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Major task 1

Posted 01-16-2018 at 01:53 PM by Humiliationsub
Updated 01-16-2018 at 01:59 PM by Humiliationsub

On December 15th I completed my first major task set by my master. I hadnít cum since November 21st and had been promised that doing the task and following the instructions would result in me cumming.

The first part of my task was to buy the following items:

Bra, panties, hold ups, cucumber and lube. Master specified some items:,pd.html

I purchased the items that he had requested. I took them to an attractive young cashier called Rachel. Iím not sure who was more embarrassed as I made my purchase. She wouldnít make eye contact with me, but I knew my face was red and I had mixed feelings of being horny, excited, humiliated and nervous all at the same time.

I drove home excited at the thought of what instructions from my master would be waiting for me. I got home and rushed to check my messages. I found the following instructions in my inbox:

1. first get all your items and take them home, you seem to have a plan so go with that

2. Still no touching yourself but if you start dripping pre-cum, collect it in a glass.

3. Get all dressed up in the bra, panties and stockings

4. Now, do a sissy photo shoot, take many pictures in different poses.

5. Get that cucumber and show it your best blowjob technique; slobber over it, deepthroat it etc.

6. Next your boipussy, lube up your fingers and play with it. See how many fingers you can fit in. Still no touching yourself and make sure to catch that pre-cum.

7. Hopefully it should be stretched at least a little, cos now the cucumbers going in. Lube it up and slowly insert it.

8. Start sliding it in and out, getting faster and deeper. Can you get more in inches/cms in your arse or mouth? Find out for me.

9. Do that for a while, really make sure you enjoy it.

10. All of this should have you super excited. Get your pre-cum, sip a little, taste it, swallow it, then pour the rest over your face.

11. You mentioned a method making sure you cum over your own face in a forum post about a week ago, now that's coming back to haunt you! I know you could do it without, but it is much more fun with.

12. You are going to get one of your wife's favourite dresses and place it behind your head as your raise your legs and clitty in the air over your face. Try and keep the cucumber in when you do this so it looks like some sort of weird buttplug/flagpole.

13. Now the moment you've been waiting for, you can start stroking. Jerk that clitty until you spurt over yourself.

14. Swallow any that lands in your mouth and leave any on your face for at least 30mins-1hour, same with the clothes, but you can take the cucumber out if you wish.

15. Throughout make sure that any room youíre in has the blinds/curtain's open, so pick your rooms carefully.

Oh! I almost forgot the most important part!

16. When it feel yourself start to cum, hands off! Ruin it! If the cucumber is still in you can play with that and try and make it a sissygasm but no touching when you finally cum! It'll be tough, but I know your strong enough to do it Amy! I believe in you!

I have to admit that just reading the instructions and having the situations flash through my mind, nearly made me cum in my pants. I had to quickly walk away from the instructions, think about something else and compose myself. After a few minutes to calm down, I set off to carry out my task.

I dressed as requested and took some pictures for my master. I spent the whole time collecting my precum in a glass. I then moved on to giving my cucumber a blow job, this was very humiliating for me.

I then lubed my cucumber up and started to fuck my boi pussy with it. This was a fairly new experience for me as Iíve not had a lot up there before. I tried hard to get as much as possible in, all the time collecting my precum. I then took my precum, drank a little and poured the rest on my face as instructed. As it started to dry, it pulled the skin tight on my face. Once dry I moved onto the next part of the task, which was laying my wifeís dress on the floor, placing my head on it and jackknifing my body so that my sissy cock was pointing at my face. The dress was there to ensure I took the full load of my cum in my mouth and on my face as I couldnít risk any going on my wifeís dress. This is the point Iíd being building up to for nearly 3 weeks. I think it took me just 2 or 3 tugs on my clitty before I felt my massive load about to spurt. I quickly removed my hands and ruined myself into my mouth and onto my face. Iíve never had such mixed feelings and emotions. I let out an enormous groan and felt total and mental relief as the cum started to shoot on to my face and into my mouth, these feelings were quickly replaced by the frustration and desperation of realising that my orgasm was ruined and not delivering me the satisfaction and relief that Iíd been craving for the last 3 weeks.

I lay there for about 30 minutes as instructed, thinking about my situation and replaying it in my mind to ensure that I remembered every detail. As I did this, I started to get hard again. I ruined myself into my glass with the precum dregs. I knew that master had only instructed me to cum once, but it had been so long for me without cumming and such a mentally and emotionally overwhelming day that I just HAD to cum again. I hoped that by ruining it and drinking it, master would understand and go easy on me. I write this part of my blog with some trepidation as when I reported this to him at the time, he said I must be punished, however I think he had forgotten. Iím sure that when he reads this, heíll remember my outstanding punishment.
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