This is a very big problem that I face. Please excuse the length of the post.

For the past 4 years, I have been unable to have fantasy-less orgasms which I used to easily get when I was young. I am now 46. My sex drive is high unless I am in severe depression. 4 years ago I reconnected (phone+letters) with a man whom I used to be in love in my twenties. I found the feelings not only alive but deeper. He is married and in another state and older than my dad, so it is a dead end, but life is hard, unpredictable, and often unfair, so I found myself attaching to him more and more, and he is attached to me, but it is not an actionable attachment. In fact he is crazy about me, as he was back then, and I have gone on to develop a very complex relationship with him, writing lots of letters and as of recently even sharing sexual fantasies, which he found flattering. I find it unfair that given the degree of our connection, it is not actionable because he is unavailable. The unfairness of this situation embittered me on top of lots of terrible things that have happened to me over the years - abuse by former husband, his alienating the children, a horrible mood disorder, periods of disability and unemployment, unstable housing, etc. My version of bipolar makes me very different from state to state, from a social butterfly with a special sparkle and allure to a person who cannot fake a smile, moves very slowly, is dreadfully anxious and depressed, and experiences a wide variety of debilitating side effects of psychiatric drugs.

Enter orgasms by masturbation. There are two problems with them - one new and the other old. The new problem, new as of 4 years ago, is that I cannot have a fantasy-less orgasm anymore, because I need to have an image of the man whom I described above in order to bring up an orgasm. I cannot help invoking his image. It does not have to be a sexual fantasy of a sexual act - in a minority of cases it is, but for the most part I just think of him.

There is another man, R., whom I knew in my twenties and we are reconnecting. Rationally, he would be good for me now - he is available, local, solid as a rock, not as old (he is 12 years older), and wants a relationship with me. I was wildly attractive many years ago and he was then just one of the suitors - one of many. I did not appreciate him back then because I was a spoiled little girl who was used to male attention and adoration, and he was on the humbler side of the range as far as my suitors went. And then I married a guy who would go on to abuse me emotionally, financially, and even physically - it was a disaster from which I still have not recovered. But all the suffering, the horrors of mental illness and side effects of medication, the risk of tardive dyskinesia that is hanging over me as I get older (I develop acute neurological side effects to psychiatric medications and had an acute dyskinesia, which predisposes me to tardive dyskinesia later in life) made me humble myself. Also I saw a lot of suffering on the floors of psychiatric hospitals, in outpatient programs, and on these boards. So I am a humble person now and from that vantage point I appreciate the gifts R. has to offer.

So I will probably reconnect with him in person soon, and I want to make it work. He would like to figure out how to give me my complex orgasms - we emailed back and forth about sex. I plan to tell him of the problem (that I have masturbated for 4 years thinking of that older man and have not had orgasms on their own, without invoking these thoughts or his image). I plan to be honest and hope to make it work. I will be kind, attentive, cuddly, vulnerable, and appreciative. What other strategies can I employ in order to orgasm with him?

My second problem with orgasms stems from the days of my youth. I would precipitate an orgasm by squeezing my muscles, instead of prolonging the pre-orgasmic pleasure. I always wanted to prolong to learn what was there - what magical sensations would lie ahead - but when I'd feel that an orgasm was possible, I would hasten to have it. This is an interesting problem and this one does not have to do with another man. So I plan to tell R. about it. This one is far more fun. I sometimes want to be tied up as to not be able to hasten to an orgasm but be forced to experience pre-orgamsic buildup to the fullest. I thought he can do it with me, for fun.

I have a lot of other men in my life who are partly unreal - far away, flirting on the phone or over Google hangouts, asking for explicit photos, confessig their love for me. One is local, but I do not want to have sex with me. I want to stop running this huge operation with multiple semi-real suitors (I knew them all in real life - they are not completely digital, but currently they are far way) and trade all that nonsense for one real man who is a solid guy, and my baggage with the feelings for the older man is in the way. Please help me solve my problem in a gracious way. Thank you for reading.