A little about me. I have been in a lousy, sexless marriage for several years. Without explaining too much, I decided I'd start looking for a woman, my age that perhaps was in the same situation as me, and wanted a friend with benefits on the side. I signed up on one of those affair websites and started looking around. At my age, I was not interested in finding some bimbo who was in bed with anyone who paid attention to her but rather a regular woman next door type that just wanted a friend and to get her freak on once in a while. After numerous chats and a few dates, I stumbled upon the woman who I would describe as a hot Grandma. Now she wasn't old and gray, but blonde and well put together. She was a retired teacher, early 60's who was bored with her husband in bed. She still had a high sex drive, and he pretty much lost interest and she was unsatisfied. Apparently she had a FWB who traveled to her area for business who she was seeing. He had been transferred so her arrangement with him was over. She was looking for his replacement.
The thing about her was she was deathly afraid of STD's. She made no bones about it, if we progressed to where we would have sex, I would have to be tested. I explained to her that I had only been with my wife and the last time was years ago. Didn't matter, she wanted me tested. So I said if we get to that point, I agreed to see my doctor. We had met a few times for lunch. Nothing sexual, just a lunch date. We sat and talked and had a nice casual time. We had discussed sex and our sex lives or lack thereof, exchanged some things that turned us on. In person, nothing too hot. Via text, it was more personal and more sexual which generally happens. We had gotten to the point where she was making it known she had interest in me in a sexual way so I knew the STD test issue was around the corner.
One afternoon, we met for lunch. She had afternoons to herself most days since her husband worked, she was retired and she babysat her grandchildren, which by the way I found hot that an attractive Grandma would sneak out to meet me then go babysit her grandchildren.
We went to a nice place and had a nice lunch. I noticed she sat closer to me, and she touched me on my arm a few times. Played footsie with me under the table a little. I definitely got the vibe she was attracted to me and probably a little horny. We walked out of the restaurant and she said she had some time and asked if we could go somewhere to sit and talk. She got in my car and we drove to a nearby park that she found on her phone. I parked the car and we were just talking, having a nice time. I leaned against the driver's door to face her, and I guess my legs were spread a little. I noticed she was looking at my crotch a little. I was wearing khakis and I guess my bulge was showing and she liked the view. At some point, I rested my hand on my lap and she now wasn't sneaking peeks, she was staring. He eyes lit up and I could tell that she liked what she was seeing. I gave her a smirky smile and she said keep going then stared at my crotch. Now I had let women watch me before and I have to say, it can be very sexy and hot and a turn on when a woman watches and gets turned on by what I'm doing. I figured if this was a kink of hers, I'd give her what she wanted and tease her to see how turned on she'd get. So I slowly started running my hands on myself. My thighs, upper thighs, inside om my thighs. This along with her staring and squirming made me hard, which I have no trouble getting hard in the first place. She was mesmerized. She said she never had a guy do this for her and she was always afraid to ask. But she did watch men jerking off porn which she masturbated too. She told me to rub my cock over my pants which I started doing for her. I leaned back and spread my legs and was teasing my cock over my pants. You could see the outline of my hard cock clearly in my pants.
She was now sitting up and stirring. She started to rub her tits over her shirt telling me she loved this and she was wet. She had nice boobs, big C cup and I told her to pull down her shirt so I could see them which she did. Now I was rubbing my cock and the dirty talk was on. I asked her how much she liked me playing with my cock for her and she was loving it, telling me she was so hot and soaking wet. She was now kneeling on the front seat and rocking back and forth putting pressure on her clit with her jeans. I started to drip and now there was a wet spot on my pants. When she saw this, she blurted out, take your pants off and stroke your cock for me. I didn't have to be told twice, but I took them off slowly making sure to tease her. First my belt, then my button, the the zipper. I was so turned on from her staring and watching and seeing how hot this made her, I wanted it to last as long as possible. I slowly slid my pants off and left my boxer briefs on. MY cock was so hard my head was showing through the waistband. She said, take them off so I slipped them off. I was sitting naked with a hard cock and she was going crazy at the view. I started rubbing my cock, running my fingers up and down my shaft. Precum was flowing and I was rubbing it all over my cock. When I wrapped my hand around it, she said, "That's it baby, stroke that big dick for me." I was now stroking and jerking. I started humping and ricking my hips like I was fucking my hand. She was totally turned on.
She was telling me how much she loved how I stroke my cock, how much she loved my cock, how wet her pussy was. She lifted her shirt, pulled her tits out and was squeezing and twisting her nipples. She was rocking back and forth while her eyes were glued to me and my cock. She was now telling me what to do. Faster, slower, show her my precum. She told me to squeeze my cock hard and make it drip. I was dripping precum at this point, so I made sure there was some on my finger and I sucked it off. At that point she moaned loud, shoved her hand down her pants and came. She was staring and shuddering and had an intense orgasm. When she started cumming, I started stroking hard and fast. She was telling me to stroke it faster and she wanted to see me shoot hot cum. I told her I was close, she said cum on yourself. I want to see your cum. I exploded. I shot ropes of cum all over myself. ON my stomach, down my cock, it ran down my balls. It was a long hard orgasm. As I was cumming, she was still fingering her pussy and she came again. Catching our breath, I rubbed my cum all over myself gaining my composure. Her eyes were fixed to me, my cock and my cum.
After we buttoned up, she said that was the hottest thing she ever did and thanked me. She said she had always wanted to do that and wanted to do it more, which we did do and I'll share if anyone is interested.
Moral of the story, it was so hot that a hot older woman wanted to get kinky masturbating that it totally turned me on. I've always said, if you're going to masturbate, it's better with someone that alone. It didn't work out with her, but we did play around several times after this.
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