Reversal of Fortune

Reversal of Fortune - Chapter 2

M/F, MMF, Oral, Anal, Mast, Veggie, Cheat, NC, Reluct

This story is the continuation of Reversal of Fortune Ch. 1.

Disclaimer: It’s porn. Don’t read it if it might offend you, if it's illegal for you, or if you have an actual or mental age of less than 18.

* * * * * *

After our climactic orgasms, we both sat there silently, literally and figuratively drained. At least I was literally drained. She had a belly (and face) full of my hot semen. I handed her a sock to wipe the sticky mess from her face. I watched with amusement as she attempted to clean herself up. Resuming my dominant demeanor, I told her, “I guess you can be a good girl when you try. That was a good job there.” I said, fully meaning the pun, although I don’t think she got it. “That’s all for today. We can deal with the window tomorrow when I have some more information.”

I told Sherry to come by in the morning, when I would have spoken to the insurance folks and the window repairman. I wasn’t sure exactly what Sherry would do, or even what I wanted to happen. This dominance thing was new to me. I guess I sort of thought that she wouldn’t show up, or that she would send Harvey and that would be the end of it. But I was wrong.

At ten the next morning, there was a knock on the door. The kids were at school and I opened the door to find Sherry standing there. She was by herself and was dressed in a conservative, high-necked, long sleeved blouse, buttoned down the front, and an ankle-length black skirt. Her eyes were cast down at the floor and she was nervously wringing her hands in front of her.

I led her to the living room and offered her a drink, which she declined. I poured myself a cup of coffee and sat down across from her seat on the couch, but so close our knees were almost touching. I felt relaxed and confident. My destiny had literally knocked on my door. I knew that despite her attempt to conceal her sexuality behind prudish clothing, she had come back to be my obedient servant, ready and willing to do anything I asked of her.

“Sherry, I’m afraid it’s bad news.” I stated ominously. I was pretty sure our new relationship wasn’t really about the window, or her ability to get it fixed, but it seemed to trigger a certain response from her so I launched into the details of how much it would cost to get the window repaired and that with the deductible on the insurance, it would be quite expensive to replace. As I recited the cold, hard (somewhat exaggerated) facts, I reached out and began unbuttoning Sherry’s blouse. By the time I finished, her blouse was open to her waist. Her eyes were closed; she was breathing heavily as I slipped the sheer fabric off her shoulders and unhooked her bra to expose her pert breasts.

Admiring her exposed flesh, I ran my fingernails lightly over the soft mounds of her chest, drawing an involuntary shiver from Sherry and stiffening her nipples to hard little points. I pulled her forward off the couch until she knelt on the floor in front of me. Unbuttoning my pants to release my throbbing shaft, I grabbed her head and slowly fed her my engorged stalk. I wrapped my hand around her head, feeling her dark, silky hair cascading over my fingers and roughly fucked her face until I came deep in her mouth.

This time she did a much better job of taking my load, and afterwards I looked at her, kneeling on the floor between my legs, panting slightly. Her mouth was open and her lips were glossed with a shiny mixture of spit and my cum. She sat immobile, with her eyes averted, as if she was waiting for something. I had a pretty good idea what she wanted. “Stand up.” I ordered.

She was an incongruous sight as she stood for my inspection. Naked from the waist up, chest heaving slightly from her exertions, cheeks flushed and lips wet with my man milk, while down below her long black skirt covered every inch of her flesh and looked like it could have been worn by a Mormon schoolmarm.

“You may finish now.” I told her, zipping my cock back into my pants. She gave a slight whimper and hesitated. “Go on,” I said. “On the couch.” With a look of relief she sat back on the couch and reached under the folds of her skirt.

Her hand went straight to her crotch and began a rapid rubbing motion. “Stop!” I barked abruptly. She froze with her hand buried in her twat and although she did not look at me, I could see the panic and shame in her eyes. I lifted her skirt and bunched it around her waist, so I could see her hand burrowing inside her pretty pink panties. Grabbing the soft cotton on either side, I pulled her panties down slowly, revealing her glistening bush and soft thighs, until the damp fabric was twisted around her ankles. I spread her knees wide, exposing her steaming pink slit and engorged clit. “You may continue.” I told her.

Sherry’s face was red with shame and she tried to avoid eye contact as she resumed stroking her pussy, a little slower now. I stared as her fingers dipped into her dripping cunt and circled her swollen clitoris. I don’t know who enjoyed her performance more, her or me, although within a few minutes, she was the one who was biting her fist to stifle a moan as her orgasm overtook her in a series of wrenching tremors.

I let her recline on the couch as she recovered from the intensity of her orgasm. As she caught her breath, I enjoyed the thought of how thoroughly I had turned this once-chaste housewife and mother into a cock sucking whore and sex slave, willing to do my bidding. I reached out and petted her abused and still sensitive pussy, causing her to jump at the touch. “You may go now.” I told her, “but be back at the same time tomorrow.” With that, I walked out of the room, leaving her to reassemble her clothes and get out.

Sure enough, the next morning, at the ‘stroke’ of 10, Sherry knocked on the door. In fact, Sherry made herself available every morning for the next week and I took advantage of the opportunity to train her in the fine arts of cock sucking and suburban whoring. I taught her to kneel in front of me and to keep her eyes open and holding my gaze when she blew me. With much uncomfortable practice (uncomfortable for her, that is) I taught her to take my cock deep in her throat and tongue my balls while massaging my pole with her throat muscles until I blasted my load directly down her gullet and into her stomach. I taught her how to heighten my orgasm by sucking and fondling my balls and asshole when I came. By the end of the week she had mastered enough skills so that she could have earned a good living working the docks of San Pedro. Eventually, I fucked her too. But that seemed to have the wrong emotional subtext and didn’t produce quite the same rush for me, although it was fun to send her home with her cunt all soupy and awash with my jism.

* * * * * *

Depravity is a drug. And I was hooked. Although I was enjoying my daily sessions with Sherry, I began to feel a need to take our relationship to another level. I had periodic twinges of remorse, mostly over the fact that all of this was taking place behind Lisa’s back, but the incredible sense of power and control I got from my new plaything was too great. I began scheming, thinking up new acts of debauchery that would assert my control over Sherry and give me the fix I needed. One morning, as I watched Harvey load Max into the car to go off to school, a glimmer of a plan began to form in my head.

A little while later, Sherry showed up for her daily session with me. I let her in and, as was now my custom, immediately made her strip naked and took away her clothes. I led her to the kitchen and made her clean the dishes, while I interrogated her about her husband and his daily schedule. The kitchen had several large windows to our back yard, which, although it was pretty private, still left open the possibility that someone could look in and see Sherry naked in her neighbor’s kitchen as if it were the most natural thing in the world.

I could see that the combination of the possibility that she might be seen and the fact that I was asking her intimate details about her family was producing a strong sexual tension in Sherry. She was nervous, frustrated and scared all at once. I moved up right behind her at the sink and pressed my fully-clothed groin into her naked ass, pinning her against the counter. I reached around and grabbed her already stiff nipples in both hands and began a vigorous twisting of those tender nubs – clockwise on the left and counter-clockwise on the right.

“So,” I hissed, with my tongue practically in her ear, “does Harvey know what you do over here every day?”

Sherry’s eyes widened. “No,” she replied hesitantly, “not exactly.”

“Well, what ‘exactly’ do you tell him?” I asked sarcastically.

“He told me that it was my problem and that I had to do whatever it took to fix it, so I just tell him that I do whatever you ask me to do and leave it at that.”

“You mean you don’t tell him that you strip naked for me?” She bit her lip and shook her head no. “You don’t tell him that you suck my cock like a whore and drink my cum?” She shook her head again. “You don’t tell him that you get so horny that you diddle your cunt while I watch the show?” I was twisting the knife now. “Like he doesn’t know, anyways. Does he get all hot and want to fuck you afterwards, or does he just jerk off imagining all the things I’m doing to you?”

That got a rise out of her. “Well he’s not fucking me, that’s for sure,” she said coldly.

I laughed at her response. “Today we’re going to give him a little present.”

After that, I took Sherry to the guest bedroom and put her through her paces. She demonstrated an enthusiasm bordering on hunger as she lubed up my shaft with her saliva and began stroking it rapidly with her left hand, making her diamond engagement ring glint in the dim light. She sucked my balls into her mouth and swirled them around like wine, then went down and tongued my puckered anus until it was moist and juicy, before rising up and plunging my slick shaft all the way into her throat.

I was in no mood for a display of her talents, however and I took over, fucking Sherry’s face with abandon. I ruthlessly plundered her mouth and throat, pummeling her soft palate with my cockhead and slapping my balls off her chin with each stroke. I pumped my cock furiously into her mouth as I felt the cum rising in my shaft. As my spunk erupted from the tip of my shaft, I ripped my cock from her gasping mouth and began to spray down her face and hair with my hot, sticky seed. After firing a shot off her forehead, I pointed my cannon at her shiny black tresses and fired out blast after blast into her glossy mane. I squeezed out the last drop into her hair, leaving her tousseled locks festooned with sticky blobs of my cum.

Afterwards, I made her get dressed and go home without her usual masturbatory release. I instructed her not to wash or even touch the mess in her hair. I told her that if my cum wasn’t still in her hair tomorrow, there would be hell to pay and that she didn’t want to find out what that meant.

* * * * * *

The next day, I was ready to begin the next phase of my plan. I watched through the window as Harvey left with Max. I took a long hot shower and tried to relax but I was too excited. Like a kid before Christmas, I was bursting with anticipation. Finally, I locked up and went across the street and rapped sharply on Sherry and Harvey ’s door. Sherry was clearly surprised to see me and the shock and fear were plain on her face. “Invite me in, Sherry.” I instructed her.

She stepped aside to let me inside but as soon as she shut the door, she blurted out, “What are you doing here?”, keeping her voice in a low stage whisper, even though we were the only ones in the house.

“I thought we’d play at your house today.” I replied mockingly.

Her hair looked awful. My cum had dried to a dull paste. It might not have been obvious exactly what it was, but the matted clumps sticking up from her hair were a sure sign that something was amiss.

“So how did Harvey like his present?” I asked, running my fingers through her gnarled coif.

“He didn’t say anything.” Sherry mumbled.

“Nice. Very nice” I replied with a laugh. “He’s a classy guy. Let’s go into the kitchen, I feel like a cup of coffee.” Sherry put the kettle on to boil and began to straighten up the kitchen, nervously flitting from side to side. “You know, Sherry, that’s not really appropriate attire for that sort of work.” I said, with a nod at her plain cotton shirt and sweatpants.

“What do you want me to – oh.” She stopped, realizing what I was asking. Bowing her head, she began to unbutton her shirt, peeling it off to expose her simple white underwire bra pushing up her modest chest. She slid her pants down too, revealing her plain cotton panties. It wasn’t going to get her hired down at the Spearmint Rhino but watching this suburban mom reluctantly strip was tremendously exciting. As she shrugged off her bra, revealing her small breasts and diamond-hard nipples, I felt my cock twitch with joy.

When she was totally undressed, Sherry resumed her chores while I sat down on the couch and waited silently. I watched Sherry walking around the house, completely naked, cleaning up the dishes and general mess. The contrast between her stark nudity and her domestic actions was extremely stimulating. I particularly enjoyed watching her plump asscheeks shimmy as she sashayed by.

I let the tension grow in the silence between us. Although I enjoyed watching Sherry squirm in anticipation of my next move, I felt a need to exploit my control over her. As she put away what looked like the remains of the lunch she had prepared for the kids, I had an idea. I crossed the room silently and grabbed her arm as she was putting away a bag of carrots.

“So you like carrots.” I stated flatly. “Me too. I love carrots.” I turned the bag over and a medium-sized carrot slid out of the hole, causing Sherry to grab it before it fell to the floor. “Right now I’d like to see you love this carrot.”

She looked at me like I was crazy, staring back and forth between me and the carrot while she tried to figure out what I meant. I raised my eyebrows as if to say, “What are you waiting for?”. A look of shame and understanding came across her face and she slowly raised the unwashed root to her mouth and let it rest on her plush lips. Slowly she snaked out her tongue and ran it in circles over the carrot’s tip before gradually sliding it into her mouth. Her embarrassment was palpable, but she did a good job attempting to appear sensual as she fellated the cold orange stalk.

When she had taken enough of the carrot into her mouth to cause her cheeks to bulge obscenely (although not down her throat, as I now knew she was capable of), I shook my head with a look of disapproval. “I said love the carrot, Sherry.” She paused in mid-suck and stared at me, until that same look of shame and understanding again washed over her face.

Withdrawing the carrot from her mouth, she slowly dragged it down her torso and through the dark patch of hair between her legs. She slid the carrot across the opening to her pussy and looked at me expectantly, as if anticipating a reprieve that did not come. Bowing her legs to provide easier access, Sherry penetrated her vaginal lips and fed the carrot steadily into her canal, producing a visible shudder throughout her body. Sherry looked uncomfortable, not just because she was fucking a vegetable in front of me and her face was beet red with embarrassment, but also because her crouching position and bent legs seemed awkward.

Rising from the couch, I took her by the shoulder and led her back to the seat. Without allowing her to remove the carrot from her cunt, I eased her down on the fabric and propped her legs on either side so that she was splayed open in front of me and I had a close up view of the now slick carrot as it slid into her gaping hole. Settling back into the seat she began to warm to her work, churning her cunt with deep, steady thrusts of the glistening vegetable. She picked up her pace, pumping faster, occasionally removing the carrot from her hole to slide it along her enflamed pussy lips and over the engorged nub of her clit. On one of these strokes I took charge, interrupting her with a command.

“That’s right. Run it all the way up there.” She pondered this command from under heavy-lidded eyes and began sawing the greasy stalk across her clit like a concert violinist.

“Now down.” She turned the carrot around and dragged it back down through her wet furrow. When she was finished she started to re-insert the carrot into her pussy, until I stopped her. “Keep going.” I said calmly, “Further down.” Withdrawing the carrot from her snatch, she obediently continued the southward journey of the erstwhile snack.

Her eyes were wide open now as she tentatively slid the flat of the carrot across her wrinkled ass pucker. Back and forth, like a nervous teenager playing a Bach sonata at her first recital. She would not make eye contact with me, but I could see the hot flush of shame on her cheeks. “Sherry,” I said quietly, commanding her attention. “Go on.” I gave her my best “Don Corleone” nod and the color drained from her face. She knew what had to be done.

Tilting the carrot outward, she began to search for her puckered opening with the tip. Probing blindly, she circled her anus with the slick stalk, spreading her pussy cream around the rim. Finally the tip dropped into the tiny aperture with what seemed to be an audible pop. She hesitated for a moment, then pushed forward with the carrot making a slight dent in the surface of her asshole, but nothing more. She shifted her grip on the carrot and tried again. This time about a half inch of carrot disappeared inside her ass as Sherry emitted a sharp moan.

“I can’t do it,” she said in a small voice. “It’s just too tight.”

I took in the sight of her white knuckles attempting to strangle the offending carrot and her taughtly clenched abdomen and asscheeks with which she desperately attempted to expel the intruder in her rectum. I could understand why she couldn’t do it. I gave her a wry, disappointed smile and leaned in to clap my hands on her shoulders and kiss her roughly on the mouth.

“That was a good try,” I hissed before I captured her tongue in my mouth. I kissed her brutally and swabbed her throat with my tongue. She whimpered with relief and I felt her go limp as she succumbed to my oral assault.

“But not good enough,” I thought to myself as I drove forward with my hips and used my clothed groin to push the carrot into her sphincter. She tensed and drew a deep, sucking breath as I pressed forward and sank the first inch into her rectum. I paused for a moment to let her initial paroxysm pass and then, as if I were tapping a nail, I drove the carrot bit-by-bit deeper into her tightly clenched bowels.

When I had roughly 5 inches of the rigid root stuck in her ass, I released her mouth and sat back to enjoy my handiwork. She looked pale and drained, but perhaps not as uncomfortable as you might expect of someone with an undigested vegetable in her colon. “See,” I said, encouragingly, “I knew you could do it. Now stand up.”

Sherry staggered to her feet and I switched places with her, sitting myself on the chair while she stood in front of me. I reached out and grabbed the hilt of the carrot, which protruded from her ass, and pulled her roughly towards me. She gave a start and lurched forward, enabling me to plant my mouth directly over her clit and sopping pussy. I sucked hard, drawing her engorged lips and throbbing nubbin into my mouth. Sherry gasped and her knees buckled but I was able to stop her fall as my firm grip on the carrot effectively made her impale herself even more.

I flogged her clit with my tongue several times, drawing violent shudders from her. She was juicing copiously and I could literally taste her excitement. The feeling was electric. I felt totally alive and preternaturally aware of all my senses. My lust was overwhelming and I jumped up to tear off my clothes before regaining control and stopping myself with a jerk. This wasn’t in the script. I had planned out much more, and giving in to my urges now would certainly put a wrench in the plans.

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.

* * * * * *

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 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!”

* * * * * * *

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.

Slowly, I peeled myself off of Sherry’s back and began to extricate my shaft gradually from her anus. I was still hard but deflating rapidly as I withdrew from her ass and was greeted by the sight of her cavernous hole gaping at me like a secret passage to her soul. A drop of my slop drooled wetly from her yawning maw and fell on the floor, only to be joined rapidly by a succession of even larger blobs pushed out by her spasming rectum. This was the most deliciously obscene scene I could possibly imagine and I had a visceral sense of euphoria wash over me as I watched her anus gulping for air like a fish on the deck.

Apparently Harvey had a similar reaction as he let out a strangled moan and began to spurt his cock sauce onto the carpet without a single stroke on his shaft. I watched Sherry take in the scene and was fascinated by the look on her face as she saw her husband climax at the sight of her anal despoliation.

I grabbed a pillow from the couch and used it to wipe the santorum from my cock, leaving a greasy brown smear on the cream-colored fabric, and stumbled off to the kitchen. Sherry and Harvey lay sprawled behind; Sherry face down across the arm of the couch and Harvey slumped heavily in the chair. Neither one looked at me or at each other. I was sweating profusely from my exertions and I gulped water directly from the faucet to cool down.

“I don’t know about you guys,” I shouted from the kitchen, “but I’m hungry. Hey Harvey , do you like carrots?”

* * * * * *

Author’s note:

This story is part of the series "Reversal of Fortune." If you liked it, please check out the rest as well. However you felt, I appreciate you letting me know by sending feedback using the form below.

More Truly Awful Tales from An Awful Cad can be found at http://www.asstr-mirror.org/files/Authors/An_Awful_Cad/www/index.htm

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