[October 1927 – Chicago]
Vincent ‘Bugsy’ Stallone came into his office in a bad mood.
“Those bastards from Justice are getting to be a real pain in the arse. We just lost another shipment of beer between the Port and the Warehouse. It is that agent Ford again. He gets everywhere, the bastard. He must have informants on almost every street corner.”

The blonde-haired woman sitting next to his big polished oak desk looked up from filing her nails.

“What are we going to do? We have customers who rely on us. That’s the fourth this month.”

“Doll, don’t I just know it. Now that Big John and the rest are out of action it is down to the likes of us to keep this city drinking.

“Won’t this just blow over?” asked the woman.

“Judging by the number of agents involved with the last interception, then no it won’t. They had over fifty feds just to take down two trucks. They were sending a clear message to the likes of us. I think that they are saying that ‘the good times are over’.”

The woman didn’t say anything.

“Then Luigi Trapiani’s boys had a fire fight with Marco Tostitos’ crew. Eight dead and ten wounded and that was just over who supplies one bar on the South Side. Things ain’t what they used to be that’s fer sure...”

The woman nodded her head in agreement.

“I guess it is time then?”

Bugsy sighed.

“I think so. We’ve had a good run, but yes it is. Today is the day we both hoped would never happen but… well we have planned for this day.”

The woman stood up.

“I guess I should go and pack then?”

“Doll… Are you forgetting the first rule of disappearing?”

“Oh sorry. Yes. Make it look like you went out for a newspaper.”

“Exactly. I’ll get George going. He goes tonight. We go tomorrow night. Until then, we act as normal. Got that Doll?”

“Hey, don’t Doll me. Who’s the real brains behind this outfit eh?”

They both laughed. They'd run the business together for the past three and a half years.

“Ok. But I have to keep up appearances, don’t I?”

She just glared at the man and went back to working on her nails.

---

Bugsy left the office after removing an already wrapped package from his safe and went downstairs to the garage where Lonesome George was lovingly polishing the big black Buick that he drove for the Boss.

“Hiya Boss. Want to go out?”

“No George. Time for your mama to take ill.”

The smile that George sported through thick and thin disappeared in an instant.

“That bad eh?”

“Yes. We are pulling the plug. You know the plan don’t you.”

“Yessir Mr Bugsy. I know de-plan,” said George putting on a fake accent.

“Good. Now go to the ‘EL’ and make that call to your cousin in St Louis.”

"Yes Boss.”

“This package that needs to be mailed when you go out. Can you get it done without anyone who might be tailing you knowing?”

“That I can Boss,” said George as he picked the package up off the table.

“It contains a Bible if anyone wants to know.”

George laughed. He knew very well what was inside the Bible.

“Don’t forget where you are to meet us tomorrow night and don’t forget to switch cars before the pickup.”

“I know the plan Boss.”

Bugsy smiled and shook George’s hand.

“Good. We go tomorrow night.”

“Ok Mr Bugsy,” said George as he tipped his hat to his boss.

---

An hour later, the first part of the plan fell into place when a Post Office messenger delivered a telegram at the HQ for George.

“Oh, Mr Stallone Sir, My Mama is very poorly,” said George as he played his part right down to the letter.

“Well then, don’t stand there, get yourself on the next train to St Louis,” replied Bugsy.

“What about my duties?”

“They can wait. Your Mama is your only Mama. Go be with her and make her better.”

“Thank you kindly, Mr Stallone.”

George hesitated.

“Well, what are you waiting for?”

“Her treatment will cost a lot of money.”

“Oh, is that all?”
Bugsy reached into his jacket and extracted his wallet.

“Here, will this do for now?” he said handing over $500 in fifty dollar bills.

He added a well-used few tens and twenties for good measure.

“Yessir Mr Stallone.”

“Well get the hell out of here and don't come back until she is better you understand?”

"Yessir Mr Stallone, I understand."

---

That night, Bugsy and Stella went to dine at one of the city’s top restaurants. This was a pretty common event for them. They made sure that they were seen by all the right people in the city. Bugsy drove them to the restaurant in the Buick.

A couple of people who were known to Bugsy asked why he was driving and not George. That was uncommon for them as George had been ever present at these evenings in the past. Bugsy simply told them that George had gone to visit his sick mother in St Louis. His mother was fit and well and living in South Carolina but no one in Chicago would know that.

For the past three years, Bugsy, Stella and George had concocted a history for themselves that was pure fiction. After seeing the increasing level of Mob Violence and then the Department of Justice getting ever more vigilant over their enforcement of the Prohibition Laws. They’d even resorted to wading in with tommy guns blazing and not even bothering to ask questions, it seemed to them that it was only a matter of time before Bugsy’s operation rose to the top of the list.

They knew that it was time for the three of them to hit the road and leave Chicago far behind them for good.

---

The next day, Bugsy appeared as usual at his HQ and supervised the distribution of tinned and dry goods. This made up the ‘legal’ part of his business empire. No moonshine ever came to his HQ. In fact, unless you looked really hard it appeared that nothing illegal went on there at all. That side of the business was carried out in a basement that has been dug on the ‘QT’ a few years before. You couldn’t even get into it from the main part of the HQ unless you knew which panel in Bugsy’s office slid open.

That evening Stella and Bugsy went for dinner at a small Italian place close to the Train Station. After a good meal where Bugsy left his usual big tip, the got into the Buick and headed home. As Bugsy had feared, there was a black sedan on their tail.

“We have a tail,” said Bugsy to Stella as she stopped at an intersection. The phone call that Bugsy had made before leaving the Restaurant had anticipated this event.

“Can you lose them?”

He smiled back at her.

“All in hand my dear.”

A couple of minutes later, Bugsy turned sharply into an alley. The exit was clear so he put his foot down and sped across an intersection before turning out of the alley.

As he did so, he saw the car that had been following them get blocked off by a delivery truck. It was one of his trucks on a legitimate delivery operation. It had just been told to wait for Bugsy to pass by before driving up to the loading dock.

“So far so good.”

Bugsy then headed for the South Side. This was ‘mob’ territory. Neither Bugsy or any of his team rarely ventured into this part of the city. He stopped the Buick outside an all-night car wash. Bugsy was not as they say ‘connected’ but was well known for doing his business without carrying a gun. This night, he was carrying.

The two of them went to speak to the owner of a Model ‘T’ Ford that had just been washed.
“Wanna exchange cars? That Buick for your Ford and $200? You can reclaim the Ford from the parking lot at Union Station in two hours.”

The man took one look at Bugsy and saw that he was carrying a pistol, quickly agreed.
Bugsy gave the other man some instructions.

“Just stay here for a couple of hours and then drive the Buick to the Station and do the swap. If it is still there tomorrow, then it is yours to keep.”

---

Ten minutes later the two of them abandoned the car as promised on an empty lot close to the Train station. Then cool as a pair of cucumbers they walked through the station and boarded the late train to Indianapolis. They were just in time as it was about to depart. An employee had purchased the tickets earlier in the day.

They were seen walking towards the train by a man in the pay of the Department of Justice Agents. Their activities were soon known to the top man. But it was too late and the train had already left the station before the people from Justice could do anything about it.

Agent Ford asked the man who phoned in the report,
“Were they carrying any luggage?”

“No. Just her handbag. It was if they were out for the night.”

The Chief knew that they were running but where would they go without luggage?
He also knew that the train was only going as far as Cincinnati which wasn’t a place where ‘hoods’ like Bugsy went to retire. He was unsure. He wanted to follow but as far as he knew, Bugsy was not wanted for any Federal Indictable offenses. His hands were tied because the Mayor of Chicago had hauled him over the coals for ‘too many innocent people getting killed when the PD had executed a search warrant’. Only the intervention of the DOJ had saved his job. They had taken the heat because of the results that they had had in defeating the bootleggers.

Agent Ford had to decide about what to do next. After a bit of thought, he made up his mind. It wasn’t the decision that he’d liked to have made but Bugsy was a small player in the grand scheme of things.

“We can’t do anything more tonight. Keep his Home and Office under observation and we will raid it tomorrow if I can get a judge to sign off on it,” he told his men.

Still feeling as if he’d let the cat escape he went home to bed.

At that very moment, Bugsy’s HQ was being emptied of everything including the kitchen sink. It was all being ‘donated’ to a bunch of charities around the city. This included several tons of canned food from the legitimate side of their business. Even the access to the other part of the building had been bricked up and the false panel disabled.

---

The Chicago PD and DOJ teams would find nothing apart from a bottle of genuine 1901 Scotch and a note gifting it to Agent Ford. The Scotch had been imported in 1912 and sold at the store owned by the Current Police Chief’s family. The attached receipt from that sale would make a good few people in the city very angry. He’d become a staunch prohibitionist in 1913.

Meanwhile on the train, Bugsy and Stella were relaxing by looking out of the window. Despite the late hour, the train was reasonably busy but they had a little over an hour to kill before the stop in Fort Wayne. Both of them wondered if Ford and his ‘mob’ would be waiting there to greet them? They might just have had time to beat the train but they doubted it.

If there was a welcoming party it would only be the local Police and as there were as far as they knew, no arrest warrants out for them they would not be able hold them for long.

Bugsy helped Stella down from the train and looked anxiously along the platform. They both breathed a sigh of relief when they saw George waiting for them. If the Police had been around here. he would have scarpered before the train pulled in. His being there was a sign that all was clear.

“Good Evening Mr Bugsy, Miss Stella. The car is waiting for us out front.”

“Thank you George. Any problems?”

“No Mr Bugsy. I borrowed this car for an hour from a little old lady. Naturally I made it worth her while. She did drive a hard bargain but she went off happy.”

“Well done,” said Stella as Bugsy held the door open for her to get in.

Ten minutes later they’d returned to the old lady’s house and switched cars.

---

“This car has Ohio plates just as you wanted Mr Bugsy,” said George as he drove them away from the town in the newly purchased car.

“Good. You know where to head for then?”

“I sure do Mr Bugsy.”

“No more of the Mr Bugsy ok. You know the plan.”

“Is sure do Miss Ethel,” said George trying not to laugh.

Two years previously, Stella had found Bugsy wearing one of her dresses when she came home early from an afternoon’s shopping. Once her initial anger had subsided she listened to Bugsy’s reasoning and after a bit of thought, she agreed with his retirement plan. She had a few laughs along the way but there was no good reason why it wouldn’t work.

As George drove east through the night, Bugsy stripped off his male clothes and transformed into Ethel Malone, late of Albany, NY. His boyish features and clean complexion made the transformation quite easy. Once he was dressed, Stella fitted a wig onto his head.

“That’ll do for now… Ethel!”

She said almost laughing.

The next act was for Bugsy’s old clothes to disappear out of the car window into the night. His highly polished two-tone shoes were the last things to go. They signified the end of an era for them both.

Some five hours of driving later George stopped for Gas at the small town of Sandusky, Ohio. The sky to the east was brightening heralding a new dawn. The extra light enabled Stella to apply makeup to George’s baby like face. With a bit of work, he looked pretty reasonable. It only had to last for the trip east for the time being.

“Well, Ethel, welcome to your new life. Now are you going to give me a kiss?”

Ethel laughed and kissed her. Ever since he found her abandoned and very dishevelled by the side of a road in West Virginia she’d been his lover, companion and business partner.

Together they’d made a decent amount of money without having to resort to being a bookie or importing anything stronger than beer from Canada in this era of Prohibition and Chicago Mobsters. Now it was time for them to retire. They’d been planning this since the day Stella first set her eyes on Ethel.

George eventually called it a day well past ten o’clock in the morning. They’d just crossed over into New York State to the south of Buffalo. Lake Erie was to their left and Cleveland was well behind them. Ahead, the roads were going to get a lot worse as they skirted the shore of the Lake so a few hours’ rest were going to be very welcome.

As befitted two women travelling together, George arranged two rooms at a small hotel. One for him and one for the two women. The receptionist was a bit suspicious of this Negro man but his chauffeur’s uniform and the fact the Stella was standing a few steps behind him persuaded her that nothing nefarious was going to happen so she let them have two rooms.
As was to be expected, George’s room was over the stables at the back. That suited him perfectly. That way he could keep an eye on the car that was parked right below his bedroom window.

The two women on the other hand had a nice bright room at the front of the building.

It wasn’t long before all three were sleeping soundly. It had been a long day and an even longer night.

---

Just before seven the next morning, George knocked softly on the door to the women’s room.

“Missy Stella, Missy Ethel, are you ready?” he asked.

“Be right there George,” replied Stella from the other side of the door.

“Very well Miss Stella. I’ll bring the car round front.”

A much more confident Ethel led Stella down the stairs and into the hallway of the Hotel just before 8:00am. Stella was smiling. She’d made a much better job of Ethel’s disguise in the daylight.

Stella settled the bill and they left the hotel together.

George doffed his cap at the women and did his chauffeuring bit and held the door so that the women could get in the back of the car.

As they pulled away, they saw that the woman from reception was watching them go.

“How did I do,” asked Ethel.

“Very well. All that practice we did in the Garage really helped,” replied Stella with a smile as they sat back and let George drive.

The trio stopped for lunch east of Buffalo and then headed for their destination of Albany, or rather the small town just to the east that was appropriately named ‘Troy’. This would be the ‘girls’ home for at least the next year.

It was quite late in the evening when George turned the car off the highway and started up the half mile track that would lead them to the cabin that Stella had bought more than a year earlier. She and Bugsy had made a little side trip on their return to Chicago from New York. They’d taken the Buffalo train and alighted in Albany. As it is the State Capitol, there were plenty of comings and goings by strangers so they’d blended in perfectly.

Three days later the property was now owned by a dummy company that had been setup just to buy the property and pay the taxes on it. Some swift legal work aided by some extra greenbacks moved the process along nicely so that by the time they left Albany bound for Chicago, the property was all theirs. George had visited a few times to stock the place and make sure that there was a really, really good wood pile ready for winter.

Over the course of the next three days the girls settled in to their new home. Stella went with George to do some grocery shopping and to get to know the local area. The very quiet location of the property meant that their nearest neighbour was more than a mile away. The remoteness also meant that they could be snowed in for weeks if there was a big snowfall. This suited them perfectly. The aim of the next weeks and months was to turn Bugsy into very passable woman and that included his voice.

---

On the morning of the 4th day, Stella and George drove over to Rochester where she sold the car and bought something a bit smaller and more befitting to a couple of ‘spinsters’ living alone. Once back in Albany, she said goodbye to George and put him on the bus to New York. In a few days, he’d be in New Orleans with enough cash to setup a Jazz Club in the city. This had always been his dream and he’d been more than willing to work for Bugsy in return for a decent salary with which he bought Gold. Most of his stash was already buried in a swamp somewhere in the ‘Delta’ but he had almost a quarter of a pound of gold in a money belt around his waist when he stepped onto the bus south.

“Thank you for everything George”, said Stella as she said goodbye.

“No thank you Missy Stella. We has had some good times eh?”

Stella laughed. George was already starting to revert to his home town accent.

“We’ll come and look you up in a couple of years but you be sure to write now?”

“Yes Missy. I’s gonna write you real soon.”

With that, he left her and took his place at the very back of the bus as was expected of someone with his colour of skin.

Stella watched the bus draw away with mixed emotions. George had been a key member of Bugsy’s team. Now it was all broken up and there was just her and Ethel left to face the world.

As the days went by, Stella drilled Ethel in the art of being a real woman. With a lot of patience on her part, he started to actually sound like a woman. Everything seemed so perfect at their little hideaway.

But elsewhere the storm clouds were building up rapidly.
The Autumn of 1929 saw that storm hit with a vengeance, and the world changed forever when Wall St crashed.

[to be continued]
[authors note]
Here you have it. The first part of my story set in prohibition era USA. It seems to be period that is almost ignored in Transgender Literature at least here. Please let me know if I have made any major blunders with the timelines.