Chastity and orgasm denial discussion

I figured this was the ideal spot in the forum to pose my question, given that it covers both subjects. My partner likes teasing me about being locked away and not using my member anymore. However, she also really loves riding me, particularly when she can bring me to an orgasm against my will. To get there, it usually involves T&D until I’m so immersed in the headspace that I don’t want to leave it, leading me to beg for relief while staying in that state. So she’s seeking ways for me to help her reach climax before she decides to force me out of it. We’ve talked about penis sleeves/extenders as well as simply getting a strap-on. Since we aren’t big on cucking, I’m mostly looking at toys here. I’d appreciate any advice and/or experience with either method; from both men in chastity and dommes/KH alike. We’re open to both choices but are unsure about the pros/cons, comfort, feasibility, or if there’s something else we might be overlooking. Thanks, Meg