WooVictor first time anal
What you could try is more lube and opening the her anal highway with a dildo/vibrator.Or lube and your finger, if it's not a working girl and a gf, open with your tongue.
That always works, if it's a working girl used a dental dam or kitchen plastic wrap. Using your tongue to open her up that way. Once the way is paved your hard dick will follow.
PS. A little tiny touch of viagra/25mg will help in keep the little man hard.
The first part of the second quarter of this year
WooVictor
Do a search on: my name, also lazaro, boxcc and meatman. This question posted by me was very well answered by these masters. If I recall correctly it was in the first part of the second quarter of this year.
Best of luck with this. By the way, Worf1972 is on the mark. I would take the route with fingers and toys to help open the gap. Lube is ultra important.
You might also want to consider using a topical analgesic which will help to reduce the pain in your last chica. Understand that the pain will not go completely but will be reduced.
Regards, Havanaman