My First Time Cuckolding – From Fantasy to Reality

My First Time Cuckolding – From Fantasy to Reality

First time cuckolding, everyone always remembers their first time trying something new. First time masturbating, first time sex, first time trying oral, first time anal… And first time playing a game of sexy strip chess, right?

One experience that really stands out for me was my first time cuckolding. This was years ago. I had fantasized about it for a while but had never met anyone who wanted to follow through. Until I dated a guy who, let’s just say, lacked a little bit of oomph down there. I didn’t want to hurt his feelings, but let’s just say my lack of satisfaction soon turned me into a real bitch.

So I hinted I wished to experience first time cuckolding. Low and behold, he was very turned on by the idea!

Something that surprised me about cuckolding was how easy it was to set up. We joined a website for swingers, searched a variety of profiles, and made a short list of potential ‘bulls’. Okay, I say a ‘short list’, but given what we were looking for, I ought to call it a ‘BIG list’. Yes, you guessed it, my boyfriend wanted to see me take a really big dick.

It was our first time cuckolding, but we were not going to be accepting half measures. We met at his place. We had drinks first and then discussed our limits. I was attracted to him immediately.  It didn’t hurt that he was handsome, muscular and I could see a bulge in his jeans that made my eyes pop. When I decided that I was ready for more than just talk.

I got our first time cuckolding started with a simple kiss. It escalated quickly.

It blew my mind that my boyfriend was so excited to see me on my knees, easing that massive dick out of our new friend’s jeans. We had only just met him and here I was, sucking a dick that had to be more than ten inches long. He was hard in seconds, I was dripping wet and I could see my boyfriend was in paradise.

In the bedroom, he showed me that he knew what to do with all of his body, not just his dick. He stroked me, groped me, kissed me, and licked me until I was literally begging him to put that monster cock inside me. It may have been my first time cuckolding, but it was not my first time going wild with pleasure. What really made it different was having my boyfriend watching that huge dick pounding mercilessly into my eager pussy. It wasn’t just so long, it was so thick that it was stretching me like my boyfriend just couldn’t.

He took me in every position you can imagine and I came in every one of them.

I lay on my back and screamed his name, I rode him until my eyes rolled back and I got on my hands and knees to take it doggy-style while I laughed at my boyfriend jerking off his dick in a corner. I did allow him to fully join into my first time cuckolding experience at the end, though. He deserved to be rewarded after all.

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