My Husband surprised me the other day by starting by stroking my buttocks and he moved to rubbing and then kissing and sucking of the anal area. I was very surprised as it was something we both discussed previously as being pretty gross and stomach turning. I really, really enjoyed it. He moved to using fingers and it seemed pretty tight. By the end I was gagging for him to enter me but we just couldn't get it in no matter what. He was well lubed up with saliva and it was definitely slidy enough but it kept either slipping into my vagina or slipping off and my anus just seems too tight for it to go in. We tried pushing but it wouldn't budge. We tried since then in a couple of positions, me on top and him below and from behind etc but no luck. I don't want to rush entry because I'm enjoying having discovered something new that makes me feel naughty again but do eventually want to go all the way but it seems impossible. Any advice appreciated.
First try more lube, saliva is not good enough for the first time, not any time really. You must be completely relaxed, have him start out by using his fingers on you, make sure his nails are clipped short and are not sharp, relax your anus muscle, when his finger is in you push back and out, do this for a while and your muscle should relax and stay a little open, try doggie for the first time he enters you with his dick, and while he goes in you try to push out. That's the best I can do I'm a guy so all I know is what I have learned from what chicks have told me. Peace