I’ve been with my girlfriend since I was 16, we’re now both 23. She is a perfect girl-next-door figure, slim, petite, brown hair, blue eyes, gorgeous smile. I have no idea how I was so lucky.
Cuckolding for me started as what I could only describe as a weird coping mechanism for my jealousy. I was afraid of confrontation, so when I would see guys checking out and flirting with my girlfriend I would get extremely angry and jealous (which, given how feminine and beautiful she is, was all the time). Over time, I began to civilize my anger by instead fantasizing about it and getting off on the idea of her being with someone else. Eventually I managed to introduce it into our lives little by little by first asking her to start teasing me, then by some role-play / dirty talk of having a threesome, and eventually I asked if she would ever fuck another guy. At first she wouldn’t give me a straight answer, but a month or two later she asked me if I would still like the idea of watching her with another man. I immediately got hard and said yes. It was on.