BondageDating

Choosing an Outfit for a Wig Challenge

A friend who knows I crossdress has challenged me. I need to take photos of myself while dressed up. If I do, she'll give me a wig. Since I don't have any…

member_a5483c4d42 2 Sept 2026 #1

A friend who knows I crossdress has challenged me. I need to take photos of myself while dressed up. If I do, she’ll give me a wig. Since I don’t have any right now, it seems like a good deal:mrgreen: However, there’s a catch: I have to look decent. It doesn’t matter if I appear more like a slut or more like a lady. The only issue is that I’m unsure what to wear to achieve this look. Usually, I just throw on whatever feels comfortable. Maybe you can help me choose some clothes for a nice outfit:wink: Here’s my current wardrobe:

  • Black bra
  • Red Bra
  • Black tank top
  • Black halter top
  • Black skirt
  • Black Fishnet stockings
  • Black tights
  • Back thong with white dots
  • Thong that is black and red with red edges and a heart in front
  • Knee-high patent leather boots, 6” heels
  • Over-the-knee boots, with 3” heels
  • Knee-high patent leather boots with straps, 4” heels
  • Black/White corset (lack = lack)
  • Opera gloves made of black material
  • Jeans skirt
  • Black pumps with 3” heels I hope someone can help because I really want that wig to complete my outfits:gag: And I’ll share the pictures if you’d like:wink::hi: