Reversal of Fortune Ch. 02

byAn Awful Cad©

I was beginning to wonder how I could pull back from this precipice and control myself, when suddenly we heard the garage door, signaling Harvey's return. Sherry flinched, but I held her firmly in place with the carrot.

Sherry turned to me pleadingly. "Please don't do this," she begged. "Just let me go upstairs and get dressed. I'll do anything you want..." I laughed inwardly at this. As if she wouldn't already do anything I wanted her to do.

"I think you already know that's not the way it's going to go, don't you Sherry." She didn't reply, but just bowed her head and stared silently at the floor. "Now. Let's get this show started."

I dragged the carrot from her ass with a plop and set it down on the counter. Taking her by the elbow, I led her into the living room and dropped down on the big overstuffed couch. I pulled Sherry down next to me and ordered her to unzip my pants and pull out my cock. It was, of course, fully rampant.

"Start sucking it, nice and slow. And whatever happens, don't speak or do anything unless I tell you to, understand?" I thought I saw a tear welling in her eye as she nodded silently and assumed a crouching position on her knees next to me on the sofa. I pressed her head into my groin and was treated to the incredible sensation of my cock slipping into her warm, slippery mouth. I guided her head up and down slowly; setting the pace I wanted her to take. Despite her apprehension, she settled into a deliberate rhythm, bathing my shaft in her slick saliva and massaging the pulsing veins with her tongue on every long, slow stroke. It was an incredible, luxurious suck and I was just contemplating how much her skills had improved in scarcely more than a week, when the door to the garage burst open and Harvey walked in.

Part 4

I had one arm splayed across the top of the couch and the other resting on Sherry's naked back, so I could feel her cringe when she heard the door open but I applied gentle pressure to remind her of her place. Harvey said hello and took a step into the room, then stopped short as he took in the lewd sight in front of him. I lounged casually on their plush sofa, smiling nonchalantly, while his naked wife knelt at my side, bobbing slowly and steadily on my cock, without so much as a glance at Harvey.

"Hi there," I said cheerily. "Come on in." I waved him into the living room and gestured to one of the other chairs as if it were mine.

Harvey looked like he had been punched in the stomach by Mike Tyson. His mouth gaped open and he moved like a sleepwalker. "Just like Sherry, when I first broke her," I thought to myself.

Harvey sank slowly in the chair and mumbled, "What's going on here?" to no one in particular.

"Oh," I said, as if I were just noticing it myself. "Well, your little slut wife was just giving me a blowjob. Like she does every day. You know, it was really a fabulous idea of yours to turn her into a cum-sucking whore," I stated matter-of-factly. "She's quite good at it, too, you know. Or maybe you don't."

I glanced at Harvey's face for a reaction. I could see that he knew something wasn't right with what I said but he was too transfixed by his wife's rhythmic cocksucking action to respond. I brushed back Sherry's thick black hair to give him a better view. He was treated to the sight of Sherry's wet lips stretched tightly around my glistening pole as it slipped back and forth in her mouth. Sherry's eyes were closed and she gripped my balls tightly as she pistoned her face up and down on my straining meat. "I'm sure Sherry would thank you, too," I said, "except her mouth's a little full of dick right now."

There was a loud slurping noise, like the last sip of soda through a straw, as Sherry momentarily broke the seal of her lips on my cock and her warm saliva cascaded down my shaft and onto my balls. Now it was Harvey's turn to flinch at the coarse sound. His eyes never left his wife's straining lips and bulging cheeks, even as he moaned audibly.

"This is awful." He wailed softly, again, to no one in particular. "This has got to stop. Stop this. STOP IT!" He made a half-hearted effort to be forceful but I just chuckled at him.

"Oh it's much too late for that," I told him. "Sherry's my little slut-whore now and there's no going back, I'm afraid."

I could feel an acrid sexual dynamic perfuming the air, like burning leaves on a fall day. Even while Harvey was in obvious distress at the sight of his wife naked and humiliated in front of him, Sherry was obediently maintaining her slow and steady pace milking my cock with her hungry mouth. She was sending a message with her very debasement, that Harvey was going to pay for his sins. "She's such a good little cocksucker, too." I told him. "Look at how focused she is. Nothing can tear her away from my cock. Go ahead, call her name and see what happens."

Harvey looked pained but he managed to croak out a small, strangled "Sherry." Sherry didn't so much as open her eyes.

"See, I can do this, and she just keeps on sucking." Although not large, Sherry's breasts were dangling pendulously due to her position. I reached around her torso with one hand and clamped one of her stiff nipples in my firm grasp. I twisted the hard nub roughly, eliciting a slight whimper from her. Then I yanked on her teat, pulling it down and stretching the tender flesh until I could almost rub her sensitive point against the rough fabric of the couch.

Letting go of her breast, I slid my hand along her back, caressing her soft ass and probing for her steaming center. I felt the heat even before I felt the first wispy hairs on her plump pussy. She was positively dripping. "Or this," I said, sloshing my fingers lazily in her overflowing pussy. "Or even this." I scooped up a load of her juices with my fingers and spread it over her exposed asshole. My fingertips circled the dimpled flesh, feeling every ridge of her tight pucker.

Surreptitiously I slid my other hand under her hair and onto the back of her neck, so I could control her when I made my next move. I jammed my long middle finger directly into the center of her clenched little aperture, sinking it into her ass up to the second knuckle. Sherry shifted a little bit on the couch, adjusting to this new invasion but kept up her steady sucking action. I wormed my finger farther into her rectum until it was sunk to the hilt and I smiled at Harvey. "Isn't that great? Even with a finger buried up her ass, she doesn't miss a beat."

I sat back, letting Harvey take in the scene and just enjoying the sensations. I established a rhythm: as Sherry bobbed on my shaft, I fucked into her ass with my finger on each downstroke, pushing her forward and driving my cock deeper into her throat.

"You've come at a very good time." I stated to Harvey. "I'm just about to fuck Sherry's ass for the first time." Harvey's eyes bugged out at that one. "At least, it's the first time for me. I don't suppose you've ever done her in the butt?" I inquired, but based on his reaction I already knew the answer. "Well, I guess we're all in for a treat then."

"You can't do that. Stop it right now!" Harvey spluttered, attempting something like anger and indignation.

"Of course I can, you stupid toad, and I'm going to enjoy it too. Let me ask you this: what did you think was going to happen when you sent her over to settle your debts without any money? Did you think she could work it off by babysitting? Even you can't be that stupid. No, of course not. You were turning her out as the neighborhood whore. But you're a lousy pimp, my friend. A wife for a window? Such a deal!

"But enough talking already, I've got an anal cherry to pop."

"Wait!" Harvey shrieked, as I started to stand up. "This has gone far enough. I'm calling the police."

I stopped, fixed Harvey with my coldest stare, and gave an exasperated sigh. "Harvey, Harvey, Harvey," I said, shaking my head. "If that's how you'd like it, go ahead. And while you're doing that, I'll be on the phone too, calling Sherry's parents to let them know that you've turned her into a whore for your benefit – that she's been sucking a stranger's cock every day for the last week because you won't pay your debts. How does that sound?" I was glad I still had my hand on Sherry's neck, because she tried to protest that one. I held her firmly in place, so that my cock muffled her protestations. I had a hunch that Sherry's parents, aside from being general battleaxes, were probably giving them a substantial amount of money and I could see from Harvey's face that he was calculating exactly how devastating such a revelation would be. He slumped back in his chair, frozen in mid-tirade, and I knew it was over. They were both mine.

"No? You don't want that?" I asked rhetorically. "Alright then, we're agreed: your wife is an anal whore. Now, where were we? Sherry, get up. You go here, over the edge." I patted the arm of the sofa to show where she was to bend over. She stood up, letting my cock drop with a wet slap against my belly. Brushing her hair out of her face, she started to position herself at the end of the sofa. Her face was the most erotic mixture of anxiety, trepidation and defiance I've ever seen.

I stood up as well and moved behind her. Harvey and I both had a perfect view of Sherry's ass, draped submissively over the arm of the sofa, with her furry snatch glistening wetly and peeking out from between her legs. "That's perfect!" I said to no one in particular.

"Sherry, show us where you want me to put my cock. Go on. Show me!" Slowly but without hesitation, Sherry reached back and grabbed each of her plump asscheeks in one hand and pulled them apart, bringing her wrinkled brown sphincter into view. It was exquisitely obscene, beyond even my wildest fantasies.

As Harvey and I both stared at Sherry lewdly exposing her tight virgin anus to be violated for the first time, I had another fiendish idea. "Harv – since this is Sherry's first assfuck, we might need to do a little preparation first, so it doesn't hurt too much. Think you can handle it?"

Harvey looked stunned. "What?" he asked incredulously. "What do you mean, what do you want me to do?"

"I don't know. It's up to you, but if it were me, I'd probably get it nice and wet, so my cock slides right in."

"You mean lick it?!? I can't do that!" He protested lamely.

I gave another sigh. "Of course you can," I admonished. "But it's up to you. If you don't care how painful it is for her, then skip it." Harvey's eyes were wide and panicked, as he futilely searched for a way out. I gave him a gentle push so that he was right behind Sherry's upturned ass and smiled as he slowly sank to his knees in front of her exposed asshole. Hesitantly, he stuck out his tongue as far as it would go and cautiously touched the tip of it to her taut asscheek, as if it might explode on contact.

"That's not going to do much there," I scolded. "Go on, lick her asshole. Get it nice and sloppy. Work your tongue up inside and lube it up for me." He shivered involuntarily and started out slowly, cautiously poking her sphincter with his wet tongue, but before long he was swabbing her anus as if it were a delicious ice cream cone. Silently, I wondered if it tasted of carrot.

"Much better," I encouraged, as I stripped off my clothes in final preparation to mount Sherry's ass. "You're a fine ass licker." And just then, I had the most fiendish idea yet...

"You know Harvey," I said slowly, "There's one more thing that needs to be prepared before I can shove it in Sherry's ass. Come over here and get me ready."

Harvey froze, with his tongue buried up Sherry's shit pipe. He lifted his head but did not turn to look at me. "I can't do that. Please don't make me do that," he begged.

"Stand up, you sniveling asslicker!" I barked. "Drop your pants. Show us what you've got in there."

Harvey obediently slid down his sweatpants to reveal a pair of white BVDs, covering an obvious erection. "Those too. Now!" Harvey dropped trou and out popped his stiff prick, standing at full salute. I was delighted to see that, although it wasn't tiny, it was noticeably smaller than mine, both in length and girth.

"Look at that, Sherry." I said casually. "Look how turned on he is by the idea of tasting my cock. I always knew he had faggy tendencies." I grabbed my stiff cock and waggled it in Harvey's direction. "Come on Harveeeey," I said in my most fey voice. "Let's go, time's a wastin'. I've got places to go and sphincters to hoe." I chuckled at my own bad joke and looked at Harvey, staring transfixed at my cock. "On your knees," I growled, in my sternest voice, snapping Harvey out of his trance. He sank to the floor, looking beaten.

I stepped up to him and thrust my pole in his face. Afraid to touch it with his hands, Harvey stuck out his tongue and tried to swipe at my bobbing shaft. "That's weak, you pussy! Show your wife how much you love her by lubing up the cock that's going to plow her ass for the first time."

Stung by my words, Harvey reached out with one hand and steadied my cock daintily with the thumb and forefinger of one hand. I saw that Sherry had twisted her head around to observe the action, still spreading her ass cheeks wide with both hands. Harvey began to lick my cock with long flat strokes of his tongue, trying to deliver maximum saliva with minimum contact with my pole. But when I saw that the underside of my cock was resting on the surface of his tongue, I thrust forward, sliding my pole into his mouth and ending that plan.

Harvey didn't pull away and I began thrusting slowly back and forth in his mouth, fucking his face as he sat there passively. I observed that his ears were bright red, presumably out of embarrassment. "Mmm. That's good!" I said in mock surprise as Harvey began sucking more actively. "Your husband's a good little cocksucker. I think he likes it too. I tell you what Harvey, or should I call you 'Harriet?' I'll offer you a choice. Since you like to eat dick so much, you can save Sherry's ass, literally, by sucking me off. If you swallow my load, I probably won't be able to fuck Sherry's ass, at least today. If you don't like the deal, it's no problem. Just say so and I'm ready to ream her ass right now."

I could see him weighing the distasteful options and I was impressed when he fed my cock back into his mouth and started sucking away, although whether he was motivated by lust or a bizarre chivalry, I couldn't say. I had no intention of letting him distract me from his wife's virgin asshole, however, so after a few seconds of his mouth action I pulled my cock from his mouth, leaving his lips pursed in the shape of my shaft and a look of total surprise and humiliation on his face. "Time's up," I said gaily. "Time for the main event!"

Part 5

I left Harvey on his knees in shock, and stepped up behind Sherry where she lay bent over the couch. She had been twisted around, watching her husband willingly suck cock like a one-legged whore, but when she saw me move into position with my hard cock in hand, she closed her eyes and turned away, gritting her teeth in preparation for the impending assault on her anus. She was still holding her asscheeks spread wide, so I slapped my shaft against her puckered hole, causing her to jump in surprise and knocking some of Harvey's saliva into her asscrack. I rammed my hand underneath her body, sliding my thumb into her steaming twat and sliding my hand forward until I pinched her swollen clit between two fingers. At the same time, I used the thumb of my other hand to spread the saliva around her tightly clenched sphincter.

I had a moment of doubt about the task at hand. Her asshole seemed impossibly tight and I momentarily considered what my fall-back plan should be if I could not fit my cock inside. However, as I massaged the bumpy surface, her anus began to relax little by little, drawing my thumb in deeper with each stroke, until soon it was fully ensconced in her backside. It was show time.

I withdrew my thumb from her tight cavity and grabbed my cock, moving it into position like a general bringing his artillery corps into battle. I paused to prolong the tension. It was perfectly silent, like someone had just put us on "pause." I moved forward until the tip of my howitzer was just brushing the wisp of hair around her sex. I looked over at Harvey. He was staring slack-jawed at the spot where my cock disappeared between his wife's legs. I almost laughed.

To throw them both a curveball and because I needed some more lubrication, I slid my shaft through her wet furrow and into Sherry's steaming cunt. She let out a sound somewhere between a whimper and a sigh. With a few strokes to coat myself in her juices, I pulled out and placed the head of my cock at the entrance to her dark hole.

I changed my position to improve the angle of my penetration and began to bear down. Sherry squirmed but there was nowhere for her to go – she was pinned between my cock and the arm of the couch. For a moment it was a stand off. Her rubbery pucker strained, bent, but did not give way under the force of my blunt assault. I continued to apply pressure however, and suddenly her sphincter parted and the crown of my cock popped into her anus. I truly felt like a king as I savored the tight grasp of her most private orifice.

I pressed forward and the three of us groaned simultaneously as my cock slid into her rectum for the first time, although each for very different reasons. I felt an incredible rush of adrenaline as I watched my shaft steadily disappear into her backside until I was fully sheathed inside her colon. Sherry gave one long, low, keening wail as her back passage opened to accept me into her depths and I continued my steady thrusting. Harvey looked stricken. His eyes were glassy and I thought he might faint.

I set up a steady rhythm, pounding her asshole like a well-oiled pile driver. I thrilled at the sight of the undulating waves of assflesh produced as my hips slammed repeatedly into her rump. Sherry was still using both hands to spread her cheeks wide for my benefit, but she was tilting her pelvis back and forth, apparently in an effort to grind her clit into the upholstery. She lay face down on the seat of the sofa with her head turned to the side, giving me a perfect view of her tightly closed eyes and gaping mouth. I watched as a sequence of tiny vibrations began to take over her body until she was consumed by a series of giant, wracking spasms.

I could feel my own orgasm approaching rapidly. I wanted to hold it off and prolong this incredible feeling, but I was unable to pull myself "out of the moment." It was simply too exciting: taking Sherry's anal virginity while Harvey looked on helplessly, ruthlessly plundering her ass until she orgasmed with her asshole skewered on my driving shaft in front of her uptight loser of a husband.

Sherry was gripped by another round of tremors as I continued to pound away at her ravaged asshole. "That's right!" I hissed. "Again!" I watched a drop of my sweat fall and spatter on her back, just above where my hands were sunk into her hips. That and the seemingly constant spasming of her clenching sphincter set me off and I erupted with a roar, pouring my seed into her ruined rectum.

Now it was my turn to be consumed with tremors as I filled her ass with great pulsing surges of my semen. I erupted again and again, and the exquisite tightness of her clutching bowels eased slightly as her back passage filled with my lubricating paste. I thrust into her a few more times and then fell forward in one final climactic lunge, sinking my shaft as deep into her intestines as it would go, determined to shoot my spunk directly into her stomach if possible.

I lay across Sherry's back, regaining my breath and senses, and could feel Sherry beneath me heaving gently as she went through the same process. I remembered the other player in our drama and looked over at Harvey. He was slumped in a chair, staring at us with the same vacant look as before, only now he had his swollen cock gripped firmly in his fist. He didn't appear to be stroking it, but from the looks of the pre-cum weeping profusely from the tip, he wasn't far off.

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byAn Awful Cad© 10 comments/ 125227 views/ 5 favorites

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