After several sessions involving rectal and prostate massage, I asked 'Serena' — one of my two instructors in erotic massage — whether she would peg me.
During our sessions, Serena had masturbated me in many different ways, including (a) having me on my back, knees to chest, while she held my cock and massaged my prostate, to climax; and (b) having me on my hands and knees, and stroking my cock with her left hand, as the fingers of her oiled right hand slid in and out of my rectum.
The first time Serena (unexpectedly) performed (b) on me, it gave me one of the hottest, most intense orgasms I've ever had. (I remember my rectum spasming on her fingers, still inside me, while sending jets of hot cum all over her massage table. I don't think I'd ever had a rectal orgasm before, but that had just happened at the same time I came from my cock.)
Trying to let my breathing slow after all that, and still on my hands and knees, I heard myself say, "That's like being male and female at the same time." She patted me on my ass and said, "It is, isn't it?"
Which started me fantasizing...
One afternoon, after a prostate massage, and as Serena was wiping down my chest and abdomen with hot wet towels, I asked her, "If I buy a strap-on and bring it, will you fuck me?"
It wasn't just the thought of feeling her plundering me from behind, that was so arousing... I loved to imagine her, naked except for the strap-on, thrusting away, and was planning on asking her to let me make a video, if she said yes. (I'd seen every inch of Serena, of course, many times, but never with her hips thrusting.)
Serena paused in her scrubbing, and looked thoughtful. "No... I'm going to have to draw the line, there. Too close to breaking my promise to my husband." (She'd told me, early on, "No intercourse." But I was hoping that that applied only to my keeping *my* cock out of *her.*)
Serena did recommend a particular brand of vibrating prostate massager, and told me that if I wanted to, I could bring it to our sessions. She would masturbate me while it was inside me.
I did end up buying that massager — and I loved the very intense climaxes it produced — but I never brought it to my sessions with Serena. If she wasn't going to fuck me, I still preferred her fingers inside me, to the toy.
Being pegged by her remains a favorite fantasy, to this day.