Kelly's Diary 027 - a Tween Sleepover - Cover

Kelly's Diary 027 - a Tween Sleepover

Copyright© 2024 by Kelly85

Chapter 1: My Tween Years

Coming of Age Sex Story: Chapter 1: My Tween Years - Obviously at the time of this entry I wasn't a "tween" in the sense of being eleven or twelve years old. Actually I'd just turned sixteen. "Tween" in this instance describes the phase of my life between when I first started having sex and when it became more than just me and the boys at school. Sleepovers were something I always loved and none were better than the ones I shared with my very best friend in the whole world - Beth.

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

As I mentioned in the summary, the term “tween” here has nothing to do with age per se. Rather it’s in reference to a period in my life between two of the most significant events in my life - the loss of my virginity and the start of my incestuous relationship with my dad. It was a time of learning, exploration and frankly a lot of fun for me. Looking back I’d also have to say it was also perhaps the most naive time of my life as well. Indeed, I’m more than a little embarrassed now when I reflect back on those days and see just how clueless I was. Most people seem to have a difficult time accepting that I could really be so unaware of what was happening around me at the time yet I would challenge those same skeptics to sit back and think about how THEY would’ve acted and what THEY would have understood had they been in the same circumstances as me.

Like my mother and many of my friends, I lost my virginity when I was fourteen to the brother of one of my best friends. It was more symbolic than biological in that my hymen had long since departed - just not to a real dick. Fresh out of middle school, at the time I was more than ready. Not only did I WANT to do it, my mom had prepared me as well because she wanted to be sure my first time wasn’t one of those horror stories many girls told me about theirs. While I can’t say she was especially anxious for me to become sexually active, at the same time she knew it was useless to try to oppose Mother Nature by pretending she could stop me. In her mind it was better to accept the inevitable and deal with it than to do what so many parents do these days and try to pretend if she ignored it then it wouldn’t happen. Seems logical yet so many parents can’t see the light - and people wonder why we have so many teen pregnancies!

Actually my mom’s dealings with my sex life were in line with my parent’s overall philosophy towards parenting. Not that they were uncaring or overly permissive. If anything at the time I would’ve said exactly the opposite as if anything their rules seemed rather restrictive to me. What I’m thankful for today, and how I plan to raise my own daughters as well, is they didn’t ignore sensitive topics that might upset me or cause them discomfort, such as me going out late with friends or even having sex. Instead, my parents addressed such issues head-on and in doing so established clear rules and boundaries. These allowed me a lot of flexibility yet at the same time set very clear expectations along with disciplinary actions if I failed to follow them.

A prime example of such flexibility was my wardrobe. True, some people might’ve considered most of my outfits a bit on the risqué side and for sure my Aunt Sheri (my dad’s youngest brother’s wife) was always making her obnoxious opinions known. Despite my Aunt’s declarations to the contrary there WERE strict rules and firm boundaries my mom set which she expected me to follow. For example, in grade school I was always required to wear panties any time I was away from home. Not that I was anxious to run out and flash people but at the same time I’ve always enjoyed the feeling of being bare under a dress or skirt. At that age it wasn’t a big deal for me anyways.

While the panties rule was inviolate, at the same time my mom never pushed me when it came to bras as I got older. Of course it wasn’t like I was blessed in the same way my best friend Beth was who was already a C cup in 7th grade! My tiny boobs were a constant source of embarrassment to me throughout most of my high school years until Mother Nature finally paid a visit during my college years. Fortunately I learned early on that guys weren’t nearly as obsessed with your boobs if you gave them other things to focus on instead! To this day I avoid bras whenever possible although when teaching they were a requirement. When going out, face it - they come in handy at times when to comes to teasing men.

LOTS of other rules and guidelines were imposed on me growing up, most of which had nothing to do with sex of course. Bed time, keeping my room clean, housework, etc. were all spelled out for me. That’s what you get when you’re the only child of a lawyer and an RN I guess. My point being was despite the heavy-handedness in some areas, my parents didn’t go overboard and dictate things to me unless they were really important. If only I had appreciated this when I was that age!

Once I started having sex with my boyfriend Steve I was hooked - I enjoyed sex. No ... make that I LOVED sex!! It’s not like I’d been unfamiliar with the concept. Heck, once I started masturbated I was addicted immediately. I guess it’s sort of funny in a way my mom actually had to set up some rules for me when it came to pleasuring myself but then when you’re young and naive you don’t always fully understand the consequences of your actions. It felt so darn good to touch myself that I was doing it all the time, including places and circumstances which were inappropriate - at least so far as my mom was concerned. Hence the rule that doing it at home or in the car was OK but otherwise not in public, or at the very minimum not where anybody could see me. Sure that seems obvious now but back then I sort of had a one-track mind when it came to my pussy!

Luckily I wasn’t the only one in my circle of friends who felt this way about her pussy. Just about all of my close friends seemed to “self-discover” about the same time as me although I don’t think they had the blessing and instruction of their moms I was fortunate to have. For sure I knew most didn’t do it around their parents which I sort of found odd in that my parents treated masturbation as just something normal that everyone does so there was no need to hide when you did it. As for those friends that didn’t start doing it on their own ... it only took a couple of sleepovers to convince them how much fun it was. So in terms of masturbation, my “tween” years, and my friends it brings up an important note. Sure we played while together but we never actually physically played WITH each other. Of course I was fully aware of what a lesbian was thanks to my dad’s extensive porn collection and video viewing habits on the TV, yet the idea of doing it with another girl wasn’t exactly something I liked to think about. When we all got together the topic was BOYS, not girls!

My sex life during this time was also what I’d categorize as being pretty standard and straight-forward. While I was faithful in terms of sexuality to my first boyfriend, unfortunately his mom was transferred to California after only about six months after we started fucking leaving me uber horny and alone. Well, THAT didn’t last long, or at least the “alone” part. I quickly discovered there were plenty of other boys at school and church who were more than ready to step into Steve’s shoes.

After going through the grief of losing my first boyfriend I wasn’t anxious to tie myself down to one guy again any time soon. I guess you could say I became a slut in that it was pretty well known that I put out on the first date. Still, at the same time that just made it easy to always HAVE a date. When I say “put out”, it’s not like I fucked them all, or even a majority. Blowjobs were my real forte at the time and I like to think I had quite a good reputation when it came to my technique. It didn’t hurt I was one of the few girls my age who enjoyed swallowing. It’s always easier to do something well when you enjoy doing it. Wow, it was amazing how fast THAT little tidbit got around! So while I blew lots of boys during my “tween” years, I think people would have been surprised to learn how few of them I actually fucked. Not that I didn’t have sex - no, I had tons of sex! I just limited the number of guys who actually got to fuck me but those that did got to do me a LOT. This was primarily due to my mom’s advice as she knew there was a fine line between being a slut and a skank.

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