you need to talk with your wife - she needs to push you and he needs to push you -- but you are ready to become her sub sissy crossdressing bimale cuckold.
I'm already my wife's submissive Sissy cuckold, and occasionally enjoy crossdressing (it's NEVER been "forced" by my wife). I had (and still have) Sissy leanings, enjoyed crossdressing, and Cuckold tendencie LONG BEFORE I met her. She's not overly dominant with me.
Her and I simply happen to enjoy my feminine/Sissy side" privately, as I'm far from submissive, and show Sissy tendencies/leanings in day-to-day life.
I have no issues with being submissive to my wife at any given time (even publicly, if appropriate), and I'd have absolutely no problem showing my submissiveness to my wife around her boyfriend either. I could also envision (fantasize about) myself being sexually submissive towards my wife's boyfriend (definitely NOT in any other way though), but unfortunately , he's totally awkward around me most of the time. They really enjoy their private time alone, and I'm happy to respect BOTH my wife's and his preference.
I know for a fact he's NOT homophobic, as he's had multiple sexual experiences with his best friend (who happens to be gay, and a really good friend of my wife's since childhood).
If he'd only realize the immense sexual pleasure he could receive from BOTH my wife and I... She already pleases him whenever he wants.
Her boyfriend is "borderline obsessed" with anal sex, even though my wife isn't into receiving anal. Me on the other hand... I've always enjoyed having my ass played with and being penetrated. He truly could have the best of both words with my wife and I if he were a little more open-minded.
Oh well. Pipe dreams.