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The Story...Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the Internet. Some more precise details such as names and places will be left out to protect mine and others' privacy, and also because they don't matter.
As I have recounted in previous entries to this diary, once I finished university I decided to go traveling. I spent the months between doing my exams and leaving using my favourite adult personals site to contact people on my route, seeing it as an ideal opportunity to expand my sexual horizons along with all the other discoveries you make while traveling. In particular I wanted to make up for my only, and not-too-spectacular, experience of sex with a woman, which could hardly count as loosing my virginity (this experience appears in Chapter three of this diary).
A couple of months later and I was off, starting in St. Petersburg before the long train across Russia to get to China and the rest of Asia. This first stop was also where I was meeting my first contact, and my first chance to fill this hole in my experience, the only one who had replied in all of Russia, a sweet 25-year-old English teacher by the name of Annie. She had sent me her photos, not nude ones of course, as I had only sent decent ones of myself, and she was quite pretty. Not one of the tall stunning blondes of James Bond movies, which would have intimidated me, she looked rather more homely, a little plump but not obese by any means, a very cute open sort of smile and yes, blue eyes and blonde hair.
Very kindly she had offered to take a day off work to show me around her city the day after I arrived, telling me to meet her by the column opposite the Winter Palace, as this would be easy enough for me to find on my own. I was a little nervous as usual, but not too much as after all there had been no promise of sex in our emails, simply friendly chatter, then when I saw her waiting for me, dressed casually in jeans and a blouse, she smiled in greeting, and my nerves melted away as she put me completely at ease.
"Ah, you are Jack, yes" she said, and my spine tingled to the sound of a real Russian accent, even sexier than the fake ones in films. "I'm Annie, very pleased to meet you!"
"Pleased to meet you too," I said, shaking her hand.
The day went by very pleasantly as she showed me around some of the well known and not so well known corners of that beautiful city, giving me much more information than I would have got from walking around with my nose in my guidebook. We got on very well, laughing together as we discovered we shared the same sense of humour, and I soon forgot the artificial way I had met her. I paid for lunch and dinner, as it was the very least I could do considering she'd taken a whole day off work to act as a free tour guide, and as we drank more wine, we both got a little flirty, so I was a little disappointed when she said she needed to go home.
"I can walk you home if you like," I offered thinking this was what you were supposed to do.
"Maybe it is I should walk you home," she laughed, "I am used to my country, you are not."
But in the end she didn't put up a fight and seemed pleased to spend another 40 minutes with me going back to her apartment. It was not in an expensive part of town, which if you've been to Russia you'll know means it was pretty run down, but then that was no surprise as she was a young teacher and couldn't earn that much. At the door of the block she paused, her key about to go into the lock, looking at me in a coy way she hadn't done all day, and a slight purr entered her voice.
"Would you like to come up for some coffee, Jack" she asked.
My heart skipped a beat, and I stuttered an affirmative reply. Could this really mean what I hoped it meant Was it really that easy Was she really that easy Although I had been careful not to imply that I was contacting her to have sex, that was kind of the purpose of the site we'd both used, and I recalled that her profile, along with being very honest about her personality, had also been very honest about her desires, yet so far during the day she had not given the slightest hint that that was what she was after. However, the mere idea of it, unlikely though it seemed to my still pretty inexperienced mind, started a twitching in my trousers, enhanced as I followed her up the stairs and had my vision filled with her large but very sexy bottom.
"OK, this is my flat," Annie said, unlocking the door and opening it, letting me enter before her.
I barely had time to look around the narrow hall before there was the click of the door closing and I was pinned to the wall, Annie's soft, warm lips pressing against mine with her body, which was only a few inches shorter than my own. Fighting back my surprise, I kissed back, closing my astonished eyes to heighten the sensation as her hot wet tongue invaded my mouth, and I hesitantly returned her embrace, arms around her waist and back at first, but when she squeezed my buttocks I suddenly gained confidence and reciprocated, sliding my other hand under her hair to cup her neck and pushing back against her body.
Things moved very fast, too fast for my brain to get nervous, as it was still a little dull from the wine, and our kissing became more passionate, both of us trying to push the other against the wall. Then she was dragging me down the hall, shedding our clothes as we went, and into her bedroom, pausing to rip off her knickers and peel off her white socks. I did the same, giving me time to take in the tiny size of the room, with just enough space for a single bed against the wall, a bedside table and a chest of draws.
My observation of the room was cut short by her hand grabbing my now fully erect cock, the other hooking my head back into a kiss as she shuffled us on to the bed. She lay back with her legs spread open invitingly with a totally unshaven bush of dark blonde, curly hair in the middle with me kneeling between them observing her now flat stomach and large D or maybe E cup breasts heaving with her passion as she reached under her pillow for a condom and ripped the packet open.
Deftly and expertly she rolled it down over my dick, not saying a word but pulling me down by it towards her hairy pussy. I had to lean forwards, placing my arms either side of her shoulders for support, so unless I tucked my chin down to my chest, her face filled my view. Letting her take control as she clearly knew what she was doing and what she wanted, I felt her rub my latex covered penis up and down amongst the hair, once, then twice, the moist sound it made so loud it was clear even to me that she must be very wet. She pulled me in and instinct took over, I thrust my hips forward, feeling my cock sliding inside her easily despite its respectable size, until my pubic hairs were pressed into her lighter ones, amazed at how much I could feel through the condom.
Slowly I withdrew as much as my hips would allow and then slowly went back in, thinking that slow and sensual was how women liked it, based on what I had read. Stupid really, in every other aspect of life I never assumed "women" were or liked anything as one block, why should it be any different in sex I realised this soon enough as both her hands gripped my buttocks and pulled me down harder and harder, her own hips coming up to meet them.
Cottoning on, I sped up, encouraged by her smiles and odder expressions on her face and one hand moving up to my back, pulling me closer so my skinny chest was pressed against her softer, more substantial flesh. Her legs wrapped around me and I tried to go faster still, slipping out a couple of times at first, which required hasty readjustment, but soon I was so hard that even when I came right out, I slid straight back in again.
My thrusts were so hard now the bed was shaking, banging loudly against the wall and squeaking madly like deranged mice. At first this was joined just by both our panting, and Annie occasionally moaned, whether from pleasure or as encouragement I neither knew nor cared as I got deep into it. Sexual fury taking over, to the racket was added my grunts as I simply hooked one arm around her head, burying mine in the hollow of her neck, occasionally kissing it, the other arm massaging her arse against which my balls were now slapping noisily too.
Annie began to cry out "Da! Da! Da!" in ecstasy, I hoped afterwards that it was genuine, and certainly when I glanced at her hot, flushed, contorted face I thought so. With the contractions she was making around my dick I ceased all attempts to think of unerotic things, groaning loudly as I came. I continued to thrust and pant, feeling more cum shooting through my cock so I was amazed the condom could hold it all. Even after I had finished and had collapsed sweatily on her body, I gave a few more slow thrusts until it felt like I was going soft and I could muster the energy to lift myself up and pull out to remove the condom before it leaked everywhere. Tying it off and dropping it on the floor, I collapsed next to Annie's panting, sweat drenched body and kissed her.
"Ooooh, I needed that!" Annie sighed, as we both lay staring at the ceiling. After a while she turned on to her side, propping her head up on her arm to look at me. "You've not done this much before, have you Jack"
"Nope," I said, reassured by the faint smile on her lips.
"That's OK," she replied, and laughed. "I am a teacher after all, I don't have time to teach you Russian but maybe I can teach you something else... When do you leave Peter" Peter is what locals sometimes called the city, my guidebook had told me, so thankfully I didn't look too confused at this point.
"Saturday OK, that gives us three nights after tonight then, I can't take another day off."
"I can take you out again tomorrow night if you like" I offered, trying not to be distracted as her free hand wandered freely through my chest hairs.
"No, no, I have marking to do in the evenings... But if you come around at about half five in the afternoon when I'm back from school, I can probably afford an hour or two of relaxation before I start..." She finished this sentence with her hand, now between my legs and playing softly with my balls.
"OK," I said, as if I was going to object to an apparent promise of two hours of sex each night. "How about Friday night though You won't have any marking to do then will you"
"Friday" she seemed to ponder for a moment, slowly pulling my foreskin back and forth over the head of my limp penis. "Yes... yes we can go out Friday if you like. We can go out properly, I can show you some Russian night life, it will be a lot of fun!"
She bent down to kiss me, her hot tongue invading my mouth once more, though more gently than before, in time with the movements of her hand that was still jerking me off with my foreskin. Tentatively I put my left hand that was not trapped against the bed by her large breasts on her waist, caressing up her side, enjoying the softness of her flesh.
As she didn't stop me, I moved my hand up from her belly to the side of her right breast, furthest from me, slowly feeling my way until I was gently kneading her whole breast, or at least as much of it as would fit in my hand. The sensation of holding it combined with the actions of her hand to arouse me again, so I was eager to get Annie in a similar state. Between squeezing her breasts, which she seemed to enjoy, I also began circling her nipples with my fingers and gently brushing them now and again, and to my delight they became erect after a few minutes.
My confidence was growing, probably in proportion to my dick that was almost fully extended now, her hands giving it a squeeze every now and again, so perhaps earlier than she would have liked I moved my hands down again, passed the round bulge of her stomach to the tangle of hairs below. I did my best not to rush things, as I really wanted to learn how to give pleasure as well as receive it and I had always read and heard that women prefer to go slowly, so I began by drawing my hands slowly up and down her inner thighs.
Annie, however, had already shown that she preferred things faster than an apparently "typical" woman, and I was getting horny again, so as soon as she began pushing her hips out a little towards me I interpreted it as a sign to hurry up. Rather clumsily I moved my hand into her pubic hair, stroking my middle and fore fingers up either side next to her legs, noticing that the hairs between them were wet, a temptation I couldn't resist.
Carefully, I pushed my middle finger down, allowing it to follow her hairy skin until it yielded and slipped into her hot wet slit. Resisting the urge to enter further right away, I brought my finger up through her juices, trying to find her clitoris. Eventually I found a small mound of looser skin at the top and assumed that this must be it, began to rub around it gently as I had seen in porn films, dipping back down periodically to wet my finger again.
She allowed me to do this for a while, occasionally correcting me with a gently touch of her hands, but apparently enjoying it, thrusting her hips more and more. The more she did this, the harder it became for me to continue, as my finger kept slipping off, but as she didn't seem to mind I tried inserting it in the hole below, extracting an even greater thrust. Encouraged, I began thrusting in and out, first with just the one, then finding that I could easily slip in a second, which actually made it easier. Doing my best to read her body movements, sighs and groans, I found the best technique was to simply keep my fingers inside her doing a kind of beckoning movement whilst pressing my palm down on the mass of hair above it.
I wasn't allowed to play for too long though, as she pulled my hand away gently but firmly and knelt up, telling me to move into the centre of the bed. She had another condom in her hand as she straddled me, ripping the packet open and putting it on me as expertly as she had the first time, adjusted her position slightly and sank slowly down, holding me in place so that her pussy slid easily over me.
All I could think of to do was put my hands on her wide hips as she ground them against mine, my cock sliding deep inside her. Our pubic hair pressed together in one mass, although when I looked down in the hope of seeing my dick inside her, all I could see was her stomach hanging down to touch mine as she leant forwards slightly to get a better angle. In fact, her position had made it fold a little, making her look fatter than she had lying on her back, but far from being a turn off I thought it looked rather sexy.
Bringing my gaze up I took in her large hanging breasts and her smiling face, obscured occasionally by her hair as it fell forwards from her movements until she brushed it away. Those big breasts were too tempting even for me, who had never been particularly obsessed by big breasts as I generally find smaller, well formed ones more attractive. But after a few minutes of watching them sway above me I had to reach up and cup each in my hands, squeezing them gently, and when I remembered to concentrate on them rather than the feeling of her vagina surrounding my cock, brushing the nipples and circling them with my thumbs.
For a quite a while she continued this steady grinding, my cock not moving that much inside her, although enough to stay erect, her face becoming more and more flushed, leaning into my hands holding her tits so they were pushed up. She began to speed up a bit, and moved my hands away so she could lean further forward on to her elbows, her face now breathing heavily on mine, her breasts and stomach pressed hard against me.
I wrapped my arms around her back at first, pulling her closer, then moved them down to grab at her buttocks, falling and rising over my crotch, enjoying the feeling of them in my hands as much as I had that of her breasts. As her movements and breathing became even more urgent, I pulled my knees up so I could thrust up into her and take a more active role, allowing me to withdraw further from her and get a much better sensation for myself.
Once more, she started to cry out "da!" just as our thrusting began to shake the bed against the wall once more, but this time I wasn't as close to orgasm as before, so instead of being taken over the edge I intensified my efforts, and was delighted to find this made Annie cry out louder then ever. She pushed herself up, first on to her hands so she could push herself back on me, then right up and back, kneeling right up and leaning back on my knees so that to continue towards the orgasm I could finally feel building in me I had to thrust up harder, arching my back up. This position did have the advantage of allowing me to watch my latex-clad cock slide in and out of her hairy cunt, wet with her juices.
Annie had closed her eyes now and thrown her head back, yelling with each of my thrusts, and began to push down to meet them once more making her breasts wobble erotically, as I started to grunt louder too and mutter "Yeah! Yes!" over and over. As I felt muscles inside her vagina clamp even tighter around my dick I let out a huge sigh and thrust up one last time, my second orgasm forcing its way through my balls to explode into the condom. The euphoria spread right through my body, a kind of haze filled my head so I barely noticed as Annie humped my ejaculating dick until she let out one last cry and slumped forward on top of me, panting.
"Oh, that was good, thanks for that Jack!" she said a few minutes later when we'd both caught our breath, and got off both me and the bed. "Now, I have to do some work for tomorrow, so you'd better go. You know the way back"
"Er, yes," I replied, slightly taken aback by being chucked out so abruptly. "So, um, five thirty here tomorrow was it" I asked, pulling off the condom and beginning to tie it off.
"Yes, five thirty," she took the untied rubber from my hands and dropped it with the other she'd picked up off the floor into a small waste paper basket by the door. While I started pulling on what clothes there were in the room and then following the trail out the door into the corridor, she put on a dressing gown and showed me to the door. "See you tomorrow," she said with a smile and kissed me on the lips, then as I was still saying goodbye, she shut the door.
The next day as I wandered around doing the things that normal tourists do, I went over the night before in my head, and the coming evening, naturally getting rather aroused. By the evening though, I had decided that as she seemed to be so openly and honestly after sex and nothing but sex, I should seize the opportunity to learn how to do it well, as she had kind of suggested, so should try something new each time.
In practice, however, when I rang her bell at 5.30, free now of most of my nerves, things began pretty much exactly as they had when we'd walked through the door together the first time, although I did have some success in delaying my ejaculation a little bit by attempting to count down from a hundred in my head as we did it, though I still only just got past fifty.
It was in the rest period after this that I showed some initiative. When we both had recovered a little, and had become restless, playing with each other's bodies, I hesitated for a moment and moved my head down to Annie's nearest large, inviting breast. She giggled a little as I extended my tongue and gave her nipple an experimental flick, then clamped my lips to it and began to circle it with my tongue, flicking it again every now and then.
To my delight it soon became hard and erect, so I moved over to the other, which I had been gently massaging with one hand the whole time, moving my other hand up to play with the wet and slippery one I had just been licking. Soon her other one was erect, I assumed that was enough and began to move down, but as usual I was wrong, as Annie grabbed my head and pushed me firmly back into her bosom. I certainly wasn't going to protest, and continued what I had been doing with renewed energy from the knowledge that I was doing it right. I licked and sucked and kissed and squeezed her breasts, loving their texture against my mouth.
Finally though, she relaxed her grip, and I took this as I sign that I could move down. Keeping my hands where they were I began to kiss in a line down her stomach, sliding awkwardly down the bed until my feet were dangling in the air and my head was between her thick thighs, facing the tangle of pale brown hair. I brought my hands down to stroke her thighs, remembering the only other time I had faced a woman's vagina like this and wanting to do much better than that amateur fumbling.
Slowly I kissed inwards from a halfway point on one of her thighs, stopping the moment my lips touched a curly hair and repeating the same on the other leg, determined not to rush things. Then, spreading her legs a little wider with my hands, I hovered, my nose tickled slightly by one of her wetter hairs, looking down through the jungle of her bush to the mysterious folds of skin that was her pussy, inhaling the scent, preparing to do what I had fantasized about for the past ten years or so.
Carefully, keeping in mind the various guides I'd read on giving oral sex, I extended my tongue but tried to keep it relaxed, not wanting to do as before and just copy porn stars. My head bent down through her hairs and my tongue connected with something hot, wet, and fleshy, tasting a little salty maybe, it's hard to describe. I licked very gently at first, then increased the pressure, slipping through her outer lips and finding myself touching smoother flesh. I pressed on, moving up, doing my best to find her clitoris with just my tongue.
Trying to find out if I was doing things right, I looked up, but all I could see over the forest of hair was the plain of her tummy with the two mountains of her breasts on the horizon. My tongue had reached the top of the slit now and on to a clump of flesh, and a slight tremor accompanied by a sigh told me I'd hit gold. From then on I concentrated on this area, pressing the flat of my tongue on it and moving my head to drag it over it.
I was able to keep this up for much longer than my previous technique with the tip of my tongue, as keeping it relaxed didn't make it ache so, and although the hair tickled my nose and did sometimes get in my mouth it was not nearly as distracting or unpleasant as many people make out. Annie's tremors quickly became actual thrusts, pushing her crotch up into my face and grabbing at my hair with her fingers. Urged on by this, I began lightly sucking as well, my chin getting covered in her juices as it pressed against her slit.
Gaining confidence, I decided to try inserting my middle finger, very slowly, and then with it facing up, doing a kind of "come here" gesture as I had read in several online guides, stroking a mound of flesh inside her that I hoped was her G-spot. Whether it was or not I don't know, but she seemed to like it as her moans became louder, and she didn't protest as I slid in a second finger. She was really arching her body now, having small convulsions, and every now and again yelling out. It still seemed like she was building up to some climax, but I guess not as she reached down, and gently but firmly pulled me up by my jaw to kiss her with my wet mouth, smeared in her juices.
Not saying a word, she gently pushed me off her and slid down just as I had done but with less ceremony, to face my semi-erect cock. Immediately I could feel more blood pumping into it as she pulled back the foreskin and slipped it into her mouth. Looking straight down I couldn't see much, but by bending my neck to the side a little and brushing the hair from one side of her face I could kind of get a sidelong view, which was all I needed.
With the sight of my dick sliding in and out of her lips and the amazing sensations she was giving me with her tongue swirling around the head, it was not long before I was rock hard once more. Unfortunately for me though, it seemed that a full blowjob was not what Annie was aiming for, as shortly after she'd achieved this she had sat up and mounted me again, getting me to pass her another condom from under the pillow.
Kicked out again less than half an hour later, I made my way back to the hostel I was staying at, thinking things over. My thoughts continued the next day as I wandered through the Hermitage (this is the huge museum housed in the famous Winter Palace), and by the time I was on her doorstep once more I had resolved to persuade her to let me try the other thing I had failed to manage with the first woman I'd been with. Again, the moment the door was shut we leapt on each other in a frenzy of sexual passion, but halfway down the corridor to the bedroom I pushed her against a door to the side.
"I want to fuck you doggy style," I whispered in her ear, my previous awkwardness about talking so explicitly about what I wanted having evaporated in the heat of the moment and the experiences of the last few days.
"OK," she panted, "but I don't have any condoms in that room, we have to go-"
"I have condoms," I replied, pushing on the door handle and pulling her into the dark room. I had brought some condoms with me on the first day in the hope that things would go as they had, but as they hadn't been needed they were still in my pocket. Annie had flicked the light switch on just in time to stop us colliding into a TV, as it turned out that the room I had chosen was a sitting room.
As we stripped off our remaining clothes (Annie was already down to her underwear, whereas I just had my trousers and boxers to remove), I saw it was also pretty small, with one old, brown couch, a bookshelf behind it, no window, another shelf next to the TV on which there was a small hi-fi system and some CDs. The light wasn't great, but frankly, as I knelt on the carpet searching hurriedly through my pockets for a rubber to pull over my erect and throbbing cock, with a sexy blonde Russian girl on all fours waving her gorgeous big butt in front of me, a tuft of light brown hair poking out from under it, we could have been in a filthy public toilet or a luxury hotel suite for all the difference it would have made to me.
"Fuck me please!" she purred glancing enticingly over her shoulder, clearly enjoying talking dirty in English as I had done.
I didn't need any urging however, as I was already behind her, poking a finger in experimentally to check she was nice and wet, and also to locate the right hole amongst her jungle of hair. There was no doubt that she was ready, so keeping my finger in I used my other hand to pull my dick down to the horizontal, and guided it in.
I gasped, and for a moment was afraid I would come straight away, it was so tight with her legs held together. Catching myself, I took a couple of deep breaths, then when I was sure I'd stopped myself I brought my knees in from outside hers to the inside, so that she was a bit more spread out. This eased the pressure quite a bit, so I slowly pulled out as far as I felt I could without being out completely and thrust back in, moving my hands away from the action to grip her hips. I repeated this slowly once more, until I was satisfied that I'd postponed my orgasm for a bit, and began speeding up into a more steady rhythm.
Now and then I would risk a glance down at my latex-clad cock sliding in and out of her shining wet hairs between her beautiful, big, round buttocks, though each time I did this it made me more aroused, so I stopped. I also tried to reach around her to play with her dangling breasts that I could glimpse swaying with our movements, but a combination of her arse being the size that it was, and me not being quite tall enough, meant that to do this I had to bend so far over that I was almost coming out of her, so it wasn't too practical and had to be abandoned.
Despite these slight obstacles to fulfilling my fantasies exactly, it was still an amazing experience, my dick buried deeper in her than it had been before, the front of my thighs pressed against hers whenever I entered, and my balls hanging freely to occasionally slap into the front of her bush, so that they were soon pretty wet from the moisture trickling down from my shaft.
Annie had also really got into the dirty talk, yelling at me "Fuck me harder! Harder! Fuck! I'm a slut! Fuck me! Oh! Fuck me like the bitch I am!" I replied in kind, calling her a slut and a bitch, but not quite so loud as I still felt a little self-conscious about it. Gradually though, the English swearing disappeared as Russian replaced it, and I could make out words that sounded like "yeban", "sukka", "zloebuchi hui", and "yelda", though I have no idea what they mean. It sounded like she was nearing orgasm, as her cries became more gasped and indistinct, and she was thrusting back into me as hard as I was thrusting into her.
It may have been a genuine orgasm, or maybe her arms were just tired, but with a loud moan, her front half sank down, so that once she had settled she was resting her head on one folded arm. The other arm I could feel was down by the entrance to her vagina, as I could feel a finger tip on my shaft now and then, and my balls were now slapping against her hand. I continued to fuck her for quite a few minutes, and I began to worry that maybe I had forced my orgasm too far back, as now I was straining to reach ejaculation but nothing was happening.
I began to watch my cock sliding in and out of her pussy the whole time, and varied my speed, slowly dragging myself out of her, then fucking her in a fast frenzy for a full minute, sweat dripping off my back so much it was starting to itch. When Annie started to yell again though, and I could feel the muscles in her cunt contracting around my thrusting head, things started to move again to my relief. The heat started to build in my cock and my routine grunts and gasps became louder and more desperate, there was a familiar clenching at the base of my shaft and then I couldn't help myself yelling in triumph as I climaxed in an immensely powerful orgasm, ejaculating again and again.
After a short pause inside her, I resumed fucking her while my ejaculations continued, and then after, for once enjoying the hypersensitivity of my dick after cumming, until I realised that I was softening up and had to pull out. Annie collapsed sideways, panting, her flushed face looking at me with a smile through half-closed eyes as I peeled off the condom and tied it, being careful not to spill any of its contents on her carpet, and then sat back on my heels, caressing as much of her legs as I could reach. Finally she sat up and kissed me briefly on the lips.
"That was fantastic Jack," she said, taking the used condom from me and standing up. "I really needed that after today, it was pretty stressful... It's made me hungry though, would you like a sandwich"
"Um, yes please," I replied, unable to get used to her ability to change tack so swiftly. I got up and made to pick up my underpants.
"Oh, don't bother with them, you can get dressed later," she said and went out the door.
Feeling a little odd, walking around a strange flat naked, even if it was the third consecutive day I'd been having sex with its occupant, I followed. She ducked into her bedroom to drop the condom in the bin, then showed me to the kitchen, which unsurprisingly was as small as the rest of the flat, with a small wooden table by the window and a couple of chairs. She made us both sandwiches, talking about the day she'd had, having to deal with unruly children and a stupid colleague, appearing completely unconcerned by the fact that she was eating stark naked. I on the other hand was starting to feel a little cold, which she must have noticed, as when she took my empty plate she suggested we go to bed and warm up for a while.
This we did, huddling together under the covers and warming each other up, running our hands over our cold skin. It didn't take long for this caressing to become sexual, and as I felt myself becoming aroused I worried that as I'd had problems with my first orgasm, maybe I wouldn't even be able to reach the second one if she was on top. As I started licking her nipples though, I was hit by an idea that I thought might just kill two birds with one stone, so to speak.
This time, as I sucked and massaged her breasts, I moved my body slightly sideways, curling my legs up under me. When she eventually allowed me to move my mouth down her body, I was able to extend my legs again, but this time in the direction of her head, so that when I was kissing her thighs and facing her crotch, my semi-erect cock was level with her head, although being a polite young man I didn't thrust it in her mouth but held it a foot or more away. She took the hint though, her hands closing around my shaft and pulling back my foreskin.
I concentrated on her pussy, flattening her hairs, getting a good look at the slimy folds of skin before extending my tongue to taste them. I felt more confidant this time, taking my time, but soon placing my mouth over her clitoris and lapping at it with the flat of my tongue with my nose buried between her vaginal lips. Resting my head on her nearest thigh I wrapped my hands around her buttocks partly to pull her towards me at the right angle, and partly because I liked to feel them.
Meanwhile Annie had begun licking my now fully extended dick, also holding my buttocks for leverage, and our sixty-nine was under way in earnest, although it was with both of us lying sideways, one leg held up with the other serving as a pillow for the other person, rather than one of us on top of the other. It was actually a bit more awkward than I had expected, as she was not at quite the right angle, so I had to strain a little, but apart from that it was the best experience of the whole week. I merely repeated my technique from the day before but upside down, which made it harder to get my fingers in at the right angle, though I still managed.
Annie, however, had only given me a taster of what she could do the day before, and was now showing me all her cock sucking skills, licking and sucking, bringing me to the brink of orgasm surprisingly quickly considering how recently we'd had sex and the trouble I'd had, and then keeping me there. Whenever I had to take a break to breath (which was rather difficult with a noseful of cunt) I would risk a glance down and almost cum at the sight of her chin, just visible over her breast, and my dick half in her mouth above it.
Involuntarily I would give a little thrust, and then feel guilty as I didn't want to choke her, but then she was thrusting away like mad against my face, and it wasn't like I was trying to force my way down her throat, so I soon gave in to it. I began licking harder and faster to her thrusts, hoping that her hard breathing was a sign she was near a climax, as I didn't think I could hold off mine much longer.
In fact I couldn't, as a sudden increase in her sucking brought the heat raging up through my cock, and I could no longer control my thrusting, or concentrate on her pussy. Instead I moaned into it as I felt myself explode in her mouth, which continued moving around it, sucking every last drop. Regaining myself, I returned to eating her pussy, tingling as she continued to lick at my dick, even as it became limp.
She allowed me to continue for a few minutes, her hips shaking a little at one point, which was accompanied by some moans, although this may have just been for my benefit, then she sat up and pulled me to her. Her tongue thrust into my mouth, making me taste the cum on her tongue even as she tasted her juices on mine. Then, as before, she abruptly changed her mood, and politely but firmly kicked me out of the house, although this time with the promise of a proper night out the following evening.
This "date" was actually a bit of a problem for me, for as a backpacker I didn't really have any neat clothes, but as it was Russia I was able to find some pretty cheap, and decided that would do. I was meeting her at 6.30 in the middle of a metro station before we went to a restaurant she knew, although I would be paying for everything, naturally. At first I thought she was late, as I couldn't spot her in the crowd exiting from the train, until she was barely two metres from me and I realised I hadn't recognised her.
The three previous days she had been dressed in very plain, casual clothes, with her hair either loose or tied in a simple ponytail and little or no make-up, but that night she looked very different. She had styled her hair in a complicated bun; she was wearing huge hoop earrings, heavy, possibly a little too heavy, make-up, a white jacket, high-heeled white knee-length boots, and a figure-hugging, low-cut light blue dress that barely came halfway down her thighs. In short, she looked absolutely gorgeous, and not a little slutty!
"Wow!" I said, lost for words.
"Thanks," she replied, smiling. She offered her arm. "Shall we go"
"Oh, er, yeah, lead the way!" I took her arm and was steered out of the station and along the busy Nevsky Prospekt, the main shopping street. A little way along we turned into a side street, and then another, until after fifteen minutes we come to a restaurant. To my relief, it doesn't look too expensive, as I was on a pretty tight budget.
Inside it was warm and cosy, we were seated at a table in a corner, lit by a candle, and when the food and wine arrived it was very good. We talked quite easily together, Annie about her day at work, and I about how much I liked St. Petersburg (quite apart from the fun I'd had with her), and throughout I think I did very well in resisting the urge to stare continuously at her cleavage or wonder whether I couldn't see the line of her bra or she really wasn't wearing one. Towards the end of the meal while we waited for the bill, she went to the toilet, and as she walked away from the table I observed the shape of her body held in by the dress, her bare back, her leg muscles taught from walking in heels, and there was a slight jolt in my crotch as I noticed the unmistakable outline of a g-string through her dress.
"Now I think I shall show you some real Russian night life," Annie said as we left the restaurant, and lead me on another walk to a club where we had to queue to get in, despite it still being quite early in the evening. I don't normally like clubs that much, but with Annie I actually really enjoyed it, particularly once we'd had a few more drinks and she started dancing closer and closer to me.
Our dancing gradually had less to do with the music and more to do with our desire for each other, so to avoid colliding with others we withdrew to a corner. Annie was still pressing her body up against mine; turning around to rub her arse against my dick straining inside my pants, then back again to kiss me. I let my hands wander ever more freely over her body, making the passes over her buttocks and breasts gradually less discreet. Even hidden in our corner, our antics began to draw glances; so sometime near 11 Annie suggested we leave.
"Are we going home already" I asked, a little drunkenly, not sure whether I should be disappointed or not, considering what we would do once we got back.
"No," she replied, steering me firmly down the street. "We're going to at least one other bar. But first we need to make sure things aren't over too quickly when we do get back."
She had led us into another side street, but this was more of an alley, and at these last words pushed me hard against the wall, kissing me. I kissed back, hugging her soft body against mine, but she didn't stay long, pulling away and to my amazement sinking down to crouch at my feet and began undoing my flies. As what she was doing dawned on me, I reached down to stop her - we might be in an unlit alley half hidden by rubbish bins, but the street nearby was quite busy, and anyone who looked down the alley would see us. Quite apart from the embarrassment I didn't know what the law on public indecency was, but I'd heard plenty of unpleasant stories about the Russian police.
My protests were silenced though as Annie firmly brushed aside my hands, pulled out my rigid dick and stuck it in her mouth. Even in the semi-darkness we were in, I could see how sexy she looked sucking my cock so vigorously, her large earrings swinging and her painted lips taking me in smearing lipstick along my shaft. I gave in immediately, simply watching her at first, and then placing my hands on her head to pull her gently on to me as I pushed my hips forward, carefully as I didn't want to force anything, but I couldn't help moving a little.
It was clear that she didn't want to drag this out for a long and wonderful blowjob, but was just trying to make me cum as fast as possible so I would last longer later. Less then five minutes was all it took for her to achieve this, I closed my eyes gasping and leaned back against the wall as I emptied my balls down her throat. She swallowed everything with expert ease, then stood up again, leaving me to do up my flies while she scooped a couple of drops of spunk from her chin with her finger and popped them back in her mouth.
As if we had done nothing more unusual than go to an ATM, she took us back to the street and on to a bar. This one was a little quieter than the club, but we still danced for a bit, now that I was able to control myself a bit better. We had one more drink, although we were both a little bit drunk already, and retired to a table against the wall to drink them. The dancing had already started to awaken me, and as we sat down in the slightly chilly bar, my earlier question as to how much underwear was answered, as her nipples we unmistakably erect and covered only by the material of the dress, which immediately started to arouse me.
Our legs were hidden from other punters by the table, so inspired by Annie's back street blowjob I surreptitiously placed my hand on her bare leg and very slowly moved up, squeezing rhythmically, until I was right under the hem of her dress and could feel her lacy knickers against my finger. All the time Annie didn't protest or let on, although I noticed her breathing was getting a bit faster and she was clenching and unclenching her legs.
Checking again that no one could see I ran my forefinger over the front of her thong, my other fingers brushing the few hairs that weren't covered by it, the rest forming a cushion under the material, until I reached a moist patch where her pussy had been leaking juices all evening. I rubbed this for a while, then slipped my hand under the lace at the side into her hairs and her hot wet cunt. When I started fingering her here she let out a loud moan that she covered up by finishing her drink and choking a little, drawing looks. Blushing, she pulled my hand away and gave me a significant look. I finished my drink and we left, having to simultaneously resist the urge to run and the urge to burst into fits of giggles.
We got a taxi back to her flat, which seemed to take an agonizingly long time, but finally we staggered in through her door and could abandon all pretense of decency. My coat and her jacket had soon been thrown aside, but we were both a bit drunk, and Annie overbalanced and instead of continuing down the hall I was pushed into the kitchen, holding on to her to stop her falling down, and crashing into the table. We leaned against this, and I undid the strap to her dress, allowing her breasts to spill out into my hands and I began sucking them sloppily, while she clamped my head to them.
Overcome with lust, I pushed out of her grip and spun her around, pushing her down over the table which thanks to her heels was exactly the right height, her breasts pressed to the wood, pushing her skirt up a few inches to bare her arse, pulling her g-string out from her buttocks and down to her knees. She was yelling at me to fuck her again, her Russian accent stronger thanks to the alcohol, and I quickly dropped my trousers and pants, remembering just in time to get another condom from the pocket.
Precious seconds wasted to get it on properly, I didn't bother with my fingers this time, gripped Annie by the waist with one hand and pushed my cock in her pussy with the other, and began fucking her as hard as I could, the table banging against the wall. Helped by the alcohol, her earlier blowjob had done the trick, and I was able to slam my dick in her cunt for what seemed like ages without even the hint of approaching orgasm.
As her cries reached a crescendo and then faded again, I slowed my thrusting a little, and felt her struggling to turn around. Hoping she didn't want to stop completely, I pulled out to allow her to do so, but my fears were unfounded as she simply wanted to lie on her back and pull her legs up and out, pulling her knickers off one leg at least to hang from the other boot, both of which hung either side of us like bizarre wings as I re-entered her.
This new position did give me a fantastic view of my cock disappearing into her vagina and of her huge breasts wobbling like jellies with each thrust, but it came at the price of her tunnel being less tight. Luckily she compensated for this with contractions inside, so it was not so long before I came too, thrusting deep inside her so my cum would be squeezed out of my dick into the condom by her pussy. Finally, with both of us panting breathlessly, I pulled out and she was able to relax her legs, letting them dangle from the table just above the floor. She didn't move until I made to throw the condom in the kitchen bin, which she stopped me from doing without a word, taking it from me and walking to her room.
Kicking off my trousers that we still around my ankles, I followed her, glancing into the bin as I passed it to see that she had thrown the condom on top of the other five, and the was a faint whiff of leaked semen coming from it, though I didn't dare ask what she was keeping them for, maybe she just wanted to see how many she could get in a week. Noticing that Annie was almost naked, I began stripping off my remaining clothes and we got into bed.
I was pretty tired now after the dancing, the alcohol and the sex, but before long Annie began to get restless from just a simple hug and a kiss, and began the usual foreplay, trying to get me aroused again. Though I was skeptical as to that happening I decided to play along anyway, and if nothing happened down there I could always resort to oral again. To my amazement though, I did start to stir, barely half an hour since I'd cum, and although it took a while to get fully hard, she managed it.
From there I decided to take over a little, as I didn't think I would be able to stay hard with her on top, so I pulled on a condom and maneuvered us around so I was on top. At first we just went at a steady rhythm, my cock aching a little from having been erect so often in a night, but then I decided to speed up as there was no danger of cumming earlier and we got very noisy, the bed banging against the wall, me grunting, and Annie screaming out as usual. Presumably all the other times the neighbours had been out, but this time they were definitely in as after twenty minutes or so of making a racket, slowing down again, and then speeding up again we heard banging on the walls and shouting in Russian. We ignored it though, and luckily I finished quite soon after that.
Finally, we fell asleep. Sometime in the early hours, judging by the light outside, I woke and crept out of bed to the toilet. Returning, I found Annie facing the wall with her back to me. I got back into bed, hoping to go straight back to sleep, lying on my side facing her back with my arm around her as that was the most comfortable way to lie. To my surprise though, rather than go to sleep part of my body woke up, finding itself pressed against a pair of juicy buttocks, and started to get hard. Annie must have woken around then too, as she began pushing back against my shaft, helping it to stiffen, and within minutes we were fucking again, lying sideways on the bed in the same position, which made her very tight, going very slowly and quietly towards an early morning orgasm, before both drifting of to sleep again.
I didn't wake up again until quite a few hours later. At first I thought I was having a nice dream, and kept my eyes closed, but as my brain began to wake up I realised the warm wet sensation on my dick was not imaginary. Still, I kept my eyes closed, reacting very gently but pretending to be asleep for as long as possible. When Annie stopped sucking and pulled a condom on though, I stopped pretending so I could fully enjoy our final fuck together. It lasted a long time, both because we were going at a slow, hungover pace, and because having cum four times already in the past 24 hours, it was inevitably going to take a while to happen again.
Eventually it did though, and pretty much signaled the end of our short relationship. Sure, we took a shower together afterwards, went to breakfast together, and when she kissed me goodbye she promised to email and meet me if ever she was in the UK, but I never got another email from her. I didn't mind though, I had no real romantic feelings towards her even though she was the first woman I had really slept with, and she had greatly increased my confidence for future encounters. In any case, thanks to the Internet, I was to have no shortage of interesting people to meet in the coming months.
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- Story Details and Information
- Webmeets Diary Ch. 05
- Published: Dec 23, 2009
- Author: starbelliedboy
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- Category: Sex Story Series
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About: "My dick sliding in and out of her lips and the amazing sensations she was giving me with her tongue swirling around the head of my cock."
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