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Confessions of a Cheating Girlfriend: The Initial Response

A preview to my upcoming series, 'Confessions of a Cheating Girlfriend.' Enjoy!

In a previous posting, I explained cuckoldry/cheating and how I make it work in my relationship.

I consider this entry to be a preview of what's to come, as I have a new series in the works titled "Confessions of a Cheating Girlfriend" in which I will explore and detail my sexual encounters and partners in chronological order.


I can distinctly recall the concerns that crossed my mind when my boyfriend, Alex, asked me to sleep with another man.

I was afraid of losing him, and I had trouble believing he would really be okay after sharing me with another man. I was afraid of what might get out and how it would affect my reputation. I was very insecure with my body at that point in my life, so it was agonizing to imagine undressing for someone new. I was afraid of judgement and ridicule. So many fears and "what if" situations ran through my mind.

Although, it was undeniably appealing to have the chance to explore my wildest fantasies and come home to a loving, healthy relationship. This temptation is what ultimately led me to take the dive into cuckoldry.

He always allows me full control of the situation by only asking to be informed when I play with someone.

I choose the man.

I choose the location.

I choose when I meet with the lucky guy.

He sits back and watches his girlfriend flirt her way into another man’s bed, and he enjoys every moment of it.

After four wonderful years together, I’ve gained an unbelievable amount of confidence and experience in the bedroom which I use to please my partner and playmates.

However, in the beginning, I was a nervous wreck about meeting with someone new for casual sex. It didn’t help that I was going to be recording and photographing what happened between the two of us.

I remember contemplating on who would be the right choice to pop my cuck-cherry, and I was sure Alex wouldn’t be comfortable with the idea that I had come up with.

How could he accept that his sweet girlfriend was craving his best friend, Ryan, in the bedroom? Would it upset him that I'd taken notice to his friends appearance and intelligence and acted on my basic human instinct to pounce on a worthy partner?

It was something I’d be forced to approach with ease so as not to jeopardize their friendship or my relationship. I wasn’t even sure that his friend would want to sleep with me, but he was someone I knew previously and had felt an attraction towards which was something I felt would ease my nerves.

If Alex really wanted this — really wanted to see me with someone other than him — it was going to be by my rules and what I desired. He had to know that I was doing this for his pleasure, yes, but also mine. Our relationship was strong and trusting, so I was sure that we could withstand this. I was even convinced that it would be fun for everyone involved if we handled everything correctly and with class.

It was shocking how easily Alex agreed to let me contact Ryan. It was even more surprising when he took it upon himself to send his buddy a text explaining the situation and asking him ever so nicely to pound his girlfriend into oblivion. When Ryan responded within minutes with an eager "Yes," it became more than obvious that he had had his eyes on me, as well.

This fantasy was soon to become a reality for both my boyfriend and myself.

Focused and aroused, I set out on my mission — to get fucked into submission by my man’s best friend. Little did I know, this would be the start to a long, kinky journey of sexual exploration and self-discovery.

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Confessions of a Cheating Girlfriend: The Initial Response
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