Note: All sexual activity in this story occurs between consenting adults who were at least 18 years of age at the time of all activity.
I'm Jill, and I'm a year younger than my neighbor and dear friend Kyle. We grew up in a very repressed environment in the rural Midwest, both with strict Protestant upbringings, and had known each other since grade school.
As teenagers, neither of us had much sexual experience. In fact, prior to the events I'm about to describe, Kyle essentially hadn't had ANY. We were very close in so many ways, as our homes were located in an exceptionally isolated farming area in Wisconsin, about a twenty-mile drive from the town where our high school was located. There weren't many other people our age around and really never had been, and neither of us had siblings.
As for me, my sexual experience up to now was limited to being brought to orgasm just after my 18th birthday once by a guy who was a few years older than me. It was a few months ago, right at the end of the school year, and it was fantastic! We were in his car kissing and he asked me if I'd ever been made to come by a guy before, and when I said "No", he insisted on doing it to me with his hand.
It worked. Oh man, how it worked. But alas, I learned shortly thereafter that he was doing this kind of stuff and more with a few other girls and was disgusted and hadn't spoken to him since.
That changed something about me in dramatic fashion all the same: now that I'd felt the intense joy of an orgasm brought on by someone else, through something other than self-stimulation, I was on fire to experience it again and again. I planned on the real thing, the whole intercourse experience, happening soon for me and though I didn't have a boyfriend and didn't really want one, I had a few guys in mind who would surely fulfill this burning need of mine for sex, and had recently gone on the pill just to be ready.
I planned to start the hunt for Mr. Right Now in the fall when school resumed. There weren't many guys around in the summer given where we lived, but that would all change once school started again.
So, after enduring a few months of this frustration, I found myself with Kyle enjoying a late-August afternoon at the place our families shared at a lake in Wisconsin. It was our last afternoon together there, and after this, Kyle was going off to college. It was a great day, absolutely perfect for lying out in the sun. Our parents were all out fishing on the lake so Kyle and I were sunning ourselves on the dock outside the cottage. The place was located in a very remote little nook and no one could see us.
Because Kyle and I had known each other so long, our friendship was almost sibling-like. Some aspects of it had grown confusing as we reached adolescence, as we changed from chasing each other around the woods and fields surrounding our homes, to talking about sex and things sexual.
In our younger years, especially from third grade through about seventh, I looked up to Kyle as he was older than me and held the upper-hand in our interpersonal dynamics. Even though he could have dismissed me as a neighbor brat with braces and blonde pigtails, he showed me how to fish, helped bait my hook, didn't make fun of the way I threw a baseball, and stood up for me at school if someone picked on me. He comforted me in the summer when Lassie ran away and in the winter, when the snow monster attacked Rudolph the Red Nosed Reindeer and I screamed, he told me that he'd seen the show before and that Rudolph would be okay, and he was right.
As a result he had quite a lot of power over me and I adored him completely. He never abused this, with one exception.
When I was about nine, I developed this incredible young-girl crush on him and it lasted for quite some time before transitioning from puppy love to merely liking him in an intense way. That summer in my bedroom, I set up a toy farm where I dreamed that he and I lived together as husband and wife. I remember having my dollhouse completely set up for our lives together. It was gigantic, almost as tall as me, something my dad had made for me in his wood shop out in the barn. I placed a small "Jill loves Kyle" sign hanging in the bedroom of the dollhouse, with two Barbie and Ken dolls lying in bed together. Off in the fields of my bedroom's carpet, I set up neat little plastic fences marking off crops and pastureland, with plastic cows grazing in the fields.
It was pure fantasy and I thought only I knew what it meant. The Jill doll made meals in the kitchen while the Kyle doll cut down plastic trees, ran the tractor and tended to the livestock.
I took this set-up down every night and stashed it in my closet, but one afternoon, the real Kyle busted into my room right after I'd set it up. I stood in breathless anticipation as he surveyed the scene, awaiting his reaction as his eyes settled on the dollhouse bedroom. To my dismay, he smirked at me and said "That's so stupid!" and went running outside laughing.
I was so crushed, so hurt and embarrassed that I shrieked in horror and then cried off and on all night and didn't go outside to play with him at all the next day. When we next saw each other, it was awkward at first, but finally he asked me if I wanted to throw catch and I agreed. It was a hot afternoon and later on, as we drank some juice his mom had made for us, he said he was sorry for laughing at me. I didn't acknowledge this but instead said, "Let's throw catch some more," so off we went, and not another word was said about it.
The dynamic of him having the upper-hand over me changed when I reached puberty. Even though he went through most of that before I did because he was older, he looked at me differently and acted almost meek around me as my breasts expanded and my little-girl antics contracted while I transformed into a young woman. It took a few years for all that to sort itself out, during which we didn't interact as much. In those summers, since no one else our ages lived around us, we spent a lot of time alone, not with each other, but by ourselves. Those were dark and lonely times as I recall.
Finally, though, we matured physically and to a large extent emotionally, and became close friends again. We'd since had many honest discussions regarding how, despite finding each other very attractive, we could not cross the line and become boyfriend & girlfriend. Our friendship was far too precious to us both, we'd experienced too many pivotal parts of our young lives together to risk it on a relationship that would perhaps fail and ruin everything for good.
That doesn't mean, of course, that there weren't interactions of a physical nature between us. These started right after I'd had that orgasm with that guy, and yes, I confess that I initiated this sort of activity as a way to release some of my pent-up desires. We were very "huggy" friends, often embracing each other for long periods, sometimes laying beside each other in one or the others' bedroom, arms around each other, talking about the deepest things in life. We occasionally shared a brief kiss on the lips, something I first initiated, and something that Kyle seemed to enjoy. All the same, these interactions weren't overt and didn't progress to more serious activity, and in fact the dynamic with us in that area was very complex, but it worked.
In truth it made perfect sense: two people at the height of hormonal rage, who were the opposite sex and close friends and isolated physically from others couldn't keep all that pressure completely at bay. This closeness between us, despite our mutual understanding that ours was a friendship and nothing more, had recently begun teetering precariously on sexual tension, which is one of the reasons I wanted to wait until Kyle left for college before engaging in intercourse with these other potential mates. I didn't want to hurt him – despite our agreement that he and I were friends and friends only, I knew that if I had intercourse with someone else right under his nose, it would be very hard for him to accept.
Kyle was fairly shy and he'd had only a few dates. He talked to me about his lack of action and I knew it was because he just wasn't aggressive enough. Kyle was indeed a good-looking guy, just too reserved. I hadn't told him about my orgasm in the car because I knew if I did, he'd only feel more inadequate since I was younger than him.
I really felt bad for Kyle. I could tell that he was very frustrated and also very full of sexual needs. About a month ago, right after I initiated those brief pecks on the lips with him, I walked in on him in his bedroom once and caught him masturbating. I closed the door immediately and walked out, but not before noticing that he was holding a picture of me with his left hand, a wallet-size of my junior class photo. I saw it for just a split second, as he crumpled it in his palm the moment he heard me open his door. That was an awkward moment and he avoided me for several days afterward, though I was pretty sure he had no clue that I'd seen that he'd been holding the picture of me.
Finally, I popped over to see him one afternoon and told him that what he was doing was normal, that I wasn't disgusted, and that he shouldn't be ashamed of himself. He broke down and cried on my shoulder over that. Another bonding moment, a pivotal one, like his turn at experiencing the shame I endured with the dollhouse fiasco many years prior.
Moreover, though, he often looked at me, you now, "looked" at me. People said I was attractive, with long blonde hair and a favorable build; Kyle often told me I was the prettiest girl around the school. I'd be a senior in high school when classes resumed this fall, and it would be so different now with him in college.
We both knew this was a big change for both of us, and that day on the dock, it almost seemed like he couldn't look at me enough. We were both in our bathing suits, lying next to each other, and he kept staring at my chest. I was wearing the skimpiest bikini my parents would allow, and it barely covered my nipples. We talked about many things and he kept looking at my body, and then he'd say he was sleepy and turn to his side, with his back to me. Truth is, he was getting an erection and didn't want me to see it, but his ploy wasn't working too well.
I saw it through his shorts, and I felt bad for him because it must have been frustrating. But, being a bit devilish and hornier than ever myself, I didn't make the situation any easier for him. I loved seeing him get turned on by me, and for the last few months, right after I initiated those brief friendship kisses on the lips, we'd begun doing little things to one another in a teasing way, things that would make the recipient blush and start breathing heavy, which would make the provider do the same. We never talked about what we were doing or what the interaction was about, as if we both realized that if we talked about it openly, that would be taboo. We just did it, and built many of these little favors around deals, which I'll explain in a minute.
Kyle would give me backrubs, good ones. That summer he often put my suntan lotion on, and he'd do my entire body, like he had that morning on the floor of the family room of our cabin. Slowly he'd rubbed the oil on my back, up my legs, inside my thighs, on my stomach, slowly, methodically, expertly. I loved it. He got right up to my crotch with his hand, and I told him I had sore muscles there, so with his hand pressed right up against my private parts, he rubbed back and forth and I started moving my hips to maximize the sensation.
I'd never participated so aggressively in this part of the suntan application ritual though he'd allowed his hand to "slip on up there" before, but now I couldn't resist grinding away as he moved his hand back and forth on my leg and against my crotch, and I couldn't help myself. I knew he knew exactly what I was doing and that he could hear my breathing intensify but I didn't care, and I also didn't mind when all this motion started loosening one of the two knots holding on my red string bikini bottoms.
Finally, I got the point where I was about to come and I had to squeeze my legs together so he'd know to stop. I didn't want him to see the wetness he'd made of my bikini, so when we walked to the dock, I kept my towel wrapped around me until I calmed down.
As for me, the kisses had opened the door to more, and I soon found that he loved things I did to his ears. When in a conversation about something that would lead to an embrace, I'd playfully nibble on his earlobe, breathing heavily, and he'd freeze like a statue until a shiver would come over him, and then I'd let go. Sometimes I'd stick my tongue inside and go round and round, letting out a soft sigh once in a while, and he absolutely loved that. He'd shiver to where he couldn't speak, and I got an intense feeling of sexual satisfaction out of this.
So that day, as we talked, as I saw him staring at my chest, I was teasing the daylights out of him. When he's say something funny I'd lean toward him and whisper "You're so silly" and snuggle up, gently grasping his ear with my teeth and then slipping in my tongue. I did it such that he had a perfect view of my cleavage and also pressed my breasts against his arm. This cycled on for a few hours and each time, he'd freeze up, and I'd notice the tent forming in his trunks, and then he'd turn his back to me saying he needed to close his eyes for a few minutes and snooze.
I had a plan, one that I'd been caressing in my mind since we arrived in the cabin two weeks prior. I cared for Kyle, this lifelong friend of mine, so much that I didn't want him to go to college completely inexperienced. So, as a going away present, I wanted to make him feel the joy of an orgasm at my hand so he'd have more of a hunger for action and become more aggressive on dates. I knew this would work for him in that way after what had happened to me, and knew that a handjob would be enough.
