I knew that my new girlfriend Amanda knew about prostate stimulation, but I was hesitant to bring up the idea of prostate massaging to her. Even though I was really turned on by the whole idea and I knew that she knew how to do it properly, it’s hard to break away from the mindset that there’s just something “weird” about it. I’m not a homophobe by any means but I was still having a hard time wrapping my head around anything going up my rear end! Turns out that Amanda has already sensed my interest in prostate massaging and my hesitation about it, so just as you might expect from a former domme, she took charge!
It was maybe our second week of dating when Amanda had me come over to her place. We had dinner and talked for awhile, then she told me to go take a shower and make sure I was thoroughly clean. Something about her tone and the look in her eye told me exactly what she meant by that. So I got cleaned up and then headed into the bedroom where she was waiting. She told me, gently, to lay down on the bed, and then she propped up my butt cheek with some pillows. Then she wasted no time and she eased a lubed up finger right into my ass and started with the prostate massaging.
I was surprised at how comfortable and pleasurable it actually felt. I thought that the first time might be a little weird, but it was just perfectly natural. She continued with the prostate massaging while also lightly stimulating my cock. The feeling was incredibly intense, yet it still took me quite a while to orgasm – and I loved every second of it. I felt like I’d discovered some super secret side of sex that had totally opened up my eyes!