Solo Play vs Pegging?

I'm not sure of the size or type of dildo you used and like many other things in this world of anal play but everyone is different it what they like and what works for them. I know I hate hearing that also. I wish there was a toy that could be just referenced as the best and just work on everyone.
I do not have a lot of play with pegging I have only been pegged 3 times. My girlfriend is kinda of the same as yours. She was all excited by the thought but when it came to it. She was nervous and scared she also wont ask me for her to do it I have to ask her. I can say the first time felt really good. She really didnt wear the strapon she just used the dildo in her hand. It was the first time it was awkward the feeling what I shit. What if I fart or make a noise down there. I'm sure she had the same thoughts. The second time was not to long ago and I made her wear the strapon this time. But boy oh boy wow. I was almost instantly in bliss the whole time. We went from her trying to be gentle to me thrusting and pulling her into me harder and harder. We have a 6.5" all American vibrating whopper. It's cheap, nice but very hard feeling. It actually started to hurt a little and be very uncomfortable. So I bought a realistic 7" dual density dildo. Wow this thing is amazing is a little bigger than the other one we have but feels way smaller. It's so soft and gentle feeling. We didnt really get a chance to test it out all the way. I get pretty loud when she pegs me. As soon as the fourth stroke of her I was off and running. I got real loud fast. So we haven't had the time to. I would say to keep trying it. Try a dual density one.

Sorry I can honeskry say that if our next try goes like the others but feels better this will become a regular thing for us. If I only knew how good this was I would have done this long ago. Forget what people thing. They dont know what they are missing.

my wife has pegged me a few times and to be honest it wasn't as exciting as I thought it might be. my wife was a bit apprehensive but willing to give it a go. My thoughts are that the idea of pegging isn't just sticking something up your ass but being dominated at the same time. I think that is why wearing a strap might be better than just using a dildo. My wife wasn't really into that part of it so maybe that has something to do with it. Could also be the dildo we used. I think it was too small and rigid
I find solo play with an aneros to be far better. I didn't have any orgasm from being pegged and didn't feel like I was even close. when I orgasm via the aneros it generally starts small and builds up and up. I don't get that "wham...where the hell did that come from" feeling

I lean more toward pegging than solo when it comes to anal play. We have used various hand held items for anal play but never a strap on. I would go for her wearing a strap-on because the anal play in that capacity frees up her hands to so much more! Not a dominance/submissive thing for me. It is practically a way for multiple stimulation as is a vibrating cock ring. Unfortunately or not.....wifey is not overly interested in a strap-on but she does still get into perineum/anal stimulation for my benefit. And, she is super turned on by how she can turn me on. But, if I got to choose.....I would choose pegging for the above reasons.