Dear Ass Play,
I think it's pretty rare that your best sex is with your best girlfriend. This is where the term "hate fuck" comes from. This is also why pornography exists. Some people claim the best sex they've had is with their current partner. And if that's true, then awesome! But more often, the people we want to spend our time with don't necessarily deliver in every single area, including sex. It's like dating Michael Jordan and expecting him to be as good at baking cakes as he is at dunking basketballs.
Sex and love are related and intertwined, but they're also very different and separate phenomena. That's why you can have a genuine love for your sister, but not want to have sexual intercourse with her. Similarly, you can have a fantastic physical experience with someone you don't like very much as a person, and wonder "Why do I love fucking this person when they're so annoying?"
For some reason, difficult and complicated people often provide passionate and thrilling sexual experiences. It seems that, for them, the sexual experience is often a way to escape the anguish of an otherwise stressful life -- it's a massive release. I've had a lot of friends who have remained in toxic relationships because the sex was good, yet they complained constantly about how irritating their partner was. It's hard to argue with that logic to an extent, because orgasms are great. But at some point, your heart and soul want more.
I think everyone has an "ultimate" sexual experience with another person, or even themselves. That experience is so intense and overwhelming you kind of end up reckoning with it for the rest of your life. You compare it with every other experience that comes after, and with every person you interact with. And as you compare those experiences, you realize it's unrealistic to expect your experiences to "measure up" to previous ones -- it's also unnecessary and tiring.
Be glad you had any experiences at all. Be glad you had great sex at all. Be glad you can remember it. Be glad you can store it in the Rolodex of your mind and refer to it, especially in moments of self pleasure. Be glad you're not dead. Be glad you can be glad.
In addition, remember that time and your brain can exaggerate your memory. Thinking back to your earlier life can add an incredible sheen of excitement and unattainable quality to the experiences you had before. If you were suddenly having sex with the "ass play" girl again, it might fall short of what you remembered. Or it might even be better than the sex you had before.
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The point is, there will always be a higher high, a sexier sex, a fancier fancy, etc... Despite the fact that sexuality is a fundamental aspect of our very being, it is also a sensational experience that should be treated with respect, doubt, and humor.
You'll never be able to have "the best sex you ever had," because you can always imagine a few more adjustments and modifications that would make it even better. And next thing you know, you're spending all your time and effort trying to achieve the best sex ever. It's a noble effort, but do you really want to spend your time doing this?
You have to ask yourself, is having the most mindblowing sex that anyone's ever had important to you? Or is it just another distraction amidst the crushing intensity of being alive in general? Talk to your girlfriend about playing with your ass, but also cherish what experiences you've already had with her and others. Use whatever mental images you have for moments of self-pleasure. Cherish your life and all that you've experienced. Keep on moving forward and keep on accumulating life-material. Don't just to fuel your orgasm -- fuel you. And have some fun!
Your friend, Andrew W.K.