Amazon Sissy Jock

"Wow."

"But I have a condo in Vegas."

She smiles at me. "We can do this."

"We?"

"What can I say I'm a sucker for love. And you love Ryan and he was real tender with you after even as you are."

"Why can't I just be gay?"

She leans back and crosses her arms under her tits and looks at me. "Do you really want to just be some gay guy?"

"No."

"Notice how fast that was?"

I blush.

"Now we get started."

"Now?"

"Now, we start with shopping."

"Shopping?"

Tanya gets off of me and pulls me to my feet and passes me some panties. "Alright, first tucking."

"Uhm..."

She explains as she fondles my ball which would have gotten me hard but she killed that by stuffing them up inside of me and taped my dick down.

Then I was in panties tucked and dickless.

With a but plug in my ass.

And I liked it.

I didn't have too much time to get into thinking about that stuff as she took me to Ryan's bar and showed me how to sit and talk as she made drinks and took out pills and gave me some.

"What's these?"

"Blockers, hormones."

"Yours?"

"No worries I've lots, especially when I travel."

I pop them and wash them down with a drink and then we're shopping online with her credit card.

"I can't pay you for this, I'm not broke but I'm not rich either."

"It's a card Ryan gave me."

I look at her and she shrugs. "He really is loaded past anything you can get."

"And you took it?"

"My ass is worth it, I'm worth it, you're worth it too."

It was strange to think that but she went ahead and shopped online anyway. A skilled surfer for all things sexy and kinky she went to these online sex shops ordering clothes, slinky things, a bunch of corsets, dildos, but plugs and other things even this artificial set of tits with a chest piece and even some cock cages.

I squirmed getting turned on and could feel the plug in my ass.

Tanya looked at me. "Okay, time for you to get fucked again."

"What?"

"C'mon Chrissy you got into this and time to start breaking you of that dick of yours."

Tanya pulled me to the bed part of the room and between getting things and kissing me said.

"Mentally, emotionally you're still connected to your dick, I'm going to train that out of you by making every time you get horny it'll mean assfucking and sissygasms."

"Uhm..."

Tanya pushed me down on the bed. "Roll over."

I rolled over onto my stomach and she pulled my panties down and started playing with my buttplug.

My cock was still tucked and it was starting to hurt.

"It hurts, I gotta undo this."

"No, oh no, that bullshit will pass Chrissy."

"Pass...oh..." I gasped as she pulled the plug out of me slowly then there was more lube and her fingers that slipped inside of me. She knew right where to go, what to touch inside me and massage and rub.

My dick hurt so much but the pleasure was taking over.

I whined, I know I whined and she kept it up until my insides reached this boiling over sissy peak and I had a sissy orgasm and shuddered.

Again and again.

What dick? My sissy pussy felt so amazing, it felt so much more.

Literally as she sank into me with a strap on.

I cried out, I cried in pleasure and pain as my dick tried to get hard twice and she fucked that right out of me.

She was right.

I didn't need my cock, I needed other cock.

I loved this.

And I cried some too, there was this definite shock to my system as my body and brain was learning this. Something deep inside was flailing and dying off.

Tanya fucked me until she was tired and I was spent and boneless she crawled onto the bed beside me and wiped at my tears and kissed me a few times.

"Getting it now?"

I nodded.

We sort of cuddled after that a dozed a little before the housekeeper came in with these totes and Tanya grinned.

"The cool thing about getting local and paying extra for top shipping."

"That's?"

"That's some of the stuff we ordered. C'mon we are going to get you started and ready for Ryan like more than ever."

"I..."

I'm tired but my mouth went dry and my cock ached and everything plus there was this sort of ache in my ass...inside that wasn't from getting fucked by Tanya and her strap on but the memory of Ryan's massive cock..

We grabbed the totes and headed to the bathroom and once we were inside Tanya put on some tunes and grabbed a couple cans of pop for mix and a bottle of rye and her smokes and her purse with a pretty reasonable bag of weed.

She got me to run a bubble bath in the big tub and we started after a couple of joints and drinks. A long bath and facials, then getting my smooth as can be just to be sure and then it was fake nails, painting them and my toes and getting high and buzzed.

I...I actually liked this, the smells and getting clean, way cleaner than my guy days and inside and out and enjoying the soak.

Dropping the macho guy stuff.

Then Tanya got me to stand up and un-tuck and she started giving me a blowjob.

"Tanya?"

"Oh get over it Chrissy, this is the last blowjob, the last anything that you're going to get."

She went back to blowing me and she made sure I came hard and made sure I was clean and then it happened...she caged me.

It was glossy looking almost like rubber PVC shiny and it was pink.

She locked up my sissy clitty and pulled my balls into place with it too and that just happening made me shake and cry.

"Chrissy?"

"Sorry, sorry just really freaked out right now."

"I get that. But hon you'll get this, you'll more than get this you'll love it."

I couldn't get it up as she fitted me into this and now it's impossible.

And the sex I've been having.

"Okay, now the rest of it."

"Rest of it?"

It becomes this whole thing of us drinking again and getting into panties and then a corset which hurt a little and was freaky and then came my tits.

A silicone set of skin with big tits on it and smoothing it out and gluing it to my body then blending it all with my skin.

A blonde long tumbled sexy wig was next and even using the glue to holt that down too.

A sexy bra since my tits had dried.

Make-up was last.

By the time I looked in the mirror Chris was gone and Chrissy was there instead.

I looked like a tranny and not a real girl.

But I looked like a sexy, awkward hot tranny.

Like I was still big and pre-everything but the combination of everything made me look entirely different.

I must have stared there a long time.

Tanya slides next to me and gives me a one armed hug around my waist.

"Not a bad start."

"Start?"

"Oh honey you're just starting, hormones, the right shaping, working out right and dieting will do fucking wonders and then a little surgery like I got and you'll be really stunning hot."

"Really?"

"Oh fuck yeah, you've killer long fucking legs already."

"Oh...so...now what?"

"Now you go show Ryan and take him a coffee." She passes me a tube of lube.

I'm nervous as heck when I go and get him a coffee.

Part of me is sort of happy that I know how he takes it.

I know that and it's something I didn't have to think about it was right there.

And still the thoughts of the giant cock were in the back of my brain too teasing me to useless painful hardness as my dick fought the cage.

It was really off walking and I with me being nervous I nearly spilled some of the coffee as I made my way from his upstairs office kitchenette to his office.

Ryan stops doing whatever he was doing behind the computer and he looked at me.

"Wow, that's a change."

"I feel weird."

"Well maybe this isn't a great idea?"

"Ryan..."

He looking at me. "Look this could just be a thing, a one off something that happened at the party. Chris you don't have to do this?"

I take his coffee over and sort of sit-lean on his desk.

"Look Ryan this, this stuff I have no idea how to do this or be this other than how YOU make me feel. And Tanya's right."

"About?"

"That I've been in love with you for a long time but I had zero idea of how to show it."

"In love with me?"

I blush, really blush. "Yeah, and I'm not having some gay moment or stuff it's more than that. You're my best friend, you make me feel better just being here, being home. I couldn't stand you ex's. They never sat well with me even the ones that weren't screaming nutjobs."

"And now you want to be one of them?"

"You're not gay...and honestly until tonight, today...last night this wasn't even on my radar, we were not an option."

"And now we are?"

"I hope so. I'm not even freaked out by it like I should be. All I can think of is how attracted I still am to you and how scared I am that this isn't going to work."

"And you think we can work?"

"I really hope so."

He nods and smiles that sexy little kind smile he gets when he's actually happy.

With Ryan it's quiet, almost a private sort of smile.

"I hope so too."

He holds his hands out and I come over and it's so weird and strange but I straddle and settle on him in his office chair and he pulls me down to a gentle kiss.

It was really nice.

I was straddling him but Ryan was kissing me and his hands wandered and stroked my slinky-wear covered skin, caressed my ass and my cock ached as it throbbed in the cage.

We still kissed until I couldn't stop squirming because Ryan's cock was hard and that made my hot.

Yeah hot.

Turned on.

And as much as my caged dick ached like crazy so much of me was thinking of last time.

Of sucking Ryan's cock and that monster inside of me again.

I slid off of his lap to my knees and undo his pant's a pull the beast free.

Heavy, so fucking heavy and thick.

And getting harder, thicker too as I stroke it.

I kiss it.

Then more.

This is different than last time as I had Tanya there and I was a lot more drunk and lit than I am now.

So yeah even though the edge is off with my nerves I'm doing this because I want to.

It's so big.

The head alone is filling most of my mouth and I'm using two hands to hold and stroke his huge cock.

I suckle and suckle and use my lips and lick and tongue it and then suckle on it some more as Ryan gets more into it and he moans and groans and runs his fingers through my hair, he pushes me to deeper and more.

"That's it princess, that's it Chrissy, that's it caged girl, suck it, suck my cock, love it."

His voice was soft even sensual but still seductive and dirty, still commanding.

As his cocksucking caged sissy princess I squirmed as the thoughts and feelings made me harder like my dick was going to break off.

I squirmed whined and whimpered as he rode my face and holding my head and started feeding me cock.

It became all I could do just to breathe and hang on as Ryan fucked my face.

There's a thing in porn they call "cock-broken" and that's happening to me now.

It's the lack of air maybe making me all spun but it's so much more the sex act and that giving myself over to Ryan's monster cock as he's fucking my face. There's absolutely no denying the power, the size, the flavors as his pre-cum juices are mixing with my saliva making me mouth slick and drooling and there's no way to refuse what's happening to me.

There's a point where it becomes so real and overpowering that your brain just gives up and it feels good, it feels better than good it literally feels like his giant cock is fucking my brain directly as the head of his cock hits the back of my throat before going deeper.

My caged cocklette blows as I cum from that.

Untouched and locked up I couldn't masturbate to get off, I couldn't do anything but lets that power just take me over the edge.

Cocksucking throat fucked sissygasms are life changing and brain altering.

There's no way your brain can justify what's happening other than...yes...yes...this is what I was always meant to be.

My dick doesn't matter, my dick doesn't matter, my dick doesn't matter!

I hold his thighs and with all the gurgling moaning almost choking sounds I start shoving my mouth and throat back, hair flowing, fake tits bouncing all the way to where Ryan hisses. "I'm going to cum Chrissy, I'm going to fill you up...ugh...!"

I feel him swell and them he's unloading these thick heavy spurts of cum down inside of me and the thought is so powerful that my body tries to cum again and it breaks me a little more.

No, not a bad thing.

I think being cockbroken feels wonderful.

Ryan's cock slides out and I take hold of it to clean off every bit and every last drop milking it out of him and get lost in doing that mesmerised, floating, cock drunk and loving his cock, worshipping it, pressing that thickness to my face, nuzzling it until he gets hard again.

"Turn around beautiful, lean over the desk."

He called me beautiful.

I lean over his desk moving things out of the way carefully and I feel that huge cockhead at my hole and my eyes widen and I inhale a sharp gasp as that bug head spreads me wide and forces me open.

I grip the desk's edges and hand on as Ryan keeps sinking his cock into me.

"Aaaaah! Aaaaah! Fuck! So fucking big!"

"God Chrissy you're so tight, so fucking tight and deep, you can take it all, take it all baby."

Oh god he's talking sweet to me as he fucking fills me and transforms me.

"It's so big, so big, so big Ryan! Ryan!, Ryaaaaan!"

"God your pussy is so good Chrissy, so deep, so hot, so tight."

"Aaaaah! Aaaaah!"

It's moving in and out of me and turning me into this sexy, hard fucked cock filled sissy slut.

Over and over and over and Chris is just not a thing anymore as Ryan makes me spurt a little. I whine in a pitch I've never hit before. I can feel it inside of me, more and more when my sissypussy clenches around it.

And sissygasm after that.

Over and over.

My cock doesn't matter, my cock doesn't matter, my cock doesn't matter!

"Fuck me Ryan, fuck me, fuck me, fuck me, make me your sissy girl."

He speeds up and that giant cock is slamming in and out of me.

"Fuck me Ryan, fuck me, fuck me, fuck me, make me your sissy girl."

I'm repeating myself, as I'm getting dickdrunk, cockbroken and cumdumb.

"Sissy girl, Sissy girl, Sissy girl, Sissy girl, Sissy girl, Sissy girl, Sissy girl, Sissy girl, Sissy girl!"

He fucked me harder than ever as I said all that, babbled it.

I squeal as I'm rocked with another sissygasm.

I start to scream in just this long orgasmic wail as Ryan just is fucking my sissy spot edging me. The feeling is intense, past intense it's insane as it feels like I'm cumming and can't stop as Ryan's huge cock fucks me and keeps me in what feels like a sissygasm that last for ages.

Then he pulls me off the desk and into the chair and my body sinks on his cock bottoming out and my eyes roll back as I'm having another sissygasm that has him holding me tight as his cock fills my ass full of Ryan's thick seed.

"Not my sissy girl, my sissy wife."

He holds me there afterwards in his arms as I melt and lean on him panting and sobbing.

"Wife?"

"Yeah, wife. This, this is different Chrissy, the stakes are different."

"What now?" I ask him shivering as my body is still reacting to the fucking.

"We keep going." He pulls me down into a kiss and then shocks me by picking me up and carrying me to the bedroom again.

Tanya found something else to do as Ryan took me too bed and laid me down and kissed with me and we even nuzzled ach other as he played with my fake breasts enough for me to really want my own.

And when Ryan's hard again he sinks his huge cock into me missionary style and I'm so slick he goes in easy but he's so massive it still fills me until all my nerves are reacting.

I don't even try to make sexy sounds the coo of pleasure just slips out of me.

I'm such a bottom.

I like being a bottom.

Feeling like this, like I'm sexy and a girl.

There's more kissing too, much more and there's times when his forehead meets mine and we're staring into each others eyes and I'm falling for him harder.

I think he is too because he sees it in mine?

His eyes get softer.

He smiles more as we make love.

He stops inside of me when I sissy cum and my inside spasm trying to shoot off my load. Nothing comes out of course but my body still has to try and pump which seizes me tightly around that cock and all I can do is feel Ryan's massive cock inside me vibrating with tension.

It's like that two...three times before that brings him over the edge too and I feel the hot spurts of his thick cum boiling out and filling my insides.

We gasp, moan, hold each other.

We smile, laugh, kiss until we fall asleep.

I drifted off hard exhausted like I've never been.

My dreams were powerful, I almost never dream but this was dreams of sucking cock, making love, having breasts and being pretty and sweet and there was even me in a wedding dress.

Everything hurt when I woke up.

My insides hurt so much and so good because it was so intensely this post fucked hard, fucked twice by a monster cock thing.

My jaw and my throat hurt and I moaned and shifted and there were sheets stuck to me and Tanya was there sleeping looking like she'd been fuck wrecked too.

She opens her eyes. "Mmm...day?"

"Hmmm...what day is it?"

"Monday...yeah Monday."

"What...did I sleep the day away?"

"Pretty much...you phone went off your boss called at one point I said you were sick."

"Thanks...where's Ryan?"

"In flight, he had to go to some place in South Korea. His number's in your phone. He wants me to help you get moved in and things while he's gone."

Moved in.

I smile.

"This is real isn't it Tanya, him and I are really happening aren't we?"

"Oh fuck yeah. I think he loves you too or felt close enough with that and Chris that meeting Chrissy tipped him over the edge."

"Really?"

"He kisses you, he fucking kisses you and he means it."

I blush and smile but look at her. "You and him?"

"I'm his date, he brought me here as a girlfriend and a fuckbuddy. I'm kinda your placeholder Chrissy."

"You okay with that?"

She kissed me. "Hey who fucked your pretty ass before sending you to Ryan? I'm here for you too girl and I'm your friend and your sissy sister...I'm not some asshole guy."

I kiss her back and pull her into a hug and we do that for awhile just snuggle and hug and hold each other as we drift off to sleep for another while.

After sex recovery was like a hangover.

Getting cleaned up took time and effort and a joint shared with Tanya and a large chocolate milk over ice to boost my blood sugars back up as she gave me more hormones to take.

Using the bathroom afterwards was a trip.

Well you know.

But the soak in the tub was amazing.

New slinky clothes, tits back on, a freshly cleaned cock cage too over matching panties and I'm a happy sissy girl.

Honestly...cock broken sissy.

I don't think my dick will ever be a concern like it ever was before.

I called Ryan while lying on the freshly made bed.

I got his voice mail but he called me back as I napped.

I checked the number and femmy'd up my voice as I answered.

"Hey you."

"Hey gorgeous." he sounded like talking to me made him happy.

I blush. "How's Korea?"

"Muggy, crowded, lonely. It'd be cool to have you here but it'd be weird with you having to guy drag here during the day or hide."

"Yeah...this is real right? I mean not just some party thing?"

"Yeah it's real."

"And you want me to move in?"

"I want you to move in, I want everything about you Chrissy."

"Are we out?"

"That's up to you honey, seriously I have no worries about being out with you."

"So me not being there sucks?"

"Definitely, but the world's not cool to new trans girls. It's why I asked Tanya to stay and help you."

"Thanks I need the help and the company."

"Well despite how she comes across sometimes Tanya is a great person. It's why she's there in the first place."