I was 29 and new to the city. While I had friends here, they were mostly married or in long-term relationships. As much fun as I had with them, I was young, single, and eager to date.
It was hard meeting people, whether it was through circumstances or my insecurities about putting myself out there on the market. At the time, online dating was in its infancy, and despite me looking down on it, I decided to try it. It was the gray dreary winter, I needed a spark - and honestly - I was kind of horny too.
The platform worked well for me. I was witty enough, and I could write well and quickly. But I tended to move slowly with the women. Back then, photos weren't even necessary. I'm decent-looking, but not a ripped-model type. I was pleasantly surprised to find that I could quite easily find cool people to talk to and sometimes meet. A completely different world from online dating in 2023.
Brooke was 24 years old, outgoing, and smart. At first, I didn't even know what she looked like, other than a written description, until we traded pictures on MSN Messenger. It turns out she was cute with light red shoulder-length hair. We quickly started chatting daily about anything and everything. We got quite comfortable with each other from the safety of being behind a screen.
One night I came home late, and "got online" with my desktop as we used to back then. After 20 minutes of browsing, I heard the familiar chime indicating a new message. I was pleased to see it was Brooke saying hello. We exchanged the usual pleasantries and updates on what we did that day and evening. She had been at a movie with a friend and I told her that I had a few drinks and only got home a little while ago.
Here was the conversation:
Brooke 11:15 - Hey you! What are you doing?
Paul 11:16 - It's very exciting, just tired and bored here.
Brooke 11:16 - Why don't you relax and watch tv instead of sitting at your computer? I guess you were looking for me π
Brooke 11:20 - Or are you looking for something else???
Paul 11:24 - Haha, always good to talk to you.
Brooke 11:27 - Still there?
Paul 11:28 - Ya, I'm here, sorry.
Brooke 11:32 - Helloooooo.
Brooke 11:32 - You're totally looking at porn aren't you π
Paul 11:33 - I'm just tired.
Brooke 11:33 - BS, it's porn! Hahahaha!
Paul 11:34 - Ok fine. Maybe lol.
Feeling mildly buzzed I decided I'd just admit it - I thought it would be fun to see her reaction.
Brooke 11:35 - You suck at multitasking you know. At least share something. I'm curious what you're into that has you so distracted? Must be hot hahaha!
Paul 11:36 - Ok, here you go.. (link to a page of a Playboy-type nude model on a tropical beach)
Brooke11:37 - She's pretty, but that's pretty tame stuff. What are you really looking at?
Paul 11:39 - Are you a detective or something lol?
Brooke 11:39 - I'm sorry! Just having fun with you.
Paul 11:41 - Ok, one more.. (link to still photo series of two women masturbating)
Brooke 11:42 - Doesn't it feel better to be honest??? π
Brooke 11:42 - I really am tired, so I'm going to go and let you do your thing.
Paul 11:44 - Lol ok, I am going to bed too. Night.
That was quite an amusing chat, but I really was tired and soon logged off and went to bed.
We were both online again around 9:00 the next night. We talked innocently about this and that. But I couldn't chat for long.
Paul 9:04 - Hey sorry to cut you off, but I have a hot bath ready, so I'm going to run.
Brooke 9:04 - Hold on, bubbles too???
Paul 9:05 - It's still manly, you know π
Brooke 9:04 - Of course! And I love baths too, have a good soak goodnight xo
A few nights later we were chatting on Messenger again, as usual.
Brooke 10:22 - You seem distracted again, must be better porn than last time!
Paul 10:23 - I think you like it.
Brooke 10:23 - Maybe lol. What you got this time?
Now remember, this is in the older days of online porn. If you wanted to watch a video you had to download a file to your PC and watch it on a player. So yes, I had been watching video clips, but wasn't sure she'd want to see what I was looking at. I found a fairly tame clip and sent it to her.
As time passed she kept asking for more. So each time I send one, I'd raise the stakes. Girl on girl, blow job, fucking, etc. It was a fun back and forth, getting her reactions and teasing. I was confident I could be bolder.
Paul 10:38 - Picked this one just for you π (MPG: grainy small video of a guy ejaculating on a girl's face)
Brooke 10:40 - OMG!!!! Wasn't expecting that!
Paul 10:40 - Sorry! Too much?
Brooke 10:41 - You're so dirty hahah!!! It's fine.
Paul 10:43 - Ok then! (MPG: higher quality large video of a cumshot on tits)
We went back and forth for a while, with her reacting to and critiquing the cumshot videos I'd send. Eventually, we went back to normal chit-chat before logging off for the night.
Over the next few days, we had a couple more tame chats. I suggested we should finally meet after talking for so long. She agreed and we planned to meet one afternoon at a restaurant halfway between the city and the suburb she lived in.
Our date went well. She is about 5' 1", with medium-length straight light red hair, freckles a big smile, high perky breasts, slightly thick thighs, and a bit of a bubble butt. She looked innocent and pleasingly Irish. She arrived wearing a tweed skirt and black leggings, and a thick sweater. It was a relief that our in-person conversation was just as comfortable as the messenger chats had been.
I told her about my apartment in a new building, and she complained about roommates. We shared mostly about work and life, but at the end, she joked, "Too bad you can't share your porn with me here!" Yes, this was before smartphones.
Perhaps because we were in public I blushed, but she did too. She was too fair skinned not too. There was a fun naughty tension building between us in person too.
I messaged her that night.
Paul 7:32 - That was fun today, thank you. Awesome to meet in person after all this time!