A/N: I still can't upload any images, so for OC's I'm going to add character descriptions at the beginning of the story so you know what they look like.
Dolly
Real Name: Giorgio Gallo
Description: His hair is black and short, but wears a wig that reaches to the small of his back. His eyes are brown and he has a tanned skin tone, reflecting his Italian heritage. In the story he wears a red sheath dress. Google "sheath dress 1920s" to see what it would look like. He is 18 years old.
Bella
Real Name: John Macbeth
Description: His hair is blond and curly. His eyes are blue and has pale skin. He's originally from Georgia, so he has a southern accent. In the story he wears a golden flapper dress. Google "flapper dress 1920s" to see what it would look like. He is 23 years old.
Mistress
Real Name: William O'Hara
Description: His hair is long and ginger. He has green eyes and pale, freckled skin, reflecting his Irish heritage. He wears a green sequin dress. Google "sequin dress 1920s" to see what it would look like. He is 35.
Diavolo
Real Name: Tyler Becking
His head has been shaved bald. His eyes are brown and he has pale skin. On the sides of his temples are demon horn tattoos. He wears classic gangsta mafia clothes: a tuxedo and fedora.
(Y/n)'s POV
In my time, time travel is not only possible, but common. People travel through time all the time. Usually this causes no problems, as anything you do simply creates a new timeline separate from the original, so no grandfather paradox. However, that doesn't mean people should feel free to do as they please. My job as a SPLE (Space Time Law Enforcement) officer means I travel through time and space to apprehend those who misuse this technology. My assignment now is to apprehend Tyler Becking. He traveled to Chicago in 1925 and established a criminal empire rivaling that of Al Capone's. According to reports, he's taking over many speakeasies by force. His next target is The Bellibone Egg, a speakeasy known for being popular among queer people.
I wear a tuxedo as I enter the club. The place was pretty spacious. There was a large area with table and seats in front of a stage where dancers and singers entertained the guests. What caught my eye was that the "female" dancers were men in drag and the "waiters" were women in men's clothes. Men flirted with other men and vice versa for women. This was basically an early gay bar. Though, with higher risk, as not only was the sale of alcohol illegal, but so too was homosexual acts.
I see the owner "Mistress". Real name is William O'Hara. A gay crossdresser in his mid-thirties. Despite there being no hormones and plastic surgery during this time period, he has a surprisingly feminine appearance for his age. If he was a woman, I would call him a MILF. What do you call someone like him, though? A femboy DILF? A femDILF? Right next to him is someone else, another crossdresser. I don't have him on record. He looks to be in his late teens. He's pretty cute. I make my way to them and introduce myself. "Hello ladies, may I have this seat? I would love to talk to such beauties like you." I flirt. It will be awhile before Becking will show up. Might as well see if I can score some bussy while I'm here.
Mistress's POV
A handsome man came up and asked to sit with us. I can't the open advances from such a man. "Of course. Sit where you'd like." He introduced himself and asked for our name. "I'm Mistress and this is Dolly. She's new here and is very shy, so please be gentle with her." Dolly blushed intensely. As we were getting to know him, a familiar voice spoke up. "Oh, who's this?" Coming from the stage was my singer Bella. I introduced them and I ordered some moonshine for us. As we got drunk we all flirted with him and he flirted back. His intentions were clear. He wanted to take one of us to some private place and honestly I was this close to dragging him up to my room so I can ride his cock. I can tell Bella was thinking the same. While based on Dolly's intense blush, the idea also entered his head.
