Biggest regret of my life was ...
Channel: Radio Stories
Date: 02/12/2022

Biggest regret of my life was ...

M 24. As a kid I'd always watch cheating wife/ gf porn and it really turned me on. I had this fantasy of catching my future gf or wife with another man in bed. Later on I came to know about this thing called cuckolding. Then in 2019 I met my girlfriend ( F 20 then). She was a decent, studious kinda girl. She was definitely smarter than me. I wouldn't say she was a 10 but she had a cute face, wore specs and had an amazing body. She had her kinks but it was not as crazy as mine. One day while making love i brought this cuckolding topic up to her to see what would be her reaction. She laughed it off the first time but after I repeatedly tried bringing this up she scolded me and told me she'll stop talking to me. So I didn't bother her again.

This year during the month of February she told me that there's a guy in her university who really likes her and wanted to take her out on valentine's. This guy was a really good looking. I stalked him on Instagram (cause I was feeling insecure) and found out he was a 6 feet tall powerlifter but told me she didn't like him at all and that he was very arrogant (she was lying). I teased her about all of it,calling her by his name and stuff not knowing how into him she already was.   

Then on March one day she suddenly brought up this topic of cuckolding and do I still think about it. At that time, out of sheer excitement, I didn't think it through and told her I still fantasise about her having hardcore passionate sex with another man( preferably better looking or hung than me). She to my surprise said she might fulfill my fantasy. I was feeling happy but at the same time scared because thinking about this is something and it actually happening in real life is something else. She asked me who i thought would be the perfect guy for the job and I took that guys name from her university as a joke. She said yes without any hesitation and at that time I just laughed and teased her even further. I challenged her if she had the guts to go ahead and fuck him. 

Three days later, Wednesday, she told she's been talking to him the last couple of days and spending time together after classes too hence why she was always late but was scared of bringing up this topic with him. I was surprised at how into this she suddenly was. I advised her instead of telling him about the cuckolding thing just pretend you are cheating on me. 

Saturday morning she told me that this guy wanted her to spend time with her. She asked me for my permission and I gave her the green light. We both knew what was about to happen. I was scared and jealous but the fact that my fantasy was about to come true made me ecstatic. I asked her since she couldn't tell about the cuckolding could she atleast record it secretly so I could watch it later but she told me it was literally a criminal offence to do so and I told her she was right.


Following night she didn't recieve any of my calls which actually turned me on. I was fantasising about how good he must be fucking her probably without any protection and masturbated thrice that night. Next morning she didn't recieve any on my calls either so I got a little worried. I thought about calling her roommate but she thought my gf was with me so I didn't want to spook her or something. Around 1 pm she texted me she was fine and just didn't have to look at her phone. I asked if she wanted to meet and talk about it but she told me it's Sunday so she might spend some more time with him. I was angry at this point because this was not what I had agreed to and  imagined going down in my mind but at the same time couldn't tell her anything because I thought she was only doing this for me. 

She came back home late and we didn't really talk about it over the phone. I thought it was better to talk about this in person. Next day I met her and asked her about it but she kept refusing. We went back to my place and I kept nagging her about it. She got very angry and told me he was way bigger than me and cummed inside her so many times she lost count and enjoyed every second of it. Tbh I was devastated to hear that and after that almost every thing went in a  downward spiral. We stopped talking for a few days. She stopped returning my texts and when I enquired about her with her roommate she told me my gf was staying at her aunt's place for a few days which I knew was bs and that really hurt me.

We stopped talking after that for a long time cause I gave up on her tbf. I do feel I'm more to blame but at that time I was only blaming her. On 2nd November, her bday, I wished and told her I hope she is happy with him. She couldn't help but cry and apologize.  She came over the next day and I told her I was sorry to put her through this. She was honest and told me she was with him for the past several months, told me that it meant nothing with him and they don't even talk anymore.


We are back together now stronger than ever. But the recurring images of he