Pirate's Paradox

My first time to actually submit something for a specific contest. What better time than Halloween, right? It's a bit of a slow burn, but finishes hard and fast, so watch out.

All standard caveats, everyone is over eighteen, and you get the requisite happy ending.

A few things are a little sketchy, but it's Halloween, sketchy things happen on Halloween. Enjoy and please leave me a comment when you're finished.

***

It was going to be glorious, Captain Jack Sparrow. The wig alone cost three hundred dollars. It was all a birthday gift from my dad. I told him I'd be able to use it for a long time, even when I went off to college next year. He had been overcompensating ever since our mom died for the long hours he worked and the time he spent on the road. My twin sister Ellen and I played it for all we could. We were both spoiled rotten and knew it. I guess it was only fair that karma was going to step in at some point.

My first issue was that something had delayed my costume, finally arriving the day before the big party I had ordered it for. Ellen's had arrived two weeks ago, and we had ordered them at the same time. If my dad knew what she was wearing, he would have shipped her off to a convent school. She was taking the sexy witch to a whole new level.

Right on top when I opened the box was the iconic tricorne hat, actual leather. This was going to be so awesome. Then the twin belts. Damn, the pistols looked real, and the saber, fuck, this was so worth every penny. The next item confused me. What the hell would Jack Sparrow need with fishnet stockings?

Ellen found me in my room, sitting in the middle of all the pieces of my costume, utterly despondent. I looked up at her and reread the letter I had so cavalierly tossed to the side.

"Dear Ms. Samuels,

We apologize for the delay in shipping your costume. Unfortunately, we could not meet your specific requests. We hope the substitutions we made meet with your approval.

Sincerely..."

Some flunky from Epic Costume Designs had signed it.

"Ray-Ray, we can make this work." She was picking through the items I had scattered around me; bustier, knee boots, flouncy blouse that would expose my shoulders, a short skirt with petticoats, a long red wig, and a few other things.

Yeah, it was a pirate costume, all right.

Technically, Ellen was right. I had sent them so many measurements; they could have cloned me if they wanted to. I knew it would fit. It just wasn't the look I was going for.

Things like this had happened before. My mom had named me Raylin. I guess she thought it was a cool name. Some guys on the football team bullied and teased me mercilessly about how feminine it sounded. My friends all called me Ray. Ellen added another Ray to that. She was the only one I let get away with it. My credit card had my full name, Raylin Joyce Samuels. Joyce was my dad's middle name.

Yeah, it explained the 'Ms.' in the letter, too.

"No way, Ellen. I can't wear this to the party. Can you imagine the abuse I'd get? It's bad enough with the Rick and the rest of the football team and my name. If I show up in this, it will destroy my life. I've been bragging about my costume for weeks."

"What would be worse, you wearing this and blowing everyone's doors off, or you getting ridiculed for wearing the same costume you wore last year? Especially after all the bragging you've been doing."

"But..." I rubbed my chin. It had taken me forever to grow out the wispy mustache and beard I needed for Jack.

"So, um... You tell everyone it was a setup. It's all a big prank. You tell them you did it on purpose because they all make fun of your name being feminine. They would expect Jack Sparrow, and you show up as Jackie Sparrow. Boom, jokes on them. Right?"

"Ellen, I don't know..." I picked up the bustier and looked at it. I had so many doubts, but she knew I was at least thinking about it.

"Come on, Ray-Ray. Just imagine the look on Rick's face when he sees you and you own this."

Why was she so excited about this?

"It'll be great. I promise." Now she was begging me.

"Ok." I let out a massive sigh. "Where do we start?"

"First, try it on and let's see where we need help."

It was like a jigsaw puzzle and took a few tries, but we finally got it on. My briefs were a big no under the skirt and with the fishnets, so Ellen talked me into a pair of her panties, a skimpy black thong with lace trim. Her logic was, if you're going to wear a skirt that shows off your ass, well, show off your ass. Her witch costume certainly did.

If I were being honest, I'd have admitted they kind of felt nice. Even the string up my crack wasn't so bad. We had to look online to find out what to do with junior and the twins. It turns out, there are a lot of guys that enjoyed dressing as girls. The more we worked and played with my costume, the more I sort of understood the attraction. The bustier even gave me modest breasts when Ellen cinched it behind me. When she added the dark eyeliner and a few other touches of makeup, well, I was almost as sexy as she was going to be.

"You'll need to shave and stuff, but I think you're going to have the best costume at the party." Ellen was standing behind me, looking over my shoulder at the tall red-haired pirate in the mirror. It mesmerized me how good I looked.

"What do you mean, 'and stuff'?"

"Well, I mean, you could come with me to my spa and get your nails done, maybe even get some earrings. Just stuff like that. They can even take care of all your hair." There was something in her voice that bothered me. Honestly, though, I was so wrapped up in the beautiful pirate in the mirror, I didn't even listen.

"Yeah, sure." I let her take care of everything. She took some pictures of me in the costume, so the stylists would have something to work with. I got undressed and put on my regular clothes, and we took off.

Yeah, they took care of my hair, all right. All of it from my nose down. Even there. At least when they had finished torturing me, I got a nice massage. Then two girls descended on me like harpies from mythology. One of them working on my hands and feet, the other on my face. When they were done, there was a girl in the mirror. Sure, she had short hair that was now in a kind of pixie cut. That's what they called it, but damn, she was cute.

They did something to my eyebrows and somehow made my eyelashes longer. Ellen was grinning like she'd won the lottery or something.

As a final touch, the girl doing my manicure and pedicure pierced my ears while the girl doing my face glued something to my chest. Now the girl in the mirror had earrings and slight boobs.

My brain stopped working. The incongruity with what I saw and what I knew I was staggering. My nails were bright red, and half an inch longer than they'd ever been. The studs in my ears were simple red crystals, but they had little loops on the posts that allowed the stylist to hang bangles from them. And my face, damn. My makeup looked so natural, yet it accented my green eyes and softened any masculine features I might have had so well.

The forms they glued to my chest weren't big at all, but when I put my shirt back on, they were still obvious. The perky nipples sticking out, teasing their presence.

Ellen looked just as good as me. Ok, she looked better, but she'd had years and years of practice and more to work with.

She reached into her bag and handed me my wig. "I think I like it like this for now." Still in a daze, I heard myself say the words, but they sounded like someone else was saying them.

As we made our way out of the mall, I lost myself in a word of new sensations. The way my modest, fake boobs moved with me, bouncing with each step, was exciting. And then there was the way even the coarse fabric of my shirt and jeans made my now hairless skin tingle. What got me the most was the looks from the guys we passed. None of them laughed or jeered. They were staring, ogling me.

It was me that stopped at the kiosk and bought the bangles for my wrists. I was the one that stopped in Zales and bought three rings for my fingers and an inexpensive and overdone gold cross necklace. I was going to be a pirate, right? Lost in this new wonderland, I wasn't sure I knew the way back. I was even less certain I wanted to find it.

"Ellen, what's happening to me?" It was almost a whisper. I had let her go to the counter and order our pizza while I held a table in the food court.

"I don't know, but I have a feeing you like it." She gave me a weak smile and put her hand on my arm.

"But why? I've never even thought of doing any of this before. It was just supposed to be for the costume." I could fear the anxiety building in my gut. "Ellen, I like this. The way I feel, the way people look at me. What do I do?"

"I think you get through the party tonight and then we go from there. Makeup comes off. Hair grows back. You have an appointment tomorrow to redo your nails, so you won't have to worry about that. The rest, well, your ears will heal, and the boobs go in a box." Her smile turned into a grin.

The thought running through my mind was, 'what if I don't want them to?'

We ate our pizza, and I answered her questions about what I liked and what I didn't. There wasn't very much on the didn't side. By the time we got back home, we had to scramble to get our costumes on. With the wig and the rest of the costume, Even I didn't recognize myself.

"New plan." I smiled at Ellen. "Raylin couldn't make it. He's sick or something. Call me Riley. Let's see if anyone can figure it out." It was my turn to smile and then laugh. Riley was gorgeous.

The Uber driver that picked us up almost couldn't drive because he kept looking in the mirror at Ellen and me.

It was poetic justice that the first person we saw when we got to the party was Rick. He practically ran to meet us when he saw us coming up the walk.

"Ellen, looking hot as always. Who's your friend, and where's that loser brother of yours? He get his feeling hurt and stay home?"

"Nope. Hundred and three fever. He was looking forward to showing off his Jack Sparrow costume. This is my friend Riley."

"Wow, Riley. I don't think I've seen you before. I'd remember someone as hot as you. Name's Rick." He smiled that kind of crooked smile he was famous for. I could see why girls went for it. I mean, he was good looking. It was also obvious he had no idea who I really was.

"Oh, so you're Rick." I gave him the most dismissive look I could manage. "I've heard about you. Come on Ellen, I need a drink."

Down. In. Flames. It was wonderful. Rick looked like he'd lost his puppy or something. I honestly didn't think he knew how to react. He was the lead dog, the alpha at our school. It was common knowledge, or urban legend, that he could have any girl he wanted. I'd seen him with more than a dozen and I'd only met him in junior year.

Ellen and I made our way inside. At eighteen, we were both too young to drink legally, but that didn't stop us from getting drinks at the bar. The party was mostly college kids. A few seniors like Rick and Ellen, and now me. Ellen always managed to get invited.

Rick because his older brother was hosting the party. Ellen, because, well, she was Ellen, and she was dating Rick's older brother.

We got our drinks, and Ellen took me to meet Tony. Of course, I had to pretend I'd never met him. He'd had dinner at our house several times. He was finishing his economics degree with plans for getting an MBA right after. How Rick was his younger brother baffled me.

Some college buddy of Tony's asked me to dance. I looked at Ellen; she shrugged. I figured why not, and Eric and I disappeared onto the dance floor. The heels on the boots that came with the costume were my biggest problem. I'd practiced before we got here, but it was still a challenge. Eric seemed to understand, and besides, it gave him an excuse to keep his hands on my body, which he seemed to enjoy. I had to admit; it was kind of nice.

This whole being the hot chick at the party thing was fun. Right now, Eric had me, but I could see all the other guys eyeing my scantily clad body, wondering when their chance was going to come. I lasted three songs before I realized the guns and saber were a bigger problem than the heels. Eric pointed me down a hall to a bedroom where people were leaving coats and stuff like that. While I went to drop them off, he went to the bar to get me another drink.

"So, exactly what have you heard?" Rick seemed to have regained his composure and stopped me just outside the bathroom as I made my way back to Eric to get my drink.

"I honestly don't think you want to know. Now, excuse me, please." I slipped past him, ducking under the elbow he had propped up on the wall to block me.

I was pretty sure he muttered "Bitch," or something like that, but I didn't care. The more frustrated he got, the better I liked it.

Eric and I danced and drank. I danced with several other guys, but always seemed to end up back with Eric. Rick had asked me once and I'd just laughed, turning around and grabbing the first guy I saw.

At some point, I got talked into a game of beer pong. I sucked, which meant I drank a lot. Eric rescued me and took me out in the backyard to a small bench swing, where we sat and just talked.

He was actually very interesting. His cowboy costume was all the stuff he'd worn when he did street performances in Jackson, Wyoming. He was one of the bad guys and loved dying for the audience.

He knew Tony from high school, which meant he had graduated a few years before Ellen and I moved here. He already had his degree in engineering and was working on his masters. Some big oil company in Houston was paying for it. He'd be gone just after Christmas.

We argued a bit about which of us would win a gun fight. I had two pistols, but his gun held six shots.

"Yeah, but you'd never shoot a girl as pretty as me."

"I might." He smiled and pulled out his pistol, twirling it around his finger. "Unless she kissed me, that is."

I laughed and then saw Rick come out on the back porch. With a devilish grin, I leaned over and let Eric give me my first kiss.

This was so not how I saw that happening. There was a girl in my class I was planning on asking to the Homecoming dance. In my mind, she said yes. We danced and just as the last song ended, my lips met hers. The monitor called us out on it, and we ran out of the gym, hand in hand, to find some place private to do it again. In the backyard of some party with a college guy I'd just met, I'd never in a million years imagined it would be like this. And I'd never in a billion imagined I'd like it, that I'd feel it in my gut the way I just had.

My eyes fluttered as my lips separated from Eric's. Short of breath, my heart was racing. That was nice, very nice. I liked it a lot. So much so that I slipped my hand up his arm and around the back of his head and pulled his lips to mine again.

"I guess you're not going to shoot me then?" I let out a soft sigh and giggled.

Fuck, I was so screwed. This was all supposed to be a joke, a massive prank. The longer the night went on, the more it looked like it was on me.

"No, but I might try to do worse if we don't go back inside." Damn, his grin was so adorable. And those blue eyes.

What the hell? Where did that come from?

"Yeah, that's probably a good idea. Holster that side arm, cowboy." I gave him another quick peck on the lips and let him help me to my feet.

"What's the deal with you and Rick, by the way? He came out on the porch and looked at me like he wanted to rip my head off."

"I shot him down pretty hard. Kinda got the feeling he doesn't hear no a lot." I slipped my hand into Eric's and hugged his arm.

"Well, I'm glad you did." He squeezed my hand in his. I could hear his heavy breath and deep sigh and could almost feel the smile on his face. I think my smile was bigger.

I was in so far over my head, and I didn't even care.

Eric and I danced and drank and even found a secluded corner to make out for a while. I had lost Ellen a long time ago and decided I didn't care. I could get my own Uber home, or maybe Eric could give me a ride. The ramifications of what I was doing were so far from my mind, they didn't even exist.

I passed Rick a few times. He looked confused, hurt, and a little angry. He finally reached out and grabbed my arm. "I need to know. What specifically have you heard about me?"

"Do you really want to do this? Here? Now? In front of all these people?" I saw Eric working through the crowd from one direction and Ellen another.

"Yeah." Rick nodded.

"Fine!"

I started counting on my fingers.

"One, you're an egotistical jerk. Two, you can't keep a girlfriend for more than a couple of weeks, and then you talk to everyone that will listen about what you supposedly did with them. Three. You're a bully, compensating for something, I guess. God only knows what. I mean, look at you. You're tall, athletic, and handsome. Your older brother is a prince. What the fuck happened to you? What are you compensating for? Seriously, Rick, you're just damaged goods. I'm surprised you can get a date at all."

I jerked my arm free from his grip and left him standing there. The look of shock on his face almost made me feel sorry for him, but letting all of that out felt so good, so justified. If I'd tried that as Raylin, I'd have ended up in the hospital, I was sure.

"Riley, are you ok?" Eric and Ellen said it in unison. When I let Eric wrap me in his arms, I thought Ellen was going to faint.

"Yeah, but I need a drink." I looked up at Eric and let him lead me to the bar.

"And I need an explanation." Ellen followed right behind us.

We all ended up in a corner with Tony.

"Damn, that was brutal, but he so needed to hear every word." Tony was laughing. "Just be careful he doesn't track you down. My little brother does not like to be embarrassed like that."

"I don't think I have to worry. I'm just visiting for the weekend." Damn it. Why didn't I think before I opened my mouth?

"Really. So, do you have plans for tomorrow? I've got an extra ticket to the game." Eric jumped on the opportunity.

I looked at Ellen. She looked at me. My eyes were pleading. Hers were laughing.

"No, in fact, Tony and I were just talking about getting you to ask her to join us." Leave it to my twin sister to throw me under the damned bus.

The crowd thinned out. I went and got my guns and saber, and Ellen called us an Uber. Rick had disappeared. I guess locking himself in his room. Tony promised to go talk to him before he did something stupid.

The kiss I got from Eric at the door made me weak in my knees.

"I still want that explanation." Ellen laughed as our driver pulled away.

"I don't have one. It just feels so good, so right. Ellen, whatever this is," I pointed at myself, "I like it a lot."

"And you're not mad about the game?"

"No. I want to see him again. As Riley. I just need to figure out how to tell him the truth and not get punched in the face for it. It's like I'm a different person. I have all this confidence. If I'd gone as Jack Sparrow, I'd have spent the entire party hiding from Rick. This was so amazing. The world just treats pretty girls different from the way it does geeky guys, I guess."

"I can't argue with that, and everybody wanted to know who you were. You broke more hearts tonight than just Rick's." I blushed. She laughed.

Fortunately, the game was an afternoon game, which meant I had time to get my nails redone. Ellen and I talked about it, and I left them about a quarter inch long, but with just a very light pink color that almost looked natural. I replaced my studs with little Longhorns. Ellen and two pair, and let the stylist put on very light makeup. I was still going as Riley, but I wanted to play it down some. I had all day tomorrow to decide what Raylin was going to keep.