naughtyingu wrote:
I find it rare/hard to cum when im with someone :( Ive never cum in a pussy, [...] Im really not very sensitive, it can and often does fade into numbness. Im about as sensitive as the inside of a forearm just above the elbow.
I can cum from wanking, [...] the mechanics of how i wank, vs sex is quite different, [...] i can hold it tighter than any pussy or ass ive experienced, [...] ive tried not wanking for a week or so before meeting someone, i honestly dont know how much that helped
Dan Savage often talks about the "death grip syndrome", which is the situation where a man can orgasm from masturbating but has difficulties orgasming any other way because of having become accustomed to a tightness of grip which can be matched by nothing else.
Dan Savage's advice for this is to retrain your penis by limiting all of your sexual activity to the kind you want to orgasm from. So for you that may mean no masturbation whatsoever and only having sex with your partner. Your penis will become so desperate for stimulation and you become so desperate to orgasm that your penis will accept whatever stimulation it can get. Your penis will increase in sensitivity until you can orgasm from that other stimulation.
This does require some discipline on your part because it sounds like you will need to do this for longer than a week, since you tried that and you found that wasn't long enough. It can take some time (the exact time varies between individuals), but the rewards are that you will have a much more sensitive penis and you will be able to enjoy a much more varied set of sensations.
I hope that helped.