My First Encounter

I went to an all-boys school, although just around the corner was an all girls school. Up until I was 13, girls were just things I saw in the street walking home (and lusted after). 

Puberty hit me like a train wreck. Spontaneous erections, the embarrassing horror of wet dreams, and almost like flicking a light switch I was fascinated by these creatures that it seemed I had only just discovered shared the planet with me. 

And then the powers that be determined we would no longer be two separate schools, but one split-site mixed comprehensive school. We were to mix with the girls. Suddenly, at break and lunchtime, it seemed everywhere I looked there were girls flashing their panties while sitting cross-legged on the grass on the school field, or having their shirts unbuttoned dangerously low. To reveal soft globes of boobs. Honestly, there were some days my dick ached from being hard almost the entire day. Thank God by this time I’d discovered masturbation. 

I was fascinated with girls of course, but they seemed unattainable…..until I enrolled in the after-school art club and met a girl called Anna. Anna and I hit it off from the outset and we would often walk home together across footpaths and fields. I should point out there was never anything romantic between us though. 

So, there I was…14….friends with a real live girl! (And yes, I wanked myself to soreness over her…even though I didn’t have the first clue what to do should the opportunity ever arise. Anna was 15 at the time and something of a goddess. 

Teenage boys are boastful creatures. We are also, to coin a phrase, full of shit. The rumours that rebounded around the boys' locker room were many, and most of them utter crap. “Vaginas have teeth! If the girl wants, she can bite your cock off.” Or the ever popular “A girl can’t get pregnant on her first time.” Then there was “Girls give you STDs.”  (The ‘Can’t get pregnant first time was wishful thinking among boys and girls, and within the first term of us being mixed up three girls found out this one wasn’t true.) There were enough rumours flying round to make physical contact with a girl highly desirable, but more than a little scary. There were also rumours about how to ‘finger’ a girl. And some boys talked about how their girlfriend ‘smelled’ on their fingers, and one or two even spoke of kissing their girlfriend…..down there! This brought either looks of outright jealousy or abject disgust. Naturally, there was a load of boasting with some boys claiming they’d been ‘all the way’ with a particular girl, and that some girls were ‘easy’. I figured out there was a pattern. If a boy had actually got to second base, he’d tell his mates he’d got to third. If he got to third, he’d say he got to fourth….and one poor sod committed social suicide by claiming he’d fucked his girlfriend in the ass which led to him being called ‘Queer” and (for some reason) “bender.” Teenage boys can be cruel dickheads. Anal sex with a girl would soon become the ultimate prize for many. 

Anyway, back to the divine Anna. We were walking home one afternoon, a blazing hot summer’s day with Anna wearing a thin white shirt, open almost down to her skirt waistband and very nearly but not quite showing all of her tits. (Relatively small but exquisitely shaped) and I was trying to walk normally and carry on a conversation with a rock solid, leaking cock in my pants when she suddenly stopped and said,  “Can I see your cock? I’ve never seen one before.” 

Oh. my. God! I can’t possibly show her it in this condition! Then she grabbed my hand and led me off the path and into some trees. once there, she quite simply and to my amazement, lifted her skirt and dropped her panties. Suddenly I found myself staring at the Holy Grail itself. A small patch of light blonde pubic hair and the very top of what looked like two folds of skin. She invited me to kneel down which was just as well because my knees were shaking at this point. Then she leaned back against a tree, spread her legs and held herself open. “There. Can you see? There’s my clit, and there’s my hole. It feels amazing when I touch my clit, and even better when I’ve got a finger in my hole at the same time.” 

So there it was. I (unlike some of my friends) now knew where the clitoris was…and what it looked like. “Well? Your turn.” (Fuck) I was sure that any physical contact with my cock would result in me spurting so I very carefully unzipped myself and my cock, which had already escaped from my boxers sprang gratefully out. Anna stared at it for a few moments and said (with a pleasing amount of awe) , “Imagine that inside me!” I also noticed her hand was lightly touching herself. Then she simply reached out and grabbed me making me yelp. A couple of tugs and I shot my load all over her legs. Then Anna pulled my hand towards her and made me touch her. She felt warm and very slippery. 

I remember being shocked at how hard her clit was and how she would gasp when I touched it. “You need to be gentle there.” Bless her, she showed me how to massage a clit. Then she invited me to, “Put a finger in me…carefully.” 

Slowly I introduced my finger. I hadn’t gone in far when I felt this kind of puckered ring. Were these the much discussed teeth? I gently ran the very tip of my finger around this hole within a hole feeling for anything remotely sharp when Anna said, “That’s my hymen. If you’re careful, you can get a finger through the middle. (Ok…but how would I explain being minus one finger when I got home?)

Slowly and with some hesitancy I navigated my way through this little hole convinced at any moment I would feel the dreaded teeth. But no….no sign of them. Then Anna said, “Pretend you’re beckoning me to come towards you with your finger. I did as she asked and felt a smooth pad of tissue inside her which made her gasp. ‘Keep going…don’t stop,” so at that point it was definitely a case of ‘To hear is to obey'. In fact, if she had asked me to chew a tree down with my teeth I would have complied. “Faster!” There was some urgency to her voice now. "Faster” Then I felt her arms around me and her head on my shoulder. Suddenly she tensed and started to gasp words, “Fuck…ohhh fuck….fuuuuuuck.” Along with a series of, “Huhn…huuuuhn……huuuuuuhn.! And I felt a rhythmic contraction around my finger and a flood of wetness in my palm. I actually thought she had peed on me … and to my surprise, found I wouldn’t have given a shit if she had. 

By now I was rock solid again, and Anna treated me to a lovely hand job inviting me to smell my finger and hand which blew my mind. Of course I came again - who wouldn’t? Anna had some tissues in her bag and used some to clean my cum off her legs. When she picked up her panties I noticed some white stuff in them and asked her what it was. She told me girls leak all the time and that boys sometimes like to smell girls panties. She let me smell hers before she put them back on. It was a strange scent….a little sweat, this gorgeous….indescribably sexy smell, and I saw immediately why boys would want to smell this. I was an addict from that day onwards. Then she said, “I think my brother sneaks my panties from time to time." She didn’t look angry about it though, in fact there was a wry little smile as she told me. 

The rest of the walk home was an education for me. She dispelled the ‘teeth’ rumour, and told me a whole lot more about girls. She also asked me loads of questions about boys…including some I couldn’t answer. As we neared her home she asked me if I would actually ‘do it’ with a girl. I answered honestly that I was a bit scared to put my cock inside someone. In return she told me about a girl's first time hurting and them bleeding, but added that some girls deal with their hymen themselves. “Deal with?” She told me some girls remove it by using a banana or a candle, or a hairbrush handle and that she planned to deal with hers the same way soon so when they do it with a boy the first time, it doesn’t hurt.  Anna opened up a whole new world for me. 

Over the remainder of the hot summer semester we would usually do something sexual on the walk home once a week. She wouldn’t let me touch her vagina during her period, but she did tell me that when she rubs her clit when she’s on, the resultant orgasm is usually harsher, sharper. Still, during her period was when she let me explore her boobs and instructed me how a girl likes her tits felt. 

Remember, she was 15. Girls mature younger and are further down the road than we are at the same age. On the last walk home, she asked me if I knew what a ‘blow job’ was. (Of course I did - what boy didn’t ?) in what had become ‘our clearing’ in the woods, she invited me to let her give me a blow job. (Like she even needed to ask!) And I pride myself that I didn’t blow immediately. There were two reasons for this. One was I’d had a pre-emptive wank before Art Club, and the second was I felt a slight graze from her teeth. My cock really was someplace where there were teeth now! Even so, it felt like being transported to heaven, and I managed a half-strangled, "Gonna cum,” but she kept going until I came in her mouth. To my surprise, she swallowed it, remarking, “Huh…so that’s what it tastes like…nice.” Of course then it was my turn. I only have one tongue, so where does it go? Clit or ‘hole’? 

It felt natural to focus on her clit with my tongue and put a finger inside her, but this time, there was no puckered ring in the way! Someone had been at work with the hairbrush handle! “Put another finger in….stretch me.” A second finger duly introduced by pure accident ,my fourth finger pushed against her asshole and, because she was so wet, actually slipped inside. To this day, I’ll never know what made her cum. My tongue, my two fingers in her, or my finger tip in her ass, but feeling the contractions of her cum in both holes was extraordinary. 

No. We never ‘did it’. The following semester started off like we might, but then we had the rainiest autumn on record and our wander home became a bus ride - and it’s frowned upon to fuck on a school bus. 

Wherever you are, Anna, God bless you. You took me from 14 to 15 and educated me in how to please a girl. I do wish we’d gone all the way’, and I think if the weather had held, we might have. I’ll tell you a secret. In my wallet - in the back, under a little flap, is a condom. I bought it at the beginning of that fall semester ‘just in case’. It’s way too old to use now of course, but it’s a memento of the most glorious of summers, and what might have been.