Waking Holly

"Bimbo sissy girl, bimbo sissy girl, bimbo sissy girl..."

I bury myself deep into her and wrap an arm around her and pull her up, and up and off her knees and she sinks on me as far as possible and I bite her neck, nuzzle her ear and Holly turns her head and kisses me over her shoulder as I fill her with a load that nearly hurts blasting out of me.

This close I see her eyes widen, her pupils dilate and then get glassy then go half lidded as she cums in her sissygasm around my boiling cock. There's no Holt there anymore.

There's this deeper than crushing, deeper than attraction, deeper than anything look in her eyes there just for me there, she's just for me.

Holly has eyes that look at me so sweetly, strongly, deeply that it gets me hard again pretty fast.

I start removing more lingerie, her corset, unlock her cage and rub her clitty.

The cage is working really, really well with the hormones and everything but the cage holds things back, cuts down the blood flow it increases atrophy.

She's getting smaller.

Holly looks down gasping and twitching as I rub her clitty and giggles. "It's small, yay...! It's small!"

"You like it smaller?"

"I do, sissies have little clitties."

"Happy?"

"Yes..." She over the shoulder kisses me again. "And proud, I really do love this, me, changing, it getting tiny, it's the way it should be Jamie."

"Good...good girl."

We kiss again and I start fucking her again, upright both on our knees one hand on her breasts and the other on her clitty.

Holly's ass is slick, full of my cum and lube making it so smooth and I start focussing again on edging each other, those fast smaller strokes fucking her sissy spot so well, hard, over and over...these little catches in her breath between her whines.

Her chanting sexilly, breathilly.

"Happy bimbo sissy, happy bimbo sissy, happy bimbo sissy..."

I take her to the edge, me to the edge over and over stopping to play with her titties or her little sissy dick. There's no going back, it's too small, she could never reverse this ever, not even if she ever wanted to.

And given Holly's taken over her training that will never happen since she's even more hardcore than I was with her.

How much though she wants this, loves this, chants stuff like that...So, so hard on inducing.

She's moaning hitting higher pitches and getting non-verbal too in these long little wails and whines...I feel her tiny sac tighten.

"Hold it, hold it baby..." I tell her.

I pound in harder, thicker, hotter strokes... "Hold it Holly, hold it...I'm...I'm cumming with you."

"Aaaaaahhh...ff...fuck...please Jamie..cum, cum in me, flood me...breed me."

That's all I need and I drive home into her sissy spot and start cumming and flooding Holly's insides making her scream out loudly and she cums a single strong little spurt in my hand and she sobs after that... "Squirt-sissy--squirt-sissy...oh..oh fuck...both...both..."

She must have because as tired as I am she's going limp and boneless in my arms.

This was some of the best, hottest sex we've had.

Then comes the better part of things and that's the post everything curl up and cuddle...wrapping the sheets around us and I drink in her smell as we spoon and I wrap my arms around her and hold her tight.

That for a little while as we just soak in being us and cooling down off some of that semi-frantic sex.

Then there's little kisses here and there and I eventually roll her over so we're facing each other and kissing slowly and more intimately.

"I have a surprise for you I hope you like it?"

Holly's eyes light up. "More!? Jamie you're spoiling me."

"You're worth spoiling Holly."

"But you do it all the time Jamie."

"Well I'm in love with you all the time Holly and you just...just move me, you try so hard all the time."

Her eyes have that shine of happy tears there and I kiss her. "I got us a place for the long weekend."

She looks surprised. "Oh...oh wow really like...what?"

"I rented us a cottage up at Muskoka."

Her eyes got big. "No way."

I laugh. "Yes way, actually it's out of the way so we'll have some privacy for fun and there's a bunch of toys there for us to use while we're there and I'm told we'll have a good view of the fireworks from the water."

Holly hugs me. "I can't believe that we're doing this! OMG! I've never been cottaging!"

"Really I'd think that you would with the cash your family has?"

"Oh heck no, Holden has a lake camp he bought when he started working for dad but us...the Family. No, we went on big vacations that Dad could post pictures up and brag about and everything like Aruba and Cuba and Disney when I was little..."

Her voice trails off and she gets quiet.

"Holly?"

She sighed. "I just realized how much of my childhood was advertising."

"Your Dad's an asshole."

She does this sort of sad nod and shrug. "So was I...was Holt...when he was older...he was not a good person, especially to those poor local girls."

"Well you're not him...trust me I look into your eyes everyday and all the time and Holt's gone..."

She kisses me and snuggles. "Tell me more, tell me about our getaway."

I hold her and she's doing that brought herself to hurting because of Holt's bullshit...her old life kind of snuggles.

I get my phone and I'm telling her about it but I have things for there on my phone and bookmarked so we look through and see the different things and places and she slowly comes out of the the funk as she's starting to find that this will be way more about her and all these first for her.

A really big step in her new life and for our relationship too.

We end up falling asleep while sort of talking with what we're going to do and my phone alarms wakes us pretty early.

We actually skip the usual morning routine except the breakfast shakes in favor of getting ready and on the road.

I look at her. "No corset today hon, none of that other stuff we're going away and winding down."

She bites her lip. "But I like all of that stuff?"

I look at her and smile. "Well I was thinking we adjust some weekend doses in your hormones but you just let everything go for the weekend and eat and drink whatever."

"I'll get fat."

"Babe, you want fat for like other parts right? So a full out long weekend and build up some reserves, some of those curves...after that you can work them down later."

"Oh...Well I never thought of that! I would love to round out my ass more and like totally feed the girls." She was staring at her boobs and smiling.

We start with upping her hormones and her progesterone some more and after that we get dressed pack some things and we head out to the car rental place where I rented us a nice fully loaded mini-van and then we go for coffee at one of the indie places in town and she gets a lot of stares as we ordered and bought some churro bites.

Holly's actually still something to look at...okay her shoulder and some things but still her hair's grown out even longer and the hormones actually help her with that and she is good at doing her hair.

Sun hat with ribbon from the roses tied around it and she's wearing tight jeans with a cropped top and it's low cut enough to just show her very flat stomach and thanks to her corset training she has curves and she's kinda just showing the top-back part of her panties and you can definitely get glimpses that tell her decent sized B cups breasts are going braless right now.

Someone might get that she's a trans woman but a pretty one, Holly definitely can pass for a strong looking girl.

And she's wearing sandals too so she's not towering over folks.

I know, I think there's people that know Holly was Holt.

Good.

I want that honestly.

I want them to get just how different she is now and how that people can change.

I want assholes like Holt used to be to think that for all the jockness and bravado and macho bullshit that they too might end up a pretty, sexy, cock loving woman and I hope that scares them.

We leave and drive and drink coffee and casually nom on things until we get to the mall and do some shopping for cottage wear. It's shopping so Holly's both nervous and happy especially as I don't stop her from getting whatever she wants.

And that's a fair amount of stuff and granted it's expensive but it's literally things we don't really have like beach bags and towels and all the things that you should have while going out for something like this as well as clothes for her and me.

"We should get our groceries here. The summer BBQ prices will be bad enough here but up there it'll be cottage high." she says.

I kiss her. "That sounds like a plan beautiful."

We just go to the SuperStore and it's most fruit and veg but there's meat too for the grill and we go a little all out with that with some custom cuts and all but we spend more on the booze with us getting wine and vodka and some beers and coolers and we load up and we take off driving and playing tunes and yeah that's mostly her music and everything.

We stop here and there looking at interesting things that are on the way and that's from little roadside stands to things that just look nice.

I get some really nice pictures of us together at a spring that comes out of the rock on the side of the road where someone built a little cistern. And the water tasted really good so we filled up our bottles too.

There's another set of pictures with her standing in this really big patch of wildflowers under some maples and they're up to her knees and things so she gets changed and we get some pictures of her in a sundress and then we do one set of her with the sundress fallen down around her waist exposing her breasts and another one like that with her holding a bouquet of flowers.

We keep the flowers and she's thrilled with the pictures.

I am too actually and not just the part nudes though if we do prints of those some should definitely be in black and white.

Holly after that gets a blanket and lube and things and we make love out in the wildflowers and the sunshine for the first time.

It's the first time I've done that outdoors and the same for her and she's vocal and she's happy and she's crying, good tears.

Even laying there on the blankets afterwards we're catching our breath and she just has her eyes closed and tears leaking out the sides and she's smiling and stretches out in the sun for awhile.

I pick all the flowers we trampled under the blanket and take them with us.

Then we're back on the road and yes we're taking the longer non-highway route and everything so we're taking a much longer trip but we're having fun.

And we pretty much stop at most places one for the bathroom because trans girls have to go more.

Plus it's just looking around too.

We buy things at these places too. Strawberries mostly as they're ripe and local and in season we get three pint boxes because we eat one feeding each other in the store. I get a whole stack of newspapers and we get gas and ice cream and while she holds the ice cream I take all those wildflowers and press them in between the newspapers and set some of our things on them to weigh it all down.

And I get rewarded with Holly looking at me like her heart's breaking in a good way.

And I learn that french kissing is a way fun way of sharing ice cream.

We do that all the way to Muskoka and we go to the cottage first.

"Let's get unpacked and take stock and see what we're going to need if anything."

She nods. "Sounds like a plan hon."

It's a quick stop at the renting office to get the keys for the place and then we're off.

We get there though it took longer than I thought and oh...oh yeah it's worth the money I'm paying with there being a nice cabin and a pretty modern one and there's a nice deck in the front and in the back a big patio that literally leads to a dock and there's two jet skis there and a canoe there too waiting for us

There's even two quad bikes there in a garage for us to use the trails around the camp if we want.

Yes I paid a lot of money for this weekend.

Well the credit cards are paying for it but you know what I mean this'll be the likely one big thing for us this year aside from Christmas.

Inside the cabin is well done, very clean and worth the money and it's homey if small.

Holly's looking through everything and she makes a list and she's very obsessive with the list looking at it a lot, checking it a lot.

"Holly? You okay?"

"Hmm what?"

"You keep checking your list."

"Oh, yeah I do that, if I don't do that I forget stuff."

"Since when?"

"Since always...if I don't stay right where something is or something I kinda get lost in other things. I have to literally like be on top of stuff to get it all done or like be doing something that's got like a lot of stuff going in like one thing."

"Okay..."

She shrugs. "It's me, it's why I flunked college and why school was always so hard. I just could never get that stuff, just couldn't focus on like books and just sit there and do all that stuff without going nuts. I learn better from videos and people telling me and engaging in stuff."

I look at her. "Holly...that sounds like you have ADHD or ADD."

She looks at me and she smiles a sort of sad smile. "You think?"

I look at her. "What's wrong?"

She looks at me. "If it is that then that just...I'm a Thompson. We'd never be allowed to be like that."

"Your father?"

"Dad, Grandpa...I'd never have been allowed to be less than perfect."

"You okay?"

She gives me this sad smile and nods. "I will be." Then she puts on the headphones and turns on the MP-3 I made for her.

She might be alright but I'm not.

I fucking hate Holt but what if a whole lot of everything that made Holt the rabid asshole he was...not his fault?

We get back in the van and we drive into town and we stop to get a few things that Holly has on her list like a pitcher and some vases and I make a call and I get a script filled for Strattera a non-stimulant ADHD medication and I get her to take two to start her off.

We walk around pretty much and we hold hands and we're getting looks but not that many looks because of things like Holly being trans. She's scared though, this whole revelation actually might have thrown her because she's holding my hand pretty tight even though she has her earbuds in and everything.

Shopping takes things off of her mind some with us checking out the local candle making shop and buying some and there's a glass blowers place too and all these little curio shops of things and we get some things here and there but we stop and we get a local ice cream made big chocolate milkshake to share.

I have no idea if the chocolate thing is psychosomatic or if it's a hormonal thing but that definitely seems to help her out and so does us holding hands and walking the dock there and watching the boats and we even see the one of the restored steamboats that they advertise.

We head back and she kisses me. "Grill something Jamie for supper I'm going to go and shower and stuff."

I get the grill going outside and I'm not a great cook but I take out the steaks and I use a pair of scissors to chop up some rosemary and then add olive oil and lots of salt and pepper to the steaks and let them sit and do their thing while I make sure the grill is good and clean before putting them on.

Actually I grab stuff she bought for a salad too and just...toss stuff on the grill for a few moments like the romaine and things just to get a few marks on them and the peppers too the rest is pretty easy with cucumber and tomatoes and a little onion too and I make that salad.

Hell after I check on her and she's on the bed watching the videos she's saved on her laptop and drowning out things while listening to the MP-3 player I leave her alone and I cook all of supper.

The steaks will be last so I did the salad and I take some of the strawberries and just mash some of them up with sugar and I start in on the watermelon too. Some for later goes in the fridge but some get sliced like pie wedges with the rinds cut off and the strawberry mash between.

Kind of looks like a cake wedge when it's done.

I make a pitcher of sangria with some of the strawberries and some lemon slices and some of the wine. A bottle of the red we brought and I added some of the vodka too for some kick and it's cooler out here on the lake so I go and I get things ready by checking out the gas fireplace and I set out a lot of the candles we bought inside and I light them and I put on my MP-3 player with the stereo they have in here and go to start the steaks while Eric Clapton's "Wonderful Tonight" starts playing at a pretty good volume.

Table set, glasses out, candles on the table but other places and I'm grilling the steaks as she comes out from the bedroom and she's looking around.

She brings her hands up together over her face and she starts crying.

I smile at her. "Feel better?"

She's staring at me. "A thousand times better...god Jamie I love you...I've never had this, never had this once in my life...ever."

I set the steaks off to rest and go over and I take her hands away from her mouth and I kiss her.

"I love you Holly, all of this is for you because I love you."

"No one's ever loved me before Jamie, not really, not ever..."

"Well from all of things we know you have never had the chance to be the real you...I want the real you Holly."

She kisses me back. "It might sound weird given how we started but I feel more real now than I ever have before Jamie and it's all because of you."

We dance a dance before I seat her for supper and she stays seated for a minute before she gets her purse and her phone and takes pictures of things before blushing and smiling at me.

"Sorry, I just want this memory like forever."

We eat and it's kind of funny how she makes such a huge deal out of me cooking.

We do the dishes and drink and clean up and drink some more and we dance.

Then Holly guides me to the couch where she does a lap dance and eventually drops her dress and I'm really hard and she sinks to her knees and takes my cock in her hands and smells me, licks, kisses the shaft, kisses the head, sucks on my balls.

Whispers. "So perfect, so happy."

Her eyes close as she sinks her mouth over my cock and there's this look of sheer bliss on her face.

Oh yeah Holly, this is you, this is the real you.

It's a long, slow, sweet blowjob and even as I pump a load into her sweet mouth she's slowly savoring it and keeps sucking me driving me nuts as she gets me hard again.

I turn the fireplace on and we get in front of it and she's on all fours as I sink into her beautiful ass.

I love how she moans, coos even as I sink into her...Holly's insides flutter as she squirts immediately gasping.

"God Jamie, God I love this. I love your cock, love you inside me."

"I love you Holly, your ass is amazing girl...so tight, so fine."

She's already lubed herself so I sink in easy.

But god her muscles inside of her. And she's so aware of them, so practiced.

Holly moves with me but works her ass like a goddess.

Relaxing and moaning sweetly as I sink inside and then she clenches as I'm pulling out and her ass holds me so tight it's making me feel every inch of her sweet insides.

Even though she squirted she's so much more into getting fucked, getting off like a sissy.

"I love this Jamie, I love this, fill me with that big cock, more and more. I was made for you cock."

I love the way she says these things, even as we're fucking it makes me feel harder.

But I shift my strokes. This isn't just about sinking my cock in her. I want to take her to that place. I shorten my strokes as I nudge her sissy spot and she moans then I start doing that doing her like that over and over until she's cumming in a sissygasm.