Some More Money Ch. 01 - Trespassing

He lifted my legs straight up in the air, held them there with his shoulder, took my wrists and placed my hands on my calves near my ankles. "Hold 'em raht here." He pushed my feet toward my face, pressing my knees tighter on my chest, then he spread my knees so they framed my boobs. "Yew hold 'em taht, jus' lak that." He was gone for a moment. I didn't know why until I saw on the final video he was coating the first six inches of his cock with lube.

He touched my ass with his tip. On the video, the hugeness of his cock next to my tiny hole was almost comical. If you ever see the video, it will be quite obvious, that thing is never going to fit in there. No freaking way, even with my butt pre-loosened with the plug I wore, even with it pre-stretched with three fingers. Unfortunately for me, the one person it wasn't obvious to was Cyrus; he clearly intended to make it happen.

It didn't start well. He pressed inward, oblivious that the task was impossible. I tried as hard as I could not to tense up, but I did, I couldn't help it. He pushed and pushed, and somehow he got the tip into me. He didn't get very far; he pressed harder anyway and got nowhere.

"Yeh need to poosh out, lahk yeh was tryin' ta crap me out," he helpfully suggested. I tried it -- shoot, it couldn't make things any worse.

He pressed again, and actually got a bit more in. I was braced for searing pain, and it did hurt, but it was more of a dull ache than a sharp stab, not nearly as bad as I feared. 'Pooshing' like he suggested seemed to help, maybe, a little.

He stopped pushing, but didn't pull out. He held still, giving me a moment to adjust to his size. I was actually able to relax, a bit. He didn't have much length in me, but he had his entire girth in past my outer ring, and my body was already adapting, accepting it more than I thought possible.

He began a regular, slow-paced thrusting rhythm. It wasn't in and out, he didn't have enough length in me for any 'out' yet. Each push was inward, entering me a bit more, an eighth of an inch this time, a quarter of an inch the next, then another eighth.

He gripped my butt cheeks, spreading them apart, showing both cameras that he was in my ass past his cock head. He pressed upward on my legs, massaging my thighs. He rubbed back down to my butt, squeezed both my buns hard, spread them apart again, caressing them deeply, all the while sliding more length into me, tiny bit by tiny bit.

All that tender attention, in addition to his fingers earlier and the amount of lube in my ass and on his cock, as well as the 'pooshing' I was doing, should have relaxed me to where my rectum accepted his pole without any discomfort. It didn't. I wasn't in agony, but I was far from comfortable. I seriously considered bailing, ruining the video, getting his fucking monster out of my ass, going back to my hotel room, packing up in defeat, and returning to my waitress job. This just wasn't for me. I was sure Ryan would refuse to pay me anything, he'd cancel my plane ticket so he could get a refund, and I'd have to pay my own bus fare to get home. Financially it would suck, but I would be free of having anything huge up my ass.

Then I remembered something I read online before my first shoot. It was an article on ass-play, A Naughty Girl's Guide To Butt Sex. The point of the article was, your body can accept almost anything you want it to, but you have to consciously decide you want it to. They quoted a famous porn actress who said, "A dick will hurt like crazy if you resent it being there, but that same dick can actually end up being quite pleasant if you tell yourself it's okay, that you want it there."

As Cyrus continued his thrusting, gradually getting deeper and deeper, I thought, 'Why would I want any dick up my ass, but especially this one?' My first answer was, 'Duh, $4,000.' That wasn't a bad reason, but maybe not enough to cause my butt to relax for such a huge intruder. I thought a little further, 'I like Ryan, I like working for him. I like the money, I like the possibility of not having to wait tables any more, and I definitely like not worrying if a couple of slow nights at the restaurant will mean I'll have to be late on my rent -- again.' The next logical link in that chain was, 'Taking dicks up the ass is a part of working for Ryan. Maybe it's not so bad, even getting speared by a freak like Tom.'

While I was off in my own world thinking, Cyrus was going to town getting deeper. I had distracted myself from the distress back there, and damn if it actually didn't feel that bad. Could that porn actress have been right? Could such a simple psych-out mind trick make that much of a difference? I was amazed, to say the least, to realize it just might.

Cyrus reached what I guess was his target depth, and he began to pump me in and out. Watching the video later, he wasn't anywhere near bottoming out, it was obvious even to him that was never going to happen. He was reaching somewhere around the depth of a 'normal' cock, and I'll say this, it felt pretty freakin' deep to me! He was beginning to fuck me for real, blissfully unaware of any distress I might be feeling. I was astonished not to be in an ambulance on my way to have a ruptured asshole surgically repaired. More amazing than that, though, I was remarkably comfortable, or at least not uncomfortable.

The cameras were on either side of Cyrus, and with me on my back, they had different views of his dick entering and exiting my ass. One was close-up showing nothing but my ass filled with his dick, my empty (and uninjured) pussy, and a bit of my tummy. The other one, viewing me from the other side, was wider, showing all that plus my boobs rocking and rolling in time with his thrusting. Both shots showed my empty slit being stretched into a bit of an O shape as his dick entered me, relaxing into an elongated slit as he exited. My crinkly inner lips peeked out from within as if seeking some attention of their own, emphasizing how unused and ignored that opening was.

I was just beginning to think, okay, maybe I can do this. Maybe I won't bail, ruin the video, and return to waiting tables. Maybe I can finish this. That was when Cyrus pulled out of me. 'Now what?' I thought. I feared that now he was going to spear my pussy. I also worried that what he had done so far was just a warm-up, and he was going to return to my ass to get serious and go deep.

What he did was pull up on my hips and turn me over onto my hands and knees. He didn't give me any time to adjust, he plunged back into my ass and resumed his relentless thrusting. It took me a moment, more dread than actual pain, to find the best angle, and even then I had to go through the 'pooshing' process again. After that, though, surprise of surprises, it wasn't bad.

One camera was above me and aimed downward on my back, clearly showing how much of Cyrus's cock penetrated me. The other was down between his knees shooting upward, distinctly showing his balls flopping against my clit every stroke. The topside camera pulled back and around to my side where it traveled up and showed my tits flopping wildly each time he thrust inward. It continued upward to show my face, rapt in concentration, eyes almost completely shut, mouth half open. A tiny amount of drool leaked out of the corner of my mouth down my chin.

Every ten or twelve strokes he pulled completely out and showed the camera my asshole, stretched so far out of shape it gaped wide open even without his dick filling it. Then he'd slide back in, out again to show more gaping, and repeat, sometimes two or three more times. Then back to solid buttfucking.

Somewhere in there I noticed something odd -- my ass didn't hurt, at all. Quite the opposite, in fact. I can't believe I'm saying this, but it actually felt good.

Cyrus pulled out of me again, but this time not to show the cameras my gaping ass. He pulled on my hips again, tugging me to a standing position. He sat on the couch, and turned me so my back was to him. His feet were together on the floor, and he set me where I straddled his knees. He pulled downward on my hips, lowering my ass toward his cock. When I was low enough, he guided his tip back into my gaping rectum, pulled me lower, then pushed me upward again, to where he almost came out of me. He pulled me down again, and pushed up. He repeated the motion, controlling me with his grip, but my thighs provided the muscle, pushing me up then relaxing to let gravity lower me down over him.

He set a brisk tempo, and I got a pretty good rhythm going, but the angle my legs were at made the raising up part murder on my thighs. It didn't take long before they cramped up and I froze. He seemed to expect that. Using his hands on my waist again, he lifted me to the upper limit of my stroke, and held me still. He thrust into me, lifting his butt upward, and pulled out. He went in again, out again, finding his upper and lower limits, and then he went to town. The good news was, all I had to do was hold still. It still strained my thigh muscles, but nothing like the brutal over-exertion from before. The bad news was, now he got to set the pace. He held nothing back. He went fast, and he went deep.

This was clearly his run to the finish, building up to cumming. The strangest thing happened, though, even odder than noticing it still didn't hurt much. With my legs spread so far, each thrust into my butt tugged on my pussy lips, stretching them, rubbing them against my clit. I could feel that I was well on my way to cumming with him, without even putting my hand down there and rubbing. I steadied myself with my hands pressed on my knees, holding myself still, leaving all the motion to him.

Both cameras were shooting us from my front, one of them from a low perspective, in a close-up showing my ass being poled by his dick, with my pussy clearly flexing in the same rhythm. The other was more from a standing point of view, with a wide shot from my knees to my head. It began a slow zoom into my boobs, showing them flopping up and down in sync with his dick penetrating me.

He slid his hands upward from my waist to my tits. He cupped them, found my nipples between his fingertips, and began tweaking them, one at a time, back and forth, in rhythm with his plunging into my ass. It was an irresistible combination, and I came, and came, and came. He told me later that he hadn't been anywhere near cumming yet, but when my pussy pulsed my ass pulsed with it, squeezing him so tight it pushed him over the edge.

One of the cameras tilted upwards, capturing my face, eyes three-quarters-shut in little slits, mouth ajar, right as I began to cum. My face warped, then relaxed into an ecstatic half-grin. I wasn't even thinking about the cameras, I was just astonished to find myself cumming from being butt-fucked with such a freaky-big tree trunk. In the final edit, Ryan held on my face for a long time, watching my smile soften into a relaxed, confident grin. Then he cut to Cyrus's dick softening and sliding out of my ass, and his cum dripping out. On that shot of my face, my astonishment shows. It looks completely genuine, because it wasn't acting. I was amazed.

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Josh and Tanner packed the video and audio gear, and the lights from the porch and interior shots. They loaded them into a van and left together. Tom gave me a hug and disappeared into the back of the house. Ryan told me later Tom stays in the spare bedroom when he flies in for shoots at the beach.

Ryan showed me to the master bathroom. I took a quick shower, and put my bikini back on. Ryan walked me back to my hotel. We walked in silence; I was deep in a whirlwind of thoughts, all along the line of 'what the fuck just happened?' He seemed to realize that and didn't interrupt.

He finally said, "You enjoyed that, didn't you?"

I wasn't sure how to answer. I mean, I did eventually cum, and I definitely enjoyed that, but there were some extremely difficult moments on the road to getting there. "Enjoyed what?"

"Well, for starters, when he rimmed you."

I shivered, savoring the exquisite memory. "Yeah, I did. You're saying it showed?"

"Yeah, it showed. I'm glad you didn't hate it. Many girls, many people, hate rimming."

"I imagine most people hate giving it."

"Yes, but a lot of people hate receiving it, too."

"Really? I get not wanting to give, I have to overcome a lot of internal resistance to give, but hate receiving? What kind of moron wouldn't want to receive something that feels so amazing?"

"Apparently, it doesn't feel that amazing to everyone, or maybe they're so deeply repressed they can't let go and enjoy it."

We walked in silence for a while. I guess he wanted to see what I would say next.

"I feel sorry for them," is all I could come up with. He nodded.

I asked him, "You said I'll have a shoot every other day?" He nodded. "So, I have this afternoon and tomorrow off? You'll be shooting tomorrow?"

"Yes. I also have another shoot this afternoon -- two shoots a day for me and the crew. Your shoot went so well, no retakes, the guys and I actually have time for a leisurely lunch. Thank you for that, it's rare. Tonight, you can have dinner on your own, or I'll call you when we're done and you can join us, but it will probably be late."

"Okay, thanks. What will my shoot be day after tomorrow?"

He grinned. "You know it's better if you don't know. It'll be easy compared to today."

I nodded.

"You did great today."

"Thanks. So nothing new next time?"

"I didn't say that. I can tell you it won't be anything as physically daunting as Tom, but I think it will be challenging in other ways. At least I hope it will be challenging. You handle the unexpected well, and so far it's made for some primo video. I can already tell today is going to be another great one."

I nodded. I asked, "After today, what could be a challenge, or unexpected?"

He just grinned. I began to sense that tingle of excitement I felt leading up to both of my shoots so far, heavy expectation overlaid with a touch of dread, all wrapped up in an intoxicating bundle of fear of the unknown and anticipating some extraordinary possibilities.

Suddenly, day after tomorrow seemed a long way off...

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