I think that's the first barrier when you first start. You need to kind of bend it and get it into position while it's still soft, then you can get a bit harder. I'm still working on it too, but I haven't had much time to practice.
I think about this often.. I’m 40 yr old man. I’ve never been with another man but have been fantasizing a lot about it for quite a long time. I have a skinny body type with a nice little firm ass! I’ve tried to do this but find it really difficult but that doesn’t stop me from fucking myself! I like to make myself feel as sexy as I can… I shave my entire body and put on some nice tight lace booty shorts. I like to inhale poppers as the make me so horny! I sometimes like to straddle a pillow and grind the fuck out of it! Sometimes I’ll live my tight little hole and ride a vibrating anal plug! If I could get my cock into myself ass I would never leave the house!
EVERY GUY LIKES TO FUCK HIMSELF PARTICULARLY WHILE HE HIS MASTURBATING. I love to fuck myself in front of a mirror that shows my hole body from toes to my head. I love to shove veggies like carrot, cucumber from thin to thick one in my ass, and sit on a chair to watch how cucumber or carrot are going in , and, when they stuck in my ass I start stroking my cock and touch all my body, If I have a panties from some one like my family,I sniff and brush it on my face. I enjoy watching my curle body in the mirror while grab my cock and pull down my ball. I do not rush to cum soon and it takes time at least 30 or 40 minutes to cum.
I have been able to do this. I usually need a little lube to get my cock head into my asshole. Too much lube and it will slide out. With a little practice, I was able to get the head and some shaft into my asshole. I would hold it in and rock on it and have even cum in my own asshole.
How big is your cock, and how far is your ass from your cock based? these are so important physical situation to engage cock in a ass hole.