My girfriend and i really want to try anal. we have tryed twice now and i just dont seem to fit. ive done a little reading on how to start. fingers are no problem and i can fit about three in her no problem but when it comes to putting my penis there it just wont fit. she has no pain through the whole thing and we use lube but for some reason i just dont fit. is there anything else i can try?
A cock ring to keep you very very hard might help. A shoestring can be used to improvise a cock ring. Have sissors handy!!
lube, fingers, then maybe some toys, and then your cock ? i guess the hardest thing is finding the right angle