Set sail with Cailico Jack

Starring at my reflection in the pub looking glass, I am disappointed to recognize myself. 

Although the handkerchief hides the feminine curve of my neck and my late father’s seaman jacket conceals my chest, my face is smooth and my voice high. I may not be mistaken for Blackbeard, but I’ll pass as a prepubescent powder monkey.

My swayed walk and act were enough to fool the pirate at the bar into offering an apprenticeship. Hopefully in the sober daylight he’ll still be convinced. It didn’t take much, just a dash of amazement at his most recent mediocre accomplishment, a bit of flattery, and an earnest offering of my service. My being recently orphaned also tugs at the heart strings.

Jack Rackman stumbles into my shoulder and pulls me out of my thoughts. With a bottle of rum in hand he gathers his crew, which now includes me. On the way back to the boat I survey my new shipmates. Twelve or so men, most aged with sun-worn skin. Some stern and brawny men jostled their way through the crowd bringing two petite comrades into my view.

From their stance next to Rackman I infer they are of importance, but they look young. The pair seemed close and wore matching steely glares. Although I was a bit taller I would not relish the fight to fight either. 

After a trek out to the harbor one of the small men, who I heard referred to as "Bonny" shouted, "Jack! Read! Look." Ahead is empty sloop.

Rackam approaches the single-masted vessel and turns to Read with a grin. 

Read hops aboard to check for any inhabitants, but only guns, ammunition, and food stores were found. 
Bonny joined Read onboard.

"What are ya waitin' for? Board your new home before the old captain returns!", urges Bonny.

The men waste no time following Jack aboard. My heart is racing, but I fall in with the others. First hour on the job and I'm already committing a crime. The crew swiftly acquainted themselves with the ship, and the harbor soon became but a dot on the shore line.

The air on the ship is electric as everyone runs around on a treasure hunt for food, weapons, and liquor.

I slipped to the sleeping quarters. The pandamonium was a bit much for me. I had a long day and felt exhausted from all the change in my life. As I neared my hammock I happened upon Bonny changing clothes.

Startled he turned around, holding a shirt over his chest. 

"What are you doing here?" hissed Bonny.

"I- I was just turning in, but if you need me to work I can-," I trailed off. His body looked like mine. Toned but slender arms with curve through the torso. Bewildered I opened my mouth before I could stop myself. 
"Are a-are you a wo-?" I questioned.

Before I could blink she had me pinned to the wood siding by a firm grip around my throat.

"You musn't tell anyone," she growled.

"Never," I stammered. She released me to catch my breath and continued to put on her shirt. I met her gaze and opened my shirt revealing binding around my chest.

She gazed at me, surprised. Read approached and I quickly covered myself, warmth rushing my cheeks.
But then I realized he too may be a woman. Or he was Bonny's lover. Their bond was evident.

"She knows," exclaimed Bonny. "Rackam has brought another woman into the crew."

Read chuckled, "Perhaps we three should join the theater instead of a pirate crew."
    
Relieved I laughed as well. 

It's not like we had many other options. Life for men has boundless direction, choice, and potential expansion. A man, even a man with no means, can join the royal service, apprentice, own a property or establishment and make a life. 

I don't know how these women got here, cross dressing to live as sea thieves, but I'm sure it wasn't because they had any chance of a life as a woman back in England. I had no family, money or marriage prospects. My brother joined the Royal Navy a few years back, so I cannot have a home with him. 

"Don't ever let anyone know your secret. Fight twice as hard. Use your wit where you don't have strength, and you ought to be fine" assured Read.

Perhaps I am going to enjoy this adventure after all.

Sources:

Cordingly, David. Under The Black Flag. Harcourt Brace & Co., 1995.

Stockton, Frank R. Buccaneers and Pirates. Dover Publications, 2007.