##Main Story
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Here’s another story of a time I lost a challenge. It wasn’t really a formalized one, but Derek still made a challenge to me, and I lost it anyway.
The backstory on this one can be found in my profile for my other posts, but Derek took Emily out on a date at the park one day. I was at home straining in my cage, and She sent me a picture of herself in the dress she wore out. Usually Emily will send me pictures and not say anything, nor respond to my texts while she’s out, and Derek will be the one who messages me things, usually him being an asshole or rubbing something in my face or trying to be superior.
A little while later, I got a different picture of Em, and Derek texted me around the same time and was like “Notice anything different about those pictures?” And I looked at them and it turns out she had changed outfits, and was wearing something completely different from the last picture. So of course my cage is now straining and I’m thinking about how he must have fucked her outside and thats the reason for the wardrobe change. I never knew Emily to be an exhibitionist, and she was always worried about being seen as a slut or something by other people.Anyway, that outing finishes and Em comes home to me and ties me to the bed for some teasing. She removes my cage and is gently edging me and I ask her a bunch of questions about what happened.
She tells me that Derek told her to pack a change of clothes, and also not to wear a bra or panties, and yes, they did go to a secluded area of the park and he fucked her there. Unlike their usual sex, this one was only for his pleasure, and he had her on her knees, no panties under her dress as he fucked her from behind for a few minutes. Then he pulled out and came all over her dress, forcing her to change all her clothes. The other outfit she brought was a sweater and jeans, so she had to put that on and take the dress off in the middle of the park, so her boobs were definitely out at some point in the changing period.So then Derek is texting me all smugly, saying stuff like “She would never bend over in public to let your little dick inside her” (mine is substantially shorter and thinner than Derek’s) and basically just gloating that he got her to do that in the first place (it is admittedly out of character for her). And he was just so relentless and I thought that Em would surely do the same thing for me, I just never tried anything like that.
A week or two later, I plan a similar date for us to go to the park and find a little secluded spot to take her. I’m not sure if it's the same one, but this is a huge park with lots of hedges and areas that people don’t go to very frequently, so the spot is effectively the same type of vibe.
We’re having a fun little date, and I try to convince her to unlock my cage so I can fuck her out here the same way Derek did. She pulls open my pants and pulls out the cage, and I think she’s about to unlock it. Then she slips off her shoes and starts rubbing her feet on my cage, stroking my penis through the little holes in the cage, and driving me up a wall.
She keeps stroking it for a few minutes while I try and convince her to take it off, but she doesn’t, just keeps giggling at me and rubbing her toes on the cage while I’m leaking, and stroking/squeezing my balls gently with her hands too.
Then finally she told me “I think we’re gonna have to keep my little guy all locked up this time” with a wink, and stopped her teasing.
Later that day, Derek texted me “Haha, I told you it wouldn’t happen. That’s why you’re in the cage and I fuck her more often than you do”
So Emily definitely knew about what he said to me, and she knew that I was going to try and fuck her outside too. She even texted Derek to let him know he “won”, probably something like “oh he tried to get me to fuck him in public but instead I just teased his little cage until he was leaking and so horny”.
##Smaller related story
And a little bonus mini story that doesn’t involve a challenge, but has Em doing more exhibitionist stuff with Derek (She always told me she’s not into that)Another time she was hanging out with Derek, after he took her to go get a pedicure in his favorite color (white) they went to this little area that was somewhat public, but not like a busy street or anything, and there was a swing there. It’s near Derek’s house.
I got sent a picture of her sitting on the swing with this huge bashful smile, like she’s embarrassed or something, but the smile is also very naughty, and she’s totally flushed for some reason. And I don’t really think twice about that picture, but then a few minutes later, I get sent one of her on the same swing, but her top and bra are taken off, and she’s covering her boobs. All this in public! And I’m wondering what happened there or how this came to be. Later, she told me she was “feeling adventurous” that day, and the way he convinced her was he had her tied up and edged her with his cock for like 30 or 40 minutes. Then, he said they were done for a while, and they were gonna go for a little walk for a bit. Naturally, Em was Irate because she was in the middle of being edged and thought she was going to get to cum. But he got her to put her shorts on (no panties) and her top and they went on a little walk. The whole time, he was groping and teasing her, making sure she stayed horny, and when they got to the swing area, he told her to take her top off.
But she of course said no, and they argued back and forth until he said he wasn’t going to fuck her when they got back unless she took the top off, and she finally agreed to take it off for a bit and let him take some pictures.
And Derek himself told me that the first picture he sent me, the one where she was smiling embarrassedly, was taken at the exact moment when she agreed to take her top off for him. He said she was wet as fuck in her shorts and couldn’t go without a good fucking. And he even said “There’s no way she would have taken her top off for your little dick”