Boyfriend's Prostate Stimulation Painful...NOT Pleasurable, HELP!!!

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 does anyone have any input or advice? Thanks in advance!

Sorry to hear about the problems!

Everyone is different - just because some people enjoy anal does not mean that everyone does or should. If the penetration part is hurting then it's simple - he's too tense. He needs to spend some quality time alone with a big tub of lube, some things to slide into his ass, and no pressure of performance. Once he gets used to it and relaxes he'll be fine. There are two sphincter muscles - the outer one is voluntary, the inner one is involuntary so he cannot control it at will. Only gentle practice and a lot of patience will open him up if he's tense or has any sort of mental reservation (you said you'd persuaded him to try it too, so he may well have sub-conscious reservations!)

The prostate part: it's a sensitive thing! Never use anything that isn't designed specially or is hard and angled, or it will hurt! My advice would be to buy one of these:

Your boyfriend should also go and see his doctor for a routine prostate check up! It's a normal thing to do, does not hurt and will set your minds at ease.

Good luck!

your boyfriend is to tense. start him with a small plug and lots of lube. keep increasing plug size and let him see how long he can keep the plug in at one time.5 mins, then 10mins and so on. let him keep it in until your ready to enter him. see if that helps.

I's start with the njoy plug - the smallest size. Let him do this for himself. I like this plug for your situation becasue it is small, and you can use vaseline, which, I have to say, after a few years of experiementation is still the best lube for prolonged usage of a toy (as long as it doesn't hurt the toy)since it doesn't break down anywhere near as quickly as the water based lubes. This may be a pricey first toy, but the upside is that, if he still doesn't like it, this toy can be boiled to sanitize, and you end up with a new anal plug for yourself. You cna also check out my review for this toy if you want more infor on the toy itself.