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First time with an old lady
My first time was with a senior citizen. When I was in high school, I mowed lawns to make money. There was a lady who lived down the street whose husband had died a few years before. They were always nice to the kids in the neighborhood and would let us play in their big yard and gave us candy. I started mowing that yard after he died.
She would always invite me in to pay me and give me a drink and snack. She had a lot of pictures around the house, which I like looking at. I would ask a lot of questions about them, partly because I was genuinely interested, and also because I knew it made her happy to have someone to talk to. One day she went and got a shoebox of pictures figuring I would want to see more. I admit I wasn't quite THAT interested, but I was willing to humor her. We sat and looked at the pictures for a little while, and as we got near the end, there was one of her as a much younger woman, naked.
She acted embarrassed and surprised that it was in there, but she didn't pull it away. She said something like, "Can you believe I used to look like this?" I was mortified and couldn't answer. She apologized and said that's supposed to be in a different box, but that's not for me to see. I laughed nervously and said, "Maybe next time." I was joking to break the awkward tension, but she asked if I really wanted to see it. I said, "OK".
She left and came back with a different shoebox. It had dozens of nude or sexy photos that spanned many years, right up until the year her husband died. She said, "I suppose I shouldn't let you see these recent ones since it's like seeing me naked now. You probably don't want to see an old lady's pussy." I hadn't really reacted much until this point because the whole situation was surreal, but I responded, "I don't mind."
She stood up in front of me and took off her clothes. Her tits were less saggy than I would have expected, and she pressed them in my face. She told me stand up. As I did, she put her hands on my hips and worked them down my shorts and underwear, sliding them down to my ankles. She slid her hands back up and started stroking my cock. She put her lips around it and could probably tell I would cum very quickly, so she sat back down on the couch, spreading her legs and rubbing herself. She had me kneel down and directed my dick into her pussy. I did cum very quickly, but so did she. We had sex several times that summer, and I eventually got better. She even taught me how to eat pussy. For Christmas she gave me the shoebox. The following year she became ill and went to live with her daughter out of state. We sent cards to each other at holidays, but I never saw her again.
When I was 18 I had sex with my grandma who was 63. She and me had always been close. After Grandpa died she got lonely and I’d visit her 2 or 3 times a week. She seduced. I admit it was awkward at first but it became intense. We carried on for 3 years. It ended when my Mom caught us having sex. She went ballistic and made all kinds of threats.
I actually got my first blowjob from an older woman when I was 17 years old.
She was a retired school teacher probably in her late 60s who lived alone. I use to mow her lawn and shovel her driveway. I was driving my parents car to and from her house on weekends.
After one snowstorm, I went to shovel the driveway. After I was finished, I would always go inside and she paid me. She offered me a hot chocolate and I accepted. We sat and talked for a while as she told me about her life. As I was getting ready to leave and put my jacket on, she gave me a kiss and said "if you promise not to tell anyone I will make you feel better". Hesitantly, I said "sure" but I didn't know what she meant until she kneeled down and started to unzip my snow pants. She carefully pulled down my underwear and now my cock was right in her face. She commented that I was bigger than her husband as gently kissed the head. Slowly she started to lick all around my head as she held my balls in her hand. It felt so amazing. Then I watched her as she sucked my cock taking it all the way down her throat. She had a hand wrist technique that I knew it wouldn't be long. When I told her I was going to cum she increased the speed. I shot an unmistakably huge amount of cum into her mouth and she savored it.
I got dressed and she told me not to tell anyone. I drove away saying to myself that I just got my first blowjob. Every snowstorm I was there and she would get more daring. She would show me her tits and get me all hard then pull me into the living room and suck my cock.
During the summer months when I was working in the yard, she would come out with lemonade for me. Couple of times I even showered there.
I ended up fucking her a couple of times before I left for college. When I was home on break one semester, I noticed a for sale sign in her yard and never saw her again. I heard that she moved to Florida. Thank you for the memories!
How old was she?
That is a wonderful story