I forget the exact wording of the following conversations, but I've been as accurate as I can remember. This is a 100% true story.
Like many horny, single guys, I often go on sex chatrooms to meet like-minded people and chat about sex, masturbation etc. I find it so arousing to discuss that stuff with other guys and girls, talking about past experiences, advice, maybe even some role play if you meet the right girl.
Obviously, what most guys want ultimately, the 'holy grail' of such chatrooms if you will, is finding a girl who's willing to get on cam for and with you. As you can imagine this doesn't happen often, most girls are sensible enough to know that most guys like this are pervy douches, so when it does it can be amazing. I have been fortunate that I have been able to meet and befriend a few great girls on the internet, and we've had some great times together. But this was one of my first real encounters.
About 18 months ago, without meaning to sound like a jerk, I hit the jackpot. It had been a long night of jerking without much reward, and I'd reached that bored stage where I was just sending out the same message to any female in the room, basically and crudely attempting to find some slut to help me get off, something along the lines of 'Hey, horny young guy here looking for some fun' (classy huh?). Finally I got a reply. 'Hiya, I'm a horny young girl, wanna have some fun?'. Obviously I was sceptical many 'girls' in such chatrooms are actually guys trying to mess you around or get off themselves, but I gave it a chance, and we swapped messenger details to give us somewhere private to chat, and where, if it happened, pictures and web cams could be exchanged. However, she then said that she would 'brb', as she had to go do something. I wasn't surprised, and assumed it was a guy who realised he'd be caught out if he took things much further, so began to be a bit bitchy to her, 'Oh sure you will, if you're messing me around just stop, I'm tired and can't be bothered with any bullshit, ok?'. But she pleaded innocence, and even said that if I stuck around she'd make it 'worth my while'. I was intrigued, so I waited patiently.
Eventually I saw her pop up online, and we started talking. Nothing overtly sexual at first, we were just getting to know each other. She didn't tell me her name (although I found out later), but she seemed like a really nice girl. She was 18, American, and was really easy to get along with. I began to forget about getting off, and was just enjoying chatting to her. Obviously, claiming to be an 18 year old American girl in a sex chatroom seems like it could have been faked, so I was pleasantly surprised when she said 'So, do you wanna see me? '. Of course I did, and so we switched onto web cam chat. I wasn't expecting much looks-wise, call me shallow and generalising, but you don't expect the pretty girls to be trawling sex chatrooms for horny guys.
But I was amazed. She was gorgeous. A really pretty face that reminded me a little of Reese Witherspoon, lovely long golden hair, and a petite body. Because of the time difference (me in UK, her in US) she was wearing regular clothes, a zipped up hooded jacket over a t shirt, but with baggy pyjama trousers. Because she was so pretty I did not want to scare her off or lose her, so I didn't attempt to force her into anything sexual.
However, the conversation turned to relationships, and inevitably sex. She had had boyfriends, but had never gone much further than making out, the same as me. I was chatting to an extremely hot 18 year old virgin, who was the sort to frequent sex chatrooms and obviously taken enough with me to get on cam. She also said that I was pretty cute, which just about made her perfect. But because of this, and the fact that I was a horny virgin faced with this hot girl, I couldn't risk annoying her or scaring her away, so even though we were on cam together, clothed, I couldn't bring myself to take things any further. So we continued talking about more general stuff, and got along really well.
We'd been chatting for well over an hour, maybe two, and because it was getting late I said that I was thinking of heading off to bed, and that I hoped we'd speak again soon. To my surprise and delight however, she protested 'No! I promised I'd make it worth your while!'. Nervously I tried to play it off 'You have done, I've really enjoyed talking to you'. But she was adamant she was going to reward me. And I wasn't going to resist.
She took off her jacket, revealing a tight t shirt that showed she had a very nice chest. She saw that I was captivated, and staring at my screen, and she seemed to enjoy this, teasing me. She slowly took off her t shirt too, so that I could see her in just her bra. This was the first time I'd seen a girl in such a state of undress, and soon my cock was harder than it had been. Because of the angle of my web cam she could only see my upper half so couldn't see the effect she was having, but I'm sure she knew.
Inside I was begging her to go further, but again was terrified of pressuring her and scaring her off. But amazingly, she was the one that pressed for it. 'Do you want me to take this off?'. 'Yes please' I managed to stammer. She giggled - playing the nervous 'Hugh Grant' Englishman apparently works on chicks. As I stared, cock rock hard, she undid her bra, and revealed her young breasts. Apart from porn these were the first boobs I had seen, and while they were not big, they were so sexy. They looked so soft, her skin so pale and smooth, with bright pink areolae and cute small nipples. She seemed to enjoy the attention she was getting and the effect she was having, and drove me even crazier by teasing me more. 'Do you like them?' she asked as she squeezed, rubbed and pinched them for me - what was I supposed to say?!
Encouraged by her enthusiasm and my erection, I got bold - 'Could you go further? Take the bottoms off too?'. I knew it was a risk, but I wanted to see more, she was so hot and apparently as horny as me. She smiled, and pushed her chair back slightly so that I could see all of her. She pulled her bottoms down, and to my amazement she was bare underneath, no panties. She had done it so nonchalantly, without even appearing to consider the magnitude of what she was doing - like getting naked on cam was normal for her. She enjoyed showing off for me, taking her time, and allowing me to see what I had always dreamt of. I was staring at my first vagina, and one that had not been touched by anyone other than her. She looked so tight, with a thin strip of pubic hair above her tiny pink slit. I was astounded. The rest of her body was just as perfect, as she was petite and slim, with lovely rounded hips and a cute pert bum, and sexy legs and feet.
She sat back down, and we chatted again for a bit - about what I don't know, as I was totally focussed on her naked form. But she appeared to want this. 'How are you feeling?' she asked me. I replied that obviously I was good, and continued to shower her with compliments about how amazing she looked. 'No', she said, 'how are you 'feeling'?'. She wanted to know how horny I was, how hard my cock was. I chuckled, 'You wanna see?'. She said yes, as she had never seen a guys cock before and was feeling, in her words, 'playful'.
So I pulled down my shorts and exposed my rock hard member to her, honoured that I was her first. One thing I will never forget is her reaction when she saw it, how her eyes widened and her mouth opened as if gasping. I've not got the biggest dick in the world, but I've never been ashamed of my size, and she seemed to like it anyway. Now we were both completely naked on cam, each seeing for the first time. Then I noticed that she was moving her hand below the level of the web cam, as I could only see her top half. I cheekily asked what she was doing, to which she replied with such a sexy grin, 'You want to see me play? I said I'd make it worth your while...'. This was what I'd dreamed of. She angled her cam downwards, and put her ankles up on the desk so that she was presenting her pussy for me. It was so pretty, and had blossomed open with her arousal.
She began rubbing her fingers along her slit, slowly. She had a technique of masturbating that I had never seen a girl use before - it looked to me like she was scratching her pussy, that kind of movement with her fingers curled downwards. But it was so hot to watch, and it seemed to work for her. She did not even seem to be watching me stroking my erect cock on my cam, so focussed was she on her own pleasure. While some girls lean back with their eyes closed, she watched herself play, looking down at her fingers working on her pussy. She never stuck a finger inside, but continued with her exterior scratching motion.
She came fairly quickly. Her orgasm was not obvious to me - she was not a screamer or a convulser - but she said it felt great. It must have been quite something, as she seemed surprised at how wet she had become, saying 'Wow, I need to go clean up, look at this!', showing me the moisture on her fingers, which glistened. She stood up and walked out of the room. As she was making her way out, totally naked, I came, shooting a huge load. She missed it, but that wasn't her prerogative - she just enjoyed pleasuring others, while pleasuring herself.
We never masturbated together again. We chatted on cam again a while later, where she got naked for me again, but it didn't go any further. Then she just stopped appearing online, and we haven't spoken since. Of course I would have liked to, but I guess that's what happens when you find something as precious as the Holy Grail - you can't keep it forever. I like to think she's still out there somewhere in Internet-land, giving another lonely horny guy the best online experience of his life.