Chuckwagon Cookie

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows?

Anyways as my regular readers are aware, I enjoy writing about characters with fluid sexuality.

The old American west has an image of hardy settlers, tough as nails cowboys, and Native Americans fighting for their land. However there was another side to the old west that gets overlooked; it was gayer out there and there were more people of color than you know. This story recounts a female cross-dresser's experiences on a cattle drive sometime in the 1880s.

As you read this story please keep in mind that some of the characters believe my heroine is a gay male.

~~

Her name was Rosetta, but everyone called her 'Rocky'. She had a smooth pleasant looking face, with brown eyes and thick full lips.

She was five-foot-seven and weighed a hundred and forty pounds with broad shoulders and a flat chest for a woman. On the other hand she had an ample round bottom that she kept hidden in loose fitting trousers.

She grew up in a shack on the Circle-J ranch where her family worked. Her part Native American mother was a housekeeper for the rich ranch owner, and her father, a former slave worked as a horse wrangler for him.

Rocky grew up wanting to be a cowboy just like him. When she was fourteen she pestered him until he allowed her to work with him alongside the other s. She wore men's clothes and due to her wide jaw line when she tucked her long black hair under a floppy hat her face took on a masculine appearance.

~~

Four years later.

"Poppa, I'm eighteen now and I'm going on the next Cattle drive that's carrying cattle from the Circle-J to Dodge City," insisted Rocky.

Her father closed his eyes and exhaled in exasperation. "Rocky honey, that kind of lifestyle ain't proper for a woman in this day and time."

"Poppa, it's the 1880s for goodness sake," she countered. "I have the right to live a life of freedom and have adventures same as a boy does. Next you're gonna tell me to stop wearing jeans and dress like a lady."

Her father squinted at her with a frown on his face. "You do such a good job of hiding your female gifts, I've heard some of the s call you a man-woman," he said with sadness in his voice.

"Hm, they're probably the ones I won't let dip their wick in my tinder box or face-make me," responded Rocky dismissively.

After pausing for a moment she added, "Poppa I like men plenty, but if I was queer I don't think it would be a bad thing."

"Rocky that's too much information," said her father as he raised his hand to signal her to stop talking, then he exhaled and his shoulders slumped.

At that point she knew he'd rather be talking about anything other than her sex life. "Poppa I'll be fine, and if there's any trouble along the way there's a couple older s from the Circle-J who'll be there for me," she added.

Her father then asked her if the trail boss knew she was a girl. She said no and that she'd warned the cowhands from the Circle-J not to tell him. When her father tried to muster another protest she pointed out that Cattle drive crews usually had a few greenhorns and she could ride and rope as good as any of them. Then she made him promise that he wouldn't tell the trail boss about her either.

Her father gave in that day and stopped trying to talk her out of becoming a cowboy; instead he went to his old friend the chuckwagon cookie who'd be on the drive and asked him to take her on as his assistant. The old cookie had known Rocky since she was a kid, and thought of her as his niece, so he agreed to take her under his wings and to show her the ropes.

Her father then went to the trail boss whose name was Charlie, and told him that Rocky was green and that he was worried about her getting hurt. Charlie already thought that Rocky was gay, and he was kinda sweet on her, so he told her father that he'd put her at the rear of the herd where it was less dangerous.

On the day the cattle drive was to start her Uncle Cookie asked her to work as his assistant. Rocky suspected that her father had put him up to it so she turned down his invitation.

Once the cattle drive started Charlie kept his promise to her father by sending her to ride in relative safety at the back of the herd with the drag riders. She then spent the day nudging the stubborn, lazy, and disinterested cattle to get them to keep up with the rest of the herd. It was hot, dirty and hard work, and then at night she had to wallow out a spot to place her bed roll then sleep on the ground.

She might have looked like a man dressed the way she was, but she was a woman and sleeping on the hard ground was uncomfortable for her soft body. After the second day of eating dust stirred up by the cattle she decided that being a cowboy on a cattle drive was dirtier work than she was cut out for. On the third day of the drive she went to the front of the herd and rode beside the trail boss.

He looked to his right at her; she was dirty and her hair was a mess, but he thought that she looked like a twink and that made his cock get hard.

She held her tongue for a few minutes because she wanted to get control of her emotions. Not only was she angry about being assigned to trail the herd, she was also trying to control the attraction she felt for him. It was the first time she'd been attracted to a man.

Charlie was the prototypical cowboy of the era; he was wiry, strong, and rugged looking with a full beard, dark skin and bowed legs that made Rocky weak in the knees.

They rode along quietly until she got up her nerve. "Charlie, some of them cattle at the back of the herd are ornery," she said while looking straight ahead.

"Yep," he responded stoically.

After a long moment she glared at him and said, "You knew how dirty that job was, why didn't you let me work with the horse wrangler like you'd promised?"

"Thought you wanted to be a cowhand," he reminded her.

"You ass," she huffed. "You lied to me."

Normally those would have been fighting words, but rather than getting into fisticuffs Charlie wanted to take the diminutive cowhand into his arms and kiss him deeply.

His silence enraged Rocky, but if she was honest his strong silent demeanor was also arousing. Finally she blurted out, "Uncle Cookie said I could work for him, that's what I want to do."

"Suits me," agreed Charlie as he stared straight ahead lest he might take Rocky right then and there.

Later that day he watered the cattle in a stream that formed a small pond before continuing on it's way. Once the herd was settled Rocky sneaked off and took a bath, then she went to her Uncle Cookie with a chastened look on her face and accepted his invitation to work with him.

She then helped him clean up after the meal that night. Afterwards the fatherly old cookie insisted that she not sleep on the ground any longer like she was one of the men. She put up a token protest, but he wouldn't take no for an answer so she agreed to allow a little bit of her femininity to come out. She climbed into the big chuckwagon, washed-up in a pretty water basin, did her business in a chamber pot, then got into a comfy bed.

~~

Now that she was working for her Uncle Cookie, each day felt like more of an adventure. She was free to ride on the wagon with him, or go off and chase a stray steer if she wanted, or scout ahead for a good place to make camp as long as she didn't get out of his sight.

Around the same time another cowhand by the name of Bodine started paying attention to her. In the beginning she ignored him, but once she realized that Charlie was paying attention to them she decided to respond. When Bodine finally approached her one night after supper, she glanced at Charlie out of the corner of her eye, then smiled at Bodine.

Up until that time Charlie had done a good job of keeping his interest in Rocky hidden, but he knew Bodine was a cockhound and the thought of him touching Rocky was enraging. When he finally had all he could take of watching them exchanging glances he got up from his seat near the campfire and went to see about the horses.

Rocky wanted to go after him, but she couldn't afford to expose her true identity, so she kept to doing her chores. Her train of thought was broken when Bodine brought his empty plate back to her and said, "The beans shore taste better now that you're helping Cookie fix them."

She deflected his praise and gave all the credit to her Uncle Cookie. He then asked her about herself. She responded, "I'm eighteen," then hesitated before adding, "I'm a Ranch Hand on the Circle-J. This is my first cattle drive."

Bodine responded saying, "I'm twenty and this is the third herd I've help drive to Dodge City."

They then talked for a while longer exchanging innocent information about themselves until Bodine asked the question he was really interested in having answered. "Rocky are you cherry?" he asked after looking around to make sure nobody would hear him.

Rocky didn't answer for a second; she might have looked like a man but she was a woman and she wasn't used to being asked that kind of thing, especially by a man. The answer was that she'd never done anything with anybody, but she'd watched the stallions mount the mares, and the bulls mount the heifers plenty times. Watching their coupling inflamed her desire for a man, and she oftentimes played with her clit to release sexual tension afterwards.

When she found her voice she responded saying, "I ain't been with nobody before."

Her answer gave Bodine more confidence because he had a handful of experiences under his belt. He boldly asked, "Do you fancy a filly, or would you prefer to have a fella ride below the crupper?"

Rocky squinted then tilted her head to the side and asked, "What in blazes are you talkin bout?"

"Dang-it man, don't you know anything bout the birds and the bees?" he answered with a question of his own. "I want to corn-hole you."

Rocky's body jerked reflexively when it dawned on her that he wanted to put his pecker in her bunghole. She said, "Eww," and grimaced. Then she asked, "Why would you want to stick me there when girls have a perfectly good place that was made for your tallywacker?"

"Well, ain't no girls around," he informed her. "Besides, your corn-hole serves the same purpose."

She thought about what he'd said then she asked him a question, "Do all cowboys like to do it back there?"

"Not all," he replied. "But plenty of em do it. I even heard tell of some fellas who put a man's spouter in their mouth. Just make sure you keep your teeth off of it."

Rocky pressed her lips together while shaking her head no, but the notion of being mounted like a mare or licking a man's dangler caused her core to tighten and her mouth to water, but she didn't want to do it with him.

"There ain't no way I would ever do either one of those things," she lied when she responded.

That was the last time she talked to him about sex, and a few days later she noticed that he was paying attention to another cowhand named Jethro.

~~

As fate would have it she was emptying her chamber pot a few days later when she saw Jethro using the community tree. His pee was flowing like a cow peeing on a flat rock and he was hung like one of the bulls they were taking to market.

Now that she was aware that there were cowboys on the drive who played with each other, she decided to keep an eye on Bodine and Jethro. A few days later her hunch paid off when she followed them into the bushes while the other cowhands were sleeping by the campfire a short distance away.

She watched as Jethro pulled his pants down, bent over and then guided Bodine's dick into his asshole. As soon as Bodine's manhood slid between Jethro's asscheeks he went to hunching. Bodine pumped his peter into the soft smooth inner walls inside Jethro's backdoor for only a minute or two and he was already close to cuming.

Rocky couldn't believe what was happening; Bodine was riding Jethro like he was a bronco, and Jethro's cock was so big until Rocky wondered if it would come out of her throat if he stuck it in her from behind. It's shaft was so thick until she was sure her inner pussylips would cling to it as it was going in and out of her.

After another moment of humping, Bodine emptied his nuts into Jethro's guts. As soon as he was done he kneeled in front of Jethro and took his massive cock into his hand. After admiring it for a moment he started performing fellatio on him. If looked to Rocky as if Bodine was enjoying giving Jethro some mouth loving as much as Jethro was enjoying receiving it.

After the deed was done Jethro had a goofy grin on his face when he said, "Dog-gone-it Bodine, that shore felt good."

Bodine laughed softly as he patted Jethro on the ass then said, "It sure did."

~~

The next morning Rocky was up with the cookie making breakfast hours before the crack of dawn, as she did every day. She was learning the ropes from one of the best cookies around. As a cook he could even make dried beans and salt meat taste good.

Cooking was only one of his many jobs; he was also teaching Rocky how to give the trail hands free haircuts that were as good or better than the ones they paid for from a barber. However she was slightly intimidated about mixing herbs and dispensing potions and salves that eased the cowpoke's pains and healed their wounds.

~~

As soon as Rocky saw the first rays of sunlight she started making all kinds of racket by hitting a pan with a spoon. The tired cowhands began pulling themselves out of their all too short sleep. Their first stop was the community tree, or the latrine, then they made a beeline to the strong black coffee.

She served them bacon, potatoes, and flapjacks with maple syrup. A couple of the older trail hands from the circle-j smirked at her while she served them. One of the men wisecracked about the night before, "I saw you go in the bushes over yonder last night; heard you making a lot of racket too. Thought I was gon have to come see about you."

The scruffy older man in line behind him that was also from the Circle-J snickered. Rocky glared at both of them; instead of telling them what had actually happened she said, "I appreciate that, but I was being well seen about." She then raised an eyebrow before saying, "Keep the line moving, let the hard working men behind you get their grub."

As soon as she and the cookie got the dozen men on the drive fed they put away the leftover potatoes and flapjacks, then they started cleaning the dishes. She was humming contentedly while doing her work.

~~

A few days later the cattle drive had made it to the edge of Texas; off in the distance, and unbeknownst to anyone involved in the cattle drive, there was a group of Native Americans watching and waiting for them to enter their territory.

By noontime that day the cattle had traveled about eight miles when they stopped to eat and rest near a stream. Rocky and her uncle cookie had already reached the spot and setup a lunch of leftover potatoes, flapjacks and thick black coffee.

Most of the crew was gathered around the chuckwagon when they heard a shout from one of the wranglers who was still with the herd. When they looked in his direction they saw a chief and a group of warriors carrying a white flag. The herd was on the edge of the native's territory, so Charlie knew what they wanted. He could have done business with them, but he figured that Rocky being part native could make a better deal, so he stood up and beckoned for her to come stand beside him.

She glared at him; she was still pissed; not only had he made her ride at the rear of the heard instead of letting her be a wrangler like he'd promised, he hadn't paid attention to her and for that she hated him. When Charlie looked at her expectantly after looking at the chief, she spoke in the native's language saying, "Have you eaten?"

The chief looked at his braves stoically, then they climbed down from their mounts. A fabulous looking brave who wore paint on his eyelids and had feathers in his hair introduced the chief. "This is Chief Hung-Like-Donkey. Chief of the Two-Spirit tribe of the Mohican Nation," he said.

The chief studied Rocky for a moment and then said, "You are Mohawk?"

Rocky grinned happily and said, "Yes, I'm one quarter Mohawk on my mother's side."

The chief then nodded as he looked her up and down, before accepting the plate of flapjacks Rocky offered him. Once the chief dug in his braves joined in and they ate enthusiastically until they got their fill.

While everyone else was eating the chief had been talking animatedly with Rocky one on one. Seeing that he was in a good mood Charlie decided to begin the negotiating. The chief looked at Rocky then looked at him, and then said, "I no longer want your money in return for allowing you to cross our land." He then looked at Rocky with lust in his eyes and added, "I want Rocky-Two-Spirits to come visit my village."

The chief called her Two-Spirits because he also thought she was a twink.

When Charlie said no, Rocky looked at him defiantly then smiled big at the chief. She got a bit of satisfaction when she thought she saw a hint of jealousy in the look on Charlie's face when she said, "Don't worry Charlie, I'll be back in plenty time to help cookie cook supper." Then she pointed to the northwest and added, "Their village is just beyond the rise.

"He'll have his braves bring me back to the wagon in a couple hours."

Charlie started to protest, but the important brave cleared his throat. At that point he realized the chief wasn't asking, he was telling them what he wanted.

~~

About an hour later Rocky pulled back the flap and walked into the chief's sweet smelling tepee with a plate full of flapjacks. He was sitting on his bed Indian style as naked as the day he was born, and smoking something in a pipe. He'd been getting his head right while Rocky cooked for him. Her eyes almost popped out of her head when she saw him. She quickly pulled herself together and greeted him with a smile, and teasingly said, "Hey there chief, how you doin?" It was true that Rocky had come back to the chief's village to aggravate Charlie, but she also considered it an honor to cook for him.

The chief blew a puff of smoke into the air, then shifted to a prone position where his big hard donkey dick was on full display. "Have you eaten?" he asked suggestively.

At that point she bit her bottom lip seductively as she placed the food in front of him. She then knelt and they ate together.

~~

When she got back to the chuckwagon her Uncle Cookie made a fuss and asked her several times if she was alright. Once she'd convinced him that she'd been treated properly they went about preparing the meal, and when the cow hands settled the herd down for the evening she and the cookie had supper waiting for them.

An hour or so later the men were fed and Rocky and Uncle Cookie were in the daily process of wrapping up the meal they'd just served and preparing for the next one.

It'd been obvious to Charlie that the chief as well as the brave who spoke on his behalf were both gay, and he'd been tormented all afternoon by the thought of Rocky servicing them while she was gone. As a result his nuts were swollen and his hard cock was leaking pre-cum into his draws. He finally gave into his need to reach out to her after the men began to settled down for the night. She was checking the sourdough starter when he came up behind her. Rocky, I-I-I owe you a big thank you today," he stammered. "The tribe charged me their lowest price for letting us cross their territory."

Rocky looked over her shoulder at him and said, "What?" She then remembered that the chief had said that he wanted her to come to his village instead of receiving money, but it wasn't her concern that he changed his mind so she shrugged and said ok.