Teenage and the woman nextdoor
When I was 17 and still living at home, this middle aged woman moved in nextdoor to my parents. She had recently divorced and was looking for a new start in our town.
My parents introduced themselves and they tried to introduce me, but I wasn't interested in meeting the neighbor lady. This is until I finally noticed her and realized she was kind of hot.
A few weeks later, I noticed that my bedroom was on the side of the house where it was facing her bedroom. I thought I was in luck and would get to see her naked. I waited and watched, but no luck.
Then one night I noticed her in her room, not sure what she was doing, but the light was on and I could see her sitting there. I think she was reading, but I couldn't say for sure. So I turned on the lights, and figured if she wouldn't give me a show, I would give her one.
I stripped all my clothes off and walked around the room naked, acting like I was looking for someone. She must have noticed, because after I walked around for a few minutes, I noticed her light go out. That's when I sat on the bed and began to jackoff. I shot my load into a towel and cleaned up before going to bed.
I started doing this every night whenever I noticed her light on. I'd flip on the lights, jump on the bed and start jacking off. Several times I noticed her look my way, and then get up to turn the lights off. I couldn't be sure if she was turning off the lights because she was leaving the room in disgust, or if she was doing it to get a better view.
Then one day she stopped me in the backyard and made a slight comment about maybe getting a shade for my room. I acted like I had no idea what she was talking about. That's when she came closer and whispered that she had saw me several times in my room.
I acted like I was so embarrassed and asked her if she was disgusting by it. She said she wasn't, but maybe it's something I should keep private. I commented that maybe I wouldn't have to do that's if I had a beautiful woman such as her to help me out. She didn't say yes, but she also didn't say no. She just walked away.
A few nights later, I was in my bedroom again, and I seen her light come on. This time I made it a point to wave at her. She noticed and waved back. I pulled down my pants and started jacking off. She left the light on this time and watched me the whole time. After I finished, I wave at her again. To which she waved back, and then I turned out the lights.
The next night was a repeat performance with me jacking off again. Again she waved and we turned out the lights. This went on for about a week until I noticed as I was jacking off, she slid her hand down her pants, and lifted her shirt up to expose her breasts. She rubbed her tits with one hand while rubbing her pussy under her pants with the other.
A few days later, I saw her in the backyard, and she winked at me. I knew I was getting close. Just had to keep playing my cards right. By the following week, she and I had a regular schedule of masterbating together. Both of us were fully nude on our beds, facing the window with our lights on. This went on for about two months.
I was nearing graduation and already turned 18. I was so ready to fuck the neighbor lady, but was happy with the current agreement and didn't want to jeopardize that, so I never pushed for anything more.
The day after my highschool graduation and party, I was opening all the cards and gifts. I came across a card from my neighbor lady, and it simply said. "I know you were already a man, but now you're legally a man". She went on to say she would give me a gift later on, and signed it with a wink.
My parents had a vacation planned for mud June. They left me alone and went on their way. That night I was waiting in my bedroom for the neighbor lady. It was nearing 15 minutes after midnight, and she still hadn't turned in her light. My mind was racing, wondering if I had done something to piss her off. That's when I heard the phone ring.
I got up and slipped on some shorts before answering the phone. It was the neighbor lady saying she was coming over, and I should let her in the back door. I ran down stairs and met her just as she was getting to the door. I invited her in and back upstairs to my room.
She was wearing a silk white robe with nothing else. As we got to my room, she whispered that she hopes I like my graduation gift. And with that, she let her robe open to expose her naked body. She reached down and pushed my boxers down to the floor. Then she pushed me on the bed and began sucking my dick.
I had a girlfriend who tried to suck me once before, but she was nothing compared to what I was receiving this night. She sucked my dick and massaged my balls until I had to make her stop. I was about to finish.
That's when she got on top of me and started rubbing her pussy on my dick. I told her maybe I should grab a condom from my bag, but she said no need as she slid her wet pussy down on my hard dick. I thought I was going to explode right then. Not that I had lots of sex before then, but what I did have with my girlfriend, was always with a condom. So this was skin on skin action, and it felt a 100 times more amazing.
She rode me slow and deep, grinding her pussy on me whileI was feeling and sucking on her tits. It was amazing and loved every second of it.
She and I would have sex several more times that summer before I went away to college. Unfortunately she moved away while I was in college, and I never saw her again.
I stalked her onetime on Facebook after it became big, and found out she was married. Still didn't have any kids, so I'm assuming she can't have any. But she lives in New York with some fancy doctor now.
I thought about sending her a friend request, but figured she would just decline me. I still have my memories. But that was one hell of a summer, and I will never forget her.