A (Re)New(ed) Plan

Sebastian blinks, processing the statement before a slow grin spreads across his face. "Wait, are you serious?"

"Dead serious," I reply, trying to keep my excitement in check. "I mean, if she's a lesbian, maybe approaching her as a woman will give me a chance? Think about it!"

"I am, how did you come to this conclusion, or better yet, that I could help you?" His tone is measured but stilted, how how you would talk to someone clearly insane.

"My method wasn't wrong, I knew that being willing to change for a girl was the sign of true love, all the movies said so, but I completely missed the mark on how I should be changing."

"And how would me Fucking you help with that?"

"What!?"

"Well what else do you mean by, 'Make me a Woman'?" He started to settle down, like he was worried I'd try to jump his bones or something at first.

"As in, look and act like one...wth man."

"Hey you're the one busting into the room all crazy eyes. Who knows how that mind of yours works, again why do you think I could help you in any way?"

I tactfully choose to ignore the negative parts of that and push forward. "Because you were in theater in high-school, that means you know how you act and cross dress right?"

With a long suffering sigh, and a muttered are you fucking kidding me, "and which movie taught you that stereotype?"

"I don't get all my life lesson from movies-"

"Thank fuck-"

"- I learned that one from anime!" I smile at my resourcefulness, 'and the judge was worried not having a mom around would leave me emotionally stunted I showed her'.

"Of course you did..."

"So when can we start?"

"What? No I'm not going to help you humili... you know what sure buddy, I totally know how to help you."

" Great! you're a great guy, you know that right?"

"Yes, yes I am, now lets get you started, and sense you like movies and anime so much I have home work for you while I make a plan, for this shit show..." He mumbles the last part as he opens his laptop, "Look up some movies with 'cross-dressing' and 'for women' as key words, go ahead and do the same with some anime, I'll have something ready for the weekend, I'm sure you'll blow her socks off."

'I know he meant it sarcastically, he plans to try to scare me away from this plan somehow, but this plan is perfect, fool proof really.'

Hopping on my bed, plug in my headphones and pull up some movies and blush at how many of them are porn adjacent or just porn.

I push down the awkward vibe and push ahead, no porn is going to stop me!

The week passes in a blur of poorly chosen movies and even worse anime.

By the time Saturday rolls around, I feel like I’ve learned a bunch, nothing good, just that I'm about to put myself through the wringer—but I’m more determined than ever. I stride into our dorm room, ready to see what Sebastian’s come up with.

Sebastian looks up from his laptop, a wicked grin on his face. "You ready for this, buddy?"

"Absolutely," I reply, brimming with confidence. "What’s the plan?"

He gestures to a pile of clothes on his bed. “First, we get you dressed.”

I eye the pile warily. “Uh, what kind of clothes are we talking about here?”

“Something that’ll help you blend in,” he says, his grin widening. “Trust me, this is exactly what you need.”

I reach for the top item, and my heart sinks. It’s a frilly pink dress, straight out of a bad anime. “Sebastian…”

“What? You said you wanted to look like a woman. This is what 'we' do, right? Why you asked me? To teach you to 'Play the part' like us theater kids?”

“I meant, like, subtly!” I protest. “Not… this!”

"How would I even do that subtly?" Sebastian chuckles, clearly enjoying himself. “You want to win her over, right? Then commit. Put that on, unless you're ready to admit this was all a bad idea?"

At the hopeful sound of him wanting you to back down the spite rises up and reinforces you previous positive mood. "I would never admit that."

"Which is why we're here."

'There's that long suffering sigh again.' "So are you going to turn around and let me change or what?"

"Sure, sure, not sure why you care, I've seen you change before and vis versa."

"Dude, cause I'm a girl now."

"Sure buddy. Done yet?"

"Almost.. just gotta get ... there we go, how do I look? Hot right?"

"Sure, now finish so we can leave."

"Finish? Leave?!" I ask, picking up the shoes and under wear.

"Well yeah, need to have you 'preform' in front of people, can't do that with only a dress, or where you just going to only 'be a girl' when around her? Do you think she would really go for that?"

"No?"

"Right... well lets get going girl, we are going to a club that's a bit of the beaten path so you can figure things out without anyone else you know seeing it, just yet."

One awkward walk to the car, takes us to a club I didn't know was in the party town next door to the college, "Club Three Dollar? Never even heard of it."

"I bet you haven't, its a queer bar."

"Why?"

"Well you want to win the heart of a lesbian, can't do that if you can't even get the number from one in there. Go get them tiger! Unless you want to bail?"

Being here, nerves flaring as what I signed up for becomes more real. I slowly get out of the car. Determined but shaky "Ok, I got this, no need to bail. You coming?" I ask the last part because I notice that in the eternity it took me to get out of the car, he's not even turned the car off.

"Nope, I'll be back later."

"What?!" Is all that escapes my mouth as he speeds away.

'Fuck, guess this is it, do or die, I got this!'

Two hours later and sitting outside.

"I don't got this." 'I can't believe I forgot my phone, who makes a dress without pockets... who buys someone one and doesn't also get a purse big enough to fit one?!'

Its only a little bit longer before Sebastian pulls back in.

"Make any progress?"

"No. Sorta? Also fuck you."

"Really?"

"Yeah, I left my phone cause I didn't have anywhere to put it!"

"Girl clothes 101 really, you should be thanking me, you'll never take things like pockets for granted."

If I was a cartoon I'd have steam coming out at this point. "So noted..."

"But what did you mean by sorta?"

"Welp... no one gave me any numbers, got a few less than rude rejections tho, one even came with advice."

"Oh?"

"Yeah, 'Sorry honey but a beard is really a turn off for me'. So I guess that's something, did have one guy hit on me... So there is that?"

"Really, how did that make you feel? The guy thing."

"Felt nice but also weird, after all those rejections it helped?"

He nods his head, absorbing that tidbit. "Still want to keep trying or ready to give up?"

"Nopppe." I pop the P just to be annoying, "Shaving's not the end of the world and really, they were all nicer than I expected."

"You got it champ. Going to have to pull out the big guns."

"What?"

"Nothing, just working on helping you out. Uh, this week work on shaving I guess, I'll have some more stuff to help you by next weekend, we'll try again."