Seduction and teasing.
Why is this portion at the end rather than the beginning? Because by now you know what you can and can't do, what turns her on and what turns her off. Sex is an integral and wonderful part of most relationships, and if you're like me, you'll find opportunities to do hot little things to arouse her.
Write a very explicit note on a little piece of paper and tell her to put it in her bra and keep it there all day long. Believe me, because she can feel that note against her boob, she will be thinking about it (and your intentions) constantly for hours.
Or, maybe you're at a party. Maybe you're on a hike. Or in a dark movie theater. There are ways to tease her in such locations.
Perhaps you're in a big box home store looking in the lighting aisle. Get face to face with her, drape your arms over her shoulders and pull her close. Kiss her lightly on the neck then kiss her tenderly on the lips.
Should the others in the lighting aisle wander out of sight, run your fingers over her breasts and fondle them through the fabric. Lightly tweak her nipples. Run one hand down to her crotch and stroke to stimulate for a moment, regardless of what sort of genitals she has. See if you can get her to moan and her knees to buckle. Kiss her again and fondle her ass.
Then playfully swat that ass and say (as though it's her fault), "Come on, quit distracting me. We gotta choose a fucking floor lamp."
She might attack you when you get back to the car (keep an eye out for mall security). Or maybe she will wait until you get home and the garage door closes before attacking you. These are the sorts of attacks that men enjoy.
What to take on a hot date.
3. Your STD/HIV test results document, if any.
5. An adventuresome spirit.
You can put most of that in a small "shaving kit." Put the adventuresome spirit between your ears.
A certain TS lady friend wrote me: "Anal sex is my favorite.... When a man is in me...I can't get enough. Feeling his taut penis stretch me, then throbbing with a glowing wet orgasm is like a gourmet meal. It makes me feel so warm, cared for, and safe."
It's a good idea for the lady to hit the bathroom first and also douche, to assure that the lower colon is empty and clean.
Use a quality lubricant. Make sure the head and shaft are well lubricated. Even if you're using a lubricated condom, add more lube to the outside surface.
Begin fucking slowly then increase the tempo as appropriate.
An uncircumcised ("uncut") cock is a potential advantage in unprotected anal sex. A good part of the back-and-forth movement will occur within the sheath, not against her opening, thus reducing wear and tear.
Have fun and good luck!