Kelly's Diary 010 - Teasing My Boyfriend's Brother - Cover

Kelly's Diary 010 - Teasing My Boyfriend's Brother

Copyright© 2024 by Kelly85

Chapter 1: Ready to Party

Coming of Age Sex Story: Chapter 1: Ready to Party - My incredible boyfriend Steve had picked me up to take me to a party but when he forgot his wallet we needed to go back to his house. While he hunted for it I had some fun teasing his younger brother. Jim got to see more of his brother's girlfriend than ever before and before it was over I even talked Steve into putting on a little show for him!

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

Until recently Steve was just the sixteen year-old brother of one of my best friends, Sharon. For a girl like me ... an unattainable dream. Two years younger than him, with a body less developed than even many of my peers, let alone the older high school bimbos he favored, I never dreamed I would ever actually have a chance to catch him. So you can see then why this fourteen year-old soon-to-be Freshman felt so proud when this handsome Junior boy took an interest in me over all the other girls chasing him. Why he asked me out the first time I had no idea but I was determined to make sure it wasn’t the last. Fortunately, when it came to boys like him I knew exactly what he wanted.

In short, on our first date Steve was the recipient of my first blow job. I may not have been as talented as the other girls but I can’t imagine any of them being more enthusiastic, especially given I did it in the middle of a crowded movie theater. Swallowing the cum he managed to get into my mouth after spewing most of it all over my face didn’t hurt my standing either. Needless to say he asked me out on a second date!

Yet for boys like Steve, I knew blowjobs weren’t enough to keep him interested. This it wasn’t long before I’d given Steve my virginity and so far he was the only boy I’ve allowed to have sex with me - not even a stray blowjob. No doubt didn’t hurt when it came to keeping his interest focused on me was that I was just as eager as he was to do it every chance we got - I’m not THAT naïve you know. In fact, sometimes it seemed like we did it almost every day but that’s as much by his choice as mine. For a girl who’d never even kissed a boy only a few short months ago, I’d certainly come a long way!

My friend Sharon also has a younger brother but like most boys his age, Jim was unbelievably immature, especially when compared to his sexy older brother. As such I’d never paid much attention to him although I knew he was always staring at me like I was some sort of alien life form. Even so, while I pretended not to notice, what girl doesn’t like to be looked at by a boy, even a dweeb like Jim? Lately it seemed a lot of guys at school and even some fathers at church were starting to look at me the way Jim did, especially once Steve told everyone what a little slut I was becoming.

Earlier in the week Steve had promised to take me to a party. It was supposed to be one of those deals where someone’s “enlightened” parents served alcohol under the theory it was better to do it in a controlled atmosphere than having their kids go out and get in trouble. Although I didn’t really care about the drinking part, I DO love to flirt. Steve always enjoyed showing me off to his friends which turned me on as well although I never did anything more than tease them mercilessly - the more the better so far as Steve was concerned. He seemed to love seeing his friends look at me, knowing that when all was said and done HE was the one who would get to fuck me later no matter how much I teased anyone else. Besides, if I knew my new boyfriend at all there no doubt at some point we’d find somewhere private in the house to have some fun on our own. Then again, it didn’t necessarily have to be TOO private.

Checking myself out in my bedroom mirror while I waited for Steve, I smiled as I thought to myself how turned on he would be when he saw the outfit I’d picked out. To me it was the perfect party outfit - not enough to actually show anything but terribly suggestive as to what was barely concealed. The black skirt was extremely short, even by MY standards, and it barely covered my cute little butt (OK, so I’m proud of it). I’d picked it out after seeing one my friends figure skating and realized that the skirts she wore out on the ice would be perfect for flirting. Of course, I wouldn’t be wearing the heavy tights she wore to cover herself up and keep warm in a cold ice rink. Watching the mirror, I could see all I had to do was bend over just a little and it would ride up my ass, revealing the skimpy black string thong I wore underneath. Granted, normally I prefer to avoid wearing panties altogether and I especially despised thongs (think about it guys, how would you like to walk around with a wedgie all day?) Still, with a skirt as short as this one I really needed to wear SOMETHING to avoid being arrested for indecent exposure!

On top I’d chosen a skin-tight sheer white blouse through which my black lace bra was clearly visible - which is the only reason I was wearing the damn thing in the first place. I hate bras for lots of reason of which comfort is high on the list but mostly because it only served to remind me that I was still too small to really need one. A pair of black four inch strap-on heels completed the outfit along with a simple gold ankle chain - a recent gift from my father.

Turning away from the mirror I looked over my shoulder and smiled. This was my best “profile” as my boobs weren’t developing as fast as I wished. It seemed all my friends had these great boobs going and here I was still trying to justify an “A” cup (well, technically a training bra but a girl can dream). That’s why I loved wearing clothes that emphasized my butt, even if I couldn’t claim any credit for it since I didn’t work out, do sports, or anything like that. It was pure genetics to thank for granting me a tight little bottom that filled out my jeans perfectly. I loved Steve to touch it and hold it while we walked through the mall or when we were with his friends. Sometimes when nobody was looking his hands would wander and work their way between my thin legs and my pussy would tingle as I remembered the last time he’d done just that - without the jeans in the way.

With my eyes closed I sighed softly as my fingers pushed aside the thong and lightly touched my fuzzy pussy. God it had felt so good when my sexy boyfriend touched me there! Rubbing my clit slowly, I dreamed of his exploring fingers on me as they teased my clit and explored my wet pussy. Speaking of which, my pussy was already wet as I pushed my own finger up in me and I gasped as goose bumps seemed to break out all over my body. Thoughts arose of how later tonight Steve would be taking off my thong and licking me, tasting my pussy as my short pubic hair rubbed against his face. It wouldn’t be long after when he would fuck me and I’d be moaning, just as I was now after adding another finger to the ones already in me while I fantasized they were actually his hard wonderful cock as it entered me. Steve may have fucked me over at his house just the day before but that now seemed like centuries ago as I continued to masturbate.

Left to my own devices, odds were I would’ve been lying in bed before long with my thong down at my ankles while I fingered myself to a massive orgasm. Unfortunately that wasn’t going to happen as just then my mom walked in on me, interrupting my personal play time. Now I don’t mean to imply she did something bad. On the contrary, my door is ALWAYS open as I shared everything with my parents and had nothing ever to hide. In fact, she was the first person I told when Steve first fucked me! I’ve been masturbating for a few years now and undoubtedly she’s seen me do it a number of times since we first had our mother-daughter “talk” about it so many years ago. Thus I wasn’t embarrassed in the least for her to see me playing with myself although normally she didn’t make a point of interrupting me when I was doing it.

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