I was nervous the first time my husband asked. Just make sure you are in a calm relaxed mood, start small like a finger or whatever your smallest vibrator is. Talk dirty or touch each other, the more you turn each other on first then the easier it is to relax and get into the flow of it. Dont stop Read more… talking, he needs to tell you how good it feels so you don’t get in your head and accidentally hurt him, cause stretching too fast is ***ful and ruins the mood. Overall once you do it a few times it’s really fun! Condoms, might just be us but we like lazy cleanup just incase things come down even after pre cleaning. If your harness comes with a vibrator pocket, use it. Makes it feel great for both of you!