Yes anytime especially if I am sucking her boyfriend
My wife has fucked me with a strap-on many times times and I love it. We have a vibrating one with a double end that fits inside her as well so she gets stimulated while fucking me, and it really turns me on to see her getting into it. I like to be on my back so I can see her boobs bouncing while she does it, and I wank myself off as she fucks me hard. I always experience very intense orgasms. It's one of my favourite things that we do together.
Maybe if it isn't too big, and it's well warmed and lubed. The idea of someone else shoving a cold plastic object in my ass does not appeal, isn't a particular turn-on, though I'd do it if she really wanted. Nevertheless, pegging IS a major element of my Dirty Talk contest entry: No-Dating Policy.
What I'd rather have in there is a warm, pulsing actual human cock. Now that does sound enjoyable.
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Best orgasm of my life was when the wife took control and pegged me. Plenty of lube started slow and talked loving proceeded to full slow strokes and dirty talking, then was filthy talk tell me how much I enjoyed her cock in my pussi. When I went over the top my orgasm was from the tip of my toes to the top of my head.