The Best of Friends (TG,TS, Sissification, MC)

Prologue: A Midsummer's Night

Two men sit on the back patio steps of a dingy row home, a study in contrasts; one a bald burly bearded fellow of average height dressed in what could charitably be called ‘First Date Casual’ and other a smaller, short slender blonde guy in a polo and shorts. The bigger man,Caleb, and the shorter, Evan had been roommates since the end of the school year in May, two months prior. Both men were in their thirties, had comfortable jobs(Caleb, programming and Evan, teaching) and could live on their own, uncomfortably...but between the housing shortages and inflating costs, it made more sense to live together.

A loud crash disturbs the summer evening's air, glass rebounding off the heavy duty plastic of the recycling bin.

“Hey Evan hand me another out of the cooler, would ya?”

Evan reaches into the icy depths of the cooler and grabs another brown bottle and passes it over then goes back to contemplating his own glass.

Cracking the cap, Caleb takes a swig and leans onto the door-frame. “You know, I really thought I had a chance this time, Amy and I had been chatting for like a week on Bumblr and thought things were going well, shows how much I fuckin’ know! Completely ghosted!”

“Hey, at least you got that far! Pretty much everyone goes ‘Eww, 5’5”’ and swipes left. I haven't had a date since sophomore year with Katie Wagner…”

“Wait, Katie, I don't remember a Katie Wagner. Sophomore year of College or High School?”

“High School…” Evan mumbled dejectedly.

Caleb clamps his hand on Evan’s shoulder. “Oh my dude, I'm sorry, that sucks…I can't even imagine what It’d be like to not have a date in 15 years. Worst I've had was the five years after She-Who-Shall-Not-Be-Named cheated on me. Does that mean you’ve never actually had a long-term relationship with *anybody*?”

Evan swiftly chugs the last of his beer and pours himself another, clearly stalling for time.

“No, it just, y’know, didn't seem like it was *that* important in High School and in College I was either having fun hanging with y'all on the weekends or studying for my exams. I always figured I'd find someone out in the “real world” after College, but being a Teacher is a special hell all it's own, not to mention dating apps like Bumblr and CupidFish kinda feel like a Gatcha Game where you pay to win and I don't have the right currency.”

“Special Hell? What do you mean, I've seen some of the teachers at your school and they range from cute to Grade-A Gorgeous, pun definitely intended. Oh…Oh shit you mean you got put on ice?”

“Yep, I'm either a non-sexual entity or they don't even see me as someone worthy enough TO date.”

“Fuck dude, we gotta fix this. Relationships are great, and I’d hate to think my buddy never got to experience one. But I gotta ask, do you *just* like ladies? Maybe that's the problem, perhaps you should broaden your playing field instead.”

Evan collects himself, takes a deep breath and an even deeper swig. “Well, I never really told anybody this, especially cuz my parents would probably kill me but I guess I'm bi. I do like some guys but I've never done anything beyond looking. Hang on though, why are you telling me to broaden my playing field if you aren't? You’ve only dated girls haven't you?

Caleb chuckles, then takes his own swig. “Nah man, I'm FINsexual. Means I’m romantically and sexually attracted to anyone feminine in nature. Cis Women, Trans-women, Cross-dressers, Fem-boys, and uh, Female-Presenting Non-Binary folks. Basically if they look like a lady and act like a lady, I'm there. Remember Alina?”

“Yeah, your girlfriend you had during the lock-down years? She was kinda cute…what happened there?”

“Yeah she was. Turns out I was the first guy she had ever dated before or after she transitioned and turns out that while she was attracted to me romantically, sexually she was really more of a lesbian, which I get, ladies are hot. Still friends, more or less.”

Caleb rubs his beard and looks pensive.

“Hey Evan, I never did ask, but what does your ideal partner even look like? Guy, girl, gender fluid?

“Umm, well, I’d like someone a bit taller than myself, long blonde hair, slightly tan, blue or grey eyes, full lips and a bright smile, maybe C-Cup breasts and long legs. Someone who's energetic, happy and kinda fit. Caring but definitely not naive or dumb. And…maybe you know, a penis, just because I've never knowingly met a person that's…in-between like that. How about you?”

“Me? I like all kinds, but if I'm getting to pick…to quote the inestimable Knight himself ‘I like real thick and juicy. That when a girl walks in with an itty bitty waist and a round thing in your face, you get sprung!’ So a curvy hourglass, but to deviate from Sir Mix, I kinda like ‘em with a little bit of fluff in the belly. Dark wavy hair, Latin features, full lips and a smile to die for. I don't mind if she's shorter or taller than me, but I do like to kiss ladies on the forehead and I ain't THAT tall. As far as personality, I'll take the caring and cheerful, but if she's got enough sass to banter with, that's even better.

Evan laughs at the old reference but contemplates Caleb’s choices.

“Wow, she sounds amazing. Quite the lady, I don't know if mine even compares to that."

Caleb takes another swig and considers the image of Evan’s ideal partner.

“Yours sounds sweet and lovely too, man. Beauty is subjective and if your girl showed up at the door I wouldn't turn her away just because she wasn't my ideal. On the subject of the down below it definitely can take some getting used to, but hey, you almost always know if they’re in the mood, though hormone therapy and meds can mess with that. Just gotta be careful, because trans ladies and non-binary folks with a penis may not always have the best relationship with, err…their factory equipment. Always make sure you ask. Alina didn't mind oral but otherwise she didn't want to do anything else with it, total bottom.”

Evan’s eyes widen at the casual mention of Caleb’s escapades. Then he starts to chuckle nervously.

“Wait, so you went down on her penis? Multiple times? Hah… that's pretty damn not-straight, you know that right?”

Storm clouds begin to gather on Caleb’s brow and his tone turns cool.

“Evan, I know yer basically The 30-Something Year Old Virgin, but goddamn dude, you need to get your shit straightened out. Alina was a trans lady and the definition of straight is being sexually attracted to the opposite sex. Ergo, straight. Also, that’s kinda rich coming from someone who outed themselves as bisexual tonight and admitted to wanting to play with dick naught but a couple minutes prior. Also, pro-tip? No self-respecting gentleman turns down the opportunity to please their partner if they're cool with it.

Evan visibly winces, then drains his beer.

“Sorry sorry, didn't mean to step on a nerve, this has been a night of revelations is all. Speaking of which, I'm heading to bed Caleb, got a School workshop tomorrow morning.”

Evan closes the cooler and tries to pick it up but stumbles over it and sighs.

Caleb guffaws and most of the anger dissipates with it.

“Shit, you do need to sleep, looks like those Pisswater Dubbels hit you hard. Ain't it gonna be Saturday though? I thought school wasn't allowed on Saturday, some immutable law of the Universe or something. Anyway, good night, Evan go drink some water, I'll drain the cooler and take it in. And I promise you, I'm gonna get you that date by the end of the week, my dude!”

Evan lets out a small sad laugh and opens the door. “Thanks Caleb I wish I had your optimism, but I appreciate the effort all the same.”

Caleb sets the cooler to drain, then finishes his beer, chucks the bottle in the bin and sits back down on the step with a sigh.

“I gotta figure this out, damn, maybe I can set up a double date with the next person I match with or something…”

Author's note because several people have asked about my Acronymics

• TG refers to Trans Gender(In this case full Gender Swap from Cis Male to Cis Female)
• TS refers to Transsexual (In this case into Cis Male to Trans Female)
• CD/Sissy refers to Crossdressing/Sissification
• UI refers to Unintentional(In this case Caleb and Evan are oblivious to the Program's true intentions)
• NMI refers to Non-Malicious Intent (Caleb uses the Program to 'help' Evan while benefiting himself more)