My penis is a coward. Help me out here.

[buster]

I feel like giving up on anal sex. More than half of my experiences have left a lot to be desired because I felt like my penis was going to be crushed. Getting the head in is usually awkward because it's a test of my (low) pain tolerance.

How long should we try "stretching out" before I go in? I'd really like some tips in general.

[Ratbutt]

Well, it may not be your fault. Your partner may just be too tense for the whole thing to go down. Also, when you are entering you partner needs to consciously open up otherwise it ain't gonna happen.

Keys are:
-Relax your partner
-Lotsa lube
-Make sure they are opening up

If you have a sensitive dick, you will want to make sure that you get your head in a few inches and then you will feel comfortable. Don't leave your head in the vice grip of the anus. THe pressure on your shaft will bother you less.
G'luck

[buster]

If you have a sensitive dick, you will want to make sure that you get your head in a few inches and then you will feel comfortable.
G'luck

Thanks for the advice. Unfortunately, getting the head in is the most painful and difficult part. I get close to pushing the head further in and I hit my pain tolerance ceiling

Someone needs to invent a device that works the same way as a shoehorn for these situations.

[kalina]

Down there can be stretched wider than most people think. Yep, she was too tense and not relaxed.

[TSLoverUK999]

Widen your partner with your fingers, a dildo or any household object

[buster]

Widen your partner with your fingers, a dildo or any household object

I think I'll have to use household objects since I apparently have rough, caveman-like hands. The nail-biting definitely makes it worse.

[Jay Jay]

Well I wont call myself a master but I can suggest two things. I have a wide penis that has made a few asses nervous. Most of my partners will grab the lube but I will normally use my finger untill I feel them start to relax. Once that happens you can try to insert slowly so the anus gets a chance to adjust. U should take care of your hands. Guys get manicures if you dont want to do it yourself. Once you can insert your finger you are already in a good position. It is not as easy to feel the sensation of the anus loosining with an inanimate object.