A Lost Bet Ch. 01

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"Please, just let me up. I promise I won't say anything to anybody."

"You're damn right you won't. If you do, you have no idea what will happen to you. We tried to make this enjoyable for you, but you just won't stop begging like a bitch." Frank was obviously getting tired of my pleas for help. "You know, I was going to let you up, but instead, I think I'll just leave you here with my special friend...the machine."

"Frank, I didn't even know you had one of those. I always wanted to see one."

"Well, gag Jo while I set it up." And the ball gag came back. Then, I felt some pressure on my ass...again. I looked up and Tom snapped the head rest back into place. He said "since you're going to be here for awhile, you might as well be comfortable." Then Frank shoved the dildo attached to what looked like a large drill into my ass.

"Jo, this is 'the machine.' I'm going to turn it on and set it for 30 minute increments. That means, it will fuck you for 30 minutes, then shut off for a random period of time. At least for the first 3 cycles. After that, it's all random. Oh, and one other thing. Actually two. First, over the course of the night, you'll find that the dildo changes size at random. It's inflatable. It won't get much smaller than it is now. Stop shaking your head. Right now it's my size and I KNOW how much you enjoyed riding me. But it will get larger. The second thing is that it's hooked up to an ejaculation mechanism. That is, the machine will cum. It's kind of a mix of cream and water. That will help keep you clean and lubricated. I imagine that by the time we come down in the morning, you'll really have to go to the bathroom, but there shouldn't be too much of a mess. Are you ready?"

I was furiously shaking my head no as tears ran down my eyes which were pleading for them not to do this to me. Then they switched the machine on and I squealed like a girl. I grunted as the machine pumped into me. They watched for a few minutes, until I passed out. I remember waking up periodically through the night to the pumping, but also to periods of calm before the whole process began again. I couldn't understand what had happened but I knew I wanted things to end. But when would it?

To be continued...

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AnonymousAnonymousover 1 year ago

Well, I would have been so pissed that coming back and burning down the house would have been so much fun. With friends/buddies like these, who needs enemies. No telling how much blackmail will be involved if he lets them get away with this. Oh well, there are a few more chapters so I take it he is going to be taken down a long dark path of humiliation and degradation. He will probably need to wear a diaper for a few days after being strapped and fucked all night long.

PervymacPervymacover 3 years ago

Really enjoyed the story, got seriously aroused imagining being Jo!

AnonymousAnonymousover 6 years ago
4 stars not 5.

I gave you a 5 stare rating but after second thoughts I would have given it a 4 star rating..The story is good just long and slow.

zazrix9zazrix9almost 7 years ago
OMG

I'd luv to be that lucki guy

AnonymousAnonymousover 7 years ago
hot story

yes been a while but had to cum back and read this story again....so frigging hot

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