Sissy whores and prostitutes 15

Sissy whore forced to work the streets as one of my tranny hookers…

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Context: After a course of deep feminization it’s time you start earning your Mistress some cash. I kick you out of the car in a she-male red light area, where a plumber named Tim invites you into the back of his van.

Tim, the man who has just paid twenty bucks for a sissy whore, lifts up your PVC skirt and stares at your fishnet stocking tops. You’re on all fours in the back of a van and your thigh high boots gleam in the lantern light. Your little sissy clit starts to buzz.

Tim’s burly hands grab you by the waist and he starts probing your eager hole with his cock. It’s now as hard as an iron girder. You’ve completely forgotten about the condom because condom is a single word and right now there’s only two words going through your slut brain: two words you’ve always wanted to say to a man…

“Fuck me!”
“What was that?” he asks, still probing.
“Fuck me…I want it…please…fuck your sissy whore!”

He spits on his hand and rubs your hole, then he probes for a millisecond before slipping his giant cock all the way into your crack. You moan in pain and pleasure and shock…but it must be pleasure because no sooner has he reached the hilt than you wriggle, trying to get more friction.

“Stop fucking wriggling, you fucking whore!”
“Yes, sir,” you say.
“Sir, I like that,” Tim decides.
“Plesase… fuck me hard, sir… I’m a little whore…. I need it hard.”
“Fucking sissy whore!”

On the outside, the van is rocking and your moans are clearly audible as Tim the plumber pork-swords you. Turned on by your slutty enthusiasm he’s having a whale of a time and repeats his mantra every ten seconds or so: “Fucking whore!” to which you repeat yours: “Yes, sir… I’m a sissy whore…fuck me… I’m a filthy whore.”

Although you would never admit it to your Mistress, you prefer a real cock to my strap-on, don’t you? And you also like the way he holds your waist with a man’s strength.

You’re bucking as he pork-swords you, but his strong grip keeps his whore in place. After five minutes of rigorous pounding, you begin to feel an incredible sensation in your anus. It is starting to go numb…the way your gums go after cocaine. It is intensely pleasurable. You’re approaching prostrate orgasm….

But it’s not to be.

Tim the plumber suddenly withdraws and shoots a massive load all over the black vinyl skirt hitched around your waist, and all over your top. You turn round quickly to catch some of it in your cum craving mouth…but he’s already spent. Your little cock twitches, desperate for relief. You almost offer him the twenty bucks back if he’ll carry on fucking you.

“Fuckin hell…I’ll take you again, bitch,” says Tim. “Make sure you’re here next time I come to town. That was excellent.”
You say nothing.
“Right…off you trot, you little whore!”
“Yes, sir.!”

Two minutes later you emerge into the night, your back dripping with cum. This is the cum of a stranger you just sucked off and allowed to bugger you in a public carpark for twenty bucks.

You filthy, little sissy whore…

I think you’re going to be one of my best little earners!

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15 Comments

  • Andrea Tiffany says: April 24, 2018 at 4:26 am

    I can’t wait to earn money and cum

    Reply
  • Kylie says: April 24, 2018 at 8:55 am

    Living as a sissy prostitute would be a great way to maximize the amount of dicks I take up my ass each day, sign me up! I want to be covered in jizz and deepthroating strangers dicks until I pass out. Hopefully I can become an efficient earner.

    Reply
  • Lisa says: October 2, 2018 at 11:38 pm

    Dearest Mistress Elle,
    Being a sissy whore and prostitute for you would be the fantasy cumming true. Every time I slip into my lingerie, black leather mini skirt, leopard print top and makeup, I dream of looking as beautiful as the girls on your site, becoming a bimbo.

    I told Mistress Elle that I wanted to be feminized and she instructed me to dress up in my favorite feminine attire and send her a photo. I shaved my entire body and tucked my pathetic little clitty down into pink nylon panties. Put on my ash blond shoulder length wig. I pulled on my high waist padded panty and beige pantyhose, stepping into 4 inch black patent pumps and locking the ankle straps with little black pad locks.
    My favorite bra is a long line Bali, back hook size 42D which holds my latex breasts. My measurements are 47-36-50. My full slip is short, pink, nylon and covered in lace. I apply my makeup. Cover foundation,eye lashes, eye shadow, eye liner, blush, lip plumper and Revlon color riche lipstick in “Drumbeat Red” I spray on “Poison” perfume and pull on my nylon leopard print long sleeve top. I shimmy into my black leather mini skirt that has a side zipper and clasp. My skirt has two little zippered pockets that easily hold two condoms each, in case Mistress Elle wants me to use them.
    My purse contains my feminine items and a phone with which I am to send Mistress photos of the cocks I meet.
    I look at myself in the mirror and run my long finger nailed hands up and down my body quivering with delight. I go out the front door locking it behind me and walk down the street towards the night, hoping I will be good enough for Mistress Elle.

    Reply
  • Lisa says: November 16, 2018 at 9:59 pm

    Dearest Mistress Elle,
    As this sissy walks down the dark street she is quivering with delight at the thought of being your sissy whore.

    Reply
    • Elle Mesen says: November 19, 2018 at 7:39 am

      Errant Sissy…what a thrashing I will give you with my paddle!

      Your thoughts must not be focused on your own desire… a sissy slave is an object that only feels what its Mistress tells it to feel. In your case, as one of my future street whores, you must be solely focused on that 20 dollar bill you will receieve for each spurt of jism a customer shoots down your throat! You are there to make me money…not ‘quiver with desire’. Please confirm that you have understood this message and that you are ready for punishment!

      Reply
      • gabriella says: November 25, 2018 at 1:24 pm

        I will focus to have many clients in the street or a brothel, to earn money for Mistress !!!
        I am a slut and the best job for a slut is to be a whore !!!

        Reply
  • Pussyassbilly ChastitysissyWhore says: November 20, 2018 at 9:02 am

    $5 DOLLARS AND I WILL EARN 2X WHAT YOUR BEST BRINGS YOU

    Reply
  • Lisa says: November 30, 2018 at 8:12 pm

    Dearest Mistress Elle,
    This errant sissy begs your forgiveness and understands that she has only your desires to care about. You and only you. Sissy is ready for punishment and will focus her attention to your desires. Sissy will focus on the twenty dollar bills that she will earn for you with each spurt of jism that shoots down her throat.

    Reply
  • Lisa says: December 1, 2018 at 9:34 pm

    Dearest Mistress Elle,
    As this sissy walks down this darkened street in the sissy red light district where you have instructed her to go, she must remember to focus her attention on the money that she will make you as your street whore. Sissy must never forget that she owes you everything for her sissy life and must always remember that your desires, Mistress, must be fulfilled.

    Reply
  • Lisa says: December 1, 2018 at 11:14 pm

    Dearest Mistress Elle,
    As this sissy street whore walks down the dirty back ally, she will remember to focus her attention on the money that she is earning for you. She will never forget that she is your street whore and owes you everything for her sissy life.

    Reply
  • Lisa says: December 22, 2018 at 8:15 pm

    Dearest Mistress Elle,
    Thank you for dropping me off in the tranny red light district.

    Reply
  • Lisa says: December 30, 2018 at 2:52 am

    twenty dollar bill, twenty dollar bill, twenty dollar bill, twenty dollar bill,…….twenty dollar bill, twenty dollar bill…

    Reply
  • Lisa says: January 4, 2019 at 11:53 pm

    Dearest Mistress Elle,
    The only thing going through my sissy brain is saying out loud, “Fuck me!” “Fuck me… I want it…please… fuck your sissy whore!” and thinking about making money for you.

    Reply
  • Lisa says: February 2, 2019 at 7:21 am

    Dearest Mistress Elle,
    This errant sissy is grateful for the thrashing you gave her with your paddle and begs you to please put her back out on the street again to make you money.

    Reply
  • Lisa says: February 14, 2019 at 2:28 am

    💋💋💋💋💋💋💋💋💋💋

    Reply
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