by T.S.Severe

Rachael Ross 1982 - 2012

Romantic Story: Ashley is the new girl in town. Armed with a pretty face, her Triumph motorbike, and a lot of personality, she's determined to meet the boy of her dreams, even if it means breaking his heart.

Tags: Romantic   TransGender  

"You're the new girl, huh?" The boy was bigger than me, and probably a year or two older. "What's your name?"

"Ashley," I replied, sitting on my motorcycle and drinking a Mountain Dew.

We were in the old suburbs. There wasn't much else around except the school, a couple churches maybe, and a Seven-Eleven, so that's where I'd gone. It sucks moving to a new city when you're sixteen, but it could be kind of fun too, depending on what you're looking for.

"You look like a guy," another boy said.

He was big like his friend and kind of cute with his sandy buzz cut, sky blue eyes, and muscles. Definitely a jock and I kind of liked him right away. The two of them were leaning against an old Challenger painted factory orange. Like a '71 maybe, one of the last real cars built in Detroit and it was in fine, fine shape.

"So?" I shrugged and took another drink from the can, pretending like I didn't care what he thought about me.

I'd dressed for riding in some old jeans, faded nearly to white with ragged cuffs around my scuffed boots. They had oil stains on the thighs and around my ass, the kind that never come out. Across my smallish tits I wore a black t-shirt, a tight one with 'Dead Kennedys' printed in white. I kept it tucked inside my pants and I had a white belt with a big yellow daisy belt buckle in front. My long brown hair was in a ponytail down my back and even without any makeup or anything I knew what I looked like.

I had a decent body and a real pretty face, and I'd always been something of a tomboy. I leaned back on my ride, not really posing, but I could have been, and stared right back at the boy.

"What's wrong with the way I look?"

"Nothing," Buzz cut said. "Most girls around here look different, that's all."

"Well, I ain't from around here," I reminded him with a grin.

"I'm Seth," the first guy said and he had black hair just over his ears and brown eyes like mine, except darker maybe. My eyes are kinda hazel mostly.

"I'm Butch," Buzz told me and I giggled so he frowned. "What?"

"Most people figure I'm butch," I said, but that joke went right over the top. "Who's car is that anyway?"

"Mine." Seth looked at it and he had a right to be proud. "You know anything about cars?"

"Not really," I said. "Too many wheels for me."

"What kinda motorcycle is that?" Butch jerked his chin. "A Harley?"

"What?" I snorted and shook my head. "Not even close, dude. It's a Triumph BST850 about as old as that Mopar. Racing bike."

"Cool," he said, smiling and nodding. "It's kinda big."

"Size matters," I shrugged. "It'll do one ten..."

"Is that all?" Seth chuckled.

" ... in third gear." I looked at him. "I drop the hammer and red line's about one seventy, one eighty maybe."

Seth frowned at me and I didn't apologize. We both knew that six pack of his might hit one forty going downhill on a windy day, but that's about all. Still a nice fuckin' car though, don't get me wrong. It would have been fun running him for pink slips, but we'd just moved in and I didn't need to make any more enemies than I was gonna have anyway. I wasn't ever looking, but somehow it seemed like trouble always found me. That's the problem with being a tomboy.

"Shit." Butch shook his head. "That's fast."

"Quick too." I grinned at him. "You wanna go for a ride?"

"Hell yeah," he agreed, casting a sidelong glance at his friend.

"We've got a football game with some buds," Seth reminded him and then looked at me. "You play? It ain't tackle or anything."

"Me?" I grinned at the idea. "Nope, I'll watch though. Come on, I'll give you a ride."

Butch didn't make me ask him twice and I think he'd started liking me back, which was nice. I'd been in town for two whole days and kind of missed my old boyfriend. We'd made promises about writing each other and calling, but I had to be realistic too. I probably wasn't ever going to see him again and the only cure for that depressing thought was to find someone else. I hated being lonely and a big, strong buzz cut would be just what the doctor ordered.

I waited while Butch got on behind me, moving slowly, cautiously like he wasn't sure what he was doing. I didn't know if he was worried about the motorcycle or me. I kicked the passenger pegs down for him and smiled over my shoulder as I cranked the engine around, firing that bad girl up with a deep throated growl and a bit of blue smoke. She was pushing fifty years though, so I'd forgive her that and reminded myself to change the rings again. Triumphs were always a pain that way, like a high maintenance girlfriend.

"Put your arms around me, scoot up. I ain't gonna bite," I told Butch. "Don't grab my tits either."

"I won't," he promised with a small laugh, wrapping his arms around my slender waist. He slid his crotch right up against my ass nice and firm with his thighs rubbing mine and I liked that a lot.

"Too bad!" I giggled and popped the clutch, screaming through the gears and leaning into the turn out of the parking lot. I just wanted to see if the boy could handle a little get up and go.

He did okay for a virgin.

"Oh fuck!" Butch shouted, squeezing my tummy with his chin on my shoulder. We were doing about ninety down County Road Seven. "Jesus!"

I pushed a little more, just to hit triple digits before slowing down to something almost reasonable. If I got a ticket, I'd be dead. A hundred ten in a forty zone? Heh! What a show off.

"You okay?" I asked and the bike wasn't very loud at all right then. She purred sweetly and gave us some good vibrations, but mostly the ride felt smooth as silk. Just the wind made talking tough.

"Yeah! It's great," he said into my ear and then gave me directions to his football game.

I figured about half the jocks in high school must have been at the field. A bunch of sixteen and seventeen year olds, a couple older boys too probably. Some girlfriends were around, sitting down together in their little clique, cheerleaders the bunch of them, I'd bet money on it. The other girls, the younger ones who just wanted football player boyfriends, walked around giggling and showing off their charms like they'd learned it from MTV.

Me being me, I drove right onto the grass and across the fifty yard line to where all the guys were hanging out, waiting to start the game. I liked the attention and besides, I had Butch behind me and I was just dropping him off.

"You owe me now." I smiled at him, removing my shades as Butch got off the bike.

"Is that right?" He grinned back at me. "For gas?"

"For not abusing you," I said with a giggle. "Take me out later."

"I don't have a car," he said, glancing self-consciously over his shoulder.

There were a dozen guys looking at us. Butch's friends were obviously wondering who I was and what we were talking about. The girlfriends too, pointedly staring and whispering from the aluminum bleachers. I ignored all them.

"I'll pick you up, but you're taking me out," I said. "Okay?"

"Yeah," he agreed with a smile. "Are you gonna wear a dress?"

"Course I am, if it's a real date," I said. "But if all you wanna do is make out..."

"Huh?" He even blushed for me, that big strong buzz cut boy, and my heart gave a little stomp.

"Where do you live?" I asked.

"Fourth street, eight forty," Butch told me. "Look for a big blue house. It's the only one, you can't miss it."

"Cool." I grinned at him. "About seven, alright?"

"Yeah," he nodded, looking around and licking his lips.

"Hey Butch!" I called out, just as he'd started to turn away. I made him wait a second while I put my sunglasses back on. "You got a girlfriend?"

"Uh ... Sorta," he replied and a few of his buddies were smiling. I'd caught a couple words here and there as they talked about someone named Linda, which is why I'd asked.

"Dump her," I said, smiling, but serious too. "I don't share too good."

"Shit..." some guy laughed. "Who are you?"

He looked like the quarterback, the most handsome boy in school and he knew it. You know the type. That made him the leader and I met his eyes with mine as I kicked the Triumph into life.

"I'm Butch's new girlfriend," I told him with a shrug, and then took off across the grass, very much enjoying my life right about then.

"Where have you been?" Stephanie wondered. My sister sat on the floor of her bedroom, still unpacking and looking frustrated. That's why I just left everything in the boxes until I needed it.

"Sight seeing," I replied, stepping around the mess to reach her closet.

"What are you doing?"

She'd just turned sixteen and aside from being the same age, we were about the same size too. That came in pretty handy and people said we looked a lot alike, but we were different in a lot of ways. Like our taste in clothes, for example.

"I need to borrow a dress," I said, frowning as I looked through her closet. "Did you unpack all your clothes already?"

"Borrow a dress? For what?" Steph pushed herself up with a sigh. "You've got a boyfriend already?"

"Yeah!" I giggled over my shoulder at her. "It was easy."

"That's sick." She scowled and I hated that because I loved her a lot. Maybe she was only my step-sister, but Steph was my best friend in the whole world as well. My only friend sometimes.

"What?" I asked, striking a wide-eyed, innocent pose.

"You've got a boyfriend in like two days and I don't know anybody!"

"You just gotta go outside and..." I started smiling.

"And you're not even a girl!" She shook her head, leaning against the wall next to her closet. "How does that work?"

"I don't know," I shrugged, refusing to feel guilty about it. "I just said hi to him."

"Did you tell him you're a boy?" Steph asked and I rolled my eyes. "He's gonna kick your butt, Ash."

"No, he won't." I scrunched up my nose. "He's pretty sweet."

"We aren't in New York any more, in case you haven't noticed," she said. My sister crossed her arms and stared at me.


"This is like Rodeoville," she continued. "They beat people up for being different around here."

"Rodeoville?" I grinned at that. "Nah, he's cool. I mean, you can tell, you know? I'll tell him tonight."

"Mom and Dad figured you'd like snap out of it," Steph sighed. "Like moving to a new place, you know?"

"I know," I said. "There's nothing to snap out of though. I'm just me. They're used to it anyway."

"Yeah," she agreed. "But that doesn't mean they like it."

"I know." I turned around because I didn't want to talk about that stuff anymore. "Where's that blue dress at? The one with the lace and stuff."

"Right in front of you." Steph laughed, reaching past me to grab the hanger. At least she relaxed a bit; my sister could stress just fine without the joy of unpacking, believe me.

Thankfully, she couldn't ever stay unhappy for too long either. Steph would get her own boyfriend quickly enough anyway, if she wasn't too shy. She looked about as pretty as me, everybody said so, and I think it bothered her sometimes. Being compared to her brother couldn't be easy, but even Steph had to agree I was a lot better at being a girl than a boy. That wasn't completely true though. I was best at being a tomboy, kind of a girl with some boy in me, you know? It sounds silly, but it's true.

If I tried to be all boy, I was hopeless. If I tried to be all girl, it just didn't work because I wasn't. But if I was a girl with boy parts, I felt right at home in myself then. It's why I was so good at being a tomboy and like that day, on my motorcycle messing with Butch and his friends, I felt like nobody could hurt me. Like I was bulletproof, you know? I could say anything or do anything and nobody could stop me. Nobody could hurt me or beat me up or call me names. It's the best feeling in the world.

The tomboy me was the real me. Sometimes I forgot that.

"Hi Daddy!" I came downstairs for dinner wearing my sister's dress.

I had my own dresses, but none that would really fit in with Rodeoville, as Steph had called it and she was right about that. We were in the sticks compared to New York City, and we were both a little miffed about moving.

"Hey Ashley." Daddy smiled when he saw me, even though I knew he wanted a son. "Wow, look at you! All dressed up."

"Yeah." I smiled happily. "Do I look okay?"

I posed playfully for him, turning around so he could see me. I had a very slight build with narrow hips and slender shoulders. I had small breasts thanks to some pills I got from the doctors, estrogen mostly. My tits were growing though and the female hormones were great for my complexion. I kept telling Steph she should get on birth control or something since every little pimple was like the end of the world for her. She worried that people would think her a slut if she took the pill though. It was always something with her, but our parents probably would have freaked out anyway.

My brown hair was loose now, long and falling in waves around my freshly scrubbed face. I hated brown hair, it seemed totally boring and I wanted to color it raven black. I thought that would be more me, you know? I definitely wasn't a blonde or a redhead. I'd put on a little make-up, but not too much. The dress was thin, one of those cotton summer dresses that buttoned up the back with a white sash tied around my waist. It had white lace around the short sleeves, neck, and hemline. It looked nice, but kind of old fashioned, I thought. Underneath I wore one of my bras, the soft one, not the hard one, and a pair of plain white panties.

I wouldn't say I felt uncomfortable in a dress, but it didn't make me feel anymore feminine than some leather hipsters and a halter top would. Have you ever tried riding a motorcycle in a dress? Still, if I wanted a boyfriend, I'd have to look like a real girlfriend sometimes, like on the first date especially. So I wanted to look...

"Very pretty," Daddy told me and he hid his disappointment pretty well. "What's the occasion?"

"Oh, I've got a date," I told him. "I'm going to pick him up at seven."

"I ... see..." he blinked at that news. "That was quick."

"Well, he said hi and I said hi, and next thing you know..." I stuck the tip of my tongue out and giggled. "It's okay, right? You said I could go out."

"I thought maybe you and Steph would..."

"She's still unpacking." I rolled my eyes. We both knew she my sister wouldn't stop until she'd finished, probably at 3am or something.

"I bet she is," Daddy chuckled. "You'd better be careful on that bike. Don't hit a cow or something."

"I survived Manhattan, remember?" We shared a grin, but he probably had a point.

"Hey! There you are. Dinner's ready," Mom said, sticking her head out the kitchen doorway. "Ashley, get your sister ... Get her, don't yell..."

"Kay Mom," I replied, letting out the deep breath I'd taken. Steph's bedroom was right above us, I didn't see any problem with yelling.

"And why are you all dressed up?" She stared at me.

"She's got a date," Dad said. "With a boy."

"Hmmm..." Mom pursed her lips and she and dad shared a look, but I'd grown used to their concerns a long time ago. I wasn't gonna change.

Sometimes it seemed like they just expected me to wake up one day and be a full-fledged, red-blooded American boy. I'd get a haircut, wear boy clothes, and find a girlfriend to try and knock up. Heck, maybe I'd even grow a mustache and join the football team. Right! I'd started wearing Steph's clothes when I'd been six years old. By the time I turned ten, I dressed always and everywhere, even going to school as a girl. People wondered and gave my parents all kinds of suggestions, mostly bad ones, but to their credit they decided to let me be me and hope for the best.

I got seriously lucky when fate was handing out parents!

"Does this boy have a name?" Dad asked over dinner.

"His name's Butch," I said. "He's a senior, like me."

"Butch?" Steph laughed and had to cover her mouth before she made a real mess.

"Stephanie!" Mom frowned at her.

"Sorry." My sister swallowed hard and drank a little water. "You're kidding right? His name isn't really Butch, is it?"

"Yeah," I giggled. "It really is."

"What's wrong with Butch?" Mom wondered and she was like from another planet sometimes. "That's a nice name."

"I don't know," Dad said, but he was chuckling softly.

"He looks like a Butch anyway," I shrugged. "He's kind of big."

"He is?" Steph narrowed her eyes. "What's he look like?"

"I dunno. He looks like a farmboy, I guess," I told her. "Kinda hot, actually."

"Hot?" she and Mom said at the same time, but in very different ways. I decided to drink some of my own water.

"Maybe I should talk to this boy," Dad suggested and I ignored that idea. I mean, Butch didn't even know I was a boy yet, so it might have been sorta weird for both of them.

"Hey!" I looked at my sister. "He's got a friend named Seth, pretty cute. He's got an old Challenger too."

"An old who?" Steph asked and she could be pretty hopeless with anything outside home economics.

"What year?" Dad asked, being an amateur motorhead. He'd taught me a lot and liked that much about me anyway, except I didn't really apply myself to anything but my Triumph.

"A '71 it looked like," I shrugged. "Pretty stock too, you'd like it."

"What's he look like?" Steph wondered, picking at her mashed potatoes.

"It's red." I smiled at her.

"Not the car!" She rolled her eyes. "The boy!"

"Oh, Seth? He's cute. Black hair, kinda brown eyes," I said. "He's big too. Another one of those strappin' country boys!"

"Strappin!" Steph laughed and Mom frowned. Daddy gave us a hard look because Steph had just turned sixteen and unlike me, she had her cherry to worry about.

"You wanna go with me?" I asked her. "You can meet Butch, go with us to wherever we're going and maybe meet that Seth guy."

"Seth?" She pursed her lips. "Steph and Seth ... That sounds bad."

"Where are you going, by the way?" Dad wondered.

"You pick your boyfriends by how your names sound together?" I laughed at her.

"Well..." She frowned.

"Ashley?" Dad held out his hand, expecting an answer.

"I don't know," I shrugged. "There ain't anything around here anyway except the Dairy Queen."

"Well Stephanie can stay home tonight," Mom decided. My sister frowned, but she was sorta shy anyway, which was her whole problem, I thought.

"I gotta finish unpacking anyway," she sighed.

"I'll tell him about you," I promised, and then leaned close enough to whisper in her ear. "I bet he's got a big dick too!"

"Oh!" Stephanie gasped and turned like five kinds of red all at once. She looked almost comical and like I said, my little sister was a total virgin.

"What are you two whispering about?" Mom wondered and I just gave her my innocent face.

"Nothing Mom," we replied in unison and we were pretty good at that.

=-=-=-=-= =-=-=-=-= =-=-=-=-= =-=-=-=-= =-=-=-=-= =-=-=-=-=

The trick to riding a motorcycle in a dress is to make sure it has a long skirt, first of all. Second, you pull it tight around the thighs and sit on it. Third, and this is important, you ride like a bat out of hell to get where you're going before it gets so wrinkled you have to turn around and go home in shame.

There's another way though, much simpler and I generally prefer it ... Just don't care. Riding fast is still heartily recommended, however, because that way most people will wonder if they really did see your panties or not. Also, now that I'm thinking about it, the wind really feels good!

"Hi!" I said, combing my fingers through my hair and wondering why I hadn't put it in a ponytail before leaving the house.

"Hello." An older man smiled at me, an older version of Butch, big and healthy with a buzz cut all his own.

"Can Butch come out and play?" I asked him with a nervous giggle. My heart was going pitter-patter because I'm awful with parents.

"Excuse me?" The man blinked.

"Sorry, uh..." I cleared my throat. "I'm Ashley. Is Butch home?"

"Yeah, he's here," the man agreed. For a second there I thought he intended to close the door and make me wait outside.

Ever notice how everyone else's family always seems a little weird, but your own family seems normal? Except our own families are the worst, usually, and we know it in the back of our minds. It's why we always apologize instinctively the first time someone meets our relatives.

"Come on in," he decided after a long second's hesitation. "Butch! You've got company!" he yelled and I winced. "Butch will be down in a second."

"Thanks." I smiled at the man.

"I'm Butch's dad," he said, standing there awkwardly. It didn't seem like he was used to having company.

"Great," I nodded. "It's nice to meet you. I'm Butch's girlfriend."

"Oh?" He scratched his head. "I thought he was dating Linda?"

"He was," I sighed airily. "But Linda came down with a rabid case of syphilis, so..."

"Excuse me?" The man blinked hard.

"Well, that's what I heard." I bit my lip. "Or was it gonorrhea? I can never remember."

"Uh..." He looked around, wanting to see anything but me just then. "Butch!"

"I'm here, Pops. Geez!" Butch walked into the room, which I guess you'd call a front parlor ... or something. It looked like a living room, but without a television...

"About time," his dad grumbled. I wasn't sure, but I started thinking that I hadn't made much of a first impression.

"Hi Ashley." Butch smiled at me and at least he looked friendly.

"Hi!" I smiled back at the boy and he looked nice, kinda dressed up in jeans and flannel shirt. "Are we going to a rodeo?"

"What?" He gave me a confused look and I'd sorta forgotten I wasn't a tomboy, as you can tell.

"What's this about Linda getting sick?" his dad demanded.

"What?" Butch really looked confused then...

"Come on! I'm double parked!" I said with a giggle, grabbing his hand. "Nice meeting you Butch's dad!"

"Uh ... Bye Pops!" Butch didn't seem to mind being dragged out of the house, but his father wasn't smiling.

"You're dad's really nice." I said, holding Butch's hand as we walked towards my motorcycle, but I didn't mean a word of it.

"He's kinda weird," he shrugged. "Sorry about that. Ever since him and my mom split up..."

"Yeah, everybody's dad is weird," I told him. "Don't worry about it."

"I thought you said he was nice." Butch grinned like he'd caught me in a lie.

"I lied," I said. "Don't worry, I lie all the time, but I'll always tell you when I'm doing it, okay?"

"Yeah, I guess so." He laughed. "You're the strangest person I've ever met, Ashley."

"You don't know half of it yet, boyfriend." I giggled. "Did you break up with Linda yet?"

"How do you know about her?"

"Me and your dad talked all about her," I said, straddling my motorcycle. "He heard she had syphilis or something."


"I dunno, that's just what he heard." I frowned at my dress and decided not to tuck it under my butt. I felt sort of self-conscious with Butch watching. "Are you coming?"

"Where did he hear that from?" he wondered, getting on behind me.

"Ummm ... I think I told him," I admitted with a laugh. "Anyway, you gotta hold my skirt down, okay? But no feeling around down there, I don't wanna freak you out."

"Freak me out?" Butch asked. "What's that mean?"

"Exactly what it sounds like," I said. "Hands on my thighs. I won't drive too fast, just keep my skirt from pulling a Marilyn, okay?"

"A Marilyn? Yeah, um, okay," he nodded. "Where are we going?"

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