I should start copying and pasting my story. I'm tired of retyping it. lol.

Anyways, I am on the tight side.
When I first had sex, he got nowhere.
Now, I get nothing from vibrators and dildos. The only way I get anything from masturbation is by rubbing myself.
But my friend sent me a thin plastic vibrator after the one I was using wasn't helping my tightness any because the second attempt was a failure too. I could get it in a lot easier and it helped a little but still, he didn't have much luck getting it in. I also picked up some astroglide and it helped a little as well but not enough because the 3rd time was a failure as well.
So, I ordered myself a jelly dildo about the size of him. It wasn't as long but just shy of his girth size. I worked with it and it didn't seem to go anywhere either.
Frustrated I gave up. But after a week or so, I thought why the hell not and picked it up again and to my surprise, it went in all the way (with the lube of course).

We then go together about a month later and he had no problems going in.

Now, I owe some of the help to the astroglide. Miracle worker for me. I owe the other to working on myself.
You may not enjoy masturbation but it will help in getting you used to something bigger than a finger or a tampon being inserted in you.
Also, use some lube. It never hurts. I recommend astroglide or some kind of personal lubricant. I do not recommend jellies. They're not as slippery.
Also take in mind that if you do it more frequently, you will get used to it. I know that part of my problem was the fact that I didn't exactly get it very often. Those 4 times happened over a time span of about a year and 3 months. There was roughly 6 months between 3 of those attempts. So I suggest that if all possible, you try to do it more often than a few weeks a part. You will tighten up between the times and the longer you go, the more you go back to "normal".