#then 'ha what if Winston married Sophia' turned into 'ha Oliver is gay what if he liked Winston' | Explore Tumblr Posts and Blogs

hollenka99 · 4 years

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Winston and Oliver

Winston and Oliver have two pretty different upbringings. Winston is brought up by his mother and stepfather in Saint John, New Brunswick, not very well off financially. Meanwhile, Oliver grows up as the son of a successful actor in Los Angeles. It just happened that their fathers had once been best friends, leading to them being childhood friends too. Whenever Oliver's family visited his father's relatives in Canada, Oliver would try meet up with Winston. So, with the help of letters, they remain good buddies.

Still, they start growing up and all their school peers begin developing non-platonic feelings towards each other. Anthony would talk about girls he thought about asking out. Oliver... couldn't relate. Perhaps he wasn't quite old enough. Let's wait a couple years. Still nothing. Okay, God, he's ready to be into girls already. Any time now. Seriously, don't wait up.

Winston is attracted to girls, even has a girlfriend or two during the early 1930s. Yet he feels similarly towards men too. Hmm odd. He guesses it's possible to be interested in both men and women. Who knew?

They were both raised Catholic. However, Winston doesn't suffer internalised homophobia as badly as Oliver does. Over the course of their life, Winston helps him grow more confident with his identity.

Oliver visits his aunt in Saint John during the summer of 1934, preparing to move to New York for college after the holidays. While there, he comes out to Winston. He needs someone to know and he rationalises it in his mind that if Winston doesn't react positively, they can always go their separate ways and leave their friendship behind as a childhood thing. He doesn't want to lose Winston as friend though. Oliver knows he won't rat him out to the authorities either way. So you can imagine the overwhelming relief he feels when Winston smiles and admits he's gay too.

While at Julliard, Oliver befriends a girl name Mary. She falls in love with him and he doesn't have the guts to tell her he'll never feel the same. He loves her but only platonically. Still, he enjoys her company. And well... he's going to have to marry a girl one way or another. He'd rather it be Mary.

Everything about being her boyfriend feels wrong. He's deceiving her. And he's now planing to make that deception lifelong. He really shouldn't be doing this to her. And yet he does, for the sake of selfishly saving his own skin.

Sophia has always suspected her brother was attracted to men. She privately calls him out after he announces he's engaged. Oh and what do you know, she's attracted to 'all sorts of individuals'. Great, that would have been good to know as he came of age. Nevermind. He knows now.

Around the same time, Sophia and Winston start a relationship. After all, Oliver isn't the only Jackson sibling to enjoy hanging out with Winston when they were growing up. They're happy together and Oliver is happy for them. He trusts Winston to treat her well.

Oliver marries Mary in 1940, with Winston becoming his brother-in-law the year after. Things are going well. The two men meet up every now and again. Mary just thinks her husband is spending time with an old friend. Sophia knows what's really going on and doesn't care too much, so long as Winston doesn't see anyone else behind her back.

When Oliver gets the news that two of his brothers have died, it changes how he wants to go about life. They had been 24 and 22. Oliver himself is still 28 by that point. He has some 50 or so years left, assuming he is going to die old. Does he really want to live a lie forever, just so everyone will approve of him? 50 years is a hell of a long time.

Mary unintentionally discovers the truth in 1951. She makes him pack his bags immediately. They divorce on the grounds of adultery. Fearing he'd 'corrupt' their two children (age ~9 and 5), she ensures he sees as little of them as possible.

Unsure of where to really go, he ends up at Sophia and Winston's doorstep. His reputation has been heavily damaged, his career as a composer with it. It feels as if the only things he has left are his sister and his best-friend-turned-lover.

Sophia understands the position she's in. Her husband prefers her brother's company. So she lets them go. She wants them both to be happy. Her only condition is that Winston remains an active part of their children's lives.

This new way of life works quite well for them. Winston moves to New York to live with Oliver. The three Wynton children grow up with their dad living with their uncle every other week being normalised. Their mom bringing 'friends' home every now and again isn't that out there either.

Life carries on, as it tends to do. More nieces and nephews come from Anthony, Harriet and Nora. Oliver definitely feels at home in Winston's company. Winston feels the same.

Still, the two of them have to remain secretive and anxious that they'll be discovered. I can't seem to find what the penalty in the state of New York was for sodomy. Whatever it was, they wanted to avoid it. Being disgraced as an unfaithful husband is one thing. Being in a same-sex relationship during the 50s is something else entirely.

In 1962, Illinois repeals its sodomy laws, essentially decriminalising homosexual relationships. 10 years later, Winston asks Oliver if he wants to move there. All of their children are adults themselves now. Come on, they could be free to be two men in love. Oliver is skeptical. He has built a life here in New York but... not hiding does sound nice. Okay then, let's try life in Illinois.

So they move to Chicago. They take some time to settle in, meeting other local members of the queer community while doing so. They're still not displaying their relationship in public. Decades of being cautious will do that. But then they're eating out with some friends and a couple hold hands. Very publically. And they're not getting any backlash for it. No-one's coming to their table to try get those two arrested.

Winston and Oliver risk holding hands where other people can clearly see them. No major consequences. A while later, they increase the risk by kissing while in public. Again, no legal repercussions.

Oh. Oh shit. They really can be out in public here. They get dirty looks sometimes. But it's not like those people could have them thrown in jail. They're in their late 50s now and finally, finally they can be visibly homosexual.

In 1975, they celebrate their respective 60th birthdays. Their first major birthdays as their true selves. They still can't believe it.

The two of them decide they want to help the younger generation. The queer kids who were coming of age in a time of more freedom. They both grew up in fear of being discovered. These kids need to know the community has their back. Laws changing doesn't immediately change attitudes, after all.

A music store is set up. If someone came saying their friend, Dorothy, sent them, they'd be sent to the back room. Word spread and more arrived claiming 'Dorothy' sent them.

Over the next few years, they watch these teenagers and young adults grow up. Some go to college or move away. Others keep hanging around where they know they'll be accepted.

Then one of the kids they'd said goodbye to returns. Oh wow, it's great to see you. How are things? You and Joshua still going strong? Wait, what do you mean he suddenly became very ill and died? Oh, that's- that's awful. He was such a good guy. We're so sorry. Give our condolences to his friends and family, if you're able.

It's not the last time they have members of their youth club become affected by this strange new disease. Not by a long shot. As the years carry on, they'll have one person coming to them saying their friend was diagnosed. Then they'll have another privately revealing they contracted the disease themselves a while later. Quite a few simply stress about the prospect of potentially getting infected.

Listen, they're just two gay men who are fast approaching their 70s. What the hell are they meant to do to protect these members who were practically children from something this overwhelming?

This disease obviously gets a name. When they hear about the New York Times referred to it as Gay-related immune deficiency or GRID, this ruffles more than a few feathers. Paired with other terms such as 'gay cancer' and 'gay plague', they are livid that the media has decided to target their marginalised group further.

This won't do. The two of them were born in the middle of a huge war where millions of young men died. Winston's father and Oliver's uncle were two of them. Oliver lost two of his brothers to the sequel of that war where even more people died in the millions. Too many young men and women have been needlessly lost this century. Even more are being lost right now but that's obviously not important because of who those people are.

People are dying. Some of them are only in their 20s or 30s. Stop using this as a chance to demonise a community that's already suffered enough, you bastards.

As soon as they learn it is spread through intercourse and infected blood, they promote protection. Boys, here's a condom. Girls, if any of you are planning to become involved with a guy, take one too. Don't expect him to necessarily carry one on him, though he should. And if any of you kids are doing drugs, please stop. You shouldn't be interacting with drugs in the first place but there's no better time to go cold turkey than right now. It would break our hearts to hear you got sick. Please stay safe out there, okay?

The 80s eventually turn into the 90s. While the members of their youth group may have seen them as gay uncle types back in the 70s, they're definitely more gay grandpas now. They keep going, maintaining the store and supporting younger members of the queer community in Chicago.

Oliver dies in 1999, with Winston joining him three years later. They are 83 and 86 respectively. But you know what? They've had a great go of it. Whether it was as childhood friends, brothers-in-law who maintained a secret relationship or long-term partners, they've been at each other's side. They count themselves lucky to have found someone so dear to them and been able to spend their life with them.

They wouldn't have wanted to do it with anyone else.

#the life of jameson jackson #tlojj #my boys #them being a couple honestly started way back when I was still writing tlojj #I wanted Winston to be close to some of the Jackson kids #because of Jameson and David's past friendship #then 'ha what if Winston married Sophia' turned into 'ha Oliver is gay what if he liked Winston'#and... yeah #I love these two #I didn't make them specifically for each other #and yet they love each other as if they were

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