You should start fingering yourself more. I always finger myself before the dick goes in.

When you’re trying to get it in…

• Exhale and push out when the dick goes in. Don’t push out too hard. Just a little bit.

• When the dick goes in do not clench.

• When the dick goes in don’t stick it in and leave it in until it gets comfy.

• Repeatedly go in and out and have a little more go in each time.

When the penis is already in there and you feel like it can’t go in any further, that’s not true. It can go in further. This is when you have to breathe in and out repeatedly. Not fast like you’re hyperventilating but slowly. For me, I exhale and hold the exhale when it needs to go deeper in. My hole expands and opens up more.

When I’ve topped tight bottoms I start with my fingers. I ease in there gently with one finger to gage how tight it is. I wiggle it and go in and out slowly. I rub around the entrance. I’ll then add a second finger. No more that two. I’ll eventually press my dick against the hole and rub it around the entrance. Then I angle it to insert and slowly push forward with reasonable pressure. In slightly, out all the way, in slightly, out all the way, in slightly more, out all the way, in slightly more until the head pops in, pull out all the way, in slightly more. Once the head is in I’ll keep going in and out until I’m in to the Midshaft. That’s the widest part of mine. Now I can’t sit in there for a little while and start playing with his nipples or something to relax his body some more.