Last Updated on: 1st January 2026, 11:32 pm

โ€œI canโ€™t today .. Prolly not till sunday honestly :/ by then though I should have more L and.. thisโ€ The joys of an affair.

Weโ€™d been playing tag for a few weeks.

Sneaking around trying to set up times.

When the times match up, itโ€™s time to play.

Affair with the world

Is it an affair?

โ€œbut Mr C is one creepy lookin mofoโ€

Thatโ€™s what he sent me after my Married Men post went out. Heโ€™s not wrong, the blurred pictures really did make him look like a creep.

Iโ€™ve read so many affair sex stories, yet even as an escort I never thought I would have my own. Even after reading Carolineโ€™s โ€œMy Sex Affairโ€ series and knowing I was going to work for Takeda Media, I still never thought Iโ€™d live one out.

At first it was just a simple client/whore transaction. Simple right? Then it turned into hanging out together. You see my job means that either Iโ€™m working or Iโ€™m hanging out with other whores. It was nice to do something different.

We would fuck everywhere. Even sneaking into Carolineโ€™s Secret Hideaway one day using our masks. (Sorry not sorry, Caroline)

If I was on the clock he would pay.

If I wasnโ€™t.. he wouldnโ€™t.

It was an affair where I was cheating on the job as a whore for a while. It was always fair though, he never expected a free fuck if he knew I was trying to make money. I tell him I hate him, all the time. Obviously I donโ€™t but Iโ€™m an escort, it would never really work.

Then silenceโ€ฆ.

Affair in the bar

Radio Silence

I messaged him after work one night.

Nothing.

Ok I thought, heโ€™s sleeping. I donโ€™t care that much. Iโ€™m a whore, heโ€™ll come back to me when heโ€™s either awake or ready.

Next day. Nothing.

I HATE HIM

No.. no I donโ€™t

I was having an affair with himโ€ฆcheating on my job essentially. Little did I know his secret..

For a week I pretty much heard nothing apart from a taxi arriving to take me to an event. I continued to work my shifts at Candyโ€™s. Which by the way, currently has massage vouchers for sale at 150L$. If you want one and want me to give you a massage then jump in this taxi and come and see me.

Affair in the Hideaway

WTF

Then

โ€œI was never ignoring youโ€

We would talk back and forth for a while. Few hours here and there butโ€ฆ no fucking?

Eventually I found out the secret. He had got himself a girlfriend. โ€œAlrightโ€ I thought to myself โ€œtime to do what I do bestโ€. A whore isnโ€™t a whore unless she can fuck another girls man. At least thatโ€™s how I see it. Sure itโ€™s fine to fuck any client that wants it.. but the ones in relationshipsโ€ฆ those are hot. Sign me up for a hot affair any day.

โ€œWe can meet up later if youโ€™re not too busyโ€

Bait out. Letโ€™s reel it in, Jess.

Then

โ€œI canโ€™t today .. Prolly not till sunday honestly :/ by then though I should have more L and.. thisโ€

OHโ€ฆ Well for that I could wait until Sunday. It was only a couple of days away anyway. I had wanted to do THAT for a while but we had never actually got around to it. Now not only was he finally going to have some time away from his girlfriend.. he was going to let me.

AGAIN??? This Affair Is Driving Me Crazy Already

I sent him a picture of me on my new sofa with my new collection of toys. Thinking to myself โ€œThis will pull him inโ€

Affair with a Dork

Nothing.

Four days

Nothing.

Turned out his girlfriend was working from home. He couldnโ€™t sneak away. Same thing happened again. And again.

โ€œtell your gf to take a day off so I can suck her bfs cock pleaseโ€

Then

โ€œso this new place lookin good?โ€

It was timeโ€ฆ

Oh yeah. You want to know what the thing is he was going to let me do? Iโ€™ll get to that next time in part two.


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By Jess

She/Her I'm Jess, the proud owner of this very website, Jess And Her Gentlemen, and the renowned X-Sisters Sex Bar and X-Sisters Entertainment in Second Life. Join me as I go deep into the wonders of the virtual world and share my experiences as a Second Life sex worker. Learn all about my fascination with virtual sex and the unique lifestyle I've built in the world. From guides to my real encouters, from Lovense play to self discovery, I write it all. Stay updated on my adventures (and kinks) by following my journey right here!

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