First things first, I’m 29 and male, but I’ve been in the lifestyle for a little over 10 years.
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It first started when I was a freshman in college. I’d figured I’d be into it because I always liked when other guys would flirt with my girlfriends or call them pretty or hot to my face. I didn’t lose my virginity until I was 18, though, and didn’t think about trying it out with my hometown friends so I waited until college.
My girlfriend at the time was a total smokeshow. I’m talking C-cup perky tits and a good ass. She and I had taken each other’s virginity, and after that we were insatiably horny. I went to college, but she stayed back home for a gap year and would visit and stay overnight when she could.
My roommate in the dorms was an asshole. I hated his guts, but I tried to be as diplomatic as possible with him since we were stuck together for the year. My girlfriend was super charismatic and got on well with anyone, but even she struggled to like him sometimes.
One weekend, she’s visiting and my roommate (I’ll call him Tony) is being the absolute worst. He’s being a rude and argumentative asshole. Come to find out, his girlfriend had just dumped him after cheating on him for months. He was miserable and lashing out to make everyone else miserable, too.
So my girlfriend has an idea: she’ll fuck him. We had been talking about trying out the cucking thing for a few weeks and he was attractive enough so why not? She and I laid down some ground rules and I told her she could stop it if at any point she wasn’t as into it as she thought she might be. Then it was game time.
I hopped in the shower after getting back from a class, leaving her and Tony alone. He had been working on a paper and she was watching TV. To this day, I don’t know what she said or how she said it to initiate it, but when I got out of the shower and threw some boxers on, I could hear a bad creaking. I opened the door to the dorm room and saw her bent over the foot of his bed with Tony behind her, hands gripping at her hips and his pants down at his ankles.
Here is where she really hammed it up, moaning really loud and begging him to be harder. Tony had seen me and started saying things like “Look at him. You know my cock is better, don’t you?” and she would whine out an “uh-huh” or a “yes, baby.” That’s how I found out I liked the humiliation aspect of cucking, too.
He pulled out after another minute or two and sprayed his cum all over her back. I remember vividly the way her face looked. I stood there for a moment and watched as Tony pulled his pants up. There was an awkwardness to him as he grabbed his backpack and then left the room.
I asked if she wanted to shower and she said yes, but she needed me to fuck her first. After we finished, I turned the shower on again so she could clean herself off. Tony sent me a text saying thanks and I asked if he felt better— to which he agreed he did.
But that wouldn’t be the last time.