This is not easy to describe.
Anal feels more full, which I like, but the pleasure is not as good, and the longer it goes on, the more quickly the pleasure dies off.
Not to mention the preparation, the time, and so on.
I like Anal, but really, if I got it once for every 20 times I get vaginal I am satisfied.
DP, one in both, just amplified everything. The good and the bad.
Positions are awkward, it takes time, but the full feeling is even better, and the pleasure of both holes is even better.
If Oral is 10/10, Vaginal is 8/10, Anal is 5/10, and DP is 11/10. But DP with toys is nowhere near the same, in fact I don't like it.
My husband says Anal is so hard to get in, and then its like 1 tight ring, whereas Vaginal has stuff everywhere going on. He likes both, but prefers Vaginal. Those "everything going on" descriptions vs 1 ring, is kind of the same for me, there is just so much more being pleasured with Vaginal.
As for you receiving Anal, the real penis feels so different, and so much better than toys, I do recommend trying the real thing at least once!
I don't enjoy condoms.
I also find circumcised to be like a half-condom feel.
The way the skin slides and moves feels amazing, and all that is lost with condoms.
Also, no lube is needed. Lube reduces the pleasure so much, but need it for circumcised and condoms.
But having said that, except in very exceptional circumstances, always use a condom when playing with others. Safety is first.