I’m Simon, I’m twenty-three years old and I’m now sexually experienced. I say that with some pride because until only a year or so ago the most I’d ever done was kiss a girl, and that was a long time before. Now I’ve tried more things than most people do in a lifetime. It was when I met Becky that everything changed. I was, as you might say, fast-tracked through the world of sexual exploration, and the kinky part of it too. It has been a breathtakingly wonderful experience. I’ll try and tell you the story of how it happened, but it’ll take more than one chapter.
I’m the stereotype average guy, tallish, slimish, with mousy brown hair and acne scars. I’m also naturally a rather shy person, with very little self confidence and a bad case of insecurity. That’s just the way I was built, but the problem was aggravated by an incident that took place when I was just, and only just, thirteen. I was at a school friend’s birthday party and during a childishly innocent game of ‘postman’s knock’ it fell to me to kiss a girl named Andrea. It just so happened that I didn’t like her and she didn’t like me, so it was with some reluctance that I went through into the darkened hallway where she was waiting for me. What happened next was to shape my life for years.
As I went to self-consciously put my arms around her I accidentally – and honestly, it really was accidentally – touched her newly growing left breast. Her reaction was completely, and I believe deliberately, over the top. She ran back into the party in floods of crocodile tears, shouting and screaming, calling me all sorts of names and swearing to everyone that I’d tried to ‘feel her up’. The result was that I was sent home in disgrace to face my wrathful and suspicious parents. But worse was to come, because the next day Andrea put it around the school that I’d tried to rape her, and I was bullied mercilessly from then on. She never did set the record straight and I had to go through the rest of my school years with the nickname ‘Pervy Simon’. Whoever said that school kids can be cruel was a supreme master of understatement!
You can imagine that for someone with low self confidence anyway, this was quite devastating and had the effect of causing me to become something of a reluctant loner, someone with few friends and who avoided contact with the opposite sex at all costs. It wasn’t until I’d left school and began to develop my own new circle of acquaintances that I began to relax a little, but by then the damage had been done. I was now so far behind the level of sexual experience that my friends had reached, or at least the level they said they’d reached, that I daren’t go on a date in case my lack of practice showed through and I set myself up for further ridicule. The classic dilemma.
The result was twofold. Firstly I went through my teenage years, the years when I most people begin to experiment with sex, relying solely on my right hand to provide an outlet and I emerged into my twenties as a complete virgin. Secondly, because I still actively avoided any sexual contact I now picked up the new nickname of ‘Saint Simon’. Talk about out of the frying pan and into the fire. Isn’t it a wonderful world?
I’ve told you all that because it will help you understand what happened last year. You see I don’t want you to think I’m a woman hater, or that I’m a closet gay or anything.
Now, to cut a long story a bit shorter, myself and several friends went out one evening to celebrate one of them making it as far as twenty-one, with everyone getting rat-arsed but me as I was the ‘designated driver’ for the occasion. Yes, I still get all the fun! Anyway, at the end of the night I dropped everyone else off and then took the ‘birthday boy’ himself home, and as he was in no state to navigate his own way up the path I draped his arm around my shoulder and half walked, half dragged him into the house.
There I found that his twin sister was home with some of her friends, all of them drunk, having been out celebrating the same birthday. They were in a quandary, as their own designated driver, Becky, had been unable to resist and was as smashed as the rest of them. So my appearance was immediately seized upon as the answer to their prayers and I was somehow roped in to run home the two who could not sleep over. I assume they expected to be safe with ‘Saint Simon’.
One of them, Mia, lived quite close by and she was soon dropped off, but then I discovered that the other one, Becky, the erstwhile driver, lived out in the sticks and I had about a forty minute drive to deliver her home. I wasn’t over impressed by this, but as I’d promised to get her home, get her home I would. I remember wondering to myself if St. Simon was the patron saint of suckers.
About halfway into the journey Becky suddenly declared an urgent need to pee and, as the road was deserted, tree lined, and unlit, I just sighed and pulled into a gateway to let her do what was necessary. She stumbled from the car, slid down a little embankment behind the trees and disappeared from sight, whilst I sat and waited. It was a bright moonlight night and so I couldn’t see her getting into difficulties.
After what seemed an inordinately long time with no sign of her return I climbed out of the car and went in search of her, half expecting to find her in a drunken sleep on the grass somewhere. But as I got near the top of the bank I heard laughing and scrabbling noises and I looked over to find her half way up the slope, unable to climb any further and collapsed in a giggling heap. For some reason I never did discover, she had her knickers in her hand and, with her short tennis style, skirt rucked up, she was displaying a very shapely bottom for the world to see.
“I can’t get out of this hole”. She said, looking blearily up at me and waving her free hand in my general direction. “Give me a pull up, will you?”
“It isn’t a hole, it’s a hill,” I replied crossly, wondering why I’d let myself get talked into being a taxi service in the first place.
“Whatever it is, I still can’t get out of it.” She carried on waving an expectant hand at me.
“Alright, pull your bloody skirt down and cover yourself up, and then grab hold of my hand.” I resigned myself to helping her up and leaned over, extending my hand towards hers.
I had expected her to reach behind and adjust her clothes before taking my hand, so her next action caught me completely by surprise. Instead of reaching behind to her skirt, she suddenly giggled, grabbed my hand, and gave an almighty heave, pulling me off balance and down on top of her. Together we rolled down the slope and ended up in an untidy heap at the bottom. ‘Ha, fucking ha’, I thought, annoyed at myself for falling for such a childish prank.
“Oohh, that’s nice!” It wasn’t until she spoke, still giggling, but with a certain huskiness in her voice, that I realised that I had landed on top of her and that my right hand was placed fully and firmly over her left breast.
It was all happening again! Total panic overtook me, especially as my cock reacted by immediately becoming rock hard and pressing against her stomach. I had visions of all my troubles starting up again, another birthday bringing another accusation, except this time an allegation of attempted rape would see me behind bars. The irritation I’d felt at being kept waiting disappeared and was replaced by sheer terror. I jerked my hand away and tried desperately to roll away from her, but she grabbed hold of my hand, pressing it back against her breast, squeezing her hand over mine so that I could feel her stiffening nipple under my palm. Pulling away now just brought her with me and I ended up on my back with her lying half on top of me, still mauling her own breast with my hand. Becky was a tall, well built girl, not someone I could easily push away from me, but I kept trying.
“No, don’t stop, don’t you like it?” She had stopped giggling and was now panting, partly from arousal and partly from exertion.
Of course I bloody liked it, but I daren’t let it happen.
“Come on then, kiss me.” With that she clamped her mouth over mine, her tongue probing between my astonished lips.
I’d never been kissed like that before, in fact I’d hardly ever been kissed at all, and then it had been with mouth closed, so this was an experience and a half as far as I was concerned. For a moment I lay rigid from sheer disbelief, and then I felt her release my hand and I managed to pull it from between us. I put one hand on each side of her head and pushed, forcing her mouth from mine, momentarily mourning that lost kiss before common sense took over again. I held her head away from my face and looked straight into her eyes, realising in that instant that, drunk or not, here was one beautiful young woman.
“Stop it, Becky. We shouldn’t be doing this.” I spoke directly at her face, but I don’t think a word was registering. She was gazing down at me with eyes filled with drunken lust. “Come on, let’s go.” I went on. “I’ve promised to get you home safely.” I emphasised the word ‘safely’, but to no effect.
Her only reaction was to use the gap now created between us to pull up her top, freeing her breasts and deliberately offering them to me. “Suck them, Simon, come on, suck them, and suck them hard.”
“No, Becky, no!” I tried once more to pull myself from beneath her and the terror I felt finally gave me the strength to push her away, and I slid free.
But for all her drunkenness, Becky was much quicker than I expected and she flung herself over me, this time landing with her body diagonally across mine but facing towards my feet. One quick wriggle and she threw her leg over me so that she lay straddling me, trapping my head between her naked thighs and pinning my arms beneath her. For the very first time in my life a smelled the beautiful scent of a sexually aroused woman’s cunt. It was a gorgeous and intoxicating scent that made my cock harden even more and I hesitated to push her away again. I wanted, – oh, how I wanted – to bury my face in the join of those legs!
Things were rapidly getting out of hand now; I was becoming as horny as she was. I wanted very much to be like other men and have sex with a woman, and I knew that this was probably my best chance. All I had to do was lean forward and I could taste her. I was sure she would let me loose enough to run my tongue around her cunt lips and, possibly, even to fuck her. But then what if I didn’t do it right and she cottoned on to it being my first time? Would I be laughed at?
I made up my mind. I couldn’t risk it. I couldn’t let anything happen between us. It would after all, I reasoned to myself, be a betrayal, a taking advantage of her drunken state, and anyway I was pinned down by her legs. In other words, I was chickening out, throwing away the best chance I would probably ever get. I desperately wanted it to happen, and at the same time I desperately wanted it not to, if you can understand what I mean.
All these thoughts took but the few moments of hesitation to race through my mind, but it was long enough for Becky to act. I felt, rather than heard, the sound of my zip descending and then her hand was wriggling its way into my boxers. The first feel of cool fingers closing around my hot hard shaft was just sensational – and I surrendered. I couldn’t fight my need any more and I lay passively while Becky pulled my cock out, even though she did actually hurt me trying to bend it through my fly. Then I felt her warm moist lips close over my head, her tongue working against my shaft, and I was lost. The feeling was so good, so utterly fantastic that she could do whatever she pleased as far as I was concerned, just so long as she didn’t stop. If she was going to try and set me up for sexual assault tomorrow, then so be it, and if she wanted to ridicule my inexperience, then that was ok too, just please don’t fucking well stop!
I did wonder for about half a second if I should try and take on an active role, but it was feeling far too fucking good to interrupt her, even if I was able to move and knew what to do, so in the end I just laid back and let her get on with it. That, in retrospect, was one very wise decision.
I don’t know if you can picture what was happening? We were lying at the base of a grassy slope, miles from anywhere, out of sight of the road (which is just as well as we were bathed in early summer moonlight), and surrounded by tree dotted pasture. It was just the sort of location that lovers dream of for their trysts, romantic and isolated, with just the hint of a risk of discovery to give it an edge. In other circumstances it would have been intensely erotic, but probably not when one partner is filled with anxiety and the other filled with drunken lust.
If anyone had been watching it must have looked to them as if we were in the classic sixty-nine position, with Becky on top, but in reality it was more of a ‘nine’ position as the ‘six’ was just lying there and taking it. The ‘six’, it must be said, was feeling little guilt but much pleasure. It would have made a stunning sight though, the gorgeous globes of Becky’s bottom and her strong shapely thighs must have been pale and clear in the moonlight, with only a narrow band of rucked up skirt separating them from her naked back and her mass of long dark hair.
Becky’s head must have been bobbing up and down as regular as an oil well. I couldn’t actually see from my position, but the alternate sensations of cool night air and warm velvet mouth on my shaft gave the game away, and felt simply wonderful into the bargain. Then I began to realise that, like it or not, I was soon going to cum and the recognition gave me a real adrenalin jolt. I’d never ever ejaculated with a woman before, and the prospect having my first one into her mouth was simply awe-inspiring. I lay there, my hands holding onto Becky’s legs, while I savoured the scent of her womanhood and the gathering tightness in my balls. But, of course, for me things never seem to go in straight lines.
No sooner had I reached the conclusion that she really intended to suck me off and then decided that it would be the best thing that ever happened to me, than she took her mouth form my cock, swung her leg over my head and clambered off. Of course, had I been able to react quickly enough, that would have been the ideal time to scramble clear, but I was no longer thinking along those lines, and besides, she was still holding onto my cock with her hand.
For a moment surprise ruled, then it was disappointment, then relief, then disappointment again. My mind was dancing through emotions like a kid at the fair, but before I could come to any concrete conclusions Becky was moving on, finally letting go of my manhood.
“Wait a minute.” She mumbled, speaking more to herself than me, and then she pulled her top off over her head before straddling me once more, but lower down and this time facing towards me. I wondered for a second what she was up to but then she grabbed hold of my shaft again and, shuffling herself into position, began to lower herself onto me. Then it was clear. She was going to fuck me! She was guiding my cock towards the beautiful opening between her legs. I was about to loose my virginity at last. I wondered for a delirious moment if she knew she was cherry picking, then I lay back and waited for it to happen with blissful anticipation. I had long given up any reticence.
But the first contact between my penis and a woman’s vagina was something of an anti climax, and certainly not the magical moment I was expecting Becky was still pissed, I was no help, and to put it in a nutshell, she missed her target and nearly broke me in half when she tried to lower herself onto me.
“Oh, bollocks,” That was her very unladylike answer to my cry of pain and the only comment she made.
It’s a wonder that I stayed hard and erect, but I did (although my impending climax disappeared) and she tried again. This time she was a little more careful and it worked. After a short and frantic fumble I felt the soft moist warmth of her tunnel engulf me and my virginity disappeared in history. And about bloody time!
The sensation was exquisite. I’d often wondered, and indeed fantasised about, what it would feel like when it finally happened, but the reality was far better than any fantasy. I can only describe it as sliding into a warm, moist silken glove that fitted perfectly, was just the right temperature, slid smoothly and easily over me, and then surrounded me with throbbing and pulsing perfection. Oh, it was just so fucking wonderful. Why on God’s earth had I never worked up the courage to try it myself and how did I go so long without it? I groaned with pleasure as she took me into her body.
For a couple of minutes she just stayed sitting on me with my cock buried up to it’s hilt inside her, then she shuffled around a little to adjust her position and began to rise and fall on my shaft. At first her strokes were slow and a little tentative, especially descending, so I guess she was trying to avoid another mishap, but as lust reasserted itself she speeded up, until she was going up and down as fast as she could.
From my point of view this was marvellous. Not just because of the unbelievable pleasure I was getting through my cock, but because the moonlight let me see her doing it. Her mouth was hanging partly open with the tip of her tongue just showing, there was a far away look in her partly closed eyes, and she had one hand on her thigh to prop herself up while the other was gripping the nipple of her left breast, rolling it between her fingers. It was a shame that she hadn’t taken her skirt off when she lost her top, because I’m pretty sure then I could have seen my cock sliding in and out of her, and that would have really been the icing on the cake for me, but even as it was the sight was wonderful.
Suddenly she leaned forward, placing both hands on my shoulders while still pounding herself on my cock, and whispered “Play with my tits.”
I would normally have been very reluctant to touch any tits, they had got me into too much trouble before, but this time I really, really wanted to. I felt a surge of anticipation run through me as I reached out to seize her gorgeous boobs, one with each hand. Of course, it sounds easy, but her movements were making them sway and dip and I fumbled before actually getting hold of them, but once I had they felt so, so good. My balls began once more to tighten in anticipation.
This was a new sensation for me, I’d never touched a naked breast before, but it was everything I’d dreamed of and more, the warmth, the soft skin, the texture, the resilience, I could go on for ages, but you all know what I mean anyway. I moulded them with my hands as Becky hissed her pleasure through clenched teeth. I didn’t know it then, but this was a sign that her orgasm was close, and I wondered for a moment if I was doing anything wrong. But then she cried out, a long guttural groaning cry in which the words “Oh God” were unintelligibly embedded and I suddenly realised that what was happening was different from the fake orgasms I’d seen in porn films.
As her orgasm swept through her she threw herself down on me and clamped her mouth over mine, still groaning as she pushed her tongue hard between my lips. Then she just hung on, her mouth on mine, her body flat against me, keeping my cock buried fully inside her as she slid up and down against me and let her climax run its course. Mine went away again!
For a little while she lay against me, breathing heavily and still moving her hips gently and sensually to maintain the sensations of my cock within her. Then she raised her head to look down at me much as I had done to her a little while before. But instead of complaining, as I had, she smiled, shook her head slightly as if in disbelief and spoke, the words carried on her breath almost as a whisper. “Christ, but that was good.”
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