My problem recently. Had a "pleasant surprise" with a first time lover...We tried & tried...then I found my tube of numbing cream. (A squirt internally solved the pain)...Thicker lube (inside and outside) solved the tight fit...
So we continued & finished...more than several times!!! Entry was so much easier from behind, rather than face to face. We even thought I squirted for the first time ever...till the next AM....
Picture this: a virgin's wedding night from "A Nightmare on Elm Street"!!! We had to use peroxide & laundry pre-spotter, so we could leave the "crime scene" without worrying about having to wear REAL cuffs & cumming up with realtime bail money!!!