Breaking in New Outfits (19/M)

[Overflow]

Hello everyone. I recently ordered and received two crossdressing outfits. I've tried them on for a few minutes but I haven't worn them for any extended period of time. I'm curious on any ideas that you all have for allowing me to break them in. I would be open to hidden public tasks but bear in mind that it is a bit cold where I live. I live with others but I often have the house to myself for extended periods of time so it shouldn't be too big of a problem.

I have a list of likes/limits in my signature and a link to the outfits themselves and my toys as well. I'm interested to see what you guys can come up with!

[Zeobit]

Regular training is necessary to accustom you to your sissyness, so you'll do a 7 day training program. Change between your outfits every day.

Day 1: Wear the outfit for 15 minutes while standing at the window.
Day 2: Be outside with the outfit for 15 minutes. can be hidden under other vlothing
Day 3: Be outside with either the top or the bottom part of the outfit visible, use online chats like omegle until 2 people have seen you.
Day 4: Sleep in your outfit, show yourself to 2 people online.
Day 5: Over the course of the day be outside with your outfit fully visible for 30 minutes. Must not be done all at once
Day 6: Sleep in your outfit, show yourself to 3 strangers on the internet and 2 people on the street (make sure they actually see you).
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals one person you must show yourself to either online or live.

[Overflow]

Originally Posted by Zeobit

Regular training is necessary to accustom you to your sissyness, so you'll do a 7 day training program. Change between your outfits every day.

Day 1: Wear the outfit for 15 minutes while standing at the window.
Day 2: Be outside with the outfit for 15 minutes. can be hidden under other vlothing
Day 3: Be outside with either the top or the bottom part of the outfit visible, use online chats like omegle until 2 people have seen you.
Day 4: Sleep in your outfit, show yourself to 2 people online.
Day 5: Over the course of the day be outside with your outfit fully visible for 30 minutes. Must not be done all at once
Day 6: Sleep in your outfit, show yourself to 3 strangers on the internet and 2 people on the street (make sure they actually see you).
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals one person you must show yourself to either online or live.

I really enjoy the idea of a week long schedule and I appreciate the effort. However, I'm not really into showing my face, especially to strangers on the internet.

[Zeobit]

Originally Posted by Overflow

I really enjoy the idea of a week long schedule and I appreciate the effort. However, I'm not really into showing my face, especially to strangers on the internet.

Oh, what a pity... In that case

Day 1: Wear the outfit for 15 minutes while admiring yourself in a mirror
Day 2: Wear the outfit, watch 15 minutes of porn where somebody wears the same clothes.
Day 3: Wear it for an hour, edge once after 30 minutes.
Day 4: Sleep in your outfit, masturbate after waking up, no cumming!
Day 5: Take pictures of you wearing that outfit in 4 different sexy poses. Admire yourself every time before you go to sleep.
Day 6: Sleep in your outfit, edge 3 times while wearing it.
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals either one more sexy pic or one more edge.

[Overflow]

Originally Posted by Zeobit

Oh, what a pity... In that case

Day 1: Wear the outfit for 15 minutes while admiring yourself in a mirror
Day 2: Wear the outfit, watch 15 minutes of porn where somebody wears the same clothes.
Day 3: Wear it for an hour, edge once after 30 minutes.
Day 4: Sleep in your outfit, masturbate after waking up, no cumming!
Day 5: Take pictures of you wearing that outfit in 4 different sexy poses. Admire yourself every time before you go to sleep.
Day 6: Sleep in your outfit, edge 3 times while wearing it.
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals either one more sexy pic or one more edge.

Thank you, I'll start today and report back here after each day.

[Overflow]

Originally Posted by Zeobit

Oh, what a pity... In that case

Day 1: Wear the outfit for 15 minutes while admiring yourself in a mirror
Day 2: Wear the outfit, watch 15 minutes of porn where somebody wears the same clothes.
Day 3: Wear it for an hour, edge once after 30 minutes.
Day 4: Sleep in your outfit, masturbate after waking up, no cumming!
Day 5: Take pictures of you wearing that outfit in 4 different sexy poses. Admire yourself every time before you go to sleep.
Day 6: Sleep in your outfit, edge 3 times while wearing it.
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals either one more sexy pic or one more edge.

I completed Day 1 today. It was fairly straight forward but it was nice being able to observe how nice the dress hugged my body. It fits quite well and it really does make me feel quite feminized.

[Overflow]

Originally Posted by Zeobit

Oh, what a pity... In that case

Day 1: Wear the outfit for 15 minutes while admiring yourself in a mirror
Day 2: Wear the outfit, watch 15 minutes of porn where somebody wears the same clothes.
Day 3: Wear it for an hour, edge once after 30 minutes.
Day 4: Sleep in your outfit, masturbate after waking up, no cumming!
Day 5: Take pictures of you wearing that outfit in 4 different sexy poses. Admire yourself every time before you go to sleep.
Day 6: Sleep in your outfit, edge 3 times while wearing it.
Day 7: If possible wear it for 24 hours, whatver you do. Every hour you fail to do that equals either one more sexy pic or one more edge.

I completed the second day just now. It was a bit difficult finding someone with the same clothes but I think I got it close enough. It was quite strange watching the video, knowing that they were donned in a similar outfit as I was. Regardless, it was quite enjoyable...