For soft girls, femboys, crossdressers, and feminine dreamers
Sissy On All Fours
Challenge Assignment
Your fifth file from the Classic Archive moves through dressing, positioning, preparation, edging, a post-climax ritual, and a final report.
01
First Direction
Dress the Part
- Pick out your favorite girly lingerie, something that makes you feel irresistibly feminine.
- Don’t forget a cute pair of panties!
- Lay everything out neatly, along with a pretty dildo you’re eager to feel deep inside your sissy hole.
02
Second Direction
Strip Down
- Remove all your boring boy clothes.
- Leave them behind, you won’t be needing them anytime soon.
Fig. 01
03
Third Direction
Feminize Yourself
- Slip into your lingerie, making sure everything fits perfectly and accentuates your sissy curves.
- Take a moment to admire yourself in the mirror.
- You’re transforming into the perfect little plaything.
Fig. 02
04
Fourth Direction
Assume the Position
- Get down on all fours like the obedient sissy you are.
- Imagine being taken from behind, this is how real men like their girls.
- Let the thought of surrender excite and arouse you.
05
Fifth Direction
Prepare the Toy
- Take the dildo into your mouth and suck on it like a good little slut.
- Get it as wet and slippery as possible with your spit.
- Show your dedication through every lick and suck.
06
Sixth Direction
Take It Like a Good Sissy
- Slide your panties slightly to the side and slowly insert the toy into your sissy hole.
- Feel yourself being filled as you push it deeper.
- Take your time, adjusting until it feels just right.
Fig. 03
07
Seventh Direction
Edge and Obey
- With the toy fully inside you, start stroking your sissy clit.
- Don’t rush, jerk off for at least 15 minutes before allowing yourself to cum.
- Stay focused on how naughty and submissive you feel.
08
Eighth Direction
Post-Climax Ritual
- After you cum in your panties, remove them and place them on your head as a symbol of submission and obedience.
- Savor the scent and warmth as a reminder of your true nature.
Fig. 04
09
Final Direction
Report Back
- Take a picture of yourself wearing your panties on your head and email it to Me.
- Include a detailed message about how you felt while completing this assignment.
Be a good sissy and complete your task NOW. I’m waiting to see how well you perform!! ✨
Good luck, darling! ✦
I love being in chastity. I pleasured a black man in an elevator and then in the stairway of a hotel me and my family were staying and never got his name.I crave it now.