The Progression of a Suburban Mistress

I have been very naughty, Damien typed as his hello our fourth time on.

I laughed and typed back: What did you do, bad boy?

I jerked off all weekend to thoughts of you.

All weekend?

Well, I took some breaks.

Again I laughed and took a second to think hard on what Damien was revealing. No longer were we even trying to pretend some sort of social preamble.

I wasn't so inexperienced not to realize how a classic older-woman-younger-man dynamic could birth certain specific fantasies. When Damien revealed to me that he was 28, far younger than the usual people who frequented the "OVER40INCT" room, I sniffed out my first hint. But then his typed "Yes Ma'ams"―even though he told me he was being overtly respectful―turned my mind even deeper to what I was suspecting. Why else would this young hot guy (Damien had sent his picture through our second time chatting) be in this particular chat with the likes of a woman with the screen name "Sassy CT" unless he was trying to glom onto something he was fantasizing about?

The time has certainly come to punish you.

Oh God, Claire.

No harm him knowing my name I had reasoned way back during chat one when I first told him it. Plus, I wanted to avoid the ma'ams and feared the possibility of a 'mommy' might not be too far round the corner with this guy (even in play calling me mommy would kill it for me as I had two sons and didn't want any connection to being a real mom in my chat here.)

Mmm, I wonder what you deserve for this...

Make it bad, Claire, make it a very harsh punishment.

Do you think you can handle that? I can be very firm when I need be.

Claire.

If the guy didn't have this penis out of his pants right then I'd be surprised. I was doing all I could not to roll my pelvis and bounce my bottom on my wooden desk chair myself.

Strip.

I could literally sense Damien doing so.

Please, Claire, Please.

Pleading already? God, I was really starting to feel quite a tingle. I had no idea how often Damien indulged in this kind of chat or how many times he had found an older―or younger―lady to dominate him; he was a dark haired, dark eyed, muscular cutie and I was sure he had plenty of women around to do his bidding. Now that we had finally reached this stage―albeit only at our third chat―could I deliver what he desired?