My ex was the first woman I dated who I felt was out of my league. She was tall, blonde, beautiful tits and ass. We were introduced by a mutual friend and she was a novice to kinky life and took a big interest in asking me questions about it. We started out long distance because we lived in different states. One of these conversations started with a question i wasn’t prepared for:
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“Would you be mad if you saw me fuck another guy”
My mind immediately went to a threesome, as I’m sure most do, but then my mind went down a rabbit hole I’d never thought of before, cuckolding. I began to think of scenarios where I watched as this bubbly, innocent acting woman became an amazing slut for someone else, I had to stop myself to ask:
“Do you mean a threesome or cuckolding?”
I couldn’t stop myself at this point, images of her sucking and fucking while smiling that cute smile at me began to flood my brain. I was overwhelmed by the time I got the response.
“Either”
I started to think, she was on vacation at the time and she had sent me pictures of her sexy outfit she was about to go out on the town with. If I said yes was the next picture going to be of her on her knees with a big cock over her face or a picture of her on all fours looking out over a caption that read “guess who’s taking the picture”?
I never told her what i thought, i just said no i wouldn’t be mad. To my surprise she went in a completely different direction explaining that she would have trouble with the reverse happening, we joked a little bit about getting into it throughout the relationship, but nothing like that ever happened.
But I spent the entire relationship fantasizing about what I’d let her do. She told me she was saving her anal virginity for marriage and I couldn’t stop imagining a future where she would be getting a lot of anal after we were married but not from me. I even built up a fantasy in my head about having two gentleman in a threesome with her on our wedding night and that threesome lasted until past midnight so consummation had to take place the morning after because I was too busy watching.