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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.
Back when Craigslist was a hookup site I invited a guy to my hotel room. He showed up with party favors galore. Once I was too high to resist, he had me stripped down to only a blindfold and a pair of neon lime green lace **, with my wrists bound together above my head and the end of the rope secured to the curtain rod. I thought I was standing in the middle of the room for only him to see, but he stood me in front of the huge window on the 2nd floor overlooking the busy hotel parking lot; being blindfolded I had no idea I was on full display. The idea was for me to stand there so he could finish on me, then leave. After about 30 minutes I jumped when from behind me he suddenly finished on my bare back. He immediately dressed, took my wedding ring and cash from my wallet before leaving, propping the hotel door wide open on his way out, leaving me very exposed and vulnerable where I was. A full 30 minutes later staff and security showed up and I was asked to leave immediately.
Teach you not to bet .
No I don't think so.
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.
Cool
My cousin's friend got locked out of her house wearing a short white t-shirt and green **. I'm outnumbered. So, we walk back to my cousin's. Her friend now wearing my clothes and me wearing her t-shirt and my tighty-whities. Longest four blocks of my life.