- Posts
- 1
- Joined
- Jan 1970
So my boyfriend and I just started experimenting with longer-term chastity, and while I was obviously fine, I didn’t want him getting overwhelmed. He was very good, so after a week, I decided to take him out. We do this to enhance both sides of the relationship, so we usually discuss punishments, rewards, and everything in between. His reward offered 3 choices: supervised masturbation, me pegging him, or allowing him to penetrate me once I felt ready. Lastly, there was the option of me only pegging him but with doubled orgasms; if certain tasks aren’t completed within a set time, no orgasm either way, followed immediately by milking after play ends. After a thorough discussion and reassurance, he settled on the second option. Everything went amazing until it came time to let him out. Instead of being excited as I expected, he tried to convince me to do other things instead. I finally confronted him about whether or not he actually wanted vaginal sex at that moment and accused him of lying slightly. His response was that he didn’t think he deserved it. Have any other key holders experienced this? Is this behavior rewardable since he was so devoted, punishable because he technically wasn’t honest, or should I be concerned for his mental well-being? I love seeing him devote himself to my pleasure but not at the expense of his self-worth.