[Suki2007]

I wouldn't worry about him feeling degraded unless you started calling him your little slut, or things along those lines. lol Just go VERY slowly, really pay attention to his physical reactions, as it can often be difficult to verbalize or talk much, especially the first time. The thrusting part does feel a bit strange at first, but the more frequently you have this sort of sex, the easier thrusting will become. Make sure you use a LOT of lube and a good quality one - never use one with desensitizing agents.

For a harness, I would recommend one that has double straps so that the toy stays in place and doesn't move around while you're thrusting. I like the look of leather, but the cloth sort conform to your body much better and can usually be washed. You also may want to get a longer and slimmer toy than you think you need, because, since you actually can't feel where your false penis is at, sometimes it will slip out when you don't know it. Also, a longer toy is easier to insert and maneuver, as well as allows for more positioning options.

For positions, doggy is always easiest, but not the most relaxing for him. You can try having him lay on his back and raise his bum with some pillows for your first time. This is usually the most relaxing position for him. Plus, he'll be able to play with his penis while you hold yourself up and figure out positioning.

During and after your session, be sure to encourage him by telling him how sexy he looks and how much you are liking it, etc. He'll feel a lot better about it and much more comfortable with it, once he knows you two are on the same page.