The Classic Archive Collection I · File 019/071

Classic Sissy Assignment Series

Assignment 19 The Big
Black Toy

I hope you kept your big black toy under the bed, still in its package, just as you were told. Make sure you have lube ready.

Sequence 19 of 71
Format Two-Toy Progression
Status Ready to Begin
Original Assignment · No. 019
Classic Sissy Assignment 19 — The Big Black Toy

For soft girls, femboys, crossdressers, and feminine dreamers

Big Black Toy
Assignment

I hope all of you good sissy sluts kept your big black cock toy under the bed, still in its package, just as you were told. The wait is over—prepare both toys and make sure you have lube ready.

01
First Direction

Dress and Apply Lipstick

  • Undress, shower, and put on some pretty panties with a frilly lingerie top.
  • Apply dark red lipstick to those sissy lips like your Mistress has taught you to do.
02
Second Direction

Set the Mood

  • Go into your bedroom and put on mood music—something that turns you on.
  • Move to the music in front of the mirror and see how pretty My little sissy whore looks in her lingerie and panties.
03
Third Direction

Unpack the Big Toy

  • As you move around, get both black toys that I previously instructed you to buy.
  • Take the big toy and rip it out of its package.
  • You have been drooling for a taste of this monster, and now is your chance.
04
Fourth Direction

Prepare the Smaller Toy

  • Lubricate the smaller of the two toys.
  • Lay it aside on the bed, ready to be used.
05
Fifth Direction

Tease with the Big Toy

  • As you dance and watch yourself in the mirror, rub the big black cock on your cheeks, kissing and licking it.
  • Rub it down over your body, against your sissy clit and ass.
06
Sixth Direction

Lubricate and Undress

  • Generously lubricate your big toy and put it on the bed beside the other toy.
  • Push your panties down to your knees and get ready for some fun.
07
Seventh Direction

Take Your Position

  • Get on your knees as if you have just offered your ass to two black cocks and you are aching to get pounded.
Fig. 01
Positioning reference for the two-toy progression
Progression reference · Take the starting position
08
Eighth Direction

Start with the Smaller Toy

  • Take the regular-sized dildo and begin to tease your man cunt before sliding it inside.
  • You can feel your sissy nub tingling and getting hard, but you aren’t allowed to touch it.
09
Ninth Direction

Stretch and Trade Up

  • Fuck your sissy ass with that toy while staring at the monster waiting for his turn.
  • Tell him how badly you want him in your hole.
  • Stretch that ass out well and deep, then trade that dildo for the big one.
10
Tenth Direction

Take the Big Toy

  • He is hard and ready to pump your ass.
  • Push him inside and say how much pleasure and pain you are feeling.
  • Beg for more and take that monster black cock as far as you can.
Fig. 02
Large-toy progression reference
Progression reference · Move to the larger toy
11
Eleventh Direction

Finish in Your Hand

  • Once you have had all of that big-cock ass-fucking you can take, remove it from your man cunt.
  • Pump your sissy nub until you squirt your cum into your hand.
12
Final Direction

Clean Up Every Drop

  • Show your Mistress what a hungry cum slut you are by licking all that sperm off your hand.
  • Swallow every drop.

Be sure to take photos or video and send them to Mistress. She loves to see her sissy whores in naughty action! ✨

File 019 · Photos or Video Required
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Your twentieth assignment is waiting.

Continue the archive one file at a time and carry your practiced progression into the next classic assignment.

Open Assignment 20
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Dave
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Dave
5 months ago

This one, this one affected me hard. I can’t stop thinking about cock It’s like 24/7

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