Confessions of a Cheating Girlfriend: the First Encounter/His Best Friend

When Alex asked me to sleep with someone else and record it for him, I was initially wary of the request. It took time and lots of thought to warm up to the idea, but I eventually decided to take the plunge.

I could ask an ex-boyfriend to help me out, or I could meet someone online that seemed interesting. If I found someone from work or class or the gas station down the street that caught my eye, I could have them. The possibilities were truly endless.

I had recently met his best friend, and I couldn’t deny how attractive I found him. Knowing it would be easier for me to sleep with someone I had previously met, I brought the idea up carefully with Alex.

Who could have guessed he would be all for it? I never would have thought he’d take it upon himself to send Ryan a text explaining his fetish and what we’re into sexually before asking him if he’d be interested in fucking his girlfriend.

I recall the nerves that washed over me as we waited on his response to Alex’s texts. I was never popular in school or with guys, so I couldn’t be sure he would even be interested in me as I was him.

Imagine the relief and arousal that hit me when he said he’d love to fuck me and record it.

He planned to host on a day when he wasn’t working or in class, and we exchanged a few steamy texts up until the actual day.

I made a trip to the liquor store on the day that he set up for us, and I bought some whiskey to sip on before going to his place to help ease my nerves.

Once I made the drive to his house across town and knocked on his door, my anxiety quickly dissipated as he flung open the door and welcomed me with a quick hug and a warm smile. He was so handsome, and he was so kind. We made our way to the couch in his living room and sat down to talk a bit before jumping into things. As we sipped on our drinks and chatted, I could sense the tension building in the air. I had intentionally chosen a shirt that dipped low on my chest, and he had taken immediate notice. He used one of the cheesiest pick-up lines that I’ve ever heard and slipped his arm around me to initiate things, but I was drunk and horny enough that it worked.

Deciding to take charge, I straddled his hips and ground myself into him as I ran my tongue over his and my hands through his hair. I still get aroused at just how quickly he got rock hard underneath me.

We took it to his bedroom to avoid the risk of being walked in on by one of his roommates, and things accelerated much quicker. Clothes were lost within seconds, and we were on the bed tangled in each other.

He readied the phone for taking photos and videos of what we were about to do, and I prepared myself to put on one hell of a show. He fucked me for hours in every way imaginable, and he only stopped for short breaks to catch his breath. Neither of us came, but we both tried to push the other over the edge repeatedly.

Once we were both equally satisfied and couldn’t continue anymore, we found our clothes and composed ourselves. He sent all the pictures and videos to my boyfriend, who would be at home enjoying the evidence while I was still driving home, and kissed me goodnight before walking me out.

I took my time driving home to revel in the afterglow of what I had just done. I had just fucked my boyfriend’s best friend, and I had loved it. I would do it again, and I had no regrets. I only hoped my boyfriend felt the same way once he received the pictures and videos of me pleasuring Ryan and getting nailed.

My car crept into the driveway, and I turned off the headlights. Heading towards the door, I prepared to gauge his reaction. Upon entering the house, I found him acting perfectly normal and doing nothing out of the ordinary. He informed me later that he’d quite enjoyed what he had seen and wanted it to happen again as soon as possible.

I couldn’t deny that I had had a wonderful time fulfilling his fantasy, and I wasn’t exactly up for an argument if he wanted me to make it happen again.

I still enjoy the thrill of a new fuck and never turn him down when he asks me to go out and play. I think I’d even fuck Ryan again if given the chance, but so far, I’ve only been intimate with him once. He did, however, open the doors for me that led me to explore cuckolding and become the cheating girlfriend that I am today. My boyfriend thanks him majorly for that, but that’s just what friends are for, I suppose.

Thank you, Ryan!