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The Dark Side of the Bright Side	By : FairySlayer Category: +M through R > Ruby Gloom Views: 4258 -:- Recommendations : 1 -:- Currently Reading : 0
Disclaimer: I do not own the "Ruby Gloom" or have any connection to the property whatsoever; I receive absolutely no money or compensation of any kind for writing this. It's simply parody for the sake of entertainment.

Chapter List
- 1
- 2
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Dedicated to (and initiated by) Tommy Simms; special thanks to the Evil Fairy for proofreading/editing.
A Rough Night
My name is Ruby Gloom and I live in Gloomsville, in my family home Gloom Manor. It's a big mansion and costs a lot to keep. It needs a lot of repairs and stuff too. After my parents died I rented out rooms to make money but it was still really tough to pay all the bills. For a while I was scared I'd have to sell it and move away.
But luckily one of the housemates, a skeleton named Skullboy, knew what to do, and now he takes care of everything. He got us girls jobs to pay for the house, food, clothes and everything and still have enough left over to buy really nice things sometimes. He calls us "streetwalkers" but there's not much walking for real. We just really stand around until we get a customer, and then we're usually on our backs or leaning over something while they make love to us. Usually it's fun but sometimes it hurts - and sometimes when it hurts it can still feel really good. But the customers always nice, at least to me. I didn't know why or really think about it much until one night last month.
It was like any other night. I had done three or four tricks already. So once again I was leaning against the lamppost in front of the Come On Inn. It's in an old part of downtown Gloomsville. Not many people stay there anymore 'cause the area's kind of run down and dirty. But we rented rooms at the inn almost every night, and I guess that was enough to help them stay in business. It was really late, long after the creepy unnamed book store next to the hotel had closed. The flame of the gas light above flickered dimly as always, making the alley between the two buildings seem even darker than pitch black. It was chilly enough already, but looking over there made me feel colder. Still it was hard not to glance occasionally 'cause I knew Skullboy was there keeping an eye on me.
Almost all night every night he was there looking out for me, and whenever anyone came over to talk to me he'd come out to make sure everything was okay. If it was a regular customer it didn't matter much, but if it was a stranger he'd always come over. Sometimes he'd have to help me sell myself because a lot of guys would say I'm too pretty to be making love for money. Skullboy could convince anyone that it was okay. He had a trick and it was kind'a cute: he could instantly copy anyone's mannerisms and way of talking just by listening to them talk for a few seconds. He could become a different person anytime - bang! just like that. It was really neat, but it could be scary at times too. (Sometimes I even wondered if the way he was around just us girls was for real or just another one of his acts.)
Even when I could get someone new by myself Skullboy came out to have a few words with him. Well, it was usually a guy, but sometimes other girls would want to have sex with me too. (Once a married couple begged Skullboy for me have sex with them, but he said I wasn't allowed to do three-ways.) Anyway, he told me he just wanted all of my customers to know I was a classy gal and that they had to follow the rules. Special rules just for me, he said. And he wanted them to know that he was right there in case there were any problems. Sometimes they'd argue with Skullboy about the price or what they were allowed to do and they'd get really mad, but that kind of thing never ended well. Not for the johns.
But if the weirder ones were cool about it he'd let Iris take care of them instead. She's a very pretty girl, even though she has only one big eye in the middle of her forehead. She's beautiful up and down, super fit and really strong because she's always exercising or running around. She loves doing anything fun, even if it hurts. And Iris is always really happy about having sex with strangers, or anyone, because she loves to make other people feel good too. She always got a lot more customers than me because she'll do any of the weird and gross things that some of them ask for. Sometimes she'll tell me all about the stuff she did with the customers, though a lot of it sounded really weird. Anyway she's real smart too and can figure out what people will like even if they don't think of it themselves.
So anyway, finally a new guy came up to me. His heavy overcoat was open and I could see he had a really nice suit on underneath. He flashed me a big smile, showing off his beautiful and perfect white teeth. He just smiled like that for a minute, looking me up and down. I think he really liked the dress I was wearing.
It was my favorite: a black sheath dress made of very smooth and shiny silk, and it was so short it barely covered my bum. If I ever wore it during the day then everyone would see my red & black striped panties, but I was only allowed to wear the dress at night. (We were never allowed to wear our working clothes or even put on makeup during the day.) Except for two very thin shoulder straps it only reached barely above my armpits, showing off my neck and shoulders completely. You could even see the top of my breastbone, and maybe you'd be able to see the tops of my boobs too if they were bigger. But that was the best part: wrapped all the way around my chest there were a bunch of really tiny, finely cut pieces of ruby sewn into it. That part was narrow and a little more snug on the sides. So even though I don't have much to show it made what little I have really stand out, yet at the same time it showed that I barely had breasts at all. But most of my customers said they liked it that I had a really small chest anyway.
The real reason it was my favorite was 'cause Skullboy had it made special for me, and a matching purse too. It was really expensive, but he said wearing it would bring me more customers. He also said the rubies were an inside joke. Even with the extra business it got me I don't think I'd have made enough money to pay for it in a year, but he said I was his favorite and I should have the best anyway. It was weird like that because I know Iris made him a lot more money than me but he would never buy her anything nice like that just 'cause. Sometimes she complained about not getting nice gifts like me, but only to me and not too often. She didn't want to make me feel bad I guess, but I did anyway. Instead she usually complained to Skullboy about a lot of other stuff.
So anyway this guy was just smiling at me. And then he suddenly blurted out, "How much?" It was so sudden, so eager that it made me blush and I could only giggle.
Skullboy saw I was losing it so he came right out, flashing a big friendly smile of his own as he strode over. He always looked so cute in his fur-lined overcoat and fedora, carrying his walking stick, but when I told him that once he hit me and I kept it to myself after that. "A very good evening to you, fine sir," he said with a hint of British accent. "Allow me to introduce myself: I am Monsieur Skulét, and I see that you've already met my best girl, Ms. Glimmer."
See, whenever we were out working I had to use the name "Glimmer," and the other girls had special names too. They were close enough to our real names so that we'd never forget to answer to them, but different enough that no one could figure out who we really were. Skullboy said he didn't want people to bug us during the day when we weren't working, or worse, show up at the mansion. For some reason that really seemed to scare him. Anyway, he could make a name for himself just like that, always what he thought the customer would be comfortable with. And he always got it perfect.
"Good evening to you too, Mr. Skulét," he answered in a British accent before turning to me. "And to you, Miss Glimmer." Once again Skullboy had nailed it, and from just two quick words from the guy's mouth. "I hope talking directly to your lady friend wasn't a faux pas, but I didn't see you..."
"That is quite all right." Skullboy thought he was nice enough so he got straight to down to business. "I'm sure you and Miss Glimmer would enjoy one-another's company very much." Skullboy would usually just nod to me at this point and I'd go wait in the hotel lobby, but this time he tilted his head to one side while smiling at me: he wanted to put on more of a show for this man, probably hoping to get me another repeat customer. "Miss Glimmer, why don't you go inside and warm up a little while we chat awhile."
I thought I'd be a little fancy myself too this time, so I gave them a little curtsey, being careful not to raise my very short dress. "I would be most happy to, Monsieurs." The man let out a small laugh and Skullboy briefly shot me a nasty look. I knew I might be in a little trouble for saying something wrong but I kept smiling anyway. It turned out that that was no big deal compared to everything else that happened.
I quickly went inside to get a room key while Skullboy told him what he could do to me and what he couldn't do. I never knew exactly how much he charged for me, but I knew the rules by heart: they could only have oral or straight sex with me; and though they could do any position and some other stuff to me, they couldn't do anything that hurt too much. They definitely weren't allowed to stick anything in my bum and, most importantly, they weren't allowed to leave marks on my skin 'cause it's so light and bruises would really show. So no big hickeys, red handprints from hard spanking, or anything like that.
Sure, sometimes a small, light mark here or there couldn't be helped, but I had some good cover-up in my "working bag," which the bellhop would bring up to whatever room they had for me when I got there. The bag also had everything else I'd need to get cleaned up quickly between tricks, and I had plenty of condoms of course. It cost a lot extra for the guys to not have to use condoms, and even then Skullboy would only let people he thought were clean enough.
So this British guy came into the lobby with his big smile and sparkling eyes. He looked me up and down and then puts out his elbow. It took me a minute to remember that I was supposed to hold his arm like that. I'd seen it in a movie once. When we got to the room he took the key from me and opened the door, letting me in first. He was a real gentleman, and that was always nicer than the guys who were drunk or in a rush. As soon as he closed the door he reached into his pocket and pulled out the ivory coin with a red metal edge. It was the token Skullboy gave men who were allowed to cum inside me.
I don't know if Skullboy had something like that for Iris too, but I was pretty sure there were no rules at all for the other girl, Misery. More about her later.
So I did the usual: I put my purse on the nightstand and then left the coin next to it, just so I could look every so often and make sure it was there. Sometimes I had so many customers a night that I couldn't remember otherwise. In the meantime he'd hung up his overcoat and taken off his tie. I was a bit disappointed because I like to undress them myself and check them out, but maybe he just didn't want it to get in the way.
Okay, so then I turned around and lower my face but still look up into his eyes. Then I smiled really wide, so much that I make myself blush, and I took a baby step to him. My usual routine is to play vulnerable and let them start in any way they want to. Before I got too close he held my shoulders to stop me, and again he just slowly looked me up and down.
And then he surprised me again.
He suddenly pushed me backwards so fast that I barely had time to move my feet, but it didn't matter much. In an instant I fell back on the bed and he was straddling me and holding my arms tight. I wasn't too worried though because I knew Skullboy always hung around in the hallway, sitting in whichever of the big comfortable chairs was closest to my room. Just in case.
I kicked off my high heels as he started kissing and licking around my face and neck. Then he started using those big beautiful teeth, very gently biting into my skin. I was scared he'd start doing it harder and get us both in trouble, but he seemed to be controlling himself so I didn't say anything. Besides, he soon pressed his mouth to mine and started working over my lips with his. His tongue slid into my mouth and started playing with mine on and off. He relaxed his grip on my arms and just kept kissing me while feeling my upper arms. I was so caught up in the kiss that I didn't care. I could already feel my pussy getting hot, and I'm sure my panties were already at least smelling like my girl juice. I'd be really wet really soon, but that was good because he seemed so very eager. I tried to reach up to take off his shirt but he had my elbows out to my side and was pressing down on them. It wasn't too hard, but I couldn't do more than raise my hand and feel up his arms.
He moved his mouth away from mine, leaving a trail of hot saliva as he began kissing my cheek. Before I could do anything he moved to my chin and then began on my throat, again biting me just hard enough to make me nervous. But it also made my heart beat faster and my stomach go all atwitter. I felt my whole body go flush with excitement and could feel my hot spume leaking out. Luckily I had on panty shields that usually kept any of it from getting on my nice dress.
God, I loved that dress, and I wanted to get out of it before anything happened to it. Sure, cum all over me and that's fine, but don't cum on my nice dress! I playfully tugged at his sleeves, trying to hint that we should get undressed and get down to the real fun. There was no change as he sloppily kissed and mouthed his way towards my shoulder. I finally was able to turn my face towards his and began kissing his ear, licking and sucking on it while he did the same to the nape of my neck. Without realizing I gripped his sleeves really hard and pulled enough to make one of its buttons come undone.
For some reason that set him off. He suddenly bit into my shoulder hard, making me yelp for a moment. But he wasn't really trying to bite me - he gripped the dress strap in his teeth and jerked his head back, snapping it like it was licorice. Then he sunk his teeth into the soft silk just above the rubies and somehow managed to make a little tear, then again. I gasped loudly and my whole body went stiff.
My excitement faded when I realized what he was doing: he finally made a tear at the edge of the dress and then bit into one side, growling fiercely as he reared back and ripped the dress. He tore it just beyond the studded strip, revealing my left breast. I let out a whine of protest and struggled to break free and grab his head, but he held firm. He clamped his mouth on my small mound and sank his teeth in just around my nipple - a "pink zone" where it was okay for them to be a bit rougher. His warm, wet mouth felt so good sucking up my nipple, his tongue flicking over it then drawing rough circles, that I forgot for a moment what he'd just done.
His pearly whites clamped onto the tear and he jerked his head again. I thought about screaming out for Skullboy, but the look on this guy's face had changed. He looked fierce and mean, like a starving animal, flailing his face around to rip apart some defenseless animal. Or a helpless little girl like me. It made me too scared to say or do anything. He tore away a long strip of dress until he could drop most of the ruby band to the side, freeing my other breast. Its nipple was already hard from me being so scared, but there was also some lustful aching pulsing through me too. I felt a hot breath on my untouched little mound, so I closed my eyes and arched my back to press it closer, but instead he hooked his front teeth into the other shoulder strap and broke it with incredible ease. He then nuzzled my anxious, perspiring little chest mound but suddenly went for my sternum and gripped the dress between his teeth again, pulling extra hard. This time nothing happened at first, so he started grinding his teeth until he'd frayed it enough to tear a whole strip downward. It seemed like he'd peel it all off in one go, but the piece broke free just above my bellybutton.
The now crazed man let the drool-soaked fabric drop from his mouth as he nearly slammed his face into my stomach and drove his tongue deep into my navel, swishing it all around between harder bites to pull up the thin layer of skin at its edge. I knew he was being too rough but I didn't want to call Skullboy if I didn't have to. I felt scared and ashamed enough already.
So I started to loudly say, "Noooo!" but he put his hand over my mouth and got up on me again, straddling my hips while pressing down on my face. He grabbed my right arm even harder.
The flickering gas light only made the look in his eyes scarier. They were full of anger and desperate need. "It'd be a shame to stop me now, baby. We're just getting to the good part." Then he simply took his hand off my mouth and gripped my waist with both hands. He didn't warn me not to say anything else. He didn't have to. Then just to show me who was in control he bit hard into the bottom of my stomach, through what remained of my dress. But it didn't remain for long because he then somehow dug his teeth underneath and tore out another chunk. Two more tiger-like chomps and then one long tear down the skirt left my front totally open. I almost started to cry again as I felt the last scraps fall off my hips. And all I could do was lie there and not even do anything 'cause I was so afraid of him.
Then he got up over me once more and moved his face towards mine, so I made myself ready to accept his kiss. Gladly, just as long as he didn't hurt me. Yet despite how vicious he seemed about ruining my dress he didn't seem to want to hurt me. It was like he didn't care so much what I was doing as long as he got to rip me out of my clothes. Like how Iris excitedly tears open her Yam Ween gifts while I always try to save the gift wrap.
He suddenly grabbed my thighs and pushed them apart while diving face first into my pussy. My panties were already so wet from excitement that they stuck to my mound as he sucked it. He forced my legs even wider apart and turned his head sideways. I must have squealed a little when I felt his teeth hit the sides of my pussy and then closed it together lengthwise. His mouthing was so hard and it squeezed so much that I swear I could hear my panties squishing. He ran his tongue left and right through his bared teeth, going up and down the edge of my slit.
I guess he didn't care so much about the panties because he just suddenly grabbed the waistband and snapped the right side apart. Then he pulled it up my left leg, trembling and fumbling to bend my knee so he could throw it completely off. Meanwhile his tongue bored full force into my tingling muffin. I could already feel warm liquid dripping between my thighs and inside my bum cheeks, but I don't know if it was all me, his drool, or probably a lot of both.
As he turned his head straight he kept attacking my "baby hole," not just licking but like slapping it with his tongue, or just lapping really hard I guess. I tried to put my hands in his hair, which I do just 'cause usually that's what they want. Sometimes I have to guide guys to eat me out right - but not this guy! But as soon as I did he pushed me over onto my right side and pulled my left knee high into the air. He could still get at my cunny easily, and he kept sucking and just sort-of biting me there once in a while.
His free hand pinched my bum and then he started rubbing my slippery wetness up and down my bum crack. It turned me on a lot more and I almost started to forget about everything else. He was eating me out so good that I almost didn't notice that he started teasing my very wet asshole with his fingers. That was actually kind of nice and tingly. But then he started pressing harder and harder with each stroke. That was a no-no. I gasped really hard and he immediately stopped. I think maybe he thought I was really gonna yell or something.
Instead of getting mad or anything he just pushed me over onto my stomach and lifted my hips so that my bum was up in the air. My legs had gotten a little stiff by now so that made them feel better. Then he grabbed my hands and put them behind my back, so my chest and face were lying flat on the bed. I looked over at the dresser mirror and watched as he leaned down and whispered. "Keep your hands there like a good girl and I won't have to tie you up, okay love?"
The rules said tying me up a little was okay anyway, but I nodded uh-huh and kept looking at us in the mirror. He must have unbuckled his belt while telling me what to do because his pants just fell down to his knees. His cock was already sticking out. It was big too. Not the biggest, but I still knew it might hurt. I hoped he'd stick his fingers inside my cunt instead and loosen me up a bit. At least he took it slow, gripping it by the very bottom, like it was a hammer or something. Then he rubbed it all up and around my pussy lips, letting it bend and flex a bit so that it would suddenly flick away, sending a bit of a chill up my spine. He'd push forward to get more of my spume on it, and then he might squeeze it between my ass cheeks and slide it around to make sure he got me all wet and sticky in between there too. He kept pushing it back up or down, and I didn't mind that the head always pressed on my sticky butthole each time he put it down. I didn't mind at all, but I prayed he wouldn't go any further.
After he was good and ready he clenched one of my ass cheeks really hard and pulled it to the side. In the mirror I could see him just smiling down at my exposed pussy, asshole and pretty much all of me. With his other hand he slid two fingers right into vagina, just like that! I was so slick and so hot that I guess it opened up by itself. I thought for a second how I couldn't wait to tell Iris, but the feelings of his fingers going in deep, slowly, and then out again a few times made me forget everything I was thinking. I could only moan and watch weakly through my half-closed eyes. I managed to perk up a bit to watch as he pressed the head of his seven-inch cock against my eager opening and start to stick it in.
Like again, he wasn't at all rough with me. I guess he just didn't like clothes or something. (Skullboy always says that clothes make a pretty woman look even better and that's why he's so picky about them. But one of the boys who rents the garage says women shouldn't have to wear clothes so he could see how pretty they are, but then his other head says clothes are really just to hide ugly people's bodies.)
So anyway I felt his fat cock slip into me a few inches and then he stopped. He could have kept going if he wanted to, and even if it hurt I wouldn't have minded 'cause it felt so good. He spit and a gob landed on my asshole, making me cringe for a moment. He smiled, probably because he saw my asshole wince. Then he slowly worked the spit down to his cock, pulling out almost all of the way and then letting a little more drool fall onto my smooth, chubby lips. Then he slid back in and I nearly melted. I could only moan and my vision got blurry, I guess because my eyes were half closed. And a bit watery. He just worked it in and out part way for a while and I just moaned. I really like fucking and he was doing it good.
All of a sudden he plunged it all the way into me, really fast and so hard that his pelvis slapped my bum. It made me jump and I forgot to hold my hands behind my back, but it didn't hurt at all like I thought it would. Instead it just felt really nice and full, and he started pumping me like that, just backing out a few inches and then all the way in again, over and over. After remembering to hold my hands behind my back again I just let him do his thing. It's not like he was shy about making me do what he wanted, so I rested my head down on the bed and tried to enjoy it. I felt my insides start to shake and some perspiration ran down my cheek. But as I let my face rest on the bed I could feel the tiny ruby beads against my face. I wondered if maybe some of what I felt were actually teardrops.
For all of his excited foreplay it seemed like he didn't last long, or maybe I was just still too shocked to really pay attention until he fell on top of me. I was pinned and he was crushing my leg a bit, but I could still feel his cock jerking inside me as it spit out lots and lots of hot cum. I felt the warmth of it leaking out over my pussy, replacing the chill of cold spume and spit. I felt close to coming myself and didn't want to stop yet. As he was just lying on me, panting, and now I was too. I started wiggling my butt so I could come before he got soft. I knew he'd be sensitive, but he pushed with his knees and drove his dick deeper in me so he wouldn't feel it as much, but it was enough to make my insides clench up then release. I didn't realize that I was actually holding him up a bit the whole time until my body went weak and I sank flat into the bed. Good thing it's so soft 'cause he was heavy now.
He didn't move, and I just lied there too while trying to catch my breath. Only after my head cleared I started to feel the cold puddle of goo spreading under my pussy and thighs. I cleared my throat and he finally lifted himself up. His cock plopped out and so did more cum. Before he could even get on his side I crawled out from underneath him and ran into the bathroom.
I ran the water, got the towels and did my clean up. Skullboy says it's important to get back on the street as soon as possible. Some of the repeats will go inside and wait a little while, but usually not for too long. I ran a fresh washcloth under cold water and wiped my face with it. It was the only way I could stop tears from leaking out once in a while. I was still shaking even as I pulled out my spare dress. It was a nice silver cocktail dress. It was tight and showed me off good too, but I couldn't stop thinking about my favorite dress lying on the bed, ripped to shreds and covered with pussy juice, cum and spit.
When I was done he was already out in the hallway talking to Skullboy, smiling and laughing as if everything was fine. I grabbed the remnants of my ruby dress and stuffed it in my bag. I thought maybe I could fix it, but I really knew that I couldn't.
"Miss Glimmer?" Skullboy called gently from the hallway. I quickly wiped my face one more time before grabbing my purse, coin and key, and meeting them in the hallway. Skullboy glowered the instant he saw me in my spare dress. He knew something was wrong and he was already mad without even knowing what. He snatched the room key from me and I just turned away.
"Let's all step outside for a bit of fresh air," he suggested, and we all started walking. I could only look down at the floor the whole time. I'd never noticed all the animal and people designs in the old thick carpets before.
Once we got outside Skullboy just kept making small talk while casually meandering over to the alley. The guy didn't notice anything wrong and chattered back, talking about his childhood in England or something. That all changed as soon as we got to the edge of the dark alley.
Skullboy immediately lost his accent. "So Glimmer," he finally addressed me, "What happened to your nice dress?"
I bust out crying. I couldn't look right at him, though I did steal a glance or two I guess because I can remember his pursed mouth and the burning in his eyes. All I could do was sob softly, "It's ruined. It's ruined..."
"Ah, I'm afraid that's my fault," the man chimed in. I looked up at him, him and his goofy smile. "I kind of have a thing for disrobing the young ladies with my mouth, and I guess I got a bit carried away. But it's no big deal I imagine. Cost of doing business for you I suppose."
I turned to Skullboy and watched as wisps of steam literally came out of his mouth and ears.
The man noticed too. He quickly pulled out his wallet and opened it up. "Of course I should reimburse you. It seemed like a pretty nice dress after all." He started counting out the bills and then stopped to feel the edges of his teeth. "Actually I think I may have chipped a tooth on one of those paste stones," he remarked before asking, "How much?"
Skullboy seethed, "All of them."
"Come again?"
Then Skullboy smacked the wallet out of the guy's hand, sending it flying into the alley. The gentleman's eyes followed for an instant but as he turned back his jaw met Skullboy's fist. It made a juicy popping sound: it was so sickening that I'll never forget it. Before he could even try to protect himself Skullboy got him with the other fist, knocking the man back onto the ground. He had barely started to get up when Messr. Skulét's boot landed square on his mouth, knocking his head sideways. The man's mouth opened as he spat out some blood.
Skullboy immediately turned around and grabbed the man's ankles, dragging him into the darkness of the alley. I started crying again. I ran over behind some garbage cans and sat all curled up, covering my ears. The man screamed and groaned between a steady stream of loud punches and kicks. There was so much noise I thought someone would definitely come and stop him, but no one did. After all, he pretty much kept the hotel in business so they wouldn't do anything to him, and he often said that he was "protected" from the police around there.
I tried to block it all out, but after the hits stopped the man suddenly started screaming even louder. It was a gut-wrenching gurgling scream, like he was drowning or something.
"Ruby," Skullboy said plainly as he stood over me. I looked up at him but didn't move. He pulled all of the money from the man's wallet, clenching the bills between two fingers of his cupped hand. Then he carelessly tossed the wallet back towards the alley. I watched it spin in the air and was kind of surprised when I didn't hear a whimper when I heard it land.
"Get up."
I did, though I couldn't stop trembling. I found myself pulling my face back from him. He always said that he'd never hit my pretty face. He said it was too good a moneymaker and it was going to buy him a big Cadillac someday. But I still thought he was going to punch me in the face anyway.
He pointed at my purse then wiggled his two fingers for me to hand it over. Again, I obeyed, but too slow. He snatched it from my quivering hand and the tiny gems scratched at my fingers. It was one last reminder of the beautiful dress I'd lost. With the money still in hand he opened the purse and then, from his cupped hand, started dropping the man's bloody teeth into the purse.
"There we go. Twenty-eight teeth," he said slowly, harshly. "Know what else they are?"
I could only shake my head as he finished. Then he opened his thick overcoat to put the money away. I couldn't help but notice the speckles of blood. He noticed and looked too before brushing away a few more droplets, but he really just smeared them on the fur lining.
"They're twenty-eight reminders why," he said while moving his face close to mine, "you're supposed to call me when Johns do something wrong!!" With that he slapped me in the side of my head. Hard. I was trembling so much that I don't know how I kept standing, but I didn't dare cry anymore. Then he grabbed my hair really hard and pulled my face right up against his. "Do you know how long it took me to come up with the idea for that dress?"
He kneed me in the hip and I tried to keel over, but he only pulled harder to keep my face even with his. "And then I had to go all over the city just to find someone to design it! Do you even know that that costs money too, stupid bitch!"
With that he punched me right above my stomach then opened his grip, letting me fall onto my knees hard. Then he slapped my head again, knocking me onto my side. I started gasping and fighting for air while curling up in a ball, trying to protect my smarting chest. He kicked my shoulder with his heel, just hard enough to push me over onto my stomach, and then he immediately sat down on my back. I was terrified of what he was going to do to me, but I remember thinking at least he didn't drag me into the alley.
He leaned down and put what would be his cheek against the back of my head as he snarled in my ear, "And do you know how much that dress cost? It was nearly three-thousand dollars!"
I winced in fear but after a moment he just rocked back on his feet and started to get up. Suddenly he yelled, "American dollars!" and punched me right in the kidney! I still couldn't breath enough to let out a scream, but my face fell right into the cobblestone sidewalk. I felt the warm trickle of blood pooling up under my nose. I just lied there and played dead. I wasn't going to move or make a noise or anything. For a moment I thought there was nothing that could ever make me move from that spot.
"Get up," he said.
I immediately did. His eyes went wide when he saw my bloody nose. His expression suddenly softened and he pulled out his handkerchief, gently holding it to my trickling nose. "Oh Ruby," he cooed.
I started bawling.
"I'm sorry. I didn't mean to hurt you like that, Ruby. That guy just made me so mad because I know how much you loved that dress." He lifted up my chin but I kind of looked away from his face. "You know I love you, right? That's why you're my bottom bitch, and you're also tops in my book."
After that he took me back to my room and helped me clean up. My nose stopped bleeding but I couldn't walk that good, so he told me I didn't have to do anymore tricks for the night. Then he suddenly brightened up and held a bony finger to his eerily hard lips, if you could even call them that. "I have an idea! Let's go see what Iris is doing. Would you like that?"
I nodded. I was kind of curious to know if the stuff she said was really true.
Skullboy led me down the hall and in back, through a bunch of twists and turns until we came to a part of the hotel I'd never been in. Though I kind of knew we were near the stairs to the basement, and for some reason that's where Misery usually worked. Like I said, she was weird, and everything about her was too.
Anyway, he took me in another direction and then we went into another small room. There were windows on two walls, two tiny single beds and all sorts of kids' stuff, like in the decorations. There were even some old toys and games on the shelves by the windows. It looked like the kind of room that would probably make some of my regulars really horny. So then I notice an extra door, and there's a lot of noise coming from the other side. Skullboy crept up to it then turned back to me and whispered, "In the old days families sometimes stayed here, and they put these kids' rooms on the far side of the hotel so they could make noise without bothering other guests. That's why it's a good place for Iris to work."
I snuck over quietly too as Skullboy ever so carefully opened the door, just a crack. Before I could peek Skullboy put an arm around my waist. I looked up at him and he smiled at me. I don't know why but I smiled back despite what he'd done to me. Then we both turned to look.
There were a bunch of people in the room, Iris and three men. A fat man with dark black hair pretty much all over his body, was standing over the bed wearing nothing but his underpants around his ankles. He just stood there watching and slowly wanking himself. On the bed Iris was on her hands and knees, rearing back with her butt sticking up in the air. There was a blond, green-eyed boy with an odd-shaped head, no more than ten or eleven years old, kneeling behind her and shoving his cock first into her cunt, then he'd pull it out slowly before slamming it all the way into her ass all at once. Then he went back to her first hole again. I cringed, at both the idea of having something in my butt and also then having it in my pussy after. But since Skullboy was very demanding about us keeping clean then I figured she must have washed inside her butthole too.
Then the third guy, really tall and with light brown hair, was lying at the head of the bed. His hands were behind his head and his legs were spread. Iris was happily sucking and slurping on his nine-inch cock. I always had trouble except with the really short ones, but she seemed to bob up and down the whole length. She had to be taking it halfway down her throat! Then every so often the guy would reach over and grab the back of her head, holding her all the way down on him as he bucked his hips, basically fucking her throat. And as soon as he let go she'd back off quickly, and I swear she was giggling.
Finally the hairy guy walked around to the head of the bed. Iris leaned on one hand as she continued blowing the brunette and used her free hand to start jerking off the hairy guy. But he stopped her, so without hesitating she stretched herself over and sucked on his dick a few times. She had to grip his ass for support. Grip it hard, but he didn't seem to mind. He even held her wrist to support her as well. Then, after a few deep sucks she'd turn back and suck the other guys cock a few times again, though she was face fucking them each a little faster than before.
Then the tall guy who was lying down grabbed her hair and lifted her face off of him. "Okay bitch! How would you like to get all of your holes stuffed at the same time?" He was kind of laughing as he said it though.
"Would I!" Iris nearly shouted. She waited for a second, apparently reveling in the thought, then reached behind her to grab the blond's hips. She kept him still, with his cock still in her ass, as she raised herself onto her knees. Well, the dark guy had to help a bit, and the blond seemed to melt in pleasure as Iris slowly wriggled her bottom around his deep-seated cock. The tall guy shimmied down underneath them, forcing Iris and the blond to spread their knees a little, but then the tall guy just lied down with his nine-inch dick pointing straight up at Iris's literally dripping pussy.
The blond grabbed Iris's hips now as she slowly got on all fours, and then she basically lied on top of the tall man while guiding his dick into her snatch. All the time she tried to keep the blond boy's dick from coming out, but I think it might have just at the end but not for long. In a moment they were both deep inside of her.
It was weird. Both of the men did their best to lie still, squishing her in the middle, yet somehow Iris managed to raise and lower, pull and push and churn her lower body around so that both of their cocks got moved all around inside of her - all while never slipping out! Then just as she was getting her rhythm set the hairy guy got on the bed and kneeled in front of her. The tall guy had his eyes closed because it must have felt really good. He was oohing and ahhing and didn't seem to notice the hairy guy was basically straddling his face. But then the tall guy grabbed onto the front of hairy guy's legs with his palms and used the extra leverage to pump Iris a little harder on each stroke.
Meanwhile, Iris leaned forward and started blowing the hairy guy, still never missing a trick with the other two cocks she was working down below. The hairy guy gripped her shoulder-length hair in his hand and jerked her head back and forth, forcefully fucking her mouth and throat while she continued to wiggle and wriggle enough to make the other two gasp and moan with pleasure.
And all the time it was clear that she was still smiling, letting out a snort of a giggle now and then. But she was sweating and creaming while squirming and fucking and sucking. I could tell she was starting to quiver a little. I have to admit that watching three men fucking her at once made me feel a little hot too, and a little jealous. It even made me forget some of my own pain a little.
So, finally I can tell from the sweat pouring off of her and the way she's swaying with every move that Iris is just lost in ecstasy. But she's a trooper and she never gives up no matter how hard it is to concentrate. Actually, I think it could be that she does better when she's not thinking at all. Suddenly the hairy guy grabs her head really hard, plunging his cock all the way into her face while grunting and groaning. He's wiggling his hips just a little, and I can see that Iris's throat is swallowing like mad as he keeps squirting off. The tall guy has pretty much stopped moving, and after a minute he has to reach and stretch really hard to get his hand down and pull his half-limp cock out of Iris's pussy. Of course a bunch of his spunk leaks down onto his cock and hand too.
By now the boy has grabbed Iris by the hips so hard that I could see his fingers digging into her a little. He was pumping her ass furiously as he could, using short fast strokes so that he wouldn't risk his dick popping out of her. It was so funny looking that it made me laugh a little, even though it hurt to laugh.
The hairy guy finally pulled back and Iris instinctively sucked on his cock. Not too hard since he's still sensitive, but I bet enough to get out every last drop as he went soft. All the time her eye was closed and she's breathing slowly and heavily through her nose. Her hair's stuck to the side of her face from the sweat, but she kind'a looked just like a little baby nursing. Finally he pulled it out of her mouth and got off the bed. Iris immediately dropped her hand down onto the tall guy's chest and was seriously panting. The blond boy is going at it like crazy and both his eyes and Iris's scrunched up really hard, and Iris was letting out little groans and whatnot.
So the tall guy puts his arms around her and starts brushing her hair while whispering something to her. He's being really sweet-like to her and she's starting to let out short whines. Then she sucked in a huge breath and her whole body went rigid again. The boy seems like he was keeping his cock deep inside but Skullboy whispered that when she comes her ass gets really tight so the boy was probably stuck. Anyway, Iris lets out a long and almost painful moan followed by some grunts, one every couple of seconds. The boy suddenly goes still and throws his head back, but Iris moves her butt around in circles to make sure she finishes the boy real good. He starts grunting really loud and then does his best to follow her motions with hips. He also starts to pump in and out again, just a little. His cum is leaking out and that's probably why he can move it again. Meanwhile Iris is trying to catch her breath. The tall guy under her started kissing her ear and rubbing her back by now.
So then the boy pulled it out and grabbed his cock. It was still mostly stiff and he sort of wiped off the tip on the insides of her cheeks, drawing sticky lines in the sweat covered buns. For a second it made me think about making hot-cross buns for breakfast.
But then the blond boy and the hairy guy rolled Iris over onto her side, and the tall guy got up. With a little urging the tall guy got Iris up on her hands and knees again. The hairy guy got on his knees behind Iris while jerking his dick to make it harder again, and the tall guy got on his knees at the head of the bed. Iris first used the tip of her tongue to lick the bit of sperm off the tall guy's limp penis, but soon she took it into her mouth and gave it a good sucking and tonguing. The guy behind her spread her knees and then gripped her thighs. Without even caring about the cum covering and dripping from her two gaping holes he stuck himself into her snatch and just started fucking her in long and fast strokes.
The tall guy's holding the sides of her face with just his fingertips, trying not to stop her from doing it her way I suppose. Once in a while he paused to stroke and pet her hair too. I bet he was a regular because of the way he seemed like he really cared for her, like he knew her or something. Though sometimes people are like that to me even when I've never met them before. Some guys even spend most of their time hugging me and giving me kisses all over before they want to fuck me.
The blonde boy went over and sat on the edge of a chair. He spit on his hand and started playing with himself. He was already pretty hard so he started going fast. I could tell that the hairy guy was pretty close even though it hadn't been more than a couple of minutes, and the tall guys' cock was rock hard again. It wasn't long before the hairy guy grabbed Iris by her waist so hard that it pulled her back. The tall guys dick fell out of her mouth but he didn't seem to get mad. He just moved forward and she started sucking him off again, though now giving him the same deep treatment she was giving Mister Hairy before.
The little boy was going at it furiously by then and he even stood up, but he was trying to keep his legs spread as he went towards the bed, so he looked a bit like a cowboy walking. There must have been a stepstool or something on the other side because he got up a bit above Iris and really started jerking like mad. He started coming and made sure to shake his dick really heard between spurts so that it got all over Iris's back and in her hair too. The guy behind her was very still by then and I could see more cum running down the side of her thighs. He just waited, probably letting himself go soft while still inside of her. Some guys really like that for some reason, and it does feel kind of nice in a way. Plus it always makes me giggle when it finally comes out with that soft 'plop' sound.
Anyway, the boy rubbed his dick with a fistful of Iris's hair for a while, just to make sure I guess. Now Iris was only concentrating on sucking off the tall guy, her head bobbing back and forth like mad. Finally the hairy guy in back pulled out and got off the bed. He told the boy to get dressed and he did too. But Iris was still throwing her whole body back and forth in her work on the tall guy's dick. And it worked too because he raised his arms and put his hands behind his head before starting to grunt. As more cum dripped from her mouth he moved his hips a bit to counter her moves. He winced and acted like it even hurt a bit with his breathing and stuff. So he was really sensitive but just didn't want to make her stop I guess.
But finally she started sucking him slowly again, just squeezing out the last bits with her lips, making a smacking noise each time she pulls her mouth completely off of the tip. It's clear that she didn't swallow him all like the other guy, which seemed weird. Then the tall guy held the sides of her head and gently pulled her head back, looking down at her tenderly. She looks back up at him with kind of curiously. "You okay?" he asked.
Iris smiled. "I'm good!"
He smiled at her and then helped her roll over onto her back. Then he laid down on top of her, or I should say that his upper body pretty much covered all of her. She hooked her heels around the back of his thighs and he leaned down and started kissing her hard on the mouth. She kisses back full force too. I guess he really was a repeat customer because we all know that most guys really hate to taste their own cum. But not this guy! He even paused to lick it off of her lips before kissing her again. Then he just lied on top of her for a while and she rubbed and patted his back, like he had done to her before.
Finally the hairy guys said that their time's up and they'd better go before they get in trouble. That seemed to get the tall guy's attention. So he quickly rolled Iris off of him and onto the middle of the bed. She sat up with her thighs spread, one knee bent, and held herself up with her arms as she leaned back a bit. He leaned in and give her a peck on the lips. "Same time next week, Irish Rose?" (That was her working name.)
"You bet!" Iris chirped while clenching a handful of the bedspread in her fist. She wiped her cunny and butt off with it as the guys left. I guess there was so much cum and stuff that she didn't want to spill any on the carpet while walking to the bathroom. (Skullboy said it costs extra if they have to clean the carpets.)
Then Iris just lied back on the bed and let out a deep sigh. And she started fingering her pussy! She just did that for a minute. I looked over at Skullboy and he was starting to look angry. Like I said, we were supposed to get back on the street fast after a trick. But she mumbled something about not getting any sleep and then finally jumped up and almost skipped into the bathroom.
Skullboy said it was gonna take her a little while to get all that cum out of her hair and stuff. "Besides, it's almost dawn so we might as well get going anyway." But then he took my arm so I looked him in the face, right in his eyes. Probably the first time since he'd punched me and stuff. "I need to go finish up business with those men, so go down to the basement and get Misery for me."
A heavy chill ran through me and it felt like all the blood rushed out of my aching body. Even though her working name was "Merry" she seemed like she'd never been happy a day in her life. Even though I offered her a nice room when she moved into the manor she insisted on living in the basement, in the dungeon no less. Even though she'd come upstairs for meals or sometimes to hang around she hardly ever spoke. She was always acting weird and saying things about pain and death. She scared me a little. And sometimes a lot.
He handed me a key and said that it was "just in case." I didn't know what he meant but I didn't say anything. He led me back into the hallway where the gentlemen were walking away. They were busy laughing and talking so they didn't even notice us down at the very end.
Skullboy pointed to where the stairs were and said, "Bring her back here to wait for Iris if she's not already done." I stammered 'cause I was afraid I wouldn't be able to find my way out from there, but he immediately raised one of his bony hands and turned up his nose (or would have if he had one)."Don't worry, silly. If Iris is already gone then Misery knows the way out too." I should have thought of that. "Go, hurry." Then he turned and started walking fast, calling out softly yet in a deep, gruff tone as he caught up to the customers.
When Skullboy says to move I don't wait around. So I went down the corridor and found the stairs. Even with the lights on at the bottom it was still kind of dark and scary, so I held onto the old pipe handrail hard and walked down one step at a time so I wouldn't fall. But I tried to be quick. Once down there it was all musty and dirty, and there were cobwebs all over the place. There was a big furnace with the fire inside burning brightly, its noise drowning out all other sounds, even my own thoughts.
So I walked around and found some big doors, most of them closed and padlocked. But one was half open, so even though I was afraid I pushed it aside and stuck my head in. Again, there was some light at the end of the hallway but it was still pretty dark and scary. Still I knew I had to hurry. I walked down the hallway and could finally start to hear something else. It was a soft moaning at first, like the sound of a slow painful groan, but then as I got closer I recognized Misery's voice. It was almost as if she was singing to herself a little, though it wasn't a very happy song if she was.
Finally I got the end and found a dank and smelly room with lots of pipes up, down and around all over the place. Some pipes were dripping and there were small puddles in places. A few of the leaks were really hot and even in the dark I could see wisps of steam coming from those puddles. Following the sound I walked around the corner, which was actually a bunch of pipes that clustered together around something before all going up to the ceiling or out to the walls on all sides. In that back corner I found Misery. She was hanging from a pipe that was about six feet in the air. Her hands and feet were shackled wide apart and she was totally naked, totally exposed. Even in the dim light her blue skin almost glowed in front of her gorgeous body-length black hair that framed nearly all but her hands and feet. Sadly, I could also see lashes, bruises and welts running across her stomach and hips, and I think even the insides of her thighs. I couldn't really tell but I think there was even some blood dripping down there too. Yet she was just staring down at the floor and singing her woeful song in some language I couldn't understand. I stood there for a minute not knowing what to do, but then I remembered the key in my hand.
I stepped closer and cleared my throat a little first. "Misery?"
The mournful girl raised her head and stared me right in the eyes. Even in the near darkness I could see my reflection in her huge dilated pupils. "Ruby," she answered in her droning but not unpleasant voice. She didn't seem surprised or anything, and actually for a second I though she even smiled a little. But maybe it was the lighting because she never smiled. "There's a stepladder over in the corner, and I think she left the key there too. Just bring them over and undo my hands. I'll take care of the rest.
So I did as she told me and went to the corner. The small ladder wasn't hard to see once I was there, but I had to kneel down and feel around on the ground for the key she wanted. There was no floor, just dirt, so I had to dig around and still couldn't find it. The smell of wet soil and mildew were bad enough, but I felt bits of things on the floor too and touching some of them brought up nasty odors, mainly the putrid smell of dead mice or something. We had them in the mansion once and had to use traps. Skullboy made Iris take them out to the garbage after they went off so I never had to get close, but I still smelled it. It almost made me sick, but the pain in my ribs and back reminded me to ignore it all and just hurry.
"It's okay," Misery finally called out. "Just bring the ladder and use the spare key." I was happy to grab the stepladder and run over. I quickly climbed up and clumsily opened the manacles. Without a word she took the key from my hand: she didn't grab it, but more like slipped it away from me before I even realized. But when I recovered then I was even more amazed how she was able to stretch all the way over to one side, I mean way over, to where her ankle was chained and unlock it.
I tried to take a step back and almost fell off the ladder. Once I got down and looked again she did something really eerie: With her legs still spread she stood up again but, without any dragging or hesitation, her free foot seemed to glide effortlessly over towards the one that was still chained. She floated to that side until her legs were closed and she was standing up totally straight. Then she simply knelt down, basically sitting on her feet, and finished freeing herself.
For a couple of minutes she was busy collecting the other chains, plus riding crops, a whip and other stuff that I couldn't make out. I just sort of looked around and then saw her clothes laid out, all neat and unwrinkled, on a table that was also uncharacteristically clean for this place. I reached out to touch her purple dress, to caress its velvety fabric, suddenly thinking then maybe I'd understand her a little more. But then I realized that my hands were still all dirty so I stopped. Still, for some reason I still wanted to touch it so bad.
I decided to forget it and turned away, but I found her standing face to face with me! She was still completely naked but didn't care one whit. "It's okay," she said, as if she knew exactly what I was thinking. I hesitated. And after a moment I really didn't know what she really meant. Then I found her hand on my elbow: again, she had been so swift and gentle that I hadn't noticed until she was turning me back around towards the table. She held my arm out as she slid her nearly transparent full-length veil off of the table and laid it over my forearm.
Then she slowly slid it over my arm. It was gentle as a spider's web and softer than even my favorite plushy. My whole arm tingled and I got goose bumps everywhere else. But she didn't stop there: she snaked it around my shoulder, across the back of my neck; she started walking around me, pulling the diaphanous shroud around my back and then, yet again, I found my right arm being held in the air as she continued circling me with it. I must have been under some sort of spell because I just stood still and held both of my arms out to my sides like that while she kept wrapping and pulling it all around me a few more times. With each pass the veil trailed lower and lower over my body until it barely caressed my bruised knees. Then it slipped away and she held it up between our chests.
Misery was in front of me now and, in a flash, she flicked it up in right in my face. But instead of making me wince it actually felt good, like a warm wet towel wiping across my face making me all calm. Then she wrapped it loosely around my neck, her hand petting my face softly through it as she did so. She was surprisingly tender and warm. Then she suddenly pulled the veil up from behind with both hands. Basically it went over my head and then I closed my eyes as it passed over my face again. It seemed like it was just for a second, but it felt really relaxing.
Then it got really bright and I snapped out of it. I don't know how, but when I opened my eyes Misery was already fully dressed with the veil trailing her as usual. The room was now all lit up by the small skull-shaped lantern hanging from her crosier. She must have had it hidden somewhere 'cause I don't remember seeing it when I was looking around. But now I could see everything, from the stone walls, the flecks of paint and rust on all the pipes, even the small stones, bits of wood and other things strewn around the muddy floor. I was even more glad that I got to work in the really nice rooms.
I was about to ask her something, but now I can't remember what. I just know my mouth opened but I never got the chance to speak because she suddenly said, "Okay, we're ready." And she said it almost sweetly, at least for her. She tilted her crosier towards the exit and instantly led the way out. I barely caught up by the time we made it to the furnace room, where it was too loud to say anything. Then she seemed to float right up the steps, so fast that I had to catch my breath by the time we got to the top. Only when I was breathing so hard from running up the stairs did I realize that all the pain from Skullboy beating me was gone. I looked at my knees and they were all better too.
Again I opened my mouth again to try asking her something, but nothing came out. Maybe I was so afraid of the answer that I made myself forget the question altogether.
At that moment Iris stepped out of the room, all clean in her short black top and tiny little white skirt. She had on horizontally striped black and white stockings that went most of the way up her thighs; they were held on by garters that clung snugly to her inner thighs, easily visible because her miniskirt was that small.
"We're done for the night. Skullboy wants us to meet him outside," Misery told Iris, even though I hadn't told Misery. But she always seemed to know stuff like that. Maybe she just understood Skullboy better than us, I thought. Or just wanted to believe.
"Okay!" Iris chirped as she ran back in and grabbed her working bag. Misery immediately started off again, leading us first back to my room to get my bag. I stopped to quickly wash my hands too, and then Misery led us quickly to the lobby.
When we got there Skullboy pushed himself up from the big overstuffed sofa and went over to the desk. Without a word the clerk got out my dark-red full-length coat and handed it to him, treating it very gently. Skullboy then helped me put it on while the clerk helped Iris into her plain gray overcoat. Then I started to pick up my working bag but Skullboy insisted on carrying it. Maybe he still felt bad about beating me up. I could have told him I was okay and stuff, but when he did even little nice things like that for me it made me feel really good, so I let him.
As we stepped outside Misery paused to pull her veil down over her front, as usual, and then moved to the back behind Iris. That left me and Skullboy in front. Though it was still chilly, the sky was mostly clear and my jacket kept me warm enough, so I knew we'd be walking all the way home today. That wasn't a bad way to end a hard night, or any night really.
As we started to leave I couldn't help but glance back at the dark alley. Even with the first gleaming of twilight and the bright light of Misery's lantern I still couldn't see a thing. I stopped for a moment, staring extra hard into its impenetrable shadows. I wondered if the man who'd ruined my dress was still lying there.
When I turned back around Skullboy was standing by my side. He smiled and held out his elbow, like the guy had. I smiled and took it. Even with Iris chattering and Skullboy cussing her out once in a while, I felt like I was on top of the world all the way home.
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The Dark Side of the Bright Side