Cherry Ch. 09: My Family Conquered

This is Chapter 9 of the Cherry saga. This chapter has (believe it or not) darker themes than the others, including incest, impregnation, and slavery. There are likely to be trauma cues for sensitive readers. Reader discretion is advised.

And as always, I welcome community feedback in the comments or my DMs.

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Chapter 9: Sir Conquers my Family

Sir sat back in his high-backed chair and sipped his whiskey. Sir was a fan of Canadian whiskey, and he picked several expensive-looking bottles when he went to British Columbia to 'collect' the newest additions to his harem.

I stood at Sir's left hand holding a flat tray--at the moment, I was nothing more than a human nightstand. At Sir's orders, I had been growing my hair out in the months I've lived with him. My strawberry-blonde locks now framed my petite shoulders. To add to my humiliation, my hair was kept back by a French maid's bonnet. Traveling down my body, a sheer white top did little to cover my budding a-cup breasts. While I fully expected Sir to make me get implants soon, the hormones were already filling out my chest. A French maid's skirt framed my generous ass and hips. With the ruffles pushing the skirt out, my little dicklet hung out from underneath.

Sir had instructed me not to wear panties today. As my mother and sisters knelt naked in front of Sir and me, Sir wanted them to see what had become of their brother and son.

My brother Kyle, now "Kylie," stood at Sir's right hand. She was dressed in an identical French maid kink outfit, but with shorter hair. Kylie held one of the expensive Canadian whiskey bottles that Sir had picked up on his way to collect his new specimens. I seethed at how Sir probably saw my family as a series of commodities in the same way he saw the bottle in Kylie's hand. I was impotent at the moment, both literally and in terms of my agency, to do anything about it.

Three women kneeled in front of him, naked from head to toe. Sir had ordered them into a state of unconscious sub-space while he issued commands and orders that they would always follow, knowingly or otherwise. Despite my hatred for the man, I couldn't help but admire the nuance and subtlety that he wove into his programming. He had obviously thought this out. He covered every exemption to his orders against escaping or contacting the outside world. He even covered exceptions to exceptions of rules that I would never have thought of. It was little wonder that any of my own plans of escape met with instant failure. I was owned by a master who was much more intelligent, and who had much more foresight than myself.

Sir had previously used the same technique to "install" routines and programs into me. For example, I have no memory of the commands that my Master issued that changed my perspective of reality when he said, "Cock worship mode," or changed me into a thirsty slut when he said, "Slut mode." He had likely planted commands and routines in me that I was not yet aware of. And there I sat, holding a tray for his glass of whiskey and a small bucket of ice as he casually rattled off conditions and programs for my mother and sisters.

Sir never planned to hide his intentions. While he initially planned on giving me away to a client or investor, Sir had taken such a liking to me that he intended to keep me around to look after his house. Before he went out to collect the specimens in front of him, he was upfront about his long-term plans. Sir would program the trio to be perfect little trophy wives, then send them off for extreme plastic surgery and body modification ("bimbofication," as Sir would say with a laugh). Sir would then give them away as tokens of appreciation to generous investors.

After Sir spent about an hour giving complex commands, he took a break. "The programming depends on the subject's long-term memory. So I can't give them too many commands at once," Sir mused to Kylie and me, "that'll be enough programming for one day. Let's have some fun with our new toys in the meantime."

Sir moved his posh, crystal glass to his left hand and raised his right hand above his shoulder with his palm facing himself. Touching his thumb against his middle finger, Sir looked at my mother. He then at my sisters. My sisters were named Olivia and Lindsey, though I expected Sir to change those eventually. After examining the trio contemplatively, Sir turned toward me on this left, looking me up and down, then to Kyle on his right.

SNAP. The trio in front of Sir sprung into awareness at the snap of Sir's fingers. My mother and sisters shook their heads and opened and closed their eyes in bewilderment. After a moment, the three looked around, panicked. They squinted at Kylie, before widening their eyes; Sir had not yet subjected her to any body modifications, so she was recognizable as Kyle underneath the humiliating outfit and expertly-applied makeup. Olivia and Lindsey were dumbstruck; my mother tried to open her mouth to cry out, but her conditioning prevented her from speaking without permission. The women's realization that they were unable to speak or move from their kneeling positions further fueled their panic.

After lip injections, months of hormone replacement therapy, and my experience with cosmetics, they probably didn't recognize me as their son and brother, Caleb. Not that I would respond to that name anymore, anyway. Sir's programming had thoroughly erased my brain's connection to that name as an identifier.

As the women's panic increased at their predicament, Sir spoke up. "Ladies! Welcome to your new home for the next few weeks." Sir leaned forward in his chair, holding his glass against his knee. "As far as you're concerned, my name is 'Sir.' Here on my right," Sir gestured broadly, "is Kylie. You used to know her as Kyle. But you will never refer to her as that name again. I'm borrowing Kylie from her handler during your stay. She's going to help me keep an eye on you, and help you in your transition. Here on my left," Sir gestured toward me, "is Cherry. You used to know her as Caleb. But she keeps me company now. She's going to teach you about being a perfect trophy wife. Just like she is for me." I chirped as Sir reached over and pinched my ass cheek.

Terror filled the trio's eyes as they recognized me. I could see the realization that Sir had absolute power over our actions and appearance. Olivia and Lindsey looked down with dreadful anxiety. If Sir could turn their rebellious brothers into the spectacle before them, what could he do to them?

"Olivia, Lindsey, crawl over to me." I could see the confusion in my sisters' eyes as their hands and legs involuntarily crept toward Sir. I remember well the first time that Sir had given me a command, and that first, terrifying experience of my limbs moving without my consent. When both girls were in front of Sir, one in front of each knee, Sir looked around the room at the five of us.

"I want each of you to enjoy the next few weeks. Unless one of your new handlers brings you to a mutual party, it will probably be the last time any of you see each other. But first," Sir set his glass down on the tray I was carrying, "I have a game for the two of you." Sir reached forward and put one hand on the sides of each of my sister's faces. "I want to have a child. And I must say, your family has great genes. One of you is going to carry it for me, but I haven't decided which one. So we're going to play a game. You're going to take turns sucking my cock. You'll each get fifteen seconds at a time. Whichever girl makes me cum will be the lucky winner. After your training, I'll fuck the winner, and she'll get to stay here for the next nine months."

My sisters looked up at Sir with a mixture of fear and rage; tears filled their eyes. My mother furiously shook her head and moved her mouth, but was unable to do anything more. Kylie and I exchanged wide-eyed glances. Sir was a monster. An evil man. A kidnapper. A murderer. A rapist. And now, he was going to force one of my sisters, fresh out of college, to carry his child.

Rage built in my gut. I wanted to do something. I wanted to lift the glass and tray in my hands over Sir's head and bash his brains in. But my programming wouldn't allow me to move a muscle. And I knew that if my thoughts strayed too close to "escape," that my fallback programming would kick in and I would keel over in pain. I knew that I would need to bide my time, but I desperately wanted to kill that man.

Sir unbuckled his belt and lowered his zipper. "No tears now, ladies." Olivia and Lindsey immediately stopped crying. Sir looked over at my mother, then down to my sisters. "Let's be grateful now, girls. I want you all to give me a smile." Each of the three women's lips turned up at the edges in a goofy, painted expression of glee. But none of their smiles reached their eyes.

Sir's erection spilled out of his pants, growing in size at his expression of power. "Olivia, I want you to go first. But start slowly. Give it some kisses and tell it how grateful you are for the privilege of sucking it."

Olivia leaned forward immediately--probably before she knew what she was doing--and kissed Sir's cock up and down the shaft. "Thank you," she slowly cooed through pouty lips, "thank you for letting me suck you."

"That's a good girl," Sir purred. After fifteen seconds, he pulled Olivia's face away and pulled Lindsey in with his other hand, "your turn, Love."

"Thank you," Lindsey mimicked through pouty lips, "thank you for letting me suck you." Beneath her painted, pouty smile, I could see rage and disgust burning in her eyes.

Fifteen seconds later, Sir pulled Olivia in and shoved his cock between her lips. "Mmmmm," Olivia feigned in delight as her head bobbed up and down on Sir's cock.

Sir's head rolled back in his seat. "Good girl," he mouthed.

This went on for several more minutes. As Sir picked up the pace moving each of their heads, one after the other, up and down on his cock, I could sense the fear growing in both of the girls. I knew that they loved each other and that neither would want the other to have to experience nine months of slavery and unwanted pregnancy. And, understandably, neither would want that for themselves either.

Sir continued picking up the pace until he was face fucking each girl. During one of Olivia's turns, Sir let go of Lindsey's head to place both hands on the back of Olivia's neck. Sir held her down as he sharply exhaled. "Fuuuuck," he breathed. He pulled the poor girl up to look at him. His cum dribbled down her chin as she looked up at him in horror.

Sir stroked the hair from Olivia's face. "We have a winner," he said through an evil grin. "Now don't waste any of that. Swallow what's in your mouth and clean up the rest. And each of you will respond with, 'Yes, Sir,' when I tell you to do something."

Olivia swallowed. "Yes, Sir," Olivia's voice was gravelly after the experience. Her head went down to Sir's pants and chair, and lapped up the excess with her tongue and lips. After she was satisfied that she got every drop she looked back up at Sir, swallowed, then opened her mouth to show that she got it all.

"Good girls!" Sir admonished Olivia and Lindsey. "Now crawl back to where you were and kneel next to your mother."

"Yes, Sir," they each chanted in a sing-song voice as they crawled back to their original positions. Sir looked over at me with a satisfied grin on his face. Looking down, he saw that my little dicklet was trying to get hard.

Sir guffawed, "Did seeing his sisters suck Sir's cock turn Cherry on? I see that the hormones are kicking in nicely. That little softy is probably what, two and a half inches at best?"

I looked down in shame. Kylie's little erection revealed that she was also turned on, but she hadn't been on hormones as long as I had. She clearly wasn't as "blessed" as Sir, and the hormones had shrunk what she had. But she was sporting a little four-inch erection. It hadn't escaped Sir's notice.

Kylie chirped as Sir pinched her ass cheek. "So, seeing your sisters serve Daddy's cock turns Kylie on, too! Does Kylie also want a blowjob from a submissive little bitch?"

Unfortunately, the programming wouldn't allow either of us to lie to our master if asked a direct question. And I knew that my brother (now sister?) had a porn habit, so I feared the answer before she gave it.

"Yes, Sir," Kylie said meekly.

Sir leaned back and picked up his empty glass from the tray in my hands. He reached into the ice bucket and dropped two cubes into the glass. "Top me off, Kylie."

Kylie complied, pouring the expensive liquid into the glass from the exquisite bottle in her hands.

Sir looked at Kylie, then to the trio kneeling in front of him, then back to me. His devious grin grew into a sadistic smile. "You've been such a good girl to hold that bottle for me, Kylie. And I'm feeling generous today. So I'm going to give that to you. A submissive bitch to suck your little cock."

Sir snapped his fingers and pointed at me. "Cherry, set the tray down and get on your knees in front of Kylie."

Oh no. Please. I didn't want to suck off my brother. I hesitated, trembling.

"NOW, Cherry." The dread filled my gut at the admonishment. I immediately set the tray and bucket on the ground and scurried over to Kylie. I dropped to my knees in front of her.

"Now," Sir continued, "give Kylie's little dicklet a kiss."

Before I could wrap my head around what was happening, I leaned forward and planted a small kiss on the side of Kylie's shaft.

"You can do better than that," Sir said with a wicked undertone.

I leaned forward again, pushing my inflated lips out into a pouty expression. I kissed the same place, but this time I grabbed the shaft to hold it against my lips. I held it there for a long moment, delivering a big, wet kiss.

"Good girl," Sir continued, "now lick the underside from the base to the tip. Don't let your tongue be stiff; use a big soft tongue just like you use on Daddy."

I crouched slightly to get my head underneath the base of the shaft and moved my lips to the point of contact between the shaft and the balls. My nose came in contact with Kylie's smooth, shaven skin as my tongue came out in a big, soft arc underneath his shaft.

"Good girl. Now keep going. Kylie's been such a good girl to turn over his mom and sisters to his new daddy," Sir cast an evil grin toward the trio, "so keep licking Kylie's little cock."

I moved my big, soft tongue in an arc from the base of Kylie's shaft to the tip, then back again. Sir reached out and took the bottle from Kylie's hand. "We don't want you dropping that on Cherry's head, now," Sir laughed.

"Now Cherry, open those big, dick-sucking lips of yours and put Kylie's cock in your mouth. All of it. And hold it there until I tell you that you can lean back."

I opened my mouth, and obediently took all of Kylie's cock into my mouth and throat. Luckily, Kylie was naturally small, and the hormones continued to shrink her member, so it barely touched the back of my throat. When I would deep-throat Sir, I typically couldn't breathe when it was all the way in. By contrast, I could still get air through my nose when taking my brother.

"Now bob your head back and forth," Sir ordered, "and don't forget to use your tongue like Daddy taught you."

I could feel Kylie shuddering as I desecrated myself on her cock. I wondered what she felt. I wondered if she felt shame that her brother (or now, "sister") was being forced to suck her cock. I wondered what the post-nut shame would feel like for her.

"Kylie, don't just stand there," Sir encouraged, "put your hand on Cherry's head. When a bitch is sucking you like that, you need to take control and set the speed and depth."

I felt Kylie's trembling hand moved toward the back of my head and grip some of my hair. Her hand was much smaller than Sir's. And much less sure of itself. But she pushed my head into her cock at a slightly quicker speed than I'd been going. And I could feel her hips moving back and forth at the same rhythm. At Sir's command, she was taking control and fucking my face.

Sir looked like he was having the time of his life. He looked over at my mom and sisters, who watched on in helpless revulsion.

"Don't just sit there, Ladies," Sir gestured toward the trio, "these bitches are giving you a show. This fucking turns you on." At the command, I could hear them breathing more heavily.

"Now let's not waste the moment," Sir continued looking at my mom and sisters, "since you're enjoying this show so much, each of you put your left hand on your clit and start rubbing."

The humiliation of this spectacle was incomprehensible. Sir was leaning back in a high-backed chair with his legs crossed, having just face fucked both of my sisters. Now they, alongside my mother, were being forced to masturbate while watching me on my knees sucking my brother.

At this point, the tone in Sir's orders bordered on jeers. He was the ringleader, and we were all clowns in his fucked up circus. "I can tell that the three of you are fucking enjoying this," Sir shook his finger at my mom and sisters, "now cum."

Out of the corner of my eye, I saw each of them curl over into a fetal position and convulse. My eyes widened in shock and rage at the display.

"Cherry," Sir continued, "you're getting so fucking horny sucking this other tgirl."

I could feel my limp little erection stirring even stronger at the command.

"It's so fucking hot, you just can't help but cum."

At the command, my little dicklet spurted two little globs of semen. I could barely see it around Kylie's cock beneath my eyes, but I wouldn't have guessed my load to be more than a couple of teaspoons.

"Now Kylie," Sir continued in his diabolical charade, "you've brought your whole fucking family to finish with this display. You should feel so proud of yourself. You're such a good little bitch."

Kylie gleamed. And I was furious because I knew that Kylie was having an authentic experience now. Not on her own accord, but at Sir's orders. As he commanded, she felt pride and gratitude over this pathetic, incestuous charade.

"You're so fucking happy and horny, Kylie" Sir was wrapping up this little show for himself, "now cum down Cherry's throat. Don't let the bitch spill a drop; hold her face against your cock until she swallows every drop."

Kylie exploded down my throat and held me against her groin by my hair. Following the implied command, and wanting this scene to end, I slurped up as much of the liquid as I could as fast as I could. After Kylie was satisfied that I got it all, she released me. I fell back onto my ass, then laid on the ground, curled up in shame.

We sat in silence for a moment. I suspected that Sir wanted the five of us to take in what had just happened. That he wanted the reality, the helplessness, of our situation to set in.

After a few minutes, Sir spoke up. "Cherry, get on your knees and look at me." I obediently got up on my knees and stared intently at my master.

Sir then looked toward Kylie. "Get on your knees and look at me." She immediately obeyed.

Then one at a time, Sir looked at my mother and sisters, and said, "Look at me." They each obeyed immediately.

Sir looked at each of us for a long moment. Though he was silent at the moment, his cocky grin spoke volumes. He won. We lost. We were conquered. He owned us. He owned our bodies. He owned our actions. He owned our thoughts. He owned our minds. He owned our souls.

"It's time for bed for all of you. Go get showered, and go to your respective rooms. Except for Cherry. After you've showered, clean up this floor. Then you can come to sleep in my room."

Now that he had completely and unquestionable demonstrated his power, was Sir going to allow me into his bedroom? I was ashamed to admit this to myself, but I felt a sense of gratitude and accomplishment that Sir would allow me to sleep with him. Not just be fucked by him, but to sleep with him.