Webmeets Diary : Chapter 05

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.

"On Saturday."

"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.