25 replies to this topic

[wannabeasissy]

I was curious what every ones most daring thing they have done? I would have to say I have quiet a few. But the one I did most recently might be my most daring.

here goes.

I have been planning all week that I wanted to do this, I didn't know exactly what day or anything like that. I guess I was just waiting for a urge. Seeing as I still live with my family I have to be careful about my activity's. It was around July 3 when I had an idea go thru my head that I couldn't get out. Let me first off say that we have a park about a mile away from my house on the river. During this time of year they have a 3 day forth of July celebration. Its actually pretty big/popular. My plan was to go there during the night when no one is there and walk around in a fully soaked/messy diaper. I kept putting it off until the 5th. I was worried that there would still be tents up and stuff and they would have around the clock security watching the park making sure no one steals anything. So I decided to take my chances and get everything ready. I got my diaper ready, I also grabbed a very short pink frilly skirt, and decided that was enough. But then I started thinking that I really wanted my diaper to be sagging alot. I just finished drinking the water from a large water bottle and decided to fill it up with pee, and wait till 4:30 in the morning to do my naughty activity. I was so nervous and excited about doing this. it got to around 4:15 the bottle was almost completely filled. I was starting to pump myself up to do this. I went up stairs but the diaper on, put on some shorts. Shoved the skirt it my pocket grabbed the water bottle, keys and wallet and started heading out the door. I got to the park looked for a decrete parking spot, and got out. I was so happy to find out everything in the park was packed up, and gone. The place was really dark cept in the areas where there is street lamps on the path, and by the main road. I went all the way up next to the river and decided to finally do this. I took my shorts off. Put my skirt on, I took the water bottle out and started dumping it in my diaper. Felt so good. It obviously wasn't as good feeling as freshly wetting a diaper but it was still a nice sensation, considering it was still pretty warm. I filled the diaper up to the brim. The diaper was so full felt exactly like if you wore a diaper into a swimming pool and got out. I decided to start walking around the park. I went next to some benches and sat on the ground. Usually the main road is pretty empty at this time of night, but one truck started driving down the road. I started freaking out cause I was pretty much in the light. I started walking towards the river where a tiny hill leads down and I would be hidden if I got on the ground. I wasn't sure if the guy or girl in the truck saw me or not but IM 99% they slowed down. They eventuality left and I decided it was time for me to head home and think about my adventure. Took the diaper, and my skirt off put the diaper in the trash can pulled my shorts up and went home.

IM not sure if I enjoyed it as much as I was thinking I would in my head. The whole time I was worried about dropping the keys, and phone out of my pants pocket while carrying them. Also I decided not to mess the diaper as I was just a nervous wreck during the whole thing, and I would have to clean up at home. Since the park bathrooms are locked every night.

Even tho it was night and no one was around. The idea of walking around a park in a wet diaper and short skirt was pretty awesome.

Note: Sorry grammar, punctuation police. I am no writer and truthfully don't want to waste my time being insanely anal about that sort of stuff. Or IM just stupid and we can leave it at that.

[kootzkoo]

you really think wearing/wetting a diaper in public is that daring? you wouldn't be the first one to wet a diaper in public,

but it does take someone time to have the confidence to wear diapers in public. (even if they are covered up and hidden well)

I am a pretty crazy guy (in a good way) I have worn a big green dress in public with a diaper underneath

The dress I wore looked like this:



The public does care though, people look make comments but my friends are all open-minded people who just like to have fun.. so we just laugh it off.
Even if I did put work into passing as a female, it's not a dress most people wear in public so it would still attract attention -

There is not much that I'd be afraid to do, but I don't think I'd ever wear a diaper out in the open in public (unless it was a public change room at a gym) - I wouldn't wear a diaper out in the open at a costume party either because I know I would wet it - plus my friends know about my diaper thing so they'd probably just wouldn't want me to wear it out in the open knowing that I would wet it and it'd show on the front of the diaper




I love my dresses!

[wetman]

...
I have worn a big green dress in public
..

I love that dress (blue would have been my choice, unless I'd find a nice redhead wig), but I couldn't pull it off.
Big envy smile to you!

[glycerine]

Not with a diaper on, but...

When I was doing business in NYC I transformed into Jennie and rode the subway from the Millennium Hilton up to Broadway and went to a musical. What really embarrassed me was that I'd put on too much perfume. By the time I noticed I was already out the door. I wish I'd been a diaper-wearer back then! I was too shy to go into the ladies toilet (someone might talk to me!) and boy, did I have to pee by the time I got back to the hotel.

[BabyJune]

Sex in the back room of our local public library. I worked there and had the key to the building.

[dressupDV]

Not with a diaper on, but...

When I was doing business in NYC I transformed into Jennie and rode the subway from the Millennium Hilton up to Broadway and went to a musical. What really embarrassed me was that I'd put on too much perfume. By the time I noticed I was already out the door. I wish I'd been a diaper-wearer back then! I was too shy to go into the ladies toilet (someone might talk to me!) and boy, did I have to pee by the time I got back to the hotel.

When I lived in NYC, I used to wear panties under tights and go roller skating. I'd go into adult video stores with booths and show off my panties in there. That was a rush and a half!

[spoonchicken]

Once upon a time, I got "dressed" (tight sweater with bra & fake boobs, pink plastic mini-skirt, pink satin/nylon ruffled panties, white belt w/white stockings, white 3" heels) ,and then drove over to the "red light district" of town. I already needed to pee badly before leaving, and by the time I got there, I was bursting to go. I drove around the block for a while until I truly couldn't hold it anymore. Then I pulled over, jumped out, and instantly had to let go. I leaned back against my vehicle as I helplessly wet my pants. I was clutching myself as if to try and hide or stop what I was doing, although I was really just making sure the back of the panties were just as wet as the front. So, there I was in public, wetting myself while crossed-dressed. I was rocking my hips back to front, and alternating between spreading my legs and letting the pee cascade directly down to the ground, and clutchinh my legs together and soaking my white satiny stockings. It was a huge pee that lasted about a full sixty seconds, during which time anyone walking by on the sidewalk would have seen me. But the only person who walked by( a cute guy) was too busy talking on his celphone to even notice! I finished peeing, stepped away from the huge (!) puddle, hopped back into my vehicle, and "frantically" fapped off before driving away...that was a LOT of fun...gotta do it again sometime soon.

[willnotwill]

I've worn a variety of female clothes in public: Cheerleader dress, skating skirts, wedding dress, tutus.
The Hash House Harriers (a group described as a drinking club with a running problem) hosts events around the country called the "red dress run" where all must where a red dress. I usually wear a red spandex skater costume. They have in our city, the prelewd lingerie run which has people wearing everything from underwear on up. I wore a little girl nightie and carried a large teddy bear for that once.

[matt28]

Worn a wet diaper to a massage

[Bettypooh]

Daring? Walked right past several people above my boss who knew me as they got of an elevator while fully dressed in my female personna I passed pretty darn good and I figured I'd draw less attention to me that way than I would if I tried to hide. I could have lost my job and got the same for my boss too but the tactic worked- they didn't more than glance my way as they were absorbed in their own world so I left them there in it and went on It took a few minutes for me to settle down after I got through the crisis (I'm staying on topic; I have done many far more daring things not related to this that should have left me dead but didn't

Bettypooh

[spoonchicken]

At the risk of being egotistical about it, I sincerely think I had the most daring experience...lol

[thong5]

I was in my sissiy mode wearing a blue denim mini skirt with a very nice frilly top and of course a diaper and i went to a walgreens to get some smokes at about 2 am. I walked in and to the counter and the cashier a man looked at me and said i had nice legs ( turns out he was gay like me ) I got my stuff and paid and walked out very arroused. Haven't done it again tho but it was fun.

[jesica]

Several months ago, I went to some friends house with my hair in curlers and a hair net. I had told them I had gotten perms years ago and had sleep in curlers and I told them I had found some curlers in my attic and was going to do this. Well, I did and visited for several hours with the curlers in my hair. Someone took them out for me and styled my hair. We all laughed and thought it was funny. I did wear a hood over the curlers going out to the car.

[wetman]

The 'daring thing' was just forced on me last week: I was out for an 'all night nappy drive', as I sometimes do (I don't wear around the family, read my profile...), and had my last catheter in. All went more or less eventless, except that my abena M4 leaked earlier on and I got my trousers a bit wet. I changed at a service station and then took the trousers off in a lay-by. As I also crossdress (but I don't usually mix the two things), I had a few ladies things in the car, too. The most neutral thing to go over my nappy was a pair of leggings, so I wore them.
And I got stopped by the police an hour later (I apparently was driving rather slow...). My nappy was sagging again quite a bit, and with the leggings on it must have looked quite toddler-ish. I had to step out of the car for an alco-test and the policeman looked at my lower regions several times in a rather amused way.
I stayed neutral and nothing more happened.

I think I might go for another drive this Friday; anyone want to join?

[ghbabdl]

i was on my way back from a night out in London. I had spent the evening in the pub drinking and I was wearing a diaper under my trousers. I started to wet about 30 minutes before we all left to avoid the diaper swelling too much even though I cannot remember holding back at this stage.As i meandered home on train and tube I continued wetting quite heavily and the diaper was soaked and had even started to leak through my trousers.

It was one in the morning and I started to walk down my road, it is a cul de sac and I am at the end. Suddenly I stopped after a couple of houses, sat on a bench and took off my trousers and underwear leaving me standing there in a formal shirt, soaking wet bulging diaper and shoes. I just casually walked all the way home, past the houses, past some flats and up to my front door.I even videoed myself on my phone :-(

I cannot believe I did this and could have bumped into anyone. Am I crazy ???

[wetman]

...
Am I crazy ???

Yep.

[baby smokey]

Freaking amateurs, come spend Halloween with me. I dressed up in a PVC French maids outfit, and some very thick diapers, and went in to the local Walgreens, and picked up a pack of diapers, the ladies working there said I looked very cute. It's not the first time or last time I've done something like that.

[AbriForm]

A friend knocked on my door unannounced. Not expecting anyone, I was decked out in all pink.

Swallowing my pride, I didn't change and let her in. She knew I wore diapers (hated the idea) and that I was sissy (loved the idea).

She could not stop laughing for about 10 minutes straight.

[abycpl]

I only get crazy about once a year with "outing" myself. I one day may regret it as someone I know may come across a photo of mine. I have probably had over 1000 photo's taken of me over the last 3 years by all kinds of people. For the most part I have had good experiences with only a handlful of times I have been harrased for going out. But the pleasure and joy I have gotten from all the good experience totally out ways and makes it all worth while. Im consider myself to be a wanna be compared to others. If it were not for halloween I would probably never get the guts or opportunity to go out. Others that go all out like riley and heidi lynn. They set the bar way higher than I will ever reach.

[blitheringidiocy]

When I was living alone in a secure apartment I would often do some daring things while taking the trash to the bin.
Most of the time it was relatively minor things, and fairly concealed. Wearing breast forms under my jacket.... female jeans instead of male... once or twice I wore my heels out for a quick drive.

The most daring and scariest I've done... was wearing a bambino diaper, fairly transparent yoga pants, high heels, breast forms, and a sweater. Overall you wouldn't notice at a glance... but anything more and it would be obvious. I took the trash out in the middle of the night, making sure the coast was clear as I clicked down the stairs. After exiting the building, a sudden sense of dread came over me. I DON'T HAVE MY KEYS. The doors to the apartment are always locked requiring a key to enter the building. Immediately I turned around catching the door moments before it closed. My heart raced as I caught my breath. Immediately abandoning the mission, removing my heels and fleeing back to my suite. This was the closest I have ever been to being knowingly caught. I can only imagine the horrors of being trapped outside at 3 am... wearing what I was.. trying to get back into the apartment complex.