James Explores Ch. 01: Meeting Daddy

I'm still a newbie so any tips appreciated :)

Note: The main character is 19. Any school/class mentioned refers to university (I know some of the terms differ internationally).

I hope you enjoy this short fantasy of mine <3

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Moving out

Moving away from home was intimidating. James was fairly independent, but he had never been on his own for more than a week at a time. It was exciting though... a fresh start. Privacy.

James' parents were very conservative. Girls were never allowed to stay over, and he constantly had to report back home when out. He usually didn't mind following rules, but there were parts of his life that he knew he couldn't embrace at home.

James has had girlfriends before, but there were parts of his sexuality that he still wanted to explore. He'd sometimes fantasize about crossdressing, making out with guys. Never more

A new friend

After a week in his new apartment, James finally started settling in. The first week of university was busy, but manageable. The weekend arrived and he finally had some time off.

A combination of boredom and curiosity convinced James to find an online chat room. "Sissy RP". He could feel his heart beating faster as he clicked the link.

Choose a username:

After staring at the screen for a few minutes, he typed.

JustCurious19 has joined the channel

He waited a few minutes, no response. After losing hope, James started moving his cursor onto the tab X.

BigDaddy248: What are you wearing?

James hesitated.

JustCurious19: Just a T-shirt and pajamas shorts...

BigDaddy248: Take the shirt off.

JustCurious19: What..? Why???

For the next 10 minutes, he received no response.

BigDaddy248 wants to send you a picture

James clicked accept.

A picture of a guy wearing panties appeared on his screen. He knew the guy. It was him.

BigDaddy248: Now. Apologise and take off your shirt, or I'll be leaking these to all your new friend.

James panicked, he didn't know what to do. He felt exposed.

JustCurious19: I'm sorry! Just delete the pics, wtf!!

BigDaddy248: You will refer to me as daddy from now on. Or else.

JustCurious19: Sorry daddy...

After clicking "send", James closed the chat immediately. He shut the laptop and flopped into bed. He was breathing quickly.

James fell asleep.

A Gift

Someone rang the doorbell. James struggled to get up. They pressed the doorbell again. He rushed to the door. When he opened it, no one was there. He started closing the door when a small package caught his eye.

It was a neat black box that was decorated with a cute pink ribbon. It had a card attached to the top. The card was addressed to My Sissy .

James was too scared to open the box, but eventually his curiosity got the best of him. He carefully undid the ribbon and lifted the lid. The box contained a pair of pink panties with matching pink collar, a dildo, and lube.

James rushed back to the door to see if anyone was nearby. He saw nobody. He didn't know what to do with the box, and hid it in the back of his closet.

His phone rang.

"Hello, James here"

An older man's voice responded:

"That's strange... I was sure this number belonged to Jessica."

"I'm sorry, no Jessica here"

"Come next door Jessica. It's time to start your training"

"I'm sorry sir, you have the wrong number"

"Sir? I thought you understood that you'd be calling me daddy from now on. Come next door or I'll be leaking more images of you. I'm sure you wouldn't want your parents to find out... 5 minutes, bring your toys."

James didn't know what to say.

The caller put down the phone.

5 minutes

James grabbed the box from his closet. He was about to open the door when he froze. Was he really going to do this? He opened the door. He had no other choice.

He knew which house to go to since his other neighbors were a pair of girls sharing an apartment. He walked up to the big wooden door and reached out to ring the bell.

The door opened.

A well built older man stood in the doorway, smiling. He gestured inside, James cautiously obliged. As James walked past the man, the door shut. The man gently took hold of James' wrists from behind. He pushed him against the nearest wall. The harder James tried to resist, the stronger the man's grip became.

James was pinned and too scared to struggle. The man pressed his crotch against James' bottom. James could feel his bulge press against his cheeks. His dick must be massive, James thought. The man leaned forward and planted a kiss on the back of James' neck. It tickled.

The man let go of his wrist, but he didn't move.

"Beg daddy to take off your boy clothes"

James paused.

The man's big hand struck James' bottom. James let out a soft moan.

"Please da-daddy, take off my boy clothes"

The man moved his hands around James' hips. He gripped James' jean zipper and slid it down. His hand stroked against James' penis. It started to stiffen as James let out another moan. He couldn't believe this was turning him on!

The jeans hit the floor. Underpants followed. Then the shirt.

James stood there, naked. The m- Daddy handed James the box and inspected his body as James pulled the pink panties over his soft bottom. He was about to attach the collar himself when Daddy grabbed his hand.

Daddy took the collar. He put his hands on James' shoulders and started pushing him to his knees. James only noticed now how much taller Daddy was than him.

James had to bend his head backwards to look into Daddy's eyes. Daddy brought the collar to his neck. It had a tag on it, reading "Daddy's girl". James blushed

*click*

Daddy put his hands on James' cheek. His thumb massaged the lips. He slipped it into James' mouth and started moving it in and out. James started sucking, he was no longer in control. The sissy porn he had watched so often had taken over.

Daddy removed his thumb and started undoing his belt buckle. James' mouth remained open as he drooled for Daddy. Once the belt was out of the way, James reached to pull down the pants. He couldn't wait anymore.

Daddy's cock was a few centimeters from James' face. The smell drove him crazy. He moved forward to take it, when Daddy pulled back.

"Good sissies ask first"

"Please daddy, let me suck your cock"

Daddy smiled and put his hand on the back of James' head. He rubbed the head of his cock on James' lips, which were now covered in precum. As he slid it into James' mouth, James moaned. He started sucking like a good sissy.

James started stroking himself with his free hand.

James playing with daddy's head with his tongue. He'd seen it in so many videos before. Then he started speeding up, moving his lips up and down Daddy's shaft. He kept looking into Daddy's eyes, and could see him smiling as he grunted to the rhythm of James' movement.

James' couldn't hold it in anymore. His cum shot all over the floor. Some of it got on Daddy's boot. Daddy's cock muffled the sound of his moans.

Daddy began moving his hips more violently. James gagged and tried to pull out for air, but the hand on the back of his head pushed him further onto Daddy's cock. Daddy let out a loud groan and gripped tightly as he came. His cum filled James' mouth and covered his lips.

Daddy pulled out slowly, and put his hand on James' chin. He forced his mouth shut.

"Swallow"

James did.

"Now thank your daddy"

"Th-thank you daddy"

"Clean up after yourself"

James reached out to wipe Daddy's shoes off, when Daddy slapped his hand away. James knew what Daddy wanted and reluctantly leaned forward. He licked the front of Daddy's shoe clean.

*chk*

James looked up to see daddy taking a picture of him.

"All mine now"

Daddy grabbed onto James' collar and pulled him to his... her feet. James stood there. Naked. Covered in cum. Collared. Embarrassed.

Daddy led him to the door and planted another kiss on the back of James' neck as he pushed him out the door.

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

He squeezed James' bottom in his hand.

"Yes Daddy"