It sounds like it is a psychological problem. I am not saying that you are crazy, but that your mind is so afraid of or averse to inserting anything that your body literally tightens/ tenses up, making wearing tampons impossible and inserting speculums painful. I think you need to learn some relaxation techniques and try to figure out what has caused such fears.
Also- I know this will sound weird- but when you masturbate, you should insert a finger into your vagina. I say this because you need to associate a pleasurable feeling with the insertion of something into your vagina. If you can get one finger in, then go to two, them maybe on to a reasonably sized sex toy until you feel ready to receive a man's penis. And use lots and lots of water- based lubricant when you do this.

I think you need help of an experienced partner who can ease the necessary mode and willingness. A lot of oral stimulation and fingering. Also a pump up toy hat is small when inserted and then enlarged slowly as you get closer to orgasm. Also try anal stimulation when receiving oral clitoral stimulation. This will associate penetration with great pleasure. Also I would make myself available to help you personally.

coolrunnings2, that was completely uncalled for. this forum is not for getting laid, and I doubt that's what this girl wants any times soon considering what she's going through

I just want to also note that I would NOT suggests anal stimulation! because it HURTS and it will NOT associate penetration with 'great pleasure'. if you think inserting something in your vagina is tight, then you are not going to like anal so don't even try. at least not yet. please

I had the same problem, although not as extreame as you. I was very tight. or in my opinion I was. I never used tampons, never went inside when masterbating, it hurt when I went to get a pap test, and it took ages for me and my boyfriend to finally have sex that could be considered full vaginal intercouse.

what I suggest is find someone you trust. honestly, if you've already waited this long to have sex, you might as well wait for someone that you KNOW you want to have sex with, that you trust completely. this was the BIGGEST factor for me. I completely trusted my boyfriend and was able to tell him when something hurt or when we had to slow down or what I needed to make sex easier. if you can't have this type of communication with your partner, you're not going to get far.

tell them that you are nervous and that you feel that you might be too tight for sex. start slow. start with letting him give you clitoral stimulation, to the point of orgasm if he can get you there. Letting someone get you to orgasm can bring you to a whole new place with that person. it can bring a new trust level between you.
after that, when you feel comfortable, try letting him get one finger in you. this will probably be easiest after orgasm when you are very wet down there. When you're comfortable with one finger, try two, then three if you feel you can handle it.
you don't have to have vaginal intercourse right away. there are lots of ways to please each other without it. so just take your time. a few nights of trying what i just discribed, and you should find that you are a lot looser, and that one finger doesn't hurt at all anymore.

you won't be tight like that forever. it just might take a little more work, a little more TLC to get you to loosen up and relax.

its worth it though, beleive me. not only is the sex great once you get to that point, but all the attention that you'll get from your partner to loosen you up before hand is awesome too.
and guys enjoy the tightness or so I've heard aha