Back when I was in college, I had a few experiences with various people and I will share those stories later. These are all real and I’m sharing them to get them out there and maybe find some people to talk to about them. All of them were fully consensual and most of them were very sensual. But this one involves myself (30M at the time) and my Fraternity Brother’s grandmother (60F at the time). To note, I was about 6 years older than him and his mother was a teen mom, so the ages are accurate here.
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The day I became his mentor while he was still a pledge, we did a getting to know you Q&A thing, wherein he told me that one of things that bugged him the most was that how often his friends would say his mother was a MILF. Having never seen his mother, I told him that he wouldn’t have to worry about that from me, but his best friend (and pledge brother) interrupted us and showed me her facebook page… I bit my tongue, but actually, yeah. She is a fitness rep and writes self-help books on physical and psychological fitness. Even now she has a pretty big social media following related to her looks, so…
Anyway, jumping ahead, I become involved in his family and his life and keep getting invited to family things with them, which I obviously went to because free food and good looking girls… what late-20’s guy wouldn’t want those things? Of course, it became apparent that I wasn’t going to get any closer than casually friendly with his mom and stopped trying. Just kind of enjoyed the friendship I had and the chance to hang out with the family at the beach and other trips that we went on.
Eventually, he gets engaged and his fiance announces her pregnancy, so we have a joint Wedding and Baby Shower, and as expected, I’m invited. At the party, I’m just hanging out with the guys, doing the frat bro guy thing of cigars, drinks, and talking shit about stuff, and I’m approached by his grandmother, bringing me another drink because she noticed mine was empty. I thought she was just doing that grandmotherly thing, but when she walks away, the guys all start giving me a hard time. Apparently, she’d been flirting with me this whole time and I’d been too focused on my friend’s mom to notice, and when I walked through the memories with the guys, seeing it from their perspective, I realized that they had some pretty strong evidence.
At the end of the event, I help clean up and I decide to help his grandmother take out the trash, mostly so I can talk to her alone. When we were standing outside at the end of her family’s driveway, I just straight up asked her if she was flirting with me, and she confirmed she had been. She was embarrassed, but I told her that actually, if I had noticed sooner, things would have been different. We talked a little more and made a plan to talk about it at my place later that evening. TO NOTE, I shared a place with this guy and his fiance at the time.
When she arrived, she was wearing an evening dress and had put on make-up. Jumping right in, I told her how little she needed it. She was the genetic progenitor of the MILF mother, after all, and was, by all definitions, a GILF. Granted she didn’t have the same endowments in the chest or ass area as her daughter, but some parts of me also think that some of that was fake, but she was still a slim, elegant lady whose hair only had a few streaks of grey. She thanked me for the compliment and I opened the wine she had brought. We talked about a few things related to my friend while we drank a glass and genuinely enjoyed probably 20 minutes or so of each other’s company.
Eventually she dropped the “you have beautiful eyes” line, to which I responded that she did as well. We did that thing where people look at each other for a moment and then I leaned in to kiss her. She accepted the kiss and it turned into some passionate kissing. Setting the wine down, I leaned her onto the couch (the same one I shared with my friend and his fiance), and lifted her dress enough to see what was underneath. I don’t think she expected me to do what I did, and it seemed that she’d never been with a man who did that sort of thing, but I used my tongue and fingers to please her. When she came, both of her hands were on my head, pulling my hair, as her legs clamped down, almost crushing me. I was enjoying it as much as she was.
When I came up from under her dress, she wrapped her arm around me and confessed that it had been a long time since she’d been with anyone and that she hadn’t come to an orgasm that most recent time, so this was already a better experience. I told her that it was because she hadn’t been with younger men, to which she gave me a cocky “You don’t think so?”
Turned on, I started kissing her again and she pulled me on to her. I don’t remember who undid my pants, but I remember that I was hard, laying on top of her, pulling her panties aside, when she stopped me to ask about the condom. Not that she was worried about getting pregnant, just… you know… being safe about STD’s I guess. I got up, went to my room, grabbed a condom, and when I returned, she’d removed her dress and was propped up on the couch on her knees. Unfortunately, the couch was angled so that I saw her silhouette as she faced the door to our place, but when I came around the table, I got a nice view of her ass and the pussy that had produced four children.
I knew I could have stopped right then, could have walked away, but instead, I rolled the condom on, squirted a small, one use packet of lube onto the rubber barrier, and inserted myself in. There’s something different about this kind of mature woman, an older mother, and it intoxicated me. She moaned with pleasure and started bouncing her hips back at me. I jokingly said, “Get it, Nani” which was her nickname in the family and she replied immediately with “Oh, I’m going to.”
After that, it was pretty animalistic, with me grabbing her hips and pounding into her from behind, her arms giving out and she practically fell over the arm of the couch, the sounds of out skin slapping together almost as loud as her moaning, sweat, grunting, panting, and of course, the wild orgasm that started with her having an orgasm that crushed her muscles down on my cock, and ended with me exploding a whole load into the empty tip of the condom.
After I pulled out of her, she collapsed into the couch and I saw a concerned look on her face. I was a little worried that I had gone a little crazy, but she said she liked it. However, she did admit that the whole time she’d been looking at the door and as I was cumming, she had the clarity of thought to worry about my friend walking in any minute and seeing her like that. That got us to talking about how maybe pursuing things beyond this point was probably a bad idea, but that we had both enjoyed the situation.
We got dressed and we finished the bottle of wine while talking about our sexual histories. It wasn’t a pump and dump situation by any means, and after she felt like she could drive, I walked her to her car, gave her the final kiss that we’d have together, and cleaned up the mess we’d made in the living room. My roommates arrived sometime after I’d taken a shower and went into my room, which meant there actually was no reason for us to have worried, but still.
After that, we bumped into each other a few more times at events and when I helped them pack up their house so they could move to Florida, she gave me a gift. SECRET: I still have it and my friend has actually seen it a couple of times. I don’t live with him anymore, but he’s come by a few times and has seen it. Even commented on it once, not knowing that it was something his grandmother gave me for knocking boots with her.
Source: reddit.com/r/gonewildstories/comments/w66wtd/mf_i_30m_hooked_up_with_my_frat_bros_grandmother