Kelly's Diary 011 - Teasing My Boyfriend's Sister - Cover

Kelly's Diary 011 - Teasing My Boyfriend's Sister

Copyright© 2024 by Kelly85

Chapter 1: Luckiest Girl in the World

Coming of Age Sex Story: Chapter 1: Luckiest Girl in the World - Dating a guy exclusively can be more complicated than people might think - there's his family to deal with as well. I suppose it goes both ways but in my opinion Steve's family posed much greater challenges for me than my parents did for him. It didn't help that his younger sister was jealous I was having sex with her brother!

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

Ok, so I’m just fourteen and I’ve got no idea what the future holds but I still want to say this - I’m living in the best days of my life. Or at least so far. Yes, I’m the luckiest girl in the world! If you don’t believe me, then take a closer look at my life...

At fourteen, getting closer to fifteen now, I’m now well into my teen years and every adult I know says those were the best years of their life. Being a freshman in high school means I’m surrounded by the hot older boys instead of the immature little runts back in middle school. One of those older boys is now my boyfriend and lover but more about him in a bit...

As the only child of two professionals - a lawyer and nurse, people probably think I’m spoiled and I wouldn’t disagree with them although I WOULD disagree with their disapproval of the matter. Yes, I DO get most everything I want but sometimes I have to work for it. Mom is the strict one but daddy always gives in sooner or later. Yes, I’m definitely a daddy’s girl but then what teen daughter isn’t? It’s not like me and my mom aren’t best friends. She’s my confidante, the one I trust with my most deepest secrets. My mom pretty much knows everything about me - except the combination to my diary. She was even the first person I told after I lost my virginity!

Let’s see ... what else? I live in an upscale neighborhood in the south side of Pittsburgh. Our home isn’t nearly as luxurious as many of the homes in our area but it’s just fine for the three of us. What I like best about it is the deck. Our house, like most homes in Pittsburgh, is built on a hilly street such that our front door is level with the front yard and street but the garage in back is at the same elevation as the basement meaning our concrete driveway has a pretty steep drop. On top of the garage is a deck the size of our two-car garage so it’s pretty big. The only way to get on the deck is from the kitchen in the back of the first floor. My bedroom on the second floor overlooks the deck and I’m about the only one who gets to see what’s going on as it has a security fence built around that’s also tall enough to provide privacy.

By far the deck’s best feature - besides the fence that lets me lay out and tan in whatever I want to wear or don’t, is the hot tub. OK, so a swimming pool would’ve been even better but the hot tub is great. I LOVE lying in it and letting the jets flow against me. Sometime after my eleventh birthday I figured out that the jets felt even better against certain parts of my body! It didn’t hurt that we never wore swim suits in the tub unless we had visitors making it all the easier to enjoy them.

This brings up another thing I love about my life - my parents are fairly nonchalant when it comes to nudity and sex. However, that does NOT mean we were nudists and nobody runs around the house flaunting themselves. Well, except my Aunt Linda but she’s an entirely different subject. While nobody screams when they’re seen naked, at the same time there ARE rules for modesty and proper decorum to be followed. For example, sleeping nude or being bare-ass in the hot tub was acceptable while eating dinner or watching TV naked was not.

As for sex I already mentioned I gave up my virginity to my first boyfriend a few months back in the summer. He was sixteen at the time and going to be a junior so I felt pretty proud of myself to attract his attention, especially given my lack of development in certain upper regions of my body. Steve had a well-earned reputation for only dating bimbos with big boobs so when he asked me to suck his dick in the movie theater on our first date I wasn’t about to tell him no! No way was I going to make him think I was just some naive little freshman girl with little boobs. Sure I was a little scared at first because I had no idea what I was doing but I must have done pretty well as he asked me out again.

The same logic applied when Steve fucked me for the first time a a short while later. It was well known fact girls who didn’t put out for him didn’t get asked out again so I wasn’t about take any chances. Of course I couldn’t hide the fact I was a virgin but thanks to my mom’s sage advice and preparations I think it went off pretty well - at least it did for me. It must have been good for him too because since then we’ve done it most every day - sometimes more than once.

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