My first cuckold experience was more or less an accident. It happened about a year and a half ago. My good friend who lives several thousands of miles away came down for the week. Because I didn't have much free time to spend with my gf Amber, towards the end of the week I was feeling a little backed up. We knew we couldn't sneak off and do it so I brought up the idea of a threesome with her because I had secretly always wanted to try it. I was a little surprised at how fast she agreed to it :)
It actually ended up being one of the most embarrassing moments of my life. She ended up sucking his dick in front of me which was fine. When it became my turn, I couldn't get hard. I guess I was just nervous or something. She tried to suck on it for a few minutes and I felt humiliated in front of her and my friend. I should point out at this time that my friend is black and his dick was probably around 8 inches long. Mine is 5 inches hard and about 3 flaccid. So with my 3 inch dick useless compared to his 8 inches...it was embarrassing.
For days after that I was emotionally crushed. The funny part though was that whenever I masturbated, my mind went back to that moment and for some reason it got me off. The thought of my girlfriend doing another guy was emotionally jarring yet physically stimulating.
So fast forward to about a month ago. Here's the condensed version of what happened. Amber broke up with me (at this point we'd been going out for three years) for another guy. I practically begged her to give me another chance. After a few days she decided to. I found out though, that she had given this guy two blowjobs and that he was a little more well endowed than I was. I don't know exactly how big, but I assume it's bigger because Amber gave me an ultimatum. She would stay with me if I was willing to let her be free to fuck around. She basically told me that since I was the only guy she had been with, she thought I was big. She excused the first instance by thinking that every black guy was bigger, and that for white guys, I was still above average. After her fling with the new guy though, she found out. She realized she needed an emotional support (the other guy turned out to be a jerk) but wanted a bigger dick for her.
Which of course, leads me to where I am now. I will use this blog to deal with the jealousy as well as the excitement that will no doubt occur over the next few months.