Author: WannaBeCuck9494

My First and Only Cuckold Situation, PT 2

(Please follow up with part 1 of this thread)

So, after the hotel situation, my ex wife was much more confident in her discussion to finally perform a sexual experience in front of me with another man. About 2 weeks go by and she brings it up to me again while I was washing dishes. She asked if I would like to go to a hotel and do it again, but maybe go a step forward and have full blown sex with someone. Of course, I agreed immediately!

We reached out and found a guy. Now, from the years of asking her to cuck me, she knew I had a very particular fetish for interracial. So, we found a very handsome and well-endowed black man to meet with us at the hotel (we both are white). Time comes to meet with the guy and, again, she opted to wear a blindfold during this meeting.

Just as before, I walk into the hallway and encounter the man that was set to fuck my wife. I explained to him that it was our first time going all the way like this and that she was nervous, especially after seeing how well-endowed he was. He laughed it off and told me that he had done this with a few couples in the past, so he would take it as easy as she was willing to go. Read more »

My First and Only Cuckold Situation, PT 1

So my ex wife new for years that I had a cuckold fetish and wanted to see her with another man. For years, she refused to do it and would even get upset at the thought that I wanted her to be with someone else. Fast forward to right before we divorced…

She came to me as I was sitting on the couch and said something along the lines of, “You know how you have always wanted to see me suck off another guy, or have sex with another guy? Well, since we are splitting, I figured there is no hurt in doing it now.” I can’t begin to tell you how excited I got when she brought this up on her own!

Long story short, we found a local guy that was down for a blowjob from my ex wife while I sat back and watched. We rented a hotel room and invited him over. She dressed in some sexy outfit and wore a blindfold (she felt more comfortable not seeing the guy). I walked into the hallway to meet him and give him the run down of what we expected. Basically, I told him that she was just wanting to give him a blowjob and that she would be blindfolded, on her knees net to the bed. All he needed to do was drop his pants and let her go at it. Read more »

Gloryhole Setup for MILF

Several years ago, Craigslist had a “personals” tab where people would post about different sexual experiences that they wanted to partake in. Sometime around 2016 or so, I made a post about wanting to set up a homemade gloryhole in my apartment to suck of as many guys as I possibly could in one day (orally bi male here).

Reply after reply came to my email from different men wanting a quick fix to their sexual frustrations. Many didn’t care if it was a man or a woman on the other side, as long as they got off, they didn’t care. Well, this is when things turned into what seemed like a porno for me lol

Someone claiming to be a older female (50 years old or so) messaged me, stating she had a sexual bucket list and wanted to fulfill the gloryhole aspect of it. So, we agreed to meet. A made the gloryhole out of an old bed sheet with a hole cut into it. At first, I was naked with my cock sticking though the hole. She immediately drops to her knees and begins to suck it. After maybe 5 minutes, she asks if she can come on the other side of the sheets. “Of course!” I say to her. An arm comes under the sheet and appears a blonde woman, somewhere in her late 40s or early 50s. Thin build, about 5’4, and very beautiful. (Similar look to a Michelle Pfeiffer or Jane Krakowski) Read more »