Date Night with a Femboy: Part 3 (Patreon)

The poll for what kind of date this was ended up being an exactly even split!  lol  I'll do my best to combine the two ideas.

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I open the passenger door of the Ferrari like a gentleman then cop a feel of the smooth curve of his hot firm ass like the scoundrel I really was as he passes by.  He lets out one of those absolutely bewitching giggles of his at my touch then sits in the car looking as proud as a peacock.  I strut around the front and get in the other side.  I am just about to start the engine when he grabs my hand to stop me.

“I forgot my hand bag!”  He says in his naturally effeminate tone.

“Forget it.”

“I need it.”

“Forget about it babe.”  I assure him.  “Like I told ya, I’ll take care of everything tonight.  You don’t gotta pay for shit.”

“It’s not the money.”  Lowering his voice to a whisper he confesses.  “It’s…it’s got my condoms and lube.”

I look at him for a long silent moment, admiring the way his cheeks gradually brightened with a lovely pink blush as I let his words sink in, then say.  “Go get it.”

He smiles and hurries up the walk to disappear back through his door.  A fat middle aged couple who had seen our walk to the car are strolling down the sidewalk down the other side of the street give me a pair of bright smiles.  I got the sense that the pair knew Toby and the wife looked generally amused at the sight of their neighbor going on a date dressed as he was, in the husband though I see the telltale glint of jealousy in his eyes.  Sorry pal, get your own damn femboy.  I shoot them back a nod and a smug grin of my own as the pass then wait for my date to return, damned if I was going to hold the door for him a second time but I do reach across to push it open as he approaches.

He hops in, handbag clutched in his slender hands, and closes the door.  “Thanks.”

I wink as the deafening roar of the engine rattles the neighborhood.  I put it into gear and squeal out onto the street.  I drive fast, as I usually do, and Toby gives me none of griping of ‘look out’ and ‘be careful’ comments of my usual dates.  That blissful smile on his face made me think that he wouldn’t be that bothered if he died in a fiery crash right now.  Either he was too besotted to care or he just wasn’t a pussy when it came to aggressive driving, either way we both enjoy the drive.

I find myself sneaking peeks over at his shapely legs and the lean graceful contours of his body and the delicate perfection of his incredibly effeminate face.  What I saw…I liked.  His body was top shelf hottie material and that dress showed off what he had beautifully.  It was so hard to believe that this was my brother’s quiet nerdy friend beside me.  Had I not known better I would have sworn he was a chick.  Toby didn’t just pass, he passed with flying colors!

As often as not I catch him checking me out as well.  Even more than his amazing looks, the way he glanced back at me that had my engine revving as high as the Ferrari’s.  He wasn’t admiring the car or my designer suit or any of the glittering bling, it was ME that he yearned for.  We could have been driving anything, going anywhere, without a dime in our pockets, and I think he would have been just as happy.  The only thing that mattered to him was that he was here with me.  Had I not tugged him off before we left I had zero doubt that lovely gown of his would be sporting a tent right now.  It was a look so pure and so honest that it left me a bit shaken.  I’d never been anyone’s lifelong crush before…and damn did that look make the old male ego feel good.

I hit the freeway and weave through the other traffic as if they were standing still.  An old 90’s era Vette tries to give me a run but we quickly leave him the dust too.  Toby laughs as he watches the bright yellow sports car recede in the mirror, his pale green eyes shining with exhilaration.  Had I known he liked this I would have booked some time at the track.

As we go awareness of our destination begins to dawn on my date as he recognizes some of the sights of our old neighborhood.  As I pull off the freeway and into the familiar streets and alleys of the area where we grew up he looks to me curiously.  With just a sly smirk I drive on, at a more reasonable speed now to fit with the slower, quieter rhythms of this middle class neighborhood.  Despite the time that had passed since either of us lived here the area is still well known for both of us.  My folks still lived in the old house and I knew that his parents were still right next door.

“Why…here?”  He asks in a tentative voice.

“Why not?”  I say.  

“People know us here.”

“Is that a problem?”

“Well…no.  I just thought that you’d…I dunno.”

“I guess you thought wrong.”  I say.  “We’ve got a reservation at Umberto’s.”

“Umberto’s?”  He giggles.  “Really?”

“If it makes you uncomfortable being here I know a great place downtown.  I know the owner, no trouble at all getting a table.”

Sitting up taller, prouder, and taking in the old sights he smiles.  “No, this is fine Raymond.  This is just fine.”

“Good.”  I smile too.

In the context of the wider world Umberto’s was a quaint old fashioned Italian eatery, classy but indistinguishable from so many others throughout the country, but for this neighborhood it was as good as it got for fine dining.  It was THE place to go.  The kind of place for a working man to dress up and take his wife for an anniversary or birthday.  I could have taken him anywhere but for this one night I wanted to make his dreams come true and those dreams were rooted right here where we grew up.

Windows down we casually cruise down the main drag taking in the sights and smells and sounds.  We see old faces and new but the overall vibe of the place hadn’t changed a bit.  It all brought back so many memories.  How many dates had I done this with back in high school?  Two dozen?  Three?  I’d lost count.  My current wheels were a huge upgrade on my old ZX and my stunning date outshone the teen hotties I used to cruise along here with but otherwise everything felt just the same as yesteryear.  It felt…nice.  Like a homecoming that I never realized I needed.  I could tell already that tonight was going to be something special.

Along the way we turn many heads.  Driving a car like this a neighborhood like this was sure to draw attention.  A few old acquaintances recognize me and wave and I nod back politely.  I wasn’t sure how many recognized Toby but I knew his unique eye color would quickly clue people in despite his incredible transformation.  We had announced our entrance.  Near the end of the main street I find a place to park and pull in under the shade of a pair of arching oaks.  I shut the engine off and all goes quiet.

“This isn’t Umberto’s.”

“Reservation isn’t for a bit.”  I say.  “I thought we’d take a stroll first.”  Taking out my phone I power it down.  “Phone off, devices off, no distractions.  You’re all mine tonight Toby.”

He lets out this cute trembling breath before nodding enthusiastically and doing what I asked without protest or excuses.  In recent years that simple request had become a bit of a stumbling block on many of my dates, not so with him.  I liked that.  Getting out of the car I go around to open his door.  I offer my hand and he takes it with a bashful smile and allows me to help him up out of the low seated car.  Everything about that simple act was so effortless with him.  He got it.  He understood how nice it felt for a guy to be able to act the gentleman.  I liked that too.  He stands with natural poise, looking every bit like a runway model, as I close the door and offer him my arm.  He takes it and clutches in tight beside me, waiting and willing to follow wherever I lead.  I really liked that.

This part of the street is calm, just the gentle rustle of leaves in the evening breeze drifting around us, but up ahead we can see the area we’d just driven through had the usual hustle and bustle of a Saturday night.  Our date was about to begin.

Part 4