t have to be like that,” she says. “I’m not here to receive praise, you know.”

“But it’s true!” Ruby says, placing her hands on Misery’s shoulders. “I haven’t seen someone as beautiful as you before. I… I don’t know what to say about it.”

Misery places her hands on Ruby’s sides and gives her a tiny little shove. “Well, there’s one thing you can do about it,”

“Huh? What’s that?”

“Why don’t you dress down yourself and find someone to have some fun with, Ruby?”

Ruby coughs. “Right now? I thought maybe I’d watch you two first.”

“You like to watch?” Misery asks. Meanwhile, Iris groans happily, wiggling her butt against one woman’s face while she eagerly tongues the second woman.

“I… Well, maybe I do,” Ruby says, hands on her hips. “Is there something wrong with that?”

“I guess not,” says Misery, looking around. “But I don’t know if you’d like to watch what I have coming for me,” she says.

Ruby frowns. “Why’s that?”

Misery blinks, and then she leans in closer to Ruby, and then she whispers, “Because when it comes to me, things can get really rough.”

“Rough?” Ruby asks.

Just then, her questions were answered when a strange man walks by, grabbing Misery by the hair and yanking her away from Ruby. Misery yelps and stumbles backward into the man’s grasp, and he wraps his arms around her, groping at her chest and leaning in, going for her neck.

Misery closes her eyes, tilting her neck to give him access, sighing as she seems to disappear from the world as she’s being used.

This leaves Ruby alone between two friends who are having the time of their lives. And what is she to do about it?

Watch, she supposes.

And watch Ruby does, finding herself a seat by one of the walls, the ragdoll sits down, hands on her knees, looking over to her friends to see exactly what it is the two of them would be doing in this little free-use orgy.

First is Iris, who pushes up from her position, licking and enjoying the fruits of the labia of her nameless partner. She stands up. She flutters her eye and drapes her arms over her front partner’s shoulders, leaning in and kissing her. It’s a slow and passionate thing, with lots of tongue rolling around this way and that.

Ruby bites her lip as she watches, pushing her legs together. In all her years living in the mansion, she had never thought of her friends in a sexual light before. Perhaps that was because they knew each other since they were young, but now Ruby sees Iris just going for it, making out with this random stranger, and she can’t help but realize… Iris is HOT.

Iris pulls back, saliva bridging between her and her partner. She licks her lips, and then she goes back in, whispering something into the woman’s ear before pulling back and going in for her mouth again. But this time, Iris doesn’t kiss her. No, she gently grabs the woman’s lower lip with her teeth and rubs between them, nibbling gently and pulling back possessively. When she lets go, the woman’s lips snap back into place, and the lady lets out a low, needy moan.

Iris’s attention goes lower, nipping at the woman’s neck, gripping her chest, squeezing and groping the tit as the woman pushes herself forward, letting more of her body be pressed by that hand, her nipple rubbed by Iris’s palm.

Ruby crosses a leg over the other, and she leans in, watching with much more intention than before.

Iris continues her trip down, kissing along the woman’s collar and going lower, making little pecking marks down the mound of her chest before wrapping her lips around the woman’s tit. She suckles on it, looking up with that large eye, giggling a little as she watches the woman, who stares back with hypnotic delight on Iris’s face. The woman reaches out to place her hands on Iris’s head, but Iris grabs those wrists and pulls her down, shaking her head. The cyclops breaks her connection, letting the tit bounce back into place, and says. “No, no, I’m in charge, pet.”

The other woman, who had been pleasing Iris, whimpers slightly, waiting for the woman to return her attentions to her. And Iris is not one to disappoint. She pushes her hips back, thrusting her butt into the woman’s face with enough force to knock her back.

The woman lies on the ground, dazed, blinking, only to gasp when Iris’s rump finds its way to her face, sitting on her, rubbing up against those lips, letting the nose poke up against her butt as her pussy lips kiss the lips on the woman’s face.

Iris then pulls her first pet close to her, making the woman straddle the other one on the ground. Iris leans in, kissing the woman’s labia, shuddering and giggling slightly before she spreads her lips and presses her tongue to the woman’s pussy lips and strokes up, and down, and up and down.

Ruby squirms in her seat, glancing around this way and that really quickly. Out of all the people here, she is the only one still dressed. She is the only one not touching anyone else or themselves.

And quite a few people are touching themselves here, watching the scenes play out before them, and stroking and fingering. It’s perfectly normal. It’s perfectly acceptable, and it’s perfectly driving Ruby crazy.

That’s when she slides her fingers down over her sides and down her thigh. That’s when she hooks her skirt and pulls it up. That’s when she presses her fingers between her legs and up against her panties, already slightly damp. She sighs, rolling her fingers over herself, not going inside, but just sitting right there, through the cloth. That shouldn’t be too much to start, should it?

Ruby leans back, her fingers swirling faster and faster as she watches Iris continuing her slow turn to control the two women. Iris leans forward, her mouth open wide, locking in to the woman’s pussy. No doubt her tongue was swirling deep inside there, as the woman writhes and sighs, running a hand over her head and rocking her hips forward.

The woman on the bottom is having a good time too, as Iris grinds her hips against her and leans forward, fingers walking down over her navel and beyond, dipping into her folds, curling up and flickering over the lips and inside.

Ruby thought this place was only for people to be used by others who were here, but it’s much more freeing than that. Everyone is having fun how they want, and they are giving pleasure to each other in ways that they desire. There’s something quite delightful about that indeed, and as the ragdoll girl gasps and rocks her hips, rolling her fingers over herself, she begins to realize that there’s something simply magical about the idea of “free use.”

But curiosity has her overwhelmed. She’s been watching Iris for so long that she’s neglected checking out Misery. So Ruby’s eyes flitter over towards where her friend was, and when she stops and sees what’s going on, she can’t help but let out a loud and surprised gasp!

They say that Misery loves company, and it certainly seems that way from the number of men and women that surround her, hardly giving Ruby a chance to see her. Through the wall of bodies, she can see some glimpses of the events transpiring on her constantly crying friend.

She’s pinned down to the floor, with one man sitting upon her naked stomach, his hands clamped around her throat. Misery tilts her head back, offering up more of her throat to the choking dominant while another guy looms over her, sitting on his knees. He thrusts his thick and veiny cock forward, slapping her across the face, making her wink as he almost hits her in the eye, but he finds his way to her parted lips, thrusting through into her. With grunting thrusts, this stranger fills up her mouth and pushes past to her constricted throat, where her walls cling tightly to his length. The force of his thrusting is enough to bounce her breasts as he reaches forward, grabbing her by the hair and clinging tightly to her locks, using her strands like handlebars as he bulges out her throat against the other guy’s hands.

The man sitting on her lets go, and when he does, the bulge of the cock in her throat is enough for Ruby and the others watching around Misery to see, cheering as she is choked by the massive dong filling her throat.

But Misery takes it, her hands pinned against the ground by others, and her legs spread by more people still. She can’t move, but would she even want to move? She seems so tranquil down on the ground, even with so many other people holding her and a guy on top fucking her so hard, she probably can’t breathe.

Only when he is delighted, groaning and letting his cum shoot out of his cock does the man pull out, allowing the jizz to streak down her face, much like her tears. He stumbles up to walk away from her, letting the next person come up and take her.

That’s when someone walks up to her and wraps a leather collar around her neck. They tighten the thing as far as they can, cutting part of her airway off as they hook the thing through the loop. Attached to the collar is a leash, and the stranger yanks her up, forcing her to sit, then crawl. She chokes and coughs up the cum from her previous paramour, the stuff trailing between her arms and legs as she crawls and follows this new lover to this person’s strange whims. There, they take her to a semicircle of lined-up men, their cocks out and ready, and they yank her to sit up on her knees, right in front of those wonderful and pulsating things. Another tug pulls her up against the cock, squishing the thing against her face as her lips kiss his balls. Groaning, her eyes roll back as the other two grab onto their shafts and slap her across the face, sending her turning her cheek one way and then the other, shaking her head as they bounce her back and forth against the clapping cocks.

Soon, though, Misery wraps her lips around the cock in front of her, reaching up and grabbing the two on either side of her. She strokes, and she sucks, closing her eyes and finding herself in the vibe of going through the motions, pleasuring others while they pull her and tug her and strike her with meaty members.

Ruby stares the whole time, transfixed. How could Misery enjoy being used like a piece of meat? This is such a different version of Free Use than what Iris had shown off. Even so, she still sits back, and she still swirls her fingers over herself, but she lifts her dress higher, her hand moving underneath, fondling up to her breast and playing, her breath heavy as she stares at how the men are handling Misery. Would she want to enjoy that as well? Or is she more interested in seeing Misery inflicted with such tortures? Would she want to inflict them herself or be inflicted by them? The possibilities branch in many directions, indeed.

Misery pulls her mouth free from the cock, coughing as the spit and mucus-heavy dick glistens outside of her face. The leash pulls her tighter to the man, up against his balls, where she takes a long and deep whiff, shuddering at the scent of unwashed musk. Oh, how the men who don’t shower before they come here smell, indeed!

But the three she tends with hands and mouth are not the only ones who play with her, as another figure approaches her, pulling out the tip of a marker and pressing it against her supple flesh. “Whore,” they wrote on her arm, and that was only the first of the markings that people would give her, as more and more approached her, pressing marker to flesh, pressing in permanent sentiments throughout. “Free Use” “Cum Toilet” “Baby Maker” “Toy.” There is no end to the things being said about her by the markers and the people making the markings, until her body is a canvas of marks.

And as they all move back from her, admiring their work, that is when the three men all cum at once, cascading cum over her face, marking her with the pearly whiteness that runs down her face like her tears. But as she sits there on her knees, naked and marked by cum and ink, Misery is smiling, enjoying herself, and panting heavily.

Ruby sits there, watching the whole scene. The whole thing makes her push her fingers under her panties, rubbing at her lips directly.

It’s so beautiful… It’s so hot. It makes her want to join, but what would she do!?

Now is the time for her to find out.

Ruby wonders how she might get in on the action. After all, she doesn’t know the etiquette of these sorts of situations. One simply can’t just walk up and have their way with someone else without so much as a “hello,” right? Misery and Iris have been here before. That much is definitely true, so they would have met the men and women here and gotten to know them beforehand.

But it is called “Free use,” which implies that there is no talking and that things are as simple as she believes.

Either way, she still watches Misery, getting slapped on the ass and lifted by some strong man who buries his face in her butt. The sheer forwardness of it is part of the charm, or perhaps it is all of the charm. Either way, it makes her play with herself, rolling her fingers over her clit and groping her chest, letting out huffing and panting breaths as she looks side-to-side to her two friends and their partners. It’s enough to motivate her to keep going.

But her view is obstructed when two men approach her from either side. They are tall and naked, and they hold smiles over their partially shadowed faces as they watch down at her.

“Oh… oh, hello,” Ruby says, pulling her hand from between her legs and the other from out of her dress.

The first man steps forward, placing a hand on her thigh. Ruby stares down at it, her heart thumping at the sight and the feeling and the warmth that strokes against her smooth skin. She licks her lips and takes her hand, placing it on top of his and sliding it up over her thigh, higher and higher.

He steps back, ushering her to the soft floor. She gulps, and she scoots off her seat, sitting down and looking straight into his obscured eyes. He leans in, pressing his hand tight against the upper regions of her thigh and pressing his lips to hers. With a soft exhale, she takes the kiss, parting her lips and letting her tongue play with his.

That’s when the second man walks up. He has a hand on his hip and the other holding up his cock. The thing is meaty and long, and it bulges with the blood that pumps through the veiny thing, ready for attention. And with it right by her face, it seems she’s the one giving it that attention.

Ruby pulls away from the first man, placing a hand on his cheek and smiling softly before she turns to face the other man and his waiting member. Her lips press gently against the tip, taking in the slightly salty taste as she reaches up and grasps the base. She then kisses along the shaft, stealing furtive glances up at the man, testing herself, seeing if she is in fact doing things the right way. From his slight sighs and groans, she thinks she’s doing quite all right.

The first man doesn’t sit idly by, however, and he slips down over her body, hands trailing down her sides and to her thighs, hooking over her panties. He pulls them down, slowly rolling them over her legs. She lifts them, allowing him to get them down lower and lower, undoing them over one leg and letting them dangle on the other.

While he does this, Ruby opens her mouth wider and takes the cock into herself, tasting the slightly musky thing and the remnants of other women that it had been in during the night. Her eyes flutter back as she sinks her head lower against the shaft, letting the thing fill up more and more of her mouth. She lets out soft sighs as she sinks into it, closing her eyes and making a slow, deliberate motion up and down along the shaft, taking it in deep and pulling it out, letting it glisten in the light of the room.

Between her legs, the man dives in, kissing her thigh, up and up and up until he gets to her love nest. There, he rolls out his tongue and slides it up and down along her slit, letting it make her tremble as it slinks up and down along her labia before finally pushing in.

His whole face presses up against her, his nose against her clit, the thing pointed and rubbing against her and providing extra stimulation. It is unlike anything she had felt before.

Surely, Ruby knew what sex was. She wasn’t that much of a shut-in. She had been taught that it felt good, and sometimes even fantasized about what it would be like to do it with someone she cared about. But here she is with two strangers. No, these aren't total strangers. These are her fellow Gloomville inhabitants. They are her neighbors and potentially new friends.

And indeed they are pretty friendly with mouth and cock pleasuring her. She flutters her eyes open to smile up at the man above her, feeling the pulsing of his cock inside her and anxiously anticipating the end of his ride. Soon, though, she feels it. It comes as a slight pulsing and quivering. It comes as an anguished grunt rising from his throat. It comes as warm, salty stuff that touches her tongue. She pulls back, letting it strike her on the face, oozing down her cheeks and onto her dress, all the while grinding up against the other guy, letting her own climax build up as she holds onto the flattening member in her hand.

Ah, yes, to see him fall to his knees in delight as the other plays with her, making her squirm, making her squeal. It is something she hadn’t thought she’d do.

And now, she begins to wonder if there is more she can do, and, if so, how far she can go with the discoveries she has about herself?

The man at Ruby’s mouth pulls away, satisfied with his cock dripping with the delight that she so graciously gave him with her throat. He slips away from her to join some others in a more relaxing atmosphere as his refractory period begins.

This leaves Ruby alone with the man between her legs. He pushes himself up, his cock hard and ready for her, flopping from between her lips, rubbing teasingly against them, and landing on her pubic mound, dripping with the precum that testifies to his virility.

Ruby stares down at the sight before her, biting her lip at the presentation.

She’s distracted a moment as a cry of pleasure in a familiar voice turns her and her partner’s gaze away. Iris leans forward, hands on the wall, closing her eyes and blushing deeply. Her tits bounce, and she rocks her hips back as a brawny woman stands behind her, spanking her playfully and thrusting forward. Around her hips, the woman wears a strap, and a brightly-colored dildo plaps its way inside the cyclops, its rainbow stripes nearly hiding the bumps and ridges that it has to add to even more stimulation than a cock can provide.

But can such a thing really compare to the throbbing, twitching warmth of the real thing? Ruby wonders this as she watches, and she brings things to the forefront when she wraps her legs around her partner, pulling him in close. He falls forward, hands on the back of the chair she sits upon, hands gripping at the piece of furniture as his hair falls over his eyes, tickling at Ruby’s cheeks.

Ruby rubs the cock up against her lips and her mound of Venus, letting that thing pulsate and squirm on her white skin and red trim before she lets her legs go just a little bit and allows him more movement.

He takes the opportunity and slips his cock back, slicking the slimy cum down along her mound and pressing against the slick lips that are waiting for him.

And they accept his cock, sucking him in with their wanting, glistening. The lubrication that Ruby built up over his dutiful tonguing was only just a little bit earlier.

The man huffs and groans, and she reaches up, brushing her hand over his cheek, smirking at him and whispering in a divine voice, “You’re doing great,” she says, pushing herself up and pressing her lips against his.

There’s an electric spark that comes with the connection, and the man dips down, his lips spreading, his tongue diving down into her. She can taste the tang of her pussy and probably the vaginas of other women in this establishment, mixed with the meatiness of his tongue and the sheer virility of his spit. She can’t help herself but return the kiss in kind, giving him an unprecedented look into the previous man’s ejaculation into her.

Despite that, or even because of it, he continues to kiss her, pulling his cock back and thrusting it into her, going in deeper into her folds.

She gasps into his throat, her eyes rolling back, her body squirming about underneath him. It’s so warm and so full, and so twitchy within her. He wraps his hand around his cock, sucking and rubbing over him as she rocks her hips against him.

Meanwhile, Iris opens her eye, smiling as she watches Ruby going on with the guy, but it turns into a quick smirk. When she speaks, it’s peppered with the gasps of having the dildo shoved up her body, distorting her stomach with each thrust of the strong woman behind her. They are so close to one another that she speaks up, and Ruby snaps her attention over toward her cyclopic friend.

“Hey, Ruby,” Iris gasps. “Look at you. Seems you’re getting the hang of it, but you’re really doing some lightweight stuff, you know?”

“L… Lightweight?” Ruby gasps back, wrapping her arms around her paramour’s shoulders, pulling him in close. They had broken their kiss, and he now dives into her neck, making her tilt her head over towards Iris. “W… what do you mean?”

“Nothing, ha, much, mmm, j-just you’re really, ah, vanilla. We gotta, haa, train you up!”

Ruby pulls the man in, forcing him deeper into her. “Train me? Oh, I don’t think so. I’m doing just fine, ah, right now!”

“S… suit yourself!” Iris replies, scratching the walls. “B… but there’s more here than just… ge-getting a fuck. It’s… mmmnah… filled with so many opportunities!”

Ruby nods, her blush growing on her face as she gets closer and closer to her own climax. “W-well, I have to thu-thank you and-and Misery, w-wherever she is,” Ruby says, “For, uhnnh, helping s-show me something nuh-new!”

Ruby squeezes the man tight, digging her fingers into his bare shoulders and having a vice grip around his hips. His own groans fill his needy kissing and suckling on her neck, and go in tune with the thrusting that goes on inside her. He’s like a possessed beast, taking her with only the need to breed deep in his mind.

But speaking of breeding, is it relatively safe for him to cum inside her? Her mind is so foggy right now that the idea disappears in a puff of smoke, but she loosens her grip on him, letting her legs fall to the floor and allowing her hips to get battered by his unrelenting thrusting. If he was going to cum anywhere, it’s going to be his idea where that’s going to be.

And that thought is quite exciting all in its own right.

Iris scoots over just a little bit, the pounding in her not relenting, but she whispers to Ruby, her face right in front of her friend’s. “Are you enjoying yourself?”

“We-we should do this more often,” Ruby replies, and, inspired, she leans in, pressing her lips up against Iris.

Iris accepts the kiss, the two women locking lips as their climaxes hit them, sending them into a blissful explosion!

* * *

Time passes, and the three girls finish cleaning up and dress themselves in their discarded clothes. As they head to the door, a distinguished gentleman tips his hat to them.

“Glad you girls could enjoy yourselves,” he says.

“Pleasure as always,” Misery replies, rubbing a bruise.

“It could be more pleasurable if we were to find a way to make some money.” He relents.”After all, we’re very much in debt and will soon be shut down.”

Misery blinks, tapping her chin. “Huh… well, I might have an idea, now that you mention it…”

* * *

Iris and Ruby would have no idea what it was that Misery would be getting them into when she first uttered those words. What they weren’t expecting was for the three of them to be standing on stage in front of a crowd of lusty lookers, cheering them on and waiting for the three of them to put on a show.

The two friends stand back, dancing relatively plainly, though they are dressed in such provocative outfits. They barely have a top other than a string bikini that hardly holds onto their tits. Down below, they have shorts that threaten to be unbuttoned almost immediately. And the boots they wear have such oversized zippers that it would be much easier to get into them than to hike into them.

While Iris and Ruby look to each other with apprehensive looks, Misery steps forward, rocking her hips and bouncing on the stage. She grabs onto a pole, hooking her leg around it and spinning around, falling back so her hair tumbles down to the floor, her arm outstretched.

Some of the viewers attempt to grab her hand, but Misery pulls away, giggling slightly and then pulling herself up, pressing against the pole and reaching behind her. With a deft hand, she pulls at the string, letting the thing fall to the wayside, the bra held up only by the pole and by her whim. Tears stream down her face, but that’s nothing new, and she pulls herself away, letting the top tumble down to the cheers of the crowd about her.

She struts over to the edge, unbuttons those tight shorts, reveals they are, in fact, tear-away, tosses them aside, and lets the ravenous crowd fight over them to do whatever lascivious things they wish with the garment.

Now only in a thong, the blue girl squats down in front of the crowd, spreading her legs and running her hands over her body. She’s a dynamo for this, letting everyone hoot and holler and reach out for her. But she spins around, showing off her cheeks, rubbing over them, giving one a firm slap. “Do you enjoy my thick ass, sir?” she asks as one of the men in front reaches up and stuffs bills in her string. Of course, he doesn’t end there, groping at that round and curvy thing.

Misery gasps out, tilting her head, her tongue rolling out. This is the thrill that she is looking for.

But for Ruby, things are entirely different. When Misery said they could put on a show, she volunteered right away. She doesn’t know if it is from the rush of the sexual satisfaction she had or some misinterpretation of what Misery had meant, but Ruby found herself in a situation so alien to her that she could hardly move. Being a back-up dancer for Misery is not something she would have expected of herself, especially when that means she is expected to strip down completely naked in front of a whole host of strangers instead of practicing intimacy with a handful of them.

But she gives it a good old-fashioned try, for misery and for the establishment, so that she and others like her can feel the joy that comes from being the center of attention for a small group of people.

She tries to think of the dance as something similar, swirling and whirling in front of the leering and jeering crowd, but she can’t really make herself get too close as the hands grope and reach out like a mass of impenetrable tentacles that seek to pull her into the depths below.

One of those arms is a bit luckier than the rest, and they grab at her arm, pulling her in closer toward the writhing, groping mass. Another grabs at her chest, squeezing her breast roughly and making her gasp and cry out.

Ruby yanks herself away, covering her exposed chest and pushing herself up. A blush falls over her face as she stands up and rushes out to the back of the stage, her eyes welling up.

Through a few sniffles, Ruby takes some deep breaths, shuddering a little bit. Suddenly, a warm hand on her shoulder makes her start, and she whirls around, only to see Iris standing behind her, also without her top. Through that big old eye of hers, the cyclops shows a mountain of sympathy for the ragdoll gal, massaging her shoulder and giving her a friendly, but understanding, smile.

“Hey, how are you holding up?” Iris asks.

“I… I could be doing better.” Ruby replies, nodding.

“Yeah, I get that. This stripping stuff, getting so close and letting them touch me doesn’t really hit my vibe, you know?”

“Yeah,” Ruby responds, taking a deep breath.

“But hey, at least Misery is having some fun,” Iris says, shrugging.

“Looks like her plan is working a little bit,” agrees Ruby.

There’s a bit of a pause between the two as they look about the room, the awkwardness filling up for a bit before Iris puts Ruby in a big old hug, bringing her in close.

Ruby had never felt such skin-to-skin contact with her friend before, and it catches her off guard for a moment, but after that brief bit of shock, she happily clings onto Iris, sighing as she nuzzles against her longtime friend. If nothing else, at least this delightful hug came out of this strange affair.

Ruby and Iris hold onto each other for what feels like forever, listening to the music thumping while Misery no doubt continues to wave herself about and get herself spanked and groped. But the two friends are far from that at the moment, caught in their own embrace.

But the song eventually shifts, becoming something smoother, slower, and more intimate. Ruby is the first to pull away from their embrace, her eyes fluttering as she sighs in delight. “Well, at least they put on something that’s not so loud,” she muses.

“Yeah,” Iris says, pulling gently away, her hands brushing over Ruby’s arms before lacing fingers together with her friend’s. “Come on,” Iris continues. “Why don’t we go out there—together?”

“But the edge of the stage!”

“We don’t have to go that far.”

“You want everyone to see us?”

“Sure, why not? Don’t you enjoy it when they watch?”

Ruby gulps, glancing over toward the stage she had only just recently abandoned, but when she turned back to the large and empathetic eye of her friend Iris, she smiles back and squeezes her hand. “Why not? Let’s go.”

And the two step out onto the stage together, the music only just hitting a swelling note. Iris lifts her arm, leading Ruby in a twirling spin before she dips her friend downward, holding onto her back and keeping her suspended by her power alone. Iris smirks, leaning in and pressing her nose right up against Ruby’s before she pulls the girl back up and extends her arm, stepping back and pulling the two back in.

A ballroom opening to their dance draw many eyes away from Misery and toward the two returning women. Even Misery, who is buried in a series of groping hands, can’t help but turn her attention to the two as they step out to the center of the stage.

“Follow me,” says Iris as she lifts her hand and strokes up and down the pole. Ruby follows her lead, smiling warmly at her friend. Soon, the two are performing a twirling and spinning dance, showing off their bodies as they lift their arms and roll their hips. They do so together, walking side-by-side and criss-crossing amongst one another, but always keeping themselves close to the pole and away from the leering crowds.

But the crowds calm down as they dance, and their jeers decrease as they observe the dance. Their eyes drink in the lovely moments and movements without a lick of the same lusty desire that had motivated them to grope and grab.

And as the two dance, they steal looks to one another, smiling warmly and tenderly as they do, soon coming together, hands pressed upon each other’s cheeks, and then pulling away. But Ruby’s pull was a little lagging, and she stands there, almost to herself, before she pulls back, letting out a soft sigh as she reconciles the little tingling feeling in her stomach.

They come back together, this time their hands upon their waists, resting their foreheads to one another, eyes looking into eyes, and Iris speaks.

“Something on your mind?” she asks, a bit of teasing left lingering in her words.”

“I, uh, maybe,” Ruby responds, sheepishly blushing as she does. “It’s just so lovely,” she says.”

“Yeah, you are,” Iris says. Those words strike Ruby like a pierce to the chest.

Ruby clutches at her breast, her mouth agape. “Iris,” she whispers. “What are we doing?”

“We’re doing what we set out to do when we first got here,” Iris says, stepping forward. She brushes a hand over Ruby’s cheek and leans in, slowly, slowly, her eye half-hooded. “We’re having fun however we want. How do you want it?”

Ruby swallows and then parts her lips, but she doesn’t have the time to respond before Iris presses her body right up against Ruby’s, arms wrapped around the girl’s shoulders, pulling her in close, their mouths pressed together.

Before Ruby could realize precisely what is going on, she’s already face-deep into the kiss, the cyclop’s tongue delved deep into her mouth, caressing her tongue in a warm embrace.

Ruby groans so loudly that it vibrates Iris, and roars out past the muffling of their mouths and over the music. She’s at once relieved and invigorated, her hands pressing against Iris’s kiss and holding her in to the kiss.

Really, it is just them holding each other, supporting themselves as they make out right there on the stage. So many eyes are on them. So many observers are entranced by their dance and their seduction of one another.

Even Misery stares with wide eyes, her tormentors paused and watched slack-jawed and with their hands poised for another spank that doesn’t come.

Ruby and Iris continue their delicate and passionate making out, their hands sliding over each other’s bodies, exploring and delving under the scant clothing that they have. They had been close friends for so long, and even here in this orgy, they never connected so closely together. Years of friendship bubble into something new as tongues caress and bodies explore, but little do they realize, zoned into their own world, that they are enrapturing so many other people.

When they finally pull apart, Ruby licking her lips and Iris giggling a bit, they notice the cheering of the crowd at the end of the song, the clatter of coins, and the fluttering of bills, all piling up on the stage at their feet.

The cheers now overshadow their voices as they marvel at the haul, and Misery scrambles up, grabbing each girl by the hand and shaking them, a rare smile spreading over her face. She shouts up through the din, with an excited cheer. “Look at all this money we’ve made. It’s a great start!”

“I’m glad to have helped!” says Ruby.

“Yeah,” adds Iris. “It was fun!”

“Of course,” Misery begins, counting up the bills. “We’re going to need much more than this. Luckily, I have another idea.”

* * *

Why did Ruby agree to help save the old theater? Why was it so important? Why did she decide to adopt Misery’s new idea to get even more money for the place?

So, there the three of them are, not even at the establishment, but standing outside of it on a corner, dressed similarly to how they were on stage, but with the outfits tighter and somehow more revealing than a stripper’s getup. But together they were, standing there, in the cold, ready and waiting for some clients to show up.

“So, prostitution,” Ruby begins, rubbing her arm. “What made you think of doing that?”

“It’s not much of a jump from being in an orgy,” says Misery, posing for passersby. “After all, you’re still having sex with strangers, but you’re doing it for money instead.”

“Yeah, well, that’s well and all,” says Iris, “But I think doing things with friends and friendly types is kinda different, if maybe a little?”

“Huh? How so?” Misery asks, but when Iris opens her mouth to get more details, someone walks up to the two of them.

“Hey, Misery,” the man says.

“Oh, hi, John. The usual?”

He pulls out a leather length and smirks widely. “You know it, babe.”

“Alright, but remember, the clock starts now.”

“Of course!” He says this, grabbing her right there and stripping her down. He undoes her like a master working at a puzzle, peeling off each scant layer until Misery is fully naked without having moved a muscle. The two friends watch with wide-eyed amazement, only to snap out of it when he snaps a collar on Misery and clips the length to the collar. Tugging on the leash, he snaps his fingers and points to the ground.

Misery hops down on her knees, her hands up by her chest and hooked down by the wrists into little paws. Her tongue rolls out, and she stares up at him, panting quickly.

“Good girl,” the man growls, yanking the leash and walking away with her.

On all fours, Misery crawls away, looking over her shoulder and whispering a quick “See you later, guys,” to her friends.

Now alone together, Ruby looks to Iris, and the ragdoll bites her lip. She thinks for a moment that she should push down the words and thoughts that crowd her mind, but another part of her tells her it’s now or never to ask her question, so she takes a deep breath and says. “So, Iris…”

“Hm?” Iris’s eye lights up when Ruby speaks.

“I was wondering,” Ruby pauses, rubbing her arm. “Are we, like, dating, or something?”

Iris blows a strand of hair out of her face, staring up into the sky. “Huh, yeah, I dunno. I mean, I’d like to and all, but…”

“But what…?” Ruby feels her heart sink.

Scratching her cheek, Iris continues. “I kinda, well, sorta saw you as out of my league… and honestly, assumed you were straight. It’s silly, really. Plus, you see me as a friend and all, so I can’t really mess with that.”

Ruby pouts upon hearing those words, but she places her hand on Iris’s shoulder. “You’re right about that. That is how I saw you… before we started doing all this sex stuff together. I’m… well,” she smiles warmly, squeezing Iris’s shoulder, “I’m ready to explore the idea of a relationship.”

Iris squeals and wraps her arms around Ruby, squeezing her tightly and rubbing her cheek against her cheek. “Oh, great! I can’t wait to take you on a real date, Ruby! It’ll be amazing. Just you see, I got so many ideas and—”

“Excuse me, ladies,” the voice interrupts the two of them, and Iris lets go of Ruby, turning to face the newcomer. A woman, dressed in a concealing coat, a broad hat, and sunglasses, stands before them. She looks around furtively, as if she’s afraid of being caught.

“What’s up?” asks Iris. “Can I help you?”

“Well,” the woman says, gulping. “I heard that if I wanted to, well, explore myself with other women, I should go with a pro.”

“Oh yeah, well, I uh…” Iris glances back at Ruby, offering an apologetic shrug.

Ruby waves her off with a smile. “You two have fun. We signed up to work, so let’s work, right?”

“Right.” Iris grabs the woman’s arm and leads her away. “Come on. Let’s show you a whole new world!”