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Masturbation Mentality Problems

MattyMoonTonight

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This has been on my mind for a while, and even though I'm sure this same topic has been asked perhaps a thousand times since this forum went up, I wanted to ask it directly.

Masturbation has taken on a more functional than a pleasurable activity for me. It's not so much fun as it is a sleeping aid. But the crux of the dilemma is that when I include anal stretching, I don't exactly feel anything. There's no pleasure in it, just pressure, no matter what I use, and no matter if I go straight for the prostate. Using a toy feels like trying to achieve a goal, just stretching, really, and not enjoying it. I can recall only once several years ago that I managed an orgasm from only anal contact, but it never happened again. I know it's a mentality thing, at least I'm hoping that's all it is.

I'm concerned because the implication that I'm unable to achieve some kind of stimulation from anal contact would make me a pretty poor partner for any guy in the future. You can say sex isn't everything, and I would agree when in a public discussion, but people are people. Is there some kind of exercise or thought problem I have to consider to make the next time actually enjoyable and not feel like I'm only trying to entertain the idea that I'm avoiding feeling like a gay imposter?
 
This has been on my mind for a while, and even though I'm sure this same topic has been asked perhaps a thousand times since this forum went up, I wanted to ask it directly.

Masturbation has taken on a more functional than a pleasurable activity for me. It's not so much fun as it is a sleeping aid. But the crux of the dilemma is that when I include anal stretching, I don't exactly feel anything. There's no pleasure in it, just pressure, no matter what I use, and no matter if I go straight for the prostate. Using a toy feels like trying to achieve a goal, just stretching, really, and not enjoying it. I can recall only once several years ago that I managed an orgasm from only anal contact, but it never happened again. I know it's a mentality thing, at least I'm hoping that's all it is.

I'm concerned because the implication that I'm unable to achieve some kind of stimulation from anal contact would make me a pretty poor partner for any guy in the future. You can say sex isn't everything, and I would agree when in a public discussion, but people are people. Is there some kind of exercise or thought problem I have to consider to make the next time actually enjoyable and not feel like I'm only trying to entertain the idea that I'm avoiding feeling like a gay imposter?
As I see it, there are a few different things to answer here.

Masturbation to aid sleep is okay and should not be a problem, so long as it's not affecting you in a negative way. If you do it to get to sleep, and you're not feeling bad about it, then it's not a problem if it serves a purpose for you. You might want to consider what's preventing you from sleeping normally and take a look at the root causes.

Anal stretching: achieving an orgasm from anal play can be difficult, even a holy grail for many of us. Direct prostate stimulation can feel awkward or underwhelming when you do it to yourself as part of the thrill is the surprise element that you get from a partner, whether they're using toys, fingers or their cock. If you're doing it with the aim of giving yourself an orgasm, you might be putting too much pressure on yourself and you're ending up disappointed. For many of us who enjoy anal play and being fucked, the pleasure is in the pressure and stretching, and the psychological enjoyment of feeling another man's cock in your ass. An anal orgasm is great if you have one, but if you go into anal play with the aim of having one, you can end up feeling let down. Personally, I rarely play with toys except to prepare for sex, they don't do much for me, but I love to be fucked for the reasons I describe below.

Implications for a future partner: sex with a partner has all kinds of other factors that you don't get when you're doing it to yourself. It's about feeling him with your body, the stimulation he gives to your cock if you fuck or get sucked, and the feelings of pressure and pleasure inside you if you receive him. Being fucked is pleasurable for all kinds of reasons that for me and many of us are all about submission, giving pleasure, and feeling the intense feelings, and a sense of joy and achievement of doing an amazing thing together. You'll be giving him pleasure with your body and making him cum because you're willing and able to give it to him, and that's an amazing feeling. As a bottom, you don't always cum from anal stimulation and you can and should cum from penis stimulation in whatever way works for both of you. There's more to being a good partner than the stimulation you get from it. It's all about sharing and enjoying the experience.
 
As I see it, there are a few different things to answer here.

Masturbation to aid sleep is okay and should not be a problem, so long as it's not affecting you in a negative way. If you do it to get to sleep, and you're not feeling bad about it, then it's not a problem if it serves a purpose for you. You might want to consider what's preventing you from sleeping normally and take a look at the root causes.

Anal stretching: achieving an orgasm from anal play can be difficult, even a holy grail for many of us. Direct prostate stimulation can feel awkward or underwhelming when you do it to yourself as part of the thrill is the surprise element that you get from a partner, whether they're using toys, fingers or their cock. If you're doing it with the aim of giving yourself an orgasm, you might be putting too much pressure on yourself and you're ending up disappointed. For many of us who enjoy anal play and being fucked, the pleasure is in the pressure and stretching, and the psychological enjoyment of feeling another man's cock in your ass. An anal orgasm is great if you have one, but if you go into anal play with the aim of having one, you can end up feeling let down. Personally, I rarely play with toys except to prepare for sex, they don't do much for me, but I love to be fucked for the reasons I describe below.

Implications for a future partner: sex with a partner has all kinds of other factors that you don't get when you're doing it to yourself. It's about feeling him with your body, the stimulation he gives to your cock if you fuck or get sucked, and the feelings of pressure and pleasure inside you if you receive him. Being fucked is pleasurable for all kinds of reasons that for me and many of us are all about submission, giving pleasure, and feeling the intense feelings, and a sense of joy and achievement of doing an amazing thing together. You'll be giving him pleasure with your body and making him cum because you're willing and able to give it to him, and that's an amazing feeling. As a bottom, you don't always cum from anal stimulation and you can and should cum from penis stimulation in whatever way works for both of you. There's more to being a good partner than the stimulation you get from it. It's all about sharing and enjoying the experience.
Thank you for saying that. I should have clarified that I don't use masturbation as a tool for sleep all the time. Antihistamines seem to be the only things that works now. I know it's not at all healthy but I've been an on-and-off insomniac for most of my life, and my life is a bit busy at the moment that forcing the sleep is what works.

Thank you for providing the perspective I'd been misinterpreting. Maybe it's a mixture of jealousy seeing it happen to others and feeling inadequate, or just inherently incorrect. A let-down is pretty much how I feel it is for me whenever I have the opportunity to try. Now I feel stupid for acquiring such a collection of toys to try and feel something out of them. Money spent is money lost.
 
...I'm concerned because the implication that I'm unable to achieve some kind of stimulation from anal contact would make me a pretty poor partner for any guy in the future. You can say sex isn't everything, and I would agree when in a public discussion, but people are people. Is there some kind of exercise or thought problem I have to consider to make the next time actually enjoyable and not feel like I'm only trying to entertain the idea that I'm avoiding feeling like a gay imposter?

When you take skydiving lessons, they show you, while you are still on the ground, how to jump, how to land, how to prepare your parachute, etc. They even show you a video about what it looks like when you skydive.

None of those things are remotely the same as the feeling of jumping out of a plane, feeling the air rushing by you and floating free in the air.

Masturbation and using toys are not the same experience as real sex. There are times when they are better but they are never the same experience. Real sex involves a large variety of senses and sensation. Until you actually have sex with a real person, you will not know what the real experience will be like.
 
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