• Hello my kinky friends!
    I am still so overwhelmed by the support and love we’ve seen in our ever-growing community over the past week.
    We are SO close to 1,000 users!
    Once we hit that milestone, we have some fun things planned — including prizes and activities — so stay tuned! Keep an eye on Kinky Quests for details.
    Please welcome our newly promoted staff!
    Due to our growing community, we’ve promoted an amazing group of staff members. Take a moment to welcome our new mods, curators, and greeters: Meet the KW Staff
    Interested in helping out as a greeter? Feel free to post here: Become a Greeter
    New Feature: The KW Calendar!
    Inkwarden has just introduced our new calendar, located in Kinky Quests . Our Curators will be busy adding events and quests, so keep an eye on it!
    Currently, only mods and curators can add events. If you’d like to suggest one, post here and staff will help you out: Quest & Event Suggestions
    As always, thank you for being part of this amazing community. If you’d like to contribute financially, donations are always appreciated: Support Kinky Wonderland
    Have a kinky week! 💜

Loser has to Crossdressing Edition

Reply to thread
Sort by newest Sort by date
Ponies

Ponies

Bedwetter
Silly Filly
Supporter
Joined
Jan 2, 2026
Location
Ponyville
Gender
TransFilly
Pride
Pastel Pride Pastel Pride
We all know how this works.

Player 1 joins with a dare
Player 2 plays against player 1
Player 3 decides the loser and starts a new round as player 1



Winner sends loser 3 photos. Loser builds an outfit based off the winner's photos and sends a pic dressed to the winner. If winner approves the outfit the loser must remain in it for the day. If winner does not approve the loser must try again and send a new pic. (If pics a limit use a detailed description.)

in
 
toaster lost

Winner sends loser 3 crossdressing dares with a part not disclosed. Loser picks two of them. then the winner discloses what the hidden part was. if loser does both dares then winner does the 3 one
 
Sissysistah loses.

Same dare:
Winner sends loser 3 safe or hidden public crossdressing dares with a part not disclosed. Loser picks two of them. then the winner discloses what the hidden part was. if loser does both dares then winner does the 3 one
 
Barme loses

Winner sends loser 3 crossdressing dares with a part not disclosed. Loser picks two of them. then the winner discloses what the hidden part was. if loser does both dares then winner does the 3 one
 
John's Explorations loses

Loser sends winner.

Budget
Store(s)
Size(s)
1-3 simple ideas they would be willing to do.

Winner uses this information to create an outfit and dare for loser.

In
 
Sorry Johns. I just flipped a coin and you lost :3 (tails). First time trying a loser-has-to game. Let's see how it goes. I'll do the same dare.
 
You must log in or register to reply here.
Back
Top