No matter how docile your sissy is, he’ll be extremely hurt to see you with another man and very reluctant himself to submit to being squired about by a male admirer. You need to patiently explain that if he is to be in your life, he must understand your needs. And the only way to understand what you need is for him to share the experience.
Tip: Double dating takes the edge off and turns a scary situation into a fun one. Show him how fun it is for two girlfriends to prepare for their dates together. Talk freely about teasing the boys and how he can do it to!