The Inheritance Pt. 03

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Cuckold falls deeper into shame, tries to redeem himself
8k words
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Part 2 of the 2 part series

Updated 06/11/2023
Created 09/29/2022
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Hakim didn't return home until well past noon. Per his instructions, I had been standing guard on the porch for hours, slogging through a cycle of nodding out, jerking awake, rubbing my eyes and dozing off again. The adrenaline rush from the previous evening's near-death experience had long since evaporated, leaving behind a splitting headache and guts that felt like they'd been washed out with bleach.

Isaac's SUV rolled up behind Hakim's car, followed by two identical black Mercedes sedans. Hakim, Isaac and his two bodyguards exited their respective vehicles, while whoever sat behind the tinted glass of the other two cars stayed put. The four men approached me, all frowns, while I shifted from foot to foot.

Isaac stared a hole through me. "You need to tell me exactly what happened."

I drew a breath. "Um, well, sir, I was scrubbing the kitchen floor and then there was a bunch of gunshots."

"You see anything?"

"I ... uh, sir, I was on my hands and knees, and when the shooting started, I closed my eyes. So, I really wasn't in a position to see anything, sir."

"I mean earlier last night," Isaac said. "Think, pussy boy. Did you see anyone suspicious hanging around? Or has anything happened recently that seemed unusual?"

"N-no, sir, nothing, sir."

I was fearful that Isaac or my master might somehow sense that I wasn't being forthright about my earlier contacts with the DEA agents, but the questions stopped and my heartbeat slowed.

Isaac peered through the glassless windows at the bullet holes that covered the inside walls. "We need to get you somewhere safe," he told Hakim. "I'll have some of the fellas come by and board this place up; you can come stay with me in Kenilworth. Nobody can touch you there."

"My man. Thanks."

"No problem. Your lady and kids are welcome, too, brother. There's plenty of room, and you know they'll be safe at my crib."

"No, man, I appreciate it, but I'm trying to keep them away from the life, and if they're with us at your place--"

"I understand. As long as they're okay."

Hakim nodded. "I got 'em put up in a hotel in Wisconsin. I sent Frank, Ron and JJ to guard 'em, so they'll be fine."

"All right, then, I'll have Buttercup get a couple rooms ready for you and the pussy boy."

My master shook his head. "Nah, one room's fine. The pussy boy can stay with me."

That was the last thing I wanted to hear but of course I said nothing.

Hakim snapped his fingers. "Okay, Timmy, we got to go, so get your ass moving. Pack up my clothes and toothbrush and shit, and a couple changes of clothes for yourself too."

"Yes, sir."

"And don't forget your wig and nightgowns, and your makeup, too, so you can be nice and pretty for me, Twinkie."

I choked out another "y-yes, sir," as Isaac looked on smirking.

"Twinkie, huh?" Isaac chuckled. "Figured it wouldn't be long -- just don't ruin him like you did the other ones." Isaac sneered at me. "I feel for you, Twinkie; back in the joint, this motherfucker was known for sending sissies to the infirmary."

"Hey, if they do what they're told they don't get hurt." Hakim patted me on the head. "We don't need to worry about this one; he's a good little bitch. You my good little bitch, Twinkie?"

"Yes, sir."

"Damn skippy. Now, go pack, bitch, and let's get going."

I loaded up the back of Hakim's Mercedes with our clothes, toiletries and other items and started to slide into the car -- but my master stopped me with a scowl.

"What the fuck you think you're doing?"

"Um, I ... I was just getting into the car, sir."

"Well, sit your punk ass in the backseat, bitch, you don't ride up front with me. We ain't buddies, motherfucker."

"S-sorry, sir." I squeezed in the back with the bags.

Hakim followed Isaac's SUV for about a half-hour until we stopped in front of an ominous wrought-iron gate. A man in a dark suit emerged from a guard shack and leaned toward Isaac's window. After a brief conversation, the guard flashed a hand signal, the gate slid open and the procession of vehicles filed onto the property. At the end of a winding tree-lined drive was the large house that served as Isaac's headquarters.

Weighed down by the first load of clothes bags, I followed Isaac and my master inside and gasped out loud when I glimpsed the pitiable creature who greeted us at the entranceway. Standing at about 5'6 and weighing no more than 100 lbs., this thing in a maid's uniform had obviously undergone major facial surgery, resulting in features that resembled a sad, puffed-up, feminized clown, including a brown, curly Shirley Temple hairstyle and a pair of balloons where lips used to be.

"Buttercup, you remember Hakim from Block B?" Isaac said as he handed his coat to the emaciated sissy.

"Yes, it's so nice to see you again, sir, welcome to our home, sir."

Hakim grinned. "Buttercup, you look so pretty. What did your daddy do to you?"

"Just a little tweak here and there, courtesy of Doctor G," Isaac said, rubbing the sissy up and down, clearly proud of his ghoulish creation. "A little plastic surgery might do your pussy boy some good, too. My man's got an operating room in his garage; he'll hook you right up with whatever you want -- shit regular doctors won't do."

Hakim shrugged. "Maybe later on. Right now, I got other problems."

"Yeah, you ain't kidding, brother," Isaac said. "Let's go to the War Room and figure this shit out." He turned to his sissy. "Buttercup, take Twinkie to his daddy's bedroom and help him get unpacked, and then he can help you get lunch started."

Buttercup curtsied. "Yes, Master."

"Make yourself pretty, too, Twinkie," Hakim said. "In fact, while we're here, you might as well just stay like that."

"Yes, sir."

"Two sissies are better than one," Isaac chuckled as he led his colleague toward his den, the "War Room."

After standing in the foyer alone with Buttercup for a few silent, awkward seconds, I tried to drum up conversation.

"Um, so you knew Hakim back in prison?"

"My master doesn't like me to talk," Buttercup replied in a squeaky, wavering voice.

I gazed into this pathetic, frightened, brainwashed creature's dead eyes. What I saw turned my blood to slush.

What I saw was my future.

"The Inheritance," Chapter 21

by c.w. cobblestone

"Killa Dilla" hit like "Thriller."

The Stomp Boyz had put a heavy cut on the two kilos they'd purchased from the Peruvian cartel, but the cocaine still blew up like a double-platinum Michael Jackson album, selling out in a matter of hours.

After the last packet had been moved, Hakim, Isaac, two of their top lieutenants and their floozies toasted the raging success in the War Room. Buttercup and I were ordered to pour glasses of Dom Perignon and then stand at attention cradling ice buckets containing the champagne bottles, ready to provide refills at the snap of a finger.

"Out of our initial $50,000 investment, we turned a $400,000 profit," Isaac said, clinking glasses with his business partner. "That's some primo-ass coke; we cut the shit out of it and it still blew up like a motherfucker."

"Everyone's saying it's the best shit to hit the street in years," Hakim agreed. "The question now is, when do we get more?"

"That's up to the cartel." Isaac sighed. "They said they'd be in touch after we offed the first two keys."

Hakim frowned. "So, what? We just sit around and wait?"

"That's all we can do right now, young brother," Isaac said.

"Well, fuck, that shit's frustrating."

"I know -- frustrating as hell." Isaac chuckled. "But you know how to deal with frustration, don't you? That's what sissies are for." He crooked his finger at his slave. "Buttercup, come here, sweetheart."

The sissy put down the ice bucket and stepped toward his master, while Isaac reached near his desk and produced a black stick.

"Lift up that skirt, Buttercup."

The feminized freak complied. Isaac pressed the device's tip against Buttercup's groin. When I heard a zap followed by a suppressed squeal, I realized my master's business partner was wielding a cattle prod.

"It's great for getting out frustrations," Isaac said before he again pressed the prod onto the front of his sissy's panties and held it there for several seconds. I felt sorry for the teary-eyed Buttercup as he forced himself to stand still while Isaac kept torching his genitals with the zapper.

One of the molls, a coked-up blonde with fake boobs named Dee-Dee, snickered. "Look at the sissy trying not to move. That shit's hilarious. Hit the faggot again."

Isaac granted her request, again pushing the cattle prod against the poor sissy's crotch. Buttercup's eyes betrayed his pain, but he didn't budge.

"Here, brother, try it on yours. Get them frustrations out, youngblood." When Isaac handed the device to Hakim, I stopped worrying about Buttercup and started feeling sorry for myself instead.

"Come here, Twinkie." Hakim used the prod to point to a spot directly in front of him. "Bend your sissy ass over, drop them draws and spread them cheeks."

"Oh, no, please, sir, don't, please--"

Hakim's hand slashed forward and cracked me across the face.

Isaac shook his head. "Damn, brother, you need to teach your pussy boy some manners."

Hakim's nostrils flared. "Twinkie, you better get your sissy ass over here. Don't you be embarrassing me, now, you hear?"

"Y-yes, sir."

With tears flowing, I inched my way toward my master.

"Now, bend over, pull down them panties and spread those sissy ass cheeks like I told you," Hakim said.

A split-second after I was in position, Hakim worked the cattle prod into my butthole and pressed the button.

"Aaaaaaaaaaaaaaaaaaaaaggggggggggggggggggggggggggggggggggghhhh, oh, please sir, aaaaaaaaaaaaaaaaaaaaaaaaaaahhhhhhhhhhhh."

I collapsed and rolled on the floor in agony while everyone but Buttercup sipped champagne and laughed at my misery.

"That's a weak sissy you got there," Isaac teased. "The bitch needs a lot of training. A good sissy don't move. Let me show you how it's done. Buttercup! Get over here again, bitch."

When Buttercup again set down the champagne bucket and complied, Isaac sneered. "Now, bend over, pull down your panties and spread your butt-cheeks, my little Buttercup. Let's show Hakim how a well-trained sissy does it. Okay? Can you do that for your daddy?"

"Y-yes, Master."

Buttercup did as he was ordered, and Isaac shoved the prod way deeper up his ass than my master had with me. When Isaac pressed the button, I heard a faint squeak from Buttercup's trembling throat, while the poor sissy's tears poured out, forming a dark spot on the carpet. Isaac continued holding the button while conversing with Hakim.

"I think you done got soft in your old age," he jibed, probing Buttercup's asshole with the terrible electrode, up, down and side to side. "You're letting that sissy of yours slide too much."

"Man, that's no fair," Hakim joked back. "You've had your sissy since way back on Block B, and I just came home."

Isaac finally pulled the cattle prod from Buttercup's ass and handed it to him.

"Clean it off and give it back to Hakim," he ordered, sending the trembling, watery-eyed Buttercup scrambling to obey. When the sissy returned with the sterilized prod, Hakim held out his hand and the pansy passed it to him.

"We're gonna try this one more time, Twinkie," my master said. "You gonna be a strong sissy for me?"

"Y-yes, sir."

One of the other floozies in the room, a black woman named Jan who was clearly stoned, pointed at me. "Look, the little faggot's leg keeps shaking. Ha-ha, I think he's scared."

"Give the little bitch something to be scared about, Hakim" piped in the silicone-enhanced Dee-Dee.

Hakim smiled at me. "I know it must hurt having a cattle prod shoved up your ass, Twinkie. But if Buttercup can take it, you can, too. Right?"

"Um ... uh, yes, sir."

"I won't be having my friends thinking I don't know how to run a sissy. You hear?"

"Y-yes, sir."

"Good. Now, let's try this again. Drop them panties and spread them cheeks. You gonna be a brave sissy for your daddy and not move?"

"I ... I ... I'll try, sir."

"You'll what?"

"I ... um ... yes, sir-- ahhhhhhhhhhhhhhhhhhhhhhhhgggghgggg!!!"

The words were barely out of my mouth when the cattle prod hit home, sending an unfathomably painful shockwave throughout my body. My anal canal was burnt toast.

"Oh, please take it out, sir, please, it burns so bad," I sobbed.

"Quiet, bitch, and stay still." He shoved it in deeper, to the chuckles of everyone present. I bit my lip and prayed.

The inhuman trauma inverted the universe and sent me spiraling into a dimension of blackness, exploding colors, flying hieroglyphics, morphing shapes, trumpets and gongs, roller-coasters and merry-go-rounds. But I didn't move. Somehow, despite enduring the worst wall of pain imaginable, I tapped into my inner Buttercup and managed to obey my master and stay stock-still.

Hakim finally yanked the prod from my ass and handed it to me. "You done good, Twinkie. I'm so proud of you. My little Twinkie."

"T-thank you, sir."

Isaac chortled. "Damn, brother, you might make a good sissy out of this one yet -- if you don't end up killing the bitch first."

My master, his gang friends and their sluts all thought that was hilarious, although as I retook my position holding the ice bucket, with eyes that wouldn't stop crying, I failed to see the humor in it.

"The Inheritance," Chapter 22

by c.w. cobblestone

Buttercup and I wore identical maid's outfits as we stood posts on opposite ends of Isaac's sprawling dining room table like pair of feminized book ends, one blonde, one brunette, one skinny, one fat.

"A toast." Isaac held up his glass. "To our guest, the renowned Alfredo Garcia, and his esteemed colleagues from Peru. May this be the beginning of a long and fruitful relationship."

"Hear, hear," Garcia hefted his glass and sipped. Everyone followed suit.

"We appreciate your faith in us, Mr. Garcia," Hakim said, and I was jarred to see him deferring to the cartel king, since my master usually was arrogant beyond belief with everybody else, especially me.

"I like your style." Garcia chuckled. "You Stomp Boyz. You got rid of those two keys in half the time those idiots in New York did, and in a smaller market, too. And zero issues; in Philly, three of their runners got arrested, one of them talked to the cops and now we've got major problems there. Same thing in Detroit. And don't even get me started about those cabrones in LA."

"Well, there won't be any issues here, Mr. Garcia," Isaac said. "We run a tight ship in Chicago."

"Clearly." Garcia nodded. "Which is why we're moving forward Tuesday with the additional 20 keys."

"Well, we appreciate the opportunity," Isaac said.

"Indeed." Garcia's eyes hardened. "Just don't fuck me, comprender?"

"Of course not," Isaac said.

The conversation drifted to the details of Tuesday's pending drug sale, which was to go down in an abandoned meatpacking warehouse on the South Side. The price for the 20 keys was $450,000; the plan was for Isaac and Hakim to use the $400,000 profit they'd made on the initial Killa Dilla sales, and then for each of them to kick in an additional $25,000. Isaac agreed to loan Hakim his half because the 15th was still a few weeks away, and Hakim wasn't able to immediately access the $30,000 monthly stipend from my mom's estate.

As always, it infuriated me to listen to Hakim discuss my mother's inheritance money like it was his -- even though essentially it was, if not technically on paper -- and, as always, I stood there like a wimpy loser and didn't say or do a goddamn thing about my wife's lover usurping my birthright.

Dinner lasted a little over an hour and then the guests from Peru were escorted out, at which point Buttercup and I started cleaning up and doing the dishes. I'd spent about a week at Isaac's place, and Buttercup and I were starting to work in perfect synch, anticipating beforehand what the other would do. That worried me. I didn't want to get comfortable being a frightened, mindless sissy maid like Buttercup -- but more and more, my master had been talking about just that, telling Isaac he'd like to take me to his plastic surgeon friend to have me "fixed up." So, it appeared being a brainwashed, permanently feminized freak was to be my fate, like it or not.

When Isaac and Hakim returned from seeing their guests out, they relaxed with cigars in the living room while Buttercup and I stood at attention near our respective masters.

"It's gonna take off, brother," Hakim said as I lit his stogie and returned to my post. "I figure another two weeks, tops, and I'll be able to pay you back my $25,000 and put a down payment on that house I wanted."

Isaac nodded. "It's all working out. How's that woman of yours doing? And your kids?"

I perked up, since news about Amber and the kids had been scarce.

"Talked to her a couple days ago," Hakim said. "They're fine. Anyway, I'm thinking once I get that house on the lake, we can split things up, so the operation ain't all in one place. I think it's better that way strategically, what do you think?"

I was furious that Hakim seemed more interested in discussing his drug activity than the woman he supposedly cared for and their children. Isaac seemed more concerned about their welfare than Hakim, and I realized that Amber and the twins weren't holed up in a Wisconsin hotel because Hakim wanted to protect them from the drug life; he just needed them out of his hair while he set up his cocaine empire. I despised the evil, selfish sonofabitch with all my soul, and wondered if Amber would ever see the light and leave his punk ass.

My jaw hurt from clenching, but I kept quiet and stood my post while Hakim and Isaac continued chitchatting until the doorbell rang. Buttercup answered it, returning with two trashy, scantily-clad bleach-blondes.

Isaac smiled. "Ahh, Connie, Gina, welcome, ladies," he said as each woman sidled up to the two gang leaders and sat on their respective laps.

"Now, this is celebrating in style," Hakim said. He snapped his fingers. "Twinkie! Get me a beer and see what Gina wants."

"I'll take a wine," the woman said before turning to Hakim and giggling. "Damn, I've never seen a sissy that fat before."

"You're used to Buttercup." Hakim sniffed. "Isaac starves that poor motherfucker."

Isaac laughed. "Oh, come on, now, it's not that bad. I make sure the bitch gets plenty of vitamin supplements."

"Yeah, I'm sure it's quite tasty." Hakim smirked.

Gina pointed at me. "Well, you need to put that one on a diet, cause he's fat as hell. Looks like a damn cow."

"Hey, I like a mushy butt on a sissy, what can I say?" Hakim then turned to me and scowled. "Why are you still standing there, bitch? Drinks."

"Y-yes, sir." I scrambled to obey.

When I returned with the beverages, both couples were making out, so I stood there holding the serving tray and gritting my teeth as I watched my master cheat on Amber with this slut. I'd long since pegged Hakim as an amoral asshole, so I wasn't the least bit surprised. But watching him casually betray my wife like that spiked my blood pressure and made me feel like somehow, I also was cheating on her.

They eventually took a break, and the group discussed the quality of Killa Dilla. After the beverages were consumed and the ladies snorted a few lines of the product, the two men decided it was time to turn in. They escorted the ladies to their respective bedrooms with Buttercup and me in tow.

Once we were inside our room, I hurried to "make myself pretty" while my master and his ho undressed.

Gina wiggled out of her panties and pulled them over my head.

"Hee-hee-hee, these sissies crack me up." She helped Hakim out of his briefs and arranged them on my head over her panties. "Can you see me, sissy?"