Straight Female / 24
Dating An Older Man
I saw a post a few weeks ago regarding a woman having a relationship with a much much older man. I think she was in her 20’s and he was in his 50’s. I am in the same situation and I cannot find any reason to stop.
I have known this man forever through a local charity that my family supports. He is genuine, honest, hard working and most importantly a generous (to a fault) guy with everything - time, money, hospitality, etc.
Our relationship started at one of the charity events. By chance, we ended up being partnered to do a weekend’s worth of tasks. It was fun, interesting, eye opening and easy being with this much older man. We have very little in common but this charity event spurred a connection, a commonality in our personality. As day one finished, I told him that I was supposed to be going out on a date, but the guy cancelled. I wasn’t mad or upset, but maybe a little frustrated over the late cancellation. Feeling my frustration, this man says I am free tonight, I will take you out if you are interested. My treat completely, but I do not eat sushi! Then he laughed. I was intrigued, concerned, open minded and maybe a little excited all in the first 15 seconds after he made the offer. I told he didn’t have to do that, to which he said ‘I want to!’ After some closing out of our day, I asked him if the offer still stood and he said certainly. We went our separate ways and we would meet later for dinner.
We decide on a restaurant on the marina and it is literally a perfect evening - weather, food, company - all good! He is genuinely a nice guy! The night finishes and as he walks me back to my car, he opens my door for me too. Nobody has ever opened a car door for me!!! I find myself softening to the idea of actually moving forward with him. He reaches in to hug me goodbye and (in a very awkward moment) I leaned in for a kiss. We both laughed out loud and I said can we try this again? We kissed each other goodbye (twice) and said we will see each other tomorrow.
The next day is just as good, but there is certainly a flirt overtone to the day. I can’t lie, I was horny for him by lunch time. We finished the day, went out for dinner together and agree to go back to his condo on the shore. The views were incredible! The condo was beautiful. Clean, organized, well kept. He had pictures of his family all over his condo, even his wife, who by the way I did know a long time ago before her passing.
We started kissing as we looked over the ocean. His hands, lips and tongue seemed to find my trigger zones, eventually leading me to go down on him. His cock is the largest I have experienced. I wasted no time and took him in my mouth. (Remember, I was horny by lunchtime). He just stood there, towering over me as I sucked and stroked his heavy cock. He was enjoying this, but my pussy was literally soaking my panties so bad that my panties were stuck to my pussy. I needed him to fuck me! I told him to sit on the couch. I straddled him and lowered my soaked pussy in his slippery cock. It met some resistance but his hands on my hips pushing me down passed that barrier with just a little coxing. I felt his balls hit my lips and I let out the most guttural ‘oh fuck’ ever. My eyes closed, I grabbed his shoulders and I took a deep breath. Up and down, slowly at first. My pussy was soaked as I started to ride him faster. Harder. Deeper. Then it hit me….oh fuck, he is not wearing a condom. Like most woman my age, I am in the pill so it did not matter in the way of getting pregnant, but other ways may have been an issue. I got past these thoughts when my pussy started to fail me and she started to cum. This 58 year old man, hard as a rock, buried deep inside of my pussy, is making me cum. He grabbed my hips and powered me through my cum. I fucking soaked his couch.
He picked me up, without ever pulling out of me, and fucked me again the wall near the sliding glass door for maybe five minutes. My juices could not stop from dripping down my and his legs. This position was new for me and I came again. I climbed off, stumbled from my weak knees and followed him to the bedroom where he proceeded to completely fuck me silly doggie style until he drained his balls in my very welcoming pussy. As he pulled out, his cum dripped everywhere. I spun around, took his cock in my mouth and cleaned my thoroughly. I spent the night there and we fucked in the morning again.
We both headed into our days and we decided to see more of each other. That was about a year ago and we are still together.
I have known this man forever through a local charity that my family supports. He is genuine, honest, hard working and most importantly a generous (to a fault) guy with everything - time, money, hospitality, etc.
Our relationship started at one of the charity events. By chance, we ended up being partnered to do a weekend’s worth of tasks. It was fun, interesting, eye opening and easy being with this much older man. We have very little in common but this charity event spurred a connection, a commonality in our personality. As day one finished, I told him that I was supposed to be going out on a date, but the guy cancelled. I wasn’t mad or upset, but maybe a little frustrated over the late cancellation. Feeling my frustration, this man says I am free tonight, I will take you out if you are interested. My treat completely, but I do not eat sushi! Then he laughed. I was intrigued, concerned, open minded and maybe a little excited all in the first 15 seconds after he made the offer. I told he didn’t have to do that, to which he said ‘I want to!’ After some closing out of our day, I asked him if the offer still stood and he said certainly. We went our separate ways and we would meet later for dinner.
We decide on a restaurant on the marina and it is literally a perfect evening - weather, food, company - all good! He is genuinely a nice guy! The night finishes and as he walks me back to my car, he opens my door for me too. Nobody has ever opened a car door for me!!! I find myself softening to the idea of actually moving forward with him. He reaches in to hug me goodbye and (in a very awkward moment) I leaned in for a kiss. We both laughed out loud and I said can we try this again? We kissed each other goodbye (twice) and said we will see each other tomorrow.
The next day is just as good, but there is certainly a flirt overtone to the day. I can’t lie, I was horny for him by lunch time. We finished the day, went out for dinner together and agree to go back to his condo on the shore. The views were incredible! The condo was beautiful. Clean, organized, well kept. He had pictures of his family all over his condo, even his wife, who by the way I did know a long time ago before her passing.
We started kissing as we looked over the ocean. His hands, lips and tongue seemed to find my trigger zones, eventually leading me to go down on him. His cock is the largest I have experienced. I wasted no time and took him in my mouth. (Remember, I was horny by lunchtime). He just stood there, towering over me as I sucked and stroked his heavy cock. He was enjoying this, but my pussy was literally soaking my panties so bad that my panties were stuck to my pussy. I needed him to fuck me! I told him to sit on the couch. I straddled him and lowered my soaked pussy in his slippery cock. It met some resistance but his hands on my hips pushing me down passed that barrier with just a little coxing. I felt his balls hit my lips and I let out the most guttural ‘oh fuck’ ever. My eyes closed, I grabbed his shoulders and I took a deep breath. Up and down, slowly at first. My pussy was soaked as I started to ride him faster. Harder. Deeper. Then it hit me….oh fuck, he is not wearing a condom. Like most woman my age, I am in the pill so it did not matter in the way of getting pregnant, but other ways may have been an issue. I got past these thoughts when my pussy started to fail me and she started to cum. This 58 year old man, hard as a rock, buried deep inside of my pussy, is making me cum. He grabbed my hips and powered me through my cum. I fucking soaked his couch.
He picked me up, without ever pulling out of me, and fucked me again the wall near the sliding glass door for maybe five minutes. My juices could not stop from dripping down my and his legs. This position was new for me and I came again. I climbed off, stumbled from my weak knees and followed him to the bedroom where he proceeded to completely fuck me silly doggie style until he drained his balls in my very welcoming pussy. As he pulled out, his cum dripped everywhere. I spun around, took his cock in my mouth and cleaned my thoroughly. I spent the night there and we fucked in the morning again.
We both headed into our days and we decided to see more of each other. That was about a year ago and we are still together.
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