The Degradation of Shelby Ann by Emma Cole

Chapter Twenty-One

Shelby

By the time I was finished with my preparations and waiting on the bed for my husband, I was exhausted. I'd even had a quick shower to wash off the sweat that had poured from me when I'd had to hold the hated solution. Unfortunately, I was so tired that I actually nodded off, only to be rudely awoken by Winston.

“What the fuck did you do, Shelby?” he yelled as he pulled me from the bed. “Which one of them gave you a phone?”

Shaking my head in the face of his wrath, I pulled at my arm to dislodge his pinching grip. “I didn’t do anything!”

“Tell that to the deputy out front, Shelby. Someone called in a welfare check on you!” he all but spit at me as he took a robe from the closet. The brief peek inside showed more of the same...and a whole lot of other things in clear totes and on shelves that I wasn’t the least bit interested in becoming acquainted with.

“I’m telling you, it wasn’t me. I haven’t even been alone to do anything! And Marigold is a bi—” I cut off at his stern stare as we left the room, hurrying toward the front of the mansion. “She would have told on me,” I finally finished.

“We’ll find out who it was, and they won’t care for the consequences, I can tell you that. Don’t think that the police can save you, anyhow. It might delay the inevitable, but I’d get you back and make you pay for it tenfold.” His voice was a low hiss by then, but I was so used to his rants that I only listened with half an ear.

Even as we neared the front door, he continued to threaten me. I didn’t doubt his family's reach; it was why I hadn’t bothered to report him before. Families like his paid what was necessary to get their way... It would have been suicide to try it.

Before we rounded the corner that led to the foyer, Winston put on a smile, straightened my robe to cover as much skin as possible, then laced his fingers through mine to tug me into view of a uniformed man.

“Officer, as you can see, my wife was in the middle of a nap, but she’s quite fine. Just as I assured you.” He lost some of his joviality at the last bit, making the officer and me both stiffen.

"Of course, Mr. Hamilton," the young man replied nervously. "Just have to be sure, ya know? Seems there was some confusion on the part of the woman that called in. I just spoke with my captain, and he assured me the matter has been handled. Sorry to trouble you folks. Have a nice day." The officer had backed up to the door as he spoke, nodding along with his apology, until he was close enough to open it and disappear before any of us could respond.

Dread pooled in my gut as Dirk turned to directly haul me back in the direction we had come. Throwing a helpless look at Jerry, who appeared angry yet remained tight-lipped, I followed my deranged spouse.

"Dirk, I didn't have anything to do with that. I—"

"Just shut up, Shelby. I'm tired of hearing how nothing is your fault. I hope you're happy. You probably got that man fired, if he's lucky, and you're going to learn to obey me as your wedding vows promised, or suffer the consequences." He continued to rave until we were back to the room with Sasha and Marigold, and I didn't bother to contradict him. It wasn't worth the escalation it would bring.

Strangely enough, I was still scared to death of what he would do, but a sense of detachment had taken over. My body could only handle the whiplash from being doomed to a reprieve and back again. As the door shut, I stood there, numbly surveying the women that lounged on the bed and wondering what the point was to any of it. The stinging slap to my silk-clad behind reminded me that it didn't matter if I saw the point in it. All that mattered was what he wanted. With that thought firmly planted in my mind, I shrugged the robe off and left it where it fell, not caring if it pissed Winston off. It wasn't like I was there of my own volition, so really...it didn't fucking matter what he did in retaliation.

"Get on the bed, Shelby. I want to see if you followed instructions, or if I have to get my belt out before the fun can begin." Winston had already removed the accessory and set it aside as he undressed, but even that threat didn't have much of an effect.

I obeyed his command, but only to sit on the edge and not a thing more.

"I said to get on the bed. Now!" he snapped as he came forward, his dick hanging at half-mast and cruel intent fairly radiating from his entire being.

"Am I not sitting on it, sir?" I dared to say. My rebellion resulted in Sasha and Marigold edging away to get out of the danger zone—Winston appeared positively apoplectic. It made my heart triple its beat, but my soul sang with the knowledge that I wasn't so beat down that I had completely lost my self-respect. Maybe my self-preservation, but I was tired of taking his shit and didn't care.

"Hands and knees before I whip the skin off of your ass for sassing me!" He didn't have the belt as he advanced, but a frisson of fear worked its way through my rebellious bravado.

Why I taunted him further, I didn't know, nor where the gumption to do it came from, but as I moved into position, my tongue darted out to lick dry lips, and I delivered the words that burned in my mind. "If you wanted to order me about like a dog, you needn't have married me. You could have just gotten a pet."

I braced myself for the burning slap of leather that never came as I sneered at the women who couldn't contain their gasps at my backtalk. But the loop of the belt as it came over my head and tightened around my neck, trapping my hair around my face, dashed the last of the insulating shield.

As adrenaline raced through my system, my air was cut off, and I reared up onto my knees while I tried to loosen the makeshift noose. "Dogs get trained, Shelby, but I'm happy to treat you like a bitch and bring you to heel," Winston all but snarled in my ear.

He gave the leash enough slack to let me breathe before placing a hand between my shoulder blades to shove me forward until my face was in the bed and my ass in the air. As I coughed and tried to sit up enough to get more air in my lungs, Winston gripped the nape of my neck to hold me in place. I barely noticed the stinging from my scalp where my hair pulled as he spread my cheeks with his free hand to expose my back entrance. Instead, I was too busy trying to breathe and clench against the broad erection that came to rest against my pucker. Not that it did much good when he forced himself inside.

A guttural scream of agony erupted from my abused throat as he breached the tightened ring with what felt like a burning rod intent on causing the worst tearing pain I'd ever been subjected to. Yet my cry was cut off as he yanked on the belt, tightening it again and pulling me back to impale myself on his still advancing member until his hips met mine and he could go no further.

My body futilely twisted away only to have Winston's weight come down to pin me to the bed while my stomach heaved as a result of the tortured nerves in my backside being so violated. Nothing came up, not that it could have, but my mouth watered just the same as I cried into the bed when Winston began thrusting in punishing strokes.

He dropped the belt to grip my hips, using the heels of his hands to spread me open and take me deeper so that I shrieked with each penetration and eventually threw up the phlegm that had built in my throat before losing myself in a haze of misery. Until he latched on to the back of my neck, biting down without mercy before leaving a series of the same at random, earning more cries of pain from my waning vocal cords.

When it was over, his erection having swelled and throbbed within me to release his seed, I moaned in misery and tried to crawl away. He let me, lifting slightly to accommodate my escape, but the removal of himself was enough to set my ruined hole burning anew. I fell onto my side, his hot ejaculate trickling out against my skin, and moaned when he slapped my ass with a declaration of his own.

"That's my hole now, Shelby, and don't you forget it." I couldn't find the will to open my eyes when I heard his muted footfalls move away from the bed. "Marigold, clean her up," he demanded a second before the bathroom door shut.

More tears came as his whore licked at me like I'd done to her, and I tried to find a place to go that was anywhere but there.

A short while later, Winston left after dismissing the women, but he told me to stay where I was. When he returned, it was with a photo from the night we got engaged, which had previously sat on the desk of his office.

“Since you’re so fond of keeping mementos, here’s one to remind you of what you could have had if you had bothered to try to be a good wife...and not betrayed me.” He placed the frame on the bedside table and left. I cried myself to sleep next to the picture of him smiling up at me from his kneeling position and my own happiness after I accepted his proposal.

* * *

Winston continued to claim 'his hole' for the next several days, days that I could barely stand to sit on my bottom or even attempt to use the bathroom. Thankfully, Sasha had a few remedies that made it more bearable, if not more palatable, and Winston's attention ran to her and Marigold just as frequently as it did to me. He also directed and watched, which allowed for more time to heal in between sessions when he had exhausted himself and couldn't get it up again. I worried that the bites he'd left behind would scar, as a few had scabbed over, but they were just another physical reminder of the hell he put me through.

He and the women indulged in snorting crushed pills and lines of powder from baggies, but I adamantly refused when offered, unable to stomach the idea of feeling like I had before, even if it would give me a way to temporarily escape from my life and husband. Winston, though, he couldn't seem to get enough of the stuff. He alternately became nicer, or even more cruel, and it was a crapshoot of which way it would go at any given time. On the third day, he ran out of patience with my refusal.

"I'm tired of the cold fish routine, Shelby," he complained as he stretched my ass on his dick. "It's time to spice things up, I think, and I'm not taking no for an answer."

He held my head tightly by my hair and stayed buried in me as Marigold presented a mirror with lines on it and held a glass straw to one nostril while she plugged the other side. I contemplated blowing it off of the reflective surface, but the image of myself came into view. I already looked wrecked, with bruised skin and circles under my eyes. The stripe on my neck was starting to yellow at the edges, but the picture I presented was one I didn't want to face, nor did I want to deal with his wrath, so I gave in, sucking it up into my sinuses while wincing at the immediate burn.

But my body soon relaxed and became loose to the point it didn't hurt so bad. I rode the wave of the high, intent on not coming back until I had to. If only my intent had been enough to avoid Winston, but sadly...it wasn't.

He pulled out, I thought to move on to one of the others, but instead, he demanded I flip over and hold my legs back until they were nearly to my ears. Even through my high, trepidation slithered through my body when he approached with a double-sided dildo. I wasn't that naive that I didn't know what it was for, and I dreaded the thought of either end going in my ass. At least Winston used lubricant before pressing the first of several thick balls into my anus, not that it obliterated the pain that accompanied their entry.

"Behave, and I'll make you like it. Fight me, and I'll make sure it hurts." It was his only warning as he filled my back passage until the flat base settled against me to keep it in place.

I expected Sasha or Marigold to climb on the other end, so the shock of Winston turning and lining the smooth tapered end up with his own backside was enough to penetrate my chemically-induced fog. The pressure it put on my own hole was highly uncomfortable, and I couldn't help but watch in fascination as he impaled himself without pause on the girth of the long toy, settling his cheeks against mine with a faint grunt of pleasure. This isn't the first time he's done this…

"Sasha, attend my wife. Marigold, put your mouth to good use," he ordered as he began to work himself on the black rod. I never imagined Winston would be interested in what he did to the women around him, but my mind was too fluid to fully contemplate the implications it had come to.

Marigold moved in front of Winston and out of my sight as Sasha climbed off of the bed for a moment, then returned with a bulbous-headed vibrator that she put straight on my clit, using its highest setting. I couldn’t help the gasp of ecstasy that left me as she worked it in firm circles until my nub stood painfully erect and throbbing from intense arousal. With the pinching push and pull of the balls inside me helping to drive me crazy, I came with a high-pitched cry of pleasure as my internal muscles clenched on emptiness and my ass gripped the toy tight. Sasha shut the vibrator off, taking the now-slick head from my clit, much to my relief, though it didn’t help the ache in my backside that intensified now that I was spent.

“That’s it, slut. I knew you’d like it,” Winston panted as he turned his head to meet my eyes, his own hooded yet bright from lust and drugs. He picked up his pace, holding my gaze while he rammed himself into Marigold, then back onto the dildo, until he stuttered to a stop and reached his own climax.

When he lifted off of the dildo, it left a slight looseness to his asshole, making me consider how my own must look after so much stretching. It wasn’t a pleasant thought, but the things that flitted through my head right then were uncontrollable at best. When Winston removed the large beads, I got to see my own gaping hole and quickly tried to drop my legs, hiding the orifice that didn’t quite close while hoping it would eventually go back to normal.

“Uh-uh,” he tutted, “not so fast. I told you I had a surprise.” To my utter mortification, drugs or no, Winston went to the door buck ass naked and opened it, poking his head into the hall. Only the fear of what he’d do kept me in place as Milo followed him in, gaze intent on my exposed nether region.

“Damn, boss, you gave it to her good,” the giant of a man praised with a smirk and a whistle of appreciation.

“Got her nice and broken in for you. You can use one of the whores if you’re not quite ready to indulge yet.” I had a hard time comprehending what Winston was saying, unable to believe he’d truly offer his bodyguard free use of my body.

“Winston, please, may I go?” I begged, staring directly into the face of my tormentor. He’d gone too far this time. It had already been bad enough, but… “Please, don’t do this.” It came out in more of a whimper than the steady tone I’d aimed for.

“Shelby, darling, don’t embarrass me in front of Milo. Remember, I’ll get the belt if you give me any trouble, and I don’t think you’d appreciate me letting Milo wield it. He’s a touch more...rough than I am.” His thoughtful expression turned downright challenging as he stared me down, and my fingertips dug into my ankles, leaving indents from my nails.

I watched helplessly as Milo stripped, revealing his toned and cut body. His striking green eyes, paired with his dark skin tone, framed his Creole heritage well, and once again, the mystery that someone so beautiful could be so cruel baffled me. But I’d never forgotten Jerry’s advice to stay away from him, and now I was stuck directly in his crosshairs. When he got to his underwear and revealed the partially soft erection, I could feel the blood drain from my face as I unintentionally made a noise of disbelief in the back of my throat. The man had a penis bigger than I’d ever seen, even in the limited amount of porn I’d watched with my tittering classmates on the rare sleepover in highschool.

Milo grinned with prideful glee at my terror and took his dick in one hand to squeeze and pull on it until it swelled and lengthened even more. “I don’t think I’ll need the ladies’ services tonight, boss. Right now, your pretty little wife is doing it for me.”

Winston dismissed the women, who immediately grabbed their things and left the room before they were even fully dressed. That alone let me know that I should fear Milo. They had a healthy amount of it for Winston, but they didn’t react to him in the same way.

As soon as they were gone, Winston grabbed me by my hips and pulled me to the edge of the bed before moving behind Milo, encircling the big man with his arms and taking over the stroking of his horse-sized cock. “Do you want to try her pussy first? It hasn’t had any attention today,” Winston asked quietly, but Milo shook his head and stared with blatant interest at my back hole before dipping a finger into the red and swollen ring.

“This will do just fine, boss. I’ve been waiting to wreck this tight ass, but it’s even better sloppy—less chafing, if you know what I mean,” he teased as he removed his finger.

“Behave, Shelby, don’t forget,” Winston warned me before he guided Milo’s broad tip to my ass. A muted whine accompanied the wince I couldn’t hold back as his blunt head tried to gain entry, then stalled as the unaccommodating muscle refused to stretch further. “Push out, or I’ll force it in.” I held my breath as I flexed my sphincter and bore down against the massive intrusion, only to have it expel in a rushed shriek when Milo breached the thick ring and Winston continued to feed the rest of him into my protesting tunnel.

“Please, stop, please,” I cried out as Winston let go so Milo could press home.

I released my legs to kick against his chest when he hit something inside of me that made my body try to expel him in an automatic reflex. There isn't enough room. He's going to break me! But Winston didn't care that I begged or struggled; he delivered a slap to both legs that had me gripping them tightly to my chest in a bid to avoid even more agony at their hands.

“Oh, fuck,” Milo groaned as he closed his eyes. “I bottomed out, boss.” Then his eyes popped back open to stare at me in anticipation as he asked for permission to hurt me. “Can I force it? She makes the best sounds when I hit the curve.” I didn’t know what ‘curve’ he was talking about, but I obliged him with another moan at the agony he caused when he bumped the spot again.

“Not today, Milo. I don’t want to cause damage that will draw attention. We’ll work on getting her open another time.” Winstion’s answer both relieved and horrified me, but there was fuck all I could do about it. I considered asking for more of what he’d given me earlier to dull the pain and let me escape from my grim reality, but I couldn’t quite bring myself to do it. “Fuck her ass while I take her mouth. She has more than one hole that needs work, and her gagging should feel mighty nice on your end as well.”

At that announcement, Winston moved to straddle my head and pull my legs back again, leaving me helpless as they found their pleasure in my pain. With every deep thrust from the men, my throat protested, or my bowels did, and soon enough Winston had his dick buried to the hilt while Milo did his best to bore out my backside. I didn’t know how to cope with the addition of Winston’s ‘surprise’ and considered making plans to run...or take my chances and attempt to kill them both.

* * *

Carter

My plans were coming to a head, but not fast enough to prevent Shelby from taking the brunt of Dirk's rage. With each new development, I turned his father against him, but it also escalated the violence he dished out.

Even the one-time whores that would come and go at Dirk's whim were now kept just to trot out for his use before being cooped up again. They didn't know it yet, but their lives were over. Hell, he was even letting some of the other guards have a go at them, and that raised other concerns.

Besides tongues that might wag, they could inadvertently give Shelby something that couldn't be fixed. I didn't care about the whores or Dirk and Milo, but I did care about the woman they were destroying.

With a sigh, I closed out of the video feed as Milo forced himself on her. I couldn't stand to listen to her pleas and screaming anymore. I just hoped that one day she'd forgive me for the part that I played in all of this.