True story. When I was 19, I lost my virginity to my girlfriend's mother, Mrs Parks. My girlfriend, Sherry, was also a teenager, one year younger than me, and we had not had sex but had been a little sexual. She let me feel her pearly-white boobs a few times, pinching her tiny nipples to see them shrink and stick out as they got hard. She also let me suck on them. Once when she was over at my house late on a Friday night, we were watching the downstairs TV from the couch while my parents slept in their downstairs bedroom. I was seated and Sherry had her head in my lap as I stroked her long red hair. Soon I noticed she was asleep. I instinctively slipped my hand down her shirt to feel her boobs again. That was nice, cupping them and squeezing them; pinching her nipples again to feel them get hard. Then I noticed her loose-fitting shorts only had an elastic band holding them on and her shirt wasn't covering it, but showing some bare abdomen and her belly button. My heart started racing as I thought about slipping my hand down her shorts and feeling her pussy. I had never felt a pussy before. My heart pounded so loudly I could hear it in my ears.
I glanced around the room, then carefully laid my hand on Sherry's shorts right over her pussy and watched to see if she moved. She lay there still and asleep. My heart was beating harder and louder in my ears. So I eased my fingers under her waistband and under her panties and immediately found her curly pussy-hair. I was so excited I was shaking. I felt her soft hairy mound for a few minutes, then moved down her mound and slipped a finger between her pussy lips down into her pussy cleft to eventually find a warm wet opening. I played with her clit, lightly rubbing and pinching it, and moving my fingers in a circle around it. When I did this, it swelled up twice its size. It was huge! I pinched it a little more, moving my finger and thumb up and down its "shaft." It was like a little dick! This was all unexplored territory for me. Then I pushed my finger as deep into her warm wet pussy as I could. "WOW!" I thought. I felt like I was going to explode my heart was racing so fast and I was shaking so hard. I had been watching her face for signs that she might wake up, and just then I saw her smile. SHE HAD BEEN AWAKE THE WHOLE TIME! So I began to slowly move my finger in and out, finger-fucking her, rubbing against that spongy spot on her anterior vaginal wall (later I would learn this is called the G-spot). She let out soft moans when I did that. She let me keep my finger in her for the rest of the movie. When it was over and I pulled it out, it got her panties soaking wet. But that was the closest we got to having sex.
Her mom, Mrs Parks, was a divorced single-mom of three girls (Sherry was the middle one). During the summers, I would mow lawns in our neighborhood for spending money and Mrs Parks was one of my regular customers. I liked cutting her yard because she had a pool in the back and would let me take a dip to cool off when I was done. I would take my shirt and shoes off and jump in wearing only my shorts. If Sherry was there, she would usually join me and we'd play Marco Polo. Her bikini was a little big for her and it was amazing how many times I just happened to grab a boob when I was "it" and was feeling around for her with my eyes closed. And somehow she would always manage to grab my dick through my shorts when she was "it" reaching out for me with her eyes closed. We had lots of fun that way.
Speaking of swim suits, one time Sherry invited me to join her and her mom and sisters at their beach house on Galveston Island. I rode there with them. My aunt who lived nearby in Freeport picked me up and took me home at the end of the day because Sherry's family was spending the night there at the beach house. When it came time to leave, Sherry walked down with me to say goodbye (the beach house was on stilts because it was on the beachfront). When we saw my aunt's car in the distance heading toward us, we stopped talking and kissed goodbye before my aunt drove up. To my surprise, and delight, Sherry pushed her tits hard against my chest and thrust her tongue into my mouth, sucking my tongue into her mouth. We had never done this before and we must have sucked face for several minutes before my aunt drove up. I couldn't help but get a huge hard-on. I wore a skimpy Speedo suit back when they were popular and it was so low-cut that the top of my pubes occasionally showed. There was no room for a hard-on. I tried to keep my dick pointed to the side and covered by my suit, but I couldn't. My boner stuck up four inches above my swimsuit. And although I'm probably only slightly above average in length, I'm pretty wide -- almost seven inches around. So it was hard to miss.
Sherry pleasantly squealed when I pushed it hard against her. My aunt soon drove up and I realized I had to get into the car without her seeing this huge dick sticking out of my suit. So I continued to look at Sherry and say goodbye as I walked backwards to the car, with my back to my aunt, all the way to the backseat door. Sherry didn't take her eyes off my dick. It was the first time she had seen it and later she would tell me that she was amazed at how big it was. Just before turning around and opening the car door I looked up to the balcony. There was Sherry's mom looking down at me silently staring at my big fat dick. I froze in horror when I realized that she had probably watched the whole thing. Mrs Parks didn't make eye contact with me the entire time; she just continued to stare at my massive hard-on. I managed to get into the car without my aunt seeing it and we drove off. I wondered what Mrs Parks was going to do.