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With my ex-we had several 3 somes with the idea of it being his first bi experperience but he never quite felt ready for his first steps-I was never able to work out if that was because he was very submissive and wanted me to "force" him into action.
However when we had split up, I agreed to facilitate a meet with a guy from a swingers site who did turn out to be his first male sexual partner. I was very clear that I was not playing and he totally respected my boundaries with that. My ex liked to dress and I helped him to put on his pvc dress, stockings and thigh length boots and he was masked and cuffed lying on my bed when the guy arrived. I initially stayed downstairs while the business began but curiosity got the better of me and I really wanted to see if he would actually go through with it this time. It was hot to see and help him-I held him open while he took his first cock.
And I really gained the benefit because the guy who came to fuck him is now my long term partner and I couldn't be happier