make sure she is relaxed and use lots and lots of communication, hella rouge has some very good advice as always.
I personally didn't have any pain or problems the first time and you might find that with the right preparation she won't either. Its one of those things where everyone is different, but I think that relaxation is key, and if using toys privately would help her feel more relaxed in your company than this is definately a good idea. I also think that sex is as much mental preparation and it is physical preparation so as I said communication.
You sounds like a very loving partner, and I like the fact that you are worried about her and that you are willing to take things at her pace, you obv care very much for your oh.
I agree with being slow and patient. My first time hurt like hell (honestly) and I was very sore for another day and half (no, not joking). Lube is a key, as already said. I was wet, but it was not enough, especially if you are using condoms. Well, I still prefer lube with condoms, although now much used more to penetration. But in the beginning I also used to have problems with 2 fingers. You need to go slow and relax her -nice massage works for me! And when you actually use the fingers, put some lube on and also make sure your nails are not hurting her.
Toys are another great suggestion. I first started to enjoy having something in with a small vibe really. Maybe use it for clitoral stimulation first, to get her very wet and excited.
Another thing I found out is that some position works better than others. I dont like being on my back. I found the penetration more difficult. Raised hips by eg pillow or 2 do make difference. Although the best is either me on top or on fours. So maybe experiment with that as well.
I think this is a very good first toy. It was mine. The size is reasonable and the shape is really well designed for easy penetration. She can experiment with that on which positions she prefers etc.
The first time I had sexy I was very relaxed and used loads of lube but it was still really painful! I've never managed more than one finger inside but some how a cock is just easier to work in with time and patience
It's worse these days for me so I've gotton quite used to dealing with painful penetration
Working up with smaller toys is a good idea...loads of lube is a must. Orgasming before is a good one to try and keep it regular, use a toy *slightly* outside her comfort zone regularly - I find the less often I'm "filled" the more painful it is! So spend time working up - the vagina is high in elasticity after all take time stretching.
It's vital that she is in complete control - I use jabby thumbs to control WandA's speed
Just take it slow and a little bit of pain is inevitable but it does get better with practise and she will know the difference between "agh stop" pain and "ooh careful, but carry on" pain.
Definately sounds like she isnt ready for intercourse as yet. Lots more foreplay, fingering, small toys etc and make sure she is completely ready. She may say she is but she could be v tight because shes scared/nervous still about pain and discomfort so almost fighting against anything going in which really wont help. Lots of lube too as others have suggested. Maybe try some sensual massage so shes completely chilled and then slip the massage oil lower down for a play and see how that goes x