Dear Sex Advice,   

   I've been with my boyfriend for two years.  I'm in my early 20's and he's in his late 40's.  Yes, I know, big age difference.  So who cares?  My concern is that since the day we first had sex until today, he loses his hard on inside me.  When we start our sex play he gets hard, that part works fine.  But he can't maintain it.  Well, I should say that, sometimes he can, but when he wants to cum he has to pull it out (of my mouth/ass/pussy) and jack off.  And when he does I can tell he's kinda semi you know?  There have been maybe 4 times total that he has been able to finish in me.  I really don't think it's age because he isn't the oldest guy I've been with.  I've heard a lot about cock rings and he is really REALLY open to sex toys, but how come he's never purchased one himself?  We have never really talked about his maintaining problem but I know we both are aware of it, I mean HELLO!  But since it's the one thing we've never really talked about I'd feel weird just showing up with a cock ring for him.  Either way, I will stay with him, sex is great, fantastic even.  He's one crazy dude, but there are days when my self esteem isn't soaring that I still feel like if only I was hotter, or if I was only doing something that felt better, maybe he could cum in me.  Do you have any words of wisdom?

 Hanging Out with Mr. 50/50 Bar, Van Nuys, CA 

Hello Mrs. 50/50 Bar,

     Great question, it's not you.  Let me just say that over and over.  There are a number of reasons he could be going limp, you know, all the medical stuff...smoking, alcohol, diabetes, vascular problems.  So on and so forth.  But I think if you wanted medical help you would have just googled impotence.  It's hard to get someone to go to a doctor if they can't even talk to you about their problem.  I feel for you, it's kind of uncomfortable.  But being that he is with a woman who says, "who cares, I love him anyway" is great.  And how luck he is to be with a 20-something!  So you are here for a reason.  You want a homemade, sexy cure for your man's noodle.  He sounds like a fun and kinky guy, so I would tell him something to the effect of "you would look really sexy in one of those cock rings with all the studs and spikes on it..."  Or if that is too far fetched you could say, "Baby let's try one of those cock rings that has a clit stimulator on it and see how many times I can cum!"  Or maybe the next time you guys are in a sex shop together just pick out a plain old metal one and tell him you think his cock and balls would look sexy in one.  That they are manly and they turn you on.  Those will definitely help because you said he can definitely GET hard, just not STAY hard.  Cock rings trap the blood inside the penis once it's already there.  Make sure you get the right size too, a ring that is too small won't let any of the blood that it has trapped in, back out.  And although a hard on for hours on end sounds like fun initally, it will definitely end in an embarrassing trip to the emergency room.  At some point a trip to the doctor will come up, give it time, until then there are a plethora of erection aids to try.  It will give you guys all kinds of excuses to make new toy purchases.  Have fun and keep me posted!  Hope this helped.