Yes, he will experience pleasure! Possibly more so because you'll be so tight. You'll probably feel like you don't want to or even can't make any movements such as grinding your hips the first few times, because it will feel weird and uncomfortable, and possibly painful, but it'll start to feel more natural and comfortable once you've done it a few times. Make sure you're really aroused and wet (and most of all, comfortable and fully ready!) and have him use lube. Yes you can do it several times in one session, you may be a little sore and have an odd kind of sensation the next day (a kind of aching/phantom feeling of something inside you) but it'll quickly pass.