My First Adventure in Cuckolding

I was speaking with a client the other night and he asked me a question that I get quite often.  The question was, “Have you ever cuckolded someone?”  Well, naturally, I have cuckolded many men.  But he specifically wanted to know about that first time.  To be honest, I didn’t know there was a word for it that long ago.  It wasn’t something I had planned to do or even discussed with my current lover.  It was just something that happened.  You see, Joe, my lover, wasn’t exactly spectacular in the lovemaking department.  But he was a nice guy and he spoiled me rotten.  I had always gravitated toward older men and Joe appealed to me on many levels.  He took me to the best restaurants and bought me the best clothes and perfume.  Being young and in college it was “cool” to have an older man fawn over me and take me places.  As I said, he was “ok” in the bedroom.  Nothing spectacular, to be honest.  In fact, what he didn’t have in penis size he made up for in money and he was very attentive.

I expressed to Joe a desire to join a very prestigious health club and of course he eagerly whipped out his credit card.  Little did he know that this would begin his cuckold journey.  I went to the health club daily and I loved it.  There were a lot of great classes, taught by excellent instructors.  One class in particular quickly became my favorite for a few reasons.  One, it moved quickly and had very hip music, which I love.  It worked me hard and I love to work hard.  But, the other reason was the instructor.  He was FINE.  I mean F-I-N-E.  He was handsome and muscular without being overbuilt.  I wasn’t the only girl that had a crush on him though so I assumed my chances were next to nothing.  Besides, I had Joe, right?  Wrong.

One night I went out with some friends from my dorm and we hit a few new clubs.  I just happened to run into the instructor from my class at the third club we went to.  I was pleasant and we chatted a little.  He even bought me a drink.  But, then, one of the girls I was out with whispered in my ear that she had heard he had a monstrous cock.  Well, that was all I needed to know and I made it my mission to bed him that night.  After all, Joe would never know.

I was successful in getting him to take me home with him that night and I just couldn’t get enough of him.  He did have an enormous cock but it was more than that.  He was a fabulous lover.  He worked me out even  more than in his classes and I was putty in his hands.  This went on for awhile.  A few months to be exact.  I had to really juggle seeing Tyrone (that was his name) and Joe.  I didn’t think there was any harm in getting from Tyrone what I wasn’t getting from Joe.

Then, it happened.  One night I was leaving a restaurant with Tyrone and we ran into Joe.  Joe was shocked, I could tell.  But, it was even more shocking to me when he called me the next day.  I thought for sure my days of having an older sugar daddy were completely over.

I went to see Joe and he told me how turned on it had made him seeing me with Tyrone.  He said all he could think of all night long was the thought of me being fucked by that big beautiful black man and he imagined that huge cock inside me.  He said he had never had such an intense orgasm masturbating as he had when he was thinking about me and Tyrone.  He asked me to tell him all the details and he was sure we had been sleeping together.  So, I did even better for poor sweet Joe since I had just left Tyrone’s bed less than an hour before showing up at Joe’s house.

I slid off my damp panties which were still slightly sticky from Tyrone’s huge load and the fantastic pounding he had given me before I left.  I handed them to Joe.  He put them to his nose and sniffed them, and he smiled.  Although it was all accidental, I had become a cuckoldress and Joe had become a cuckold.  Thus began my first cuckold relationship.  But, not my last.