Paying for Past Flings

She had me primed for an online session. I just didn't know how twisted this was about to become.

Earlier in the week she had me lay out my schedule for a day in the mid afternoon later in the week.

That was a day of "suffering" she had projected for me.

The evening before when we were doing our normal chatting she said she wanted me to have a night filled with dreams and dread.

She instructed me to drink a Red Bull at bedtime. Followed by two 2000 IU Vitamin D tablets. Knowing this would cause me great restlessness mixed with vivid night mares.

She was right. I managed to get maybe two hours of sleep before my early 4am wake up call for work happened. Those two hours of sleep were filled with dreams. Night sweats and more.

When I arrived at work and opened my laptop at my desk I noticed she had been working late too.

She had logged into my laptop via team viewer and I noticed that on the desktop there were folders created.

She has made folders specific to certain things.

There was a folder with just snapshots of her panties and lingerie.

There was a folder of men that she found attractive or hot.

A folder was named "wife" that had pictures I had sent her over the weeks of the wife's panties and lingerie along with other into about her. Including a picture of her birth control, her sex toys, and some candid more x rated pics of her I had snuck and taken.

Then a folder of women I have had Inappropriate conversations with over the years and pictures of them that were sent to me in chats.

A folder of my ex's from years ago..Including ex's from High School that she had found off my Facebook page and saved.

The a folder of HER. Selfies, PG pics. And more.

Also the background was changed. It was a created image that simply said "background subject to change"

I was nervous.

I was worried and tired. But I knew shit was going to hurt today. Psychologically I was weak and she was going to pounce on it today.

The "notes" tab opened and she started typing.

Sure she will text me. Message me on Fet or in my email.. but when she typed like this. She was logged in..to my laptop. It was REAL.

"Today. You need to be physically prepared. But equally as mentally prepared. I'm going to rape your emotions today."

I got shivers.

It was then the background wallpaper image changed to one of the women I had inappropriate relations with. Jessica.

It was a picture she had sent me and early in my application process with Mistress she had me send every single image of any woman on my phone to her.

So Mistress had "selected" her for this session.

This morning while you work I want you to go ahead and take a viagra. It will come in handy later and help speed up the process.

It was at this point that several more pictures of Jessica popped up and the louse scrolled to the "Print" feature.

"Fuck!" I thought to myself as Mistress was about to send what looked like 5 photos of Jessica..most of which were her in lingerie or naked.. to the company color printer.

I rushed to it as they slide off. Luckily the office was still empty..but close call.

Embarrassed as I looked at them seeing this 25 year old woman who had the major hits for me..

I retrieved the viagra and took it. Stashing the pictures safely under the laptop.

"On the way home you will need to go to Lowes. Don't worry. It's not for chain or boarded wire. I just need you to purchase about two feet of CLEAR 1" hose. Think if it as a straw. Because I also will need you to get ONE gallon of milk.

I do as Mistress says and get home and hurry to the upstairs bathroom. The room we have deemed the "lab"

I turn on the laptop. And just as soon as it connects to the internet I see the Teamviewer session open. Also my phone rings with a FaceTime call from her as well.

I can see she has turned on the laptop webcam along with the FaceTime calls she is seeing me from two different angles.

She tells me to fetch my toy bag and prepare the room as she watches.

Her sexy voice I now hear with its beautiful French accent. Powerful.

I lay down a towel. And I take out the toys she commands.

First off is the Lovesense toy. My heart races as my cock..which is throbbing from the viagra..hasn't been inside ANYTHING in weeks. (And that was a grapefruit but that's a humiliating story for another day)

She lays out a basic formula.

First off. She instructs me to coat my cock with a massive amount of the numbing cream. Every inch..including the shaved balls.

Then she has me take a condom and place pin holes thru it. Then the condom goes directly over my now quickly numbing cock. Then ANOTHER round of numbing cream. Then a fresh condom over that. No pin holes this time.

"That way the second layer of numbing cream can slowly work itself into your skin thru the holes so we can keep you numb..well..for a LONG time!"

Then I take the suction based rubber cock toy..black.. and place it firmly on the base of the sink counter. I'll find out that it's not for my ass..

"Take the pictures of Jessica and place two around the dildo.

Then I want you to tape the other two on to the shell of the Lovesense. You are going to fuck her today. The final one..I want you to tape on to the gallon of milk. You're going to suck her too!"

"Place the plastic tube into the milk gallon. Then insert your viagra filled numb condom covered cock into your toy. I have the app to control it ready!"

She is watching me from two views to make sure I comply.

"I can clearly see that tube. I can see the white milk flow thru it. So suck. And I'll reward you by turning on the Lovesense and giving You pleasure..well..just take my word for it.. I know you won't be feeling it."

We have 60 minutes to finish that gallon. If you can't finish it..then like Jessica..you don't get to keep it.

Start sucking!"

I slip into the Lovesense and like clockwork as the luke warm milk hit my lips with the taste of the industrial plastic straw.. I heard the device kick on.

Then the abuse hit.

The laptop screen went to a hypnotic spiral as she started quizzing me on Jessica.

Of course to answer I had to stop drinking which made the Lovesense stop.

She asked me everything from where she lived to what color panties she had on in a certain pic she sent.

And I drank more. And more. And more.

The hypnosis file.. turned to like a sissy trainer file. Sounds of Fucking.

I couldn't feel a thing either.

Half gallon down.

I was really regretting my affair with Jessica.

"Suck more milk for me!"

50 minutes into this hell

My head was pounding from watching the screen.

My cock and balls were totally numb. Like I was worried that sensation may never come back. The Lovesense had chewed me up.

I was bloated. My stomach was full.

Drooling.

The room smelt if it.

"I can't I..I can't!"

I whimper out. Drooling milk down my chest.

"Then you've failed me. Like you failed Jessica. Now you have to give it all back for me. And at the same time cleanse yourself of her.

Gag yourself on the dildo. Wretch it up for me ON to her photos. Disgrace yourself like you did the minute you two started your fling. "

I lean in and start sucking and going down on the dildo.

I know she is watching but what I didn't see.. was the Teamviewer screen had changed from a sissy trainer video..to Facebook.

And she has looked up Jessica's page.

As I loose it and puke up the white milky filth all over the photos. A message is being typed.

"Jessica! Hey! How have you been? You've been on my mind today. I'd love to catch up and tell you all about it!"

As my watery eyes compose I look over and see the message go from text to SENT.

Then on the desktop I see a new folder labeled Jessica's Session with screenshots of this debasement in it.

Mistress laughs..

"When she replies I want you to unfriend her and not communicate with her at all. And you'd debt for her to me is paid."