[M]y Christmas Eve MIL[F]

I’ve changed the names and certain details, and certain aspects have been made non-linear for sake of clarity/to make up for my lack of memory taking its toll, but this was hands down the hottest night of my life.

Me: 28, 5’11-ish, Brunette, 165 lbs. with a toned build from weightlifting and a 6” x 5” penis (ok it’s within a rounding error of six, but at least I’m not saying it’s a 28″ cock like all the other guys on here!)

Lauren: 44, 5’9″, blonde/reddish wavy hair, legs up to her shoulders seemingly, a little bit of a belly but by no means fat, and (let’s face it, this is what you guys really care about) an ok ass & boobs that border on Ds/Es. Imagine if Susan Tedeschi’s hypothetical sister had slightly darker hair and was a little curvier and you wouldn’t be significantly off the mark. Steamy action starts at $$$$$$$$$

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So earlier in the summer my father met Lauren, a new friend with a few hippy-like tendencies combined with a strong faith in her religion. Our first conversation was not significantly memorable other than the fact that she was going to see a band I had seen a few times previously. I didn’t really talk to her that much otherwise partly because I am normally shy and awkward (ESPECIALLY around new people who are pretty women seeing as I had only lost my virginity a few months prior), and partly because our neighbor Lance was really laying on the flirt with her as we all hung out on a nice summer’s day. Nonetheless we got along well and I could see she was attractive but viewed her completely platonically.

Over time she and my dad started hanging out more and she became more of a fixture in our lives, especially in the months leading up to our night together once she started dating Lance on and off. In the early fall, my mother told me after the two of them hung out the Lauren had said she could see herself dating me. At the time I had kind of dismissed the idea 1) because I had barely spoken to her previously due to my aforementioned shyness, and 2) because she was nice but kind of “damaged goods” (rough custody battle, a little too much interest in certain new age tropes/her religious choice, the large tattoo she had, etc.). Dad suggested it could be a way to get some experience dating but did not recommend it get more serious than that. There were moments here and there when the thought would continue to percolate in the back of my head (especially if I ended up seeing her in a robe for whatever reason), but nothing I could immediately pick up on at the time.

Fast forward to Christmas Eve. She and her 7 year-old son were coming over to spend the night over at our place for Christmas. After a perfectly platonic dinner (with no hint of anything sensual) happened the two of us cleaned up the various dishes that had piled up. For the first time since we met we spent a good amount of time talking. As we started taking shots of the various liquors that were assembled we started making comments, each one innocent enough on its own but tensions were sky high as the “age is just a number” quip was followed innocently enough with me telling her she didn’t look bad for 34. I may not be Ryan Reynolds when it comes to women, but even I could feel the sexual tension was thicker than the air on a late summer’s day. Finally we made our way over to the dining room table where I tried saying that I was attracted to her but my buzzed “just go for it!” self was in a battle with my sober “don’t do it she’s dating your neighbor!” self, with my “I’m a dorky awkward fuck!” self figuratively screaming in the corner.

$$$$$$$$$

Lauren could tell something was up and suggested we move to the couch. She suggested some cuddling after I still couldn’t manage to get the words out. After a little of this I said to her “I prefer steamy makeouts” and instantly recoiled and babbled an incoherent apology 1) because of the cheese factor, and 2) she was back in the “on again” phase with Lance. While she did remind me of that she then added on shortly afterwards that they weren’t exclusive and it “was good to keep her options open.” With that, our faces made the slow but determined journey towards each other until our lips touched, our eyes closed, and our tongues started to dance softly yet intently. Our styles of kissing could not be better matched; it seemed as if each of our lives lead up to this moment of two people kissing each other perfectly in sync with each other. All the while my hands roamed across her neck, head, and shoulders but never anything more intimate than that for fear of moving too fast. I realized I wouldn’t have to worry about that once she pulled down her leggings a little bit and brought my hand to her crotch, which was just past the stubble phase. I teased her by massaging and firmly caressing her in between her legs but over her leggings for a minute or two before I finally gave in and ran my finger across her wonderfully soft and drenched lips.

After teasing her with my fingers for a nice little while, I then knelt down on the ground, planted a few kisses on one leg, then the other, before I couldn’t resist myself and I had to taste her. Her juices were so unbelievably sweet that she could single-handedly turn any man into a fanny-licking fanatic. I may be a man who really enjoys the way pussy tastes, but her taste to other pussy is like comparing cold cuts to Michelin stars. I started with nice long and slow licks before moving one arm to wrap around her leg, and bringing another one up to her boobs. She wasn’t flailing in that over the top way you see in porn, but having her throw her head back as as I sucked on her clit was divine enough. What made me feel like the sexiest man in the world though was when I added my fingers to the mix and feeling her hand on my head. After a good while of this (just before my jaw started to hurt), I made my way up to her face to start making out with her again and to remove the rest of her clothing. I made her way down to her chest and would discover that her nipples were utterly perfect.

I don’t just mean in terms of their size and shape (though her nips certainly were wonderful in that regard too). Some women have nipples where playing with them doesn’t really do anything to them, while others have sensitive ones where playing too much or too hard with them is too much to handle. As much as guys go crazy for women who can squirt, Lauren’s nipples were that wonderful combination of resistant and sensitive that she could easily have a mini orgasm just by playing with her nipples. (Seriously, why don’t more guys make a bigger deal about hooking up with a woman who can nipplegasm? It’s the best!) We tried many different things throughout but what caused the best results were when I would suck on her nipple, then start nibbling ever so slightly, and finally alternating between the two as her face would tell me exactly what I needed to do to her without a single word being said. Unfortunately I couldn’t get her to fully cum for fear of screaming and waking up the entire house, but I may never forget after one nipplegasm she bit my chest and said “I have to do this to you so you know exactly how you make me feel” with a look on her face that I could only describe as erotically possessed before she pounced on me and shoved her tongue into my mouth.

After grabbing a condom I’d love to be able to tell you all how I thrust into her, pounded her mercilessly for hours, and got her to scream and moan like a banshee and almost wake the entire house up. Unfortunately for me, even though I thrust into her bareback (yeah I know…) I just couldn’t stay hard due to a combination of nervousness and jerking off too much previously since I had no idea any of this would transpire between the two of us. I really didn’t care though since I got to see her boobs bounce as I thrust into her and we made out as I was inside her. I’m not sure what exactly it is about making out and thrusting that does it for me, but getting to experience both sets of a beautiful woman’s lips at the same time is one of the best things in the world.

After alternating between unsuccessful thrusting, making out and nipplegasms, eventually she made her way down in between my legs and started sucking me off. For the longest time I thought I was one of those guys who just isn’t into getting my cock sucked. They don’t really excite me when I see them in porn and the last one I had there was a bit too much teeth involved. Lauren was different. She didn’t just suck my dick to get me off. She didn’t even do it because she enjoyed it. In that moment she was completely different from the woman I had met a few months prior and she sucked me off like I had the last drops of water on the planet. While there wasn’t a ton of spit involved, there was enough slurping and moaning coming out of her mouth that the only way you couldn’t enjoy her blowing you would be if you weren’t into women. Everyone always says that the sexiest thing a partner can have (even more than a nice body) is enthusiasm. I didn’t realize a mouth could do some of the things hers did that night, and would have easily came buckets if I had it in me.

After the best blowjob of my life I sat on the couch as she draped her body across my lap. Both of us enjoyed some nice pillow talk as I talked to her about what turns me on and ran my fingertips across her legs, torso and boobs. Occasionally if there was a lull in conversation, or if I felt a little bit devious in that moment, I would attack her boobs with her mouth just so I could her sexy whimpers and see that look of pure, raw, unmistakable lust that would overcome her entire face.

Unfortunately for me (and to a certain extent for us) she ended up regretting that night because of complicated feelings on her end surrounding sex and other factors, so she and I will probably never hook up like that again. I’ve come to accept it (I don’t have a choice in the matter after all), but if I end up with a woman who is even a tenth as enthusiastic in bed as Lauren I will be a very happy man. I had my suspicions that I was into older women that night, and Lauren did nothing but confirm them.

Source: reddit.com/r/gonewildstories/comments/az63yl/my_christmas_eve_milf