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This might be a bit lengthy, but I’ve been wanting to share this story for ages. Hope you like it and thanks for any feedback! It all started back in 2016. My best friend (who is my mistress now) and I had an on-again, off-again friends-with-benefits relationship over the previous few years. One day, I told her I wanted her to take charge of the sexual side of things. She seemed vaguely interested but agreed to consider it.

As we looked deeper into it, we discovered chastity. It seemed like a cool idea for me to try out, and she liked the prospect of seeing my cock locked in a cage. Since I didn’t know much about chastity at all, my first purchase was metal, and it turned out to be way too big (3-inch cage; I’m wearing a 1.5-inch one now). It was discouraging, but luckily my birthday was only a few weeks away, so she surprised me with a smaller plastic device. That worked better, though still not perfect. I wasn’t totally fond of it, and after the second failure, we mostly abandoned the idea.

Unfortunately, we drifted apart for a while. She got a boyfriend, and I went back to an ex. My relationship with my ex was completely vanilla, yet I constantly craved returning to what my best friend and I had shared. Sometime in 2017, she broke up with her boyfriend, and we tried actually dating each other properly. That didn’t work out either; she ended up dating a friend of mine instead. Not knowing what else to do, I started questioning many things.

She has always been the one person I can trust with anything. One of the biggest questions was my sexuality. We had experimented with strap-on play in the past and enjoyed it greatly. So, while still partly in denial, I began watching trans porn. Eventually, I gave in to my inner thoughts and went on a gay porn kick. I loved it—loved everything about it. One night, I told her, “I think I might be gay.” She was very accepting but advised me to do some serious thinking because she sensed I was confused and wanted to make sure I was doing the right thing.

Still not ready to fully accept it, I stopped altogether. But that only made me more miserable and confused. By halfway through 2018, I reached out again, mentioning I wanted to go back to what we had, but this time do it correctly. After some research, I settled on the 1.5-inch device I’m wearing today.

We tried it again for a while—some days here, weekends there, etc. We worked up to a week straight, and I could tell something was shifting. She wasn’t quite herself; my constant talking about it was taking a toll on her relationship with her boyfriend. We drifted apart once more, which broke me somewhat. Eventually, we made up but agreed to pause our friends-with-benefits arrangement for the time being. By early 2019, I was self-locking during this period, though something still felt off. So, I decided to stop completely and do some serious soul-searching.

She encouraged me to put myself out there and try new things. Even then, I was denying that trying the other team might be the right path for me. One weekend, while away from town for a bachelor party, something just clicked in my brain. I thought, “Screw it; might as well give it a go.” I downloaded Grindr, met this really cool guy, and ended up giving him a blow job. That one experience was all it took to hook me completely. It became the highlight of my weekend. I told her the next day, and she was ecstatic. I had finally broken through that wall of doubt in my mind and accepted that I am bisexual. I’m still only out to her so far, but I’m proud that I can confidently say it.

At this point, we were working hard on our friendship, and I asked if she was ready to take control of me again because I really needed it now. She agreed under one condition: I couldn’t make chastity the only topic of conversation. She would hold my key, and while it’s known between us, it isn’t always said aloud. I think our friendship is stronger than it’s been in a long time right now. We started with a month locked up and have moved into our second one this month. She still allows me to look for other girls and will unlock me if, for some crazy reason, I find someone I want to fool around with. But honestly, it’s easier just to stay locked, suck dick, and get fucked. I think she likes it better that way too; after all, she is a master with the strap-on. She also loves the thought of having another man’s cock inside me. Now, I’m just waiting for her to let me join in more!;)