Originally from https://samanthasummersinstitute.org/community/forced-bi-cuckolding/real-cuckold-stories/#post-368
I should have known I was a cuckold that Saturday afternoon in 1957 when I was young and I saw the love of my life, JoAnn making out with another guy in the balcony of a movie theater and all I could do was watch them with a hard on leaking precum into my jockey shorts.
I should have known I was a cuckold that night in 1959 when I called the next love of my life and Carol was home alone with the biggest cunt hound in my class. As she was hanging up the phone, I heard her say, “Stop it Eddie! Someone will be home in 15 minutes and I need to get dressed.” All I did was go into the bathroom for privacy and stroke my cock.
I should have known I was a cuckold the night in 1962 that the next love of my life, Jackie told me she was pregnant and getting married the next Monday. I went home and actually considered asking her to marry me instead of the father of her baby.
I should have known I was a cuckold that night in 1964 that I saw the next love of my life, Mary Lou secretly hand a piece of napkin with her phone number on it to my friend Roger at a bar while we were double dating with him. I took Mary Lou home and never mentioned that I saw her do it. When I got home from the date, I was in that bathroom again to relieve the blue balls I had thinking about Mary Lou and Roger. After a few more dates, she broke up with me and I never saw her again.
I should have known I was a cuckold a few months later in early 1965 when I found out that Judy, a girl I had dated a couple of times after Mary Lou was pregnant. I knew it wasn’t mine because I was a good Catholic guy and was still a virgin at age 22. Another trip to that bathroom was the order of the day.
I should have known I was a cuckold in 1967 when the real love of my life and first wife, Marilyn told me 4 months after our wedding that she had lied to me about being a virgin. I was so pissed I stormed out of our apartment and walked around town for two hours. My rage slowly subsided and I gradually realized that I wanted to hear the whole story, When I got back my bride was distraught and crying. I soothed her and made her tell me how she was debauched at age 18 by her first boyfriend Danny. As she related the story, I got a raging hard on and fucked her hard before she could finish.
I should have known I was a cuckold that night I 1976 when we were playing strip poker with Lorraine and Joel and I was the first one naked and had to leave the room. Lorraine was next and joined me in the family room where she proceeded to pass out drunk on the couch. As I sat in my recliner stroking my cock looking at the naked Lorraine and her full brown bush, nice tits and dark brown nipples, I started imagining Joel and my wife fucking in the living room. I don’t really know if I was relieved or disappointed when, after what seemed like an eternity but was actually only about 10 minutes they both came into the family room. Joel came in first naked followed by my wife who still had her bra and hip-huger panties on. Needless to say after we roused Lorraine and they left, my wife and I did not make it upstairs to the bedroom. As a matter of fact we fucked while she was still in her bra and panties. I remember wondering if she was so turned on because she had seen Joel’s 8 inch hard-on.
I should have known I was a cuckold, when, after Marilyn died in 1986, until I met Pam in 1989, my main sexual release was jacking off while fantasizing about the time an 18 year-old Marilyn was seduced by Danny and not all the glorious times that I had fucked her.
I should have known I was a cuckold in 1989 when I started dating again. Virginia, a 38 year old widow who I desperately wanted to fuck, told me that she was a submissive to her late husband’s nephew. You guessed it! I went home and rubbed one out.
I should have known I was a cuckold in 1990 when Pam told me about her last boyfriend, Jack who also happened to be her master’s thesis adviser. She told me in great detail how they were in a dom/sub relationship, and that she had been his sex slave for nearly 3 years. When she told me all this and that she was going to see him three days before our wedding because he was blackmailing her with the hardcore videos of her that he had taken during those 3 years, I went with her and turned the tables on him. I made him show me the tape. It included date stamped footage that proved that he was guilty of violating his University’s rules against a faculty member having a sexual relationship with one of his students. When we got back to her place, I couldn’t wait to play the tape again and I fucked her on the living room floor in front of the TV.
I should have known I was a cuckold during the early 90’s when we started telling each other about our past sexual adventures. I ran out of stories after about 5. Pam seemed to have an inexhaustible supply of tales. She realized that I got turned on hearing them and we both loved our Scheherazade sessions. They would always end up with us fucking. I don’t know what she was thinking about while we fucked but I was always visualizing the tale she had just related.
I should have known I was a cuckold all those nights when Pam was on business trips to DC and she did not answer her hotel room phone. She always had a flimsy excuse such as: I was out with Beth, I had a headache, I had to stay late at the office, etc. I always believed her and never suspected that she would cheat.
I began to realize that I was a cuckold one night in 1996 in Cancun. We had picked up another couple and in their drunken stupors in the wrong beds. Pam and the other woman had collapsed in the wrong beds. I watched the other guy fuck Pam in the spoon position. I didn’t fuck his wife until he finished fucking Pam. I couldn’t take my eyes off of Pam and him.
I knew I was a cuckold that night in 2003 on our 13th anniversary trip to Sandals-Negril when I was hard as a rock watching as Samuel’s foot long black cock continuously ravaged my wife’s pussy turning her into a quivering orgasm machine. By the end of that night I had not only watched him fuck her, but also held her legs open for him, fed his monster cock into her pussy, had sloppy-seconds doggie-style while she sucked him hard again and when we got back to our room ate her creampie.
Source: reddit.com/r/eroticliterature/comments/dfklzi/cuckold_litany_cuckold_list