The following story is true. The named have been changed for privacy reasons. The documenting of my cuckold experiences is part of a training assignment required of me at http://mystressworld.com/IP.asp.

Unlike other cuckolds, my first experience being cuckolded was not a deep dark desire or fantasy.

My name is Trent and the woman I had my first cuckold experience with is named Sarah. We met through an online dating service. She is 32 with a girl-next-door look and what I describe as a very sexy body. She is 5’6” and 150lbs with average size breasts and a large round butt that shakes seductively when she walks. I’m 42, 6’0” 190lbs with an athletic build I’ve maintained since playing college football.

 They say opposites attract and this was definitely the case for Sarah and me. She is very confident, spoiled, bossy, and loves being the center of attention! I’m the opposite…a bit insecure, especially around attractive women, shy, and have always preferred a woman to tell me what she wants so I don’t have to figure it out myself. I am also very chivalrous and believe if you treat a woman like a Queen, then she in turn will treat you like a King.

Our relationship seemed to move fast. After the 4^th date, Sarah told me she considered us as boyfriend/girlfriend and wanted to make sure I was on the same page as her commitment-wise. I was a bit surprised, but I was also happy and told her “yes”. My surprise was due to the fact that although we had fooled around we had still not had sex, though I think she was probably ready. Part of my insecurity with women has always been my penis size (It’s barely 5” and thin).  Due to my fear of rejections I always try and prolong being intimate so the woman I’m dating has feelings for me by the time we have sex. That way if she is disappointed in my size, it won’t be as big (no pun intended) a factor.

My strategy worked well with Sarah. After a month of dating we finally went to bed together. I was so nervous that I had trouble getting hard and then when I finally did, I prematurely ejaculated in less than 5 minutes. I thought she was going to be mad, but she just laughed and said we could try again later.  But she didn’t break up with me.

As the months went on, we became even closer. We had a “date night” ever other weekend and we had sex 4-5 times a week. Although our sex life dramatically improved since our first night together, I still feared she was not being adequately satisfied in the bedroom. The only way she could achieve an orgasm is when I performed oral sex on her. I’m actually quite good at eating pussy and many nights I could make her cum more than once. Then, whenever she had enough oral, she would have me fuck her and then even if it only lasted a few minutes, she had already been satisfied and we would both go to sleep.

Although she hadn’t complained, it bothered me that I could spoil her in so many other ways, but not by fucking her, therefore I came up with a plan.  I knew that aside from having a little dick, I often came too soon. So one night while she was waiting in bed, I excused myself to the bathroom where I secretly masturbated so I would be able to last much longer during sex. Then after eating her pussy to one orgasm, I built her up to a second orgasm and then stopped short and begged her to allow me to fuck her. Although she was clearly annoyed at my stopping before she had her second orgasm, she conceded and I got on top of her. As soon as I began pumping her, I knew I would last much longer and my confidence began to build. She normally liked it nice and slow in the beginning and then after several minutes, if I could last that long, she liked to get it hard and fast. So, I fucked her nice and slow and after 5 minutes, I was still going strong!  I decided to whisper in her ear if she wanted me to pick up the pace, but she didn’t respond to me as she was concentrating on an impending orgasm. Her eyes were closed and her breathing was now even louder. To get a response from her, and with my confidence building, I decided to tease her into begging me to fuck her harder! I slowed my pace down and then took my cock completely out of her, waiting for her to beg me to put it back in. When she didn’t respond, I suddenly realized to my horror that her deep breathing was because she had fallen asleep while I was fucking her! My great plan had turned into a new low, not to mention a severe blow to my self-esteem! Completely humiliated I carefully rolled off her and went to sleep. The next morning she hadn’t said anything and although I’m sure she would’ve apologized if I told her what happened, I thought it best to not say anything at all. Needless to say, we went back to our old pattern of me orally pleasing her until she was fully satisfied.

It was after six months that our relationship changed significantly…

TO BE CONTINUED

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