(22M) bisexual. I have been into chastity for several years but never really shared it with anyone until now and due to bad self control haven't been able to go longer than a day and a night.

This will seem convoluted but it was and I can't change reality

I am in a Discord with a bunch of friends and friends of friends and we were casually chatting about kink. (The discord is just really relaxed and LGBT+ positive and you have to be a friend of a friend.) So I think I showed some really cute porn or we were talking about hardcoded (great game btw) or something in that realm but I work from home and I said I needed to stop being horny and get back to work. One of the women in the call joked about chastity and I mentioned (not very casually) that I had one and it was a great idea and I went and put it on. I think most people either thought I was joking or just thought it was funny and the conversation moved on.

Later that day the same woman messaged me and asked if I really had put on the cage and when I said yes she asked if I had worn it all day. I said yes because I was still wearing it and we talked privately about some kink stuff and she seemed excited to have someone to talk about being a dom with and I was excited about having someone to talk to about being a sub. We both normally take the opposite role and I mentioned that I was going to be visiting the city she lives in next week (we live a 2 hour ferry ride apart) for a family thing and some personal stuff. She mentioned we should hang out. We had talked about her new metal whip (very small hand held) that she wanted to try on someone (like my arm or somewhere not super sexual) and that came up and I said she should bring it and she can have a go.

The conversation wrapped back around to chastity and she asked how long I had worn it before and I admitted that the longest was a day. She said I should wear it overnight and I admitted that I had done that so she immediately said “3 days”. I was flustered because that was longer than I had gone before but she was adamant so I said yes and put the keys into a letter with her name on it. (no I didn't send them to her we just met and it wasnt suppose to go on that long anyway just some fun) but we started talking a lot and she started asking me if i would ever try specific things like prolonged whipping, threesomes, giving head while in the cage, etc. and It was making me really horny for obvious reasons and I mentioned that. They said “good” and that turned me on a lot, it hurt in a good way. I said “thank you **her name” and that kind of started a theme of her talking about things she wanted and making me respond. We called it a night soon after.

The next day we were talking and I mentioned I kind of wanted to buy a new cage and asked if she wanted to help me pick it out. She said yes so we got to shopping online. We realised we need measurements so she said I could take it off to get measurements so I did and we got the measurements then put the cage back one. Once we picked one out I ordered it and she casually mentioned that because I got out that we had to start the 3 days again meaning I wasn't out until sunday but because she was camping and wouldn't be able to call that day I wasn't allowed out until monday when she got back. I asked if I could use dildos and she said no but I did it anyway a couple hours later I mentioned that I had because I felt guilty and she got angry and told me that was an extra day Moving my Release from monday to tuesday, then she found out I had used a vibrator on the cage and she moved it again to wednesday… the same day we were going to be visiting. So we planned for me to spend the night with her after my family arrangements on wednesday. Currently she won't tell me what the plan for wednesday night is and I'm going crazy thinking about it.

Will post again after Wednesday.

There was a bunch of teasing and humiliation stuff that I left out and if you want me to make another post with that stuff in it let me know.

This has been the craziest week of my sexual experience and I am crazy excited about where this will go.


Story by ChanceofAwesome