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My First Older Woman
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My First Older Woman First, a little background of my past and that may help explain a few things. I grew up in Manhattan on the upper east side. Don’t let anyone tell you that the upper east side and NYC as a whole is not highly sexual. We have a lot of young professionals who live there along with models, TV personalities, successful business men and women, stay at home moms (MILFs) and cougars. I grew up there, went to school there and worked in my apartment building as an elevator operator while in college. I often worked the grave yard shift of 10 PM till 6 AM during the school year. That shift is a time that was ripe for people coming home slightly drunk to very drunk, alone or with a hook-up. After midnight on weekdays there was very little foot traffic coming or leaving the building. Regardless, the first few hours were active and I enjoyed every bit of it. I have a lot of stories that involve various kinds of sex growing up in NYC. I read a thread of stories here on Wifelovers of young men having sex with older, more mature women…MILFs and Cougars. It bought back a lot of memories for me. I’ve decided I should share at least one of them if not more of them. I am not a professional writer but here is my story anyway. I hope you all enjoy it. A little about me: Ever since I had become sexually active, I always wondered about older women since I noticed that some in their forties even fifties were still sexually pretty damn hot. I have always had a very high libido and I loved sex. I still do. Our apartment building had a lot of really attractive older women in their late 30s, 40s and 50s. If they were married the one thing they all had in common were husbands who were professionals and traveled often. As an elevator operator in the building, you figure out pretty quick who is cheating on their husbands and who aren’t. Some of these women also had at home but the ones with teenage daughters were particularly interesting. Today, I am 57 years old, divorced but with a sexy 58 year old live-in girlfriend who I share with other men when the opportunity is right. As I said, I have always had a very high sex drive, I love sex and even though I am happy to be able to get it up twice a night occassionally today, back when I was a three to four times a night was easy and women loved the fact that I always came a lot. They always seemed to appreciate my large cum loads. To this day, I still cum a lot. Anyway, the story I wanted to share is about my first time with an older woman. I was 21 at the time, a college student, had a hot sexy girlfriend, I was a rugby player so I was definitely in really good shape with a lot of stamina, and I was literally having the time of my life. This was in 1978 and my mother had a very attractive friend named Lynn. She was 46 years old, a<b> nurse </font></b>in the doctor’s office next door, very attractive with big tits (I was always a tit man) and, interestingly enough, an ex-nun. I found the ex-nun part very intriguing obviously. I knew that she had several relationships going on, every once in a while a guy would move in with her but they were always around her age of older. She would come over often at lunchtime or after work and hang out with my mother. So, I would always run into her and chat briefly. On her breaks, she would come over and chat with the elevator operators and hang out in the lobby. In the summers I would work various shifts depending on who was on vacation. Being an elevator operator of a 64 unit apartment building meant that you had plenty of down time. You waited till someone would buzz you and then you would go up and get them. So, there was plenty of time to sit in the lobby and talk. Lynn was always fun to talk with. She was very down to earth, almost a free spirit in some ways and she loved to flirt. We’d talk about relationships and she would tell me about the guys she dated, the issues she had with them, etc. It all started out very innocent. As we talked more and opened up more, I felt very comfortable asking her questions about sex, anatomy, biology, etc. I didn’t have any shortage of sex but I didn’t really know about sex, about various aspects of it, etc. She was a wealth of knowledge as a<b> nurse </font></b>and as a friend who had an active sex life as well. We talked about all kinds of things, all aspects of sex including swinging and how she had never been to Plato’s Retreat, which was the “in place” to be if you wanted to swing, because she didn’t have anyone to go with and she’d love to go. Yes, I have some stories about Plato’s Retreat but this story is about my first time with her. Needless to say, I always enjoyed our talks and our flirting grew bolder and bolder. It became more and more explicit over time. One night I got home from school later than usual and Lynn was still at our apartment hanging out with my parents. My mother explained that Lynn’s car had broken down and she needed a ride home. She lived in the suburbs of Westchester County. I was more than happy to give her a ride since I did consider her a close friend that I had confided in often. As we were walking to my car, she was talking about something or other but I caught myself thinking that being in the car would be really the very first time that we were completely along together. Of course she was flirting with me and I think she really enjoyed the flirting, the sexual innuendos since I was a horny 21 year old and she enjoyed seeing my reactions to thinks she said. Anyway, we started our drive out of the city and the flirting became more and more intense. I definitely had a hard-on and I was happy to play along. She was telling me about how she hadn’t had any sex in a few weeks, asked me how long it’s been for me (2 days ago, it was in the elevator late at night but that’s another story) and I remember her asking me if there’s anything I could have right now what would I want. I mean, I was driving and my options were limited but I looked over at her and told her that I wanted her to take her top off including her bra and I wanted to see her tits exposed for the rest of our ride to her house. She looked at me for a moment, hesitated slightly and then the top came off. I was impressed that she actually did it and very impressed how good her big tits looked. She had nice size nipples that grew harder the longer they were exposed. She smiled at me and asked me if I liked what I saw. I absolutely did. Her tits sagged a bit but they looked great. I could feel my cock getting harder. She reached over and grabbed my cock before I could even answer and she said that the answer was clearly yes. I smiled and said thank you for doing that. I slowed down my driving a little since I was clearly distracted at this point constantly looking over at her. She explained that she was submissive to men and when I told her, commanded her, to take her top off she did. She liked being told what to do. The concept of submission was new to me but I always knew that I liked taking control when I was horny. Most girls I had been with accepted that in me and let me control them and what we did during sex. Outside of sex, in public, I was always a gentleman, holding doors for them, complimenting them, etc. But when having sex, I liked being in control. I just didn’t know there was a term for it and that I was a Dom of sorts. But more to come on that later but I was lucky that Lynn was submissive and wasn’t afraid to tell me. Because of that, as she spoke, I didn’t mind just reaching over and playing with her tits. I noticed that as I played with her nipples she definitely reacted to it by closing her eyes and breathing heavy. She still had her hand on my cock but instead of stroking it, her hand just laid there holding it as she enjoyed me playing with her nipples. She was sitting right next to me so that I could alternate between her nipples but then I settled on her right nipple and kept playing with it. I was rubbing it when she told me that she liked having them pulled, pinched, and twisted. So I did. I started to talk dirty to her about her tits, what I wanted to do to them, how I never tit fucked tits this big but wanted to. She got very excited and this went on for about 30 minutes when suddenly she came. I didn’t even know that women could cum from just nipple play. Maybe not all can but she did. I was shocked, surprised but impressed with myself that I could do that for her. I was 21 and full of ego and immaturity but she appreciated that about me. Apparently, it wasn’t the first time a guy got her off through nipple play so there goes my being impressed and deflated ego. Hahahahaha Oh well, it was still fun, I did get her off and I also learned something about foreplay and paying attention to the whole woman and not just her pussy. At that point she realized that she was still gripping my cock and she started to stroke it. She suggested that I pull off the road somewhere so she could “take care of my problem.” I told her that I didn’t consider it a problem at all but I would be more than happy to have her take care of it and so I could have more room in my pants. I found an exit and pulled off the highway, made a couple of turns and found a tree lined side street of private houses. I pulled under one of the trees where it was particularly dark and I pulled my pants down. My cock sprang out immediately and she started to stroke me again. We didn’t say much to each other and I wasn’t sure what she was going to do next. Was she just going to jerk me off or blow me? I remember her looking at me, my hand reaching out to her tits and massaging them as she lowered her head towards my cock. The next thing I knew I could feel her tongue licking me. It felt so fucking good!!! She’s stroking me, licking my cock, one hand was playing with my balls and I have this 46 yo woman going down on me. Life is good. She stopped licking me and closed her lips over my cock. She slowly slid her mouth down my cock and up again. She was awesome. I’ve had blow jobs before but this was special. She was very slow and methodical at first. She would take me all the way down to my balls but that alone wasn’t a great feat since I was only 5 ½ to 6 inches in length when I was very hard. But still, she took all of me. This went on for a few minutes before she took my cock out of her mouth, she looked at me and said that she wanted me to cum in her mouth. With that said, she went down on me again and picked up the pace. This time it went from being a slow, methodical blow job, she was really sucking me off hard. Her head moved faster and faster. I started to move my hips and thrust upwards into her mouth faster and harder. I took my free hand and placed it on the back of her head when I could feel that I was about to blow my load. My other hand was squeezing her tits hard, my hand pushing her head down further as my hips thrust my cock deeper into her throat. I finally couldn’t hold back anymore and blew my load right down her throat. I kept fucking her mouth as spurt after spurt of my cum came spewing out of me until I finally emptied my balls. She was awesome and she swallowed every bit of it. I finally stopped cumming and she kept me in her mouth until I went completely soft, licking me gently before tucking me away. It was truly unbelievable. She asked me if any of my girlfriends that let me cum in their mouths would kiss me afterwards and I said no. She asked me if I had an issue with kissing her after I came in her mouth and I said no. How could I? She just used her mouth to suck me off and swallow my load. It just seemed wrong to not kiss her, so I did. It was a long, tongue in mouth, passionate kiss. I could taste myself slightly in her mouth but it was worth it. I wanted to make sure that she would blow me again so whatever it took. I was a willing student. We finished our kissing and she said it was getting late so I needed to get her home. So I drove her home and, boy did I drive her home, twice before the night was over but I’ll continue that in my next posted story. I know this was a long story and I apologize for that but I wanted to give sufficient background information. I’ve had a very active life of varied sexual activity and I have enjoyed it all. I hope you have enjoyed my story. Thanks for reading it. |
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