I have been locked up in chastity for roughly two months now. This feels like the longest stretch of my life. I met my girlfriend a while back and when I brought up this lifestyle, she was completely fresh to it all—very vanilla. At first, she just held onto my keys to accommodate me and basically let me out whenever I asked. We talked extensively about everything, including my fantasies, but it seemed like she wasn’t that into it. I was grateful for what we had and was ready to give up on the idea of her being truly dominant and testing my limits.
Recently, though, she started “experimenting” more. She stopped letting me out when I asked. Before this change, she made it clear that whenever I pleased her, she would also please me in return as a gesture back. I didn’t get to orgasm every time, but she always teased and played with me. That has stopped too. Now I find myself licking her or watching her use her womanizer more often, so my cock doesn’t see daylight very frequently. Her daily behavior has shifted as well. She usually handled most of the housework (she only works part-time, so she is home more than I am), but now she plays her games and leaves me to do the work. Instead of asking if I could help with things, she simply tells me to do them. I am totally fine with all these changes; couldn’t be happier:-)
When I asked her during one of our recent sessions about when I would be allowed to cum, she told me it was up to me. She said I could cum as soon as I bring proof that I sucked another man’s cock. I was really dumbfounded by this and told her so, thinking she must be joking. She insisted that this is one of the fantasies I once shared with her (which is true) and wants it to become reality. I mentioned there are those fantasies you want to come true and others that are fine in your head but not necessarily otherwise. She said if this was a hard limit for me, she would unlock me, but then chastity play would be over. She explained that everything until now has been living out my fantasies while she gets herself into the mindset of being my dream-Dom. She felt like a “service-Dom” for me. Now this is her own fantasy; she really likes the thought and finds it hot, wanting me to do it for her. She told me to take my time to think about it and report back with my decision.
I am really unsure how to handle that. The idea of sucking another man’s cock genuinely scares me. On the other hand, she has a point, and since it is one of my fantasies, I might even go through with it. But how? I can’t just walk into a gay bar and ask some guys if they want their cocks sucked while I hold up an image as proof for my Mistress? I mentioned this concern to her, and she said that would be my problem alone. She does not want to get involved in the process; she just wants the proof and all the details afterwards. At least for now gulp
Any advice on how to approach this? Should I reject it and hope she continues our chastity play? Or go through with it? How do you find someone for that and keep it anonymous?