I had my last orgasm late Saturday night. On Sunday, I put myself into chastity. Even though I don’t have a keyholder right now, I’m doing my best to resist the urge to unlock myself. Posting this here should help keep me motivated for longer wear. I’ve kept the keys close by just in case it gets uncomfortable and needs adjusting, but if Thursday passes without any adjustments needed, I plan to leave them at work over the weekend to cut down on temptation.
My target is one week—making it until Saturday—but if things feel manageable, I want to extend as far as possible. My previous best was four days, and this has only been my second time wearing a cage ever. The CB2000 fits well enough but creates quite a prominent bulge in men’s jeans. Since I do kickboxing, I usually take it off during those sessions, which don’t resume until September, so that was the reason for stopping before. Now, though, I’ve switched to overnight wear starting yesterday with much less social activity around me, giving me a chance to push my limits further.
As someone who identifies as a sissy, thought sharing pictures of my underwear might help too. I’m also exploring subtle yet realistic ways to lean into that side without being obvious. Right now there’s a bow on the cage which stays on except for showers and changing panties. I plan to paint my toenails soon; once I get out shopping (hopefully today or tomorrow), I’ll pick up nude pantyhose to wear under trousers at work, maybe even a butt plug or vibrating cock ring for some teasing pleasure. I’m also considering discreet diapers as an alternative to panties for extra humiliation.
Chastity: Me in the cage; note that the bow stays on unless it’s shower time. Chastity Day 1: These aren’t exactly glamorous, but there’s only one way to go! Chastity Day 1 Chastity Day 1 Day 2: Definitely sexier options. Chastity Day 2 Chastity Day 2 Day 3: These look cuter and more sissy-like than the previous ones. They also flatter my butt nicely. I put these on earlier today. Chastity Day 3 Chastity Day 3 I’m open to ideas that might increase my frustration. Ideally, I’d like to reach a point where leakage is constant inside the cage.
Jessica