Me: hey M29

I'd lost count how many times I'd typed the same thing today alone. Expecting to be skipped yet again, I was surprised when I got a response.

S: hey! F18

Me: how're you doing?

S: I'm fine. How are you?

Me: I'm doing pretty good. What's your name?

S: S. Yours?

Me: I'm R

The conversation flowed from there. I found out she'd just finished her final school exams and was thinking of doing a part time job to earn some pocket money, that she hadn't decided what to do next with her life. I'd go on to convince her that if she didn't really need the money, she should just enjoy her time off as she'd never have this much free time again. Our conversation stayed tame and we ended it on a friendly note some time later, and I thought that was that - a one off pleasant chat with someone nice.

A few months later.

Me: hey M29

S: hey F18

Me: how's your day going?

S: it's fine. What about yours?

Me: I'm doing great. What's your name?

S: S. And yours?

Me: I'm R

It felt like many other conversations before that. The name didn't even ring any bells. I found out that she'd just started university a few months prior and that she was home on a short break. Our conversation flowed easily, like before, but I still hadn't noticed anything. Like so many other guys on the site, I was there for one thing and I slowly gave in to my urges. I decided to steer the conversation.

Me: do you ever play with yourself?

I admit, it was a rather bold question considering what we were chatting about before. There was a pause. I'd screwed up, for sure.

S: sometimes

Me: how often?

S: not very often. Maybe once or twice a week

Me: I see. Ever done anything with a boy before?

S: nope

Me: no bf before?

S: no

Me: hmmm okay. How do you usually play with yourself?

S: with my fingers

Me: ever had anything inside?

S: no

I knew I'd pushed my luck as it is. Probably enough to get skipped. But chatting with this cute, barely-legal, seemingly goodie two shoes was getting to me. And I wasn't thinking with my head too.

Me: are you feeling horny?

S: not really

Me: can I get you there?

S: maybe

An unexpected response.

Me: well, that's not a no. Does that mean I can try?

S: maybe. What did you have in mind?

Me: I'll tell you how to touch yourself, just follow my instructions

Again I expected to just get skipped. But after a short pause

S: okay

Me: are you alone?

S: yes

Me: I want you to take everything off for me

S: okay

After a short pause,

S: everything's off

Me: good girl. Now I want you to circle your nipples lightly with your fingertips. Nice and slow

S: okay

I could feel my pants tightening as my cock began to fill. In my mind, I imagined this petite girl as she did what I commanded.

Me: now I want you to tug on them gently

I unzip my pants, pulling it and my underwear down just enough to free myself.

Me: are those nipples getting nice and hard for me?

S: yes sir

Me: mmm. Good girl. Tug them a little harder

S: mmm yes sir

My cock that laid heavily against my thigh began to rise, the foreskin peeling back a little to reveal the opening at the tip.

Me: keep one hand on your nipple. Move the other slowly over your breasts, caress the soft skin between them. Then go lower. Slowly. Over your tummy and down to your pussy.

S: mmm

Me: no touching that pussy until I tell you to okay?

S: okay :(

Me: awh, be patient. Aren't you enjoying yourself so far?

S: yes sir

Me: that's a good girl. Now I want you to slowly slide your fingers past your pussy, gently massage your thighs. Kneed them firmly

I let her follow my instructions for a few minutes.

Me: now you're going to slowly move between your legs, run your fingers gently around your pussy. Trace your lips for me. Are they wet?

S: they're wet sir

Me: mmm just how I like it. Lick your fingers

S: can... It be licked?

Me: of course. I even like licking it from the source

S: hmm okay

Me: how does it taste?

S: salty

Me: haha. Mmm, yum! Get your finger nice and wet.

Me: now you're gonna lightly circle your clit, tease it nice and slow

I gripped my now rock hard cock and stroked it slowly. Precum had already started oozing out, allowing my skin to slide back easily to reveal the swollen, purple head.

S: fuck. It feels so good

Me: glad you're enjoying this

S: are you enjoying this? Does playing with me make you feel good?

Me: very much so. It gets me so hard and wet

S: mmm

Me: rub that clit a little faster and harder

S: yes sir

I too tightened my grip and stroked a little faster.

Me: faster

S: okay

I imagined her lying back on her bed, playing with that innocent pussy for me. My hand sped up.

Me: rule 1, no cumming without permission. If you want to cum you need to ask. Understand?

S: fuck. Okay :(

Me: now, tug on your nipples while you rub that clit as fast as you can

There was no response but I assumed she was too distracted. My hand sped up too. I could feel my balls tightening, so I slowed down wanting to wait for her.

S: I'm getting close

Me: mmm, then you know what you need to do

S: yes sir. May I please cum?

Me: yes you may, little slut. Cum for me

S: I'm cumming!

Seeing her response was enough to trigger mine as my cock spurted jet after jet onto my stomach. The last few dribbling down my shaft onto my hand. Breathing heavily, I typed with one hand.

Me: I came too. Did you enjoy that?

S: I did

Me: good. I'm glad you did

S: mhm

Me: first time doing anything like this?

S: maybe

Me: maybe? Hmm. Yes or no, slut?

S: hmph. Fine yes

Me: that's hot. Thank you for letting me the first

S: hehe. Did you have fun?

Me: mmhmm I did too. But I need to go now

I could feel the cum slowly flowing down my empty balls. I threw caution to the wind.

Me: would you be interested in doing this again?

S: hmmm. Maybe. Yes

Me: I'm glad to hear that

We exchanged contacts, I added her, and we said our goodbyes. Luckily I have a bathroom attached to my bedroom. I quickly made my way in, catching my dripping cum in my hands, making it just in time for it to fall on my shower floor. After a nice warm shower, I had some dinner and went about my night.

Later that night

Me: hey

To be continued...