tagTransgender & CrossdressersFalling into Being a Sissy

Falling into Being a Sissy


My name's Sonny and well life's been pretty damned golden for me.

I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me.

Middle classed family, decent money for all of that, lots of high school pussy and even more in college.

Being a jock in college doesn't prepare you for real life when you get done and no one picks you up for the league or any league really unless I wanted to play for some hick team going nowhere.

So I manned up and got a job and that turned out well too. I moved back to my hometown so I sort of had that once teen famous thing for being a good player during some of the good years.

It opened a lot of doors honestly.

But life goes on and life settles in and soon my life became work and some friends and well the pussy started to dry up.

I was not looking for a relationship or getting married because honestly so many chicks were gold diggers and seen me having a house and money and stuff as like this invitation for ripping a guy off.

So when the fifth year reunion of out school happened I got a little drunk.

And all my old hook ups were there fat ot married or both or desperately looking to cash in.

Then I saw Josh.

Josh was this guy we kind of treated like shit because he was a fag.

He was pretty, like queer boy twink pretty in high school and honestly he still looked amazing.

I'd been bitching about well...bitches in the parking lot with some of the guys and they had took off when we literally bumped into each other.

"Hey Sonny, watch it okay?"

"Sorry Josh had a few too many."

"Yeah you seem a little happy."

"Miserable more like it, I should find myself a sweet guy like you to boff."

He stares at me.

Lights a smoke.

Nope a joint.

And he keeps staring at me.

He offers me a toke and I take it.

He's got a nice watch.

High end.


Really shiny.

So shiny.

I'm buzzed enough already and the joint is making me pretty fucked up.

I think I spaced out for a bit staring at it and missed some of the conversation.


"What?" I missed something but I'm a bit more awake and with it.

"Okay, here let my drive you home and we can hook up."

I'm not gay.

Like not really gay but had my cock sucked twice in college by hockey fan gay guys and it was pretty good.

I fish out my keys. "Let's go."

I give directions as we go I'm staring at him.

Baby faced, long blonde hair, thin, good looking in that sort of guy and girl way.

Josh pulls into the drug store and comes out with a bag and then we get to my place.

It doesn't take long for us to get inside and I'm kissing him.

He kisses me back and he dumps his jacket and dress shirt as we walk kissing to my couch and his arms are covered in tattoos which is kinda hot.

I get out of my clothes and he kneels and starts sucking my dick and I have to sit down because I'm that bombed still.

I can't get all the way hard, I'm too drunk.

"I'm sorry, sorry...we can do this another..."

Josh looks up at me and kinda smiles and reaches for that bag of stuff and while still sucking me he got out the lube and before I know it his fucking finger is in my ass.

"Oh...oh...jesus fuck."

I mean I was expecting it and not expecting it.

I mean part of me thought that I was going to be the one fucking him and all that top stuff.

I moan as his finger finds this thing or place inside my ass and starts rubbing it and it feels good, it feels great.

It feels like...

My still half soft my dick spurts out a soft cum.

Yeah you know what I mean we've all had those like jerking off or something like not being into a chick and it effects your dick.

I groan by Josh keeps going, fingering my asshole and rubbing that thing inside of me and I can't stop from moaning more.

It feels like that part of me that gets that pleasure jolt before cumming is getting direct attention.

And it's that jolt.

Over and over.

Until something builds to a head and I cum again without spurting.


And he keeps going adding in more fingers?

It feels like that until all I'm feeling is bliss from Josh fingering my asshole and lots of lube until I get off again.

I cry out and cum without cumming and shiver from how it feels in a good way?

I hear him opening a condom and the rustle of the drug store plastic bag then there's more lube.

I was not ready for Josh to put my legs up over his shoulders and for him to sink his cock into me.

It's fucking huge.

And his cockhead was pushing in like me taking this bound up shit but in reverse.

Huge, fucking huge!

I looked, it was nearly a fucking foot long!

And big and thick, of so fucking thick.

Then... the he is...

Opening my asshole up, stretching my well lubed asshole like nothing I knew was real.

Then he's inside of me and I cry out with this groan as Josh sinks into me his huge fucking girth filling my asshole like nothing on earth and his invasion pushing my insides out of his way.


Huge, huge just fucking huge and Josh sank that monster all the way inside of me and then he immediately started fucking me.

Invading me.

Inside me.

Inside me so fucking deeply.

So thick and wide that it's literally destroying any willpower in me that might have stopped this.

Just shock, shock and such a fucking cock.

Ten, twelve strokes in I cum again like when he was fingering me.

Josh speeds up but goes less in, he instead chooses to fuck me so that he's hammering my pleasure bump.

Over and over, hard and really fast.

I gasp, groan, whine from pleasure like a girl would.

It feels like forever that he's fucking me like that so hard then I have another cum like that and then Josh drives that cock in all the way again fucking me harder with those long strokes.

"Aaaaah...Josh, Josh, Josh I'm cumming!"

My cock goes rock hard, harder than I can remember in my life and I fire out gobs of it over me and Josh drives his monster cock in me as deep as it'll go.

"Feel it! Feel it inside you boy cunt, inside your sissy pussy as you get off clenching around me..."

He growls and swells and there's new heat in my ass as he's cumming.

He's right, it's all I can feel, my ass, my insides are clamped around him buried inside of me and that's all my brain can feel.

I'm sobbing because it's the only thing I can do.

I feel Josh move some inside me again and he says. "Off the couch, face down, ass up." Then he pulls out and I roll off the couch and put my face into the carpet and get my knees under me to get my ass in the air.

My dick's spent and utterly limp.

I see Josh discard the huge rubber he used and I think he put on a new one and then he grabs my hips and pushes into me again.

I'm overpowered by that cock again.

My inside trembling with the invasion...taking me, filling me, moving my insides, shaping me to Josh's wants.

He's fucking me hard again these powerful full length strokes driving me into pleasure and madness.

"Tell me more Sunny girl, tell me more."

"Mm...more, more Josh, please more!"

"Ask me to fuck your sissy ass Sunny girl."

"Fuck me Josh, please fuck me!"

"Fuck your what?"

"Fuck my sissy ass!"


"Fuck my sissy ass."

"Repeat it Sunny girl, chant it."

I can't stop, I literally can't stop myself. It's like every time my brain is trying to think of something else my body's filled and invaded by Josh's monster cock and filling me from my sissy ass all the way up my spine and into my brain.

"Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass,Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass..."

I just keep going as Josh fucks me in all these full cock strokes pistoning through me and my brain until he shortens then up to fast fuck my bump again!

"Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass!!"

Josh's cock ramming into me there is sending unstoppable waves through me and I panting like a pregnant girl in that breathy "heh" sound with every stroke and thump inside of me.

"Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass!"

I whine as I'm going to cum again and then Josh.

He stops fucking me there and he doesn't push all the way in either.

He pulls out, he pulls back until the head and a few inches of his cock are threatening to slip free of my sissy ass and he fucks me like that and it's maddening.

"No, no, no...please stay, please Josh stay, stay, fuck me, fill, me, fuck me!"

Josh does this sexy chuckle growl and shoves his cock back in filling me up.

"Good girl Sunny, good sissy girl."

I need it, I need it and I got it, that cock. Josh deep in my ass and part of me is so relieved, so happy.

I made happy girly sissy sounds as Josh filled me and started fucking me long a deep.

"That's it, that it Sunny girl, listen to your body, listen to your real heart, you're a cock loving sissy and you know that's true deep down."

I can't help but agree.

"Yes, yes, yes, I'm a sissy, I'm your Sunny sissy girl, fuck me Josh, make me cum."

He does it this time, he goes into fucking me more in my bump spot until I cum again and then he buries himself in me.

"Feel it Sunny girl, feel it, feel all of that inside all of you."

I cry.

I cry and I sob and I bawl as I feel it, feel that monster cock so deep inside me, taking me over, wrecking my brain.

I cry because I don't know if it's something terrifying or beautiful but I know either way it's perfect.

And so is Josh growling as he's coming inside of me.

He's lying on top of me while I shake and shiver and sob. He's catching his breath as his fucking cock slowly stirs to life and I feel josh pull out of me and the emptiness is a shock.

I think I lost track of time just trying to get a mental grip because before I knew it there was the squirt of more lube and then Josh sinking his cock in me for the third time.

My barely recovered dick spurt this little gob of cum out as Josh sank into me.

"Yes, yes spurt when I'm inside you Sunny, let my cock drive out all that tough guy bullshit."

It's different this time.

It feels so good.

I want, need that massive cock inside me reshaping me as it fills me.

Oh god it's the best, sexiest, deeply satisfying thing.

"Josh...oh god Josh, that dick feels so good Josh, fuck me, fuck my sissy ass, please, please fuck my sissy ass."

I want this more than anything!

Josh starts fucking me with those long deep full length strokes going in so deep inside of me.

Sunny-girl is taking over.

I want that too, just letting go and letting this sissy me take over.

That cock.

This fucking is long, deep, wide, thick and filling me with this glorious warmth.

I feel delirious, fuck fevered.

Sweating, moving with it, wanting it, pushing my sissy ass back to meet him.

"That's it Sunny girl, that's it, push back, love it, ride my cock."

It just keeps getting better the more I just stop caring about everything i was and fuck my way into this...this amazing feeling.

"Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass, Fuck my sissy ass!"

The words becoming part of my brain.

Then Josh starts those amazing strokes where he's fucking my spot over and over again until I sissy cum over and over until I'm panting and the room is spinning and then more full length full depth strokes.

Which drives me over that edge again.

When Josh's huge cock had been making me sissy over and over by fucking that spot inside of me it's sheer animal bliss.

It is.

And I get who and what I'm really supposed to be in like the order of things.

But when he goes from that into sinking back into my sissy ass full length, full stroke my body responds to being utterly filled.

I shiver and shake and cum so hard with my sissy dick exploding again followed by the other sissygasm different cumming that I black out.

I remember the sounds of him cumming again.



And when I woke up he was gone.

There was honestly a mess.

Used rubbers and shit from Josh fucking me and it freaked me out I went on autopilot.

I have to clean my couch and carpet.

After I'd been mastered and sissy fucked.

I got a steam cleaner and clean my place really good.

I'm hungover and so sore.

I was fucked, fucked, over and over in my ass.

My sissy ass.

God, it was fucking great.

I can't get it out of my head.

I can't.

Even going to bed ended with myself trying to jerk off to those memories.

Nothing happens either. I want cock more than I want to cum like a man.

I get up and watch porn on my computer, looking up sissy porn. It was easy to find.


Oh guys turned into or turning themselves into these sexy, delicate, wanton little women, sissies.

Sissies like me.

I watch it all night fascinated, aching, wanting and once morning rolls around I call in sick to work.

I think about getting some sex toys like dildoes and fucking myself.

But I want more.

I want Josh.

He's easy to find online. He's a painter now, an artist like with real canvas and things.

I get showered and drive over to his house.

Aching, wanting, scared, nervous.

It's a nice house, a really nice house in this cul de sac lane with just his house and it's two stories and victorian with a big garage and a tall fenced in backyard.

It takes me a minute to get the courage to go to the door and ring the bell.

I wasn't expecting this tall, beautiful black tranny to open the door.

Six two plus heels and she has a lovely face, nice make-up, in a silk dressing robe and huge tits but there is as much as she's stunning her size that says tranny.

A black sissy girl.

"Can I help you?"

"Uhm...I'm Sonny, I'm here to see Josh?"

"Oh you're Sunny-girl."

I went blank at being recognized.

But something inside felt good, felt happy.

I nod.

She reaches out and guides me in by the shoulder. "Come on in sis, I'm Toni."

Toni closes the door and walks me into this really high end beautiful home and I see Josh.

He's sinking his cock into this brunette trannys throat that looks beautiful as Toni does. She's mounted on this foam sponge tube log thing like a saddle riding this big dildo making her huge tits bounce and her tiny little dick too all locked in in a cock cage.

I can't help but stare as Josh has his hands in her hair controlling her skull as he fucks her face. I can see is cock sliding in her throat making the flesh bulge out.

She's blissed out her eyes rolled back in her head as she grabs and plays with her huge tits and I can hear the muffled moans as she's having sissygasms.

I'm hard as fuck and I want to be her.

Toni says in my ear. "Don't worry Sunny-girl, you'll have your turn."

She guides me to a seat where we can watch and my eyes are glued to the scene even when Toni unzips me and pulls my cock out and gives me this blowjob from hell.

It almost distracts me from wanting to be the brunette.

She really was into it and loves sucking cock and deepthroated me easily and I swear she was so fucking happy that my cock was down her throat.

Smiling around my cock, her eyes shining and yet glazing over in this raw slut sissy love.

I came hard and almost in time with Josh getting off and me seeing the brunette's throat contracting as she swallowed his cum.

I watched Josh's cock slide out of her then she slumped to the floor still mounted on the thing, still clutching her big titties panting and giggling.

Then he walked over to me and sat in a nice chair that matches the sofa set and he smiles at me.

"That was fast."

"I...I can't sleep, can't cum, I can't stop thinking of you Josh."

"I know, you took right to the cock Sunny-girl you're a born sissy."

"I was never into stuff like this before."

Toni gets up and goes and makes drinks. "Neither was I but it just took one night for me too. I can't go back Sunny-girl. I won't ever want too. I'm a sissy, you're a sissy."

"But I used to be a hockey player."

"I know, we went to school together. I was on the football team."

I look at Toni, whoever she was he's long gone.

"I don't recognize you."

"Good, that guy, he's gone and I'm left. And I'm happy. You will be too."

She passes drinks around and it's strong, strong rum enough to make me cough and Josh rolls a few joints and Becky joins us and she's so perfect. Tall, long legs, huge perfect tits and she's drop dead pretty like better than some women around here for sure.

Only her little caged cock shows she's a tranny like hardcore.

We drink and smoke up and listen to music and Josh's watch catches my eye again.


So shiny.

I'm so buzzed.

I sort of fall down this hazy hole where they're all talking but Josh especially.

I'm still buzzed as hell when my head clears and I can't wait any more and I slide off the couch and go to Josh on my knees and he's hard again.

It's huge, it's amazing, it's beautiful and my mouth is literally watering as I start sucking on his cock.

I need both hands to do it and my jaw gets sore easy but I don't care.

It's so good.

It tastes so good.

Cock tastes so good.

I want more and more I want him, need him inside me.

I cum from getting turned on too much as Josh's hands grip my head and he takes control of me.

Yes, yes, yes...take control of me.

Josh shoves himself deeper and deeper down my throat and instead of choking something happens when he hits my gag reflex.

When he pushes his cock past that point.

I've fucked girls, I've fucked lots and lots of girls.

I know what sinking cock into pussy feels like.

This, this is something like that but not.

I've had cock sinking into me.

Yeah just Josh's but still.

It literally feels like when Josh's giant cock pushes past my gag point it sinks into my brain.

Like my brain has a pussy.


Inside my brain feels pushed open and filled like my ass was and my brain went squish.

It literally feels to me like inches of massive dick drives through my brain because there's a cunt there, a pussy, a brain pussy.

I feel it invading my mind.

Sinking in, taking over, my brain a pussy for that giant cock.

It's so real, it feels like a real literal physical thing.

I feel it so much that it's like some science fiction invader.

I feel cock in my brain pussy.

Sissy girl brain pussy.

Sissy girl brain pussy.

Sissy girl brain pussy.

Stuff that I was thinking, or might have been thinking just becomes pleasure and cock driving into my brain.

I cum spurting it's too much, I sissygasm after that just turned on too much and being just too much of a driven sissy.

I feel things slipping away but who fucking cares.

I'm real, home, a sissy, I feel so fucking true, right, happy.

I just give up on thinking too after a while and just revel in it.

Until Josh cums and fills my mouth, my throat and my insides with spurt after spurt of heavenly cum.

I so get Becky now, blissed out, happy, giggling.

I lose track of time and don't care.

When I pick myself off the floor Becky and Tina take me to "The Sissy room."

Everything is different.

We giggle and talk as we start getting rid of Sonny and starting my new life, my real life as Sunny.

We talk about Josh, about his giant cock, the stuff he likes and does and about brain pussy and the real truth of it.

Josh's cock is literally like something holy and getting to feel cock in my sissy brain is joy.

A privilege.

That they have thing too, the same feelings.

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bySissyhalo© 8 comments/ 29250 views/ 36 favorites

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