Waking Holly

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Jamie and Holly go away for the long weekend.
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Sissyhalo
Sissyhalo
667 Followers

It's been about a month since I told Holt, Holly the truth and moved her into my house. I never expected the side effects of what I did to her to be her to be her becoming a whole other person.

I know it sounded like that's the point but the point is that you changed them, bent them, broke them and made them worse.

And I fucking hated Holt, I really fucking hated Holt Thompson.

A long term bully, a spoiled asshole,

And now I fucking hate that family given things I've learned.

Because I'm falling in love with Holly.

It's not the sex but that's straight up amazing and I love that aspect of her that's exactly where I wanted her to go. Only she's gone further and she embraces that so much deeper than she would have or I thought she would have and she uses all the hypno like therapy.

I wasn't expecting a whole person even as affected by things like her, who is so damaged by her past that she uses everything that's the new her, that's Holly to survive.

I wasn't expecting Holly to have almost PTSD from being Holt and remembering the things that he did through new eyes that haven't walled stuff off.

I wasn't expecting her to be so broken by her old self and so kind of fucked up and abused by her old life.

I fucking expect it now because since her father went to jail for assault and he got out but there's charges and court for him to go to he and his family have been assholes.

I've been followed twice in town on my lunch break and I've seen them drive past our house too I think it's her brothers.

Holly dropped all of Holt's social media as his family and all his "Friends" turned rabid and the rumor mill worked into a frenzy at the scandal and fresh meat. It's funny how much time that frees up and how fast people start forgetting you and what you supposedly did when you don't have an account to follow.

It's leveling off for us too as we're not confronting them like they want us too.

I think her brothers are looking for a confrontation like that.

Instead what they're going to get with the cop as witness for us is a civil suit and a wrongful dismissal suit for her dad firing her from the dealership for coming out.

One they deserve that shit getting leveled at them and Two Holly deserves to hit them back for all the bullshit.

And she deserves to get her unemployment benefits.

Also surprise, surprise Zack knew a pretty decent lawyer.

Okay that was actually a surprise because this guy Peter actually did cases like this. A lot of folks that Zack knew weren't just druggies but folks with stuff going on like bogus claims of things at work from toxic workplaces like Tim Hortons up by the highway the place had a revolving door of staff but past that toxic workplace stuff the franchise manager was I guess a sexist asshole.

So that's going on and we're selling Holt's car since she had the papers but we're still fixing it up since it's an old mustang and it's valuable actually these days it's vintage.

And Zack knows a guy and him and I make a deal.

His mom is on a shit ton of meds and things and what most folks don't know that there are drug cards, these special authorization cards that a doctor needs to sign off on and you do kind of word it the right way so that the government auditors give it the nods and for a year some scripts get filled with only like a service fee of like ten bucks or so.

It's not all drugs and you still need your doc to sign off on them but it saves a few hundred here and there.

And I get diabetic stuff sent to the pharmacy all the time trying to get us to buy them so I gave him to give his mom lancets and strips for free.

So we're getting the car done for pretty much free.

She mostly is a home body right now and working on herself with dropping weight and letting herself transition and just setting in doing housework for us and gardening and working on herself.

She...she just tries so fucking hard now.

Holly cleans and she's into that, she loves keeping a clean house and doing it herself. She wears lingerie all the time too, by choice pretty much. Seriously the programming might have pushed the start on her girliness but Holly has her foot to the gas...in high heels.

That's another thing, heels. It's stereotypical but she does love her shoes.

I like her shoes too, not like a fetish but goddamn a girl that can do most everything while is heels is cock stirring.

Especially in lingerie, in corsets.

She does other stuff too that's to me pretty big things for her like teaching herself how to cook. She's a great cook too and for a former rich kid she wastes nothing we eat leftovers some, often she makes me a work lunch from them.

And she's getting more and more lovely, her waist slowly slimming, her ass is fucking fantastic with the working out she does for her ass and legs and to lose weight.

She's even got me working out for real and taking Enzyte...yeah the dick builder stuff. I'm not sure if that's doing anything except more frequent boners and maybe lasting longer but that could be the viagra or speaking as a pharmacist likely the better diet and working out.

She's trying, trying so hard to be "better" to be Holly and someone very, very removed from Holt.

And it's so hard to watch her tear herself down.

Actually it hurt watching her go through these Holt downward spirals.

Sarah used to get these hits of dysphoria and that really sucked when she had those. Holly has them too and she has this self hating almost abused hating her abuser relationship with herself and Holt.

It was too hard to watch her drowning in so I made her an MP-3 message like the first one but different.

I know it's such a messed up thing but...it is what it is and we started how we started.

So yeah I made this...

"Relax, Relax, Breathe, Be happy, Close you eyes, Relax, Be happy, Be Holly, Be Happy, Holly is a sweet person, Holly is a loving person, Holly is loving, Holly is brave, Holly is kind, Holly is gentle, Holly deserves to be happy, Holly deserves to be loved, Jamie loves Holly, Jamie loves Holly, Jamie loves Holly."

And she plays it all the time.

She plays the other ones too, Holly likes actually likes her sissy making MP-3 track.

But this one, this new one she takes with her, especially when she's going out or nervous.

Holly is getting better about going out.

Like I said she's kind of a homebody but I've been trying to get her out a little more.

So yeah four months in since Holly woke up and I'm going to try some things.

Work's been good and money's definitely okay so this weekend we're going away for Canada Day.

I rent a cottage out from Muskoka and that wasn't cheap given the rates usually but actually my boss knew a fellow that gave us a good booking.

I researched the area and found places to go see and things to do and headed home with a quick stop over at Lower Main Market which is actually a really old mini-mall that was smart enough to put their shops under one banner.

Holly texted me saying she's making meatloaf so I get a bottle of Beringer red and real flowers this time blue roses since I don't think Holly's ever seen them and the florist puts a single sprig of lavender and tied with a satin matching ribbon. I asked the florist. "Can you cut it long enough to have her tie it for her hair?" I don't think she thought of that either and she was texting as I left and then their bakery for cheesecake centered carrot cake cupcakes just four in a box but that really pretty made sort of thing.

Holly loves some bakery things, we burn it off and everything but before all this she never went and bought really good flowers never ate a chocolate croissant or a really, really good danish before.

She deserves better than the big box store things.

I want her to see a better world.

I never thought that someone like Holt would've been as boxed in like that until Holly started opening up to me.

Practice, practice, games and winning, old guy, old school everything but not in any good way. She never even got to enjoy college because of drowning in flunking and the shock of not being the best.

And coming home I think that drove them even deeper into that bastard don't care fuck everyone but me kind of asshole.

She's so damned different...and these days she makes my throat close with emotion as I think about her.

I pull into the yard and get out and I can smell supper from there. Rich beefy smells, something buttery too and something steaming and green and heady.

I slip into the house and she's breathtaking.

Honestly...six foot in heels, nice black stockings leading definitely to garters and a a dress semi short black but with this lovely hibiscus flower print on it a simple number but accentuated by her black lingerie...her corseted waist flares her hips nicely and that ass...it's getting so curvy and toned I'm stiffening just taking her in... Shoulder length blonde thick hair that brushes her collar bones now and a fair blonde face with simple make-up, smokey eyes and red lipstick to match her dress.

She's taste sipping sauce off of a spoon her lips looking sexy just doing that...I'm hard now.

Everything else...her height, the shoulders even though she's slimming down...the other stuff it doesn't matter.

"Wow...I think I should have gotten red roses."

She turns and her eyes light up in that happy to see me. That feels nice and so does the widening of her eyes at the flowers and things.

"Oh Jamie, they're beautiful!"

"I thought they'd be nice, be something new for you."

She comes over and she kisses met, soft and sweet and eager, I can almost feel her wanting to suck my cock in that kiss.

We kiss and sort of dance backwards to the counter and stove where we put things and she turns off the sauce and there's her laptop there for her cooking videos and a ton of things on the counter and the stove.

"You went out for groceries?"

She breaks the kisses. "I needed some things."

There's something... "You okay?"

She holds up her MP-3 player and smiles at me. "I am now especially after watching and letting it all wash out today's bullpoop."

I slip my arms around her waist. "Tell me?"

"It started with a kinda rude taxi driver calling me a tranny...he called me one pretty tranny though." She sighs. "I know I'm trans, I know who I am now and stuff but it just feels like really disrespectful."

"It got worse?"

"Hayden was around I think he followed me and he followed me into the market calling me names and trying to cut me off in the aisles. He grabbed my cart even and was swearing and stuff until I fixed him."

"Fixed him?"

"I heel gouged him in the shin and when he was hopping on one foot I took off a pump and slapped him on the forehead with it."

I grin and try not to laugh. "What shoes?"

"My blue platforms the two inch ones."

"Shoes okay?" I give zero fucks for Hayden or if he's okay.

"Yeah." She's grinning.

"That's my girl."

She kisses me soft and sweet and suckling. "Absolutely...Wholeheartedly...Devotedly."

Holly draws each word out and sinks to a crouch and unbuckles my pants and pulls my rock hard cock and I get painfully hard as she smells me, wraps red painted nail tipped fingers around my shaft and with a stroke she pumps out my pre-cum out and lets it drizzle on her waiting tongue like syrup and then she wraps her red pretty lips around my cock with this single sigh that says she wanted this, loves this, that this soothes her.

No one sucks cock like Holly, because it's more than just sucking cock, for her it's something important and that shows as much as the fact that she loves it, loves me.

And I'll tell you something all those girls, women with the face full of cum don't come as close to sexy as a poised, sexy, cum lover that can empty you of a load so god it hurts and then pack you tenderly back into your pants then kiss you and finish supper...crouched on her heels and not on her knees.

"Supper smells amazing what did you make?"

"Meatloaf."

"Smells better than meatloaf. So...tell me how you made it?"

She smiles lighting up and I start opening the wine.

"First thing was getting the oven going and I bought dark rye bread and cut it up and rubbed garlic over it like you see the fancy cooks do for garlic toast. While that was going I cooked up a little bacon and got it crispy then used the fat to cook two packs of mushrooms all sliced up then batch by batch onions, celery, and then two green bell peppers I roasted over the burners and a jalapeno. The rest was just hamburger and some steak sauce and salt and fresh black pepper I mixed it all up with the toasted garlic bread and then back in the oven."

I let the wine rest and get two glasses. "Sounds amazing what else?"

"Yukon gold potatoes that I boiled partway then as they sort of dried I soaked them in brown butter then when they soaked that up as best they can I steamed them the rest of the way then mashed them with salt, pepper and the rest of the brown butter and just a little cream."

She smiles sexily tasting her sauce again. "There's carrots roasting with the meatloaf and a side of steamed broccoli coated with lemon, butter, salt and pepper. I'm just finishing the gravy now which is lamb stock cooked until it almost went sticky in the pan then a few shakes of worcestershire sauce a shot of brandy and I've been bringing it back with beef stock to taste."

She offers me some on the spoon and she's getting so dainty, sexy in her movements too...even her hands seem like they dance sometimes.

It tastes awesome actually pretty high end. "That's delicious."

Holly beams. "Good! I'm making enough for leftovers so we can heat it like jou for sandwiches."

We set the table and we actually use mom's tablecloths and her good dishes. Holly's idea since they really didn't get used a lot that mom would have liked seeing us eat with all of this and make the time and money she spent worth it.

I kind of love that she went there with that and uses the things that we did keep.

I don't think I had meatloaf like that before all these strong flavors but all go with the plain old hamburger. "I think the kind of bread and the peppers really stood out."

She looks so happy. "It was all amazing Holly, though the potatoes were so good they nearly killed me."

I ate and had seconds and we killed the wine and I get up and kiss her and we both do the dishes together in the sink.

Holly is careful that the good dishes don't get damaged in the dishwasher so we handwash those as the dishwasher does the pots and pans and she put all the dining cloth in the washer as we're done so the cup towels and washcloths and table cloth and napkins get regular cleaning too.

After that I head downstairs to work some of the supper off while she says she's going to get cleaned up and take a soak.

An hour later I head upstairs and go shower while she's playing music and she's dancing in our room.

Four inch heels and pastel blue.grey stockings and garter belt with black lacy panties and a bustier corset that's pushing her boobs up and she's wearing this over and over loop of faux pearls she's playing with as she's dancing and swaying as she's singing along.

I'm instantly hard watching her.

She turns on her toe just really gracefully and sees me and she smiles.

We walk towards each other and we actually dance together a little and then she guides me to our bed where she uses the stereo remote to play this song called "who makes you feel" I think it's by Dido, she's into Dido.

She dances for me, lap dances for me.

Definite sex club, stripper moves.

"Should I buy you a pole?"

"Yes, please, please seriously I'd love a dance pole in the gym."

"Done..." I chuckle.

She traces fingers over my hard on.

"Yes, soon you will be handsome."

She dances a little more and all the way to that squat on her feet in heels as she pulls out my cock and wraps her lips around it.

She mouth-muffle-laughs with that happy sound folks make when they're eating something they love.

Everyday Holly gets better, more in love with sucking my cock.

And I stopped doing everything with her against her will a while ago.

She looks like she's caught in between prayer and rapture as she savors then swallows my cum.

She looks up at me adoringly as she sucks me hard again...fuck...she took those fake pearls and wrapped them in her hand to do this rolling thing as she strokes me and the feeling is fucking amazing.

Oh, oh Holly I'm getting you real pearls honey.

Once I'm hard again she moves to the corner of the bed and grabs the foot and she bends over in this really sexy way.

"Please Jamie fuck me, please baby, I've been a good girl, please, please I live for that hard big co...ck."

It takes little time to lube her and sink into Holly's ass.

Slick, hot, tight...her muscles relax on my way into her then ripple and grip on my pulling back stroke...I feel every inch of her insides...in she relaxes...then grips and over and over until she cums.

"Gnnnh...Oh Jamie, Jamie...lover...the best cock...I love that cock...feed it into meeeee!"

I stop as she shivers and her insides vibrate around my cock as her muscles spasm with her cumming.

"Up...on the bed."

Holly changes her position crawling slowing on the bed and I get on too, it's a game not to pull out of her as we move. Once she's on all fours she bends down into this yoga like downward facing dog ass up in this beautiful position that feels great and looks amazing.

I run my hands over her ass as I flex my cock inside of her ass.

"You're so tight Holly, such a perfect ass, such a perfect sissy."

"Mmmmm...you're bigger, I can feel it Jamie, thicker, I can feel your pulse thumping inside of me baby, I love this, I love this, thank you baby, thank you so much for making me your girl, I love being your sissy girl."

"I love you too Holly, you're my best girl, my sweet girl, my sweet sissy girl."

I start moving but I know her spot, the sissy button inside of her and start slowly and steady with full strokes bumping, fucking her spot until she lets out a long sexy moan then I shorten those strokes until I'm just moving in and out fucking her right there over and over and over.

"J..Jamie! Oh...Oh! Aunnngh! Jamiiiiie!"

She's getting vocal.

I love it.

"Fuck me Jamie! Fuck, fuck, fuck my sissy bum, fuck me! Remake me...fuck the stupid boy out of me, fuck that dirty masculine life out of me, harder! More! Please!...oooooh!oooooh! More cock! More h...hot...hard!...hard...god...I love cock! I love dick! I love your dick!"

I go harder until Holly's creaming in pleasure as I fuck her hard and fast with longer and longer strokes.

She's becoming everything I want and more...that ass, her body getting smoother, rounder, more femmy as the days have passed and the blockers and hormones have added that layer of girl fat under her skin making her jiggle just right as each thrust drives deep.

I'm moving her body with it and driving her against the sheets and pushing her tits over the fabric and pulling her back, it's just inches but it's over and over.

"Jamiiiiie...oh my titties, god my titties, I love my titties!...Oooooooh!...fuck me!"

Then over and over she's chanting as we're getting more into it, that fevered, sweaty, trance like sex.

"I love your cock, I love your cock, I love your cock, I love your cock, I love your cock..."

"I was made for your cock, made for your cock, made for your cock, made for your cock..."

"I'm your girl, your bimbo, you bimbo sissy girl, bimbo sissy girl, bimbo sissy girl, bimbo sissy girl..."

Holly's chanting this rolling her ass meeting my thrusts and rolling her head in this tranced out almost club dancing zoned out way.

"Made for Jamie, Made for Jamie, Made for Jamie...Jamie, Jamie, Jamie..."

Sissyhalo
Sissyhalo
667 Followers