Reflecting on a long term affair I managed
I (m28) was in a long distance relationship years ago and it wasn’t working. I was about 22 or 23. I met an another girl online on one of those nasty websites (you know the kind) and she was around 20. She had just broken off something long term and vented to me about it. Tense stuff.
I was honest about my bad relationship and told her I wanted someone to make me feel important. She was traveling when we started chatting and when she came home finally, I lied and told her I broke it off with my gf. I’m not sure why I lied when she was already open to being my side girl.
We hooked up casually but ended up seeing each other more often. We became FWBs and I managed a real relationship and maintained her as my side chick for about a year or longer. She would go on dates and stuff and I didn’t really care because she would call me to pick her up from the dates and we’d hook up.
I still visited my gf who was long distance, it was pretty sweet to go home to my sexy gf. Her boobs were massive and she was beautiful, but kinda vanilla. She didn’t care much for me emotionally which is why I cheated in the first place. So I have vanilla when I traveled to see her and rocky road when I was home.
I later found out my side girl never broke it off with her “ex” either. One time he called her when she was over and she was like whispering on the phone to him and I told her she would get caught like that. We both never did anal until we met each other and she became addicted. Many of my most pleasurable moments in life were with her. She was crazy and wanted to explore CNC. One night on my birthday, she rode me reverse cowgirl anal into midnight and screamed happy birthday daddy. She is one of two girls who ever called me daddy and it was really interesting to experience that consistently.
She would call me when she was out with friends to pick her up. She would let me face fuck her, handcuff her, slap her around. She awakened so much lust in me.
Eventually I got caught and ended both relationships.
Not exactly encouraging this type of thing, but it was a wild ride and I wanted to share. I have some other stories to if people want to hear.
Posted Dec 3, 2025, 1:30 AM UTC