Be Careful What You Wish For - Chapter 1

Looking back, I supposed that I have always been a dreamer, always curious and forever wishing for things that maybe, at the time, I shouldn't have been thinking about. Some of those things I now recognise come under the heading of being somewhat unmentionable but as I was also a wilful, independent kind of girl the thought that what I was seeking might be considered wrong never occurred to me. I just wanted to find things out and have fun doing it.

Growing up in a Toronto suburb wasn't anything out of the ordinary (whatever that is) and I had two parents who doted over me and a two little brothers who didn't, they were both a pain and in those early years I had as little to do with them as I could get away with.

Father was a strict disciplinarian but had a loving way of showing it. With him conversation was always a case of, "Kelsey, do this; Kelsey, don't do that; Kelsey, that's naughty, that's not what good girls do and such. Mother on the other hand indulged me to the extent that she allowed me to get away with doing things of which she knew my father would disapprove but she never divulged to him our 'girly secrets'. I guess that must have been my first experience of being in the 'Sisterhood'. Then again, there were other things that I did that my Mother didn't know about!

My first real experience with the fascinating world of sex came when I was still young enough to be spending my time hanging out with my girl friends at the local swing park. I suppose it must be some primeval urge to show off to the opposite sex even at that young age and my friends and I used to take great delight on swinging as high as we could on the swings so that our skirts would blow up with the breeze and for our little girl white pants to be ******* to the boys who were trying to look cool sitting opposite on some of the other playground apparatus. Some of them would mock us and yell out things to us like, "Kelsey, I can see your pants," proving that they could see our underwear but that was an indication of the stupidity of boys because that's exactly what we trying to do! I used to feel myself getting quite excited knowing that they might be looking right up my legs.

It wasn't only boys who used to be around the playground. I didn't give it much mind at the time but there always seemed to be a few old men sitting on the benches outside the play park reading their newspapers and magazines but all the while smiling and keeping an eye on us. If I thought anything about their presence at all it was that they were just adults enjoying seeing us young kids having fun, nothing more than that.

One time after having had an hour or so of teasing the boys and the evening getting late I left my friends and raced to get myself home before my *** got in from work knowing he wouldn't have approved of me being out so late. I left the gated playground and as I ran pass the benches that had just been vacated by an old man I noticed a torn piece of paper blowing in the breeze. It lifted in the wind and fluttered in front of me and I caught it with the intention of throwing it in the trash can that was nearby. I took a glance at the crumbled paper and my attention was caught by a coloured picture that nestled amongst some text. The trash can was ignored; I took the torn piece of paper home.

In the light of my bedroom the close-up image that had been so difficult to interpret in the evening light of the play-park sprang into focus. It was clearly a lady's pussy (a word I didn't learn until much later) being penetrated by something that looked like it had been purchased in a delicatessen. To my young eyes it was a bizarre sight. For sure, I could see that it was a vagina (a word that I didn't know at the time; my Mum said I should call it my 'front bum'). It looked very similar to my Mother's, a sort of gash just like mine but, unlike my smooth slit, was all covered and surrounded by black curly hairs. As for that meaty-looking thing which was pushing between the fat lips, I had no idea ... but it did look intriguing and confirmed to me that us girls could indeed put things inside us; something that I had recently tried to do when I was getting a bit itchy' down there'.

I looked closer at the picture and decided to attempt a little harder to get my finger inside me. I mean, if that lady had succeeded in putting that thing up her front bum then how difficult could it be to push my little finger in mine. As I said, I was a curious child.

My first few attempts didn't get very far but I soon learned that if I waited until bath time that the warm water and a soapy finger made things so much easier. Oh, that first time when I succeeded in pushing my little pinky inside was divine. I wiggled and stroked my finger inside the warm wet hole and each time I moved it sent the most delightful feeling through my young body. I thought that I must have discovered something very unique for nobody, my parents; my friends had never mentioned that that hole was meant for anything other than peeing. I couldn't wait for school next day when I would be able to confide my discovery to Annabel, my best friend who thought she knew everything.

When at break-time I told Annabel what I had found I could do and the pleasure that it had given me, she just laughed. I thought it was in disbelief but, no, she just said something like, "Wow, you've only just found that out. I've been doing that for ages …!" She then went on to claim that she had used more than just her fingers and indicated that she had used a variety of 'things' such as her toothbrush and the handle of her hairbrush. She even said that her mother's deodorant had a nice rounded smooth top that could also be pushed partway in. As I said, Annabel knew everything.

That evening was the beginning of me becoming a serial student of masturbation. With Annabel's advice in mind I picked up my hairbrush, the one with the nice rounded end, and I lay on my bed and did just as she had described and wetted the shaft with my spit and placed it at the entrance to my pussy (it was Annabel who told me that 'pussy' was a word that was used to describe our smooth little slits). Having had a few days of inserting my fingers I knew exactly what position to hold the brush so that the wet slimy handle could pass easily inside me. At first it was a bit difficult to make progress but I'm guessing the combination of feeling the warm wooden handle together with the sense of being 'naughty' and doing something that I knew my *** would be mad about, well, that was enough, after a little painful resistance, for the shaft to disappear from view. The feeling was unbelievable and as I slowly stroked the brush back and forth I knew that I just had to thank Annabel the next day for letting me in on her secrets.

From that day on I viewed everything in the house with fresh eyes and mentally assessed their potential as to whether I could use whatever to put into my pussy. Clearly there were limits, I mean I was only a grade 4 schoolgirl and there was a lot of other stuff that I needed to be concentrating on but one thing I did quickly learn was that the kitchen and the food closet provided a lot of stimulation. To my Mother's delight I began to show an enthusiasm for vegetables and when I went with her grocery shopping I would make sure she went by the produce aisle so that we could buy carrots, cucumbers and, on occasion, courgettes. She was impressed when I used to take care in choosing bananas to make sure that they weren't too big or too small but just the right size. She was totally ******* as to the reason behind my new passion for food.

I loved it when Maize (or Sweet-corn as my *** insisted on calling it) came into season and once again I would amuse my Mother by choosing with care cobs that were of a certain size. The feeling as that knobbly shaft was slowly pushed into my pussy was incredible.

Daddy did remark one time at the dinner table that the sweet corn crop this year tasted particularly nice. No way was I going to tell him what had caused the flavour change!

I didn't know it at the time but I had been 'blessed' with having an overly large clitoris and as time went by it become easier to get myself off with just the slightest of touches. Annabel told me that I was lucky to be so endowed and she used to delight in proving just how easy it was to make me orgasm whenever she came over after we shut ourselves in my bedroom. My Mother thought we must be doing schoolwork together and went to great pains to make sure that we were not disturbed by anyone, especially my annoying brothers, but Annabel, who knew everything, did tell me that my clitty when I got excited looked almost like a little boy's willy. I endeavoured to find out if this was true.

My first encounter with a boy's cock was not with either of my brothers (I had as little to do with them as possible) but with an older boy at school. I had already reached that milestone in life when I could call myself 'a teenager' and my young girl body was well on the way to becoming a young woman's body. I had a decent pair of tits filling out nicely; I had curves beginning to develop in all the right places and, oh yes, I was beginning to cultivate a nice peach fuzz of hair that spread over and around my pussy. It never occurred to me to shave the hair away, although I found out later that a lot of my friends used to do that, I thought it looked quite nice, especially with that clitty of mine being so nicely fringed by the soft downy hair.

However, that was just my belief and I knew that I really needed to have it confirmed by someone of the opposite sex and ask them for a 'second opinion'. That was when I became involved with Sandy.

Sandy was a couple of grades ahead of me and lived just up the street which meant that at school and around the neighbourhood that I used to see him a lot. He was kind of cute to my way of thinking and I began to tease him by basically stalking him (which wasn't difficult because he lived so close). When I caught his eye I would wink, rub my tits or pat my ass in what I thought was a provocative manner and I was quite pleased with myself when he began to favour looking and paying attention at me rather than the older and bustier girls in his year. I guess what clinched the deal of us getting together was the fact that I did live so close to him and I had signalled that it was very obvious he could make out with me. It didn't take too long before I had swopped sharing those special times with Annabel in my bedroom for going over to Sandy's house and making new discoveries.

The first discovery was that his parents had made a den in their basement away from the rest of his ******. Most of the area was a kind of recreational room with a pool table and some comfortable couches and a bar. In the corner by the stairs was another room that had some shelves and racks used as a store for groceries and stuff but there was no bathroom. Other than that, a perfect place to make out!

The next discovery was when he unzipped and pulled down his pants and sat back down onto the couch and for the first time in my life revealed to me a real cock (other than my stupid little brothers', that is). It was already stiff and I don't know if at the time I thought it not to be quite as big as expected given I had seen bigger in magazines that Annabel had shared with me but, oh my, I shuddered as my wish came true and for the first time I gazed upon that beautiful tool that I now knew that boys possessed. The smooth and furrowed fleshy skin that he grasped in his hand; the pink rounded knob that peeked out from the foreskin that loosely surrounded it; the glistening of a drop of syrupy fluid that was beginning to ooze from the piss hole and, beneath, that curious sack that was covered with the same downy hair as graced my pussy.

He saw that I was 'interested' and I guess, like all men, as I was to learn, he thought that he was displaying something special (which in a way he was) and he said something like, "OK, I've shown you mine; let me see yours." (Remember, we were kids and that's just the sort of thing you'd expect kids to say!). Although I was aware and could hear that his parents were only just up the stairs I didn't hesitate and I reached under my skirt, quickly pulled down my panties and stood in front of him sitting on the couch. I lifted my skirt and showed him what makes boys and girls different.

He liked what he saw and began to jerk and stroke his cock in response. He held onto himself with a firmer grip and as he made a downward stroke the loose skin of his foreskin was pulled back and the round shiny knob was fully revealed to me. I was fascinated, the pictures in the magazines may have provided a foretaste but they were nothing when compared to seeing the real thing.

I went and sat down next to him and I guess instincts took over for without a word being spoken he put his free hand on my thigh and brushed his fingers against my pussy as I in turn leaned over and placed mine around his other hand which was still slowly stroking his stiff cock. Once he was satisfied that I had got the right idea and was comfortable with the rhythm he slipped his hand away to let me have sole access to that warm fleshy rod; I was in little girl heaven and hardly noticed that he was pulling up my t-shirt so that he could see my tits.

I don't know how long we were sitting there, for all I knew it could have been seconds, could have been hours but it was total bliss. I was having my pussy being felt by a hand other than my own (a boy's hand at that!), my budding tits were being roughly caressed and massaged and I was holding a real, proper cock and learning how easy it was to please a man with the lightest of touches.

And pleased Sandy must have been with my attention for I had only been stroking him for, well, as I said, time had no meaning, when suddenly he pulled out his fingers which had been so deliciously slipping in and out of my pussy, fell back on the sofa and gave a groan and a spurt followed by a torrent of white stuff erupted from his cock head. I'd seen a picture and Annabel (and sex-ed class) had told me what it was and what to expect but, wow, I was totally unprepared to be confronted by the real thing. It was beautiful and I was so proud that I had caused it to happen. Sandy seemed to be quite pleased as well and I guess he would have told me so but just then his mother called down the stairs and asked if we were OK, did we want a drink or something.

After that first night I just stopped wearing a bra, to make things easier you understand, and I would go over wearing just a tee-shirt and cut-offs which I could simply slip down. I figured if we were in danger of being caught out by his parents it would be better that I was able to get covered up quickly! I learned how to play with his cock by watching him jerk it off, he would show me how to make a ring of my fingers and to let that fat knob push back and forth; he'd showed me how to fondle his balls while jerking his stiff cock with the other before he let me do it on my own without his assistance. It didn't take too long before I was granted my unspoken wish and was able to witness that that shower of cum spurting out and covering his stomach and my hand. He would then fret that the dribbling cum would get on the furniture and that his mom would figure out what was keeping us quiet down there and we would scrabble around to find something to clean up.

He told me that it would feel better for him if I used spit as a lubricant so I soon learned how easy it was if I leaned over and let a dribble of my spit cover his cock head. The inevitable happened when he put his hand on the back of my head and gave me a shove and I willingly opened my mouth and tasted a stiff cock for the first-time. He really didn't need to have been worried that I would protest for it was something else that the pictures in Annabel's magazines had prepared me for and I had already been wishing for the moment.

I guess instinct took over for I was soon sucking and licking that beautiful thing as if I was born to it. If I had thought that he was a quick cummer when I had just simply been wanking him then it was nothing compared to when my warm wet mouth began to suck. It would seem like only a few moments of me sucking and licking at the fat knob that I would feel his body jerk and then for that unseen torrent to hit the back of my throat and for me to be franticly trying to swallow as much of his load before he would pull out. It sure cured the problem of keeping his cum from staining the couch!

However, my visits weren't 'all about him' and I was able to show him what pleases a girl. After I had bought him off and he did that annoying thing that we girls on heat hate, that is, going soft. I would help him recover by demonstrating just what pleased me and I would tease him back to life by fingering and stroking myself in the special ways that I was so adept at doing. I hinted to him that this was what Annabel and me did together and I also told him about him about using things as a surrogate cock to fuck myself. It didn't too long for his cock to regain its strength as I whispered my descriptions and soon it would be standing proud again just like my stiff clitty which I would be flicking and rubbing till that delicious orgasm would flood over me. When I cum it wasn't with any great show like he could do but, something was going on inside my pussy for when I withdrew my fingers they would be soaking wet with my sticky juices that had exploded inside….

… and it wasn't just my fingers for my talk of how 'we girls' could make use of household items caught his interest and he got me to demonstrate using things that were in the store room. It was really kinky and I used to delight in taking a suitably sized vegetable from the rack and show him just how easily it could slip in between the folds of my pussy lips. After I'd cum we then would wipe off the cucumber or whatever and carefully replace it back on the rack! It wasn't too long after my demonstrations that we decided, unspoken, why was I wasting my time with substitutes when I could be fucked by the real thing.

So it was that I bought myself off once again and then when I slowly pulled out the dripping small cucumber Sandy gave me no time to protest before he was between my thighs and pushing his similar size stiff cock into my gaping pussy. There was no discussion, we just did it and I had my first fuck.

It would have been lovely to say that it was Sandy who took my virginity but that train had long departed (all my interest with the vegetable rack back home had seen me wave goodbye to that long ago!) but no matter, I took to be fucked as if I had been born to it. It felt so different to have a warm fleshy cock rather that some cold old vegetable in my pussy. Young as I was, I just wished that I had done this earlier and not wasted all those nights at home in my lonely bed with what I now considered to be poor substitutes. It was the start of new life for me and how I use to delight in having Sandy pump back and forth as I lay on my back rubbing that stiff clit of mine as we fucked like rabbits. He made a promise to pull out before he cum but there were a few times when he failed and I had the unique sensation of being flooded inside with what I knew to be life-creating sperm. I wasn't too sure how to react when that happened. On the one hand I knew that to become pregnant would be the end of the world as far as me and my ****** was concerned but, on the other, it was such an exquisite feeling that overwhelmed me when it happened that all thoughts of the consequences were somehow put aside. Whatever, we were 'lucky' and nothing other than pure pleasure and a bit of a mess on the couch came of it.

This first love was never going to last forever mainly because my appetite had been whetted and I was forever curious what it would be like to fuck other men. I say 'men' because it didn't take me long to figure out that older men might be more interesting and imaginative than boys … such as Sandy. Although he was two grades above me at school he was still immature in my eyes and certainly when we had finished fucking it took him no time to revert to being just another annoying 'Jock'. It didn't take me too long before I began to wish for something more interesting, more mature.

I guess the thought of having an older man stemmed from those times when after fucking with Sandy I used to have to scoot upstairs to use their bathroom. The lack of a toilet in the basement was no problem for Sandy, he used to use the sink behind the bar to take a piss. In fact, it was always great fun for me to come and stand behind him and hold his cock and aim the stream and try to make patterns or write my name! That was so neat to be able to do that but for myself it was upstairs that I used to go and always, I mean always, Sandy's *** would be around and he made sure I could see him as I passed by. There was no doubting the look in his eye as he stared at my tits (invariably I left my blouse undone in the rush to get to the toilet) and after a while, when I saw how easily it was to get attention I made sure that he got a good look as I passed him by. I never did see Sandy's mother around at those times but I'm sure she would not have approved to have seen her husband leering at me with his hand in his pocket and stroking his cock!

For sure, he must have known what was going on in the basement (perhaps the fact that he was always there indicated that he had been standing at the top of the stairs listening or even peeking) but he was not the only ****** member to catch us out for Sandy had an older sister, a really hot sexy girl.

It was late one evening when we had been making out on the couch and I had my blouse completely undone with no bra underneath and my skirt pulled high up around my waist (no panties, of course) she came tottering in through the back door to the basement. She was obviously high and far from being shocked at seeing what she was disturbing she just giggled as her younger brother tried to hide his raging hard-on with a cushion. She tottered over to us on her high heels to get a closer look and gave her approval by first leaning toward her brother and pulling away the cushion she kind of grabbed his cock and then gave him a passionate kiss. She then released her hold on him and turned her attention to me, reached down and put her hand over my pussy. I hardly had time to register before she then gave me the most loving tongue kiss. It was something that had never occurred to me before, not even with Annabel and our games in my bedroom, but I liked it and it was that moment that planted the seed that maybe I could also be attracted to women.

There was no sex with her that night but I was instantly turned on by her attention. As she broke the kiss to then totter her unsteady way up the stairs deliberately wiggling her butt I decided to add 'being bi' to my list of preferences alongside that of finding an older man to fuck with.

It wouldn't take too long before my latest wishes came true and I was able to tick both boxes and make a cuckold of Sandy's ***.

I'll tell you about that later.