Dear Mona Lisa,
Me: 37, ftm. Have been married, and was abused. Have only recently come to understand I'm ftm. Am not on testosterone and have not had surgery. I wear men's clothes, and bind my chest. I'm flexible, but mostly a top-type character. It's been over 4 years since my last sexual experience with another person in the room. I don't know if it's a phase or permanent, but lately, I've been feeling an aversion to the idea of being penetrated below the waist. I also don't want to be nude in the same room as another person just yet. Eventually, sure, but I'm just not there right now.
Him: 45, gay man. He reads the same obscure books as I; he loves my favorite obscure films; we listen to the same obscure bands. We kiss, he walks me to the subway, taking my hand, where we kiss some more before I head out. He uses the correct pronouns without fail. He's also a top. He's said in so many words that he thinks the two of us will have an important relationship, but he wants to take things slowly. When, on one occasion I tried to speed things up, he put on the brakes, gently but firmly. So, I'm pretty sure that if I were only imagining his interest, he'd make it clear to me.
So, when we finally get to the point that we're together for more than just smooching, what can we do? I've always thought I had a pretty active sexual imagination, but I fear that the shapes of our genitals and expectations we both probably have may limit our possibilities. A lot of things here are new to me, and I guess I could use a crash course in Sex Acts 101.
It seems like you and your gent have found the real fountain of youth. You both get to explore new sexual territory on a level that transcends the physical- kind of like discovering wonderful new things as a kid- like realizing Elmer's glue didn't inflict permanent damage or Barbie didn't melt in water or that a magnifying glass in the sun has an entirely different purpose. Sex is the same way- since it's best discovered through exploration, not a road map.
I'm assuming he knows that you are ftm (...you'd be surprised). I'm also assuming that if he knows this about you that he has an interest in ftm's and has already thought of a few creative ways to take your relationship to the next level. His hesitation may be rooted in the fact that a) he senses that you may not be ready and b) he's the last known gentleman on the planet. Put that man in a museum!
Use your temporary abstinence as an opportunity to develop your own sexual handbook. You can either broach the subject and have an open discussion about what you think you want and what you think he expects (and vice versa) or you can wait until the steamy moment and take things in a step-by-step how-does-that-feel-oh-no-how-about-this kind of way.
Trust me, when things heat up- especially with this person you care about- you'll find all kinds of creative things to do (think more along the lines of sensuality and not actual penetration). You may also discover that neither you or him is a top after all.
Yours in love,