Embarrasng crossdressing tasks 18M

[Juanmessy]

Recently i have been exploring other aspects which i habe never adventured into before. Previously i have done hidden public leading to public. This week i am wanting to try out embarrasing crossdressing tasks which i will be completing and providing reports on here qhen done. Hopefully i can keep this thread active and get a great selection of tasks to complete

[CSasha]

For starters, go to a park or into the woods. If you are in danger of getting lost in the dark, take a bright light with you. Change to your
crossdress there, and walk there crossdressed for 30 minutes. Since you are a beginner, you may even leave the trail to avoid strangers. Exposed enough for a good beginning, I think.

Report here when you did this, please.

[Juanmessy]

Originally Posted by Cassandra

For starters, go to a park or into the woods. If you are in danger of getting lost in the dark, take a bright light with you. Change to your
crossdress there, and walk there crossdressed for 30 minutes. Since you are a beginner, you may even leave the trail to avoid strangers. Exposed enough for a good beginning, I think.

Report here when you did this, please.

Last night I went out to the local woodlands with my light and a change of crossdressing clothes. I took a pair of leggings, dark blue tshirt, a hoodie and a small denim coat with a pair of running trainers. When I arrived I stripped down and replaced all my clothes with the crossdressing clothes I bring and out my normal clothes in my bag

I started off by walking along the main path as it was about 9pm so it wasn't too early but later on I decieed to walk off the path just incase. Throughout the whole walk, my heart was racing and I was excited to finish this task as I really didn't want to get seen by anyone. About 20 minutes in I decided to turn back and walk back toward sthr entrance where I had the most chance off getting caught but I stayed just off to the side of the trail which made it less likelym

When I got back to the start I found a tree which I stripped back down then changed into my normal clothes. I appriciate you given me an easy option as I was a beginner which made me feel more comfortable doing

[CSasha]

Very well done. Yes, I offered a small step. It's important to start little, continue, slowly increase.

I understand your report that way that the leggins etc. were the normal cloth. Right? If yes, what were your crossdressing cloth?

[SasssySlavePuppy]

Woof woof

I think you need to go shopping, so stroll through the women’s section and pick out an outfit. Grab a bikini too, so maybe make it a beach outfit.

Then, go to the dressing room and try on the clothes. When you are dressed, accidentally unlatch the door and let it swing open. You should twirl and look at yourself in the mirror for 3 minutes with the door open slightly. Hope no one sees!

Woof your horny puppy woof

[Juanmessy]

Originally Posted by SasssySlavePuppy

Woof woof

I think you need to go shopping, so stroll through the women’s section and pick out an outfit. Grab a bikini too, so maybe make it a beach outfit.

Then, go to the dressing room and try on the clothes. When you are dressed, accidentally unlatch the door and let it swing open. You should twirl and look at yourself in the mirror for 3 minutes with the door open slightly. Hope no one sees!

Woof your horny puppy woof

Thank you, this will be hard but looking forward to doing so

[Juanmessy]

Originally Posted by Cassandra

Very well done. Yes, I offered a small step. It's important to start little, continue, slowly increase.

I understand your report that way that the leggins etc. were the normal cloth. Right? If yes, what were your crossdressing cloth?

The leggings were crossdressed. The clothes I listed was all female clothes which i changed into, didn't make the clothes too obvious

[CSasha]

Ah, alright. That was my second guess. Just wanted to make sure how daring your crossdress actually is, to adapt the dare.

I dare you to look for a nice, re-recognizable place in the woods probably nobody drops by by accident. Go there in your male cloth, change into your female cloth (sounds like female athletic clothing). Take everything of value with you, only leave your male cloth. If weather requires, bring a bag to put your male cloth into. Hide that bag if you want.

Then go for a little. Doesn't need to be fast. Actually slower is better. Make it a very long walking distance. Every half of a mile, stop for at least 2 minutes of stretching exercises. Try to imitate how girls and women do these. And don't forget to smile. That's most important.
The run should return you to your place in the woods with your male cloth in the end.
The path of your run is your choice. I suggest something less frequently used but still good for walking or running. Something in the nature probably.

[Juanmessy]

Originally Posted by SasssySlavePuppy

Woof woof

I think you need to go shopping, so stroll through the women’s section and pick out an outfit. Grab a bikini too, so maybe make it a beach outfit.

Then, go to the dressing room and try on the clothes. When you are dressed, accidentally unlatch the door and let it swing open. You should twirl and look at yourself in the mirror for 3 minutes with the door open slightly. Hope no one sees!

Woof your horny puppy woof

Let's start with this one, it turned out this wasn't too bad.

I went to the local clothes shop which I knew had many changing rooms. When i got there I went to the female clothes and tried to look for a bikini but they didn't have any as it is too early in the year for it. I ended up picking up bra, panties, a pair off short and a light blue tshirt.

When I got to the changing room I started slowly stripping down and put the panties on, then the bra followed by the t-shirt and the shorts. As I was putting the shorts on I accidentally leant on the latch and the door flew open, I stood there looking in the mirror posing and check-in my outfit out. Thankfully I got one of the changing rooms toward the end of the hall so the chancrs of getting seen was very low but there was still a risk of getting seen.

When the time ended, I had to step out of the changing room to grab the door which at that time someone was just entering their room and one was just leaving so if timing wasn't on my side I would have been seen. I closed the door quickly and got dressed then put the clothes back to where I got them from and walked out the shop

[Juanmessy]

Originally Posted by Cassandra

Ah, alright. That was my second guess. Just wanted to make sure how daring your crossdress actually is, to adapt the dare.

I dare you to look for a nice, re-recognizable place in the woods probably nobody drops by by accident. Go there in your male cloth, change into your female cloth (sounds like female athletic clothing). Take everything of value with you, only leave your male cloth. If weather requires, bring a bag to put your male cloth into. Hide that bag if you want.

Then go for a little. Doesn't need to be fast. Actually slower is better. Make it a very long walking distance. Every half of a mile, stop for at least 2 minutes of stretching exercises. Try to imitate how girls and women do these. And don't forget to smile. That's most important.
The run should return you to your place in the woods with your male cloth in the end.
The path of your run is your choice. I suggest something less frequently used but still good for walking or running. Something in the nature probably.

I found a larger woods that isn't too far away from my house which is very useful for me to do stuff. I walked around the wood for a bit to familiarise myself with the wood as I never knew about it. Once I found a place which I thought would work, I stripped and changed to my female outfit and put my male clothes say in my bag. I hid my bag in a large bush and then walked away.

I started with a casual strool around the area near by exploring the brand new area to me which was very exciting thinking about all the possibilities that could work. When I reached the first half mile mark I done a few lunges to keep my legs going then I continued to walk. The walk continued for about 40 minutes before I managed to return to my bag. I went behind the bush and found my bag with my clothes in then i got dressed and exited the wood the way I left.

[CSasha]

Very good! Many thanks for the report.

Are there many people walking in that forest?

[Juanmessy]

Not too sure as it is the first time I have been there. I'm assuming it's a common dog walking spot