My wife (F40) and I (M43) have been together for about seventeen years, married for thirteen. I’m the only man she’s ever slept with, but I had numerous lovers before her. My endowment is quite average, and I have no trouble bringing her to orgasm during intercourse. In the past two years she’s had something of a sexual awakening, and we are experimenting in bed with toys and different roleplay scenarios. She is a natural submissive and loves it when I’m in charge.

Lately, however, I keep returning to something that she told me early on when we were dating: that she’d fooled around with a very large guy without going “all the way.” I started wondering if she might regret that decision, and (more generally) what she might be missing out on sexually by only being with me. I also wondered what she did do with that guy, even if it stopped short of intercourse.

So I bought a cocksleeve for us to try. She was apprehensive at first. The first time we tried it it hurt too much and we had to stop. The second time also hurt, but she had multiple orgasms. The third time, she had the time of her life. She came so intensely and so often that she could barely speak afterwards. She was shy about it, but I knew that it had changed something in her. I couldn’t help but wonder: was she imagining the hung guy that she passed up?

I’d love to chat with women who can provide some perspective on this. Is my wife missing out on an incredible experience by only being with an “average” man? What might she be imagining when she’s getting fucked with the sleeve? What does she want that she can’t admit to me?