A
female
age
41-50,
anonymous
writes:My boyfriend hasn't been able to bring me to orgasm through any method. Not oral, not sex, not fingering, Nothing. So the other day we were having sex, and trying to get me to have an orgasm. And even though we know that if you focus everything on me having an orgasm it will never happen, it's just hard to help. I was extremely close to having an orgasm and then i just lost it. So we tried changing positions but when we tried to go at it again he wasn't hard enough anymore. He just lost his boner. And we couldn't get it back. You have no idea how many problems this brought up for the both of us. I started feeling insecure like maybe he wasn't attracted to me or i wasn't good enough to keep him hard. And he felt like a disgrace or something a.) for not being able to make me orgasm and b.)for not being able to perform at all. I think that maybe he lost it from the incredible disappointment from thinking this would be the time I could orgasm and it not happening. I just feel lost. I'm almost scared to keep disappointing him even though he says i'm not. I need help.
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Fancy yourself as an agony aunt? Add your answer to this question! A
male
reader, uncle Frank  +, writes (12 July 2009):
 dear female 26-29,
I won't ask you embarrassing questions you may not wish to answer. You are at just about your best age to enjoy sex and that includes climaxing also.
Perhaps you concentrate too much into: "I must com! I must cum!" instead of: "Whoa! How nice it is! How much pleasure you give me, darling! How hard you are! How long you are! How thick you are!" and all the other appreciative things you could say to him. Maybe you do, I don't know.
When I was young I was not interested in girls even though I could appreciate the beauty of their bodies. I started to masturbate when I was about 12 out of curiosity to see if it was true what a chap about 20 told a bunch of 10 year old or so, including myself, that if we pump our dick long enough some white liquid squirts out of it. He was doing that to himself and we were all rather disgusted by it.
I walked out of the forest without seeing the end of the performance. That was in 1944. In 1946 I remembered the incident and became curious to see if it was true and while in the bathroom I tried and after a while it did.
Afterward I felt guilty and sinful: mom and dad always told me not to do dirty things or sinful things and I was the convinced that what I did was what they had meant.
Within a few weeks I was addicted to self gratification: as soon as I realized that it gave me pleasure it became all that I wanted to do. Every time I had the chance of being unobserved I pulled my wire and greatly enjoyed it.
The first time I had sex was with a gypsy girl in France. Her sister had been fiddling with her crotch for some time in my view as we both sat under some trees in a woods, even as her sister was trying to stop her and to take her hands away. The sight got me so aroused that I eventually approached them and gave older sister a hand and eventually took over the action and ... "How warm it is!" I remember thinking and - because she had asked me not to make her pregnant - I pulled out just in time!
I was surprised at how quick it had been and in my ignorance I was getting annoyed with the girl who had by then started to kiss me, whilst before she seemed actually trying not to do anything with me. I supposed it was because of the sister sitting five meters away watching us.
Only some ten or twenty years later did it occur to me that she might have been virgin too, like I was before meeting her.
I gather some experience and learned a few tricks by the time I got married, at 34, but I never knew what really to do till when I reached 53 years of age and God healed me of cancer in one of my 'vas deferens' - the tube that carries the sperms from the 'testis' to the receptacle near the prostate gland. God also taught me how to make love to a woman during that month through the Scriptures and though visions and dreams. Until that time I was only able to 'perform' with my younger wife twice in a day or night and that only twice a month. The day I felt the healing power of God through my groin I became instantly aroused. God's voice said: "Touch your penis." As I did I came, with the capital C.
As I was going through several books on 'Erotica' and 'how to make love' I masturbate and orgasmed four more times that day! Since then i was able to perform my marital duties to my wife up to three or four times a week and Several time during the week-end.
I am 75 and masturbate regularly at least once a week.
I no longer have a wife to have sex with and I have noticed that if I do not masturbate (to ejaculation that is) at least once a week I eventually struggle to urinate. But immediately after an ejaculation I could pass water easily and at an increased volume.
Even though I could only perform seldom, I had learned to 'hold back' till my young wife had orgasmed at least ten to fifteen times before letting myself go and enjoy my orgasm as she came another two or three times.
I suggest that you and your man (boy friend isn't a term I like in sex)do something you are obviously not doing at the moment. My book 'Do not rape me, darling' is not yet been published so I cannot suggest you read it.
In it I teach young men, and older husbands, not to 'rape' their loving women. Most time the man initiate sex by just 'grabbing' his woman and proceed to penetrate her without proper stimulation. He does not arouse her to the point of orgasm, before penetrating her. If the man did that the woman would enjoy the intercourse with a very high intensity of pleasure and her orgasms would explode one after the other in pleasant succession, for her. Not only, but that would make the intercourse so much more enjoyable for him too that soon he will be arousing her every time he wants to have sex with her.
I suggest that you print my answer to you and let your man read it by 'accidentally' leaving it where he can see it.
What also you can do when the time for sex arrives is this:
play with him as you get each other undressed and make sure that you start to play with his thing till he orgasms and ejaculates all over the place or in you hand or in a towel.
Keep playing with his penis as it becomes soft and tell him the you are going to get a warm and wet facecloth to clean him before doing just that. Clean his penis well and keep touching it and possibly kiss it and suck it.
If he tried getting you as soon as he came in, offer him the drink he likes and bring it to him if he is in the bedroom. Keep touching him both his penis and his face and hands and, depending on the weather temperature, whatever else is available to your hands and lips.
By the time half an hour is gone by his penis will again start to harden and by this time you should be sufficiently aroused to take it inside you. If necessary put a lot of your saliva on his prick or some olive oil or whatever you use for lubricant. You should be naked at this stage of the game and you should be touching your clitoris with moistened fingers and also be fingering your fanny internally so to get yourself aroused too.
Suck his penis if it is not hard sufficiently before dripping saliva or oil on it. As soon as he is hard and you are aroused and WET inside - obviously he has to be naked and on the bed - straddle him and kneel squatting on his erection, making sure it goes all the way inside you without hurting you.
Now you can: put your hands on his shoulders and move your body up and down on him or/and sit straight on him and move your pelvis and abdomen forward and backward as if he were an horse and you were riding him.
If leaning forward, make sure your clitoris is in touch with his body and rub it sideways and forward against his pubic bone every time you go down on him.
If you are sitting straight you can put you hands behind you head or neck and as you move your pelvis to and fro make sure his penis rubs, actually bumps, your 'G' spot in the front area of your vagina. You can also keep your hands over your vagina and rub you clitoris as you keep up your to and fro movements.
Your orgasm should not be long on cumming, now: just keep going enjoying what you are feeling. He should not ejaculate for some 15 minutes still, and even if he 'comes' before you: keep going because the second ejaculation usually leaves the penis hard for a while
Let us know what happens in your next letter to Dear Cupid.
uncle Frank
A
female
reader, Jess1ca_1988 +, writes (7 July 2009):
well i like to play with toys while having sex, llike a bullet if you know what that is, they r pretty cheap and they work wonders!!! so when your having sex try getting on your hands and knees and get the toy out and place it on your clit and play with it that way u get yours and he gets his and it keeps him felling like "hes the man" lol
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A
female
reader, anonymous, writes (7 July 2009): As another post mentioned, you have to be able to do it on your own first. Make sure you can! Then, show him how you like it. Maybe bring yourself there in front of him first so he can watch your technique. Then next time, guide him with your hands until he gets the hang of it. Also, have you thought about using a vibrator together? My boyfriend uses one on me because it's the only way I can orgasm and we both love it.
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A
reader, anonymous, writes (7 July 2009): You didn't mention whether you can bring yourself to orgasm. Do you masterbate?
For quite a few years, in my early days of sexual experiences, I didn't know what it was to have an orgasm...until I began "pleasing myself." That changed everything.
You are both focusing on the destination way to much! I have learned to love the Journey as much as the destination and now there is no poblem reaching a climax.
Relax and enjoy yourself as well as your man!
Sex is supposed to be enjoyable...not stressful!
Britt
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