Tender High School [M]oments | 2016

So this may be a little bit different, and to make a point, none of these are involving sex. I want to talk about a few moments while I was still in high school where I had some very sexy moments with past girlfriends.

I guess this is the part where I describe myself. I was a 16 year old sophomore in high school and had not gotten a lot of experience with girls at the time. I was an average scrawny geeky guy, but with stylish hair that I would often get compliments for from people.

My first bits of stories are with a friend named Diana. Now, I had known Diana for since I was about 8 years old. We grew up in a neighboring area and had frequently spent time together along with some other friends.

Over the years, we had hung out less and soon did not hang out at all, but as we reached our high school years, Diana became a bit of a wild girl. I remember hearing stories about her having sex with her boyfriend at the time, which slowly developed a slight jealousy in my virgin sophomore mind. Images of her in different sex positions ran through my head all the way down to my throbbing cock each and every time I saw her in school.

Diana had a slightly thicker body, the kind that fills a nice pair of jeans. Her breasts were a typical C and she sometimes wore shirts that gave just enough to imagine the rest of them.

Fast forward to the period we started dating. I don't remember how it all started but the first thing that comes to mind is the sexual texts that we were immediately sharing. I remember one day, I was riding in the passenger seat of the car with my mom where we were going to get my license plate for my car. The entire trip consisted of flirting and sensual vibes which turned into straight up sexting about fucking her doggy style in one of the low traffic hallways in our school.

These texts continued into the day I visited her at her house. My dad drove me over and dropped me off in her driveway. The house didn't look too great but it wasn't a big deal to me compared to what was to come.

Diana met me at the door, waved to my dad, and then took me inside. There was a quick introduction to her mother and then it was off to her bedroom. She locks the door immediately. As an inexperienced 16 year old guy, I'm not exactly sure how to respond to this but she sits me down on the bed and asks me what I want to do. I sillily say, "let's watch a movie," only to find that it was my best idea.

She put in some new comedy that was out at the time and plopped down next to me, rolling over so that she is closed between my body and her wall. For a good half hour, we genuinely watched the movie until at some point my lips found hers. Our attention was lost from the film and more focused on deep kissing and exploring hands. I rolled myself on top of her, squeezing her tits and kissing her passionately as I feel her squirm lightly and audibly respond to my grasp. After a while, I started to grind my now-rock hard cock against her squirming pelvis and watched her eyes close and head roll back. We kept at this for a while and it was stop and go for a few more sessions.

Eventually the movie ended, and she got up to turn off the annoying repeated sounds of the DVD main menu. I gazed at her ass in the tight jeans that she was wearing that day. She was wearing a tight fit T-shirt and bra that I had quote plentifully been groping at. As she walked back to me, there was some quiet conversation between us, leading up to the big 16 year old me moment.

I watched her slowly pull her shirt over her head and toss it against the wall behind her and it lightly plopped to the floor. She stood their with her hands behind her back and I watched her bra slip off into her hands. They were perfect. At least perfect to me at the time. They were incredible handfuls as she straddled me and I squeezed them in each of my hands. This was my first time seeing a women's breasts in person and I was taking every chance I got with them. I squeezed, sucked, and bit on her nipples, feeding on her reactions. I felt her grind her body against my throbbing dick and eventually she pocked up on its presence.

She hopped off and undid my douchey Hollister belt and shimmied down my khakis cargo shorts and boxers, revealing my dick to her wandering eyes.

She slipped it into her mouth, and well, that was about it. It was terrible actually, Hahaha. She did not seem very experienced at this and just kind of held her mouth around my cock. I started off with some noise but quickly was not sure what to do as I was getting nothing from her end. She eventually pulled me out and asked of it felt good. I slyly gave her an untrue yes and put my pants back on as she was wanted by her mother.

Not too much happened after that moment. Outside of this night, we had some hot make out sessions in the hallway I had mentioned but we really only dated for about a week. We decided it got kind of weird to be dating since we had been friends or so long before.

Anyway, this was my first post here on gwstories and this ended up being longer than I expected it to be. Let me know what you think of it. I have more exciting moments from another girlfriend that I'd love to talk about if you guys enjoyed this one. Let me know!