Cougar Chronicles: Kim (M25F39)

I have been a long time lurker on this sub, and finally decided I wanted to share some of the gonewild stories I have had with some amazing older women. This is my first post, so if I have something screwed up with the labels, let me know.

To start out, I have always had a thing for older women, but for my teens and early twenties, it was just a fantasy. I had a longterm girlfriend from highschool through the first part of college, and then we broke up my junior year. The rest of college was filled with random hookups with girls my own age, but I still had that nagging fantasy in my mind that I wanted to learn what an older woman could teach me.

Fast forward to 2009. I was a year out of college, and because I didn't want to live a 9-5 life, I worked as a bartender. The upside to this, is that it gave me the opporotunity to chat up lots of beautiful women. For the relevance to this story though, the job gave me plenty of free time.

Back when this story took place, Facebook was fairly new and they were trying out some type of chat application or dating website. This is how I met Kim.

Kim is 39, has 3 kids, and is recently divorced. Throughout the chat, we dive deeper into each others backstory, but kept the conversation to mild flirting. Over the course of the next week, we developed a friendship. We exchanged numbers and carried the conversations out over text. For all those people out there posting questions asking for advice, here is mine: Be nice and good things will happen.

For the next two weeks, Kim and I would text everyday. Mostly fun banter back and forth, with a flirty vibe. And then it happened. I had finally reached my breaking point and decided that I needed to make a move now or never. I sent her a text asking what she was wearing. She sent a pic of herself in a black bra and lacy underwear. Dynamic changed.

From this point forward, our conversations became more sexual in nature. I had never been with an older woman, and she had never been with a younger man. She had not had sex with anyone other than her ex-husband for 15+ years. We were both nervous. We made plans to get together, but something always came up. It was a real feeling out process. For the next month, we would text daily, make plans, send pics back and forth, and then she would flake.

Then I get a phone call at 4:30 on a Friday afternoon. She is going out with her friends, while I am going to work. She says that I should come to her house after as her kids are with their dad for the weekend. I say sure, figuring that something would come up. Fast forward to closing time, she sends me a text saying to come over, with her address and says that she will leave the door unlocked and will be in her kitchen with drinks waiting.

The entire drive over I am nervous. This is the first time that we are ever going to meet in person. And because I am nervous, I Knock. I hear shuffling, and after what seemed like an hour, the door opens and I hear 'Come in"

To try and paint a picture, Kim is 39, about 5'8, brunette, and thick in all the right places, yet with an athletic build. I am 6', 175 pounds, with blonde hair and blue eyes and I wear glasses. Kind of nerdy, but I rock it.

Kim opens the door wearing the outfit she had on from her night out. Black, skin tight top with tight jeans, that hugged every curve just right. She invites me into her living room, she grabs us each a beer and we move to the couch.

As we are sitting making small talk, we both just eye each other nervously, wondering what the other is thinking. After about 15 minutes of this, I make the decision that I am not going to spend the rest of my life wondering what might have happened. I look at her, place my hand on her cheek, and go in for a kiss. She loves it. We spend the next half hour kissing. I enjoy kissing, and I am good at it. Then she whispers the words that I will never forget "I can't believe I am about to do this'

Kim grabs my hand, stands up from the couch, and leads me to her bedroom. We are standing at the foot of the bed, making out, and she reaches for my belt, undoes it, drops my jeans to to the floor and grabs my cock. I could cut a diamond at this point, and want to get her clothes off more than I have ever wanted anything, but I take my time. I slowy strip her down using every ounce of self control I can muster, enjoying watching her cross her arms as the black shirt goes over her head, and watching her arch her back as I slide her jeans off.

I am now naked, standing face to face with a fantasy I have waited for my entire life. She reaches back, unhooks her bra, giving me a great view of her small C cups breasts, and I cant resist but to take a handful. They are incredible. Firm, with pointy eraser nipples and just a hint of sag. To me, they are perfect.

Kim drops to her knees and swallows my cock. Older women know things, and Kim had her black belt in cock sucking. For the next 15 minutes, she worshiped my cock. Switching from deepthroat, to sucking on just the head, the perfect amount of hand movement and ball play. I cannot take it anymore and tell her I am close. She proceeds to take my entire length is her throat and pick the the pace. I shoot a monster load down her throat and she continues to lick up every last drop and says the words that every man longs to hear " I love the way you taste"

As I collapse on the bed and try to catch my breath, I manage to say in between breaths that it is my turn to return the favor. I flip Kim onto her back, and slowly slide her black thong down her legs, revealing her perfectly shaven pussy. I dive in. She tastes incredible. I try to remember everything I have ever learned about eating pussy, and spend ample time on the clit, and bury two fingers into her sopping pussy and start reaching for the G spot. Kim is squirming, her pussy getting wetter by the minute, and i feel her body tense, and shake, and finally she screams that she is cumming and clamps her legs around my head and fingers to keep me from moving. As her orgasm subsides, she whispers in my ear "I want you to fuck me"

The holy grail. After 15 years or pubescent dreaming, I was finally going to fuck this milf. We start out in missionary. I tell her I want to enjoy the view, and tell her to guide me in. I watch as every inch of my cock slides into her waiting pussy until I bottom out. From here, I just remember looking in her eyes, and smiling. Over the next hour, we fuck in every position possible. Missionary, Doggy, which let me look at her beautiful ass, reverse cow girl and my personal favorite normal her on top.

At this point we are a sweaty mess, both exhausted, she cums easily, and has came multiple times in multiple positions, and our pace has slowed. I have not ruined the night by cumming within the first minutes, so I consider it a success. She warns that she is getting sore and may not be able to go much longer. As she rides, I tell her that I will get there, and take in the sight that is before me. A beautiful woman, on top of my cock, grinding her pussy on top of me. The pace builds. I tell her I am about to cum. She quickens. Faster and harder and faster and harder. I can see the mountain top and Ka Blam. I unleash the biggest load of my entire life inside of the beautiful milf. My first time ever coming inside without a condom (Ya I know-Im Smart). I can feel my cock pulsating inside of her. She is squeezing her pussy, milking every last bit of cum out of my cock. She collapses on top of me, and we are done.

As we lay in the afterglow, her running her fingers across my chest, I allow myself to look back on this night of firsts.

I hope you enjoyed this story as much as I enjoyed remembering it. I have plenty more stories of Kim and several other amazing older women that I have had the pleasure to get to know.

Let me know what you think.

Thanks

Source: reddit.com/r/gonewildstories/comments/3qm3rv/cougar_chronicles_kim_m25f39