Date Night with a Femboy: Part 2 (Patreon)

Top down and the warm sun shining on my head my racing red Ferrari Spider snarls through the previously serene neighborhood.  Nearly six hundred glorious horses roar then come to stop on a dime in front of the quaint little bungalow that matched the address on my phone.  Curtains raise and curious heads pop out here and there as I exit the vehicle and close the door.  I nod to a few of them as I strut up the walk.  The front yard was immaculate, the walk flanked on either side with borders of delicate pastel flowers.  It was damned pretty.  A real soft touch.  I liked that.  Not because it was something I would do with my lawn but precisely because it wasn’t.

Taking the stairs all in one go I stand on the porch and smooth out my fine silk shirt and trousers.  I unfasten the top button to let some chest hair peek out then step forward and knock.  I hear a startled peep behind the door followed by scramble.  A moment later the door glides open.

“Ohhh my Gahd!”  I exclaim as a lady of unparalleled radiant beauty reveals herself.  He might be a dude, but looking like that he sure as fuck was a lady too.  Toby wore a sleeveless gown of rich ruby red that made his lovely pale green eyes nearly glow from the contrast.  The style hugged his body in just the right places to accentuate he lean bust and deliciously subtle curves.  On his smooth elegant arms he wore long gloves, on his dainty feet he had on red open toe pumps that showed off his glossy red nails that matched his lipstick.  At my insistence he had no wig on but his sandy brown hair was up in a very classy and very feminine style that showed off his long delicate neck.  A bit of blush, eyeliner, and glimmering dangling earrings round out the look.  By God!  He was EASILY the hottest date I’d picked up this year.

With a bashful smile that made me want to bend him over right there he bows his head and giggles.  “Hello Raymond.”

“Hello Toby!  God damn boy!  Whoooooeeeee!”

He is all smiles as he lets me in and closes the door.  “I am glad you like it.”

I look around his pad.  It was humble but it was nice.  The decor showed the same tasteful touch as the garden out front.  Toby clearly wasn’t rich but he wasn’t just scraping by either.  “Nice place.”

“Th-thanks.”  Gripping his hands nervously, which had folded in front of him, he stammers in a soft dulcet voice I’d never heard him use before. “Y-you are looking v-very handsome today.”

“And you are looking hot as hell.”  I say as I openly scan up and down his lithe figure.  “Fuck.”

He giggles again.  “I c-c-can’t believe…I can’t…th-that we’re actually…”  He snorts as he struggles to compose himself.  “Th-tha-thank you…f-f-for…”  I chuckle as I watch him adorably tripping over words.  The gold-diggers I usually dated had their game smoothed down to a silky science.  I very much enjoyed that Toby’s nerves had him a bit rougher around the edges.  He takes a big breath in and lets it out with a shudder.  “I’m blowing this.”

“Nah, you’re good.”  I smile.  Reaching into my pocket I pull my gift for him, I always got my dates gifts.  Opening the little jewelry case I show him the slender necklace with the tiny rose pendant within.  Nodding back at his yard I tell a blatant but flattering lie.  “I saw that you liked flowers.  I thought you might like this.”

His eyes widen as if he could not believe what he was seeing.  “I do!”  He whispers.  “I do like flowers.”

“Great.”  I wink.  Carefully removing the incredibly delicate chain I place it around his elegant neck and clasp it on.  As I leaned in I could smell the gentle floral aromas of a very nice perfume, he smelled every bit as good as any woman I’d dated.

“Th-th-thank…you…”  He brings his long fingers up to touch the tiny rose.  “Thank you Raymond!”

I just smile.  I was very much aware that I was here making his dreams come true and I very much wanted for this night to live up to his fantasies.  This wasn’t merely out of charity either.  Since his confession on my doorstep my self-confessed over inflated ego had been sent soaring.  I knew that most of my high school cohort thought that I was a loudmouth and blowhard, and they were right, but knowing that one among them thought higher of me…knowing that I was that special first crush for somebody…well, it touched even my cold heart honestly.  And the fact that I’d been dying to fuck a sexy femboy’s brains out for as long as I could remember touched my dick.

Gasping through shallow breaths Toby tries mightily to settle himself.  “So where…where are we…going?”

“Jesus.”  I laugh.  “Calm down man.  Where is that confidence from the other day?  Where are those balls of steel?”

“I’m sorry.”  He gulps and gasps.  “I’m just so…whooooo…oh boy.”

I look at him standing there, blushing and flustered, and something just…seizes me.  Stepping into him I back him up against the nearest wall.  He looks up at me with huge stunned eyes.

“Hands behind your back.”  I tell him.

His mouth partially hung open he simply nods and obeys.  There wasn’t even a moment of hesitation.  This was a good start!  Reaching around him I grip his wrists in my large hand and hold them there firmly.  I lean my weight into his shoulder to pin him then with my free hand I lift his dress.

“Oh my God!”  He gasps breathlessly.

“You gotta shoot a pre-date nut man.”  I say.  “Dating 101.  Settles ya right down.”  The hem of the dress I tuck in between us to keep it lifted.  “I also gotta do a dick check.  You better not be bigger than me.  There’s only room for one alpha dog on this date.”

“I’m not!”

“Let’s see.”

I peer down to see that he was wearing a black pair of lacy panties, sexy yet dignified, and I find him to be already rock hard.  His gown, fine enough for a fairy tale princess, had been concealing this raging specimen of manhood.  Fuck!  I’m not sure I’ve seen anything so sexy as the contrast of a stiff cock and a set of balls bulging within a pair of women’s sexy underwear.  I look at up him and smirk as he gazes back, a flush of pink coloring his fair cheeks.  Despite being handled like this he does not struggle or complain.  Leaning into me I feel him relax to submit to my touch even more.

“Let’s see this bad boy.”  With my big beefy mitt I pull down the front of his panties to unleash his stiffy.  Cupping it in my hand I look down, studying it and feeling its warm harness in my palm.  “Fuck you got a pretty cock.”

“Hohhhh.”  He sighs, his voice lilting and lovely, as I slowly stroke the underside of his six and half inch cock.  It really was a pretty thing, as pretty as the rest of him.

“And it ain’t too big.”  I lean in and kiss his cheek.  “Closer than I’d like, but I think we’ll be just fine you and me.”

“G-good!”

I close my hand around him and start to dry jerk him right there in the entryway.  His hands held behind his back with one hand, my shoulder pinning his shoulder into the wall, my other hand stroking his cock I hover over him.  My face is just inches from his as I watch the feelings of pleasure ripple across his beautifully expressive face.

I gaze hard, drinking in his girlish beauty.  “How in the hell did I never notice you before?”

“Hahhhh.”

“You are gorgeous.”  I let out a hot sigh, letting my fresh minty breath wash across his cheek and neck.  “You are the hottest piece of ass I’ve ever fuckin seen.”

“Ohhhhh.”

“And I had you right next door all that time?”  Nuzzling into his flushed cheek I kiss it again.  “I woulda snuck you over Toby.  Turned out that hot sissy ass every fucking night.”

“Ohhhhh Raymond.”  His rigid cock flexes hard in my hand.  My grip tightens and I stroke him faster.  I handle him rough, like a man’s man.  I knew I’d rub him raw if I kept this going too long but by the hazy look in his gorgeous green eyes he wasn’t going last long enough for that to be a problem.

Sliding down to smoothest, softest neck I ever felt I nuzzle and suck and nibble.  “Mmmm.  Fuck, you even taste good.”

“Hoohhhhh!”  His lean body begins to move with my rough stroking hand.  “Ohhhh God yessss.”

‘I’m gonna treat you so good tonight baby.”  I growl, my own rising passion getting harder to ignore.  “I’m gonna treat you like the queen that you are.”

“Oh…Ray…OHHHH!!!”  His hips suddenly buck once and his dick throbs hard in my grasp.  Looking down I watch as the first great rope of glistening creamy jizz shoots from his hard cumming balls.

“That’s it you sexy bitch.”  I hiss.  “Cum for me.  Cum for Daddy you little slut.  That’s it.  Good boy.”

“HAHHHHH!!!”  His high voice is part sex demon and part angel.  He whimpers and shudders and makes the cutest fucking noises as I pump him dry.  As his climax fades he slumps heavily into me, panting heavily.  I milk him to the very last drizzling drop before letting him go.  I swipe his tip clean with the pad of my finger and bring it to his open lips.  I swipe the bit of jizz across his tongue.  He sucks my finger clean as I pull it away.  Looking even hotter than before he gasps.  “Oh Raymond!”

“There.”  I smile.  “Now you’re ready for our date.”  I tuck him away in his sexy panties and let his lovely dress fall back into place.  With my big hand I stroke a stray strand of hair that had come free and tuck it behind his delicate ear.  “Ready to go?”

He is in awe.  Gazing at me like nobody ever had before.  Smitten beyond words it was more than simply desire in his jade eyes, it was worship!  He looked on me like one would a living god.  That felt…nice.

His trembling voice barely a whisper he answers.  “Yes.  I am ready.”

“Great!”  I say as I offer him my arm and guide him around his mess.  “Watch your step now my dear.  I’d hate to see you slip and mess up that nice dress.”

“Ohhhhh Raymond.”  Holding to my muscular arm he flops his head onto my shoulder and follows my lead.

I am walking tall and proud as I stroll down back down the garden path with my date on my arm to our awaiting chariot.  I was making dreams come true tonight and damn did it feel good.

Part 3