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  • Jock Princess Ch. 01

Jock Princess Ch. 01

I'm Alex.

And I got to admit that life's been kinda good.

Cake actually.

I'm a jock, left winger hockey player and all through high school it's done me pretty well. My family owns a good business in town actually a few of them. Grand dad on mom's side had a dairy farm and actually did okay, Mom's a registered nurse, my dad owns a big hardware store and adjoining nursery.

I kinda never really lacked for nothing either and always had money.

Oh I worked for it, the family's pretty big on that but I never had to look for work.

And always got paid well and as long as my marks were good in both high school and college dad paid for the schooling and for all that stuff. Me just my clothes, food, upkeep on my cars and my basic bills.

I never lacked for pussy either.

I'm not bad looking but yeah I had it made and girls were very into that.

They weren't so much into my sister's or my mom keeping a really sharp eye out for gold diggers.

And yeah there were a few.

And yeah I broke up with a lot of girls simply for no good reason other than I literally didn't have to settle.

So after college I went to work for Dad and I'm okay with that too.

We have a big business and that's my degree too bachelor's of finance. I'm kind of expected to help and eventually take over.

But everything changed when I decided to buy a house.

It was a fixer upper for certain but hey, the family literally was in hardware so I moved in and started working on it.

And that sort of led to fixing it up at night when I'd stay over.

That's when I met Jason.

I think I knew him in school like way back and he...he was handsome in that pretty way.

Long black silky hair, kind of a goth but not. He didn't have the clothes or that junk jewelry.

He reminded me of a sissy boy.

You know, those crossdressers and shemales.

But one of those guys that can pass for a girl with really little work.

Yeah I know what all that is, I've seen lots of porn, followed a few links and jerked it to the pretty ladyboys.

I guess we were on friendly terms for about a few months before I invited myself over after I'd gotten the living room all done and painted and squared away.

I rang the bell.

He answered all pretty looking and dressed down in the whole relaxed black t-shirt over one of those long sleeved t-shirt like things and faded jeans, long black hair hanging loose but kinda tumbled looking...killer blue eyes.

"Alex."

"Hey Jase, I just got done the living room and thought that I'd celebrate and well you're here."

I showed him the bottle a nice bottle of Appleton's rum and he casually shrugged. "Cool come on in."

I'll admit getting really impressed by his place. Nice furniture and carpeting with a really killer home theater and fireplace but a great collection of art, art prints and this sort of eclectic geek stuff.

A bookcase stood out nicely with like definite geek stuff on it but a lot of books too like two shelves of hardcovers.

"Nice place."

Jason got glasses and ice. "Thanks."

We drank quite a bit and he showed me around and he's an artist. Like a real artist with a basement studio and everything.

He'd be a sexy she.

And I was drunk enough that I said that. "You'd make a sexy girl."

"Excuse me?"

"Y'know, you're hot Jase, pretty even and there are boys out there that'd make better girls."

"Like you."

He said that and I blinked.

"Uhm...no, I'm not the pretty one you are?"

Jason looked at me. "I think you're pretty Lexi, nice eyes, an oval face that has you look kind of girl like, you must take after your mom. I'd fuck you."

Huh...what?

But...seriously?

Lexi?

"No, no Jason you're prettier than me, it's like who has the little sissy dick is the girl."

"Oh really?"

"Yeah...!" I was drunk, I dropped my pants and shorts and pulled it out half stiff and stoked it. "See big like seven inches!"

Jason dropped his pants and he pulled out something my full size and growing.

"Oh shit that's a big cock."

He stepped up and took my hand off my hard on and put it on his.

I didn't know another's cock would be that heavy...I could feel his pulse, God it was hot and hardening.

"C'mon Lexi you know the rules. Smaller dicks must serve."

I did didn't I?

And Jason's cock was bigger, a lot bigger and in my hand and getting harder and throbbing.

I dropped to my knees and I don't know why other than it's kind of sort of the "rules" I started trying to suck that cock...god like those sissy blogs say. "That first taste."

I had no clue I was...I mean I'm a built dude...a jock.

After a few minutes Jase pulled away. "You're not loving that enough Lexi, go home."

"Go home?"

"Yeah go home, come back when you're cleaned out and hairless and smooth and ready for me."

I was barely dressed when he had me out of his place.

That's never happened before?

I...I could still taste his dick from minutes ago.

It wasn't enough?

I wasn't enough?

I went home with a raging hard on then beat off fantasizing of when I had that huge cock in my hand and in my mouth.

I caught my cum as much as I could and ate it wishing it was his.

Fuck...

The rest of the week was me being obsessed. I drove myself a little nuts watching shemale porn and going to those sissy sites and pages. Part wanting to fuck them but more than ever wanting to be one of those girls.

Exposed to cock...that first time...feeling those needs...knowing I'd never be the same.

I mean never, ever in my life had I been turned down before or turned on so much.

Hell I think part of it was entitled ego and getting turned down.

But another part of me...wanted it, that huge cock, wanted Jason with every passing day.

I bought Veet and got smooth and went to the mall and bought things, things to get pretty...I had to right? Make-up to try those You tube tutorials, condoms, lube, toothpaste, lotion, baby powder.

I even went to Victoria's secret and bought panties and a couple of camisole tops. No one batted an eye because a guy like me was buying for a girl right?

I tried different things, trying to be pretty, to see in me what he said.

Jason said I was pretty, he called me Lexi.

It turned me on harder.

I mean I'm brown haired, green eyed and well muscled and lean.

I look like a guy.

A good looking guy with a damned decent cock.

But here I was taking time to get smooth, do my toenails, learning how to get sexy eyes and use fake nails and lashes.

Getting my wig just right.

Jason was right about my face though, especially made up a little and wearing the wig.

And ending up looking like a sort of pretty girl with way too big of shoulders and way too defined muscles and no tits.

Some really weird chimera.

I'd even get myself cleaned up inside just to be used to it for...for that night.

That was embarrassing, freaky and at the same time made me ache to be filled every time I cleaned myself out.

That weekend I took extra care of everything. Wig styled, best panties on, nails, make-up, lotioned sweet smelling body, soft pink glossy lips. I even had gotten a simple white and peach flower dress, purse and flats.

I was scared, scared out of my head.

After it was pretty late I went out back and crossed yards and knocked on Jason's patio door.

I had to knock a few times before he showed up from downstairs where he'd been painting he walked over and he opened the door.

Looked me over with a raised eyebrow.

"Very cute, very sexy Lexi."

I blushed. "I...I tried."

"You're sober too, pretty serious huh?"

"I...I don't even get it...I mean...I don't get why?" I wanted to know why, I wanted an explanation why.

"You will, come with me."

God he was sexy, pretty and those eyes.

But his voice too...sexy, soft, strong though.

Jase took my hand and led me to his bedroom which was as cool as the rest of the place. Artistic, sort of spartan with the bed being the really only feature in the room aside from the art. It was a nice bed too with this simple boxed dark wood frame and nice sheets no footboard that I could see just a headboard console like thing.

Jason led me to the bed and turned on some music, something soft and mellow like John Legend.

I slip letting the dress fall and blush stepping out of the flats then got on his bed.

I was surprised when I turned and he kissed me.

Strong but gentle, his hand on my chin tilting my head up and Jason kissing me like I'm the girl.

The bed was super soft and the sheets were really nice too and I unbuckled his jeans and let them fall and his underwear too as I fished out his cock and stuffed in my my mouth.

Sucked on him, growing that monster until he was hard.

He pulled his shirts off and for a thin guy he was ripped, great definition, full six pack and everything and he had tattoos. Both arms were covered and with cool stuff not gang shit or nazi bullshit but ravens and spiders and straight razors and candles, blackened hearts and even on one a pretty big dragon the one from those dragonball cartoons and the other a pretty big dandelion.

He had a wreath of thorns in black around his belly button too.

God damned he was sexy as fuck.

All of it made my not able to not touch him, run my fingers over tattoos and his muscles.

Made sucking his cock so much better, sexier.

He pulled out when I kind of gagged a little.

"Roll over, and pass me the lube."

I shiver at the command. Jase has this soft spoken no bullshit, take you over sort of voice. I get the lube and give it to him and roll over and Jason slips my panties aside and starts lubing my bum.

I shiver and whine moan.

Jason says softly. "Good girl, good girl Lexi."

His fingers find my sissy spot.

I read about it but never...oh god never.

Getting finger fucked was life changing, Lexi waking, making me whine and shiver and moan all the way to squirting and Jason kept going fingering and rubbing until something else happened.

I had a sissy orgasm.

It was like cumming, exploding inside of yourself.

It changes your brain when you've been a really successful hetero guy all your life and then you're getting fingerfucked and cumming without your dick.

And Jason adds more and more lube and fingers and fucking me until his hand and arm was tired.

I was dazed until Jason's huge cock sank into me.

I cried out and face planted and moan-wailed into the sheets.

Fully girly, full on the girl getting her cherry popped.

It was just the biggest thing, this great swollen tip slipping in past my anal ring and spreading my insides more and more and it hurt but didn't. Jason took his time letting my body adjust and me to lose my mind.

It was like that too there was no part of me remotely ready for this.

Jason's huge cock sinking inside me opening me up, waking nerves, needs, parts of me that I was sure never existed.

I tossed my head, screamed as I was being filled up.

"Aaaaaaah...aaaaah! Fff...fuck...fuck...cock...huge...cock...!!"

"Higher Lexi, pitch it higher, say it higher."

Jase's cock filled me, possessed me, took me over as he pulled out and sank back inside and he started fucking me.

It was dominating, this huge thick thing pushing and pulling in and through all of me making me feel.

"Oh...ooooh fuck...good...so good!!"

"You've a tight sweet ass girl."

"Unngh...ahh...how...how...unng...Jase, Jason, why...? Why me?"

He sank his cock in deep again.

"Because when you think of doing those sissy types you think about being those sissies yourself don't you?"

"I..." Oh god, oh god the cock keeps driving me, sinking deep, pushing over the edge.

"Yes, yes...oh fuck...yes..."

"So you did think of this?"

"Gnnnh...yes, yes...since I tasted you..."

"You know you're not the only one. Not the only guy that sees the way I look and thought like you did. You are the first one that didn't flip out when I turned the tables, most do that freak out but not you, not you Lexi you went for it and beyond."

"R...really? F..ff..fuck, so glad that I did..."

"You like this huh? You're my first for this actually."

"Like...like...ff...fuck...love it, love it fuck me Jason, please fuck me, use me, make me your sissy."

"If that's what you really want, I gotta say you're boipussy is really tight and very clean."

"Gnnn...yes...I want it...please Jase fuck me...please baby do me, fuck meeeeee..."

I had another sissy orgasm.

He got into a tempo and the invasion became my surrender, became me becoming this sissy girl crying her eyes out because it feels better than anything in her life.

I got hard in my panties again, get hard and untouched Jason keeps fucking me until I lost it and squirt filling them again.

Then who knows how much bliss later another sissygasm.

He has such staying power too it feels like forever before he got to the point where he gets close and starts fucking me harder in that guy getting ready to cum way.

I got to where I grabbed his pillow and was shrieking into it as his cock rammed through me.

I felt like one long extended orgasm until Jason buried his cock inside of my hard and deep and there was this blissful little pop in my head as his cum blasted my insides and boiled inside of me.

I joy sobbed.

Jason just held my hips in this really strong grip and rolled our hips riding out the orgasm as more cum, the rest of his cum was emptied into me.

I collapsed when he pulled out and let go of my hips.

I was in literally fucking shock on the bed and he left and came back with two big lemonades on ice with straws and a hot damp towel and he pulled my panties down and cleaned me up.

Gently.

Which made my shocked brain cry in little happy bursts.

Jason moved the covers and we climbed into the bed after finishing the drinks and he kissed me again.

"Stay the night?"

"You want me to?"

"Yeah, we're lovers and I'm not an asshole...stay."

I swallowed and shy smiled. "Okay."

He kissed me again. "Good."

God...my brain was trying to process all of this but the bed was soft, I was literally fucked to exhaustion and the sheets felt amazing and...and Jason spooned me.

I fell asleep held like that for the first time in my life.

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