The Degradation of Shelby Ann by Emma Cole

Chapter Twenty-Two

Shelby

My plans came to naught as the days wore on. Winston kept me buried in the room in the security hall where he subjected me to his most debauched sessions while Sasha and Marigold filled me with an ever-increasing amount of narcotics. I wasn’t sure my husband even knew how much they were forcing on me, but I was afraid to say anything or refuse since he’d left the task of my ‘compliance’ up to them. Sasha had seemingly been on my side, at least at the beginning, but after they were repeatedly used as little more than an appetizer to my main event, or as clean-up, she started to get as nasty as Marigold. I didn't know what else, if anything, they were suffering, but whatever the reason, they'd completely turned on me. And Milo, he was a new fixture whose appearance I dreaded every minute I was in there despite the lack of lucidity.

His father had demanded we make an appearance before more rumors started, so Dirk had randomly picked some over the last week. The first had gone somewhat well as it was at a theater and too dark to notice my haggard appearance that even make-up was having a hard time disguising. But the one from tonight hadn’t gone so well. And that was where I found myself being taken, yet again, after the shit show that came when Dirk decided to attend a holiday function.

“I didn’t do anything, Dirk. Stop!” Digging my heels in only resulted in a slap, and I knew that he’d blame me for the mark on my face.

He tried to avoid those so I could still fulfill my public duties as his wife, or so he had said, but I thought it was more to avoid Carter seeing them. He hadn’t been too pleased about the belt mark on my neck that might draw unwanted attention if anyone saw it. As for the Christmas party we had attended that evening, first Rafe, and then Carter had shown up. Dirk had rudely told his brother to mind his own business after Rafe commented that I didn’t look well and asked if I should even be there. Instead of causing a scene, Rafe left, but I had a feeling he called Carter because my absentee bodyguard had arrived shortly after. He’d quietly had words with Dirk about keeping his schedule updated so he could accompany me when I left the house.

It had pissed Dirk off badly enough that we'd left immediately, and Dirk had proceeded to snort whatever he had stashed in the back of the car that Milo had taken up to chauffeuring on the rare occasion we left the estate. I only hoped that I wouldn’t be required to make any appearances as my health was definitely declining. I was exhausted and sick to the point that I was only awake when Dirk forced me to be. Before Thanksgiving, there had been a pile of invitations to reply to, but most of them had gone unanswered since I'd spent the majority of my time either recuperating and hiding in my room or in the room where I suffered at Winston's hands.

"He's not here to save you," Winston snarled as he dragged me through the door. "He went right back to handling what should be my job while Father is away." At the rate he ingested the products that he’d peddled, I highly doubted my husband was in any condition to run anything but his mouth, but I kept my mouth shut on the subject, as I pretty much did everything else. He continued to rant while pulling me along. "Always taking my place, always taking what's mine." If he hadn't been such a psychotic, abusive piece of shit, I might have felt sorry for the creature he'd devolved into. The drugs had taken their toll on him as well, though I doubted he noticed or cared.

Without waiting for directions, I went straight to the bathroom to strip and handle the minimal business I needed to to meet Winston's demands. Since food wasn't high on my agenda anymore, it didn't take long, and I was waiting on the bed, naked, while he typed into his phone.

A few minutes later, Milo came in with Sasha and Marigold. It had become clear that they were being kept on the estate, though I didn’t know or care where, and Milo had taken up escorting them around when they needed to make an appearance or be sent away. They slipped off their robes, and it didn’t surprise me that they were ready to go—they always were, it seemed. But when Marigold came at me with the line-covered mirror and glass straw, I balked.

My stomach rebelled at the thought of the sickly sweet taste that would settle in my throat for hours. At the same time, I worried I would lose chunks of time as I had the last few times I'd taken what they'd given me. Almost immediately after, my heart had begun to race, and I'd wondered if I would have a heart attack and die while being fucked in whichever manner Winston and Milo preferred that day. I might not want to live as I was, but the very real prospect of death made me shy away and cling to life, so I covered my face and scooted away from the poison.

“Sir, she’s refusing. What would you like us to do?” Sasha addressed Winston, pulling his attention from whatever he’d been discussing with Milo. He hadn’t looked happy, and with his altered state, that was odd, so I guessed Milo had had bad news, and the glare he turned on me had ice coursing through my veins. I considered taking the straw at that point, but I didn’t think it would do me much good. Besides, I was petrified in place when Milo added his own amused stare into the mix. The man was fucking devious.

“Boss, I don’t think we need that,” Milo stated as Winston took his belt off. “I saw something in a video the other day that I’ve been wanting to try, and I think you’ll enjoy it, too.” His sly grin made me wish Winston would just use the belt.

Instead, I found myself in Winston’s favorite position—head down, ass up—with Milo holding my vagina open while Winton blew the powder into me. When they were finished, they left me be to get head from the women until they decided it had been long enough for the coke to work. It took longer than usual, but that didn’t really concern me. The lack of sensation inside and out did. My entire crotch was mostly numb, and I was kinda freaking out. They were going to kill me one day, likely soon, with their random chemical experiments.

Milo stretched out on the bed and patted his hip, his version of ‘climb on,’ and I slowly complied. “She’s dry as shit. Sasha, go get something,” he demanded with a grimace as he prodded my pussy, getting absolutely nowhere. I didn’t know why he didn’t start with it in the first place, who knew with Milo, but anytime the women used coke, or made me, they immediately used lubricant. I didn’t know the why’s of it, but it made getting off hard and getting wet harder. The only reason I even cared was to not have my skin torn up.

As soon as Sasha liberally coated Milo and roughly lubricated me, Milo tried again, succeeding in making me take him as far as he could physically go. There was a dull sensation in my abdomen that hinted at pain, but I didn’t even feel the usual stretch that accompanied sex with the huge man.

“Your turn, boss,” Milo called out to Winston who hovered behind me. But when he went for my backdoor, Milo stopped him and directed him to where he already filled me. “No, here.”

I couldn't see Winston, but a moment later, I felt a faint pulling sensation at my opening. “Dammit, Milo, I can barely get my fingers in there. How the fuck do you expect me to get my dick to fit?”

At that point, I struggled to move away. No way in hell were they both going to fit in there, numb or not.

“Hold still!” The slap to my ass had the desired effect, and after staring at Milo and admitting my defeat, I buried my head in the crook of his neck and waited for the inevitable. “Back out some, then we’ll push in together.”

Milo obliged, and Winston handled the rest, with a lot more lube, then they both managed to push just inside before finally working their way fully in.

“I think her pussy is making my dick numb,” Milo complained, but Winston didn’t care. They spent the next hour alternately fucking me and applying more lubricant until Winston ordered Sasha and Marigold to assist them in getting off.

I didn’t know what they did, but the moans that came from the men indicated it was something good, then Winston reached his peak with a shout of triumph a few minutes before Milo cursed through his. As they removed themselves, I slumped to the side, too afraid to look at the damage I was sure they’d caused, and dreaded when sensation would return.

* * *

It wasn’t long after that that Carter came in while Winston was yet again snorting a line, this time some pill that he’d crushed. I cringed when his gaze landed on me, but I didn’t bother to try to cover up. After all, he’d allowed them to treat me like this, so he could deal with looking at the aftermath.

“Get out!” Carter shouted at Sasha and Marigold, who scrambled off of the bed in the face of his fury. “What the fuck are you doing, Dirk? Have you gone completely insane? Your brother went straight to your father, and he is not happy with either of us after he found out you’re still using. Not to mention your games have gone too far with your wife. Straighten your shit up!” He went to leave as quickly as he’d barged in, and stupidly, a pang of betrayal hit me. He only showed up because Winston Sr. got on his case about the party.

But Winston stopped him as his hand reached for the doorknob. “Do you enjoy being my father’s lapdog? You could have just as easily called, you know? But I think you were more interested in my wife, weren’t you?” Carter turned to glare at Winston, but he didn’t move from his spot. “Feel free to sample the goods if you’d like, although they’re a bit used up this evening,” he crowed at Carter. He was fresh on his high, not likely to let anything go. “Actually, I insist on it.” And there went the amusement. I shivered at the calculated stare he challenged Carter with. I was slightly surprised that Milo stayed out of it, but the man wasn’t stupid either. “I want to see what was so great that my wife gave it up to you first.”

Carter’s eyes widened before they darted to me and then back to Winston again. “I don’t know what she told you, but—”

“Oh, do shut up. I found the picture of you two. Don’t try to lie about it now. Shelby and I have...come to terms with her perfidy.” More like he had come to terms, and definitely not good ones. “Now, pick a hole and get to it. I’d offer you Marigold or Sasha to get you in the mood, but you so arbitrarily kicked them out of my own goddamned room!” Winston moved to sit in a chair in the corner where he usually left his clothes, then dismissed Milo. Whatever he had to say, it didn’t include his closest confidante.

Milo appeared mildly annoyed as he jerked his suit back on, but he left with only a sneer at Carter.

“Dirk, I’m not having sex with your wife. Sober up, and for god’s sake, feed her. She looks anorexic.” Carter seemed to think that was the end of the discussion, but Winston upped the stakes.

“Do you know how I first came upon you, Shelby?” Winston mused, confusing the hell out of me but gaining Carter’s full attention. “I could tell you a story, but that wouldn’t be as interesting as if I told Father about his golden boy, now would it?” I vaguely understood that I was the threat, but I didn’t understand how. Yet Carter capitulated almost immediately.

“Fuck you, Dirk,” Carter snapped at my gleeful husband.

“No, that’s what I want you to do with Shelby. Her pussy is pretty torn up, but she likes it up the ass, don’t you, darling?” I still hadn’t looked, but an ache suffused my entire pelvic region, making me worry he’d done real damage that I’d need a doctor for.

“What the hell did you do, you deviant?” Carter asked as he came to check me out on the bed. When disgust crossed his features, I tried to move away, but Winston clicking his tongue froze me in place. When Carter gestured for me to spread my legs, I closed my eyes and slowly opened them, not daring to look when he started swearing. “You need help, Dirk. And you need to keep Milo away from her. She’s not one of your whores that’s used to being roughed up.”

I opened my eyes as I shut my knees together tightly, catching Winston’s shrug. “She’s well on her way to one, which is your fault. You should have kept your dick away from her.” He gestured for Carter to get on with it and picked up his phone, no doubt relaying something or other to Milo.

“Go clean up. I’m not touching you with all of...that on you.”

As I realized he meant the commingled cum from Winston and Milo, tears pooled in my eyes. He didn’t have to be such an asshole. I hurried as quickly as I could, the stiffness and ache between my thighs more than I’d thought at first. The numbness was rapidly dissipating, and I was afraid of how badly I’d hurt when it completely wore off. The shower was quick and to the point. There wasn’t too much pink in the water when I used the showerhead to rinse between my legs, but the gape was big enough to easily fit several fingers inside. Handling the tender flesh as carefully as I could, I washed until it was as clean as it was going to get, not that it helped close the hole up any, and I worried that my vagina wouldn't ever go back to normal. No wonder Carter had been disgusted.

With shame riding me hard, I dried off and did my best not to limp to the bed that had been stripped of the coverlet now piled in a heap by the door. Carter stood at the foot of the bed, fully clothed, with a bottle of lube in his hand.

“Make sure she gets off, Carter,” Winston commanded before he threw a microphone-shaped vibrator onto the bed.

With a sigh, Carter pointed to where he wanted me, and then, to my horror, made me take the same position Winston favored. I didn’t know if it was on purpose or not, but it still ate at my heart. I heard the jangle of his belt, then his zipper, before a ripping noise met my ears. I chanced to see what he was doing, and the sight of him rolling a condom over his length made mortification burn through me again. He thinks I’m dirty. Hell, I probably was dirty, but not in that sense, at least I hoped not. As far as I knew, the only people that touched me only touched each other, so it shouldn’t have an issue…

Thoughts fled from my mind as my cheeks were spread and cold liquid hit my ass to run down my taint and onto my throbbing pussy. But I was more stuck on the fact that Carter was going to fuck my ass. At the first push against my hole, I couldn’t stop the tears that escaped into the sheets. He didn’t make any sound other than the rasp of his thrusts in and out until he switched the toy on and reached around to get it into place, making me wince at the discomfort. When Winston came to me with the mirror and a line, I almost thanked him, grateful to get any distance from the trainwreck I was starring in.

“I don’t want that shit around me,” Carter barked, roughly shoving into me, making his balls slap my sore nether lips.

“Fuck you, Carter,” I gasped in pain, then took what was offered. “This is your fucking fault.” He stuttered to a stop and mumbled something I only caught part of, but the rest was lost to Winston’s cackling laugh.

“I couldn’t have planned this shit better. At least she hates both of us.” Winston went back to his chair to enjoy the show.

It took longer than I’d hoped, and I was covered in sweat by the time it happened, but when my orgasm hit, I cried out and clenched around Carter for all I was worth. The reaction might have been a bit over the top, but in my addled mind, it was fitting to punish Winston after he loaned me out. Let the bastard think that Carter did it better. He’d beat my ass at the drop of a hat or fuck it until I couldn’t walk, so what did it matter?

Carter couldn’t hold out though, coming with a grunt as he dropped the vibrator to buzz against my knee. I didn’t bother to move as I heard him pull his pants up and leave. When the door shut behind him, I finally reached to shut it off and glared at Winston. He didn’t say anything, so I turned my back on him, and surprisingly, he left too.

* * *

It was New Year’s Eve, and I lay in Dirk's bed where he'd demanded I go after cleaning the mess he and Milo had left on my body. He sure delighted in making me filthy, but he couldn't stand it after the fact. Since the Carter incident, when he was done with his debauchery, Dirk wanted his wife to sleep with him, where he could hold on tightly enough to smother me.

That night, my curiosity got the better of me. Maybe it was the drugs that still coursed through my system, or maybe I just didn't care at all anymore, but whatever the reason, I blurted out my suspicions.

"Why aren't you and Milo together? Why did you marry me when you're in love with him?"

His chest stiffened under my head, and I tensed right along with him, thinking maybe I'd regret asking until he finally answered. "There are just some things that aren't done in this family, and that's one of them."

I would have laughed at the hypocrisy, but really, it wasn't all that funny, considering what was allowed.

"Did you ever love me?" I couldn't help but ask.

"Why would you think I don't love you? I've wanted you since the minute I laid eyes on you. Milo did too. He was the one that found you, the one that found out Carter wanted you." His answer surprised me; I couldn't believe he was still so delusional.

"This isn't love, Dirk," I dared to retort, but he continued on speaking and took up running his hand down my hair in a soothing rhythm.

"It is for me, darling. I can't always have what I want, but I can have you. Carter has everything else—my place, my father's respect... He even tried to keep you from me. I hoped that the three of us could be happy once my father was gone and Carter was out of my life. Just me, you, and Milo, but you had to go and betray me with my enemy."

"That's not fair. I didn't even know you!" I protested, unable to follow that process. He didn't make a lick of sense.

"It doesn't matter. You're mine now." He acted like I hadn't even spoken.

"Why are you like this? Can't you just be the man I met? Surely you weren't always so hateful?" I didn't know where the courage came from to demand the answers or why he didn't blow up at me, but so far, I was getting away with it.

"No, I was normal once, if that's what you mean. But that boy, he couldn't survive in this world. Something broke in him, and he came to hold everything together. His rage is always there, simmering underneath until it needs an outlet, and then I can be me again when it's sated." He sounded detached, as if he were talking about another person entirely, and a shiver of fear worked its way through me. "Carter should be broken too. Father didn't spare him the details either, but maybe that's why Carter is the golden boy… He didn't break where I did. No, he embraced the life, doing everything asked of him, while I rebelled, wanting out until it was made clear that would never happen."

The information was too much yet not enough, so I pushed my luck further, finally getting the answers I'd wanted for so long. "Wait, your mom and his parents were killed in front of both of you? By your dad?" If it were true, I was on a merry-go-round of insanity with no way off.

But he still acted like he wasn't hearing me. "Mother died in that room," he whispered.

"She died in that room? The room? Dirk, seriously, what the fuck? I thought your mom died in an accident?!" There was something very, very wrong with this man, with this entire family. Not that I didn't already know that, but to take me in there after everything...

"Shhh, darling, you're going to rile him up again, and I'm tired. He might be satisfied if I let a few of the guards tear up my holes, but I think we'd both rather sleep."

His threat shut me up, but I couldn't stop thinking about children watching their parents get killed. Or why one would grow up to torment women in the same room after something so horrendous. And then the tears came—for myself because I was resigned to the knowledge that I was never getting out of this family alive, for Dirk and Milo never being able to live their own lives, and most of all, for lost little boys that had become monsters to survive. The unfairness of all of it was too much to handle.

Through my torrent of tears, Dirk calmly stroked my hair, never complaining once about the mess I made on his chest as I cried myself to sleep.

That was the one time I truly felt we'd ever shared anything real.