Viola and Olivia -A Straighter Tale That You Might Think-

Based somewhat on Realiations of a Countess by The-Fluff-Master1882

A/N: Welcome to another round of Shakespeare what if's in today's episode we have: What if Viola never had a twin brother? And was trans? And may or may not be a time traveler!?

"I left no ring with her, what means this lady?" Viola stood dumbfounded outside Olivia's estate pondering what the beautiful girl had been saying.

"She loves me sure, the cunning of her passion." And Viola loved her too, though she knew that she could never marry her because that'd be gay.

"But if I am man?" She must admit, she really loved being Cesario. It's like Cesario was who she had always meant to be.

"What thriftless sighs shall poor Olivia breathe!" If Olivia ever found out about Viola being Cesario and not a real man she'd certainly not marry. But if she could just pull off the act well enough… No that would never work.

"Oh time, thou must untangle this not I, it is too hard a knot to untie."


Olivia sat in her garden thinking. She loved that boy Cesario, and while she knew that it had been stupid Orsino who'd sent him she couldn't help but be glad that pompous sole had brought him to her. She had spent so much time thinking and monologuing and avoiding people with yellow socks those past few days, that she finally made up her mind. She would confess her love to Cesario on his very next visit.

Viola looked in the mirror in disgust. The innkeeper of the hotel she was staying at had given her extra dresses to wear and out of politeness. But she hated being a girl. That was it, she rushed into the back room of the inn and grabbed a pair of scissors that then pounded back to her room. In one swift cut she chopped her hair so short that she'd surely be taken as a boy. That was it. No more Viola.

Cesario nervously took Duke Orsino's letters and put them in his bag, ready for yet another delivery. They were so painful to deliver because even though Cesario had a major crush on Olivia he couldn't stand watching her be all love-y around him and yet being talking about Duke Orsino and not him. But he manned up and told himself anything was worth being around Olivia. He opened the door to Olivia's room and saw the girl already smiling at him.


"Who goes there? Is it true that my churlish messenger hath returned once more?" Olivia smiled slyly, she knew it would be Cesario.

"True that is, Lady Olivia." Cesario said nervously, "Your papers, madam." He stuck the letters from Duke Orsino out towards her.

"Why thank you, but really must we waste time with those ruthless wails of scurvy pathetic 'love'. For I wish to be with you Cesario." Olivia said gracfully

"Why, why thank you o sweet Olivia but I, I… My master's word, I vowed to -" Cesario stuttered "Look, I'm sorry, I can't keep this shakespeare talk any longer. Lemme just explain to you my deal, then you explain yours and then we'll like, ya know, figure something out alright?" Cesario said

"My dear, your beautiful language! It's so exotic; please, I pray you, continue!" Olivia said, loving Cesario even more.

"Well, um ok, so here's the deal. I got a job from this dude Duke Orsino or whatever and he likes you a heck of a lot. So my job is to send these love letters to you. My job is to make you fall in love with him. But uh, you're falling in love with me instead. Sooo… yeah, that's my deal, and your's is I'm guessing I love you so much and that other guy sucks right?" Cesario finished

"If I do understand your word, my love, then yes, I do love you more that the stars love the sky." Olivia breathed.

"Alrighty, so that's great for you but, if the Duke finds out I'm not doing my job, then Imma get fired." Cesario admitted sadly

"Ah, what a rascally and elvish pickle we've found ourselves in yes?" Olivia sighed, "But to my suspicion I do believe there'st something you do hide from me." she said.

"Well, yeah, but um, ok one…. I love you." Cesario paused to take in what had just happened, "There, I - I said it. I love you Olivia, I love you a ton, like how ever much you had said -"

"More than the stars love thy heavenly sky?" Olivia finished.

"Yeah more than the stars love the sky," Cesario said "I mean you've witty and really pretty and man, I just - I love you a lot."

"Ah what love's perfection we hath met here tonight grace you gods and faeries whom hath blessed this night sky." Olivia said

"Yeah but there's another thing. See, I kinda used to be a girl…" Cesario said

"By what measure have you womanhood? Ha! What elvish humor had been played now?" Oliva lauged

"No really, I like, used to be a girl, and even though I look like a guy I used to -" Cesario stopped, realizing there'd be no good way to explain such a thing to the sheltered aristocratic girl, however much he loved her nothing would work.

"You look as much a man as Orion or Zeus himself! You cannot be such a thing. Unless perhaps you be a faerie!" Olivia said in delight. Cesario gave up, if this was going to work, it would work.

"Yes, I am a fairy, and I am a tricky fairy that looks like a boy but also a girl ok?" Cesario said

"If I do understand your words so, then 'ok' shall it be," Olivia said, "but there is one thing I must ask of you, faerie Cesario." And with that Olivia wrapped her arms around the boy and kissed him. Cesario had never been kissed before but needed no further explanation, he kissed Oliva back and the two snogged for a whole minute before falling onto Olivia's bed to explore other things.


Hours later one of Olivia's servants finally knocked on the door. Embarrassed, Cesario tried to hide, but Olivia promptly settled everything.

"Maid, this is Cesario. He and I shall be wed 'morrow's eve. And do tell that toad-witted Orsino to query his love elsewhere. Now please, scuttle along, for some of us have important matters to attend to." She said and the maid quickly ran off.

"Now where were we?" She asked her lover, laughing, and the two kissed passionately; crashing once more on to Olivia's bed.