Doodle31

Show her the Side-tie panties

by Doodle31

Chapter 8 in Dressing up

Taking a quick look around John couldn't see anyone around, and there were no windows along the bricpk wall. "Promise you won't laugh OK?" John turned around and unzipped his jeans wiggling his butt out exposing soft perky glutes. Before he could turn around he felt a soft litt...

Striped side tie panties

by Doodle31

Chapter 4 in Dressing up

Carefully seeking the selection among his sisters undergarments John finds his eyes drawn to a pattern of pale blue and white stripes. Picking the pick up and examining it he sees the strings dangle on the side. He'd seen panties like this in anime before but had no idea that gir...

Sister's room

by Doodle31

Chapter 3 in Dressing up

At 16 years old, John sister was 2 years younger than him. Her panty drawer stood in the middle of the wall opposite to her bed cracking it open to look for something useable John finds a collection that might exite him too see if it wasn't his sister's.

Of course!

by Doodle31

Chapter 16 in Dressing up

"OK, we'll go." John pretended to be defeated " But while we're there you can't call me John, I need a girly name." "Whatever you say Jenny-girl" Sarah winked at John. "Once your nails are dry put your outfit back on. You are gonna be GORGEOUS" She was right once the outfit was...

A party invite

by Doodle31

Chapter 15 in Dressing up

Sarah walked over to the phone to check out the messages. "It's from Dan they're a party tonight at a cottage by the lake! We should go!" Sarah was jumping for joy. "I'd really like to go but I'm not gonna to hang out with Dan, especially not like this, I'd rather hang out here...

Something sexy

by Doodle31

Chapter 14 in Dressing up

"How about something sexy" John cooed "Babe, we are turning you into a QUEEN" Sarah squealed. Sarah walked John through the make up process teaching him how to apply, contour and finish, as well as style his brows. By the time they were done he had smokey silver eyeshadow to co...

Lips lock

by Doodle31

Chapter 13 in Dressing up

As their lips met Sarah lowered her hand from his face to his legs and turned John's body towards her. She lifted his legs over hers as their embrace continued. John put his arms around Sarah's neck. He crossed his legs and leaned back letting her kisses land on his neck and ches...

A little black dress

by Doodle31

Chapter 12 in Dressing up

Like love at first sight John reaches for a back bodycon minidress with a built in bra and thin shoulder straps. "Oooh, you are such a badie! Try it on!" Sarah is ecstatic with John's choice. John pull off his shirt jeans and socks leaving only his panties. Sarah helps him slip...

Yes

by Doodle31

Chapter 11 in Dressing up

"Honestly I never even thought about it until this morning, yeah I think I really like it" John spoke confidently looking at their reflection in the vanity. "Do you wanna try some new clothes on?" Sarah asked walking over to her closet opening it to show all over her clothes Jo...

Go with her.

by Doodle31

Chapter 10 in Dressing up

The two of them walked to Sarah's place. Neither of her parents were home and the two went up to her bedroom. Sarah may have been a tomboy but her girly side really showed in her room a beautiful vanity by the window with all her makeup was the first thing that caught John's eye...

After school

by Doodle31

Chapter 9 in Dressing up

After a uneventful afternoon of classes John was ready to head home for the weekend. As he unlocked his bicycle a familiar voice reached his ear. "_Hey_" John turned around to see Sarah "Any plans for the weekend?" She was smiling ear to ear. It was obvious she was still giddy...

A little look at the thong.

by Doodle31

Chapter 8 in Dressing up

Taking a quick look around John couldn't see anyone around, and there were no windows along the brick wall. "OK, but just a little peek, I don't need anyone else getting in on this." John turned around and unzipped his jeans wiggling his butt out exposing soft perky glutes. Bef...

I'm wearing womens underwear

by Doodle31

Chapter 7 in Dressing up

Sarah began to giggle uncontrollably. "I could see them while you were sitting in class. You're lucky I was the only one behind you." John begins to blush. He figured his friend might have noticed, there was no point in hiding it, and it was easier to come clean than make somet...

Lunch break

by Doodle31

Chapter 6 in Dressing up

After class, John and Sarah go to their usual spot behind the school for lunch. They sit down a bench by the brick wall on the backside of the school. John checks out Sarah's outfit she's wearing her typical tomboyish style. Jeans and t-shirt not unlike John, but with long blonde...

To school

by Doodle31

Chapter 5 in Dressing up

After a quick trip back to his room to throw on his clothes and grab his bag, John locked the front door and hopped on his bicycle. Feeling his his bum on the bike's seat with his new undergarments was an alien feeling to him Trying to ignore the feeling John speeds up. At the sc...

A black G-string thong

by Doodle31

Chapter 4 in Dressing up

Amongst all the cloths and colors withing the drawer John grabs the simplist black piece his eyes find. Kicking his PJ pants off he slides the slinky black piece up his legs. The piece barely contained his penis, but feeling the string nestle between his buns, John takes a moment...

Mom's room

by Doodle31

Chapter 3 in Dressing up

Running back up the stairs, John ran into his mother's room looking through her drawers swiftly, but carefully. For a woman that supposedly hasn't seen a man in years her collection was impressive, but now was not the time to be impressed John needed something and fast.

To school

by Doodle31

Chapter 5 in Dressing up

High School Senior

by Doodle31

Chapter 2 in Dressing up

The sun peered through the window onto John's face. As the morning sun kissed his face John Doe rolled out of bed. His pale hairless leg shivered as his toes touched the floor. He shook off his dark hair which sat just above his shoulders. Through the corner of his eye he noticed...

Introduction

by Doodle31

Chapter 1 in Dressing up

In this story you'll pick a setting, and in that setting you will inevitably end up crossdressing. It can be by your own will or it can be upon you. Either way you will end up in womens clothes. Whether you become a submissive girly-boi or a beautiful confident queen will...