Tom’s jaw dropped. In his hands he held knickers, ladies knickers that were cream with black scalloped trim on the leg openings. They were sheer enough that he could see his fingers semi-translucently through the cool, slinky fabric even when he did not hold them against the brass lamp’s light.

On the bed that Allan laid down on, all the while still wearing a mist slimed jacket and smoking a cigarette, was more lingerie: a blush pink corset with white laces, wine red garter belt with black suspender straps and matching garters, a solid black teddy, more pairs of panties in an array of neutral colors and ribbon and lace trims, a bra that coordinated with the knickers in his hands. Allan placed his cigarette at the lime Bakelite ashtray by the lamp before surprising Tom with another package under his grimy, burlap enveloped pillow.

“Make up, Allan?” Tom gasped as lipstick and black tubes and pots of other things he did not know the names of clanked atop the mountain of supreme femininity.

“Why not?” Allan smirked before puffing away again. “I thought red lips would complete the look.”

Tom sensed his romantic tomfoolery with Allan would bring upon some complications at some point. He knew how uncharacteristically childishly giddy the other man was when he finally agreed to indulge into the first mate’s closet kink. He felt great for bringing Allan such joy, but all that girl stuff on the bed was overwhelming to him, a man that never even gave much a thought about ladies underwear until a week ago.

The quantity before him was not the only thing. It was also how tiny everything was. The knickers in his hands were the damn lightest and smallest pair he ever held. Granted, that was the first pair of ladies knickers he ever held, but he was positive not all ladies knickers were so tiny they could fit into his not-so broad palm. Did Allan really measure him correctly before their last stop?

“But how am I supposed to fit into these?”

Allan heartily laughed. “Just try it on. You’ll be surprised. Oh, and here; I don’t want you to forget these.” He tossed the brasserie across the room and onto Tom’s sock covered feet.

He gulped before beginning. Slowly Tom discarded his male clothes behind him. There were no screens or wardrobes to hide under to surprise his lover with the end result, but he hoped Allan wouldn’t mind. Allan had enough time to switch to the other side of his cigarette, put out that one, and light another as Tom took off his pants, his pullover, his undershirt, his boxers, his cap. When the only things left on his person were his khaki colored socks and sock garters, he picked up the knickers he dropped onto the floor pre-disrobing. He stretched them as far as they could go (to shoulder width, to his amazement) before lifting his right leg.

How queer… He thought. Compared to his normal clothing these garments were so light and soft… and comfortable. Of course, his normal clothes were comfortable too, but they were also medium weight and a tad rough at times. Maybe this romp was not going to be as awkward as he thought it was going to be after all.

Squeezing his cigarette between his lips, Allan reached under his bed and grunted while pulling a steamer trunk into view. Out came a blur of platinum blond hair that Allan tossed to Tom.

“Also wear that…”

Tom hopped forward to grab a tube of lipstick.

“…And that. Then the transformation will be complete… For now. I’ll get you some nylons and stilettos next time. Then it will be perfect,” Allan grinned a grin the Cheshire Cat would envy.

When he was done Tom resembled more a reject pin-up girl with Marilyn Monroe short hair and ruby red lips than a sea and wind roughened merchant ship sailor man. He blushed from embarrassment, but also from receiving Allan’s approval, if the first mate’s panting and physical engorgement showed anything. Allan set aside his cigarette and placed his hat onto a bed post, exposing flattened black hair. He undressed into his undergarments and plopped down onto his twin bed with a grunt. It was a bed more suitable for a school child than two grown men, but they would make it work like the last couple times.

Allan spread his broad legs, placed his hands behind his head. He was more obviously excited than he was when he was wearing pants. Tom, also turned on, still stood prostrate across from the bed. He adjusted the bra and knickers so that he was fully comfortable. He pressed his hands against his faux-breasts and rubbed them about. His heartbeat quickened, as did Allan’s breathing. The man on the bed fought the temptation to stroke away.

“Ah yes, just like that… Perfect, Tom! Perfect!”

Tom smiled. His mind flashbacked to various pin ups his comrades posted during the war. He dropped to the floor, bent his legs, pushed out his back and stuck his chest out.

“How about this Allan? Do you like this?”

Allan twitched. “Oh, I love it like you have no idea…” A hand drifted down his chest. “You know what would be even better, lady boy? How about you come here and suck—“

“Mister Mate?” Pablo opened the door with nary a warning. “Captain wants another…”

He blinked, blushing. Tom shook, all the while staying in the same push-up pin-up position. Allan glared at him. When glaring wasn’t enough he gnashed his teeth and snarled.

“…You know what? I’ll just… get the whiskey… myself… And I’ll just… forget this… myself…”

Pablo slammed the door shut. Allan puffed away his anger before facing Tom.

“Well, what are you waiting for? What’s better at relieving stress than a suck and fuck?”