It has been a long time since I last used a chat room. To be honest I'm not even sure if they still exist now that we have smart phones and their wide variety of apps for dating, online forums for a range of subjects, and the various forms of social media that are available. But back in the late 90s, when I was finishing school, and in the early 2000s when I was saying goodbye to my teenage years, I did on occasion visit a few different online chat rooms.
The first was while at school. A student website that we were encouraged to use had a chat page on it which once discovered regularly had several of us using for a bit of fun during some boring lessons. The problem with it being filled with people from the same class was that they were people that you would be talking to anyway, often sat at the next computer or only just across the partition, but by using an alias you couldn't be sure who it was or where they were. On occasions some of us guys would pretend to be female to wind up one of the other lads if we worked out which name he was using, or we may sometimes strike lucky and find students of other schools in there too and manage to strike up a conversation with someone new (hopefully female). It was all harmless fun to pass the time, and soon the bell would sound for the next lesson or home time.
As I left school in the early 2000s and entered the world of work, on evenings when I wasn't out with friends I would tend to use more 'grown up' chat rooms rather than the student type that I had used while at school. By 'grown up' I don't mean specifically sex or dating chat rooms, just chat rooms intended more for use by adults.
Of course, while the chat rooms weren't necessarily intended for sex or dating talk, inevitably there would be such conversation at times in addition to the general chat going on. In the chat room I began to favour, usually such conversation would usually be carried out by private message, and I soon worked out that the most common method of starting up a conversation was to send someone the simple question 'a/s/l?' -- meaning age/sex/location -- which also allowed you to quickly establish whether the person you had messaged was worth talking to, assuming they replied to you. Often there would be no response, but undeterred I would continue to try to strike up conversations, always hoping that the response to the a/s/l question would be that they were somewhere between 18 and 25 and female, and if I was really lucky also located relatively near to where I lived.
After a while using the same chat room at similar times of day, I started to recognise some regular names. One girl who was only a few months younger than me was in the neighbouring town, and initially conversation with her seemed promising, and at times a little flirty. However, I soon discovered that she was a mother of a young toddler, having had a baby while still at school, and it seemed that she was into taking drugs. I suggested to her that it sounded like she may be mixed up with a bad crowd and that it might be worth getting some help to escape it, but realised it was best to move on and speak to other people and hope for her sake that she would work it out for herself before she made too much of a mess of her life.
Some other young ladies seemed quite happy to chat, and also seemed more 'normal', or at least less complicated. Conversations again would at times be innocent flirting, with the occasional intimate question such as bra size, whether they were shaved, what things turned them on, and them asking similar questions in return. If I was lucky, cyber-sex with one of them would sometimes occur, with each of us describing in intimate details what we would do to each other.
Whilst there are obvious risks to this when you can't verify that the person you are talking to really is a 19-year-old blonde female with a 32DD chest, there was very little chance of ever actually meeting the person anyway, so the fantasy that you were describing to each other was really quite harmless.
One evening I logged on at the usual sort of time, and it seemed unusually quiet. There were a couple of usernames logged in that I recognised but hadn't spoken to before, and one who I had seen online many times but only spoken to briefly before, having got the feeling that she wasn't really interested in talking to me. I knew her name to be Louise, aged 20 and from Coventry, which was about 30-40 minutes' drive from where I lived.
After a few minutes a private message popped up from Louise saying hi and asking me how I was.
"Things must be quiet on here tonight. She's never been interested in talking before" I thought to myself. Regardless, I sent a reply saying I was well and enquiring how she was, as you would when making small talk with someone.
"You're from Coventry aren't you?" I asked
"Yeah, that's right. Good memory. Where were you from again?" Came her swift reply. The speed of the response surprised me almost as much as the initial contact from her, suggesting that I was probably the only person she was talking to right then.
"Not too far away then. Remind me what you look like again xx" was her next response when I told her roughly where I was from, not wanting to give too much away in case she wasn't who or what she said she was.
I tried to describe myself as well as you can via a private message on a chat room "About 5ft11, slim, dark hair, brown eyes, big........."
I couldn't resist putting the 'big......' bit at the end, knowing that she would probably think it was a bit childish -- let's face it, looking back on it now it was a bit -- and be fully aware of what I was suggesting, but it invited a response to either ask me what I had that was big, or she would come back with a witty response despite knowing.
She went for the witty response. "Big feet?"
"I think you know what I meant" I replied, adding a wink.
"Lol! How big?" she asked, which was even more unusually forward for her.
The truth was I wasn't sure how big my cock really was, and I wasn't sure I really felt comfortable getting a ruler out to measure it even if I was in my own bedroom.
"About 7/8 inches I think. You'll have to measure it yourself to check" I replied, adding a wink
"Interesting" was her reply, also with a wink added.
"Remind me what you look like" I inquired to keep the conversation going, and to help with any fantasy cyber fuck that may be to come if the conversation continued to develop in the way that it appeared to be going.
"About 5ft5, size 10, bluey green eyes, longish red hair" came her reply.
A red head. I'd never really had any interest in red heads before. No real reason for that other than I usually tended to be attracted more to blonde haired girls. However, during a recent conversation in the pub with an old school mate who was back on leave from serving in the forces he let slip that he had a thing for ginger haired girls, and when quizzed more on the reasons for it he told us he found them to be better in bed. Whether this was true or not I had no idea, but it had intrigued me, and now by some weird twist of fate I was chatting to a red head who had just asked me how big my cock was.
"Bra size? Shaved or natural?" I messaged back, wondering if that would be pushing things too far with her.
Moments later I got my answer. "32D and a shaved puss."
Considering that she had previously shown no interest in talking to me this was quite a bold and unexpected response, but taking it as a hint that she was prepared for some more intimate chat today, I went on tell her how much I love a nice shaved pussy and described to her how much I would love to lick and tease her pussy and clitoris. She in turn responded similarly, confirming that she got very turned on from receiving oral, and described how she would return the favour by sucking my cock.
