How my story begins isn't all that unfamiliar and is likely shared by many men, but it is how it affects our erotic futures that make things special for some us. When I was first in college I had intended on being the best student I could be, and to finish with high marks so that I could have the building blocks needed for a great future. During the first school year I lived with my high school sweet heart; she worked a full time job in the service industry while I was enrolled in full time classes. She attended all the same parties I attended and socially met all the same people. I had a busy schedule during the week with the ever constant need to prepare papers and study, which left her with huge amounts of time to spend on her own. It started slowly with her going to friend's places in the evenings, and later going to the bars during the week while I stayed home and studied. I didn't understand at the time what I was experiencing, but once I finally found out that my sweet heart was experimenting with what turned out to be several guys and a few of them being in my department I was utterly ashamed and humiliated. My most precious belonging had been visiting people we meet together and on her own; she actually had been sleeping with guys I had classes with.
I remember moving out and spending my first nights alone. I recall hearing how she was spending all her time with a certain group of guys. It was then while lying in my bed alone that I experienced my call. That first feeling that I could not explain; I was horny with every thought of her being with those guys. I recall masturbating repeatedly thinking about her with different guys. I always felt guilt afterwards, but only for a minute because the feelings I had for her to be with another man and the humiliation I felt were like nothing I knew existed.
I lived with this memory and carried on with my life. It wasn't long before I was dating and filling in all the pieces. I was growing like most people grow in college and I became more worldly in the sense that I wasn't so boring. The one thing that remained the same was my new obsession; every girl I dated became the person in my fantasies that was going sleep with other men and somehow allow me to find out in some humiliating fashion.
This was a quiet fantasy until I met my now fiancé. I eventually found the courage to tell her how it was something that I thought about, and how I enjoyed cuckold stories and topics. She was shocked that I was one of those guys, because she had a friend that had dated and cucked another guy with the same fantasies. She claimed not to be interested in that kind of affair, and that cuckolding me was something that would make her feel bad about herself.
In truth it worked its way into our sex life slowly. It started with dirty talk while we were aroused. It then allowed her to admit that she enjoyed voyeurism; which enabled me to take pictures of her in lingerie and later naked with her discrete approval that I would show friends and strangers. It reopened the conversation of wither she could sleep with another man and if she could enjoy it, but she was still hesitant.
It was still moving slow until we had a new game we wanted to play. We both wanted to see her strip and enthrall another man with me watching. She had made the suggestion that one of her ex boyfriends liked to message her and occasionally flirt. He lived several hours away and was someone she knew so it felt comfortable. He messaged one night using msn to which she answered back telling him she just stepped out of the shower. She was actually chatting with me while I was away on a business trip. He instantly couldn't resist and jokingly tried to turn on her web cam. She asked me if this was what I wanted and I replied YES. After a short period of them being flirtatious back and forth she turned the cam on. She was dressed in her robe with a negligee I got her underneath. We were both watching her through her camera, but he had no idea that I was there.
He asked various questions that had her lifting her robe and slightly flashing him. She typed to me at one point to say he wanted to put her on video call, and that he wanted to see more. It was my last chance to stop this game, but I was lost in my unraveling erotic fantasy. I told her she was beautiful and that I loved what I seen. When agreeing to the video call she told him that it was me messaging a moment before, but that she had told me she was busy and to write back later.