SimSissy Pt. 09

On Monday I woke up, I dressed and checked my messages, only important one was from Paul, he had paid me and he had really enjoyed the weekend with me and he thanked me once more for the library of files and speeding up his computer. He wrote that he would love to see me again and if he didn't see me today he would surely jerk off to the pictures of SimSissy and the memory of Sunday.

I suddenly remembered that Paul had put something in my back pockets, I quickly checked it and there was another note of 50 euros and a note telling SimSissy to buy something nice like a butt plug. I grinned and thought I should indeed buy one. I had seen some other nice things at The Sissy Market and I decided to order them at once.

The day turned over pretty boring, I had stashed my clothes away before my parents returned, I had cleaned up everything and maybe it was because of Paul and his listening and fucking skills, or that I hadn't heard anything new from my blackmailer, I was at ease. My parents noticed and commented on the fact I looked good, they were glad. I could honestly say that school was doing well and that my little company was still in business. That I even had done a job last Sunday fixing up some old guys computer.

At night no new messages from the blackmailer, just a little message from Paul to which I replied quickly. Another day was gone by and again I fell asleep easily.

On Tuesday the thing I dreaded finally happened. A new message from my blackmailer.

"SimSissy, hope you enjoyed your time off. Vacation is over. You have three days to finish the next task. Paint your toenails. During the next three days you will receive a text with either left or right at a random time. After receiving you will send proof of your painted toenails by making a picture. Timestamp of the picture must be validated with a watch visible in the image. After each text-message you have during school a two hour time-window, outside school one hour. No BORING painted nails!. You start Wednesday."

Okay, somehow I was glad, this was do-able and not too public, also not as restrictive as the cage I was wearing. Still, I feared that if I did them simply white, light pink or red, that would be considered BORING". I decided to mail the assignment to Paul, maybe he had some good idea's. Right now I had all day to think about it. Maybe also buy some extra nail-polish?

When I was almost done with school I saw I had received and e-mail from Paul.

His idea was to paint them in Hot Pink and put some text on them like SISSY or CAGED, even better SPERM or other five letter words like NASTY BITCH DIRTY COCKS PENIS LOVER or whatever. That would indeed not be boring and absolutely not something I would want to be discovered.

On my way home I bought several colors of nail polish including of course Hot Pink at the HEMA and I returned home. Nothing screams Sissy more than Hot Pink.

At my room I cleaned and polished my toenails, they were already clipped nicely and I started painting them. Next I decided to start with CAGED SISSY readable on them. After I had painted them I stripped naked, sat on my bed and pulled me feet close, and I shot some pictures with the focus on my painted toenails. I looked if my ass and cage were blurred but visible and sent them to Paul. His response was that he would love to fuck Caged SimSissy senseless again, I responded that I would see if I could make that next weekend possible. After letting the clear overcoat dry I finally went to bed, the first day with assignment nr 8 was to start.

At 6:30 I awoke with the ring of a text-message. Of course, that early.

"LEFT RIGHT IMMEDIATELY, FIVE MINUTES."

I was glad I had already painted them yesterday so I bent over, placed my wristwatch next to them, shot a picture and send it to the mail-address. A simple OK arrived two minutes later. I briefed Paul and I got myself ready for school that day.

During the day at school I received two more texts and in both cases I was able to make and send them within an hour. Later at home I received another text, also the assignment to change them with new text on them. So at night I cleaned them, repainted them and now I wrote NASTY BITCH on them. Paul loved my pictures.

Next morning, again at 6:30 a new text, again only five minutes of both. I decided to put my watch on my foot and shoot a picture with my nightgown just covering the cage and the feet visible. The rest of the day went by with also two more pictures during school. At evening it was a little bit trickier because I was at work picking up someones computer for cleaning and upgrading. The lady just kept talking and talking and talking about her dogs and her friend and oh, finally I was in my car. With just 15 minutes left I decided to simply shoot the picture in the car so I parked a couple of 100 meters farther away, I took of my shoe and sock, snapped the picture, send it, retied my shoe and returned home.

At home I received a new e-mail. "Keep it up SimSissy, new text tomorrow".

I had already thought about it and started on them. Again hot-pink, now I wrote SPERM LOVER on them, and I drew some white droplets on them also, as if it was cum. So glad I used to paint miniatures for DND so I could definitely paint a little.

Next morning, again at 6:30, I shot the picture of my painted toenails and send it to my blackmailer. And again like the days before, during school two requests. One last request arrived when I was at home. And quickly after that I received a new e-mail.

"task Eight complete, scored 8 points : Nails painted OK, Not boring OK, Send pictures on time OK. No errors on left right OK, photo-locations outside school, Not OK.

Bonus points for spicy text on nails, 2 points.

Punishment points for Thursday teasing and not following up on Friday points, -5 Points.

Total Score = 5 points."

What, I lost five points, because I teased on Thursday and I hadn't continued on Friday. No, shit, no. I checked my pictures, so I got punished because I teased only once, this wasn't fair. I thought about it, okay, maybe I could undo the punishment. I decided to sent a new picture with a sincere sorry. I stripped and laid on the bed on my back, bended my knees and put my feet towards my ass, I laid my watch down so the time was visible, I shot a new picture, clearly showing the painted nails and text but also my cage. I send it to my blackmailer with a text.

"I am so sorry, I had not thought about it and didn't realize I was teasing, please accept this as a punishment instead. I would have send this instead if I would have thought about it."

I hit send, dressed up, and waited.

After five minutes I received an answer.

"Apology noted, this photo would have been accepted if it had been sent in the morning. You will receive five more points punishment for attempted bribery!"

What, NO, oh no, Please no, My first reaction when I read it.

I counted quickly, instead of 63 points and needing 7 I now was at 58 again and I needed 12.

Wait, I received a new e-mail.

"SimSissy, keep your toenails painted properly in a nice steady color next week. You will receive a random text to send a picture of both feet, timecode necessary. If you comply and don't fail, you will get five points returned.!

Tomorrow you will receive a new assignment."

Okay, that was a kind of relieve. Being blackmailed was both bad and exciting, I loved that someone was in control and had made me do things I would never have done myself but I did love them, still, the threat of being exposed was a very oppressing feeling. I wanted to be rid of that as soon as possible and those extra five points, I needed them, I wanted them.

I mailed Paul about everything and he mailed me back he had good hopes I could regain thos five extra points. He also invited me for the weekend, he would love to Suzanne to dinner. I mailed him back that dinner did sound tempting but I felt scared that someone would clock me and expose me. I also didn't know if next weekend was possible because I didn't know anything about the new assignment yet. After that I went to bed and fell quickly asleep.

In the morning when I woke up I checked my mail. A new assignment indeed, and of course why did I feel I was fucked up again.

"SimSissy, it's a perfect day to go to the woods today. I want a dressed up picture of you like you were in the park, I want also a slutty picture of SimSissy in the woods.

Also since you like texts so much on your toenails, you will write Sissy texts on your naked body. Lipstick allowed, texts NOT in mirror!!. Pictures must be in before 22:30, failure or not compliant pictures will give you negative points. Don't forget that I own you SimSissy"

Okay, fuck, this was a whole new level of exposing myself. Now, how would I do this, I would need to find a forest that wasn't visited, not public. I needed, to carry my equipment, a tripod, my camera and a remote of course, okay, taking the pictures would be okay, but the forest, where. I checked the maps, there was forest enough, some national parks like "De Peel" had some silent spots. Or should I try one of the places were gays tended to park and have sex, no, no definitely not. That scared me. Okay, what if I would go to the forest near were Paul lived, and then ask Paul to help me. Especially with the writing. I would take my laptop with me and I could send everything right on time.

I opened Teams and rang up to Paul, he answered quickly and he was already neatly dressed.

"Hi, good morning, did you sleep well?"

"Yes Paul, thanks. You too I hope? Hey, I have heard again from the blackmailer, I got a new assignment and I think I could seriously use your help. He wants pictures of Suzanne in a forest but also pictures from SimSissy, oh, and ehm, you need to write text on my body. Now I thought about your forest nearby, is that usually crowded? "

"Oh wow, what an assignment, I will help you of course, and the forest, I think it will be okay, its pretty boring, not very touristic I think. Yeah, I might now a couple of places. Do I need to get anything for you?"

"No I got everything here I need, I will dress up, pack up and come to you, be there in I think ninety minutes."

"Okay great, oh wait, maybe if you don't hang up, keep your video on while you dress up? So I can watch?"

"Sure Paul, I'll leave it on, keep watching, like the Jennicam? I looked her up, she was brave"

Next half hour I was dressing up, putting on the wig, makeup, getting clothes for SimSissy, I also took a nice dress for the dinner but I wasn't sure about that yet. Still, better safe than sorry. When I was finally ready I waved to Paul via the camera and I left. About an hour later I arrived at his door and I walked in. He hugged and kissed me, and asked if I was ready, he had found the perfect spot for taking some pictures.

Next half hour I was dressing up, putting on the wig, makeup, getting clothes for SimSissy, I also took a nice dress for the dinner but I wasn't sure about that yet. Still, better safe than sorry. When I was finally ready I waved to Paul via the camera and I left. About an hour later I arrived at his door and I walked in. He hugged and kissed me, and asked if I was ready, he had found the perfect spot for taking some pictures. Paul showed me a bag, "And lets make it a fun picnic."