Mother's Greed Ch. 04

Story Info
Cindy goes a Sissy son a chance.
2.8k words
4.59
27.3k
34

Part 4 of the 6 part series

Updated 06/11/2023
Created 04/18/2022
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This is the fourth story in the series, please read the previous chapters so as to understand the story better.

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Chad watched through his binoculars as Cindy plugged Nikki into the VR. It was the 30th video Chad had prepared for Nikki, there were still 15 more to go. All of them had been prepared by leading experts from his mom's company. Nikki was now deeply conditioned, she wanted to dress feminine and girly, look pretty all the time. She now even did her own makeup and grew her hair even longer. All the pills were taking effects, Nikki thought they were to help her last longer and all the smooth skin, tight ass and budding breasts were temporary side effects. Nikki was locked for 3 months now. She was begging her mother for a release everyday but Cindy always declined. The first 30 tapes prepared by Chad basically altered Nikki's masculinity, she now enjoyed being feminine expect for the sex part. The last 15 videos were exactly for that; they were to turn him into a butt slut and break her clitty. Chad smiled thinking of all this.

Cindy had plugged Nikki into the VR and now she had 4 hours before she would have to unplug Nikki. She went to her room and pulled out her big black dildo which reminded him of Chad. She wanted him in her, but Chad never had sex with her, he wanted her to do some tasks before she got the pleasure. Cindy was determined and had done everything. Cindy stripped and quickly sucked the dildo to lube and then fucked herself with it thinking about Chad. She had an orgasm. She got up form the bed and cleaned herself and cooked dinner. Now it was time to let Nikki out. She went to Nikki's room and removed the VR. Nikki was leaking so much from her caged clitty. Cindy dragged her down to have dinner. After they were done Cindy asked Nikki to come to her room. Nikki followed her.

Once in the room, Cindy ordered Nikki to strip which Nikki did.

"Oh, you have changed so much, you look really sexy now." Cindy said.

Nikki looked in the mirror, her balls were really small now, her cage felt a little loose now. the body was a piece of art; the perfect legs, thick thighs, bubble butt and a slim waist. To complete the set, she had nice pair of A-cup boobs, her long hair was curled into a nice hairstyle, the makeup was perfect. She looked like a really hot girl with a tiny penis between her legs.

"Mom, I have done everything you have asked for. Can we please do it now?" Nikki asked.

"I don't know sweetie. You remember what happened last time, I don't want it to happen again." Cindy replied.

"Mom, I haven't had a release in a month. Could you please at least give me a chance." Nikki pleaded.

"Guess we can try once." Cindy said and removed the key from her necklace.

Nikki was really excited; she was finally getting unlocked. Cindy unlocked her and stroked Nikki's clitty gently, it instantly got hard and started leaking precum. Cindy looked at her sissy son's cock. It was no longer than 2 inch now. the balls were so small now they were not even visible.

"Nikki, I knew you were not ready. See how much you are leaking." Cindy said.

"Mom, I just got excited. Don't worry it won't be like last time." Nikki replied finally happy at the thought of losing her virginity.

"Ok. But still, you are too small to please me. I mean you have already seen my collection." Cindy replied.

"But mom, size doesn't matter that much. I will do my best." Nikki replied.

"No, honey. You are not big enough to please me."

"Mom, please." Nikki begged still leaking through the cage.

"OK, Nikki I'm going to give you a chance to prove yourself. But you must know you have made me very angry by arguing with me and you will be punished after we are done here." Cindy said sternly.

Nikki had stopped paying attention all she heard was, her mother was giving her a chance. She was too excited to be worried about the punishment.

"So, mom what do we do next?" Nikki asked smiling.

"Why don't you sit on the bed, I will be back in a second." Cindy said and went to her cupboard.

She came back with a bucket filled with some kind of jelly.

"Now sweetie, I want you to put your clitty in it and you need to keep it hard." Cindy said and put the bucket infront of Nikki.

Nikki wanted to aske her mother what this was about, but she didn't want to anger her anymore. She got down and pushed her hard clitty into the bucket. After 10 mins Cindy asked her to remove her clitty. She then poured a mixture into the mold and created a silicone replica of Nikki's clitty and handed it to her. Nikki was confused and was about to talk to her mother, when Cindy turned back to go get a box form her drawer.

"As you might have noticed, your cage was getting loose. I didn't want to do anything about it. but I have thought of a perfect punishment." Cindy said.

She opened the box to reveal a chastity cage with the same design ad Nikki's older cage but this was even smaller. Cindy grabbed Nikki's clitty and then squeezed and smacked it, till it shrunk back to its 1-inch from. She then quickly locked the cage.

"Mom, its too tight. I haven't had a release and you locked me again." Nikki cried.

"Hey I was going to give you a release but you were the one who wanted to prove Size doesn't matter." Cindy replied.

"And how am I supposed to prove it to you with the cage on." Nikki replied.

"Nikki, I want you to understand why size is so important to a woman. You have had a sissygasm, you know how to cum like a girl. So, I want you to use the replica of your pathetic clit and have another orgasm. If you do that you prove me size doesn't matter and I will sleep with you." Cindy said.

Nikki was not sure and felt embarrassed when she was asked to have another sissygasm, but she agreed as this was her chance at having sex for the first time.

"So, you will be locked till you have a sissygasm. You can try now if you want." Cindy said.

"Okay mom." Nikki replied.

She wanted a release so bad she quickly pulled her buttplug out and shoved the 2-inch replica inside. She was shocked, she didn't even feel it. it was too short to even massage her prostate. She tried for 30 mins but nothing happened, she didn't even feel that once.

"What's the matter sweetie?" Cindy asked.

"Nothing mom. Its just not happening now, but the dildo feels amazing." Nikki replied.

"Oh, really. That's good, I thought about giving you my favourite toy after you agree your clitty is worthless and won't pleasure me to help you have a sissygasm. But since you like your new toy so much, you can keep using it. just remember you are caged till you cum using this silicone clitty." Cindy said.

Nikki left the room without a word. She went back to her room and tried again for some time but to no avail. She dozed off. For the next 15 days Cindy made Nikki watch the VR videos for the last 15 days. After 10 days of VR. Nikki had a weird feeling of putting something in her ass. she wanted to fill it up. She played with her boi-pussy for hours now, with the replica of her own clitty. The 2-inch dildo didn't help at all. She was even more horny now. The videos got over and Chad asked Cindy to make Nikki watch the last 15 videos again. So, after a month of getting her new dildo Nikki still hadn't cum and was getting frustrated.

So, one morning after breakfast Nikki went to her mom.

"Mom, I agree this is too small to please you." Nikki said.

"Good girl. You finally realised." Cindy replied.

"Yes, mom. But I still need a release. Please mom." Nikki pleaded.

"You have been a good girl, accepting your mistake for thinking that your clitty could please any woman. So, I will reward you." Cindy said.

"Wow, mom. Thankyou."

"I will unlock you. But, just for the day."

"Thank you so much, mom." Nikki said and hugged her mother.

Cindy smiled to herself. The hypnosis videos were programmed to make Nikki's brain think erections are disgusting and painful thing. Cindy wanted to see the effects. She removed the cage revealing an even smaller clitty.

"How does it feel?" Cindy asked.

"It feels a little weird without the cage and it seems even smaller. It is so sensitive now, even the cold air makes me twitch." Nikki replied.

"Don't worry about its size. You know it's not for penetrating." Cindy replied.

"But still, I think it would feel great to have sex with a woman." Nikki replied.

"What do you mean think. Didn't you ever have sex in high school?" Cindy asked.

"No, mom." Nikki replied blushing,

"Well, looking at the size of your clitty I think I know the reason." Cindy replied laughing.

Nikki felt embarrassed. She was a virgin and knew her clitty was small, but she still hoped to have sex with a girl someday. Now, he knew he can't please any woman. Nikki started weeping.

"Oh, sweetie don't cry. So, what you were a virgin, let me give you a hand job to cheer you up." Cindy said and grabbed her clitty.

Cindy only needed two fingers to jerk off Nikki's clitty. Nikki's clitty got instantly hard and she started screaming.

"Mom, my penis hurts a lot. Please make it stop." Nikki cried out.

Cindy smiled; the hypnosis had done its work. Nikki felt a lot of pain when she got hard.

"Baby is your clitty hurting?" Cindy asked.

"Yes, mom. Please help me." Nikki said crying.

"Nikki, looks like your clitty hurts when it gets hard."

"Mom, do something."

Cindy opened the refrigerator and took some ice out and put it on Nikki's clitty. Slowly it got soft.

"Thank you, mom. Oh, no it's happening again." Nikki shouted as her clitty got hard again.

Cindy put the ice back on again.

"Sweetie, you need to stop getting hard." Cindy said.

"Mom, I can't control it. Mom, lock it up, that way I won't get hard again." Nikki replied.

"As you wish, sweetie." Cindy said smiling as she put the cage back on.

Nikki sat down and Cindy sat beside her.

"Mom, what should I do? I can't use my clitty for sex, it even pains when it gets hard." Nikki said crying.

"Sweetie, you know a much better way to have release." Cindy said.

"You mean with my ass?" Nikki asked.

"With your boi-pussy." Cindy corrected.

"But mom I tried with my toy; it didn't work." Nikki replied.

"Don't worry sweetie. I will let you play with my favourite toy tonight; you will have so much fun." Cindy said and went to her room.

Once in her room Cindy texted Chad.

"It is all done honey. Nikki can't even get hard without pain now and her clitty has gotten so small, anyway I am going to let her play with my favourite toy today." Cindy texted.

"Hey, babe. I have a great idea. After showing her the toy blindfold her." Chad replied.

"After that?" Cindy asked.

"Don't worry about it. just blindfold her I will do the rest." Chad replied.

Nikki spent the whole day playing with her butt plug. She was really excited for the night. Around 8 Cindy called Nikki into her room. Nikki went in to see the large 10-inch black dildo lying on her mother's bed. She bit her lip in excitement.

"Looks like you are really excited." Cindy said pointing at her leaking caged clitty.

"Mom can I really use it?" Cindy asked. Thinking about how she longed for something to fill her ass.

"I see you want it quick. Strip first." Cindy replied.

As Nikki stripped Cindy went behind her and tied Nikki's hands behind her and then put a blindfold on her eyes.

"Mom, what is happening?" Nikki asked.

"Don't worry sweetie. I will be back in a minute." Cindy said and then made Nikki sit on the bed and then went downstairs to where Chad was waiting.

"Nikki is all tied up like you wanted. What's next?" Cindy asked.

"You will see." Chad said stroking his hard cock over his pants.

"Are you going to fuck her?" Cindy asked.

"Yes." Chad replied.

"But I have been asking for so long. And she gets it." Cindy said with a crying face.

"Babe, you forgot the reason I didn't have sex with you." Chad said.

"And what's that?" Cindy asked frustrated.

"I said I didn't want to do it, because you lived with another male." Chad said.

"How is fucking that sissy going to change that?" Cindy asked.

"Have you seen the sissy; she looks like a hot chick. The only thing left is for her to forget sex as a man and do it as a woman. After she does that, she will never be a man to me. Then we get down to business with you sexy." Chad said kissing Cindy.

"Then let's get it over with." Cindy said and started walking towards her room.

"Just remember Nikki thinks she will be using a dildo, you help her." Chad said.

"Sure thing, honey." Cindy replied and got into the room.

Nikki was still sitting on the bed naked. Her feminine figure and smooth hairless skin made Chad's dick hard. He stripped and sat on the sofa.

"It's time sweetie." Cindy said and guided Nikki's hands to Chad's cock. Nikki had to use both her hands to grab his cock.

"It feels so bigger than it looked." Nikki said jerking it.

"Suck it honey, lube it for your boi-pussy." Cindy instructed.

"Yes, mom." Nikki said and slowly started sucking it.

Slowly taking more and more. Nikki really liked the taste and couldn't stop herself from sucking more. All the hypnosis had turned her into a cum hungry whore without her knowing it.

"Mom, it tastes so good. I can't stop." Nikki shouted.

Chad looked down at her sissy classmate sucking his cock and claiming it to be tasty. He looked up at Cindy. She was about to laugh loudly, both of them controlled their laughter.

"Glad you like it sweetie." Cindy replied.

Nikki continued sucking the dick and the balls.

"It's not bad considering its your first time." Cindy commented.

"I know mom, but the taste is so good that I can't stop." Nikki said and continued sucking for another 10 mins.

"Don't you want it in your pussy?" Cindy asked.

"Yes, mom." Nikki replied.

Cindy guided Nikki to her bed where Chad was already lying, Nikki got into a cow girl position with Chad's dick below her. Slowly Cindy lowered Nikki down and Chad's cock slowly penetrated her. Nikki loved the feeling, the big black cock filling her tight pussy made her feel so great, she tightened her ass and started bouncing up and down on his cock.

"Mom this feel so good. I don't even care I have a useless clit; I love masturbating from my boi-pussy." Nikki said.

"Good girl, once you experience this. This will be the only way you would ever want to cum." Cindy replied.

Nikki continued getting fucked for quite some time. Chad and Nikki were both at their limit. Nikki's prostate was getting rammed constantly soon she gave up, her legs shaked like crazy and she squirted all over Chad's chest. Nikki continued squirting ropes after ropes of cum.

"Nikki, you have made such a mess. Don't stop fucking your pussy and clean the mess." Cindy said.

"Mom, I can't see how am I supposed to clean up?" Nikki asked.

"I'll help you." Cindy said and scooped up some of her cum and shoved it into Nikki's mouth.

"Mom what was it. it tasted good." Cindy replied.

"It was your sissy juice, now eat some more." Cindy replied before Nikki could say anything.

Chad was about to cum and so his penis started twitching, Nikki felt it.

"Mom why is your dildo shaking?" Nikki asked.

Just then Chad came in her ass. he completely filled it with his cum and then removed the blind fold. Nikki slowly opened his eyes, his confused expression slowly turned into shock.

"Hey sissy bitch." Chad said laughing.

To be continued...

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6 Comments
4yourpleasureiam4yourpleasureiam10 months ago

I just came I am a sissy. I love mom and chad

Al_AnonAl_Anonover 1 year ago

Not a fan of the hypnosis & body modification. Or the bully wanting to fuck the sissy.

AnonymousAnonymousover 1 year ago

Wow

AnonymousAnonymousover 1 year ago

Chad is dead set on fucking Nick than his mother LoL. I wonder who is more masculin. Chad or Nick who with only goal without hypnosis is fucking his mom. Does wanting to fuck a sissy more than a real woman make you more manlier I wonder.

SecretHornySissySecretHornySissyover 1 year ago

It's always the stories that scare you the most that make you leak the most. Holy shit.

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