[MF] You always remember your first mind blowing MILF

Inspired by my recent connection I’ve made with u/puriuh I have taken up sharing my sexploits in written form because this man hoe has seen some shit and been around the damn block. Sit the heck back and enjoy and hopefully someone gets turned on by this.

**The Preamble – Circa Winter 2013**
So, 22 year old me, was no more or less of a horny bag of heat than I am now, but definitely less wiser and maybe a tad naive, regardless, that was most definitely the age in which I blossomed sexually. From the moment I started noticing women romantically and sexually in my teens beyond just preferring bigger and curvier body types, I had begun to notice that older women often caught a certain fancy in my eye.

It was never any friends mothers weirdly enough (such a common trope, I know) maybe it was a few teachers, maybe it was just the fact that when you’re younger and discover porn, even when you’re 14, any girl you’ll see on cam is 18 and up everyone looks older, or maybe older mature women are just undervalued beauty and sex wise and I’m here to balance the equation, regardless, I have my preferences and 22 year old horny me was ready to seek them the fuck out.

This was back when craigslist was a valid enough place to hunt down personals ads and okcupid was still an actual dating site and tinder was barely taking off, I don’t even know if r4r pages were a thing back then but I’m going to assume they were.

**The Hunt**
Anyways, once I became sexually active and begun to embrace my urges and seek out partners casually or otherwise online I figured I would make it my goal to aim for my ultimate fantasy, a night with a mature and experienced woman who would rock my world. So every now and then I would post ads or filter through the local craigslist personals and set my okcupid age preferences to at least 40+

Months went by and while there were a few mild hits here and there, nothing solid emerged. Anyways, on a whim and a chance, one night early in November I got a text message from a certain lady. Ms. K we’ll call her, had messaged me back, said she liked what she read and saw and that both her and her boyfriend had me in their consideration for the meet up.

“what kind of ad did I just respond to” I thought to myself. While I hadn’t yet participated in a threesome, I will admit I would fire off responses left and right to any ad that seemed to involve older women. and since her description of “busty mid 40s milf” was mostly likely what caught my eye, the details were what had escaped me.

So, in doubling back, turns out Ms. K and her man were looking for candidates for a gang bang and I was a prospect. So later that night I called and spoke to both of them on speaker phone and while I was nervous as all hell they both seemed nice and eventually Ms. K and I got to talking and texting on our own. Things slowly built up interest wise and while I may have been a bit of a chatty cathy, she was definitely into me so we pushed for an ice breaker meet up at a local park.

**They Meet**
I recall being very nervous but still very confident and when met she was rockin the promised busty body in jeans and a t-shirt, typical mom shopping on a sunday. I went straight in for a light hug and easy kiss on the cheek. We talked, walked around the park, got to know each other a little and overall set each other at ease. She also informed me that most of not all her other candidates were turning out to be duds or just bad juju that didn’t meet expectations upon meet up and she was becoming disappointed sans me.

Either way, to top off our positive meet up, we had been sitting in the grass under a tree, hands petting hands and just flirting and talking when her son (not 2-3 years off from my age) called her asking where she was and if she could pick something up for him while she was out shopping (her cover for him). She played it off very well but I had made her put the call on speaker phone while I stroked her thigh playfully and had to watch her struggle to stay composed and talk to her son like she wasn’t sitting right across from a young buck almost the same age who she was planning on fucking. It was hot needless to say. Afterwords, though flustered, she said she liked me and when we walked back to the cars she said I could text and call whenever she was free for now and that she’d keep me posted, we when in for a quick but intimate kiss and i made sure to get a nice grab of her ass and slip my tongue in her mouth for a sec before we left.

It was a good first meeting, to say the least

**The wait**
A few weeks passed. She was still attempting to vet other candidates. She was having zero luck. But her and I were flirting, texting, sending nudes back and forth and just keeping the heat coming. My jittery but excited self may have been a bit too eager but for the time, she was enjoying it. Regardless though, time was passing and I was still her only solid candidate for the ever illusive gang bang. I can’t say I wasn’t tired of waiting but I think she was feeling the same way.

When we both realized this was taking longer than planned, I shot my shot and asked if she wanted to just skip the gang bang and have a night with me and her. So she got the ok from her boyfriend and we began to plan.

**Road Rash**
It was the first Saturday in December of 2013, I had just gotten off work, headed home to shower real quick and was ready to have my world rocked by my fantasy woman. We had agreed that our first time was going to be car sex. Hot spicy and simple. Also, neither of us had the time plan a room rental and she was the one who suggested it so I had no qualms.

So after prepping and making sure I was suitable for sex, I headed off to the local bus depot (parking is free there 24/7 and its quiet and open at night). Our cars rolled up next to each other and I got out and jumped in her back seat. She was wearing a lower cut blouse and some tight jeans. We had originally planned to try fucking in the bus depot but not a minute after I had jumped in her car, we had noticed a low lit cop car cruising the far side of the depot and voted to try to find somewhere to park instead. So off we went.

As we drove we flirted a little while i began groping her form the back seat, feeling up her very full 34DD chest and thighs while she tried her best to focus on the road. After driving around for about 20 minutes and almost feeling out of luck (it was maybe 11:30PM) we passed by a local outlet mall, where a Wal Mart was the main attraction, but deeper in, the lot had some twists and turn and some darker sections where a car could easily be concealed and passed by, with the only road being a side road that truckers may have used so we decided to give it a shot.

We parked generally out of sight, dimmed the lights and got in the back seat together. She began to touch me as well and we began a very slow and sensuous make out session as I continued to squeeze her breasts in my hand. I eventually pulled out her tits and began to play with her nipples and put them in my mouth till they were hard and wet from my spit.

As we both realized clothes were becoming an issue we made a move to just undress right then and there. (you have very limited movement options in the back of a Nissan Altima), so less clothes was ideal. Once our clothes were placed in our respective front seats (gotta stay separated for easy access post sex lol, Car Sex tips 101) she pushed me back and started to suck on my rock hard cock. What I would experienced was one of if not the most intense blow jobs of my life. It was like her mouth was a second vagina. She tounged and squeezed and sucked and applied pressure in the back of her throat as well as with her cheeks and in maybe 8-10 minutes I could feel myself giving in and started to mention “Ms. K this feels good but im going to cum already if you don’t stop” and all she did was look up while continuing to suck and didn’t skip a beat. Her eyes said it all, she was determined to make me pop. And just like that I was melting in her hands and mouth, I came to a very intense initial orgasm and she swallowed it all. Whipped her hair back, took a sip from her water bottle and said “ready for round 2” and all I could do was sit there reeling in ecstasy.

While I was still hard, I needed a minute to fully bounce back so she laid back and gave me a lesson in advanced pussy eating that I’ll never forget. She taught me how to use delicate but still firm circular motions on her clit, she taught me how to suck and lick her clit while fingering her pussy, she taught me how to be patient and what signs to look out for and most importantly she taught me the most important rule for making women orgasm, consistency, never stop until they say they are done. Ride through the moans, ride through motions that seem like they may want you to stop. And I brought her to an orgasm that made me feel confident but also like her little play thing. Did I make her cum or did she make me make her cum. My mind was still too turned on to care but my cock was stiff as a brick again and ready for the main event.

With that she sat me down, flipped around to angle herself good and sat her nice thick milf ass onto my cock and her pussy was wet and soft like heaven. I had the pleasure of being able to go inside her raw because she had already had her tubes tied a few years previous so we were safe and it was also the first time I’d experienced raw pussy, I was reeling with pleasure. Arms gripped around the front seat head rests and her head angled down, she began to grind her ass against my dick and fucked me real good. I spanked her and got my hands all over her ass and thighs and tried my best to match her motions and speed up a little on my own and she was starting to moan and get into it herself. After about 20 minutes of just sensuous fun riding. We flipped over. She was side ways in the back seat and I did my best to get on top in an angle that worked for us both and went to town. The whole time watching her face shift between the face of a woman who had complete control over me to a woman who was loving the dick she was getting and just feeling herself. I felt so empowered but so intimidated at the same time. We both knew what we wanted but I never imagined that even in such a vulnerable surrendered position that someone could still have such control over the situation. After maybe about 10 more minutes of good fucking I could feel her pussy begin to constrict and perform (what I didn’t really understand at the time were) kegels. She told me to slow down and enjoy the feeling and within a minute or two of her constant moist contractions she forced me to cum again in another intense fit of orgasmic pleasure and she had nothing but a smile on her beautiful face watching me fill her up and make me her boy toy.

**The Dream Deferred**
Afterwards we sat up in the back seat for a minute and ran our hands across our bodies, exchanging a few words and laughs and killing off that water bottle. We then proceeded to step our sweaty naked bodies out of the car to get dressed in the lot, mildly afraid we’d get caught by a random passer by but managing to pull it off without a hitch. She drove me back to my car. Kissed me good night and we both went on our way.

When I returned home, I thanked her for a mind blowing evening and said that I’d like to do it again sometime and she said she’d let me know.

While I would love to say this ended honkey dorey and we had many other wild nights, I have to end on a very flaccid note and say that this was a one time affair. The next day I woke up and while I was satisfied, young innocent and still blooming sexually 22 year old me felt a strange conflict within. As someone who was still figuring out intimacy and relationships for himself at the time a strange push in my not yet confident gut told me that maybe these kinds of casual connections weren’t the best for me and that maybe I shouldn’t do this again.

Looking back I’m almost certain that that was the voice of religious shame and guilt from my childhood I hadn’t fully worked through but regardless, I had sent out a message to her telling her that was how I felt and that it was probably best to just call it there. Naturally a week or two later, me having not learned my lesson, I felt like a fucking dumb ass and had attempted to reach out again but I already knew that there was no way she’d be interested again after that kind flip flop. It was bitter sweet and looking back, it’s honestly one of the stupidest decisions I’ve ever made.

I have no regrets but it’s a situation I learned so much from. I am now a much more well versed and confident individual sexually. I know what types of relationships I value and how to have healthy casual intimate situations and embrace the needs and urges of my body. Unfortunately, my struggles cost me a potentially bountiful relationship with a classy, beautiful milf for the ages but at the same time, to have experienced such a night is something I will forever remember and be thankful for.

Ms. K, thanks for the memories.

Source: reddit.com/r/gonewildstories/comments/ebsy7i/mf_you_always_remember_your_first_mind_blowing