I absolutely agree with RC...LUBE, LUBE, and MORE LUBE with PLENTY of arousal and relaxation prep...I like my dildos and men THICK so I gradually worked up to 2.25 using dildos of varying widths. I first started with a 1.5 inch, then when I got comfortable, used a 1.75 inch, then a 2 inch..I am working on a 2.25 inch now....my goal is 3 inches. I may NEVER reach that and that is OK. Because my 3 incher has CUM in handy for other uses during play...so play away sugar!!! :D OR if having to buy different sized dildos is a financial challenge then use your (or your partner's) inserted fingers with the dildo during play..one finger at a time to help you gently stretch.That has worked pretty well for me too!