The Telemachus Story Archive

Cracking Chris's Cherry
By Cracker
Email: gelded_alpha@outlook.com



Cracking Chris’s Cherry

By Cracker

To my buddy and fellow writer, Khalid, for his input.

Opening:

There's a lot of good guys on the Internet, and then there's some who are all ego. The type of guy who needs to be taken down a peg. I like to ‘break’ them in a cybersex setting. Basically doing a job on their smug self-image and ego. The following was how I did one on a guy called Chris.

He was just my type. Well-built, good looking, and a self-proclaimed stud. As arrogant on the net as he probably was in any gay bar. We had chatted a bit. As I listened to him boasting about his conquests on cyber, I decided it was going to be my aim to bring him down a notch.

Now the one thing that helps is when the guy in question thinks that he's a total macho top who isn't scared of anything. The way to get them is to make it look as if you think they're scared to try something. Rather than lose face or “wimp out” which, would ruin their self-image, they insist they are not. I make them prove it by promising to try a sub role play and add the clincher, ”unless you are afraid you’d enjoy being submissive in our sex play. Yep, no matter how much they insist they wouldn't like it they know that, if they back out…well, you both know what it would look like. In the end., not willing to look as if they're scared of your challenge, they agree. Then you've got it.

Now we have been chatting a bit, so we were comfortable with each other. About two weeks in, I've decided to go for it. He was doing his usual boasting about who he'd scored on; the guys that he had totally turned out as bottoms. He'd had one or two drinks, so he was pretty loose. He thought I was drinking, but I had my eye on something bigger than a drink. I brought up the subject of cyber role play. He was hot for it. I decided it was a good time to toss the grenade.

It begins:

Breaker
So, you ever been on the sub side of the cyber?

Chris
I don't think I'd be into it honestly

Breaker
You might like it

Chris
I don't think I'd be into it honestly

Breaker
Never know until you try, but I mean if you are scared to try then it's cool

Chris
Fuck you. I’m not afraid ok...just know I'd suck at it
I’m simply naturally dominant

Breaker
Yeah then it shouldn't affect you much after the cyber ends right

Chris
Following orders won't get me hot.
I’d be fighting it to keep my dom side down
I’d suck at being a fag in it
I’m just being honest

Breaker,
Well if you’re worried you’d like it too much then we don’t have to

Chris
I’m not scared

Breaker
Haha I see I see

Chris
I’m just being honest

Breaker
Seems like you are pussying out man ; too worried?

Chris
Shit I don't pussy
Don't think I’m backing out or shit cause you worry me

Breaker
If you ain't a pussy then give it a try
You won't back down from a challenge right?

Chris
Fuck it...you're on
So, how do we do it?

Breaker
Haha good ;good
(GOTCHA)
Let's think up of a scenario

Chris
Ok
You’re in charge in it
So whatever
I’ll suck in it but won't pussy out
So how do want me to play it

Breaker
I want to see you play it out like one of those subs who goes up against a master
First thing you can do is start with calling me sir.

Chris
Hello sir
This is too weird

Breaker
I know you are total Dom, so you won't pussy out from this challenge

Chris
Ok but just tonight

Breaker
Fag one more time. You can do is start with calling me sir.

Chris
Ok Sir

Breaker
Good faggot
Tere jaisa kutiya pehli bar dekhra hu
(I’m seeing a bitch like you for the first time)
or (for the first time you are acting like a bitch)


Chris
Huh?

Breaker
Just goofing with you. I saw your picture when we exchanged them. I see you are a muscled man right? That's how you have...or had such an alpha build

Chris
Yes Sir

Breaker
Why don't you tweak your nipples for me

Chris
What!

Breaker
Backing out already. Pussy

Chris
No I’m doing it. Yes Sir

Breaker
Give em a good slap, bounce your pecs and do it fag
Tell me how it feels

Chris
Fucking hot actually …Sir

Breaker
Turned on maybe, boy?

Chris
Ah. Turned on yeah

Breaker
Think about how it would feel if I was right there behind you, rubbing on your chest, pushing my bulge on your ass and playing with you
You forget to type sir, faggot.

Chris
Sorry sir. Yeah it would be hot

Breaker, 1:00 PM
Remember your place

Chris
Sorry Sir

Breaker
You promise to do whatever I want as long as it doesn't cause you hurt, eh fag? That includes no climaxing unless I approve it

Chris
Yes Sir

Breaker
If you cum before I give you permission it means you’re a pussy. Agreed.

Chris
Yes. I promise. Don’t worry I can hold off blowing. Not a pussy…Sir

Breaker
Not good enough boy
Reply in all caps, louder like you mean it.

And work those tits

Chris
YES SIR I PROMISE
Fuck my tits are hurting.

Breaker
And change that to yes master. Not sir.
Like a good obedient faggot.

Chris
YES MASTER

Breaker
You feeling hard boy?

Chris
Semi-hard Master

Breaker
(1/2 way there boy)
Keep working your tits. What's one thing you never thought you'd do as a sub

Chris
Shit, my tits are stiff
Act like a bitch

Breaker
Give them another pinch and this time moan like a slut

Chris
Yes Master...fuccc

Breaker
Your hard?

Chris
Yes Master

Breaker
(Good)
Don't touch your cock-let for now
Want you to push your tits up to the monitor as if you are offering yourself up to me, both your nipples in between your fingers and twisting them both roughly. Turn on your speaker so I can hear you.
Moan for me chut

Chris
Ok Master
(moaning heard)

Breaker
Now give your ass a hard slap
You are gonna be a total bitch for tonight

Chris
Yes Master
(Slapping sound and gasp heard)

Breaker
(Fuck I took a chance and he complied)
How's that ass feeling boy?
Rub your fingers down your crack too

Chris
My ass is on fire Master, but my cock is throbbing

Breaker
Good boy.
(He’s hard now just needs to be high)
Relax and have a drink before we continue
Make it strong

Chris
Thanks man I need one. My butt and nipples are red

Breaker
It’s Master, fag

Chris
Sorry Master.

Breaker
I'm gonna have you fuck that pussy hole tonight

Chris
Shit. Yes Master

Breaker
OH look at you, you thought you wouldn't be a good sub
But here you are slapping your fucking ass too
No coming unless I permit it

Chris
I keep promises…Master

Breaker
Still behaving like a proper pussy
Has me rock hard

Chris
Me too master

Breaker
Want you to pull your underwear down
Get naked faggot

Chris
Done sir

Breaker
Put your legs up on your table, spread your fucking ass wide open

Chris
What the fuck?

Breaker
Backing down on that promise huh

Chris
No…done Master

Breaker
You can touch your cock with one hand
Want you to pull your underwear down . Get naked faggot

Chris
Done Master

Breaker
Keep your legs up on your table, spread your fucking ass wide open

Chris
Done Sir

Breaker
You can touch your cock with one hand
But stick the other fingers first into your mouth

Chris
Master

Breaker
Get it nice and wet

Chris
Done Sir

Breaker
Done what faggot?

Chris
Sucking on my fingers

Breaker
(Buzzed and boned…got you)
Sir or master…got it pussy-boy.
Slap your ass and tits to remind you
And apologize to your master

Chris
Shit that hurt. I apologize Master

Breaker
Do you have poppers?

Chris
Yes master. Why?

Breaker
Take a good strong whiff

Chris
Not sure about that bro

Breaker
Backing out again? Figured you'd be a wimp

Chris
No okay. Just one hit

Breaker
Good fag.

Chris
Fuck. Done Sir

Breaker
(now to press, keep him high and not thinking except on his need to cum)
Oh yeah. now stroke that cock-let of yours
Want your fingers on your ass

Chris
Yes Sir

Breaker
Take another good hit. Don’t pussy out boy

Chris
Done. Fucking my head.

Breaker
Gonna fuck you up boy. My brown Indian cock up your faggot ass

Chris
Yes sir

Breaker
If you gotta loosen yourself up more
Then take another whiff

Chris
No I’m good

Breaker
Changed my mind, that's an order, faggot.

Chris
Okay but just this one more time okay, Sir. I’m wrecked right now on stuff

Breaker
Yeah we will see about that
Make sure your sniff in hard
Take another deep whiff and then insert your fingers in

Chris
Yes sir
Fuck my finger is in my shitter

Breaker
Yeah faggot?
How's your pussy feeling

Chris
It’s tingling
I haven't pushed in too tight

Breaker
Need a man's cock up your ass don't you?
Say it faggot

Chris
The fucking shit …the poppers
I’m so hard

Breaker
Another whiff Chris
Relax yourself up for more
Cracking you up pussy boy

Chris
I’m flying man hahaha

Breaker
Fly Chris.
Push those fingers in now boy
Fuck yourself for me

Chris
Shit slipped in good

Breaker
Your pussy loosened up now ?

Chris
Uhuh

Breaker
How are you feeling faggot

Chris
Fucked up and I’m leaking like crazy

Breaker
Push into your chute deep. Taking your ass faggot.

Chris
Yea you are

Breaker
Making you into a chut…that is Hindi for cunt. You’re my cunt tonight right?

Chris
Yes Sir

Breaker
(Yeah pushing fast not giving any time to think)
Fucking right you are.
Yeah fuck yourself deeper

Chris
Fucking hell my hole is feeling it

Breaker,
Wanna hear you say yes sir as you fuck yourself

Chris
Sir. My ass is on fire
YES SIR

Breaker,
Louder boy. Who's ass is it?

Chris
YOURS SIR

Breaker,
Good.
Now fuck yourself harder and edge that punk cock
Make your pussy fucking wet boy as you edge
I want my chut leaking and in heat
Imagine if your subs could see you right now?

Chris
Fuck sir. Master…whatever

Breaker
Legs spread, ass on fire with your fingers shoved in deep

Chris
FUCK YEAH!

Breaker
(okay bring him off like a bitch)
Moaning for this Indian Dom

Chris
Fuck yes

Breaker
You forget your place faggot.
I want you to say Sir
I want you to say it right now
"It's your ass SIR!"

Chris
It's your ass SIR

Breaker
(Got him..he can’t take it back)
Top Dom alpha giving up his pussy
Fucking you now boy
Taking your ass

Chris

Shit so close to losing it Sir close

Breaker
Don’t come yet unless you admit you’re a pussy

Chris
No pussy..won’t come

Jabber
Go deeper and harder. Slap your fucking cheek while you do it
Spank yourself cunt
You boned up like a bitch in heat
Type it

Chris
I’m boned like a bitch in heat. Master.
Shit slapped my nuts. I can’t hold off.

Breaker,
Sounds like your pussy is getting quite worked over eh faggot
Do you want to cum?

Chris
Yes sir
Please sir
I’m so wrecked too many hits. My balls are ready

Breaker
Beg for it like a total faggot. Then maybe I'll let you cum
Tell me who your pussy belongs to
And that you want to cum for me faggot
Say you’re a faggot too

Chris
You own my pussy Master.
I’m your faggot.
Please man I gotta cum so bad.

Breaker
Turn up the audio. I want to hear you pop it faggot like a good faggot

Chris
(Audio heard of him blowing his load)

Breaker
Ohhhh that's fucking it
You are my white faggot pussy boy

Chris
YES SIR…fuck it’s coming
I’m shooting
(sound of him gasping and wheezing now)

Breaker,
You came for me pussy.
My pussy faggot

(He is still breathing hard. I’m letting him come down slow by I talking him down)

Chris
Whew. Ah shit that was pretty intense shit
Still somewhat high too

Breaker,
So how was it being a fagged-out pussy?

Chris
Messy for sure. Head throbbing too

Breaker,
Sounded like you enjoyed it though

Chris
Yeah it was fun. I admit it
I hope you popped your wad too?

Breaker,
Oh I imagined doing it inside your pussy ass when you were moaning for me

Chris
Coming down. Fuck though
A nice thick fucking load
Shot long and hard

Breaker
Don't know what you were saying about not being a good sub. Go clean up and we’ll chat tomorrow. You got off big. Admit it

Chris
Yea. I fucking blew my nuts. It was hot.

*******

So what happened next? Did we chat the next day? Did he shyly ask to ‘try it again’? Do you want to hear what he sounded like blowing his load? Feedback, comments or whatever welcomed.
gelded_alpha@outlook.com