18 F- Wanting to Try New Things

[Mr.sissyboy]

Do this dare late at night when you’re the only one up. You’ll need a backpack, a padlock and a key for it. Leave the key in your room/house/yard. You take the backpack and walk as far away as you’re comfortable with. Take your clothes off and lock them into your backpack and walk home naked to get the key!

[Lushrant]

Originally Posted by RPwALover

As a dare, you will go out when it's dark (you can choose the location). But you are not allowed to strip outside. You have to strip inside, then leave the house naked. You are allowed to wear shoes if you prefer. You will do ten push ups, then masturbate ten minutes, then 9 push ups, then masturbate 9 minutes, then 8 push ups and 8 min masturbating...until you reach 1 push up and one minute. You are not allowed to cum.

I completed this dare late last night. I left my clothes inside, except for shoes, and went outside to start the challenge. I was very wet prior to this and the constant masturbation on and off did not help with that. I tried my best not to, but I did cum on the 7 minute mark. I felt myself getting close and tried to hold it. I should have stopped touching entirely but thought I’d be able to hold it longer. By the time I stopped touching it was too late. The orgasm was incredible but I do understand that I was not supposed to cum with this challenge. I am requesting a punishment since I did fail. I am willing to try any punishment as long as it does not involve photos or videos being sent to anybody. My afternoon class was canceled today so I have most of the day free to do any dares or punishments.

[Lushrant]

Originally Posted by Mr.sissyboy

Do this dare late at night when you’re the only one up. You’ll need a backpack, a padlock and a key for it. Leave the key in your room/house/yard. You take the backpack and walk as far away as you’re comfortable with. Take your clothes off and lock them into your backpack and walk home naked to get the key!

I have completed this dare last night. Honestly, I am starting to get used to walking around naked outside and don’t feel as nervous anymore doing it. I left the key in my bedroom and walked to the park, down the street. I stayed there for a few minutes, then went back. The part that was more risky and nerve racking was walking back into my house and to my room, as sometimes my parents will wake up at night. I really enjoyed this dare and would love to try similar ones.

[grannyd16]

Why don't you try this, during the day (can be during the night but I thought id bump it up since you are getting used to it) go to the park and find a tree with branches low enough to reach. Then take a piece of clothing off and hang it from the tree, then continue to do so on different trees for each article of clothing. Once you are done, you need to do a lep of the park edging before you can get your clothes back

[Akitawa]

Wear your smallest swimsuit and nothing else. If it's not too painful, use cloth pin to your nipples. Now let's test how courageous you are. You need to edge three times from humping with your sister pillow. You can't move the pillow outside of her room.

After that, while keeping your position and play your video. Put your face to the pillow and raise your ass. If you smell it funny, you can only clean it by sucking. Play with your clit to keep your hand busy. If you don't clean it clean, maybe your sister will be able to smell it and notice how pervert her sister is.

For the entire day, you need to keep wearing your swimsuit underneath. You can only cum at night before sleep while writing your report.

[RPwALover]

Originally Posted by Lushrant

I completed this dare late last night. I left my clothes inside, except for shoes, and went outside to start the challenge. I was very wet prior to this and the constant masturbation on and off did not help with that. I tried my best not to, but I did cum on the 7 minute mark. I felt myself getting close and tried to hold it. I should have stopped touching entirely but thought I’d be able to hold it longer. By the time I stopped touching it was too late. The orgasm was incredible but I do understand that I was not supposed to cum with this challenge. I am requesting a punishment since I did fail. I am willing to try any punishment as long as it does not involve photos or videos being sent to anybody. My afternoon class was canceled today so I have most of the day free to do any dares or punishments.

First, did you cum before having done any of the pushups?
Second, I wrote you're not allowed to cum only because I thought you'd been doing the task sooner when you were still denied.
__________________

[zephyrnem]

What is your favorite part about being naked outside?

So...pick five places outside (at least 50 m apart...or 3 to 4 minutes walking time) Do this before you start the dare. You want places where you can stop...or maybe even sit. Up to you.

Wear four pieces of clothes (shoes can count as 1 for the pair).

Leave your house at night. At each station...take off a piece of clothing AND then stay there for 3 minutes before moving onto the next station. At station five you will sit there for 3 minutes naked AND THEN you must stay there until you cum.

Now...you can either stop at each station again for 3 minutes and when the time is up NOW put on a piece of clothing at a time at each...OR...you can gather your clothes in a bag and NOT put them on and walk home naked without a time penalty at each station. Up to you.

If you do not follow the rules you will be punished and the punishment may involve making you be caught naked (hahahahaha) or not. As always...you are in charge and are having fun. Enjoy!

(Though I wish I was here to watch and make SURE you went through with the dares!)

[Lushrant]

Originally Posted by grannyd16

Why don't you try this, during the day (can be during the night but I thought id bump it up since you are getting used to it) go to the park and find a tree with branches low enough to reach. Then take a piece of clothing off and hang it from the tree, then continue to do so on different trees for each article of clothing. Once you are done, you need to do a lep of the park edging before you can get your clothes back

I completed this yesterday. I did it on a walking trail near my home that is normally very dead during the day. The park itself would have been too risky. I made sure the trees were pretty far spread apart and left one time on each one, until I was naked. Once I was naked, I ran up and down the trail before collecting my clothes. Being naked outside during the day was such a thrill and I definitely enjoying this dare.

Originally Posted by RPwALover

First, did you cum before having done any of the pushups?
Second, I wrote you're not allowed to cum only because I thought you'd been doing the task sooner when you were still denied.
__________________

I came about one third of the way into the dare, so I had done push-ups at that point. I did still continue it and finish the dare.

Originally Posted by zephyrnem

What is your favorite part about being naked outside?

First of all, I love the feeling of it. Being naked is just overall more comfortable. Also the thrill of potentially being seen is a big turn on. This may sound weird but the time my sister caught me masturbating was a big turn on to me.

I will be completing your dare, as well as others on here, as soon as I can and update with a detailed report. Thank you for the dares and keep them coming.

[Ray_Q]

Wow, its amazing how bold you've become in such. Short space of time, back on page three being naked outside was an achievement in itself, now look at you. Its great fun to read about your adventures.

Do you think you can find a place outside where you can't easily be seen, but you can see other people? I'm thinking maybe in some bushes by the edge of the park or by the side of the road. Such a place would be ideal for a masturbation session, especially if you can put some distance between you and your clothes. Add spice with baby oil and something to put up your butt. Update the thread as you're doing so for extra kudos.

Well done and be safe

R

[Lushrant]

Originally Posted by Akitawa

Wear your smallest swimsuit and nothing else. If it's not too painful, use cloth pin to your nipples. Now let's test how courageous you are. You need to edge three times from humping with your sister pillow. You can't move the pillow outside of her room.

After that, while keeping your position and play your video. Put your face to the pillow and raise your ass. If you smell it funny, you can only clean it by sucking. Play with your clit to keep your hand busy. If you don't clean it clean, maybe your sister will be able to smell it and notice how pervert her sister is.

For the entire day, you need to keep wearing your swimsuit underneath. You can only cum at night before sleep while writing your report.

I have completed the first part of this dare. I was able to find an old swimsuit from a few years ago that I would definitely consider to be my smallest. I have been wearing that for the day. It’s been a bit uncomfortable but I’m getting used to it.
I completed the edging with my sisters pillow. It definitely did have some of my juices on it so I did suck them off. It still does smell like my pussy but my sister will not be home for another 2 weeks or so, so I’m not too concerned about it.

I’m debating possibly washing the pillow. I know the dare said not to be I feel like it would be a bit messed up not to, considering she sleeps on it. What would my punishment be if I do wash it?
I haven’t cum yet and will wait until before I go to sleep.

[Akitawa]

Originally Posted by Lushrant

I have completed the first part of this dare. I was able to find an old swimsuit from a few years ago that I would definitely consider to be my smallest. I have been wearing that for the day. It’s been a bit uncomfortable but I’m getting used to it.
I completed the edging with my sisters pillow. It definitely did have some of my juices on it so I did suck them off. It still does smell like my pussy but my sister will not be home for another 2 weeks or so, so I’m not too concerned about it.

I’m debating possibly washing the pillow. I know the dare said not to be I feel like it would be a bit messed up not to, considering she sleeps on it. What would my punishment be if I do wash it?
I haven’t cum yet and will wait until before I go to sleep.

Sure, does the pillow have a case? If yes, you can't shroud it with the same case. If she notice the different and ask about it, your answer must contain "Juice" and "Smelly". If not, wash it but the day before she comes home, try this dare again but this instead of edging, you only need to play with your boobs for five minutes, the entrance of your ass three minutes and one minutes for your clit. The goal is to resist the pleasure and not letting any juice leaking.

To compensate it, sit on your own pillow naked. Without touching yourself, you need to wet it. Imagine any scenario that excited for you like your sister came home and saw you humping with her pillow.

Within 30 minutes if you can't do that, finger your ass with a lube. The last moment when you want to come, take it off immediately. Sleep in your suit with an ice cube in the entrance of your ass. (Put the ice on your mouth first to remove its edge).

If you manage to wet it, spread your pussy lip and take a picture. Cum once and take another picture. Don't forget to compare them before sleep.

[Lushrant]

Originally Posted by zephyrnem

What is your favorite part about being naked outside?

So...pick five places outside (at least 50 m apart...or 3 to 4 minutes walking time) Do this before you start the dare. You want places where you can stop...or maybe even sit. Up to you.

Wear four pieces of clothes (shoes can count as 1 for the pair).

Leave your house at night. At each station...take off a piece of clothing AND then stay there for 3 minutes before moving onto the next station. At station five you will sit there for 3 minutes naked AND THEN you must stay there until you cum.

Now...you can either stop at each station again for 3 minutes and when the time is up NOW put on a piece of clothing at a time at each...OR...you can gather your clothes in a bag and NOT put them on and walk home naked without a time penalty at each station. Up to you.

If you do not follow the rules you will be punished and the punishment may involve making you be caught naked (hahahahaha) or not. As always...you are in charge and are having fun. Enjoy!

(Though I wish I was here to watch and make SURE you went through with the dares!)

Good morning. I attempted this dare last night but may have failed. Everything went okay at first. I had the stations setup at the walking trail near my house. I was going to use the 5 in my yard but they were not far apart enough. I got to all 5 and had all my clothes off. As I was masturbating and about to cum I heard a noise which sounded like somebody may be near. I kinda panicked and grabbed all my clothes and went home. Once I was home I finished masturbating and came in my bed. Looking back; I don’t think there was actually anybody there but I didn’t want to risk being seen.
I understand that there will be a punishment for this and do accept whatever it may be, as long as no photos or videos are involved.

Originally Posted by Akitawa

Sure, does the pillow have a case? If yes, you can't shroud it with the same case. If she notice the different and ask about it, your answer must contain "Juice" and "Smelly". If not, wash it but the day before she comes home, try this dare again but this instead of edging, you only need to play with your boobs for five minutes, the entrance of your ass three minutes and one minutes for your clit. The goal is to resist the pleasure and not letting any juice leaking.

To compensate it, sit on your own pillow naked. Without touching yourself, you need to wet it. Imagine any scenario that excited for you like your sister came home and saw you humping with her pillow.

Within 30 minutes if you can't do that, finger your ass with a lube. The last moment when you want to come, take it off immediately. Sleep in your suit with an ice cube in the entrance of your ass. (Put the ice on your mouth first to remove its edge).

If you manage to wet it, spread your pussy lip and take a picture. Cum once and take another picture. Don't forget to compare them before sleep.

Thanks, I’m going to hang on to this dare and do it all closer to when she is coming home. I believe she will be home next weekend or the weekend after.

[zephyrnem]

Before someone jumps in...I am thinking of a punishment for the dare you failed to complete. In order to make it devious and fun...it may take a while, but it is coming

[NotMe237]

Originally Posted by NotMe237

Also for another dare, do the last dare I gave you (masturbating face down/ass up while fingering your ass) But it must be done outside nude away from your property and your ass must be facing the street. Also you should leave you clothes inside as usual.

If you have to hide when someone is coming, that is fine. But after you finish hiding and reassume the position. You must apply 25 spanks to each cheek before you can continue masturbating. And remember, you must cum with your finger still in your ass. Enjoy!

Just wanted to see if you had a chance to do this dare yet

[Lushrant]

Originally Posted by NotMe237

Just wanted to see if you had a chance to do this dare yet

I’m going to try and do it this weekend. I need to think of a good place that is facing a road but not too much of a risk of being seen. Hopefully I can do it tonight.