It’s almost every teenage guys dream to sleep with an older woman and I was lucky enough to experience it. My mom has a friend (we’ll call V). V wasn’t too attractive but she also wasn’t unattractive. V had recently been divorced and would come over to our house a lot more. My mom would always force me to greet and chat with guests so I did as I was told. In the span of like 2 weeks, I began to see V as a friend rather than just a guest.
V and I began to talk more and more and would even talk on the phone or messages. We would talk pretty normal like “how was your day” and “what did you do today” and this happened for a good while. One day, V stopped by the house to leave a few things for my mom. I was home alone at the time. I invited her inside and we had a normal conversation until she told me “you’re really handsome for your age”. I was your typical teenager so I blushed and thanked her.
When she left, I thought that what happened was so weird. But later that night, we messaged each other but she would ask some personal questions like “do you think I’m beautiful” she even asked me if I ever thought about her. I told her yes and she said that she would think about me too. I remember that she sent a pic of her laying down. She was showing a lot of cleavage in the pic and I am not ashamed to admit that I masturbated to that pic.
The next day she came by the house again and asked if my mom was home. Which was weird because she usually knew when she was home. She asked me if I liked the pic and if it had caught my attention. I told her yes and that she was very beautiful. She asked more questions that were more intimate. What left me speechless was when she asked me if I would sleep with her. Being the nervous teen that I was, I sat there silent until I let out a “yes”. I still to this day, remember her exact words were “so are we going to do this or are you just going to sit there and stare”.
She asked me if anyone was home. When I assured her that we were alone, she grabbed my bulge and said that this was what she needs. So I led her to my room where we were kissing and touching. We both started to strip until we were both completely naked. She told me to lay on my bed because she was going to show me how to “make her feel young again”. We were in cowgirl the entire time. We were going slow and I enjoyed every second of it. I finally got to see and touch her tits after dreaming about seeing them for the longest time. When I finally came, she pulled me out and stroked me until I came in her hand. I probably lasted about 5 minutes but I still enjoyed all of it. I was super embarrassed that I lasted so little, though. But V made me feel better when she told me that it wasn’t a big deal. She said that she enjoyed it and that next time I would last longer she even have a wink. When she left I literally thought I was dreaming especially because I got to finally see her tits.
Source: reddit.com/r/gonewildstories/comments/odbgga/my_moms_friend_mf
Damn man, that’s such a hot story. You lived the dream we all had as teens.