My first older woman

A few years ago I was new to the area so I joined a "normal" dating site essentially looking for a serious girlfriend. I had dates and met some great women but as I searched the members in my area, I never before thought to search women older than me. I dunno. I guess I was looking for a wife and an older woman didn't fit the stereotypical vision I had. Anyway, I don't remember exactly but I'll bet it started with me masturbating while scrolling through users and I expanded my search to include women in their 40s. Then women in their 50s. (I was around 35 at the time.) It sounds silly now but I was just seeing how beautiful and sexy many of these women were! Maybe I could put a pause on looking for a wife? Would these women even wanna date a younger guy? None of my friends knew I was doing the online dating thing and I was a little embarrassed so I didn't have anyone to talk about this with. I thought, "Why not try?" I struck up some conversations with a few different women and I realized, this is a turn on. My first couple of dates were ok but didn't go anywhere. In fact, the sexiest woman so far pretty much just let me pay for dinner and drinks and told me I should find a younger woman. ? Undeterred, I dived back in the pool and immediately met Kim.

I could tell by her pics that Kim was in great shape for any age including her 50 years and she had gorgeous blue eyes and a great smile. One pic showed her with a sexy smirk and I thought it was really hot. We had some fun but mostly innocent messages back and forth and even though she lived about an hour away in a smaller town, that didn't seem to be an issue. I told her the next time she came to the city, I wanted to buy her a drink. Her quick response was to line up a date for that Friday. We decided on dinner and when I arrived, there she was. I'm over 6 feet and she was probably 5'5" and it was nice when she flashed her smile and I gave her a hello hug. Our bodies just seemed to fit together. Dinner was fine if a little quiet. Maybe we were both a little nervous at the 15 year age gap? The conversation was typical get-to-know-you stuff. I asked her if she wanted to head somewhere for an after dinner drink and she said she did. That was a good sign, right?

This next place had a band so it was pretty packed. We went to the bar and ordered drinks but with no where to sit, we just stayed there, leaning against it. The music was loud but there was an awkward silence between us like we had run out of things to talk about. She drove an hour, dinner, drinks, ... was this it? In the din of the music and crowd, and with nothing I could think of to talk about, I decided on a different approach. I caught her eye and leaned in and kissed her. It was quick and probably shocked her based on everything to that point! After that first kiss, I casually looked around and took in the scene. When I looked back at her, our eyes met and she had her face raised towards mine. She wanted another kiss. I happily obliged and this time, it started to get passionate. Right there in the crowd by the bar. What did those folks think? This guy and this sexy older woman making out? I didn't give a fuck. I was getting really turned on and I asked her if she wanted to leave. Hell yeah. We kissed a few times as we made our way through the crowd. Once out the door, we were all over each other. Standing there in the near dark of the parking lot, I pulled her against me as we kissed. My hands found her tight ass over her jeans. We stopped long enough to get to the car and then we were back at it. My apartment wasn't far, thank god, so we headed there with every red light a chance to kiss, our tongues entwined. Park the car, kiss, get out, kiss, hold hands to the shared outside door kissing, up the steps, and into my place.

We made it no more than 5 feet inside before the clothes came off. My god, what a body! So tight and tan. She later told me she had had a boob job but they looked and felt perfect. Perfectly shaped for her small body and not tight like some others. Perfectly suckable nipples. As we kissed, our naked bodies pressed against each other, she took my raging hard cock in her hand and led me to my couch where she sat me down and then dropped to her knees in front of me. I managed something like, "Take me in your mouth" and that's exactly what she did. She started licking my shaft then sucking just on the head of my cock which almost put me over the edge. "All of it", I said and she took me deep in her mouth. I remember that it felt so good. Being naked and getting a blow job? Of course! But the thing I remember that sets it apart was the feeling of her hair brushing against my thighs as she took me in and out. After a bit I gently pulled her head away from my now wet, throbbing dick, gave her a deep kiss, and told her I was going to fuck her. She gave a little purr and a grin. I grabbed a condom (wanted to make sure we both felt comfortable) and joined her back on the couch. She put it on me and then laid back, her legs spread a little as she touched herself. As I positioned myself over her, stopping only to kiss and suck her sexy nipples, we kissed while she took hold of my shaft to guide me into her. I stopped with just my tip inside her at first, rocking my hips up and down, then I put more and more of myself inside her all the while her hands were exploring the back of my head, down, my back, to my ass. She gave me sounds of contentment and I started pumping my cock in and out of her hot pussy. She felt amazing. I wanted to please her but I also wanted to concentrate on the moment and how great this felt. My cock inside her, her body under mine, the sounds we were making together. So fucking hot.

We had never even stopped to turn on a light when we got to my place but it was lit from the parking lot lights outside that filtered through the blinds. I had an idea. I got up and pulled the blinds up. Standing there naked with my hard dick, there was nothing keeping anyone from seeing me through my second floor windows if the outdoor lights illuminated me. I took Kim's hand and led her to the window. She leaned against it bracing herself with her hands on the window sash, halfway up. Her back arched and her sexy ass sticking out towards me. Could anyone see her? I positioned myself behind her, kissed her on her back, then grabbing her hips with both hands, and without touching it, I positioned the head of my cock against her pussy. I was about to plunge myself inside of her when she rocked back and took the length of me. Oh my god! This woman was exactly what I wanted. What I needed. I thrust my hips forward still holding her hips. Pumping my cock into her wet pussy. Was anyone watching us? All she could manage was "Oh god" over and over. And over. Looking down at my dick going in and out of her and both feeling and hearing her ass slap against my hips was too much for me after everything else we had done. I was just about to tell her I wanted to cum for her but before I could speak she instead reached back and grabbed my forearms (I was still holding her hips) and let me know she was cumming. She dug her fingernails into my arms as she convulsed and cooed. The pain from her nails gave me an extra moment but when I realized I didn't need to keep her from collapsing, I told her that I was about to cum too. I pulled the condom off and stroked my unbelievably sensitive cock for no more than 3 seconds before I unloaded on her back. My balls pressed against her ass. She told me she "Fucking loved it". I gathered myself and realized I needed to help her clean up so I got a warm washcloth and wiped my cum off her back and ass. Still naked, we went to my kitchen where I got us both some ice water. Being hot and sweaty but feeling cold kisses from the water we both drank was a memorable sensation.

I wanted her to stay for more sex but she said she had to get home to her kids who were too young to spend the night by themselves. I reluctantly understood and the rest of our evening together was just some kissing while we got dressed. The next day was mixed with both me jacking off thinking about what we did and some guilt. What did this mean? What type of relationship did she expect? She was 15 years older than me. I texted her my honest mixed feelings and she immediately put my mind at ease. She wrote back, "I know what this is. If we only want THAT, it's ok with me" and we met and sexted many times after as fun fuck-buddies. So began my love of older women.

This is all 100% true. Except her name wasn't Kim.