Falling into Being a Sissy

We drink some more. "Can I do that?"

"Definitely. I want you to do that Sunshine. I want to see you shine like you've been doing and more."

I blush.

I blush and honestly kinda close to tears even it's that sweet and cool a thing that he just said.

People don't do that with guys, people have never done that with me.

Straight macho asshole hard guy culture is bullshit.

And I'm getting how much I've never had that is just simple stuff and nice.

Josh holds his hand out. "How about let's get started Sunshine? Let's get to know each other more."

I take his hand and he helps me off the couch like a gentleman and we both drink our glasses of wine together and he pours another and grabs the bottle and he takes me over to his computer.

We go through his playlists and we start choosing music together that we want to listen too.

He introduced me to this old Irish band called Simply Red and he plays. "If you don't know me by now." and he takes me out into the middle of the loft and slow dances with me.

I've never slow dance much in my life and never as a girl and doing that while being buzzed is kind of great, it's awkward but still really sweet and romantic and fun.

And I'm caught again at just how beautiful a guy he is and that he's actually a really nice guy.

Being held, dancing, swaying, feeling safe and sexy and liked.

Like actually liked.

And I liked the song and the kissing.

Then more songs and more wine.

Josh letting me look through his collection.

And some of his collection is his work under other tries and style attempts with different marks and signatures that he used because they sell better.

He's a good artist but he's smart with business too. He has to be with the house and everything.

We just talk.

And I learn about myself, about my opinions as Sunny with art and tunes and dancing and even what wines I like out of the ones that we've had.

It gets late and dark out and Josh lights some candles at some point in here and then rolls a joint and we slow dance a little more and sort of dance our way back to the couch.

We're kissing and it kind of hits me that we've been doing this for hours, just the two of us and that's the longest I've done anything like this in my life.

Well my old life.

I...

I am really loving Sunny's life right now.

Especially with the kissing we're doing even more deep level kind of stuff and with tongue and I definitely get excited, aching behind my cage which makes me want to get relief and he's getting so hard.

And I'm feeling it and rubbing him through his jeans.

I move and he moves him getting further back on the couch where I can unzip his jeans and pull out his giant hardening cock.

God I love this already.

And it's exciting and fucking delicious as I take him into my mouth.

Mmm...fuck yeah, sucking cock is great.

I was so meant for this.

He gets harder, longer, thicker and I get more and more into it as it does and I get tastes of his pre-cum.

My cocklette hurts in it's cage so much sending get fucked signals to my brain.

Makes me moan, ride the couch, pressing for the pressure, for any kind of attention there.

My jaw hurts and aches from his sheer size as I try and try to get as much in me as I can.

And buzzed, buzzed and again suck a nice watch.

Shiny, shiny and nice and...?

I sort of hazed out there as I must of got lost in sucking Josh's huge cock.

My excitement almost bubbles over as Josh's hands reach down taking my head, gripping my skull sweetly.

Yes, yes, yes baby take control over me plays through my head.

I get super excited I'm clenching my insides so hard trying to sissygasm as that massive plum head and huge shaft gets pushed deeper and deeper down my throat until going past my gag point and then what feels like into my brain.

I feel it part my brain pussy.

Literally feel it and feel the utter domination as my brain goes squish.

Wet cunt, brain pussy squish.

Wet mouth dick sucking sounds like cunt.

Wet cunt, brain pussy squish.

I moan, giggle as much as I came around the mouth and throat full

Bounce back and forth so excited and happy Josh's cock's nestled in my brain.

And I am happy because all the doubts just get wiped away.

"Relax Sunshine, just relax baby and enjoy it."

No girl that ever sucked Sonny's dick acted like I am. I'm not sure that any of them can feel like this, get off like this. I'm pretty sure it's a sissy thing.

I feel it so much and just when I thought the bliss was something that I might have been used to.

Josh starts fucking my throat,fucking my brain pussy.

Slowly, with this really nice pace that I can take making my whole self vibrate.

From my squishing brain pussy to my toes.

Slow steady brain fucking strokes.

Then pulling back enough that he's just in my mouth and he's smiling. "Suck it Sunshine, drink down all those mouth juices, love it, breathe baby, breathe, catch your breath."

I can't really think more than doing that and suck until my mouth is dry and I'm breathing normally then Josh sinks back inside my deepest throat and into my brain pussy again.

And we get into this whole pace, this whole sexy thing, this natural sissy and her man rhythm that is moving from this raw lusting needing as much cock as I can get to this becoming dear and sweet and intimate.

And oh god.

When he was getting close he was saying my name, caressing my head and losing his control at going slow and started fucking my face, my throat, my brain pussy harder and harder and I was pushing back, fucking him back shoving myself down his shift feeling that huge cock moving through my flesh until he pulled back so I could breathe and swallow all the juices my mouth pussy made and then he came.

Long, sweet, musky, manly, salty potent streams of cum into my mouth and I savored all of it as my pussy brain shorted out in the best of ways.

I cry.

I happy cry at how perfect this is.

No sexy has been like this, no woman could do this to me.

No woman could do this for him the way that a sissy can.

God, god, god I feel so fucking good, so right and sexy drinking that cum.

Sucking Josh clean and then until he gets hard again.

"Turn around Sunshine, drop those panties Sunshine and let me inside of you."

I turn around and I try to be sexy as I do it for him but part of me is vibrating.

My cocklette is screaming in caged hardness.

And that pain is telling my brain it needs cock in my ass.

"Fuck me Josh, please baby fuck me, fill my sissy ass."

And Josh gives it to me.

That big plum sized head pushes me wide open and I sissygasm instantly at the pleasure pain as that huge cock fills my sissy ass and pushes and moves my insides as Josh becomes the master of my body, my flesh, my heart, my soul.

"Yes!! Oh god fuck yes! Take me Josh, take me! Fuck me, make me yours!"

I give in.

Utterly.

It's not even falling into this anymore it's falling towards the real me.

Josh starts with the long full depth bottoming out strokes first making me cry out and moan and groan and cry happy tears.

Then he goes from those to that sheer brain melting strokes over my sissy spot until I can't control how many sissygasms I have.

I scream, cry out, vocal in how amazing he's making me feel.

Then the deeper strokes again.

How deep my insides feel, how I spasms and clench as I cum without spurting. This is better.

Something blissful.

I fuck back.

I want this, love this, want more and more and more as I fuck back.

Then the deep strokes become shorter deep inside me.

Josh going all the way inside of me as far as my sissy ass can take then he fucks my deepest core with these shorter five inch strokes that hammer away in my deepest parts until I'm squealing and grunting while I push back.

He'll stop and breathe when he's that deep and rotate his hips swirling his huge cock inside me stretching me more and more.

Then the shallow almost pulled out strokes, maddening teasing my insides.

Then more fucking my sissy spot.

Then in deep once more fucking my depths until Josh cums filling my insides with his seed, his love, his heat.

I fucking love, love, love getting filled with hot cum.

I'm sweating and bouncing and fevered and loving every second of it.

Through Josh cumming and coating my insides not once but twice.

Josh holds me close after his second load inside of me and we rest a while before he says.

"We should go downstairs and join the others, maybe fire up the grill and go for a swim."

"We have a pool?"

He laughs. "We have a pool and a hot tube and a sauna."

"Wow you're pretty rich huh?"

"It came with the house, which is why I bought the place. I never got to swim whenever I wanted as a kid."

I giggle. "Skinny dipping?"

"Of course, that's why the big fence."

He pulls out of me and we get dressed or rather just into underwear and I'm so well and deeply fucked and stretched and full of cum. It's really strange walking in the best of ways.

And I'm so fucking happy.

Then we do just that we have a late night pool party.

Music but not too loud. A lot of drinks and Josh fires up the grill while the three of us girls swim and use the hot tub just naked except for our cages.

We have fun, laughing and splashing and cuddling and talking.

It's mostly about Josh and me and the amazing sex and sort of a date we just had. And titties, we talk about titties and me growing my own out and getting implants. I want titties of my own. I really do, especially with the great titties the other two have.

And that leads to sucking and feeling each of theirs in the conversation.

We have grill veggies and some really good steaks. Not big huge cuts but really high end ribeyes.

Lots of drinks.

Swimming.

And more talking of me moving in. And coming out.

Which after we're plenty drunk we do online videos straight to my Facebook page.

We start with me explaining. "Okay everyone, I'm done. I can't like do this anymore and I'm coming out. I'm trans, I'm a woman and I'm going to start taking the steps in my life to be the real me. Sunny with a U in it, Sunshine. So here's where I've been. Taking my first steps with my friends and lovers and my boyfriend."

And we start with me going from looking like the old me to getting redone as the real me. Pointing out my lack of body hair, to getting dressed this time with not just the fake silicone titties but talking about getting my real ones and it's panties and they can see my cage under them but it's not nudity so it's not going to get easily banned and a corset, garters, stolkings, make-up and Becky even has a blonde wig that she fits on me expertly.

I do the whole thing in tranny sissy voice too.

Then once that's posted we go drink some more and smoke a few joints and take turns sucking Josh's huge cock again because well Toni wanted to and started and Becky and I couldn't resist joining in and we got all buzzed and stoned and fucked in our brain pussies again.

Dumber? Losing stuff from that? Sure like kinda.

What it did was take my mind off coming out or really giving a fuck for the consequences.

And cocksucking and brain fucking led to other horniness and well frankly brain fucking makes you not really feel how fuck sore I am too.

So we all ended up sucking and fucking with the dildo cock strap ons coming out and Josh joining in sinking his huge and loved cock into all of us. He doesn't even fuck us until he gets off but when we do, then he'll pull out and sink into someone else.

We do that until we're all well fucked and dead exhausted.

It's just us three girls when I wake up and it's plenty late.

And I'm sore and just fucked out honestly and don't do a damned thing until Becky moves.

She goes and gets our vitamins and starts coffee and we all start moving and getting cleaned up.

Then once I'm all clean I check my Facebook.

It's hard.

Between that and my phone and all those messages people are angry, pissed off, freaking out.

My family is freaking out.

And that leads to a fight on the phone with my folks over them being on speaker and Dad losing it because I'm talking in Sissy/Tranny voice. I mean I'm not even trying to and it's just the way I'm talking now.

And they don't believe that.

And they get pretty assholish about everything.

I'm not sure if me saying. "Maybe it's a side effect from deepthroating my boyfriend's twelve inch cock all the time."

Work left messages for me to use all of my sick leave and maybe get some help.

Hundreds of people dropped from my friends list.

Not everyone, but literally hundreds.

I'm hurt and upset and defiant.

And when Josh came home and inside with groceries I was very quickly kissing him and dropping on my knees and sucking his cock and getting him sliding down my throat and squish into my brain pussy.

Is it dumb to have that just rub out all the hurt and care and bullshit?

It's a relief.

And by the time I end up swallowing Josh's thick creamy load I'm better, happy and I just set all that old me life bullshit in the it doesn't matter places.

Him, Becky, Toni are really super supportive and loving that night.

We start settling in after all of that.

Josh has to travel so he helps me with some stuff before he goes off with some gallery deals and things.

Like getting my name legally changed with his lawyer and all of my ID's.

Selling my truck, my house or well waiting for them to sell, getting all my banking switched over to Sunshine Stevens or Sunny.

I take all my sick days and vacation time I'm owed and Josh and his lawyer were there to help get my pays switched over to my new name.

It was very clear getting fired would be a legal fight.

I'm going to quit anyways but I'm getting what they owe me.

They all help me clean out my house and give things away to new homes. A lot of my stuff I give to a local women's shelter.

Fuck Goodwill or the Salvation Army they hate people like me and make cash off of other people's charity.

My family came to try and stop us as we were moving stuff out.

But I wasn't alone and that freaked them out just like me being in my wig, dressed with a scoop necked top and jeans and all tucked away.

And talking like what folks think trannies sound like.

Yeah, still doing that. I mean I can talk like a guy but it's like my brain doesn't want to.

Anyways...that ended up still in a fight and Dad getting charged for trying to hit Josh with a tire iron from my garage and bashing our car.

The cops were called.

And yeah I wanted the charges pressed.

I'm not going to get into all of it but he said some horrible shit and mom did too actually. Though for a barely Christian family she went all super churchy on all of it.

All they made us do was get closer as it brought up Toni and Becky's bad memories and Josh took care of all of us.

Becky was right to the point of asking for Josh to let her suck his cock, because sucking his cock made everything okay.

And that's so true.

We sucked Josh's cock and took turns getting fucked in our brain pussies all night until each of us had a load of cum inside of us and in the process fingers led to finger fucking which led to dildo cocks which led to our usual.

And my life kinda started after that.

Hormones and dieting, corsets to get in sissy shape, exercise too. Lots of cardio and sissy stuff with the girls. Swimming, our Stepclimber machine, Stationary bike. The "Happy saddle" riding cock over and over teaching my body to love it and to also work out my sissy ass. All for a sexy ass. I want a sexy ass. I need a sexy ass for being a sissy.

Like emotionally the hormones started about nine days in.

Mostly getting teary and crying at sweet stuff or sad stuff on TV but mostly just laughing a lot more.

And I like think getting fucked is better too like it's always been great but it like just feels like a lot more natural.

And I'm pretty sure that cum tastes better.

Physically it went in stages.

My cocklette got much more useless first then after awhile the breasts started. First it was sort of moobs as I dropped weight then my nipples getting sore and sensitive and bigger. Then they started budding out and that changed my sex life entirely as I had small starter titties to suck on.

The rest...

Well that's going to come.

We're all going to Argentina for the winter. Josh sold some art for a good price and we're going for my surgeries. facial feminization, vocal chords, and implants too.