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Older woman
I did some work for this woman who is in her sixties, she started really complimenting me a lot and made me a lunch everyday. I was not uncomfortable or anything and took it all as she was just looking for someone to talk to a lot. I finished up the work and then got a call from her a few days later asking me if I could come by her house when I finished up. She was a little vague about what she wanted but I went by her house later that afternoon.
After some talking about a few things she looked at me and told me that she was really nervous to ask me something. I just looked at her and said well just ask me, there cannot be something so embarrassing around her house for me to fix.
She finally came out with it and I just stood there for a second thinking, well I was wrong and there was nothing to fix. She asked me completely outright if I would have sex with her because she thought I was completely handsome and she really trusted me.
I was in my late thirties at that time and she was easily twenty five years older than me but all in all not in to bad of shape and she also had some pretty large boobs which is a big turn on for me. I told her I needed some clarification because there was no way I wanted a relationship with anyone at that time and I was surely not going to date a woman that much older than me. She told me she just wanted it to be sex and if I enjoyed it maybe a continuing thing where I just come over now and then and have sex. Now I have never met a woman who just wanted sex and I have also never turned down sex with any woman. I told if she could do this without attachment besides just being friends then I was okay with it, knowing fully that this would never work but maybe I would get a blow job out of it.
Well a few years later I am still going by her house at least every month and sometimes she sends me messages weekly asking if I have time to stop by after work. She sucks cock great, I could not ask for better and she really seems to love doing it. I have shown up at her house right from a job site and she will just have me drop my pants and she goes right to licking and sucking it.
It also turned out that her boobs are awesome, nice large nipples that get quite erect and are fun to lick and suck on, they are a bit saggy but she had this half cupped bra that she put on and it is amazing how great they look in it. She is not always up for intercourse but when she is her pussy is tight and grips my cock nicely, most of the time we have to use lube to do it but once I have gone in and out a few times she is good to go.
So not sure how long this is going to last but I saw this site and figured I would tell my story.
I did some work for a single female friend (Anne), actually fitting a gate post, and her mother (May) was there at the time. I was in my mid 40s and separated and I would guess that the May was mid 60s. May asked if I could stop by and do some jobs for her, which she said that she would pay. I told her that I would drop by one evening later in the week. A few days later I called May and arranged a time to visit that evening, I also told Anne that I was going and she responded by laughing and telling me to have fun. I arrived at the house and the job was to free a sticking door lock. A quick blast of WD40 and all was well, about 5 minutes. May asked how much and I said it's OK, a simple job, no expense so no payment needed. I was persuaded to stay for a coffee and a chat which lead to staying longer than I intended and we eventually ended up kissing which of course lead to sex. She had a good body for her age but was surprisingly passive during sex. I thought that she had not enjoyed it but a few days later I got a call from her to visit again as she had more jobs for me. This in turn led to more sex so I couldn't have been that bad! As for Anne, she obviously knew what was going on from talking to her mother and although never mentioned it directly to me made approving comments. The handyman sex continued for over a year.
My wife and I were good friends with an older couple about the same age. I ended up doing a few renovation jobs at their home. The wife was a beautiful woman. We were over to their house for dinner quite a bit and she was always flirting with me saying that her and her husband sleep separately etc. I never thought it would go to the next level.
One afternoon, I was working on a kitchen renovation at their house and they were planning a barbeque afterwards. The husband said that he was going to the grocery store and would be back in about an hour. I don't think he was down the road a mile when the wife said that she wanted to show me something in the basement. Once there, she hugged me and said that it's been so long since she's sucked a cock, and she's wanted to suck my cock but never had the chance. I told her that her husband just left. She quickly undid my jeans and kneeled down, commenting that I was much bigger than her husband's cock. I was nervous but she first kissed the head and then licked my balls and asked me if I liked that. Then she took my cock and started sucking with a wrist twisting technique that drove me crazy. It wasn't long before I told her I was going to cum. She paused for a second and said "I want to taste it".
I shot an unmistakably generous load in her mouth and she swallowed. When she got up she kissed me as I noticed a little cum in the corner of her mouth.
I worked at their house for about a year before they sold it and moved to Florida. If her husband and my wife only knew that she sucked my cock all over that house!
I'm 63 and I still like fucking older women !