Making a Sissy Jock Pt. 02

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Mason, goes to Robin's crossdressed.
1.7k words
4.62
26.9k
36

Part 2 of the 3 part series

Updated 06/10/2023
Created 05/27/2020
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I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock.

I tasted him.

I got slammed with the realization I drank his cum and it was inside of me.

I sucked cock and drank cum and just like the sissy porn stuff said I liked it.

I was beyond freaked in going to the drug store and getting lube, Nair, the best razors I could buy, an enema kit.

And lingerie.

Part of my brain knows it's lame but I bought it at the department store as big as I thought "she" was and it was dark forest green satin with black lace.

I even bought extras in the panties, bras, garters, fishnets.

I was rock hard thinking about what was to come and seeping.

I wanked in the truck right there in the parking lot.

I shame cried too.

Then I drove home shaking, except a quick stop at the liquor store.

I had half the bottle gone before I got started.

Giving myself an enema to clean out my ass so Robin could fuck my ass was sissy stuff, humilifying, dirty, kinky, just so damned kinky and gay I was going to.

I wanked off again my cock rock hard thinking about getting fucked by him and then it was getting in the shower and using Nair to get rid of my body hair then shaving to get as clean shaven as I could get.

Getting dressed in the fishnets, the garters, the panties was torture and then the bra and the slip over that.

I fucking looked ridiculous but part of me just couldn't take it off.

Just couldn't.

So I threw on my tracksuit and I drove to Robin's house.

"Wow...he makes good money."

His place was a two story light cedar log prefab that was just offset in the woods from the street in one of the newer subdivisions in town.

I parked and quickly went to his door ringing the bell and he opened it and he looked at me.

"A sweatsuit?"

"Uhm it's all underneath."

"Never again, and you're going to be punished for that."

"What?"

He pulled his cock out. "On your knees, you know what you want."

I...

I shivered and sank to my knees and started sucking Robin's dick and again it was powerful, thick, huge and it was...good...just so fucking good.

I was deeply into sucking him before I realized he had his phone out and he took pictures of me sucking him and of my truck and his front door was open.

I was shocked and was going to pull off and say something but his freehand grabbed my hair and he jammed his huge fucking cock right down my throat and held me there as I bucked and heaved with the shock and the choking and the gag reflex and he literally held on until I settled and was breathing and panting through my nose.

And by the time my brain settled down Robin was fucking my face, fucking my throat and...and...and... just he was fucking my face!

In his doorway, the door open to the outside and he was filming it.

I came in my panties.

And that was just.

Panties, cheap nylon sorta satin looking but panties and other stuff and all of it was too much and I came.

I sort of bounced there as much as his fingers in my hair allowed as my hips pushes and I squirted a shocking load.

"Oh, look at that, look at you bounce, just like you're riding dick. I knew you were perfect for this."

He picked up his fucking and I lost my brain to the power of that big fucking thick meat and cockhead stretching my throat.

Fucking my face, hitting the back of my throat like he was humping my fucking brainstem.

I mean you could see it.

I know you could see it like I'm some porn girl getting gooned in the throat.

Feel it, that huge cock bulging out the flesh of my throat as he fucked my face.

Feel it like it was banging into my brain.

And I don't know if it was me being a sissy cocksucker or the lack of air I was getting but I stopped thinking and just became that sissy mouth.

I think I liked having my brain turned off like that.

I can't stop it and I can't stop myself when he pulls back until just his cock tip is in my mouth and starts flooding my mouth with hot salty, sweet, alpha spunk.

I got it all, drank it all, sucked all of it down for the second time today and feel it hitting whatever switch is in my head that is all sissy cocksucker.

When he's done he closes the door and locks it.

"Get out of those ridiculous men sweats."

I got up and got out of the sweats and my sneakers and the front of my panties are a mess and Robin looks at me as he slips his cock back into his jeans.

"C'mon, get your sissy ass upstairs."

He actually slapped my ass and pushed me upstairs.

I went but I was so scared, aroused, confused because never in my life I'd be this...crossdressed with cum filling my tummy and in sticky panties.

Robin's house was nice, well put together, there was some class to the whole thing honestly and he gave me directions to the master bedroom.

Big, with a big four poster bed and lots of like like wooden rungs in the head and footboard like he picked it out for sex with like all the possible handholds.

"Get on the bed, head down sweetheart, ass up."

He was...forceful, that personality just.

I've done so much already so I bent over and Robin walked around feeling me, touching me, seeing if I did things right.

Then there was him getting lube and pulled down my panties and started lubing my bumhole and massaging.

I moaned as he slipped fingers in.

Finger fucked me.

"You're clean, good."

There was more lube and then he grabbed my ankles and flipped my over onto my back hard and fast with a lot of strength that was impressive and he pulled and yanked me to him my legs off the bed and he lifted my cock out of the way and shoved his cock in.

"Ooooooh...aaaaaaaaaaaaaah!!"

I screamed.

That big, huge fucking cockhead streched me out painfully and pushed into my inside and kept going, inch after inch literally impaled me with all that size, girth, heat.

And I...me?

I shut off.

The straight guy I thought I was was just.

There was a switch flipped that clicked off Fag.

Sissy.

And that... "Ooooooh...aaaaaaaaaaaaaah!!"

Was the only sound I could make and then he bottomed out inside of me.

It was cock.

It was this huge cock and that plum side head pushing into my ass and stretching everything impossibly.

And that fucking thick, bottle thick, can't get your fingers around it shaft following.

Cock, pushing, pushing, filling, just fucking squuezing the straight jock out of me with it's mass and power.

Then Robin kissed me, hard, hot, passionate, with tongue, over and over as my insides went from screaming from shock to feeling filled, filled with hardness and heat and power.

Then he started fucking me.

And I screamed, cried out like it was the best thing that was killing me and it was as Robin folded my legs up higher, pop-stretched my spine and that huge cock began taking me over.

Sharp cries.

Whimpers.

Long moans.

Simpers.

Dominating me.

And then it happened.

Robin's cock hit my sissy spot.

His cock hit my prostate and like every sissy picture of it my eyes went wide and the bloom of pleasure inside of me and I inhaled.

"Oh fuck!, oh fucking fuck, oh god fuck, oh,oh,oh,oh,oh,oh!!"

I was chanting that stuck like a broken record or someone losing their mind.

And then he started fucking my sissy spot until it was too much for me and I screamed, cried, bawled, babbled at the pleasure and he fucked me just like that until I got harder that ever in my life and shot wild bursts of cum like never had in my life!

Robin buried that cock in me and stayed there and rode out my bucking body and my cumming and my wild insides.

Insides that fluttered, pushed, freaked out and molded around that huge cock inside of me.

That cock did this.

Cock did this to me.

Robin's cock.

Cock did this to me.

And when the spurts stopped from my cumming he pulled back then shoved all of it back in and fucked the last bits of cum out of me like squeezing a tube of toothpaste.

Then he started fucking my sissy spot again because that...all that just took minutes!

God he fucked me like that all over again until I was screaming just like before, sobbing and there were just little spurts but all that insane sissygasm pleasure, all the bliss and my insides...all that still happened.

The third time my useless dick just bounced and flopped and I whimpered, simpered, cried and moaned and sissygasmed all over again.

But the third time became my fourth and violently intense as Robin fucked me through my clenching this time.

Just fucking hammered and fucked me, hard, hard, hard, full length strokes over and over and over until he started to moan and I felt this full body screaming inside me need.

"Cum baby, cum Robin, Cum, cum, cum, cum inside me, please baby cum inside me, cum inside my sissy!!"

I ended there in a long pitch as Robin came and he was deep inside me but I felt it.

Felt his body tense, felt that cock twitch and shudder then it wasn't even subtle I felt him cumming washing my sissy insides with heavy spurt after spurt after spurt of super hot cum.

I sissied so hard at the fucking ending with being bred.

Bred.

Bred.

Made a sissy for life.

My brain is just running through all of this as Robin lets my legs down and darkness pulls me under into sleep.

Becoming as sissy, losing my cherry was so good but exhausting.

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doninpantiesdoninpantiesover 1 year ago

I dream that was my sissy hole.

AnonymousAnonymousover 2 years ago

whish this was me getting fucked made ne cum just reading

SissiboibrieSissiboibrieover 3 years ago
More PLEASE

Oh Sissyhalo1 you are amazing please bring on 3 asap.

Dratini2011Dratini2011almost 4 years ago

Part 3 please!!! :-)

TVFrannieTVFranniealmost 4 years ago
Nicely done!

Well, once again you've got my motor running! Between this story and "Making a Sissy Jock Pt. 01", you've made me fill two perfectly clean pairs of panties with sissy cummies. Can't wait to read more.

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