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Hi!
Here is my story. I hope you can help. Sorry that it's so long, I just didn't want to miss any details that may be important.
My boyfriend and I have been together for over 4 months now. I am 26, he is 31. We are in love and frequently have sex. But we have a problem: he can't come during intercourse with me. He gets good erection and can keep it for hours, but just can't come inside me. We talked openly and a lot about it because it upsets him quite a lot. At first we used condoms, so we thought that was the problem, but then I started taking the pill, we started having sex without condoms, but the problem remained. At that point I thought that he didn't feel comfortable around me yet and needed time to be able to relax with me. But weeks passed, we became closer and more open to each other, but nothing changed. I was of course upset, but I never showed it to avoid hurting him, never put any pressure on him to come and did my best to make it about the process, not the result for him (which is how I see it). I am a beautiful woman and never had any thoughts that i am not hot enough for him and that can be the reason. he gets turned on by me very fast (just kissing is often enough), he enjoys the sex with me a lot, but for him the orgasm is also very important and at times we were having sex for hours because he wanted to finally come which was a problem for me because sex stops being enjoyable for me after about 40 min.
So after a while it became clear we had a problem. When we talked about it I always told him that it would pass in time, but I began to research on the internet and use the tips i found, but without telling him I did, I made it seem spontaneous in order not to put pressure on him to come when I tried something new.
We have sex in a variety of positions, we tried quite many at the beginning and found a few we could master and found enjoyable (me on top with him lying and sitting, doggy style, missionary and its variations with my legs around his waist and on his shoulders), we enjoy them all, but none sends him over the edge. So the tip I found on the internet to try different positions wasn't helpful for us.
I used another tip - to try to fulfill his phantasies: I asked him specifically what chothes and underwear he liked on me and bought more of that kind, changed my intimate haircut to the one he wanted, started initiating sex more often and outside the bedroom (shower, kitchen) since I noticed that it gets him very excited.
I also often give him oral sex and a long foreplay, he likes it a lot, and sometimes I managed to make him come from oral sex, but always only after about 20-30 min of oral stimulation which was quite exhausting for me and often even after so long he still couldn't come. He is not my first boyfriend, so I know I am good at BJ, and I tried different techniques to determine what he likes, so I didn't know what the reason was, and it was very upsetting.
I also tried to determine if he had any psychological barriers or traumatic experiences, so I managed to find the right moment to talk with him about his and mine past sexual experiences. Before me he only had sex one time in his early 20s (so about 10 years ago) with a condom and couldn't come that time either. he used to masturbate and watch porn a lot in the past, and still does it, but not so often anymore. He also said that he comes very fast during masturbation, so i decided to try giving him handjobs, it worked and I can now always make him come with my hand and lube within minutes. He finds it much more pleasurable to come when I stimulate him now than when he does it himself which I think is a good sign, I finally feel that we may be closer to solving the problem. As I learned what kind of handjob he likes I think I understand now why he can't orgasm during sex and rarely during oral stimulation. He likes (or is simply very used to) a tight grip and fast motions of a hand. I like pleasuring him with handjobs a lot, but I still want him to be able to come during intercourse. I have a quite tight vagina and also can tighten its musles so he can feel me better and I am always very wet, so we never need lube during sex, but of course i am neither as tight nor as hard inside as a grip of my hand, and neither he nor I can move during intercourse (or during oral stimulation) as fast as a hand can. So that's probably what the problem is. I hope you can give me some helpful advice how to solve it.

Many thanks in advance
Holly

Answer
I recommend that he work at learning to masturbate with less force.  A toy called the Super Head Honcho might help.  It is available online, including drugstore.com and amazon.com.  Masturbating with the Super Head Honcho and a water-based lube can get your boyfriend used to a gentle feeling of the kind he would get from a vagina.  In order for this masturbatory retraining to work, your boyfriend needs to completely give up his high-pressure masturbation.

It is not enough for you to want him to change his masturbation; he has to want it.

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