Chapter 1: Pointers From Mom

By the time I was fourteen and getting ready for high school a lot of things were changing in my life. At the beginning of summer vacation I’d spent a weekend camping with Sharon and few other girlfriends at her family campsite. Sharon’s sixteen year-old brother Steve tagged along, much to the delight of us all including his younger sister. Me and my friends wore nothing but skimpy bikinis the entire weekend which we hoped would driving Steve crazy. Even his mom joined in the fun with a bikini that made me wonder how stupid her ex-husband had been to leave her for some air-head secretary. I’d like to think we were successful and that the poor boy masturbated a dozen times before the weekend was over!

After that weekend I was thrilled and more than a little surprised when Steve called and asked me out. He had a bit of a reputation for fooling around with the older girls at school and for him to ask me out was almost an honor considering how young and inexperienced I was. What especially made me feel good was he always seemed to date girls with big boobs, like my best friend Beth, so with my all but non-existent chest he must’ve really liked me at the camp!

Steve took me to a 4th of July carnival and for most of the day was the perfect gentleman to me which sort of surprised (and disappointed) me. Based on what I’d heard about him from girls like Beth who’d dated him before I’d expected him to be groping me from the outset! Imagine my frustration when by evening I was beginning to wonder if anything was ever going to happen. Thankfully while we watched the fireworks he finally made his move and I felt the firm touch of a teenage boy’s hands exploring my small boobs for the very first time. Although I was probably as horny as he was, if not more, I wouldn’t let him go any further that night. Instead, I promised him that he would get to know all of me someday and I meant it when I said it, especially the “all of me” part. My fears that he wouldn’t ask me out because of my refusal were for naught as he called to ask me out again! While I had no doubt it was more because he wanted in my pants than my bubbly personality but then, what difference did it really make WHY he asked me out? What was important was that he DID, several time in fact.

For the first few dates I only let him play with my boobs but from the bulge in his pants I knew what he really wanted. Guys can’t control that sort of thing and it made me feel good that he was attracted to me sexually. Even my dad would get hard when I sat on his lap, especially when we were naked in the hot tub, but being my dad after all it didn’t count. My mom told me that all men react that way and so it wasn’t the same as when it happened to Steve who I knew probably wanted to have sex with me.

It wasn’t that I didn’t WANT Steve to touch me. In fact I was fingering myself every night and often during the day as well dreaming about Steve, especially that mysterious bulge in his pants. While I enjoyed being with him, I also knew he would probably stop asking me out if I didn’t put out for him soon than later. Even his sister Sharon, who I knew harbored her own naughty thoughts of her brother was warning me I needed to stop being such a tease. Boys like Steve have plenty of girls willing to do whatever he wanted and they had incredible boobs!

Finally one night while lying in bed after our last date, exhausted from some heavy-duty masturbating, I decided it was time. Realize that for a girl this is an important decision. Letting a guy grope my boobs wasn’t that big a deal but to go any further represented a major step for me, especially knowing that people would find out sooner or later. I had little doubt sure Steve would brag about it to his friends afterwards just as he did with the other girls he dated.

Eventually I did what I always did when facing a major decision I couldn’t decide - I sought out the advice of my most trusted advisor, my mom. Strange as that may sound to sound to some people you need to understand that she was more than just a mom, she was also my best friend. I knew I could count on her to always tell me the truth and her confidentiality would’ve put a priest to shame. She’d also been my sexual mentor growing up, not that we had sex or anything weird like that, but rather that she taught me the things a girl needed to know.

My mom’s first lesson was a result of her catching me peeking in on my dad while he was masturbating. Realizing my natural curiosity was arising, that night in the hot tub she had me stroke my dad’s penis to teach me how it worked. Consider it a sex-education class with a live demonstration as there was nothing sexual about it, at least so far as I was concerned. Of course I’m sure my dad had a different perspective but at that age I didn’t have a clue. My mom was there to keep him in check, ensuring nothing got out of hand.

Mom would teach me more about sex when she thought the time and place were appropriate. For instance, when she noticed I was starting to explore myself she took me aside and shared a few tips on masturbating. Although Mom even offered the services of her rather impressive dildo collection, I rarely took her up on that one. What I’m thankful to her most for is the attitude she taught me regarding masturbation, teaching me that it was a natural thing which most everyone did and nothing to be ashamed of or having to hide. It’s not like I’d put on a show for my parents but at the same time if I as horny I didn’t feel the necessity to leave the room and run off to take care of myself. Besides, it wasn’t like my parents even noticed.

Given the close relationship I shared with my mom I couldn’t wait to get home the night when Steve first kissed and fondled me to tell her all about it. I don’t know who was more excited, me or her. Of course she demanded I dish out all the details! Thus when I came to her and announced my decision about my intentions for my date that night with Steve, my mom was excited for me but she also appeared a bit apprehensive as well.

“So Kelly ... just how far do you intend to go with this boy?” my mom asked. It was just a question, not an accusation or criticism.

“I don’t really know for sure mom,” I answered truthfully. “I was actually thinking more about me doing something to him tonight.”

“Ahhhhhh, so you’re thinking about giving the boy a blowjob?” she asked, raising her eyebrows. “Are you sure you’re ready for that? I mean, don’t get me wrong but you still haven’t even seen, let alone touched, a boy’s cock yet you think you’re ready to suck one? Again, don’t get me wrong Kelly, it’s perfectly OK to blow your boyfriend and I know you’ll enjoy it but I just don’t want you to rush into this sort of thing before you’re ready.”

“Well ... I THINK I am,” I replied, squirming as suddenly I was feeling a bit defensive for some reason. We’d discussed sex and even oral sex many times before but never in terms of me actually DOING it. I guess it shouldn’t have been a surprise that discussing me actually doing it would be different than just an abstract conversation.