Finding Claire

Story Info
Hayden goes deeper into becoming the sissy Claire.
5.7k words
4.64
33.4k
25
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Sissyhalo
Sissyhalo
667 Followers

*Before...

I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower.

Thinking on all of it a lot.

Then I check my bank accounts twice online.

I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back.

It's my second house here actually with Roxanne getting the first house.

But Thompson's auto is kind of big stuff here we sell new and used with us owning lots for the big three plus two big used lots with one being classic cars and then the mechanics, the auto body and the parts/recycling yard.

Me I manage things along with Holden the oldest brother between Holly and me. I do that and work the classic cars and the maintenance contracts. I make really good money plus I still get commissions.

I'm...I'm kind of not pissed at Roxanne right now.

My new place though not that new is a place, kind of a trophy a thing to show off...a dick measuring thing in the family...a thing to wow pussy.

Wowing...so much of that's not important now.

It feels like it's where I sleep not where I live.

It kind of feels as empty as work.

So what do I want?

A fence, I want privacy for sure...a pool would be nice maybe with a hot tub? A back deck that's better, not just a place to put a bbq I will barely use.

I head back inside and go through things until I find a notepad and kind of sketch the house.

I want to remodel too. My room it can be bigger, I don't need three bedrooms. I'm not ever going to have kids.

Big luxury bathroom, all the things and big closets maybe.

I look through things online, no not the porn stuff but furniture, bedding, clothes, things...things for a life my life.

I found my fencing and my deck that fully done composite stuff from Home Depot...no staining, coating, lasts and lasts.

I shop for all the things to go with it eventually.

Then saving the ads to a file.

Then it's looking at girls things, clothes, shape wear...under things...I have this huge way to go...honestly it's so big a void between Hayden and Claire it really hurts.

*And Now...

It's sort of messed up how plans or making plans sort of derails you into thinking about how hard things are going to actually going to be.

But I needed to make plans...I need to change things and be me.

Hayden has no place being who I am when who I really, really am is Claire.

I mean...after everything so far, all the cock, all the cum I've swallowed and it feeling so right, so good how could this not be true?

But thinking on how hard it was going to be was dragging me down. I don't want to be down, my life's been down after down.

No fuck that.

Fuck Hayden and being a miserable little prick.

I force myself out of that with another shower and sweet sexy smelling body wash and a couple more drinks and a joint while listening to tunes.

As I'm letting the buzz hit me I'm setting things up for my dildo "Tommy" with the tray to stick the suction cup base to and some thick towels and I get a bowl of hot water and set him in it then my KY warming lube.

I pull my laptop over and bring up the tabs for the sissification sites that I've been watching and start watching.

This is who you are inside, this is who you can become.

Get buzzed, suck cock.

Stop lying, start loving that cock inside you.

You've never been man enough but you can be sissy enough.

Worship cock like a good sissy girl.

And there's more and more always more and hundreds of images with them too that show girls like me that were born with these tiny dicks getting cock.

In their asses, getting fucked, sucking cock...I'm really craving cock in my mouth right now.

But their happy.

So fucking happy.

I am too...this, this...just giving up on being Hayden and going with this is just...perfect, better, me as I should be.

Not a man, not really just convinced of it over time.

I moan as I lube myself, reaching my two middle fingers deep inside until I find my sissy spot and start milking myself pulling on my little cocklette my sissy clitty until I shoot cum while watching a flasher that teaches and tells me.

Train yourself...teach your body that coming like a sissy is the best way...do it, milk yourself, train your body, it will learn, you will learn.

I can sort of feel it too, that I like this better, my body knows and likes this better than the old way, the guy way.

That I don't think I was really made for.

I mean would this even feel better than the other way if I wasn't made for being this way?

Like they keep saying some boys were made to be girls.

Well...

They also say some boys are meant to be sissy girls too.

That thought makes me giggle then gasp as my fingers rubbing inside of myself get me close to having a sissy orgasm.

I add more lube and then take "Tommy" out of the bowl of hot water and stick him in place and settle myself down on him.

I moan, really moan as the thick dildo pushes into my bum and spreads me wide.

I love being entered, love penatration, open me, open me, oh fuck...oh fuck!

When that hot water heated cock touches my sissy spot I have a sissygasm right there.

"Aaaah, aaaah hot cock, hot cock!"

I bunny hump that hard unyielding dick inside me making myself cry in pleasure and fisting the covers of my bed.

"More, more, more...!"

"Faster Claire, fucking faster...!"

My sissy nerves are sending a surge of unfiltered FUCK! Into my brain and I get myself to a record fast cum.

I can't breathe for a few seconds it was so good and I giggle and giggle as I'm that stunned that I drooled a little.

I let myself sink to the base and breathe.

Laughing, giggling with a hard cock inside of me feels good I can feel my body clench and seize around all that thickness and length inside of me, so deep inside of me.

I'm so fucking high, dick drunk and high and I just sit there impaled and so happily dick blissed out that it's like high, a little drunk sissy zen.

It's kind of this perfect zone honestly.

Well not perfect, if it was perfect I'd be mounting a real guy and full of real cock and I'd be sucking on cock too...and I'd be softer, skinnier, pretty with boobs, big full boobs that would get squeezed, titillated, titty fucked and covered with thick ropey yummy cum.

I sway happy and filled with hot cock as I find some sissy hypno videos the flash into my stoned brain.

There's this little bit of my brain somewhere that's trying to be that fake me, trying to hang onto some shred of things and that actually makes it better.

I want to punish that little tiny cocked asshole because everything was just wrong from the get go when I knew I had a little cock.

I should have been doing this, being me all along.

Instead of the macho bull to keep up.

So yeah I find a flasher sissy hypnotic video and I really on purpose stare into the screen and let my attention drift...just watch and kagel my bum around the really warm hard cock filling me up.

I move my body watching feeling that big dick inside my tiny asshole still stretching me wide, still making me moan and moan and shiver with pleasure.

"Fuck me, fuck me, fuck me..."

"Cock in my bum makes me happy and dumb."

"Cock in my bum makes me happy and dumb."

"Cock in my bum makes me happy and dumb."

There's a flasher playing in front of me with sexy she males walking towards the camera and the words just pop in and out of being there.

Leave manhood behind, leave manhood behind, leave manhood behind, suck cock, grow breasts, suck cock, be a sissy, you need to be like her, you need to be like her, you need to be like her, suck cock, enjoy cum, be a sissy.

Then another as I ride Tommy hard and deep using gravity to drop me down in hard sooo good thrusts.

This one has a sissy girl like me with pig tails and tiny titties being fucked by a big strong looking guy with a big dick.

Sissy feels good, Sissy loves cock, Sissy cums for cock.

Her eyes are half lidded from getting fucked, glassy in a good way and only widen when he makes her spurt.

It's big pink letters over and over and I watch that one for such a long time until I'm moaning and edging and drooling from my little cocklette but not able to get hard at all and the cum just sort of drools free and I shiver through a sissy orgasm as I repeat what's there over and over.

"Aaaah sissy cums for cock!"

I collapse panting watching that one over and over pouring into my brain.

Her eyes, my eyes, her eyes, my eyes...I can feel it, her, me sooooo much.

My own thoughts just spin in this cycle of all of the things that I've watched as I stare into her eyes.

...sissy, swallow, cock, worship cock, you're not a man, you are a sissy, you are a sissy, you are a sissy, suck cock, be happy, suck cock, empty your mind, keep watching, suck cock, be happy, drink cum, be happy, swallow semen be proud, suck cock, be happy...

... Relax, Keep Watching, Be a Girl, Suck Cock, Be Happy, Be a girl, Be Happy, Lose Weight, Be Happy, Wear Panties, Be Happy, You're a Beta Male, Sucking Cock Makes You Happy, Relax, Be Happy, Keep Watching, Be Happy...

I can't stop the smile as her eyes are mine.

I giggle at the feeling of things just...just not mattering at all but this right now and that sets off being filled with the big dildo and laughing and how that feels plus being giggly and still stoned.

...You love his dick, let him breed you...

...I love myself as a girl, be a fuck toy, be a sissy, submit...

...If you ever got off from dick in you it's permanent, you're a sissy now...

...If cock inside you has made you cum you aren't a real man anymore...

...Little dicks are just waiting clitties...

...Small dicks are betas...

...Small dicks must serve better men...

...You're not a real man anymore...

...Dildo in your ass, on your knees, clitty limp, mouth open, good sissy...

All of it me.

I feel better.

I feel amazing but wore out and well fucked and I clean up slowly and then climb back into bed and just sleep and dream of being me.

And it's more than the sex dreams too.

I dream of my place, here what might be if I'm really me and happy.

I dream of my sister Holly...the life she's living now.

Off somewhere for the long weekend with her guy, off having a life.

I want that too, want my life.

I wake up in the afternoon and putter around the house cleaning up some more just really taking my time and getting my house to a better standard.

I end up making a salad with some of that tuna with the spicy chili on it and sit and watch TV.

I'm going to need to lose weight, drop muscle mass, get smaller...I really want to...especially if I'm going to go further.

I try watching different things than before too girly stuff honestly trying to put myself in their place, trying to picture it all.

I've missed out on seeing so many things that are different.

The other side of things.

And there's times I do get lost in the story.

Then there's times where I'm just sort of reminded of the differences between all of them and me as I am now.

God part of me wants to go out and go to the truck stop and try my luck.

God I need to do something.

It's late afternoon and I was bored and I left the house and went for a drive. Part of it was just sort of watching people but part of it was to get out of the house and away from the boredom and the temptations of heading into the bedroom again and losing myself.

I actually go looking for things, things for me as Claire and I go looking in places that I usually never got to these small clothing shops that are still open even if it's the long weekend and there's a seamstress shop that I find with an attacked thrift store that has some things that I like.

I wear a hoodie to make sure that I'm sort of unseen, not that I ever get over this way and heck the shop girl isn't even white.

Then kind of satisfied and I go home and dress.

Play dress up.

I've some nice pairs of women's slacks and I have some nice tops to go with it ad some of them are girls rock and pop band tee shirts and there's a sweater I like and there's a couple of skirts too especially the old but faded just right denim mini-skirt.

I try that and play with my make-up and hair trying to look at least okay, like trying to see if I can see me.

What I do see is the this kinda middle classed rocker girl with good but bad make-up that kinda punk look, and no breasts at all.

But somehow I do have the hips right and the denim mini actually looks really good on me, bra with gel inserts which helps and a Seal... Kiss from a Rose tee shirt that's a little loose on me and a little long so I get a belt.

And now it's past supper and heading to early evening so I take a breath and pack a purse I bought and go for a drive. My windows are tinted so I'm not too worried about being seen.

It's Canada Day evening so there's some stuff going on and that seems to highlight the sort of lonely mood that I'm in.

People just out being people, so many just good with being themselves and a lot of them good with each other.

Sigh... I'm not even thirty yet and been through a bunch of just utter trainwrecks in well really just relationship attempts...and a bad marriage.

And yeah I'm getting why, I mean this all...finding Claire just sort of made everything make sense.

Sounds like it's all video brainwashing and stuff but I wasn't built for women, none of them stuck around and my little problem made me angry all the time until I got it, really got it that I've been blind to myself. Then stuff just...for the first time in what feels like forever inside I feel less like that I was circling the drain of being miserable and hateful.

But I'm kind of feeling lonely.

I park near Owen's Park near the community college and the lake there and watch folks from my car for a while and waiting for it to get to like actual night time then I get out of the car with my bag and slip my hoodie on too and just go for a walk dressed.

It's thrilling and scary and with all of that it feels like I peeled Hayden off like some suit of choking armor and I'm walking out and free for the first time.

I don't talk to anyone much.

I know my femmy voice I use won't pass. I mean it's kinda not a guy sounding voice but it's definitely a tranny like thing.

I even get some free punch that the firemen are giving out with a two dollar hot dog.

I get a hot dog and leave a twenty and let them have the change and just sort of blend into the crowds near the bandstand and watch the local bands that are playing tonight and sort of dance, more like half dancing because I've no clue to how to dance as a girl.

It's...it's fun.

I've missed fun.

I wander around not alone but not with anyone either or at least until I see this fight.

Well not a fight really two bigger guys that are kicking the ass of this other guy and this girl there watching and leaning against a truck that's all meathead tricked out.

The guy on the losing end isn't doing so well.

I take out my phone and snap a few picture using the flash and they freak out and I step behind a tree for cover and they hop in their truck and one of them yells at the guy on the ground.

"Stay away from Stacy you little fag she doesn't owe you shit!"

I'm going to say Stacy was the smug looking girl that was leaning on the truck.

I go over after they took off.

"Hey, hey...you okay?"

He groans bad and he's coughing and I kneel and sort of hover.

"Hey you okay?"

He shakes his head no...coughing and coughing and coughing.

Shit he's having an asthma attack I think.

I go through his pockets and find an inhaler in his jacket and shake it and put it to his mouth. He takes my hand in his and presses the thingy and inhales and then does it again before coughing less and then stopping and rolling onto his back.

"Hey...Better?" I ask.

I know my femmy voice isn't a girls but a very kind of drag voice.

He's still trying to breathe while looking at me.

He nods but he's still staring at me.

"It's not polite to stare."

He coughs a little. "Sorry."

I reach out and help him up and he's taller than me when he's on his feet. Six foot, six-one maybe, lean but not too skinny and...and I don't know kinda cute?

He's definitely kind of a geek though by the clothes he's wearing with the comic book shirt under his jacket and the sort of non brand name stuff that just says that he never got the high school deal of you are judged on what you wear.

I look at him he's going to hurt, he's bruising up a little already.

"So...what was that?"

He stares at me then his shoulders slump some and then looks at me again.

"A girl I thought I was into and was into me set her new boyfriend on me."

"Why?"

He makes a face. "Because I helped her through the semester with her grades and stuff so she could pass her electives. She was supposed to be into me...I thought she was into me."

"And she wasn't."

"No, she was still with her old boyfriend."

"Isn't there more than that?" I ask, I'm looking at him and he just sighs.

"Isn't that enough? Stacy...I liked her for years like since high school and I thought than once we were out of that bullshit things would be different."

"And they weren't?" I ask.

"Just a bigger game. She'd come over and pretty much act like she was my girlfriend, dressing sexy or like way less as the night would go on and eat my food and this whole damned game."

I nod. "So this came to this whole thing how?"

"After her finals she just blows me off, not like once but all the time. So I asked her what was going on and her big douche-bag gets in my face and tells me to fuck off that she didn't need me anymore."

I look at him, then where she was at. She wasn't upset, her big boyfriend wasn't forcing her to be back with him, she was watching with this smug look on her face as they were beating him.

"I take it that was tonight or close to it?"

He nods. "A couple weeks ago, it hurt so much that I made up a bill for her for tutoring. That...that pretty much led to this."

He looks at me again. "Sorry, I didn't mean to drag you into this or what this used to be."

I shrug. "I don't mind actually."

"Thanks..." He looks like he doesn't know where to go from here.

"I'm Claire." I offer him my hand.

"I'm John." He says taking my hand and looking at me then he blushes a little.

I smile. "Nice to meet you, how about I get you back to your place and fixed up."

"I don't...uhm...I don't live that far away."

I smile. "Is that an invitation?"

John swallows and nods. "Yeah..."

"C'mon my car's over there." I don't let go of my hand just shift my grip and lead him over to my ride.

"Wow, nice car."

"I make good money." I say using my keys to auto-unlock it and turn off the alarm.

"Oh...I suppose a girl like you makes good money."

I smile at him. "No my other self makes good money, I'm not really out yet."

He looks surprised. "You're not?"

"No, tonight was my sorta test flight."

"But you're so...girly...pretty."

That genuinely makes me smile and it feels like forever than I really had a reason to.

"Thanks, I guess it's just like nature or my real nature honestly. I mean...I was faking it for most of my life until I started getting who and what I am."

"Oh yeah...I guess I heard it's like that for trans people." John's still looking at me and I start the car and drive away from the park and following his directions to his apartment building.

It's an older building and has a small parking lot that looks like it's all student cars or people in that same money bracket and I park and we get out of the car and he's fumbling with keys as we head to a ground floor apartment.

Someone did some work on the place and it's okay honestly with new floors and decently painted walls and the place is actually really geeky in this kind of that's all he's got sort of way.

Sissyhalo
Sissyhalo
667 Followers
12