Cassies Findom Adventure Ch 03

Edward -- or Sherry as he was now known -- had done exactly as Cassie had told him. He'd gone out and bought a little pink cage to lock his cock up in and a pair of lacey pink panties to match.

Cassie had taken their communications from emails to Whatsapp to makes things more convenient. She's saved his number in her phone as "Money Bitch". She was staring at a picture Sherry had just sent. He was standing in front of a full length mirror completely naked with only the cock cage to protect his modesty. He was looking down shamefully but through the humiliation of being put in chastity, Cassie could see the arousal. The pathetic man actually liked being commanded by a young girl. Any real man would have taken charge of the situation and put Cassie in her place by now, but Sherry was no real man; that was why Cassie called him Sherry.

[Put on the panties] she wrote.

{Yes Mistress} came the reply.

Evie giggled when a few moments later she received a picture. Sherry was standing in the same position only this time he was wearing the lacey panties. Evie felt a giddy kind of buzz at the power she had over this man who was roughly 40 years her senior. It was something she had not experienced before. She sure was enjoying it though. Who knew that such power over another could be so intoxicating.

[Such a pathetic little bitch letting me take control of you like this, aren't you?]

[Yes Mistress] Cassie could feel the shame radiating through the two simple words.

[Be a good girl and turn around for me. Pull the panties into your crack so they look like a thong. I want to see how good an ass my girl's got] Cassie was laughing as she typed, not quite believing the way she was speaking to Sherry. It wasn't like her at all.

She laughed even more when Sherry complied and the picture arrived. His pasty white ass cheeks were bare, the pink fabric peeking out from his ass crack. Cassie's boyfriend would never have allowed himself to get into such a position. He wouldn't even wear her panties as a joke. But Rhys was all man, dominating and strong. Sherry was not.

[How do you feel, Sherry? Are you enjoying yourself?]

[Yes, Mistress. It's a bit undignified though] He wasn't wrong there. There was nothing dignified about being ordered around in a pair of panties.

[I think you've still got some dignity left. Let me try to take it. Get on all fours, ass facing the mirror, and snap another pic]

Minutes ticked by with no reply. The message showed as read but no "typing" notification appeared. Had Cassie gone too far? Was that a line of degradation that even Sherry would not cross? The answer to those questions was no. Apparently it had just taken him a little longer to get the angle right. A picture of Sherry on all fours, with his pink-pantie clad ass pushed up in the air arrived in the chat.

Cassie could not contain her glee. It was the most hilarious, degrading, and pitiful things she'd ever seen.

[Mistress, I'm so turned on right now. Please may I touch myself?]

Cassie considered his request for a moment. He had been a good little submissive and carried out her instructions without argument. Perhaps Sherry deserved a reward. On the other hand, she'd only just put him into chastity, to let him remove the cage so soon would make it a rather toothless rule.

With a real sense of authority that filled her with feelings of superiority, she typed a reply. [Absolutely not. Go and take a cold shower. I've got things to do now so don't you dare disturb me and make sure you wear panties all the time. Sissies don't get to wear men's underwear]

Cassie spent the next couple of days wondering where the line was in this whole depraved yet enjoyable situation. She asked herself if she was truly blackmailing and humiliating this "man" against his will or if he was simply letting her because he loved it. After looking through a few findom/blackmail kink forums on Reddit, she decided to give Sherry a way out if he required one.

[Sherry, I'll admit that I'm really starting to enjoy degrading you and forcing you to send me money and I'm not sure how far I might go. For that reason, I've decided to give you a safe word so that I know if you really want to stop this process. If you want me to stop just to take a break or forever you have to say "Hilary Clinton"]

[Yes, Mistress, that's a very good safe word. The mention of Clinton would ruin anybody's bedroom fun]

[Now that we've got that boring business out of the way, let's talk money. I want to see exactly how much dollar you've got to your name. Send me the login details for your internet banking]

Several times the "typing" notification appeared before vanishing and then appearing again. Sherry was having a hard time coming up with a suitable reply. That didn't bode well and Cassie felt a dead weight in her stomach as she anticipated the appearance of the safe word.

[I don't think I should give you such delicate information, Mistress. I could send you a screenshot of my account if you want to see?]

Cassie pursed her lips, finding that she was genuinely annoyed at his refusal to comply. Her thumbs tapped her screen furiously. [Listen carefully, bitch. This is not a negotiation. I have photos of you in various compromising positions with your face in the shot. Do as I have told you or I will send those pictures to 5 people on your contacts list. Now]

When Cassie sent the message a hint of guilt gnawed at her. Perhaps she was being too mean. She was new to this after all and didn't know exactly how to embody the character. She'd given Sherry an out. If she'd gone too far he needed only type the one name that would end it all. At least, that was the idea.

His next message made no mention of the former Secretary of State and First Lady. It contained his bank account details.

Fingers trembling with anticipation, Cassie downloaded the banking app and entered the details. She was in. She was actually into this man's bank account. She'd known he had a high paying job but she still wasn't prepared for all the money he had stashed away. His checking account and his savings account were both filled with more money than she'd ever had in her bank account. He was very comfortable financially. No -- she was. After all, this wasn't his money anymore, it was her's now.

She quickly went into the security tab and began replacing all of his details with her own. Her mobile number. Her email. The only thing she couldn't change was the address. She changed the username and chose a new password. If he tried to recover his account the security codes would be sent to her instead of him. She'd taken full control of his finances. And she felt on top of the world.

[Sherry, log into your account for me]

Cassie grinned broadly when a recovery text pinged into her inbox. 5 minutes later he replied. [I can't. I can't even recover the account. You've locked me out, Mistress.]

[Yes, I have. Your account is now my account. Your money is now my money. If you're a good bitch I might throw you a few dollars for groceries but otherwise, your funds are totally mine. Understand?]

[Yes, Mistress. I hope you enjoy your new funds]

[What are you?]

[I'm your bitch, Mistress.]

[Yes you are. You can take off your cage tonight since you've behaved so well. But you put it straight back on once you've finished and you will not be taking it off again for a very long time]

[Yes, Mistress. Thank you, Mistress]

Cassie stared at her screen in disbelief. Not only had he not even tried to thwart her efforts to take over his finances, but he'd even thanked her for it. What a sad little man. No, what a pathetic little sissy.

Cassie opened the Amazon app. It was time to do some shopping.