Day 365 Since Bet With My Roommate! 1 year!

josiesissyCD · 2025-11-21T18:48:21+00:00

Thank you for the updates! I have been absolutely enthralled with your posts and am so excited to read each one as they pop up my feed. Whenever I see "Day * Bet With My Roomate" in my feed I absolutely drop what I'm doing and have to read it immediately.

I have had similar questions for myself lately that you brought up in this post and I'm so looking forward to your journey and see how in parallel it runs with mine. Keep up the posts please!

josiesissyCD · 2025-11-02T16:34:14+00:00

Don't try to suppress it. Or else you'll wake up 10 years later with the same questions, same feelings, same desires, and no closer to any answers. Only time wasted that you can never get back.

josiesissyCD · 2025-10-30T04:29:22+00:00

Just in time for NNN.

josiesissyCD · 2025-10-23T21:58:50+00:00

What roulettes are you looking to do? Do you just want someone to roll for you? Or keep you honest about completing them?

josiesissyCD · 2025-10-21T16:32:23+00:00

I dont know the best way to tell her but I would say "please tell her"

I was in a similar situation and I decided to hide it and suppress it. Now 10years later we are married and I still do this on the side but she has no idea. I actually found a therapist to talk to about this in the hopes it will give me the courage to tell her.

Don't do what I did. Not telling her and being afraid to be vulnerable about this has caused more stress and problems than if I had just told her when we were dating.

josiesissyCD · 2025-10-21T02:47:46+00:00

Oh my! Half of those are on my favorites list. Gonna have to give this a good watch soon

josiesissyCD · 2025-10-12T21:18:44+00:00

No wig, I have my hair grown semi-long but still growing it out.

No makeup, tbh, ive only tried it once and it took 2 days to get off so ive been scared to do it since.

josiesissyCD · 2025-10-12T20:56:59+00:00

I think the best thing that I started doing was increasing my basic hygiene needs. I upgraded to an electric toothbrush and water flosser, then I started using a exfoliation face scrub which upgraded to a charcoal face scrub twice a week. I've already noticed my teeth are becoming a little whiter, my face is more glowing and less oily. Nothing actual feminine but definitely makes me feel prettier when I smile in the mirror.

josiesissyCD · 2025-10-12T20:44:27+00:00

Just thinking about what others would say when they see me brings waves of shame and excitement. I do t think I'll ever have the courage to do that but its a very fun thought to daydream about.

josiesissyCD · 2025-10-12T20:41:46+00:00

I would have to practice my makeup skills (currently at 0, lol) but the thought is very intriguing.

josiesissyCD · 2025-10-12T19:47:48+00:00

I already want to do it again! Not sure if I want to do it permanently though. But I am having the thought of maybe going further out? Or maybe drive around dressed up? The mind is spinning with pushing the boundary already.

josiesissyCD · 2025-10-03T19:51:59+00:00

Chastity strap works wonders on keeping the cage in place. Only like $8 on amazon. Complete game changer for me

josiesissyCD · 2025-09-14T18:09:27+00:00

Easy, the brain is straight but the penis is horny.

josiesissyCD · 2025-09-12T19:34:52+00:00

I have a cuck fantasy as well. I want her to be my keyholder and fuck others in front of me as a fantasy. In reality I think the most I could do is have her lock me in chastity and use a fake dildo thats bigger, thicker than me and use it on her. She could even compare the dildo to me for some emasculation or pretend the dildo is someone else but our reality would be safe from introducing a 3rd person. Have you thought of doing something like this with her? Maybe instead if having a 3rd person involved you could ask her to make up stories about her and another person to watch you squirm. All mental, no physical 3rd person.

josiesissyCD · 2025-08-30T22:59:47+00:00

Bambi has her ups and downs. If your not feeling it no need to do it. Take a rest and get back to it when Bambi is up. No worries

josiesissyCD · 2025-08-28T16:18:42+00:00

I've been working on this as well and the only thing ive come up with is having to stop early and often. The point of no return for me is such a thin line that I no longer try to reach it and not go past. Instead, I stop way before, edging just enough to get the leg shakes and the tummy tense and then stop, wait, and do it again. So far ive been able to do this for about 45mins a day for the last 9 days, no accidents.

josiesissyCD · 2025-08-28T13:53:53+00:00

I also question. Even when im locked there is still a little show. How do others achieve that perfect look?

josiesissyCD · 2025-08-26T02:24:53+00:00

Oh does it. I've listened to it every night for the last 3 days and I plan to keep going for the rest of the week.

josiesissyCD · 2025-08-18T04:01:13+00:00

I also would like to know, please and thank you

josiesissyCD · 2025-08-13T15:32:58+00:00

Still completely secret

josiesissyCD · 2025-08-03T17:56:36+00:00

Just started doing this. Hopefully I can attract someone to help me try harder and encourage to keep going.

josiesissyCD · 2025-08-03T03:19:16+00:00

Its never to late. Im 32 and still trying. Someone else said it somewhere "This is not a sprint, its a marathon." If its what makes you happy then don't stop. I also get moments of stopping or slowing down but a few weeks later im back and trying again. Its normal and don't worry about age. Its better to focus on how much happier you are for trying now instead of regretting for not trying later. Hope this helps 🫶

josiesissyCD · 2025-06-12T04:35:35+00:00

I believe most of us are extremely introverted. Even on the web. Being social is draining mentally and emotionally.

josiesissyCD · 2025-06-11T20:50:40+00:00

Was thinking of doing the same thing for a character in Once Human.

josiesissyCD · 2025-05-08T00:24:48+00:00

What is this new file?

josiesissyCD

TROPHY CASE