30/09/2025
It started simple enough, I asked her to start wearing more revealing clothes and encouraging her to stop wearing a bra whenever she went out. It took some time for her to agree but eventually she did with the help of seeing this site and I started noticing that she began to wear some relatively tight shirts that made it fairly obvious that she was braless and showing a little more cleavage whenever she went out with her friends.
I always reassured her and let her know how hot she looked, and I also made sure to mention any other guy would think so too, and I told her I actually loved to think about all the attention she might get. It went on like that for a couple of years until going our braless became basically the norm for her.
Both of us worked at the same place and she got along pretty well with my friends, particularly with two guys that lived together, and eventually we started hanging out together a lot.
One time, we were invited to our friend's place which had a big pool and when we got there, it was just the four of us. I honestly thought she wouldn't feel comfortable enough to get in the pool but, to my surprise, she went to the bathroom and came out wearing a small white bikini that accentuated her ass.
We all got into the pool and spent the afternoon chatting and (very indiscreetly) enjoying the show while she swum around. After that, every time I mentioned noticing how they were staring at her and that I didn't blame them, she would laugh and brush me off.
On another occasion, we went to a party a bit far from where we were living at the time. She didn't have any spare clothes but she jumped into the pool anyways and had to borrow a friend's shirt (the same friend who owned the house from the previous story).
It was an oversized white shirt, and she was wearing a tiny blue thong underneath, which was clearly visible. He was going to give us a ride home, so she got into the backseat and the three of us talked for a while but she eventually turned around and laid in the backseat with her back facing us, exposing some of her ass and her thong for the rest of the ride. Needless to say, we spent the rest of the night staring whenever we had a chance until we got home.
Doing anything more than that is not something we would really do, so I suggested trying our luck with online anonymous exhibitionism and, surprisingly, she agreed!
So one night, we decided to take some pictures; I chose her outfits and poses, and after we finished, we posted them on the internet. I was amazed by the number of views and comments they got. The idea of her putting herself on display—being seen, desired, and lusted over by others—was a huge thrill.
One person even offered to send her some lingerie in exchange for photos of her wearing it and she agreed but, unfortunately, things happened and the opportunity was lost. I keep wondering how that stranger would have dressed her up. We ended up deleting the pictures but I am sure they are still out there somewhere.
If you read this far, I really appreciate it! I know they aren't as wild or intense as other's stories here, but they are something I would have never imagined experiencing and definitely enjoyed them a lot!
Look out for a possible post coming up too. Hopefully in the next couple of weeks but she said she's game.
Poster:
Goonies