On-board Entertainment

"Fine!" I said. "Fine. If it'll get you off my back, I'll do it." I tried to act cool. Give me the dress."

The captain passed it over. He picked a set of lingerie out of the case, a floaty summer dress, and a pair of nude 5" heels.

"These too. As they say, 'if the shoe fits'."

Nikolai cackled behind him. He had a hungry look about him, which terrified me.

I turned away from them to try and preserve an ounce of modesty. As quickly as I could, I stripped down and pulled on the panties. They were made of a dark teal green lace, which looked too good against my pale freckled skin. I could tell the quality as I pulled them up my legs. The thin fabric thong slipped perfectly between my cheeks, and my small package was tucked away neatly.

Fuck, they look like they were tailored to me. I had never noticed that I had such a pert ass before. At least the bra wouldn't fit, I thought.

It did.

Caitlyn's A cup tits couldn't have been much bigger than my own, and my narrow shoulders didn't strain the straps even slightly. It was humiliating knowing I had the same physiology as a 20 year old girl. I stepped into the summer dress. I struggled with the zip for a few awkward seconds before I was forced to ask:

"Could... Please could you do up my dress?"

Nikolai stepped forwards. I felt his hands and his breath on my bare shoulders, and the hairs on the back of my neck stood up. Worse, I could feel his dick pressing into the base of my spine. He was erect. Nikolai slowly zipped me up. When the zipper reached the top, he gently slapped me on the ass. I jumped.

"Good girl." He laughed.

I turned around. I could tell from the hungry looks in the men's eyes that they like what they saw.

"And the heels." The captain ordered.

I slip the nude stiletto pumps onto my feet, and wobbled slightly.

"Happy?" I asked, trying to sound as manly as possible, but my voice was on the verge of cracking.

"Damn, that's a fine piece of ass." The captain said this cooly, and his crassness surprised me. "How'd you keep those legs so smooth boy? Do ya shave em?"

"Fuck you! That's just how they are!" I said.

"That's not very polite for someone depending on my generosity. Where are your manners?" The captain's question was rhetorical.

"I... I'm sorry. But this is totally unfair!" I pulled at the hem of the short dress.

"I'm not going to debate this with you. It's fairly obvious the belongings are yours. Including this." The captain held up a brick of the narcotics. I tried to interject, but he continued, cutting me off.

"The real question is what we do with you now. You're facing a long stretch in an Italian prison if we turn you in when we get to Europe. An even longer sentence if the US wants to extradite you back to face charges..."

"I don't see you having much fun on Riker's Island, sweetcheeks." Nikolai added.

I was terrified. There was no way I was going down for a crime I didn't commit! I felt faint.

"Please..." I said weakly.

"Perhaps there is something we can do for you though" said the Captain.

I looked at him hopefully.

"I'll allow you to serve out your debt to society on this ship. Your sentence will last the duration of your journey. How does that sound? Does that sound fair to you Nikolai?"

"Sounds like a great plan boss. I think I can speak for the whole crew when I say they'll find that very acceptable." Nikolai said.

Captain Leadman turned back to me.

"Great. So are you in agreement young lady?" He asked.

"I... I don't want to go to prison. Can you promise me you won't report this?" I quivered.

"You have my word. By the time we land in Naples this episode will be completely forgotten." Said the captain.

I hesitated. This felt ominous. But the Captain was holding out an olive branch, and there wasn't any alternative but to take it.

"Ok then, we have a deal." I said.

I shook the captain's hand, and then Nikolai's.

"So what would you like me to do first? Swab the deck or something" I tried to laugh it off.

"Something like that" said the Captain. "The boys are going to love seeing you in that dress at poker night. Some of them didn't get a chance to blow off steam in New York."

The penny dropped.

"Nonono!" I backed away, tottering precariously in the high heels. "I'm not gay! This isn't what I meant!" I felt so naïve.

Nikolai scooped up the luggage with my clothes in - my boy clothes - and slung it over his shoulder. The smuggled drugs were stacked into a carrier bag and set outside the cabin door.

"I think the clothes in there will give you everything you need for the journey." The Captain said said, gesturing to Caitlyn's suitcase. "See you at dinner."

Nikolai winked and blew me a kiss as they exited the cabin.

Grimacing and dejected, I dropped onto the bunk. My high heels dangled helplessly above the floor. I was out of options.