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Underwear walk dare number 2...

Posted 06-04-2022 at 02:32 PM by Matt:
Updated 06-04-2022 at 02:42 PM by Matt:
Tags dare, report

Not sure anyone is really interested in this, perhaps not your usual type of dare here, but I have been told to post it, so I'm just following instructions lol

(Very similar to my previous dare, but it has been made harder/more difficult, as I made 1 or 2 mistakes the 1st time....)


The dare I was given - You must go for a walk on a sunny day following a proper public footpath. You must be wearing a bra with your breast pads in, tight fitting t-shirt, your red briefs and some trousers/shorts. At some point of the walk you must remove your trousers/shorts and put them in your bag. Then you must walk a minimum of 2 miles without any trousers/shorts on. A few conditions to add-:

You are not allowed to go off the proper path for any reason.

You are not allowed to try and cover yourself in any way.

You must not make any effort to avoid any people on the walk.

You are not allowed to slow down if you are catching walkers ahead, if you catch them up, you must go past them.

No running or extra fast walking. You must always walk at your normal speed.

If anyone talks to you, you must respond.

Once you have taken trousers/shorts off, that is it for a minimum 2 miles, no splitting distance up, they are off for at least 2 miles continuously.

I want more pics and gif's posted this time, at least one lifting your t-shirt to show your bra.


The last dare was done while I was on holiday at a place with a far smaller population than where I live, so I was more nervous this time, doing it near where I live. It was also a national holiday, meaning more people may be about.

We picked the walk between us, it was a walk just over 5 miles long, starting in a nature reserve, had some paths along canals, fields and disused railway line.

While I was getting dressed into the required clothing (red briefs, pink bra+inserts, tight blue t-shirt and grey trousers) I was thinking of where would be best to do the 2+ miles without my trousers.... I thought the nature reserve part would be the most busy, and the canals are popular with dog walkers, joggers and people fishing. So I decided that the best place to remove my trousers would be as I left the canal path and started across the fields. The disadvantage of this though, was that I would be visible from a further distance as the fields were very open, part would be along the disused railway line, which is popular with cyclists and it would require me to walk a short distance alongside a very busy road.....

Anyway, that's a long intro, I'll speed up the report now.

I felt a bit self conscious of my "bosom" during the first part of my walk, looked very noticeable to me, and was wondering if anyone noticed or thought it was strange as they walked by, but I think the thought of what was to come, made that seem like not such a big deal haha
I did pass quite a few people during the 1st part, a few said "morning" to me as we passed, but no other comments.

Once I turned off the canal path onto the fields part of the walk, I knew the moment had come, so after making sure nobody was in view, I took off my trousers and put them in my bag.

I thought this would be a good point to take some pics and video's.

I felt very nervous walking now, knowing if anybody was around, there would be nothing I could do to disguise my state of (un)dress... not even any trees to hide behind lol

I also remembered to take picture showing my bra....

Luckily, I didn't see anyone while crossing the fields, but I knew this would not last once I had got to the other side, as that would be the part where I had to walk a few yards alongside a busy road...

Before I got to the road, I had to walk a little along a track that led to some businesses. I noticed there were some CCTV cameras and prayed nobody would be looking at the monitors or recording later! It did take me a few minutes to work up the courage to go, which was a mistake, as soon as I got onto the track I saw a guy on the track not too far behind me, he saw me for sure, but I didn't hang around to see his reaction and walked up the track towards the road, only to see a car parked at the end, that I would have to walk right past! Thankfully, there was nobody in the car, and I walked onto the road, with many vehicles wizzing past as I walked alongside, I can only imagine what the drivers/passengers must have thought, they could hardly fail not to see my state! I wanted to run, but controlled myself and just walked (maybe slightly faster...)

(excuse the poor videoing but I didn't want to draw any more attention to myself!)

It was only after I was off the road, that I suddenly thought, a lot of cars have dashcams nowadays here, I hope none thought to save the video, I don't want to find myself on youtube!!!

Anyway, I continued my walk along a narrow path that led to the disused railway (and cycle track..)

Once on the disused railway, I knew there was little chance of there being nobody else around anymore. True enough, it wasn't long before I heard a bell behind me, as 2 cyclists came past,don't get much warning of bikes to prepare myself, not that there was anything I could do lol Just hope they forget what they saw quickly...

Fortunately, it wasn't too busy, about 3 more cyclists and a couple walking a dog were the only others that went past, and nobody asked any questions!

I was relieved when I got to the canal (about 2.3 miles since I got to the fields) and I could put my trousers back on for the last part of the walk back to my car.

I hope the dare was all done satisfactorily this time and I don't have to do it again!!

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  1. Old Comment
    Matt:'s Avatar
    Posted 06-04-2022 at 02:33 PM by Matt: Matt: is offline
  2. Old Comment
    I see London, I see France, I see Matt's underpants! xD

    At least you were allowed a shirt over those boobies :3

    And I bet you're really glad you were allowed to wear men's underwear!
    Posted 06-04-2022 at 05:49 PM by NoPantsKayla NoPantsKayla is online now

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