My first toy was a small chance unflared. I had never had anything up my butt except two fingers and a silicone turner handle, so I figured I should start out small. Well, it was WAY to small lol (I got the large flared next and took it fine), so I know how you feel. Don't forget though that, if you are a guy, you can still stimulate your prostate pretty well with a small, especially with the flare. Just be patient and give yourself time to slowly massage. When I got my first toys I was going way too fast and felt like it wasn't right for me. I know better now : )