Kelly's Diary 008 - My Boyfriend's Mom Joins In - Cover

Kelly's Diary 008 - My Boyfriend's Mom Joins In

Copyright© 2024 by Kelly85

Chapter 1: Sex and My Boyfriend

Incest Sex Story: Chapter 1: Sex and My Boyfriend - This all happened long ago with my boyfriend and his mom but still ranks as one of the most surreal experiences of my life. Little did I know then how it would influence me later in ways I never imagined. Some people have expressed their doubts as to whether this really happened. Frankly I probably would as well if I was in their shoes. Yet as they say... truth is stranger than fiction.

Caution: This Incest Sex Story contains strong sexual content, including mt/ft   mt/Fa   Consensual   Heterosexual   True Story   Incest   Mother   Son  

There would never be another summer like this one! The biggest day in my entire life until then was the day I eagerly gave my virginity to Steve, the sixteen year-old brother of my friend Sharon. It was hard to believe just a few weeks earlier it seemed he didn’t even notice me with my small boobs, thin hips and coltish legs. Then to my surprise and delight, after flirting with him at his family’s camp with some of Sharon’s friends he called and asked me out!!! Desperate to prove I was just as good as the older girls with the big boobs he usually dated, I gave him my first blowjob that night and a couple weeks later we had sex for the very first time. Well, it was MY first time but that’s all that really mattered to me.

By the time I started going out with Steve my hormones had already been raging furiously just as they were in all my friends. Although I’d discovered the miracles of masturbation long before, once I had the feel (literally) of the real thing inside of me it seemed I couldn’t get enough of it! Even though I’ve never done drugs of any type the best way I can describe how I felt after experiencing sex for the first time was I was instantly addicted. I’ve heard that there are drugs that can lead to addiction after only one use. Well I don’t know if that’s true or just something to scare people but based on my own personal experience, when it comes to sex I can attest it’s definitely not an urban myth! Yep, it took just one time and I was hooked!

My transformation from semi-innocent church girl (OK ... I was never THAT innocent) to a genuine cum-loving slut was as quick as it was dramatic. It was like overnight it became where all I could think about night and day was how incredible it felt when Steve fucked me. For the first couple of weeks after our first time I don’t think we met once when we didn’t have sex at some point. We even fucked during a church service when I got so horny I couldn’t sit still like I was six years old again. When I finally excused myself to supposedly use the restroom other than my ever watchful mother nobody seemed to notice Steve had the same need at the same time...

No surprisingly, having sex with Steve also altered our relationship, at least for me it did. When we first started dating all I’d do was blow him. Even though he kept asking me out due to my natural “gift” for oral sex, it wasn’t like we were boyfriend-girlfriend in the way I’d imagined it would be when I was younger. Each time I pushed away his exploring hands I could tell his frustrations grew and I was worried he would stop asking me out if I didn’t put out sooner or later. Steve had a well-earned reputation for dumping girls who didn’t and practically every girl in school was waiting for him to dump me next.

Finally the time came for me when I knew it was either put out or get out. Steve’s hands were all over me whenever I was in reach. I could tell he was well past the frustration stage when he didn’t even say said goodbye one night when he dropped me off at home, even though I’d blown him twice. After he’d cum in m mouth the second time he tried reaching inside my denim shorts. Even though they were way too tight for him to have a chance of slipping inside, I still pushed him way. The silence in the car was deafening the entire trip back. He didn’t even kiss me before I got out of the car although that wasn’t a surprise. Steve was obsessively homophobic and would never kiss me with his cum still fresh in my mouth but he would at least kiss me on the cheek or neck.

So if I was so dreadfully afraid of being dumped by Steve, it would be natural for anyone to question why I simply didn’t let him fuck me. Even if I could have rationalized it as “just sex” I mean it wasn’t that I didn’t WANT to have sex with him, quite the opposite in fact. Every time my hand held his dick, every time my tongue reached out to touch the tip of his stiff cock, every time I felt him erupt in my mouth I felt this ache between my thighs telling me he belonged there. I masturbated every day to the thought of having sex with Steve. If there was a need for any further proof of my feelings for Steve, I even watched some porn videos I’d borrowed from my dad’s extensive collection and dreamed it was my pussy at the receiving end of his erection.

My concern had nothing to do with the typical worries of a virgin teen. While I was still a virgin biblically, physically I’d used some of my mom’s toys that put Steve’s cock to shame! Considering the sordid reputation I was already gaining thanks to Steve’s bragging about his exploits with me, some of which were definitely exaggerated by either himself or in the retelling, I really didn’t care if people ever learned he was fucking me. That included my parents, especially mom who just shook her head when I came home from a date and reported in. She’d be beaming at the start but there was no hiding her disappointment when I confessed I’d turned him away yet again. Apparently my mom didn’t start having sex until she was sixteen (or later if she was exaggerating as I suspected) yet her she was encouraging me at just fourteen.

No, the one thing holding me back was that I didn’t want to just give my virginity to someone who would see me as just another conquest. Eventually I decided to take the risk and my gamble paid off in spades. Once Steve took my virginity and realized this little teen girl was available whenever he wanted her, he stopped seeing other girls and I became the only girl he dated. What made it even sweeter was his younger sister Sharon was positively amazed by his focus on me! I can remember clearly to this day her telling me how she never would’ve believed her horny brother would ever settle down with just one girl - especially one with my figure at the time. In fact, she seemed more than a little jealous which was a little weird if you asked me but it just made me feel all the better about myself.

When we started dating I thought I was in love Steve but as the only child of professional parents I was a lot more mature than other girls my age. I quickly realized I didn’t love him, at least not in the romantic way my mom loves my dad. Did I have a crush on this older, handsome boy who was the first (and only so far) boy to fuck me? Heck yes! Was he the love of my life and my future husband ... no, at least not yet at this stage of our relationship. Despite his rather formidable reputation he’s earned with the girls at school, especially those he’d been with in the past, when Steve was with me he was always a perfect gentleman. Yes he held doors for me and carried my things but I especially loved how he always made me feel special when we had sex. No girl would be lucky to have a guy like him at a time of her life dominated by “firsts”, someone who didn’t take advantage of her naivety and lack of experience. Gradually over time my feelings for him matured to a deeper form of love but at this early point in our relationship I was simply infatuated with the guy, not to mention he made me feel incredible!

It was now two months since our first time and Steve was still the only guy I’d had sex with. It’s not like I didn’t have options. Thanks to Steve’s eagerness to tell everyone about us my popularity surged like a rocket with all the boys at school, especially the upperclassmen. While most of my friends seemed stunned by the sudden increase in attention, even more so they couldn’t comprehend why I wasn’t taking advantage of my fifteen minutes of fame and “branching out”. So of course it would’ve been easy for me to go out with other guys and indeed I turned down plenty of offers. For now I was happy to experience the same thrills most of my friends had already been enjoying - guys staring at me like I’m sexy, leering at me and making lewd comments. Well, I figured so long as Steve was satisfying me why complicate matters? Why kill the golden goose? I trusted Steve totally even if he did blab a lot about me and enjoyed having sex with him so I was quite pleased with my life at the moment.

Thankfully my parents were totally supportive of me during this time of change. It would’ve been easy to have been overwhelmed and make some bad decisions considering how quickly things were changing in my life. Both of my parents encouraged me, albeit each in their own unique way. My mom was always best when it comes to listening to me, like when I would tell her about my most recent date with Steve. Afterwards she typically offered suggestions and tips for how I might make our next date even better. My dad’s support was more practical, you might even call it commercial. For example he enjoyed buying me cute outfits to wear on dates although once my mom saw them they were usually ended up just being worn at home. No matter as he was happy just having me pose for his private photo collection. Once I was started sex on a regular basis he took me out to Victoria’s Secrets and bought me some sexy bra and panty sets to wear out on dates. It was sort of funny as that before I started having sex the last thing he ever wanted me to wear were bras and panties! Dad also liked taking me out for new bikinis and other outfits to help keep Steve’s eyes only on me. Of course they all had to be approved and photographed by him before I was allowed to wear them with Steve. Some of them though I just had to make sure mom never saw them!

Speaking of risqué clothing, why is it when a girl wears something cute or sexy, everyone assumes either she bought it herself or at the very most somehow she convinced mom to pay for it? In my experience it was just the opposite. My mom was always good for a credit card when I needed school clothes, church outfits, and other occasions where a little risqué was OK but there were still rules to be followed. When I wanted something more fun ... that’s where my dad came in handy. The only “rule” then was that I had to model it when we got home and let him take pictures of me for his collection.

My new boyfriend was no different when it came to making sexist assumptions. Once Steve was pleased seeing me in a new bikini that really highlighted my best feature at the time - my bottom, while accentuating my small bust as best as possible given the unfair limitations it had to work with. Oh yeah, he was REALLY pleased in that he couldn’t wait to get me out of it. As had become typical for us, it wasn’t long before I was enjoying the feel of a hard teenage dick filling me which was exactly what I needed at the time. Our relationship wasn’t based on our compatible personalities, shared interest in books or TV, love of the same movies, or any of those things that typically draw two people together. I loved that he was older, more mature, a REAL hunk, and it didn’t hurt every girl in school was jealous of me ... including his own younger sister. As for Steve ... well maybe he just needed something different than big-boobed cheerleader bimbos and having a young freshman virgin (well, EX virgin now) all for himself was a turn-on. It didn’t really matter to me to me WHY he wanted me in particular; what mattered was he DID and I was going to keep doing what seemed to be working to keep him.

Once when I was out of my new bikini and he was fucking me on my bed, Steve paused for a moment and kissed me. Looking thoughtful, he made a comment about how I needed to thank my mom for letting me buy such a hot bikini and how his mother would never let Sharon have one like it. As our relationship had matured, we would often have such conversations. Oddly it seemed we enjoyed talking more when we were joined than just sitting on the couch next to each other so these sort of conversations weren’t that unusual anymore. When I told him my dad had picked it out Steve gave me the weirdest look! Evidently he was too horny at the time to make small talk for TOO long as he didn’t say anything and went back to more important things - fucking his girlfriend. Even so I couldn’t forget that odd expression so afterwards I made it a point not to mention anything again about my dad buying my clothes, at least the sexy ones. Boy, if Steve couldn’t understand why my dad bought me sexy string bikinis, imagine trying to explain to him the latest sheer baby doll nightie I’d posed in just a few weeks earlier!

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