[Advice] Trouble During "Alone Time" (nsfw)

Apologies if this isn't the best place to ask. It seemed like a reasonable choice. So as any guy does, once in a while I feel the need to get off prior to going to bed. Usually, I would use a couple fingers, which didn't really do anything for me aside from get me horny. I then had to resort to the one thing I had around the house, which was a slightly larger plastic cylinder. Now, this was a bit better, however it is really hard plastic, and didn't feel so great. The window of opportunity opened not two weeks ago that allowed me to buy and sneak a dildo into the house. I was excited to be able to push aside that terrible plastic thing, and had time to try it. Well, it didn't turn out so great. While getting it in is fine, I can't use it for long before the pain becomes too much to get pleasure from. I've tried it a few times since, and same result.Since one bad experience tends to turn one's mind off from the idea of doing that action again, I'm starting to worry. I want to be able to handle it and get pleasure from it, and am turned on by the idea, but when I try to do anything, I can't manage to make it work.In the short of it, I want to know if anyone has had this kind of problem, or if anyone might have suggestions as to what I can do to help. Maybe I'm doing something wrong or jumping "ahead of the game"? I'm not sure.