A Lost Bet Ch. 06

I yelped at the cold liquid being let loose inside my rear until I felt a new pressure. Mark had his cock pressed against my hole and was slowly...slowly entering me. He pushed against my hole and my ass expanded. My breathing increased as I tried to accommodate him, but he kept pushing and I'd never felt anything that wide before. I tried to adjust and I heard myself say "too big...too big...never had...anything...like you..."

"I thought you'd enjoy the surprise," Mark said and I could almost hear his grin.

A couple of tears escaped my eyes as I tried to cope with his size. "God, Mark. How big are you?" I managed to choke out.

"Almost the size of your wrist." My eyes snapped open as I looked at my wrists stretched in front of me.

"No way. No way." I couldn't believe it. I mean, it's not like my wrists were huge or anything. They were actually kind of all the small side for a guy, but still, Frank and Tom weren't that wide and I'd been unprepared for him.

"Just a little more," he said as he continued to push into me. The pain started to turn towards pleasure, but the pressure was unbelievable. I felt him deeper in my bowels than anything (except for the dildo at the show...maybe) and I was starting to shiver from the exertion. "That's it Jo, that's it. You're doing fine. As a matter a fact, I think you're in for a helluva ride." And with those words, he started to slowly pump in and out of my ass. My cries echoed off the basement's walls...random sounds like "ooohh" and "aaahh" and moans and a couple of choked sobs...until finally, the pleasure overwhelmed the pain, and a steady stream of "yes" and "oh Mark" became the norm.

Because of my position, he was pumping up into me, and my feet were pretty much lifted off the floor. It was almost like he was holding me in the air while fucking me and it brought new feelings of vulnerability to me...along with tight arms and legs. The minutes passed and Mark started fucking me faster and faster. My cries got louder and louder, the pitch higher and higher until I was practically squealing as I rode Mark's pole (best description of what he was packing). I couldn't stand it any longer. I began to cum and I saw my cum shoot in front of me, falling on the cross. Finally...he came. Jet after jet of cum emptied into my ass as he continued to pump in and out, until with his last exertion, he planted his dick hard in my ass and my mouth opened in a silent "O" as I stared at the ceiling in extasy, seeing nothing.

"Oh God...oh my God...I think I'm dead." I tried to get a sense of what was going on, but I felt utterly disoriented. Alex was laughing in the back at my reaction, and I could almost feel Mark's smile. With an audible "pop" he pulled out of my ass and my body went limp. I could feel his cum draining down my leg as I slumped on the bonds securing me to the cross.

"Ah, ah," was Alex's comments. "I don't think we're quite through with you yet." I looked up in surprise because I was sure they couldn't have more planned for me, not after that. I watched helplessly as he went and pulled the chains. Now, I truly was stretched against the X. Had it not been for the restraints, I most definitely would have fallen in a pile on the floor.

"That was a good warm up. Next time around, I'll definitely have more staying power," Mark said.

"What, like 30 minutes was too short?" Alex commented. "You were just too excited to get in her ass."

"True, true. And it was a delicious experience," Mark responded. "Jo, I think Frank and Tom did you a favor by putting you in this position. I mean, I'm sure you're a great guy, but you are an amazing chick. Shoot, we might even give them a thank you card." They both laughed and I smiled, but I still wasn't too sure about whether or not I shared their sentiment. I pushed the thoughts aside and resolved to deal with them later.

"Well, I'm glad you're enjoying yourselves. But, can I request a change of position? My arms are getting a little sore." I tried not to whine, but I couldn't help the pleading tone in my voice because my arms were starting to feel like they were on fire.

"Sure Jo, in just a second, we'll let you down. Just...hang on," Alex collapsed in laughter at his pitiful humor as Mark and I both groaned. Mark finished cleaning himself up and getting his pants back on straight.

"You know, I'm kind of thirsty." Mark looked over at Alex. "You want a drink?"

"Actually, I would. Jo, would you like something to drink?" asked Alex.

"Umm. Yes, I think I would." I was skeptical about what they had planned and was trying to figure out whether my choice was the right one.

"Fine. We'll help get you ready." Mark replied, but he walked away from me. I couldn't turn my head that far around so I didn't know what he was doing. "Don't worry Jo, we're just getting a chair for you." I felt some relief at those words, but it would last long. I heard them positioning the chair and then felt them come over and release my hands.

"First things first," was all that Alex said as he unchained my wrists and removed the cuffs. He positioned my arms behind me so that my arms were bent at the elbow and my arms were crossed. Then he tied my arms together, hand to elbow, which forced my chest forward as my back arched. "Okay, hold on to this button. We told you we wanted you to be safe, so only press it if you feel like things are going too far. One or two more little additions up top." Alex fastened a collar around my neck which forced my head stay up. I could no longer look down and see what they were doing, although I could still turn side to side (in a limited fashion).

By this time, my ankles had been uncuffed from the X and Mark had positioned the chair behind me. After Alex finished with me, Mark lifted me up and set me on the chair. As he did, I felt myself being penetrated by the chair.

"What the hell? What kind of chair is this?" I asked.

"It's a chair with a couple of little modifications," Mark said as he then pulled my legs together and started binding my knees together and my ankles to each other. "For instance, you felt the dildo enter your ass, right?"

"Yes."

"Well, it's not just a dildo. It's also a...special kind of enema delivery system." My eyes grew wide as I started to wonder what kind of discomfort I was going to be experiencing. "You see, with this system, you're in control. You have some measure of control over how much liquid gets forced up your ass."

"Okay, so how do I control it?" I was anxious to figure out what I was going to do, and why all this was necessary in order for me to get a drink.

"You suck on this," Alex said as he slid a penis shaped gag into my mouth. "Mmmpph..." was all I managed to get out. Alex held up a tube hanging from the end of the gag. Mark wheeled over a cart with two bottles on it. Alex attached the tube from the penis gag to the smaller bottle, while Mark attached a tube from under the chair to the larger one.

"It's simple really," Mark commented. "The more water you suck, the less water gets forced up your rear. But when you stop sucking, the pump kicks in and water goes in the back door. So, you may want to pace yourself."

There was nothing I could say as I watched them flick the switch and turn on the pump. Immediately, I felt liquid filling my insides, and they were filling fast. I started to suck, but I couldn't find a good rhythm. I turned my head as much as I could to look at them and plead with my eyes to have them let me go. But they only looked back at me with smiles on their faces. "We'll be back in a few minutes. We're gonna get some drinks, call a couple of friends and come back."

With a petrified look on my face, I watched them walk away and tried to figure out what they could possibly want to do next before I resumed sucking down my water and filling myself up like a balloon. I was starting to wonder if maybe I'd gotten myself in over my head, but I had the panic button and knew I could stop it all if I wanted to.

The question was, did I want to?