It’s has always been interesting to me how people become part of the cuckold lifestyle. Some people discover it through porn, others discover it after being cheated on, and then some just want to share their partner. Here is how I learned about these desires.
In high school I started dating Ashley who was a grade younger than me. Ashley played volleyball and had one of the biggest asses at the school. My friends made comments and I would always catch guys taking a look when she would walk by. She was really smart and as a second year she was already getting scholarships to attend university. I was in my third year and although I played sports and had mediocre grades I hadn’t figured out where I would go to university yet. Ashley and I had a great two years together I lost my virginity to her, we went to parties, prom, and snuck out during the week to see each other. We were young and horny and always looking for a place to have sex.
Once I graduated high school I decided it was best for me to go to a local college for my first year or two and stay home. I thought that this would give me time to save money, and hopefully be able to transfer with Ashley when she went off to college. Although I think it was still a good decision it didn’t work out like that. We grew apart being at separate schools – I wasn’t going to high school parties anymore, and eventually Ashley broke up with me. Of course I was sad. I didn’t have much going for me and Ashley was my longest relationship up to that point in my life.
About a month after our breakup I was hanging out with my best friend who had a younger brother in Ashley’s grade. His brother broke the news to me that his friend Jay was going on a date with Ashley. It crushed me how fast Ashley could and would just move on. At the same time it was humiliating because I knew Jay. He wasn’t my friend but we would hang around the same places together. Jay wrestled and played football for the high school. He is tall dark and handsome and got a lot of girls. He’s black and fit the BBC stereotype fit him. Occasionally, when we would all crash at the same place Jay would wake up in his boxers. His bulge was massive I’m not sure if my hard dick would even compare to his soft. This all humiliated me so badly not only did I know the guy my ex was going out with but I knew who he was and that he was sexually superior and experienced than me. I’d have to call my friend to see if Jay was going to be around before we met up.
I messaged Ashley and asked her if what I heard was true. Ashley confirmed it was. I made it clear I wasn’t over her yet but that didn’t seem to move the needle. At one point I needed to just swallow the pill and try to not think about it. Ashley and Jay were beginning to see each other more frequently and posting pictures on social media. A few months later Ashley deleted those pictures and I had heard they had broke up. I texted Ashley and mentioned I wanted to meet up with her. Ashley ended up coming over and telling me she caught Jay messaging other girls and she wasn’t going to put up with that. She told me she loved how I treated her like she was the only one and we ended up having make up sex.
I assumed Ashley and Jay had fucked because I didn’t think Jay was the type just to keep seeing her without it. Ashley had been my one and only to this point. After years of having sex with each other it felt like her pussy had molded perfectly for my dick. Now it felt different. Her once tight pussy now felt loosely wrapped around my dick. As I pumped away in missionary I asked Ashley “Did you miss my dick?” Ashley moaned “Mhmm.” But I could tell she wasn’t sincere. I slowed my pace down and we began to kiss then I asked Nicole a question I already knew “Was Jay bigger than me?” Ash tried not to answer directly but then I asked again as I picked up the pace. Ashley grabbed the back of my neck and looked at me sincerely “Promise you won’t get mad?” I told her I never could be mad at her. Then she answered “Yes he was.” I didn’t say anything else I tried with all my might to fuck her as hard as I ever had but with a few more “power” strokes I came all over her stomach.
Ashley and I never got fully back together before she went off to university where I assume she had her fair amount of fun. A few years later Jay and I became more friendly. Memories of Ashley would come up on his phone and he’d share them and we’d joke around about being Eskimo bros. But from that day on I knew I was into the sharing/ cuck lifestyle.
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