Joseph Joestar | Sing

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MALE READER LEMON

~adult content and cross-dressing relationships~

Inspired by the song Sing, Sing, Sing (With a Little Swing) by Louis Prima

(Art is not mine cred to zaremoine on twitter)

It was late one fine evening in New York, New York. I was sitting on my lonesome at the bar on 20-some street while some radio droned on in the background. The smoke clogged the room as I sipped on vodka on the rocks. The bartender walked over with a shot of tequila and placed it in front of me.

"Courtesy of the, lady." The way he said 'lady' made me quirk and eyebrow and I let my gaze wander over to the corner of the bar where she sat. My eyes were graced with a larger woman, not in the typical sense, with biceps quite possibly larger than mine but an impeccable taste in fashion. I nodded at her and downed the shot, raising the glass to her after the liquid was gone. She smiled and she almost skipped over to sit next to me. She smelled of that spunky perfume Tabu, and man did that vanilla make her enticing.

I'm what most nowadays would call a walking contradiction since I like men and women, but since being queer was a horrid thing, I just let on that I fancied women and sent more discreet flirts to men. So, I din't mind that she was more of a masculine type, if anything it was refreshing from all the slender waists and frail everythings that were advertised as desired.

"Would you like another shot, cutie?" I was less than shocked at the deeper voice that came out of the dashing woman beside me, but had to glance her way to make sure.

"Maybe a few," I wink at her and wave over the bartender. "Two shots of the tequila you gave me earlier. Put it on my tab." He nods and rolls his eyes a tad. I choose to ignore this since the owner of this joint owes me a few favors, so to say.

A few rounds, and by a few I mean ten, I was a tad tipsy and Josephine's falsetto dropped into her actual voice. She was nearly 'stand on the counter' drunk when a song came on the radio that begged us to dance to. Being a 6'9" guy served me well with Josephine, since she was a good 6'5". The drums started in and we looked at each other. The trumpets came in and I grabbed her hand and we were beginning a drunken swing around the small dance floor. We swung around for a good four minutes before she grabbed my tie and whispered in my ear, "I know a real nice hotel down a block, if you don't have a place to stay tonight."

I slipped my hand over her butt and she smiled and kissed my cheek. I nodded to the bartender and we slipped out to the street. She stopped for a moment to take off her flats and wrapped her hand around my arm. We walked into the hotel and she already had a room, so we sped up the stairs giggling like teens on their first night after a dance. She opened the door to the room and pulled me in by my tie, kissing me like it was the solution to all her problems.

When we pulled apart she panted out, "You know, Mr. (Y/n), no man has ever come back to the hotel with me. I was starting to lose my confidence." She pulled my head closer to her and she whispered, "I hope you treat me right, you'll be my first man after all, Mr. (Y/n)."

I grabbed her waist and pulled her body to mine, meeting our lips in a passionate kiss, leaving the world behind. Her mouth opened with an invitation I simply couldn't refuse. Our tongues battled for dominance, mine eventually winning, and we slid onto the bed. I began to kiss down her neck and strong jawline when she placed a hand on my shoulder, easing me off.

"What is it, dear?" She turned red when I called her dear, but turned away in embarrassment.

"I- I haven't been, well, entirely honest." She couldn't look me in the eyes and I began to worry something was horribly wrong. I gently held her hand and pulled her up so she could sit on the edge of the bed. I sat down next to her, still holding her hand.

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