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When I get into natural position my cock is like below my chin and at a weird angle, because my cock naturally points towards my stomach when erect. But if I push my cock forward slightly or wear underwear/something that makes it stay more forwards, then it meets my mouth at a better angle and I can go much deeper. Does anybody else have to do that?

I also feel like when I go for my max depth, I'm coming at my cock from the front angle too much. So my mouth will be further down the back-side of my cock but not as far down the front-side of my cock, which gives the illusion of how deep I actually went.

To go beyond my cock head/ridge to the shaft would require my bottom lift to pass the corona, but I feel like that requires me to curve my back in a different way than I'm used to. Feels like I might need to reset position and start training for flexibility from a better angle?

My top lip passes the frenelum but my bottom lip passing the corona/ridge seems further away.

Any tips!

It's been a while since I've been able to get my cock to my lips when erect but when I could, I noticed that I wouldn't be able to get the correct angle to go into my mouth. I am still about an inch away from getting my penis past my teeth but when I do get there I hope this isn't going to be a big problem.

I've always found it easier to get my cock toward my mouth when I'm soft because I can bend/stretch it in whatever direction I want. My penis is more sensitive when erect but I am sure when I get to the point where I can truly suck it, it should feel good either way.

no, you are not alone there...i have seen a few videos of guys using a rolled up towel between their cock & abdomen to help get the angle right, and i remember one of the members here talking about using some sort of hose or rope to pull his cock away from his stomach. i've done similarly by pulling my cock out of the leg of my shorts sometimes. i also remember at times when i wasn't making contact as well it seemed like sometimes i did better by 'aiming' my mouth more towards my bellybutton than towards my cock.

Look up some neck flexibility/strengthening exercises... but be careful... necks are not very forgiving... take em slow.

Nice. I got the idea of using my unused underwears which are tighter/smaller for everyday use. Thus they will support my cock's angle and I can put my hand below my thighs with more comfort. I have been using small caps and playdoh boxes to elevate my cock from legs to my mouth closer. But I hope tight underwear trick will do better.