My Wife Dated The Same Guy All Through Out HS And Most Of College Until She Finally Broke Up With Him.

My wife dated the same guy all through out HS and most of college until she finally broke up with him. I met her about 6 months after they had broken up. We hit it off immediately and ended up getting married about a year later. As a result she had only ever dated 2 guys in her whole life. About 4 years into our marriage I started fantasizing about my wife being with other men and this soon my number one fantasy. I told my wife about my fantasies and she thought it was weird, but was ok with it because it was just a fantasy.

One evening we had gotten a babysitter so we could enjoy a night out together and we were reminiscing about our respective HS and college years. My wife commented that she really regretted that she had dated the same guy for so long and wish she had instead just dated a number of other guys. I told her that if she wanted to date other men that she still could. She thought I was joking but when she realized that I was completely serious she asked me how I imagined that could happen and who she might date. She didn't cuckold me until years later, but that night was one of the first times we talked about it as being a possibility rather than as pure fantasy.