Kelly's Diary 006 - Doing It on the School Swing Set - Cover

Kelly's Diary 006 - Doing It on the School Swing Set

Copyright© 2024 by Kelly85

Chapter 1: Bike Riding

Coming of Age Sex Story: Chapter 1: Bike Riding - The sixteen year-old brother of my best friend and recipient of my first blowjob on our first date when I was fourteen, Steve had a reputation or preferring girls with big boobs. This meant if I was going to keep him I needed to use every weapon in my arsenal. Soon I gave him my virginity and once started I wanted sex as often as he'd do me - which was VERY often. Steve was a busy boy trying to keep up with the demands of my newly released sexuality. Somehow I don't think he was complaining!

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   True Story  

One day Steve and I were out riding our bikes near dusk so we started heading towards my house. I noticed he preferred to ride behind me, no doubt in part because I was wearing my favorite cutoffs for bike riding with him. Taking a pair that I’d already outgrown, I’d ripped them so high I didn’t dare wear them into a store or most public places as I would’ve probably been asked to leave for indecent exposure! Then again, it’s amazing what you can get away with when you’re a fourteen year-old girl.

Although there’s probably no need to explain in depth why Steve loved me to wear this particular pair of shorts when we went bike riding, I will say that they put most of my butt on display, especially when I leaned way forward on a steep hill. Of course I never wore panties under them because I loved to tease Steve when I sat down by spreading my legs just wide enough for him to get a glimpse of my fuzzy brown pubic hair peeking out the sides. While he’s seen my pussy plenty of times without any obstruction, he seemed to be even more turned on when it was like he was seeing something he shouldn’t. It was nothing that every stripper didn’t already know but quite the revelation for me.

Besides the short shorts I was wearing my favorite black stretch tube halter. As small as my boobs were it didn’t have to be very wide so it was almost more like a headband stretched around my chest to keep my nipples covered. I liked this particular one especially because it was thin enough to allow my nipples to poke through. Best of all it was could easily be pulled up or down to get out of the way while just as easy to get back in place in a hurry if needed. In other words ... the perfect top for an occasional flash. For better or worse I didn’t wear a bra (technically it would have been impossible anyways) although sometimes on dates I wore one just to give my new boyfriend something to play with ... giving him something to do he “shouldn’t”.

Along the way we were forced to stop and wait to cross a busy four-lane highway. The subdivision road we were on was barely two lanes with little traffic so a stoplight wasn’t apparently deemed necessary. Well, whoever made THAT stupid decision should be sentenced to cross this road every day! As usual, the traffic on the four-lane was terrible this time of day and without a stoplight it was looking like it would be a bit before we had an opportunity to hurry across. Steve, never one to pass up an opportunity of his own, took a quick glance around. Seeing nobody nearby he pulled up right next to me and the next thing I knew I felt his hand slide between my barely covered butt and the bike seat. Never one to be intimidated by his fumbling moves, I couldn’t help but wiggle a little in response to his hand as he started running his finger along my crotch.

“Steve! People can see us you horny jerk!” I said, pretending to be annoyed while secretly turned on.

Steve knew by now that his new girlfriend loved it when he touched her “inappropriately” no matter where we were. In fact, I thought it was fun when we fooled around in public and people would stare at us as if they simply couldn’t believe what we were doing. Some, especially the older women, would frown and shake their heads in disgust but most of the guys didn’t seem to mind the show. I imagined more than a few went home with bruises on their sides from their wives’ stiletto elbows when they were busted for looking at us! Although my mom wasn’t exactly thrilled by my new thirst for erotic PDA (Public Displays of Affection), she knew better than to tell me to stop as all that would do is encourage me do it all the more!

“Who cares?” he replied with a grin, using his free hand to motion at the constant flow of traffic in front of us, “Just a bunch of horny guys heading home from work. Besides, they’re going sixty miles an hour. Even if they do see us, why not give ‘em something to think about?”

I shook my head in mock despair but at the same time I wasn’t exactly doing anything to discourage him from groping me. As they say, actions speak louder than words! If anything I leaned even further forward and lifted myself off the seat just enough to make it easier for him to feel me up. My little movements didn’t go unnoticed as Steve responded by slipping his hand even further under my butt, cupping my crotch as his fingers pressed against my pussy. Just as I started to wonder just how far he was would go I got my answer when one of his fingers started working its way under the crotch of my shorts. As tight as they were pulling into me I was a bit surprised when I felt it sliding into my pussy! Being I was pretty wet already just from the anticipation, he slid easily up inside of me. It was only just up to his first knuckle or so but more than enough for me to feel it in me.

“Steve!” I exclaimed, genuinely a little concerned now, “C’mon, you can’t do THAT! Besides, there’s someone behind us now!”

Indeed, he may not have noticed with his fixation on my fourteen year-old butt but a huge black SUV had just appeared behind us. One of those land yachts that never see an off-road route yet their owners want to show off their good fortunes.

“So what? Besides, you know as well as I do you love it you little slut!” Steve said as he pushed his finger even further up into me. “Hmmm, somebody’s horny!” he laughed as he felt the wetness of my pussy on his finger.

Yes, I WAS horny but there was still that big black SUV which had moved up until it was right behind us. Glancing back I could see that inside was the stereotypical soccer mom with a standard issue two kids and even the family dog. Both of the kids looked to be middle school or so. Well mom, it’s never too early for them to learn about the facts of life! In reality, it wasn’t likely that the kids even noticed what Steve was doing to me and even if they did, to them it probably looked like he just had his hand under my ass.

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