Gambling with Mistress Tara

Mistress Tara was relentless ever since I admitted my weakness for gambling. It’s certainly gotten me in trouble in the past, but from the way she looked at me I knew that more trouble was on the horizon. Our sessions had changed since that day and she made sure to include gambling in all of them, obviously getting a kick out of how much more turned on AND frustrated this made me. The first session since my revelation, she had me tied up and facing the wall, my bare back exposed. She took a 10-sided die and told me that it would determine how many strokes my back would get from her crop. I was also given the option of a 20-sided die with the same rules, except that if I rolled a one, I’d be allowed to kneel and jack myself off to orgasm in front of her. Needless to say, my desperate self chose the latter, opting for the 5% chance of cumming while putting myself at risk of potentially twice as many lashes. With a giggle, my busty blonde Mistress rolled the die across the floor, a more spirited laugh heard seconds later. Clearly I didn’t roll a one.

“Forty-eight! Well, aren’t you the lucky little bitch boy?” I wasn’t sure if I was expected to answer, but before I could open my mouth anyway I felt the first lash come down on my back, leaving stripes of stinging pain. I was in tears after a dozen and begging by twenty. I passed out before the last of the 28 lashes was delivered. Mistress Tara slapped me across the face to wake me up, giving me a playful pout, “Poor bitch boy, was that too much? You pretty much asked for it, you know. If you weren’t such a greedy pervert you could have gotten away with just ten at the most, but instead you let your achy little cock and balls get you into this mess.” She pretended to be thinking things over, but I knew she’d done it beforehand, “Ooh, I know. I’ll give you one more chance to cum if you roll a one. If it’s another number, that’s how many orgasms you have to give me before I even consider giving you a chance at stroking your cock. That means you’ll be locked up in between rolls.” Pitifully, I agreed.

With another gleeful giggle, Mistress Tara announced that she rolled a 12. Untying me, she lounged back in one of her chairs and spread her legs, wordlessly letting me know that my tongue was expected to be put to use. I managed to bring her to 8 orgasms before she told me our session was over, and she looked quite exhausted herself. As promised, she locked my cock into a chastity cage, which I realized I’d have to wear all week until next Saturday’s session. I’d never actually been in mandatory chastity before and it was much worse than I expected. I was used to jacking off daily, so going a whole week was truly torturous. Worse, I’d have to spend a good chunk of the session time bringing Mistress Tara to four more orgasms before I’d even get to roll again. Naturally, I did, and she laughed at my expression when I was finished; I could only imagine how desperate I looked. It couldn’t have been any more pathetic than I looked when Mistress Tara proceeded to roll a 16, however. Just like that, my head was back between her thighs, and I was spending $600 for a session where I did nothing but bring my Mistress to 15 total orgasms, including the four from the start. That meant another week of chastity and five more orgasms for her at the start of next Saturday’s session.

My pussy-licking skills were improving, as I got her to those five orgasms faster than I expected, not that she showed any signs of being impressed, “Do you really want me to roll again? I’ll let you out of the cage if you don’t, and you can jack off at home. However, this time I’ll let you jack off here, on the floor, in front of me if you roll a one OR a two.” I squirmed nervously, balls aching for release, but all I could think about was stroking my cock in my Mistress’ presence, which would be one of the best orgasms of my life, certainly. I nodded and she grinned wide, giggling with faux-innocence. She reached into her bag and took out what almost looked like a ball. When she rolled it across the floor, I realized it was actually a die, and definitely not the 20-sided one we used previously. Leaning down, she peered at it before looking at me with a more predatory gaze, “Well, would you look at that? 89!”