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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.


Tags: Emma Cole Dark