MonkeyToes

THANKS SO MUCH HOWARD! Good advice that I will apply (no pun intended;) )

So, after my brief 29 years here on this planet I finally found a man that I feel TOTALLY comfortable with and can tap into my sexual curiosities with & I gave into 'anal-play'. Quite unexpectedly...I really LIKED it. I enjoyed the feeling of being dominated and I wanted to play, too. Well, my boyfriend and I got to talking and after I assured him that his interest in said activities did not mean that he was secretly gay or that it made him less of a man, he agreed to letting me reciprocate. We shared several days of teasing and erotic e-mails/fantasy scenes getting him to the point where in the heat of a moment together, he begged me to use my fingers and plug on him. He had to stop me because it hurt....Long story short...we've tried a few times now and he can't seem to make himself relax AND, much to my surprise, stimulating his prostate (no matter how softly I do it and no matter how much lube I use)seems to hurt him more than anything. He expresses the fact that he really WANTS to like it and get pleasure from it...but he doesn't know why it's not mindblowing like everything we read says it should be. My concern is that since he's experiencing PAIN, he might have problems with his prostate? He's 35, and seems healthy in ever other way...so does anyone have any input or advice? Thanks in advance!