Date Night with a Femboy: Part 4

With the hottest god damned femboy this city’s ever seen glued to my side I strut down the walk of the old neighborhood the exact same way I did the day after quarterbacking my team to the high school championship.  Knowing now how Toby had followed the team that season and was there to watch me and cheer me on as I threw the winning touchdown made me wish that I’d known about his crush back then.  Even though it had been days since he’d asked me out and confessed his infatuation I was still struggling with the fact that I’d had on demand bussy right next door to me all that time and I never had a clue!

As we walk the street gets louder and busier.  Couples, families, and lively groups of friends mingle between the quaint restaurants and other businesses that were the beating heart of this cozy community.  The jubilant mood was upbeat and honest.  Just a bunch of folks out enjoying their hard-earned weekend.  In the circles that I’d been keeping lately fronting and faking was so much the norm that I’d almost forgotten what this was like.

“Isn’t it a lovely night?”  Toby sighs softly as he clutches to my arm and looks West to the amber evening sky.

“Yeah.”  I say with an uncharacteristic warmth.  “It’s real nice.”

The smooth tone of his naturally soft voice, the way he moved with such silky grace, his alluring perfume, the mere fact that he was a dude that used the word ‘lovely’ without irony or shame all worked to bewitch me even more.  Toby, without even seeming to try, exuded a gentle femininity that most women I’d been with couldn’t even touch.  He wasn’t a chick but it was impossible to see him as just another guy either.  He was in this wonderful middle ground that I’d never had to contend with before.  Just knowing who and what he was beneath that flawless female appearance had me going WILD with desire.  I could still almost feel his hard cock throbbing in my grip as he shot his load on his entryway floor.  God that was hot.

“You in the mood for anything?”  I ask.  “We’ve got some time before the reservation.  Dancing, shopping, a drink, you name it my guy and I will make it happen.”

“This is nice.”  He says.  “Just walking with you is nice.”

“Yeah, it is.  Isn’t it.”  I smile.  “It’s been a minute since I just stretched my legs like this.”  I slow my pace.  “So talk to me.  What do you do?  What are you into?  Tell me something.”

“I’m…not really that interesting.”  He whispers.  Bowing his head bashfully he self-consciously tucks that pesky lock of wavy sandy brown hair that kept coming free back behind his ear. “Not like you Raymond.”

If that demure shyness was an act…it was working on me!  Seeing how meek he was out here in public only made me respect what he’d done on my front porch all the more.  The craziest bit was that he seemed to have no idea how fucking sexy his bashfulness was.

He continues in full swoon.  “I saw you in the news heading up that merger deal.  I saw you were made the youngest vice-president in your company’s history.  I read about your donation to the children’s hospital.”

“Ha!  That was for PR and a tax write off.  I ain’t not saint.”  I give him a sidelong look.  “Are you still stalking me?”

“No.”  He smiles.  “Not anymore.  This time it was research.”  His smile brightens.  “I never expected you to say yes to this.  I had to get up to date.”

“Enough about me.  C’mon man.”  I say.  “Talk to me.  Tell me about you.”

He swallows, screwing up his courage, then says.  “I’m a programmer.”

“Like computers?”

“Yeah.”  He says.  

“Anything cool, like CoD or something?”

He giggles.  “No, not like that.  I help create retail systems, pretty boring stuff.”

“Hey, if you like it that’s all that matters.”  I say.

“I…um…”

“Quit mumbling.”  I laugh.  “What?”

“I’m also working on something in my own time.”

“Oh?  Well, tell me.”

He seemed reluctant to spill it and yet I could see the passion blossoming in his eyes.  “It’s an gardening app.  It tracks length of day, temperature, cloud cover, precipitation, and a bunch of other things.  It takes into account what direction your garden is facing, your soil type, and the amount of shade.  It’s got a database with over a thousand common plants and their ideal conditions.”

“So what?  It tells you when to water or something?”

“Yeah, and so much more.  It’s an all-in-one gardening guru.”  He says.  “Or, it will be.  I hope.  It’s a lot of work.”

“Wow.  Here I can’t even keep a cactus alive.”  I laugh.  “And what about fun?  Are you still into those board games you and Ian and those guys used to play?”

“Nah.  That was more Ian’s thing.  I was just there for the company.”  

“And to check out his hot older brother.”

“Yeah.”  He giggles again, guilty as charged.  “I’m into gardening and reading and…cross-dressing obviously.”

“Obviously.”  I chuckle.

We nod greetings to another couple who pass by us then stop a moment at the window of a hardware store that had been around here and run by the same family since our grandparents time to look at the wares.  In the window we can see our reflection, myself tall and dashing and Toby petite and elegant.  We were looking GOOD!  For Toby I could see this moment struck deeper.  How many times had he dreamed of seeing us exactly like this?  I could only imagine.

“Anything else?”  I ask as we continue our stroll.

“I like to travel.”  I feel him tense up, his gorgeous green eyes scan around the growing numbers of people around us.  He swallows hard.  “D-do like to t-travel?”

I take his soft hand and give it a squeeze.  “Hey, what’s up?  I thought we took care of those nerves.”

“I’m okay.”

“Liar.”

He flashes a terse smile.  “Can’t fool you Raymond.”

“Come on, what’s up?  Never been on a date before or something?”

“Oh, I’ve been on plenty of dates.  Just…never dressed like this.”  He confesses.  “This is my first time in public…in a dress.”

“What!?  Seriously?”

He nods guiltily.

“I thought you were old hat at this shit?”

“Just at home and in certain clubs.  Never out in the world.”  He smooths front of this gown.  “Whoo boy.”

“Ha ha ha!  Here I thought I’d be the newbie here.”

His head sinks.  “Sorry.”

“Ha!  Nah, it’s cool man.  In fact I like it.”  I give him a bracing shake.  “We’re on even footing here.”  I kiss his head.  “You look fucking amazing Toby.  Strut your stuff man, you are rockin this town right now.”

“Thank you.”  He wriggles in tighter to my side.  “Thank you Raymond.  I never would have done this if not…for this date.  You gave me the courage.”

“Bullshit, but thanks.”  I say.  “You woulda done it eventually.  You look way too fuckin good to hide away forever.”

“Oh Raymond.”

“So, how’s it feel?”

“The truth?”

“Yeah.”

Lowering his voice for my ears only he whispers.  “I am so unbelievably horny.”

My brows raise.  “Oh really!?”

“Ray?”  A woman’s voice breaks into our conversation.  “Oh my God!  Ray!”  The next thing I knew a short, busty brunette about my age is right in front of us looking at me like I was her best friend.  “I thought that was you in that hot Ferrari.  Wow!”  She hugs me though I don’t hug her back.  “It’s been so long!  How are you doing?”

“Uh.”  I study the woman a moment as I cast about my memory.  A vague recollection of a handful of awkward dates followed by incredibly tepid sex slowly burbles to the surface.  “Monica?”

“Yeah!”  Her eyes give my date a cool catty glance but she otherwise talks as if he wasn’t even there.  “It’s so cool seeing you back in town again.  I hope you’re staying awhile.  How are you doing?”

“I am killing it.”  I answer honestly.  “Living the dream as they say.”

“I can see that!”  She says looking up and down my expensive wardrobe most approvingly.  “You are looking good.  So handsome!”

“Thanks.”  Drawing attention to my right I say.  “Hey, this is…”

“Oh Ray!  I just can’t believe we ran into each other like this.”  Cutting me off she steps in closer and gives me the eyes.  I actually catch her shoot a glance to my ring finger to make sure I wasn’t permanently hitched.  It was shameless but as a wealthy and reasonably attractive bachelor I was used to it.  “Remember when we were dating?  Those were some times, huh?”

“I guess.”  I shrug, barely recalling them.  

“We were so wild back then!  Ha ha ha!  We got into so much trouble.  Oh my God!  Ha ha ha!  Good times!”

“Right.”  I say, then try to introduce my date again.  “Anyway, you might remember…”

“We went to that awful movie!  Remember?  Talked through the whole thing.  Everyone was so angry.”  She laughs.  “We just kept on doing it though.  We didn’t care.  God, what trouble makers we were.”  She winks.  “You’re still making trouble I bet.”

“Errr…”

“What was it called again?”  She asks, even though I had the feeling she was about to tell me.  “Soldiers of the Stars or something?  That stupid superhero one.  The one with the rat.”

“It was a raccoon.”  I say as the memory comes back to me.

“YES!  That’s right.  You do remember.”  As she talks a couple of other women gather, friends of hers.  I realize that I recognize them as her same friends from high school.  “Movie was bad but what a night afterward though, huh?  Whoooooeeeee!  Oh my God.  I remember you…”

She is about to natter on when I cut her off.  “Hey, you remember Toby.  Right?”

“Doty?”  She says, at last and begrudgingly acknowledging his presence.  “No, I don’t think…”

“Losing your hearing or something?  Not Doty, Toby.  Ian’s friend.”

“Hi.”  Toby says softly.

“Toby?”

“He lived next door to me.”

She looks at him anew.  “He?”

“The Fairy?”  I hear one others mutter, recalling Toby’s belittling nickname among the girls of our school.  It had come out that his character in my brother’s fantasy game was a pixie, this combined with his effete mannerisms and…well, kids can be cruel.

Monica’s eyes slowly widen as the reality sinks in.  I knew I’d get reactions like this coming back here with him, I just didn’t give a fuck, but seeing the hilarious look of shock come over Monica’s face was enough to make this whole thing worth it all by itself.

“Oh!”  She gasps as she looks my date up and down to see this gorgeous man rock his gown better than she ever could.  “Oh, uh, well, uh, that’s …that’s great.  That’s just greeeeeat.  Just so, so great.”  Her face seemed frozen in this sort of half smile and half grimace.  “Toby.  Of course.  Yes.  Look girls, it’s Ray and…Toby.  Isn’t it great?”  Their reactions were much the same hers.  “How…brave…wow.  You look…wow.  H-h-how long have you…have you two…?  When did…?  Wow…”  Unable to control herself she eventually blurts out what she really wanted to say to me.  “You’re gay, Ray!?  YOU!?”  She hastens to reflexively add.  “Not that there’s anything wrong with that.”

This was WAY too fucking funny to let slide.  “Fraid so.”  I say sadly.  “Turns out I always was.”

“No you weren’t!”  She protests too loudly before catching herself and saying at a more normal tone.  “I mean, you were always picking up girls.  You were a man’s man.  You were a stud!”

“He still is.”  Toby corrects her under his breath.  Atta boy!

“It’s true, I was on the fence there for a bit.”  I say to her.  “It was touch and go there.  Coulda gone either way honestly.”

Toby surprises me by quipping.  “And then the infamous Guardians of the Galaxy date.”

“That’s right.”  I say, picking up on his set up.  “The night I switched teams for good.  Worst lover I ever had.  That rotten crotch cunt turned me off pussy for good.”

“Wh-wh-what?”  She stammers, glancing back her friends nervously.

“Yeah.  Smelled like a god damned fish market in July and as loose as a four man tent, I knew I couldn’t go back.  After that horrible…”  I pause.  “Wait a minute.  Guardians of the…raccoon…was that…was that you Monica?”

“Uh…uhmm…”  This conversation had definitely not gone in the direction she’d expected.

“It was!”  I exclaim for all to hear.  “You’re the one that turned me off of women.”  I grab her hand and start shaking it.  “I have to thank you Monica.  Thank you.  Thank you for turning me gay.”

“I-I-I never…I mean, that’s not even possible…I do NOT smell like a fish market!”

“It’s been nothin but cock for me ever since and I haven’t looked back.”  We were drawing attention from others now and I was really hamming it up for them.  “Thank you for showing me the light Monica.  I owe you one.”

Monica pulls her hand away and looks around defensively.  “I never…we never…I never turned him that way.”

“The hell you didn’t.”  Turning to Toby I say.  “Gimme some lovin baby.”  And with that I take him around his slender waist and pull him into a wildly passionate kiss.

Toby is stiffens up in surprise at first but quickly melts in my arms.  “Mmmmmm.”

Fuck did he taste good.  I kiss him hard, I kiss him deep, I kiss him long, all to the hoots and cheers of the horny and the romantic of the crowd.  When our lips finally part I leave my beautiful femboy breathless.  I lick my lips, savoring his flavor for just a second longer, before saying.  “It’s all thanks to you Monica.”

“The Fairy found his knight.”  Whispers Toby, still enraptured by my eyes.

“Pffft!  Gross.”  Monica spins on her heel and storms off, her friends soon following in her wake.  “Asshole, I don’t care if he does drive a Ferrari…”  Her voice disappears into the night.

Toby and I turn to watch the trio bumble and stumble away and share a good laugh.  “That was so mean!”  Toby says between giggles.

“She wasn’t wrong.”  I say.  “I am an asshole.”

“Well, the whole neighborhood will know by the morning.”

“Good.  No point dancing around it.”  I say with a satisfied grin.  “I already warned my parents to expect it.”

“And they were cool with it?”

“Of course.”  I say.  “You were always their favorite of Ian’s friends.”

Looking around to the sneers and smiles our dramatic kiss had caused he whispers.  “You really don’t care what they think, do you?”

“I don’t give a fuck.”  I say.  “If I let that shit hold me back I’d probably still be here selling insurance or something.  Maybe married to Monica, HA!  Three ugly brats running around our feet.  Ugh!”  I chuckle.  “This place molded me into who I am, and I love it for what it is, but you gotta break your mold if you want to stand out in life Toby.  No limits my man.”

“Right.  Break your mold.  Stand out.  No limits.”  He gazes at me in that awestruck way that made me feel so fucking good.  “I understand Raymond.”

“Besides, I’m moving.  Remember?  And I don’t think I’ll be coming back.”

“Oh…right.”  He whispers.

“Let’em think whatever they want.  It’ll give them good gossip fuel for awhile.  I like when people are talking about me.”  I slowly look back his way again.  “Anyway, before we were so rudely interrupted, what was this about being horny?”