James Explores Ch. 02: Daddy's Girl

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Daddy starts training his sissy.
1.5k words
4.55
32.9k
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Part 2 of the 3 part series

Updated 10/21/2023
Created 09/13/2019
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ShyBiSub
ShyBiSub
49 Followers

All Characters are over 18.

The first part got wayy more views than I ever imagined so I decided to continue ;) Thank you <3

*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.

Memories from Part 1

"Good girl. See you again next week, same time"

He squeezed James' bottom in his hand.

"Yes Daddy"

The Crush

James couldn't stop thinking of what happened that day. He couldn't stop thinking about Daddy... He was being used right? Did he want to be used? James couldn't make up his mind. He'd never allowed himself to acknowledge his attraction to another man. Now he had no choice.

For the first few days, he only felt confused.

Daddy hadn't spoken to him since James left his house on Friday. James was glad, but some part of him missed Daddy. He kept checking the sissy RP chatroom, but Daddy never came online.

Tuesday - 23:14

BigDaddy248 is typing...

James could feel his heart beating faster. He gasped when he noticed the bulge in his pants.

BigDaddy248 wants to send you a picture

James clicked accept. A picture of him wearing a pink collar appeared on the screen, he was bent over Daddy's shoe.

BigDaddy248: You have homework this week, as part of your training. One task a day. You will provide a photo of each completed task. If you don't complete all the tasks by Friday, this image is going to all your friends.

James hesitated. He didn't even notice his other hand instinctively rubbing over his bulge.

JustCurious19: Yes Daddy.

James waited in suspense. At exactly 00:00 a list appeared on his screen.

1. Dildo training - A sissy should be able to fit their entire dildo in both their mouth and boypussy.

2. Clothing - A sissy should wear panties every day, and must always dress femininely in order to be identified.

3. Slut training - A sissy must practice being a proper slut, and give at least 2 strangers blowjobs.

4 Obedience training - A sissy must report to Daddy every morning for inspection, and obey all commands.

5. Girl training - A sissy must be able to orgasm from penetration only, without touching her clitty.

PS. Your curtains may never be closed this week.

BigDaddy248 has sent you a link

James clicked the link. It was an installer. After clicking "accept", the software opened up. A live feed of James popped up, the software was streaming his laptop's webcam. It had a chat section to the side of the video feed.

Good girl

James blushed.

Time for task 1

James carefully got undressed in front of the camera. He pulled the box out of his closet and put the collar on. Daddy didn't ask him to, but it felt right.

James thought he'd try fitting the dildo in his mouth first. It was a bit smaller than Daddy so he knew he could take it.

He looked into the webcam and played with the tip of the dildo. His mind was flooded with reminders of sucking Daddy. He smiled and asked "Please Daddy", before pushing the dildo between his lips. His mouth moved up and down the shaft of the dildo. He decided to try and take it all the way. The dildo pushed into his throat and he gagged.

He pulled it out and coughed a few times. His mind was already lost. He tried again, but forced himself to keep it in.

The stream's chat had a notification:

Daddy: Good

James slipped the dildo out of his mouth. After he caught his breath he looked back at the webcam.

"Thank you Daddy"

He re-positioned and covered the tip of the dildo in lube. He'd never been able to fit more than a finger before... He rubbed the head around his boypussy before pushing it slowly. James relaxed his muscles and squeezed the tip of the dildo into his hole. As it slid in he let out a girly moan.

Daddy: Take it out. Beg for it. Then fuck yourself.

James paused and tried to relax his muscles first. He pulled the dildo out and as the head popped out of his hole he moaned again.

"Please Daddy, fuck me. I need you in me Daddy. I want your cock."

He gently bit onto his bottom lip.

Daddy: Stop.

James was shocked. Did he do something wrong? He wanted to please daddy.

Daddy: Come over. Now.

James was too horny to resist. He slipped his pretty pink panties over his lubed bottom. The collar was still tightly holding onto his neck. He went to the bathroom and tried to make his hair look like less of a mess. He wanted to be cute for Daddy.

It was dark outside, and cold. James rushed over to the big wooden door, wearing nothing but the panties and his collar. He stopped for a moment. Everything felt surreal. He couldn't possibly be doing this?

The door opened. James rushed inside, wanting to escape the cold.

Daddy stood there, quietly. James could see his erection through his pants.

Daddy gestured a turning motion with his hands. James turned around and presented his bottom to Daddy. He smiled as he wiggled his cute pantied ass.

Daddy walked up behind him and put his hands on James' hip.

"We're changing the training a bit. From now on, as soon as you wear that collar you are no longer James."

James nodded. His heart started pounding faster in anticipation.

"This collar says good girl on it. James' isn't a very girly name, is it?"

"No Daddy"

"The only person I know that wears this collar is Sissy Jessica, so you must be Jessica"

"Yes Daddy"

"What's your name?"

"Sissy Jessica"

Daddy gripped Jessica's hips and pulled her closer. He grinded on her bottom as he gently kissed her neck. Jessica couldn't hide her excitement.

"Please Daddy"

Daddy easily lifted Jessica into his arms and carried her to the bedroom. She kept looking into his eyes, biting her lip.

Daddy threw her onto the bed. He proceeded to open another black box nearby. Jessica couldn't see what was inside.

Daddy reached into the box and pulled out a set of restraints and a gag. He tossed them onto the bed and smiled.

"Off the bed, on your knees"

Jam... Jessica got off the bed and dropped onto her knees. Her mouth opened.

Daddy came closer, holding the gag in his hand. He teased Jessica's mouth with his finger before spreading it open. Then Daddy placed the pink ball gag into Jessica's mouth and secured it's strap around the back of her head. She started drooling.

Jessica tried to talk, but the words only came out as incoherent muffled sounds.

Daddy lifted her onto the bed, with her bottom up. He then slowly went to each bed post and tied Jessica to the bed. He started with her arms. Then her legs. It felt like an eternity.

Jessica tried to move around a bit, but she wasn't going anywhere. Completely vulnerable. Daddy had full control. She felt his hands pull down her panty. The restraints kept Sissy Jessica's legs apart, making her feel even more exposed.

Jessica heard Daddy unzip his pants. She couldn't move her head enough to see what was behind her. She heard the pants hit the floor. Then silence. After a few seconds she could feel one of Daddy's hands cup her ass. He moved the hand closer to her hole. A finger slipped in and Jessica pulled against all the restraints as her boypussy was violated. Another finger followed, and then another. Jessica wiggled her bottom as she tried to talk.

"Pwsh Dddy, Fk mmmm"

His fingers pulled out, and took hold of her hips. She felt his tip touch the outside of her hole. Ja-Jessica needed Daddy's cock. She pushed back as far as possible and relaxed her muscles. As the head of Daddy's cock entered her waves of pleasure flooded her entire body. She moaned loudly, but only a soft squeak escaped the gag.

Daddy started slowly. Jessica wiggled and squealed every time he pushed. Then Daddy started going faster and harder. Jessica tightened around his thick cock as he started fucking her like a whore. Her sissy clitty was fully erect and dripping precum.

Every time Daddy hit her g-spot she got closer to orgasm.

Daddy's grunting grew louder. His grip tightened.

"Cummm innn mmee Daaddeee"

Daddy pulled Jessica closer and pushed all the way into her. She felt his thick cum fill her as she let out another girly moan. He kept his cock in her for a while. Jessica could hear his breathing calm down. He carefully pulled out. As his head slid past Jessica's hole, another wave of pleasure hit her.

Daddy got up. First he moved to the front of the bed. He leaned over, kissed Jessica on the cheek and removed the collar.

James looked into Daddy's eyes. He could see Daddy smiling.

Daddy walked away and took something else out of the box. He felt something hard press against his boypussy. Another dildo? It slid in easily. James heard something click and the dildo started vibrating.

Daddy's footsteps sounded further and further. The door started to shut.

"Good girl"

ShyBiSub
ShyBiSub
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4 Comments
AnonymousAnonymousover 1 year ago

I love the story it is good

AnonymousAnonymousover 4 years ago
keep more cumming

Love the way daddy is making jessica his. Can't wait for the next training session.

sissyjolie4usissyjolie4uover 4 years ago

love the way this is developing, do continue

petey377petey377over 4 years ago
wow

what a lucky gurl Jessica is to have such a hot daddy hope there will be more

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