Date Night with a Femboy (Short) (Patreon)

I rub my sleepy eyes as I stumble off of the sofa and start the long trek toward the front door.  The doorbell had woken me from the best damned nap I’d had in a long time and I was none too pleased at the interruption.  Just my luck, it was one of the maid’s off days.  Another few years of my current trajectory and hopefully I could afford some live in help to deal with this sort of shit.  Who in the hell could this be in the middle of the afternoon on my one hard-earned day off of the week?  In just old sweat pants and a plain white tank top I scratch my stubbly chin then let rip a ripe fart at the door just before I pull it open.

“What?”  I grumble.

Standing on my porch is a slender dapperly dressed gentleman in shiny brown leather shoes with matching belt, slim fitting and crisply pressed blue trousers, a white silk collared shirt, and a snug brown vest around his lithe torso.  His fair lean face was clean-shaven, with strikingly delicate features, and his wavy sandy brown hair came down to just above his narrow shoulders.  His large bright eyes were the most unique shade of pale mint green that I’d ever seen, unique and yet I swear I’d seen it somewhere before.  In the driveway behind him is parked a zippy little hatchback that matched well with his petite wimpy build.

“Hi.”  The little dweeb says in a way too chipper tone.

“Listen fuckface.”  I grumble.  “If you’re here selling God or whatever…”

“God!?  Oh no!  No, no, no.”  He laughs, his laughter light and breezy.  “You don’t recognize me?”

I rub my eyes again and squint hard as I study him anew.  All at once it comes to me, those pale green eyes being the key.  “Shit.  Toby?”

“Hello Raymond.”  His pink lips smile to reveal perfect white teeth.

I stand there a moment just looking at him in bafflement.  What in the hell was he, the neighbor kid from my childhood and one of my little brother’s friends, doing on my doorstep after all these years?  He better not want fucking money.  Jesus, since I’ve been making real dough I’ve been dealing with these poor ass bitches coming out of the woodwork enough already.  I was doing well but I was hardly the multi-millionaire everybody seemed to assume I was.  Based on his fairly new car and nice clothes however it didn’t appear that Toby was hurting in that way.  I rustle my short sleep ruffled hair as I try to make sense of this.

“You tryin to track down Ian or something?”

“Oh no.”  He says.  “I still speak with him.  No, I’m here for you.”

“Huh.”  I grunt.  “Well…what?”

Without a word he pulls his phone from his back pocket.  He opens a series of photos and passes it to me.  I look at him like he were nuts.

“What the hell?”

Silent and with a strange smile flitting about his lips he just stands and waits.

“I’m not gonna…oh hey!  Hot girl.”  I snatch the phone from him and take a closer look.  

He chuckles softly.

Hot girl was an understatement!  Long, lean and luscious the blonde in the photo was a perfect ten, from what I could tell at least as it cut off at the nose and over her face she on had a black face mask.  Damn pandemic!  With her back turned to the camera she had on a skimpy bikini which showed her firm flawless ass and smooth creamy skin beautifully.

“Fuck dude, nice.”  

His smile brightens.  “You really think so?”

“Fuck yeah.”  I go to hand it back to him.  “But why are you…?”

He holds up his hand.  “There are more.”  With his eyes he draws me attention back down to the phone.

“Alright.”  I say.  This was weird as fuck but I wasn’t about not look at a cute chick.

I flip to the next picture to find a drop dead gorgeous red-head in a slinky silver night gown.  Holy shit!  She was as hot as the first one!  Lacking in the chest department but itty bitty titties never bothered me at all.  Truth told, I preferred them.  The exquisite curves and those long elegant legs woke my cock up from a dead start.  Again this woman had on a mask and again the picture was cut off above the nose.

“Do you know these chicks?”

“Mmm hmm.”  He nods.  Folding his hands down in front of him he prods me on.  “There are more.”

“Oh my Gahd!”  My eyes bulge at the next one.  From knees to shoulders in a lacy negligee this gal was posed with one hip thrust out the side to accentuate the smooth curve of her hip.  Her supple thighs pressed tightly together to hide her muff as the snug sheer panties would have shown it all by themselves.  “Fuck, I’d love to rock her world.”

Toby giggles.  Giggles!  What kind of grown ass man giggles?  As much a sissy as he ever was it seems.

I keep going.  Photo after photo I am treated to an dizzying assortment of smokin hot babes.  There was no nudity in any of them but they were as hot as they could get with clothes still on.  They are all of a similar type.  White, small busted, and slender; like most catwalk models that you’d see in a fancy fashion show.  Did Toby work in that industry or something?  While the women were of a top tier professional standard the pictures themselves were clearly amateur.  Another commonality between the photos was that the face was never once seen.

“Hey…these are all the same chick, aren’t they?”

“Can’t fool you Raymond.”

Having gotten to the end I pass him back his phone.  “Well she’s hot.  Doesn’t explain what the fuck you’re doing at my door.  If this is some bullshit ‘investment’ opportunity…”

“It’s not.”  Gripping the phone tightly in his long slender hand he licks his glossy pink lips and straightens up to his full height, about half a foot shorter than me.  “Ian told me that you are moving away.”

“Uh…yeah.”  I say.  “For work.  What business is that of yours?”

Gathering his courage he takes in long breath and slowly lets it out before saying with a precision that told me that he’d practiced this line.  “I am here to ask you out on a date Raymond.”

I blink.  “Excuse me?”

He clears his throat and says again.  “I am here to ask you out on a date Raymond.  Will you go on a date with me?”

“What the fuuuu…”

Toby quickly cuts in.  Holding up his phone he says.  “I can be any of these that you want me to be.  I don’t have to look like this if you don’t want.  I’ve got wigs, make up.  You saw.  You can call me she.  I can go by a girl’s name.  W-we can go where nobody will know us.  Nobody needs to know the truth.  You saw that I can pass.”

“What…are you…?”

“These are me Raymond.”  He waves the phone.  “All of these were me.  And you liked them!”

I recoil.  “I…uh…what?  No!”

“I’ll pay for everything.  I’ll take care of everything.  Just one date is all I am asking.”  He slips the phone into his back pocket and takes a half a step forward.  “Listen.  I couldn’t let you leave without at least…asking.  I had to ask.  I never would have forgiven myself if I didn’t at least try.”

“Try?”  I scoff.  “I mean…I always figured you were hitting for the other team but…why me?”

“Why you?”  He whispers.  “You can’t know how many times I’ve asked myself that question.”

“Didn’t I use to bully you?  Shit, didn’t I kick your ass once?”

“Three times.”  He says softly.  “Slapped me around pretty good.  Busted my lip once.”

“That’s right.  I remember now.  I kept catching you sneaking around our yard.  Around my window.  Little creep.”

A rush of pink colors his fair cheeks.  “Y-yeah.  Yeah.  You did.”  He swallows hard.  “I was a creep.  You don’t know the half of it though.  I…I used to listen at your window.”

“Listen?”

“When…when you brought girls home.”

“Christ!  You were out there jerking off?”

There is a long pause before he whispers.  “Yes.”

“Gah!  You little pervert!”

“I used to wish…that I was them.”

“What!?”

He steels himself and continues with his confession.  “I used to follow you to the swimming pool.  I used to try to stay out of sight in the change room as I…watched you.”

“What the fuck!?”  I shove him hard on the shoulder, causing him to stagger back a step.  To my surprise he steps right back up to me again!  His green eyes locked on mine with an admirable bravery considering our disparate sizes.  This was something he’d worked himself up to and he wasn’t going to let it go easily.

“I went to every game you played in.  I was there to see you throw three touchdowns and lift the trophy.”  He grips at the legs of his trousers nervously.  “I was always so happy when Ian would invite me over, just so I could see you and smell you and just…be around you.”

“You were stalking me!”

“I did Raymond.  I…didn’t know what else to do.  You were the one.  When I figured out I was gay…you were there.  Older, stronger, handsome, so confident.  You caught my eye Raymond.  I was too shy and too scared to do anything about it but…I was obsessed with you.”

“Oh Jesus.”

“I used to listen in when your girlfriends would talk about you.”  He sighs.  “The benefit of being a nerd…nobody notices you.”  

“You’re nuts.”

“You’re probably right.”  His shoulders sag.  “Didn’t you ever have a first crush?”

“If you don’t get off of my porch in the next ten fucking seconds…”  I cock my thick fist back and line him up.

Undeterred by my threat, encouraged by it in fact, he carries on.  “I used to dress like those girls.  In secret.  I’d watch you from my room in your backyard with them and think about how that could be me there with you, joking around and having fun.”  His voice goes softer and lower.  “I thought about how much better I would treat you than they ever could.”  With a slow blink he gazes deeply into my eyes.  “Nobody knows how to treat a man…better than another man.”

I let my fist fly.  Expecting it Toby shuts his eyes and waits for it to land, no attempt whatsoever to dodge or block.  My knuckles stop just a fraction of an inch away from his dainty nose.  What stopped my hand I could not exactly say.  For one…it would be a dirty shame to mess up a face that damned pretty.

He opens his eyes and looks at me inquisitively.

“Yeah, I did have a first crush.”  I say as I pat his lean chest.  “Shit, you really had it bad, huh?”

“I’ve been trying to forget about you for eight long years Raymond.”  He sulks.  “And I can’t.  I just…can’t.”

“I meant that much to you huh?”  My ego cannot help but to be flattered.

“Yes.  If I let you move away without at least saying something I would have always wondered…what if?”

“Yeah.  I know that feeling.  Remember Eve?”

“Eve?  Yeah, I remember.  Principal’s daughter.”

“Yeah, she was mine.   Never worked out but I never forgot her either.  She just had…it, ya know?”

“Oh, I know.”  He lets out a huff and swallows.  Resigned to defeat he says.  “Well…thank you for letting me get that off of my chest.  And thank you for not hitting me.”

“Wait a second.  I haven’t even answered yet.”

“You haven’t…wait, what?”  A glimmer of hope sparks in his mint green peepers.  “What are you…?”

I grin.  “You put out on the first date or what?  I ain’t got time to be messing around with prudes.”

“Raymond…I will suck your cock right now and right here on this porch if you asked me.”

“That’s the spirit!  Date first.”  I wink.  “Then we’ll see.”

“You...you're not serious right now.  Are you?  Are you playing with me Raymond?  I swear to God you’ll break my heart if…”

“Nah man.  It took a fuck ton of balls for you come ask me like this.  I respect that.”  I gently pat his smooth cheek with my heavy hand.  “And those pictures sure as hell didn’t hurt.  Damn dude, you got it goin on!  Whoooeeee!”

He laughs, hardly believing his ears.  “Y-you’re serious!  You’re actually going out with me!?”

“Hell yeah.  Why not?”  I say.  “And just so we’re clear, I’m taking you out.  Not the other way around.  I’m old fashioned.  My dates don’t pay for shit.  No splitting checks and no argument.  That’s just how it is.”

“Uhhh…alright.”

“And none of this girl’s name bullshit either.  Toby’s a good name, wear it.”  I say bluntly.  “If you’re gonna be a femboy…be a fucking man about it.”

His face lights up into one of pure exuberant joy.  “Where!?  When!?  What are we going to do!?  What should I wear!?”

“I’ll let ya know.”  I say.  “Ian’s got your number.  I’ll be in touch.”  I take one more long slow look up and down his slim sexy body, appreciating it in a whole new way, and suck in through my teeth.  “Daaaamn.”

He laughs and starts to back away.  “O-okay then.  I’ll be waiting for your call.  Thank you!  Thank you Raymond.”

I close the door and turn around…then pump a celebratory fist in the air.  “Fuck yeah!”

Part 2