The Secret of the Island Pt. 02

"Good work sissy boy. You finally did it."

"Huh? Jerome what do you mean? What did I do?" Jenny asked a little confused.

"I'm not talking to you baby. I'm talking to your asshole ex-friend."

"Sony? He is here? I don't want him to see me like this." She panicked.

"Too late for that. It was he that made you look like that."

"W- what do you mean sugar? Y- you've been here with me the whole time." She was getting more and more confused.

"Are you sure? If you are then remove that blindfold off your eyes."

"I can't do that. You cuffed my hands together behind my back."

"Oh I see. Well then. Sony! Stay where you are and slip the blindfold off her eyes. Quickly!"

Sony reached back and took the blindfold with his fingers and pushed it over her head. Jenny opened her eyes and saw the most horrific sight she ever witnessed. Sony's ass was barely above her face while Jerome was in the middle of the room. Her eyes watered and she began to cry loud. Sony was getting very afraid and Jerome was looking even more furious.

"How long... have you been staying there?" Finally Sony managed to mutter.

"Oh I just got here. But I saw the whole thing while Daisy was enhancing me. I couldn't contain my anger, I had to endure everything and believe me when I'm saying this. You are not getting out of here alive you bastard."

"Jeromeeee" *sob* *sob* "I'm sorrrryyyyyyy." *sniff* "I had no ideaaaa." Jenny was still crying, tears covering her entire face.

"It's not your fault Jenny, I'm not mad at you. You however..." He pointed at Sony. "I cannot forgive."

Sony was shaking and was about to piss himself when Jerome continued.

"I am not a person who doesn't protect his friends and seeing you do all these awful things to my friend after you insulted her so much, well, things are not looking good for you. But don't worry. I'm not unreasonable man. I'm going to present you with 2 choices. Either I beat you here and then fuck your ass until you die or you do the cowardly thing and repent for your sins. What will it be fucker? And I really want you to kill you, so I hope you make the stupid decision."

"I'm sorry; I'll repent for what I did and said. Please have mercy, don't kill me." Sony was starting to cry.

"Well that seems like a good choice. For you at least. Get over here this instant. NOW!" Jerome yelled.

Sony quickly stood up and ran to Jerome who was waiting furiously for him. Sony looked up at the towering man and just as quickly lowered his head down and closed his eyes. Jerome reached with his big hand and grabbed his neck leading him out.

"Daisy open the chamber! We have new customer for you." Jerome instructed.

"Yes of course. Enjoy your stay! Hihihi."

The chamber opened and Jerome pushed Sony inside. Where the equipment grabbed him and forced him to stay put.

"Now you stay here and think about what you've done, while we're discussing what to do with you." Jerome said and the chamber closed and lowered in the floor.

Jerome quickly turned to the room and get to Jenny as fast as he could. He unlocked her chains and pulled Jenny so she was sitting now. She looked down to see her cute cock covered in shit and her cries began again.

"Shhh, it's ok, we can fix it. Daisy will prepare a bath for you and we will get you cleaned up. I promise." He tried to calm her down.

"Ok, thank you." She smiled and stopped crying.

"The bath is prepared. Is jenny ok?" Daisy informed them.

"She's fine. Thanks for telling me about that little fucker. Now go get in the bath baby, you'll feel better."

"Thank you again, I'll be right back." She wiped her tears and ran for the bathroom.

Jerome sat on the bed and put his hands on his head. He didn't expect things to turn like this. If it was up to him he would kill that son of a bitch so he would never do anything like this ever again. But he decided that it would be best if he let Jenny figure out what to do with Sony. Then he got an idea. He stood up and called for Daisy to show him the answers on his test. What he found stunned him.

"There is no way any of this is true." Jerome laughed while looking at the screen in the test room.

"That is what he answered. His intentions are very different however. For example, he prefers to be on bottom during sex, the whole thing now was just an act. You saw him yourself how he eagerly fucked himself on Jenny's cock. Also fantasizing and actually having sex with a man or a tranny is something he has done in the past and he even participated in a threesome with a man and a tranny with him being spitroasted by them while they took turns on him. Another thing he lied about is his size."

"Yeah I saw it. If that little thing is even a third of what he said I'd be fucking surprised." Jerome laughed.

"Next are the blowjob questions. The only reason he is unsure about them is because he doesn't know how people will handle his little dick. If you're ready we can start his transformation now."

"Hmm, I want to leave that to Jenny. I think she deserves it after what he did to her."

"Agreed. Oh look there she is. I helped her get cleaned up and it looks like she is ready to go. She is mentally stable for now so you shouldn't waste your chance. Go and give it to her!"

"Wait. How did you help her? You were talking to me the entire time."

"Multitasking. How many times do I have to explain how advanced I am?"

"Oh right. Well, wish me luck."

"You don't need luck. You got a big dick and a sexy tranny sex slave who would do anything for you."

"Thanks Daisy, you are the best."

"I never get tired of hearing that."

Jerome went in the sex room and found Jenny examining the sex toys on the walls. He leaned on the door frame and whistled. Jenny heard him but she did not turn, instead she stood there and swished her ass invitingly. Jerome understood her intentions and slowly came closer to her. She heard his footsteps coming closer and closer until he finally stopped behind her back. He reached with his arms in front of her and grabbed her giant tits. She moaned and moved her hands to his guiding them where she wants. Jerome pinched her nipples and she let out a silent "Oohh." He then moved his right hand to her belly and then down to her soft penis. Just one touch was enough to instantly get hard inside his hand. Jerome liked that and responded with his own cock touching her ass. Jenny felt the giant snake and understood what she was supposed to do. She opened her legs and spread her butt cheeks inviting the monster to come in. Jerome had other plans. He pushed the base of his flaccid dick upon her hole and let her cheeks snuggle it in place. She was curious about what he was planning. Jerome grabbed her tits again and massaged them as best as he could, making the horny girl moan with ecstasy. Jenny bit her lips and felt his big cock hardening; he liked her girly moans and she liked his cock. But instead of penetrating her Jerome's cock was going underneath her and lifting her up. It was big and strong but it still wasn't fully erect, it was still enlarging. Jenny looked down at it dwarfing her little pecker and smiled. She wondered if she could actually take the whole beast inside her. It was already bigger than the dildo Sony used on her and was still growing lifting her higher and higher.

"Think you can take it beautiful?" Jerome whispered in her ear.

"I don't know." Jenny answered a little scared.

"I know. Hold on."

Jerome grabbed her hips and lifted her high in the air, turning her upside down.

"I figured we could try another 69 but standing up now."

"Oh you're so big and manly." Jenny said inhaling the masculine scent of the dick in front of her face.

"Are you talking to me or my penis?"

"Whichever makes you hornier big boy." *giggles* "You want a blowjob before you stick it in?"

"Unless you want me to go in dry..."

"No, a blowjob sounds good. Can you return the favor if you don't mind?"

"Anything for you pumpkin."

Jerome began the action with a tongue on her clitty and immediately engulfing it in his mouth while Jenny was spitting on his rod and wiping the saliva all over his length. Finally she took it with both hands and guided it towards her hungry mouth locking her lips around the head, trying desperately to lube it for the grand show. Unfortunately this proved rather impossible seeing as Jerome was much bigger than last time thanks to Daisy's improvements. But that didn't stop Jenny from her goal, lubing the giant snake could be done outside of her mouth as well. She took it out still covered in her saliva and just as before she rubbed all over it making the cock shine. Meanwhile Jerome was already putting 2 fingers inside her hole, stretching it and playing inside it while still sucking her little cocklette. He sensed her tensing and ready to cum so he withdrew his fingers and let go of her clitty.

"Why? I was so close." Jenny sounded disappointed.

"I think this is enough foreplay. Let's get you filled up." Jerome said while getting her down.

"Can we do a little accessorizing first?"

"What do you have in mind?"

"How about cosplay? Daisy said we can try different outfits so I was wondering if we could dress up and fuck like that."

"Nah, I don't think anything would suit me. I don't mind you dressed up."

"Sweet. Be right back. Daisy? I need your help."

"Of course. Go to the room next to the bathroom. It is full of everything you desire."

Jenny quickly ran out of the room before showing again at the door to leave a blow kiss to her lover. Jerome was left alone and he looked around the room examining the toys Jenny was looking at earlier. He grabbed a bottle of lube and applied it to his massive member. "Jenny did a good job but I better be prepared, I don't want to hurt her." He thought. Looking around again he took several items - a ball gag, a pair of handcuffs and a funny looking helmet with handlebars on both sides. He turned around and there she was. Jenny was ready, stunning leaning on the door all dolled up wearing a school girl uniform, tied up white shirt covering and keeping in place her tits although leaving her belly exposed, a very short plaid skirt barely covering the black lace panties underneath, thigh high white and blue striped stockings and black 6 inch platform boots. The only things missing would be nerdy looking glasses and a lollipop in her mouth.

"Wow. Class is in session. And you're late. Looks like you need to be punished." Jerome said while checking her over.

"Aww, isn't there anything I can do to make up for it? Maybe do something... for you?"

Jerome sat on the bed and called Jenny over. She came closer and he pushed her over his lap lifting her skirt and exposing her panties. He grabbed them and pulled them up giving her a wedgie of some sorts making her moan and shake with anticipation.

"If you're a good girl you will take your punishment and we will continue, understand? 10 spankings on that ass would be enough to loosen you up."

He slowly placed his right hand on her smooth cheeks and rubbed them gently before lifting it and smacking it hard making her squeal.

*smack*

He repeated the action a few more times.

*smack*

*smack*

*smack*

*smack*

*smack*

*smack*

*smack*

*smack*

Suddenly he stopped. He took her chin and looked in her eyes. She was smiling but also tearing up. The pleasure and pain were mixing together but she was happy.

"You weren't counting. We have to start again."

*smack*

"One."

*smack*

"Two."

*smack*

"Three."

*smack*

"Four."

*smack*

"Five."

*smack*

"Six."

*smack*

"Seven."

*smack*

"Eight."

*smack*

"Nine."

Jerome stopped again. He was enjoying this and it looked like Jenny was enjoying it too.

"You forgot to say thank you when you count. One more time."

*smack*

"One. Thank you."

*smack*

"Two. Thank you."

*smack*

"Three. Thank you."

*smack*

"Four. Thank you."

*smack*

"Five. Thank you."

*smack*

"Six. Thank you."

*smack*

"Seven. Thank you."

*smack*

"Eight. Thank you."

*smack*

"Nine. Thank you."

"Thank you what? You forgot to say "master". This is the final time."

*smack*

"One. Thank you, master"

*smack*

"Two. Thank you, master"

*smack*

"Three. Thank you, master"

*smack*

"Four. Thank you, master"

*smack*

"Five. Thank you, master"

*smack*

"Six. Thank you, master"

*smack*

"Seven. Thank you, master"

*smack*

"Eight. Thank you, master"

*smack*

"Nine. Thank you, master"

*smack*

"TEN. Ugh, thank you master."

"Did you learn your lesson?"

"Aww my poor bottom. I don't think I can sit down for a week."

"Let's test that statement! Stand up and remove your panties!"

"Ok. Ow, even the panties brushing against my skin make it sting."

"Don't worry, I will make you feel real good now."

Jerome turned her around and grabbed her hands cuffing them behind her back. Next he inserted the ball gag in her mouth and locked it in place. He laid down on the bed and motioned for Jenny to climb on him.

"You know the drill, use your hands to guide my cock to your pussy and then ride it at your own pace. If you have trouble or you can't do it anymore, I'll push you face down and do it at my own pace."

Jenny climbed in the bed strutting herself on her knees on top of Jerome almost falling twice. With her hands cuffed behind her and with the high boots on her feet it was very difficult to adjust her body but she managed somehow. As soon as she got comfortable on his lap she reached behind to grab the giant rod waiting for her. She finally found it and traced the head along the length to stuff it in her hungry hole. It was so long that she had to lean forward and then insert it but her heavy breasts made her lose her balance and she collapsed on Jerome's chest. Jenny looked him in his eyes and he just smiled.

"Is it too much trouble for you my lady?"

"Mmm..."

"Do you want my help?"

"Mmm..."

At that moment Jerome grabbed his dick and guided it to her entrance. She noticed it was lubed and relaxed her muscles ready to take the behemoth inside. The head pressed against her opening and she began her moans. Jerome was careful to not hurt her so he pushed it slowly but steady inside. Every second another centimeter disappeared inside her until it reached a point where it couldn't go any further. And that was only half of it.

"Are you ok?"

"Ah-ha."

"Shall I begin moving or do you want to do it?"

Jenny couldn't speak but it was obvious in her look that she was determined to squeeze every drop of cum with her own skills. She was still laying on him when she began her little shuffle back and forth releasing some of his length and immediately stuffing it back inside. Jerome grabbed her small frame and lifted her so she was up on his dick impaled by the monster. She didn't waste a moment and started bobbing up and down on the shaft, up and down sliding the wet pole in and out. The pleasure of it all was overwhelming, tilting her head back she closed her eyes while Jerome grabbed her tits and massage them, rubbing them and pulling them in every direction he could before dropping them to bounce down again like she was doing on her own. Jenny was getting tired of this position and the giant cock wouldn't let her sit and relax.

"Wanna change position? I mean if you're tired?"

"Mhm."

"Roger. I got another surprise for you."

Lifting her off his cock Jerome took the helmet and put it on her head securing the straps in place and leaving her like this. Next he uncuffed her hands only to cuff them back in front of her.

"Get on all fours bitch. It's time to take this bike on the road and I wanna ride it to hell and back."

With this Jenny complied and did as she was told lifting her red ass in the air while Jerome was slamming his meat inside her again. He grabbed the handlebars and pulled lightly while inserting his dick further in, leaving her moaning and groaning, arching her back and pushing her ass in the air.

"I like to fuck a bitch while riding my bike, don't you agree? Heh heh. You don't have to answer, just keep making those noises you do, it makes me more excited."

"Mmm. Mhm. Mmmaaahhhh. Aaahhhhh. Mmmm. Ahhhhh."

Suddenly Jerome let go and her head fell down, she was drooling all over the bed and it looked like her little clitty was drooling too. It was time to finish this. Jerome withdrew his penis and got off the bed, walked to the accessories rafts and took a small collar with "Bitch" engraved on it. He went back to Jenny who was still processing the situation and removed her helmet, throwing it aside.

"Turn over! Lay on your back!"

He put the collar on her neck and then chained the cuffs to it, making it impossible to move her hands much as they were literally pressed against her face. He removed the ball gag, allowing her to swallow and then got in between her legs, pushing them apart and lining his manhood to her gaping pussy.

"This is it baby. I'm gonna make you a woman now, if you weren't before. I'm gonna cum so much inside you I'm gonna impregnate you."

"Fill me up! Do it!"

He pushed himself inside her sliding in and out for the final showdown. He took her legs and pushed them up on his shoulders while leaning over her and making her bend her body. This was apparently working best as she loosened up and he pushed even more of his meat inside her. Almost the whole length was inside when Jerome quickened the pace, rubbing her insides, stimulating her weak spot. She was licking her fingers, sucking them and drooling all over herself, moaning and panting waiting for him to empty his load.

With one final thrust he pushed everything inside her and huge hot jets of sperm hit her intestines filling her up slowly. He pressed his entire body to her ass and she clenched not wanting to spill anything. The cum was overflowing and flooding her pussy while expanding her. The feeling of being so full of warm liquid threw Jenny over the edge and she spurted her own jets of pent up clear cummies hitting her in the face. Jerome's eyes rolled back while he continued to pump more of his hot seed inside making her belly expand to almost three times its normal size. Finally he felt that he was indeed empty and he began pulling out.

"Keep your ass tight, don't spill anything. I'll go get something I forgot earlier."

"Mmm yes, master."

Jerome pulled out with a loud plop and her ass quickly closed. He went to the toys and took a really massive buttplug, 15cm long and 5cm wide, it would surely stay inside her for a long time. He got back and pushed it up her wet pussy. She knew what to do and relaxed it swallowing the big plug and saving it inside her.

"Well how is it? Did you get everything you wanted?"

"More than I dreamed of. It's so much I might really get pregnant."

"Well I doubt that would be happening but you sure would make a great mommy."

"And you would make a great daddy... daddy."

"Thanks to Daisy's tech I think I can go again now. What do you say? One more round?" He said and unlocked her cuffs.

"No. I am tired now. I want to sleep for a while. And your cum is so warm inside my it's making me even more sleepy.

"Ok, princess. Sleep tight."

Jenny relaxed herself on her left side and closed her eyes. Jerome smiled and tapped her ass lightly before leaving the room.

"Ouch. Hey, I'm still sensitive after the beating you gave me."

"Oh sorry. I didn't think I... I'm going now. You rest."

Jerome left the room and remembered Sony. Now was the time to deal with him, maybe even fuck him up or turn him into a sissy bitch. Unlike Jenny it wouldn't be his choice and it would be a punishment instead of a reward.

"Daisy! It's time to give Sony a makeover. I want another sissy in my harem."