Girly Scout

by T.S.Severe

Caution: This Erotica Sex Story contains strong sexual content, including Reluctant, TransGender, Humiliation, First, .

Desc: Erotica Sex Story: It's an old cliche, but that's why...It works! When Timmy ends up with the wrong suitcase at Scout Camp, he has no choice but to wear his sister's clothes. As you can imagine, the other boys want to give her a "hard time"...I mean, give him a hard time. Silly boys.

"Where's my bag, Mr. Cartwright?" I looked at our Scout Master and he looked at me. The other eight boys all had their stuff, but I was still waiting.

"Isn't that it?" He pointed at a big blue suitcase, the only thing left in the back of the van.

"A suitcase?" I shook my head.

"Who would bring a suitcase on a camping trip?" Hugo laughed and he a was a big, pudgy boy who gave everybody Charlie horses all the time.

"It says Thompson on it." Mr. Cartwright was hauling it out. "I'm pretty sure this is the one your mom gave me, Timmy."

"It says R. Thompson," I said kinda dumbly. "That's Rita's suitcase!"

"Your sister?" Goofy looking Todd grinned at the other guys and they all grinned back. "She's hot!"

"Shut-up," I frowned.

"Settle down," Mr. Cartwright frowned at the bunch of us cause the other guys were making a lot of noise. "Well, Timmy, just grab it. You guys gotta get your tents up before it gets dark. Let's go!"

"I can't believe you brought a suitcase! What a dope!" Billy was laughing at me and he was the oldest Boy Scout in our little troop, almost eighteen and an Eagle Scout to boot.

"I didn't bring it!" I protested, trying to help put up the tent, but I wasn't ever much good with that kind of stuff anyway.

"Then how did it get here?" Larry grinned at me. He was sixteen, a year older than me, and one of the guys who loved my sister. They all did really, because Rita was pretty hot. I loved her too, but we're twins, so it's okay, sorta.

"You think your sister got your stuff?" Billy wondered and I hadn't thought of that.

"I don't know." I swallowed hard, because mostly I figured my stuff would be in the suitcase, but Rita was a Girl Scout and her Jamboree was this week, and so she'd been leaving this morning in Mrs. Evenston's van and it was a white one too, just like Mr. Cartwright's and if...

"Your sister would be so hot in a Boy Scout uniform!" Larry giggled and Billy punched him in the arm.

"Don't be a fag!" Billy said.

"Ow!" Larry frowned. "What? She would be hot."

I ignored them mostly, and they were doing a good job with our tent anyway. I opened the suitcase after crossing my fingers four times, you know, all of them. I said a prayer and made vague promises to God about being good, the way people do. And I opened that suitcase.

"Oh." I stared at my sister's stuff. Like all her stuff, it looked like.

"Are those your sister's panties?" Larry asked, his eyes wide and his mouth open.

"Shut-up." I closed the suitcase quickly and then it started to rain.

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"Sorry, Timmy," Mr. Cartwright shrugged. "I tried, but we're two hundred miles from anywhere. None of the other boys have clothes you can wear, not for all week."

"But there's eight of them!" I stared at the man, wrapped in my sister's big pink towel cause my boy clothes were seriously soaked.

I was pretty sure that he coulda got some clothes for me if Mr. Cartwright had really tried. I mean a shirt here, some pants there ... How hard could it be? It was a conspiracy, I figured. All those other guys picking on me again, just because I wasn't good at football and I didn't know how to put up a tent real good. Some of them thought I was a fag anyway, I knew that, just because I was smaller and thinner than most boys my age. That and my hair was long, but lots of guys had long hair. So what?

Probably Mr. Cartwright hadn't tried at all, because I knew he didn't really want me in his Boy Scout troop anyway. Oh, he was nice to my face and he treated me okay, but I knew he thought I was kinda hopeless so far as being a Boy Scout went. Now he was telling me I had to wear my sister's clothes cause...

"Everybody has to be in uniform anyway, Timmy," he smiled. "You know that. You're just lucky you and your sister are about the same size."

"I can't wear her uniform!" I blinked at him, but Mr. Cartwright was serious.

"You have to," he shrugged. "It's the rules! You can't go on an Expedition without a uniform and ... Well, that's the only uniform you have."

"But it's a girl's uniform!" I protested. "It's got a skirt and blouse and one of those things that goes over the shoulders and a funny hat! It's stupid!"

"Now, now." He gave me a stern look. "Don't be talking bad about the Girl Scouts! They work just as hard as we do and they look pretty darn good doing it!"

"What?" I shook my head cause he wasn't making any sense.

"So when you wear that uniform, I expect you to look good too! I'm sure your sister is very proud to wear your uniform, even though the other girls will be teasing her a little."

"But..." Nobody ever teased my sister about anything.

"So if she can do it, you can do it," Mr. Cartwright decided. "This is your chance to show the troop what your made of, Timmy! So here's what we're going to do..."

That afternoon, while the rest of the boys finished setting up the camp and prepared some dinner, and generally kept busy having fun in the middle of the woods in the middle of nowhere, Mr. Cartwright was teaching me the finer points of looking like a Girl Scout and I wondered how he happened to know so much about it.

I cried, a little. I complained and whined and pouted and got mad, sad, and bad ... But in the end, Mr. Cartwright won out, as he had to, being the Scout Master and the only adult for a hundred miles in any direction you'd care to look.

"There we go, okay ... Let me see..." Mr. Cartwright was smiling and happy when we were finished.

"Did you have to shave me all over?" I frowned, cause it was weird having the man shave the little bit of peach fuzz I had growing around my dick, you know?

"Oh yes!" Mr. Cartwright nodded. "That's the most important part!"

"I thought you said making my nipples puffy was the most important part!" I blinked at him, thinking maybe Mr. Cartwright didn't know what he was talking about after all. He'd pinched my nipples hard too!

"It is," he chuckled. "You have to realize, Timmy ... Errr, you know, we can't really call you Timmy anymore, can we?"

"What?" I stared at him.

I was standing there in my sister's pink panties, knee high white socks, kind of an olive skirt with pleats that didn't even come halfway down to my knees, and a blouse that was tucked into the skirt and kind of loose, since my sister had breasts and I didn't. My blonde hair was brushed and loose around my collar, my lips painted red, thanks to all the make-up my sister had packed. I even had a little eye shadow, because Mr. Cartwright said it made the blue in my eyes 'pop' ... Whatever that means.

I was wearing black heels too! Why would my sister bring her high heel shoes camping? I mean, they weren't really high heels, only like one inch or something, but still ... She was so retarded sometimes! I wanted to wear my old shoes, but they were soaked and full of mud and Mr. Cartwright said no Girl Scout in her right mind would wear my ugly shoes.

"Well, you sure don't look like a Timmy anymore. Do you?" Mr. Cartwright said gently.

In fact his whole attitude had changed, kinda. Like the more of my sister's clothes I put on, the more Mr. Cartwright was nice to me. I kinda didn't mind that so much. I just wasn't sure why exactly, except probably he was feeling sorry for me, now that he saw me looking like a girl. And I did too, so far as I could tell in my sister's little hand mirror. I looked like her, actually. I mean, I looked a lot like Rita, except her hair was a bit longer and she had real tits.

"I guess not," I frowned some more.

"How about Tammy?" Mr. Cartwright smiled at me and he was standing in front of me, kinda close and squeezing my shoulders.

"Tammy?" I looked up at him.

"Uh-huh," he licked his lips. "That's a nice name, don't you think? It sounds just like your old name."

"Why can't I just be Timmy?" I asked and I was shaking, because I was scared about doing this. Nervous too and those feelings kind of came and went. Now they were back.

"Well, I just think it would be easier, you know." Mr. Cartwright stroked my hair, cause a little bit had gotten in my eyes. "So we'll call you Tammy, alright?"

"I guess," I made a face and looked down.

"You're very pretty, Tammy," Mr. Cartwright said softly and I looked up at him sharply because I'd been called pretty before and it was always like an insult.

"No, I'm not," I told him.

"Yes, you are." He smiled at me, a real one, not a teasing one. "I think you're the prettiest Girl Scout I ever saw, Tammy."

"Really?" I blinked at that and wondered if that wasn't pretty insulting too, even if he meant it like a compliment, which I think he did.

"A beautiful girl, yes you are," Mr. Cartwright swallowed hard and cleared his throat. "Okay, um, well ... Let's go meet the boys, huh?"

"Heh!" I laughed. "I already know the boys, Mr. Cartwright."

"Yeah, but they don't know you, Tammy." Mr. Cartwright's hand slid off my shoulder and down my back, all the way down to my butt and he gave me a little push, except it felt like a squeeze mostly and I frowned over my shoulder at him.

"They're gonna laugh," I decided. "I can't!"

"Yes you can." Mr. Cartwright rubbed my butt like that would make me feel better or something. "Just keep your voice like that too."

"Like what?" I asked and I talked normal, but I had a high voice anyway. I was in the choir at school, you know.

"Like that," Mr. Cartwright sighed. "You're perfect."

.... There is more of this story ...

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Story tagged with:
Reluctant / TransGender / Humiliation / First /