Man Lost bet had to wear dress goes back to hotel in underwear

I lost a bet with my girlfriend on holidays in Sydney when I was 21 so I had to wear one of her dresses the next day all day.My girlfriend was a bit shorter than I I'm put the dress on the next morning but it don't cover half my underwear when I was standing still when walking you could see all of my pink underwear we had to go to 3 shopping mall that day and to the grocery store she would make me grab all the stuff we need from the top shelf so when I reach up all my pink underwear are showing finish shopping drop it back to the hotel then we out for dinner in a restaurant on the 12 floor had to walk up all the stairs ever stair I walk up more & more of my pink underwear would be showing get to the floor the restaurant was on look down you could see all of my pink underwear and skin up to my belly button.Pull dress down a much as I could to try and cover my underwear before walking in to the restaurant but still had half showing walking through the the table I could see all the people looking at my underwear finish eating and are about to leave.i said to my girlfriend are we just going back to the hotel she goes yes why and I said good and take the dress off left it on the table in the restaurant and walk out in just my pink underwear and get on the train back to the hotel in just my pink underwear.

Jul 24

Next Confession

Boy robbed of clothes

Related Posts

See today's best, hand picked, Amazon deals - Updated daily


  • newest
  • most popular
  • oldest
  • I tried investing in Cryptocurrency Via a trading Platform, I studied the platform and invested some money in it and I was advised to deposit more to be able to receive some additional profits, The honest truth is that I would never do cryptocurrency, but due to how it profitable and lost if stuff I thought I could earn from it as well, I deposited all I had and it all turned from something exciting to something Heartbreaking I was denied access to my money, I couldn’t withdraw they took everything I had just in a blink of an eye,I then later Found out it possible to get what you lost via crypto and in assets too back. I then search on how i could take the step of getting what they took from me back and then I found Quest Finance, they are an Elite Funds recovery company and they got me out of the mess I was in, not just by recovering my money but they also recovered my assets. This is a Fund Recovery and Legal you can talk to them ease the pain you feeling and get everything you lost back. There is a way to get all what you lost back just talk to Quest Finance For Help and Guidance. Visit their web or Email on
    Jeffsilbert 39 gmail com

  • Sounds like a crossdressing fantasy

  • I walk through town in my underwear 1 night I went out for dinner with girlfriend but when we get up to leave she ripped her pants I said will go to the toilet and I'll gave you my pants because you could see her g string and I don't want everyone to see that.So we go to the toilet she puts my pants on and we leave me in a shirt and red underwear and walk home.

Account Login
Is this post inapropriate?
Reason for reporting this post
Report this comment
Reason for reporting this comment
Delete this post?