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December 10, 2011
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(Contains: nudity, sexual themes and strong language)
Stranger: i'm male(age:20), seeking older dominant female

You: To do what hun?

Stranger: hmmm

Stranger: cyber?

You: What kind of cyber?

Stranger: cyber sex

You: I know that silly

You: but what type of sex do you like?

Stranger: im pretty submissive :P

You: Ever been forced feminized?

Stranger: also, im bisexual

Stranger: :)

Stranger: like

You: like...?

Stranger: I haven't

Stranger: but I fantasize about it

You: Ooooh, sweetie

You: you start, and we can see where this goes

Stranger: *how old are you?

You: 23

Stranger: *we are old friends who happen to meet up in the back of a big and quiet library

Stranger: *what should I call you?

Stranger: *im jack

You: *Christine

Stranger: oh hey Christine!

Stranger: you look great!

You: *Describe yourself Jack, I wanna see who I am talking to

Stranger: *im tall, pale, I have brown hair and blue eyes

Stranger: *I have a generally fit physique and I am currently shaking a a little bit and nervous since I find you very attractive

You: Oh Jack! It has been ages! My you have... changed~

Stranger: *awkwardly oh... thanks Christine

Stranger: you look great!

Stranger: I mean, you always looked great

You: *Grabs you in a big embrace

You: thanks so much! you are looking good too! Youve filled into a cutey!

Stranger: *pulls hips back, to avoid rubbing boner against you

Stranger: oh thanks

Stranger: *quickly shoves relationship book back on shelf

You: *Looks down to see you pulling off, and eyes the book.

You: Been doing some... reading?

Stranger: *book is about meeting guys for guys

Stranger: oh, um

Stranger: I mean I

Stranger: I was just browsing

Stranger: you know

You: Just browsing? Maybe you would like to come see some of the books I have at my place...

You: *I brush my hair off my shoulders, and turn

You: wanna come along?

Stranger: *nods submissively

Stranger: yes, Christine

You: Oh Jack~ *Giggles, and takes hand, leading you out of the library

You: You can come in my car!

You: *I point to a pink volkswagen beetle

Stranger: oh nice, I took the bus here :P

Stranger: I guess you've made more money than I have :P

You: Well, Ive been doing a little things here and there, you know~

You: *I get in the drivers seat, and unlock your door

Stranger: *climbs in, nervously smiles at you

Stranger: *what are you wearing, what do you look like?

Stranger: *covers lap with hands

You: *smiling back, and start the car up, and start driving. Along the way, i put my hand on your thigh, and keep it there, stroking slightly as I go

Stranger: *breathes loudly and bites lip as you stroke my thigh

You: *I have long, blonde hair, and a tight body. nice, full lips, and cute face. I am wearing a pink minidress that is tight on me

You: I finally pull up and get out of the vehicle, I go to your door and open it.

You: *Grabbing your hand, I lead you to my house

You: This is where I live!

Stranger: *smiles

Stranger: very nice

You: We enter, and I lead you up to my room

You: *

Stranger: *follows

Stranger: *visibly nervous

You: *I show you my bookshelf before abruptly grab you by the shoulders, and push you to the bed

You: I saw what you were reading Jack~

Stranger: I...

You: *playfully

Stranger: ummmm

Stranger: I mean

Stranger: idk, I've been exploring what turns me on a lot lately

You: Oh Jack! You can be honest, I kinda think its kinky. Are you kinky enough to... wear these?

You: *I hold up pink panties, a thong, nontheless

Stranger: *starts breathing faster

Stranger: um, Christine

Stranger: do you like to be dominant?

You: I like to be whatever I am in the mood for. So put them on.

Stranger: yes, ma'am

You: *More demanding, and dominant

Stranger: *starts to walk with panties into bathroom to change

You: Right here Jack.

You: No bathroom for you.

Stranger: yes, mistress

You: I like that. Mistress

Stranger: can I be slave?

Stranger: please, mistress?

Stranger: *looks surprised at own submissiveness

Stranger: I mean

You: Okay

You: Jocelyn.

You: *Laughs at your new name

Stranger: *bites lip as face reddens

Stranger: *takes off shirt

Stranger: *my little nipples are clearly hard

Stranger: *takes off pants, and my hardon stretches my boxers

You: *Smiles at that. they will amuse me later

Stranger: *awkwardly takes off boxers over throbbing hardon

You: *I walk over, and touch it

You: Since your doing some for me. Maybe little Jocelyn's clitty can have some fun

Stranger: *looks at you subserviently

Stranger: yes mistress

You: *I rub it a bit, but then walk away, and motion you to continue with the panties

Stranger: oh mistress, thank you for playing with my clitty

Stranger: *pulls panties stretched thin over my cock

Stranger: am I a good girl?

You: Maybe after this.

You: *I hold up the matching pink bra, with black lace on it

You: You know what to do sissy Jocelyn

Stranger: oh mommy

Stranger: *stops

Stranger: *looks embarrassed at calling you mommy

You: Mommy? I am mistress to you Jocelyn!

You: *throws bra at you

You: Now do it.

Stranger: *straps bra over my swollen nipples

Stranger: *shakes hips

Stranger: am I a good girl, mommy?

Stranger: *stops again

Stranger: *covers mouth

You: That DD bra looks great on you JOCELYN!

You: Bend over girl. Its time for a sissy punishment

Stranger: *please let me call you mommy ;)

You: *Only if you let this punishment happen

Stranger: *bends over and arches back like a little slut

Stranger: oh mommy, I want to look so sexy

You: *A firm slap on the bottom turns it red instantly.

You: Stand over there while I find you some suitable slutty clothes

Stranger: *nods and stands obediently

You: *I walk to the closet, and after a small while, come back with a bag

You: *I open the bag, and bring out a corset, black leather lined with a red, feathery substance

Stranger: oh, mommy I want to play with my clitty

You: Little Jocelyn will need to put on this corset first! Once you have your perfect sissy curves, you may finish off your clitty for a while

Stranger: *happily straps on corset and looks at self in the mirror

Stranger: oh, am I a sexy little slut?

You: *I walk behind you, and pull the bindings tight, restricting your breath a bit, but giving you beautiful curves

You: Yes Jocelyn. Now play with your clitty, and get ready for the rest

Stranger: *pulls head of cock out of thong and rubs it like a clit

Stranger: oh, oh .....

Stranger: I want all the boys to get big hardons when they see my slutty body

You: And they will Jocelyn... they will

You: *Heads over to bag, and reaches in. I peak back at you to see what your up to

Stranger: *pulls hand away from clitty when you look

Stranger: oh mommy, I wish I had tits as big as yours

You: They will be in due time Jocelyn. My little slut. They will be

You: *I pull out a tight, slutty black dress, and throw it to you. It is strapless

Stranger: *looks very happy

You: Put it on

Stranger: yes mommy

Stranger: *pulls dress over bra and corset

Stranger: *it tightly hugs my curves, but my cock is still tenting out

You: You need to fill those out!

Stranger: oh mommy I want big tits

Stranger: *looks sad

You: *I walk over and push on your unfilled bra. I then walk back to the bag, and pull out big, skin colored silicone tits

You: *Coming back to you, I put them in the bra, giving you big DD's

You: I then take out a toner, and blend it in with your spin, giving you realistic breasts

You: *

Stranger: *I look at myself in teh mirror

Stranger: *starts rubbing clitty

You: You will have to use these until I can get you real ones

Stranger: im a fucking sexy little slut

Stranger: oh, I wish I had real ones, mommy

You: You will soon Jocelyn. Now finish your clitty so it cant be seen under your dress.

Stranger: *pulls thong tight, pulling my thick clitty against my stomach

Stranger: *wiggles ass, which is just exposed under the dress

Stranger: am I your sexy little girl, mommy?

You: *I walk back to the bag, and pull out two rolled up balls. Turning to you, I throw them out, to reveal fishnet stockings

You: My sexy little girl should have fun in these

Stranger: *I pull them up my legs thighs

You: Good girl. You are my special little slut.

Stranger: legs, & thighs*

Stranger: *wiggles butt with excitement

Stranger: oh mommy all the boys will want to shove their cocks between my big tits

You: And more Jocelyn!

Stranger: oh Mommy, you're making Jocelyn such a little slut

You: *I walk to the bag again, and pull out something platinum blond

You: You need a fitting wig!

You: I throw it to you

You: *

Stranger: *I bend over obediently and pick it up off the ground

Stranger: yes, mommy

You: *it had a huge bump up poof in the back, giving it a 60's retro look

You: Pull your brown hair up, and put that wig on you little slut

Stranger: *nods

Stranger: *works hard to hide hair under wig

You: *I push forward, putting my hand against your stomach, on your still hard cock

You: Lets play with clitty more

Stranger: oh mommy!!

You: *I rub up and down as you finish your wig

Stranger: *twists legs tightly

You: More later Jocelyn, more work to be done first

You: *I walk away, to the bag again

Stranger: *looks after you longingly

Stranger: yes mommy

You: *I pull out a pair of thigh high slutty hooker boots, with a 6 inch heel

You: I expect you to walk in these like a pro at the end of the night

You: *I hand the slutty boots to you

Stranger: *awkwardly slips into the boots

Stranger: *the boots nearly reach my ass, which is mostly visible under the dress

You: You little slut~ *Sings out

Stranger: *the silicone implants stretch the dress so that massive cleavage is visible

Stranger: *trips and falls, pulling dress above my ass

Stranger: *I stand up and try to pull it down again

You: *I walk over, and give you a firm slap on the butt

You: You will learn fast Sissy!

Stranger: oh mommy, please teach your little sissy slut

You: We must finish you up first before I take you out!

Stranger: *nods

You: *I walk back to the bag, only to pull out a smaller bag. I carry it over to you

You: *Pulling out a small case, many false eyelashes are revealed

You: For your first night out, two sets of lashes on each eye!

Stranger: *looks up very innocently

Stranger: yes mommy

You: *I proceed to glue two sets of long false eyelashes to your eyelids. your lashes are far extending, and may be slightly heavy

Stranger: *bats eyes in mirror and leads finger down cleavage

Stranger: mommy, is there a daddy?

You: There will be a daddy soon, you shall see my slut

Stranger: :)

You: *I dig in the bag, and pull out a stick of chapstick

You: This is special chapstick. I will rup it around the outside of your lips, and it will make them bigger, and plumper, like temporary colegen. It will burn for a few minutes, but you will love it

Stranger: oh mommy :)

Stranger: can you rub it on my chest :(

Stranger: I want to be able to touch my nipples

You: *I then start immediately into rubbing it along the rim of your lips, shutting you up in the process. I move the breastforms away from your chest slightly, and rub it all over your bare chest.

Stranger: *winces with pain

You: Your boobs will grow slightly, and it will burn. But it is a step

You: *The breastforms over the swollen chest only get bigger, and tighten the dress more

Stranger: *begins to accommodate walking in high heels by sticking butt out and pressing chest forward

Stranger: oh mommy look at my fucking tits

Stranger: will they get smaller, or will I stay a little slut?

You: I know men would wanna fuck the heck out of you! Now come back, so I can finish your makeup, and finish your look

You: And they will get smaller, but we will have a permanent fix for it soon

Stranger: yes, mommy

You: *I take out pure black eyeliner and eyeshadow and apply it expertly

You: *I then use mascera to make your lashes even longer

You: *I apply rouge and toner to your face to get rid of blemishes

You: *And finish off with a slutty red shade of lipstick, over your lips, and the extended part of your lips from the chapstick

Stranger: *looks at self excitedly in the mirror

Stranger: *pushes tits together

You: Now, to finish you off, a little lipgloss to make you perfect

You: *I apply the last touch before letting you admire yourself more, and I admire you too

Stranger: *you can tell that I stop and feel ashamed and don't respond for several seconds

You: You are such a little slut Jocelyn. it is perfectly fine!

You: You can say goodbye to Jack!

Stranger: *looks back pleadingly

You: He is gone now!

You: it is just you and me!

Stranger: yes, mommy

You: Do you know how I make so much money?

Stranger: no, mommy

You: I am a female pimp my slutty Jocelyn. I make sissies like you, and find the right costumers. Are you ready for your first night? I will walk you through it?

Stranger: *cock throbs against dress

Stranger: oh mommy

You: But first, some practice. Walk that girly ass into my closet after I call you in.

Stranger: will they really want to fuck my tits?

You: *I step into the closet, and for a second, there is a pause.

You: Come on in Jocelyn, and yes they will love your tits

You: *I am turned so you cant see me when you come in

Stranger: oh mommmmy

Stranger: make me a slutty cockwhore

You: Come on in!

Stranger: *walks in, naturally shaking hips from side to side

You: *I turn, a giant black dildo now strapped to my waist.

You: On your knees bitch

You: and Suck

Stranger: oh mommmmy

Stranger: *gets to knees

You: Lick it slowly. Start by cuddling the balls

Stranger: *face flushes deep red and my cock throbs against the dress

You: And work your way up. I want some kisses, and licking before any real sucking

You: *I look and see your cock. and think "You will be relieved once your done your first cock"

Stranger: *cuddles balls in hand as I kiss the thick shaft

Stranger: oh mommy, your cock is so big

Stranger: *suckles on balls

You: Keep going slut

Stranger: sucks balls deep into mouth

Stranger: *looks up innocently

You: You better lupe this up real good, as its going to be used for later

You: *Looks back down and smiles, before nodding

Stranger: *strokes the shaft with both my hands

You: Now suck.

Stranger: oh mommmmy

Stranger: begins to suck the head of your thick cock

Stranger: *takes more and more into my throat

You: *I grab the back of your head, and start to slowly thrust

Stranger: *clearly attempting to relax throat to take the thick cock deeper inside

You: Mmmmm

Stranger: *garbled: I am such a lucky girl, other mommies don't play these fun games with their girls, do they!

You: * am starting to slowly get wet, horny from this experience

You: You will get this all the time with me Jocelyn. And no, you are a lucky Lucy!

You: Now finish off this cock, and turn around.

Stranger: *greedily worhips your cock, thrusting it deep into my throat as spit dribbles around my stretched lips

You: Soon my slut, that wont be spit!

Stranger: oh mommmy

You: And your lips dont seem to hurt enough. I may have to make them bigger with my chapstick!

Stranger: I neeed it

Stranger: *lips puff out painfully

You: *Smile as this happens

Stranger: Does Jocelyn have big cocksucking lips, now, Mommy?

You: Very big Jocelyn! I am sure any slut would be jeleous!

Stranger: I want them all to be jealous

You: And they will. Now stand up!

Stranger: *stands up

Stranger: oh mommy, I wish you would put your cock back in my throat

You: Turn and put your hands on the bed.

You: It is going somewhere else my sissy

Stranger: *turns and bends putting hands on bed. Dress naturally slides up revealing my entire plump little ass

Stranger: *arches back to expose my ass to you

Stranger: what will you do with your little girl, mommy?

You: I think you may already know Jocelyn.

Stranger: are you going to put your fat cock in my little sissy pussy?

You: * Slowly rub the tip of the cock around the edge of your butt. I then put it in slightly, just the head penitrating

You: *I wait for your reaction

Stranger: *moans

Stranger: oh

Stranger: *gasps, very horny

Stranger: do you like my tight boypussy?

You: I love this tight boypussy! Lets hope you lubed the cock up with your spit enough slut!

You: *Slowly pushes in more and more until the cock is in halfway

Stranger: oh mommy, fuck me with your big cock

You: *Waits for reaction

Stranger: oh fuck me, oh fuck me

You: *I toggle the back of it, and it starts to vibrate

Stranger: *moans like a whore

Stranger: oh yeah oh yeah

You: *I finally push it in all the way, and then come out.

You: *I stant to hump your ass with the cock

Stranger: *I push my ass back against you

You: Hows this my slutty little bitch?

You: *I slap the top of your ass, ramming you hard

Stranger: fuck your little bitch, mommy

You: *I then reach down, and grab your cock. I start to masturbate you hard as I hump your sissy ass

Stranger: oh mommmmmy

Stranger: my sissy clit

You: Your sissy clitty is tiny in comparison to this cock!

You: *Slap your ass with my free hand, even harder than before

Stranger: *moans

Stranger: mhmmm

Stranger: mmmm play with my little clitty

Stranger: oh fuck me

Stranger: *waggle ass after you spank

Stranger: fuck my fat little whore ass

You: *I keep going harder, and harder until I finish your cock off.

You: *EVen after your done, I leave the cock alone, but continue to fuck you

Stranger: *doesn't let himself cum

Stranger: mommy?

You: Im not done yet. You always wait till I am done!

Stranger: can you fuck me on my back so I can cum in my mouth?

You: * I oblige, and without much force, am able to turn you mid push. Your legs go over your head, and I fuck even harder, pushing into you with much force

You: GO FOR IT JOCELYN

Stranger: oh mommmmmy

Stranger: I want to drink cummmmm

You: Cum my slut! Cum all over yourself!

Stranger: *looks up innocently with cock pointed at face

You: Go.

Stranger: *cums on face

You: Lick it off!

You: *I suddenly pull out, and point at your face

You: Finish up. We have work to do.

Stranger: *begins to cry a littl as licks cum off face

You: *I unstrap the dildo, and turn it off, then I toss it to the side

Stranger: *are you a guy?

You: Eat me out my slut. I want to finish too!

Stranger: *nods

You: *I sit on the bed, and pull up my dress, ready for you

You: *No, I am legit a girl

Stranger: *vigorously licks your clit and pussy lips

You: Keep going slut

Stranger: *slides tongue through and along

Stranger: *begins to penetrate with tip of tongue while massaging clit with back of tongue

Stranger: *faster and faster

You: mmmmmm

You: *I moan

You: Its my turn... NOOOW

Stranger: *slowly pentrates with one finger

You: *I shout last part because of pleasure

Stranger: *slides two fingers deep as worships clit with tongue and lips

You: AAAAAAAAAAH!

You: *I am a screamer. I start to moan harder and harder

You: Jocelyn!!! dont... aaarg, stop!

Stranger: *sushes face into pussy as fingers speed up and arch up and back looking for gspot

Stranger: pushe*

Stranger: pushes*

You: AAHH!

You: AAAAAAAHH

You: *Pussy is so wet, it is sloshing on your face

You: *I grab your shoulders and squeeze hard

You: AAAAAAH

Stranger: **penetrtes with tongue and fingers while rubbing around with nose

You: AAAAAAH!

You: *I finish moaning, and just breath hard, clearly done

Stranger: *looks up messy and frightened

You: Now stop Jocelyn. You are finished.

Stranger: are you ok?

You: You were wonderful. Thank you my little bitch slut.

Stranger: :)

Stranger: man, I am really submissive

You: Yes Jocelyn you are.

You: Now, let me retouch your makeup, and give you something else aswell.

Stranger: ?

You: *I come over, and whipe your face with a cloth, and then redo your makeup

You: Now, close your eyes, and hold out your hands.

Stranger: *does

You: *Some shuffling around, with your hands, and then something squeezing on the end of your fingers

You: Open them

Stranger: *looks

You: *Doing so, you will see long red nails now attached to your nails

You: *fingers

Stranger: :)

You: Now, you are officially a slut.

Stranger: *waggles butt

You: Now come Jocelyn. Time to work your first evening. You are ready. But first!

Stranger: ?

You: *I give you a black, small purse, and put some makeup in it. I also put a dildo, and the chapstick in

Stranger: :)

You: This is if you need any pleasuring when your on your own
I was on omegle, and some guy proposed an idea to me! I have read and saw many sissy art here, and thought I could join the fun!
:iconbaneff18:
Baneff18 Featured By Owner Jul 28, 2012  Hobbyist Writer
actually it's pretty interesting, almost wish i had of found a chat room like this.
Reply
:iconnko619:
nko619 Featured By Owner May 21, 2012
This is the most disguting thing i ever read
Reply
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