Maybe working the sun sweating my head off (taking breaks here on MS) has really screw'd me up, but....
guess I'm just not sure where my head should be with all this.
fwiw, who says your head SHOULD be anywhere? (I don't know that the voice that says "wrong" is necessarily your own voice). Obviously you're consciously aware of the dynamics, imo, enough to say if it's not working for you, even in the midst of it, if it's not. Perhaps even look at it similarly to the way you'd respond if someone wanted to bareback. You also mentioned he respects you. I like that point. Embarrassing? Nah.
See how you feel. Have a good time.
You may or may not notice your feelings in the actual situation may have changed since the last time.