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)
We made short conversation about how neither of us expected it to be a legitimate meeting. After some short and humorous dialogue, she stripped down naked and wanted to have full blown sex with me…raw! (Looking back it was very reckless of me to have unprotected sex with a stranger that I just met). It was an amazing time! She came over and over, and she wanted to get on top so she could ride me. Me, being in my early 20s, had plenty of stamina to keep up with her matured sexual libido. So maybe 30-45 minutes pass and I finally orgasm inside of her while I’m pinning her legs back.
Then, shortly after, the first meeting happens with the gloryhole guys. I decide to let her have her fun since she is trying to knock off a bucket list. Maybe 4 guys showed up within a timespan of 2 hours? At the end of it all, we have a long chat about how appreciative we both were about the other being honest and open with the situation at hand. It was like meeting up with an old friend, although we had never talked or met before in our lives. We ended it with her riding me until I, once again, came inside her. The last words from her to me where something along the lines of, “Well, I better get home and clean myself up before my husband gets home from work. He’s a master gunnery sergeant in the Marines and works late all the time, so I have just enough time before he gets home.” I was a Corporal in the Marines at the time. Who knows if it was some Master Gunnery Sgt I knew or not? Regardless, that was some of the best pussy I ever had and it has sparked my absolute love of MILFS ever since.
Source: reddit.com/r/sexystories/comments/qp6z27/gloryhole_setup_for_milf