I was 18, and just moved out of the house to live with some friends in an apartment. I always biked or jogged in the morning, and I'd run into a lady who was in her late 30's, that lived in the complex as well. A lot of friendly banter would occur between us. I learned she was a single mom and whatnot. Within a few weeks of this it became flirty banter, including her feeling my arm and asking me to flex for her. I did thinking it was funny. She then asked if I would help her move stuff from her apartment to her storage shed. I was being nice and did so. In her bedroom, she had a box on the bed and I reached to grab it and noticed the contents... sex toys and condoms. She told me that was supposed to go under the bed, and she was embarrassed it was out. She started to make jokes about it though, even saying, "I thought of you last time I used that one..." *pointing at the long glass one.* Then she was all serious and asked me, "When's the last time you've touched a girl's box? You're not a virgin, are you?" I was caught a little off guard, I told her I wasn't a virgin and that it had been a few months. She laughed and said, "I wish I could say a few months, I haven't had sex in like two years." Next thing I know she grabbed a handful of condoms from the box of toys and then pulled her shirt off. "Let's end our dry spells." and citing the look on my face, ( I was surprised to see she had nice tits) she informed me she was a 34 DD. She got on her knees and dropped my shorts to the floor. "I love that you're already up! Last longer than five minutes and I'll marry you!" She joked. She started to lick and suck my dick. After a minute though she slid a condom over and said, "Who am I kidding, I want this in my pussy." I threw her on the bed and started to gently fuck her. She demanded I go harder and faster, but I was honestly too nervous because I didn't want to cum. I did start to speed up though, and she asked if I was trying not to cum or something. "Don't worry if you cum, you're young, you'll get it up again in no time." She started to place her legs over my shoulders and started rubbing her clit. I was pounding her as hard as I could at that point and she was moaning and yelling, "YOU ARE A GREAT FUCK BABY! DON'T STOP!" She pushed me off and I ended up at the edge of the bed, she got on me a rode away. She shuddered and moaned a few minutes later, I asked if she came, and she nodded yes. "You. Fuck me doggy style until you cum. Now!" she ordered. So I did. Afterward we would hang out a little and went back to our friendlier ways.

Much later on I started hanging out with a female friend from my old high school. We started dating, and she wanted me to meet her family. Too my surprise, I learned that I already knew her mom!