First off I love this idea.
But imagine how it all started, maybe Bucky did go out on a date with a girl and Steve got heated. Bucky tries to smooth things over and tells Steve it isn't like Steve could just become a woman. But gives Steve a wild and far-fetched idea.
Steve already knew he was pettie, he was smaller than his own ma for goodness sake. So sneaking into her closet one day while she was at work, wasn't all that hard. Finding a dress that fit was even easier for Steve.
Imagine Steve not telling Bucky about the idea until he has perfected his girl form. Bucky almost caught on a few times when Steve's voice was way too high-pitched, but Steve played it off as asthma, which of course only made Bucky worry more.
Then Bucky invites Steve to some technology convention and it was just going to be them. Bucky wasn't interested in trying to find a double date for me. But the surprise on Bucky's face when he knocked on Roger's apartment and a young woman opened the door. She had brown shoulder-length hair, a gorgeous navy blue dress on, red lips, and red heels.
Bucky short-circuited for a second before he heard Steve's laugh leave the woman's lips.
Now there was excitement because the outfit was so convincing and Bucky was beyond excited to be able to take out his lover without all the attention.
Bucky spends some of his paychecks on makeup or new outfits for his Dot. Which honestly became a persona for Steve. Dot was a little more sassy and brattier than Steve and it drove Bucky wild.
It was also impressive how much Steve's makeup skills improved over the short time, but they were constantly going out because Bucky constantly wanted to show off his dame.
Post-Serum was a different story, Bucky would tease Steve when Dot's personality slipped out, but Steve didn't have the supplies or time to dress up as her anymore.
Then once they were both reunited, it would still take Steve time before they brought up Dot again. It wasn't until Bucky saw Steve's Instagram feed over Steve's shoulder and saw Steve was watching how BodyBuilder women liked to dress to feel (more) feminine or how the next post showed a woman with huge muscles in a cute dress and not caring what society thinks. That's when Bucky realized that maybe Steve missed being able to dress up as Dot.
So Bucky goes to work finding different clothing, styles, and wigs before presenting it all to Steve.
"Would you be interested in being my Dot again?"
The small smile on Steve's face made it all worth wild.