I hesitated. Rolling the die was going to determine a daily task for the coming week. Seven rolls, seven tasks.
We had been playing this game for a month. In that time I had spent many days in chastity. I had spent days wearing Mistress’s dirty panties. I had days where I had to kneel four times while at work and send Mistress photos. I had days where I had to ask permission for all my bathroom needs. I had even spent a day wearing all of Mistress’s toiletries – her floral deodorant, her apricot-scented body lotion, and even a dab of her favorite perfume. Over the course of the month, many tasks had shown up more than once. Some tasks I had never done because I never rolled that number. But overall, I had performed more than a dozen different tasks – each one chosen to make me feel more submissive, more aroused, more humiliated, or more obedient.
And now it was time to roll for the coming week. Mistress handed me a card with this week’s options in writing and the tasks seemed daunting:
1 – Bend over and take Mistress’s strap-on up the ass twice – once before work and once at bedtime.
2 – Wear a special pair of Mistress’s panties that she had worn for 72 hours just to make sure they were ripe with all her scents.
3 – Sit on the potty each time I had to pee during the day.
4 – Compose four poems, each at least 3 verses long, on the themes of my sexual inadequacies – having a small penis, struggling with erectile issues, and being a premature ejaculator.
5 – Refrain from using any first-person pronouns in all my emails and texts with Mistress. I could only refer to myself as: “this slut”, “this pervert”, or “your mini-dicked preemie”.
6 – Orally worship Mistress’s ass for 30 minutes before bedtime.
In addition, For any day that I rolled an odd number, I would be allowed to try to cum but only if I could do it within 3 minutes while humping an item chosen by Mistress. And for any day that I rolled an even number, I would be required to edge four times but I wouldn’t be allowed to cum at all.
I rolled the die and my week was planned. Four days in a row with even numbers. I would edge repeatedly but never cum. In addition, I would be wearing really dirty panties to work one day, composing poems of my sexual weaknesses, and worshipping Mistress’s big, beautiful ass two days this week. Some of these would be quite humiliating. Some would be very arousing. And none would lead to any sexual relief. Just humiliation and frustration.
That would be followed by three days where I rolled odd numbers. I would get to hump something and try to get a cummie. I would also spend a day avoiding first-person pronouns and I would get fucked up the ass multiple times.
The first four days of the week went by slowly. The multiple edges and and two days of worshipping Mistress’s ass left me insanely horny and needy. Mistress did allow me to hump the mattress while eating her ass, but since I wasn’t allowed to cum, that only lasted about a minute before I had to stop or I would have soiled the sheets.
The days also had their fair share of humiliations. Those panties were ripe with the fragrance of pussy and sweat after being worn for three days. I felt positive my co-workers could smell me so I did my best to keep to myself all day. To add to the humiliation, Mistress made sure to tell me she also peed herself just a bit on the last day she wore them just so I would have some of her dried-up piss pressing between my legs, as well. By the time I took those off that night, it was a relief.
The day of writing poems was challenging and embarrassing. I’m definitely not a poet so my poems were the most basic rhymes. And it took some effort to compose four poems of three verses each. I spent a lot of time in my day focused on writing about the things that are most humiliating to me. When I finally finished and gave them to Mistress, she just took them and walked away. I assume she read them in private. But they were never mentioned. And that just added to the feeling of being so emasculated and submissive that even my best efforts weren’t always even worthy of recognition. To underscore one of the lines in my poem…”is that all?”
The last three days of the week held more promise! I would have a chance to cum every day. I was so excited and so needy!
One day was spent with one of the most challenging mental tasks I’ve had in quite some time. I send emails and texts to my Mistress all throughout the day while I’m at work. And I had to write and then re-write so many sentences just to get rid of first-person pronouns and replace them with the proper phrases provided in the task. It was quite difficult. But I did it…and was looking forward to the chance to cum.
That evening Mistress pulled out the timer on her phone and set it for 3 minutes. Then she handed me a soft pillow and told me I could hump it. Unfortunately, I could not put it on the floor or the bed and lie down on it to hump. I had to kneel by the wall, place the pillow between myself and the wall, and with my hands behind my back, try to hump it to orgasm. It was a disaster and I felt foolish. It felt great to push against it. But the moment I pulled back for the next thrust, it would fall to the floor. I had to ask permission to use my hands to pick up and put it back in place. And try again. And before I ever sorted out any rhythm or way to make this happen, the timer rang. Another day of frustration.
Then for two days, Mistress used my ass. Being fucked in the ass always has a lot of feelings for me. It feels…embarrassing. Vulnerable. A bit painful. Stimulating. It makes me want to cum but I don’t quite get there so it is also very arousing and frustrating. And Mistress always talks while she does it…combining some mind fucks with the ass fuck as she reminds me I’m her little ass whore. Telling me how I’m just an ass slut…loving to eat ass and get fucked in the ass. And the humiliation and arousal just go through the roof.
So I was so ready the second evening when the time came to hump. Mistress gave me the same soft pillow and admitted that she made things too difficult the night before. This time I was allowed to put it on the floor and get down on top and hump just like if I were fucking.
Except.
Mistress said I wasn’t allowed to touch the floor with my hands or feet. So I tried to balance on elbows and knees which made it really difficult to fuck the pillow. And it was so soft that I really had to hump hard to get any friction. And three minutes were over long before I could get myself off.
More frustration.
I finally made it to Saturday night. After another day of being a hole for Mistress to fuck, I had my final chance to cum before rolling the die for a new week.
This time there was no pillow. Mommy told me I could kneel right in front of her and hump her leg like a horny little puppy. She was wearing shorts and was barefoot so I would be able to rub right up against all that bare skin. This was going to work!
The timer began and I started to hump. Mistress held her leg pretty still but it still bounced around a bit. It wasn’t easy getting the friction I wanted. And for once, I was almost glad to be a premature ejaculator because I would never get there otherwise. But I could feel it happening this time. It was so close. SO CLOSE!
And it happened! I started to cum! And at the very first contraction in my penis and the first little squirt of my mess, Mistress kicked her foot and got me right in the groin. I fell over sideways, feeling the pain in my testicles. And falling caused me to pull my penis away from her leg…leaving me to dribble cum all over the floor in a ruined orgasm. I didn’t feel any good sensations as any moment of the good feeling was overpowered by the pain in between my legs.
As I caught my breath, Mistress looked down with pity.
“I’m so sorry I kicked your little scrotum, baby. I know that must have hurt. I didn’t mean to do it. But your little squeal when you started to have your little cummie startled me and I just flinched. I hope that didn’t keep you from enjoying your squirt. You surely worked hard all week and deserved it!”
I slowed my breathing enough to get out “Thank you, Mistress.”
“Now, lick up your mess off my leg and the floor, then you can come to sit beside me and watch a bit of TV before we roll for next week. It’s always so exciting to see what you’ll be doing. I think next week will be some of my most creative ideas yet!”
As I began to lick up my mess, I felt my little flaccid penis twitch a bit. Submitting to my Mistress never failed to excite me and I was ready to embrace a new week.