Dorothy Does Oz Ch. 05

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Dorothy meets some unfriendly apple trees.
4.8k words
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Part 5 of the 9 part series

Updated 10/25/2022
Created 11/17/2004
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05. Into the Deep Woods

Dorothy, Toto, and Scarecrow decided to follow the road that curved south, although none of the group knew where either path led. The cornfields seemed to stretch on for as far as they could see, so one path seemed just as good as the other. As they followed the yellow brick road, Dorothy told the straw man her story and how she had come to Oz. They were able to walk for over an hour before the sun had set too far and the path grew dark.

"I suppose that we're just going to have to sleep by the side of the road, Scarecrow," Dorothy said as she set Toto down on the ground. "It's been a looong day, and I'm going to sleep like a rock, even if it's on the side of the road." Dorothy yawned and stretched, and the Scarecrow enjoyed the view of her tight dress straining against her ample breasts. She sat down on the grassy shoulder of the path and pulled out the cloth from her picnic basket. "I think that both of us can use this as a pillow..."


"You can have it," Scarecrow said. "You forget that I don't need to sleep. In fact, I don't have eyelids, so I don't think I could sleep if I wanted to. You just catch some z's and I'll stand watch, make sure that nobody causes us any trouble."

"Sounds good to me. I'll see you in the morning." Dorothy curled up, laid her head down on the cloth and closed her eyes. Moments later her breathing slowed as she dozed off. Toto pushed his way between her arms and leaned against her chest before he began lightly snoring next to her.

Scarecrow paced the path for half an hour before getting bored and sitting down beside the pair. Sure that the girl was sleeping, Scarecrow lifted up the edge of her dress, allowing himself a long view of her naked ass. He slid his hand under her dress and touched her right cheek, causing Dorothy to reflexively kick back and knock Scarecrow over into the corn. He got up and was relieved to see that she was still sound asleep. Then he noticed the little dog staring at him, his ears flat to his head. Scarecrow decided it would be best to resume pacing the path for the rest of the night.

***********************************

Dorothy woke up the next day, gave Toto and herself breakfast and then the three began walking again. It wasn't long before they could see something on the horizon, above the tops of the corn stalks. They couldn't tell what it was, but they knew that it wasn't more corn and that was what was important. The farther they walked, the closer the darkness on the horizon got and soon they could make out the forest at the end of the field. They began picking up their walking pace as they neared the trees.

"I can't wait to get past these fields," Scarecrow said.

"I would think so," Dorothy replied. "You've never been outside of them before. I've only been in them for a day and I'm already tired of the same old scenery."

Toto let out a bark in agreement as he raced along side of them.

As soon as they passed into the shadows of the trees, Dorothy could feel the temperature drop. "Brrrr, it sure was a lot warmer in the sunlight. I hope that this forest doesn't go on as long as the fields did." Looking down the path, it was trees as far as she could see, but there was some thing else by the side of the road. "Look! Apples!" Dorothy picked up one of the apples from the ground and then spotted the trees that they had fallen from. "I'm going to grab a few of these, Scarecrow. I don't know how long it will be before we're out of these woods, and it can't hurt to have more food with us." She walked off of the path, leaving Toto and Scarecrow behind. There were several branches low enough for the stripper to reach, but she still had to stretch to reach them. She grabbed one red, round apple and pulled it off with a snap.

"Ow!"

"What did you say, Scarecrow," Dorothy asked as she looked back to the road.

"I didn't say anything. Maybe it was an animal."

Dorothy glanced around but didn't see any animals around them besides Toto. She reached back up for another apple. As her her fingers touched the apple, the voice spoke again.

"That's it," the voice said. Suddenly, one of the tree's branches swept out and grabbed her outstretched arm and lifted her off of the ground. "I'm tired of people always grabbin' my apples when ever they like." The branch twisted around until Dorothy was facing the tree. Before her eyes, a face formed in the bark with two eyes and a mouth. "There's plenty of apples on the ground but noooo... They have to yank ‘em right off my branches!"

Dorothy didn't know what to say. This was definitely a new situation to her. "I'm sorry," she began, "I didn't think that you'd mind..."

"Hmmph," the tree grunted. "Didn't think I'd mind? How do you think I'd feel about somebody yanking a apple off a me? How would ya like it if a yanked of one of yer apples?" A finger like stem reached out and poked one of Dorothy's round boobs as the tree said this.

Another voice came from the tree to the right. "I don't think she's got any apples under there... Looks more like a couple melons to me, huh huh."

"Why don't we check," said another tree.

Back on the path, Toto began barking furiously. Scarecrow knew he had to do something and rushed at the tree holding Dorothy only to be knocked back to the bricks by a large branch.

The middle tree slid a branch onto the neckline of Dorothy's dress and pulled it open letting her large breasts tumble free. The cold air of the forest had made her pink nipples very erect.

"Hey!" Dorothy shouted as she tried to kick out at the tree. She couldn't reach with her feet, but she slapped a branch away with her free hand as it poked her right breast. "I'll give your fucking apples back! Just put me down."

"Too late for that," said one tree.

"Yeah," said another. "Too late for that, huh huh. Why don't we see if she's keepin' a peach under there, too?"

"Good idea," said the center tree. One of his branched reached down towards her skirt when there was a loud "THWAK" sound. The branch recoiled as Scarecrow shouted.

"Put Dorothy down," Scarecrow said as he pitched another rock at the trees, "Right now!" He threw another rock, making sure to stay clear of the girl he was protecting.

The next rock struck the middle tree right between its eyes and the branch around Dorothy's arm let her go, dropping her to the ground.

"Oof," she exhaled as she landed on her ass. She quickly scrambled to her feet and ran to the path, her breasts bouncing with each step. She joined Scarecrow and Toto, and the three of them hurried away down the path as they dodged branches and apples being lobbed at them. They stopped running when they could no longer here the shouts of the three apple trees and tried to catch their breath.

"Oh, Thank you, Scarecrow," Dorothy said as she wrapped her arms around the straw man. "Thank you for saving me from those horrible trees! I thought..." Dorothy stopped talking, squeezed Scarecrow even tighter and then planted a kiss on his cloth cheek. "Oh, how can I ever thank you?"

The feeling of Dorothy's huge breasts squashed against him was causing his wooden cock to press out against his pants and into her hip. "Oh, I'm thinking of something you could do right now..."

The curvy brunette smiled as she pressed her hip harder against the bulge in his pants. "And what would that be, my hero?"

"I was thinking that my woody could really use a good spit and polish."

She smiled widely. "Anything you want." Dorothy slowly dropped to her knees, letting her e-cups drag down his chest and legs as she did so. She unzipped the front of the straw man's pants and released his wooden cock, gripping it with her small hand. As she stroked its length, she looked up to Scarecrow with a sexy grin.

"Oh yeah," he moaned as she pulled on his cock. "Put it in your mouth, Dorothy."

Dorothy leaned towards the cock and opened her mouth, not knowing what to expect. The wood was polished as smooth as silk and had no real taste to it. She took about half the length in her mouth and ran her tongue around it, making sure to tickle the head with the tip of her tongue. She began bobbing her head, using lots of spit to lube up his cock.

Scarecrow placed his hands on the sides of her head, running his fingers through her smooth soft wavy brown hair.

Dorothy kept half the cock in her mouth as she pumped the remaining length with her hand. She wanted to try deep throating the cock, but the hard wood wouldn't bend at all, making it near impossible to take much more into her mouth. The moans of the straw man were turning her on, and Dorothy played with her nipple for a bit before she slid her fingers down to her pussy. She moaned around the cock in her mouth as her fingers dipped into her honey pot, probing her hot wet hole. The wet sounds of her mouth on the cock blended with the wet sucking of her pussy on her fingers. She was really getting into it, playing with her clit as she tried to take more of his cock in her mouth. She was pushing three fingers into her pussy when she decided that she was going to need something more to fill her. She pulled the cock from her mouth, leaving a string of spit connecting her lips to the head of the cock.

"Scarecrow, I want you to fuck me," she said as she leaned back on the path. She pulled her skirt up to expose her shaven pussy. "Please?"

Scarecrow eagerly dropped to his knees, and pointed his wooden know towards Dorothy's dripping wet hole. He pressed forwards and watched her tight pussy lips wrap around the head of his cock and then slide over the rest of his cock.

"Oh yess," Dorothy said through her clenched teeth. "Give me that cock, Scarecrow."

Scarecrow began slowly pumping her pussy and leaned forwards. He watched her two mountainous breasts begin to jiggle with each thrust and he pressed his painted on lips against one of her nipples.

The cloth of the straw man's face felt rough against her hard nipple, but she enjoyed the new texture. She pulled his face down against her chest and then wrapped her legs around his waist. "Ooh ooh ooh," she softly said, "go faster..." She knew that Scarecrow wouldn't cum too soon because he couldn't cum at all, so he could really pound away at her and not lose it. She felt the cock plowing her pussy begin to pick up the pace and leaned her head back. "Oh yeah! Just like that," she moaned as he hit a rapid pace.

Scarecrow was pumping his hips as fast as he could, driving the full length of his cock into her. He leaned back again to watch as her massive breasts were now shaking wildly back and forth. "Oh god," he groaned loudly. "I love your pussy, Dorothy!"

Dorothy herself was now quickly approaching her orgasm. Her arms reached up around Scarecrow and she grabbed him with her fingernails as the pressure increased in her pussy. "Ugh, Ugh, Ugh... Keep going..."

Scarecrow kept his pace, pounding away and reached up to her huge jumping with one gloved hand. He grasped a nipple between his fingers and tweaked it.

The extra stimulation was enough to push Dorothy over the edge. "Ugh-- here... I... come!" Her eyes shut tight and her body spasmed as an orgasm wracked her body. She gripped the straw man tighter as her pussy gushed girl cum all over his cock, soaking the front of his pants. Dorothy's body finally relaxed and she let her head and arms drop to the ground. Breathing heavily, she looked up to Scarecrow, who was still lying on top of her, his hard cock deep inside of her. "Daaaamn! You fuck like a machine, Scarecrow!"

Scarecrow looked down at her with his permanent smile as he played with her juicy tit. "Thanks, I think..." He shifted his hips, rotating his cock inside of Dorothy, making her ‘mmmmmmmmmm'. "Do you really think that the wizard could give me a real cock?"

"I don't know. You know as much about him as I do, and that isn't much. I hope so."

The two travelers laid together on the path for several minutes, enjoying the feel of each other's bodies, until Toto walked up to Dorothy's face and licked her cheek.

"Yes, Toto, I suppose that it is time that we got going again."

Hearing this, Scarecrow removed his cock from her cunt and stood up, looking at the soaked patch of his pants. "I'm going to have to let this dry out, or I'm going to mildew," he said gesturing to his wooden cock and the damp straw around it.

Dorothy climbed to her feet and examined her dress. She wiped off the dirt on her back from their fuck and then saw that she was missing a few buttons from her dress top. "Dammit, what am I going to do about this? I can't go to see the Wizard with my tits hanging out all over!"

"I'm sure he wouldn't mind," Scarecrow said and then saw the annoyed look he got from Dorothy. "But I do have a safety pin around here somewhere..." He patted himself down until he found a pin and helped Dorothy fasten her dress.

"Thank you," Dorothy said as his gloved hand brushed her nipple. She picked up her basket and Toto. "Now let's see if we can't get out of this forest before it gets too dark..."

To be continued...Dorothy Does Oz

by Maguppy Puppy

05. Into the Deep Woods

Dorothy, Toto, and Scarecrow decided to follow the road that curved south, although none of the group knew where either path led. The cornfields seemed to stretch on for as far as they could see, so one path seemed just as good as the other. As they followed the yellow brick road, Dorothy told the straw man her story and how she had come to Oz. They were able to walk for over an hour before the sun had set too far and the path grew dark.

"I suppose that we're just going to have to sleep by the side of the road, Scarecrow," Dorothy said as she set Toto down on the ground. "It's been a looong day, and I'm going to sleep like a rock, even if it's on the side of the road." Dorothy yawned and stretched, and the Scarecrow enjoyed the view of her tight dress straining against her ample breasts. She sat down on the grassy shoulder of the path and pulled out the cloth from her picnic basket. "I think that both of us can use this as a pillow..."


"You can have it," Scarecrow said. "You forget that I don't need to sleep. In fact, I don't have eyelids, so I don't think I could sleep if I wanted to. You just catch some z's and I'll stand watch, make sure that nobody causes us any trouble."

"Sounds good to me. I'll see you in the morning." Dorothy curled up, laid her head down on the cloth and closed her eyes. Moments later her breathing slowed as she dozed off. Toto pushed his way between her arms and leaned against her chest before he began lightly snoring next to her.

Scarecrow paced the path for half an hour before getting bored and sitting down beside the pair. Sure that the girl was sleeping, Scarecrow lifted up the edge of her dress, allowing himself a long view of her naked ass. He slid his hand under her dress and touched her right cheek, causing Dorothy to reflexively kick back and knock Scarecrow over into the corn. He got up and was relieved to see that she was still sound asleep. Then he noticed the little dog staring at him, his ears flat to his head. Scarecrow decided it would be best to resume pacing the path for the rest of the night.

***********************************

Dorothy woke up the next day, gave Toto and herself breakfast and then the three began walking again. It wasn't long before they could see something on the horizon, above the tops of the corn stalks. They couldn't tell what it was, but they knew that it wasn't more corn and that was what was important. The farther they walked, the closer the darkness on the horizon got and soon they could make out the forest at the end of the field. They began picking up their walking pace as they neared the trees.

"I can't wait to get past these fields," Scarecrow said.

"I would think so," Dorothy replied. "You've never been outside of them before. I've only been in them for a day and I'm already tired of the same old scenery."

Toto let out a bark in agreement as he raced along side of them.

As soon as they passed into the shadows of the trees, Dorothy could feel the temperature drop. "Brrrr, it sure was a lot warmer in the sunlight. I hope that this forest doesn't go on as long as the fields did." Looking down the path, it was trees as far as she could see, but there was some thing else by the side of the road. "Look! Apples!" Dorothy picked up one of the apples from the ground and then spotted the trees that they had fallen from. "I'm going to grab a few of these, Scarecrow. I don't know how long it will be before we're out of these woods, and it can't hurt to have more food with us." She walked off of the path, leaving Toto and Scarecrow behind. There were several branches low enough for the stripper to reach, but she still had to stretch to reach them. She grabbed one red, round apple and pulled it off with a snap.

"Ow!"

"What did you say, Scarecrow," Dorothy asked as she looked back to the road.

"I didn't say anything. Maybe it was an animal."

Dorothy glanced around but didn't see any animals around them besides Toto. She reached back up for another apple. As her her fingers touched the apple, the voice spoke again.

"That's it," the voice said. Suddenly, one of the tree's branches swept out and grabbed her outstretched arm and lifted her off of the ground. "I'm tired of people always grabbin' my apples when ever they like." The branch twisted around until Dorothy was facing the tree. Before her eyes, a face formed in the bark with two eyes and a mouth. "There's plenty of apples on the ground but noooo... They have to yank ‘em right off my branches!"

Dorothy didn't know what to say. This was definitely a new situation to her. "I'm sorry," she began, "I didn't think that you'd mind..."

"Hmmph," the tree grunted. "Didn't think I'd mind? How do you think I'd feel about somebody yanking a apple off a me? How would ya like it if a yanked of one of yer apples?" A finger like stem reached out and poked one of Dorothy's round boobs as the tree said this.

Another voice came from the tree to the right. "I don't think she's got any apples under there... Looks more like a couple melons to me, huh huh."

"Why don't we check," said another tree.

Back on the path, Toto began barking furiously. Scarecrow knew he had to do something and rushed at the tree holding Dorothy only to be knocked back to the bricks by a large branch.

The middle tree slid a branch onto the neckline of Dorothy's dress and pulled it open letting her large breasts tumble free. The cold air of the forest had made her pink nipples very erect.

"Hey!" Dorothy shouted as she tried to kick out at the tree. She couldn't reach with her feet, but she slapped a branch away with her free hand as it poked her right breast. "I'll give your fucking apples back! Just put me down."

"Too late for that," said one tree.

"Yeah," said another. "Too late for that, huh huh. Why don't we see if she's keepin' a peach under there, too?"

"Good idea," said the center tree. One of his branched reached down towards her skirt when there was a loud "THWAK" sound. The branch recoiled as Scarecrow shouted.

"Put Dorothy down," Scarecrow said as he pitched another rock at the trees, "Right now!" He threw another rock, making sure to stay clear of the girl he was protecting.

The next rock struck the middle tree right between its eyes and the branch around Dorothy's arm let her go, dropping her to the ground.

"Oof," she exhaled as she landed on her ass. She quickly scrambled to her feet and ran to the path, her breasts bouncing with each step. She joined Scarecrow and Toto, and the three of them hurried away down the path as they dodged branches and apples being lobbed at them. They stopped running when they could no longer here the shouts of the three apple trees and tried to catch their breath.

12