My girlfriend orgasms from it, multiple times in fact. The angle of which my cock hits puts pressure on the deep spot of her vagina even though I'm in her anally. Use lots of lube and make sure to have the guy take his time so you can relax. As soon as you tense up is when it will become painful.
I would definitely use a toy first and see how you do. Bonus part to that is if you like anal, you can use the toy to have double penetration when you eventually have a cock in you. My gf LOVES that! I've never heard her moan harder than when she's getting some DP.
Repeat this in your head: lube, take it slow, relax. As long as all three are accomplished, you should be fine.