Some More Money Ch. 01 - Trespassing

(Author's notes: This is a work of fiction. In this fantasy, nobody is worried about STDs. In real life, all non-monogamous sex should be practiced using accepted safe-sex precautions.

This story revisits the characters of an earlier story, Some Extra Money. This story stands alone, you don't need to have read that story to understand and enjoy this one. However, if you want to read them in order, Some Extra Money comes first, then this one.

Two warnings: First, a little one. There is some plot and character development that happens before and during the sex. The bigger one: like the earlier story, the assplay in this one goes beyond a penis penetrating a female anus. This is the anal category, but if you prefer your anal action limited to buttfucking, you should probably skip this one.

Very special thanks to editors Ravenna933 and Sidney43. This is a better story due to their efforts and insight. Any remaining faults are solely the responsibility of the author.

All characters involved in sexual activity are at least 18 years old.)

: : : : :

I was having such a nice, warm, relaxing sleep. I needed it. That morning I had taken the last final exam of my Junior year of college. After five exams in four days, I was spent. I didn't intend to fall asleep, but I settled into a soft chair in my apartment and was out like a light within seconds. Aah, sweet rest, sweet warmth, sweet comfort. I curled up like a kitten in the afternoon sun.

Until, that is, my reverie was shattered by my phone's shrill ringtone. That would be my best friend Kristen calling. She also took her last exam that morning, and we were going to celebrate that evening. I'm sure she was calling to finalize our plans. Going out this evening seemed like a great idea when we discussed it earlier in the week, but now that the time was here, I didn't have the energy. I was sure I had done well on every exam, and that was worth celebrating, just please let's do it tomorrow night. I let the call roll to voice mail.

Instead of the expected chime telling me I had a message, the phone rang again. Dammit, what was I thinking when I chose that ringtone? It was way too harsh and irritating.

I clicked the phone on and barked "What?" into it. Oops, it wasn't Kristen.

"Hi Amber, I mean 'Louise,'" a baritone voice chimed. It was Ryan.

I wasn't sure I wanted to hear from Ryan. He is a video producer, an X-rated video producer to be precise. I, um, I 'starred' in one of his videos not long ago. I didn't do such a thing casually. I struggled deeply with many questions beforehand. Was I having sex for money? There's no escaping it, I was. Does that make me a whore? I don't think so. I had sex with one guy in my first video, and I assumed if I did any more, there might be a few guys per shoot. Ryan screens us all for STDs. Prostitutes, on the other hand, have sex with multiple guys every week, with little or no screening.

Was I being objectified? Yes, definitely. That's kind of the point of porn, isn't it? Was I demeaning myself? I don't think so. I was coming from a position of strength, not helplessness or desperation. I was in control of what I did, and I could say 'no' at any time.

Lastly, was I being taken advantage of? Again, I don't think so. Ryan made me feel safe, and just as important, he paid me an absurd amount of money. Add it all up, I saw nothing to be ashamed of.

'Louise' was my screen name. For obvious reasons I didn't use my real name. I liked 'Crystal' or 'Angel' for my alias, but Ryan chose 'Louise' for me. He monetizes his videos by selling memberships to his web sites, and he says his subscribers prefer old-fashioned names like Louise, Agnes, Mildred, and Harriet.

Ryan's voice yanked me back to the present. "Amber? Are you there?"

"Oh, hi Ryan. Sorry I growled at you, I was expecting someone else. What's up?"

"Spring semester is done, right?"

"Yes."

"Are you busy next week?"

"Just working, why?"

"You're still waiting tables? Have you already spent the money I paid you a month ago?"

"Yes, waitressing, and no, I haven't spent very much of the money. It's not going to last forever, though."

"Are you taking any summer classes?"

"Two. One starts in ten days, and the other begins right after the first one ends."

"Will you have any time between the second class and fall semester?"

"Yeah, two weeks. Why all the questions?"

"Quit your lousy waitress job is why. I'll be shooting all summer, and I can use you on several shoots in the weeks you have off from class."

I liked that about Ryan, that he would flex his schedule to mine, not requiring me to adjust to him. I wasn't sure I wanted to be in any more videos, but I didn't think it would hurt anything to find out what he had in mind, so I put my reservations on hold for the moment. I asked, "How many is 'several'?"

"Maybe as many as five or six if you're up for it."

"Tell me about the videos."

"You know it's better if you don't know what to expect, so you don't have to do much 'acting.'"

"Do they pay the same as the first one?"

"Yes, my standard pay scale. $2,000 for fucking and sucking, including swallowing. $3,000 for anal, and $3,500 if you also rim a guy or two, or maybe three."

"Nice try, Ryan, but if you remember, I won't rim for $500, but I will for $1,000."

"Okay, okay. $4,000. That's $20,000 for the summer if you do five shoots, $24,000 if you do six. Are you gonna make that much in tips this summer? Or even for the rest of the year?"

"No, of course not, not even close. If I do quit my job, do you guarantee me six shoots?"

"I can guarantee four. The other two depend on how quickly the shoots go. Come by my office and we'll sign a contract for four if you like. That commits me to paying you $16,000 even if we never shoot anything."

"Okay. When's the first shoot?"

"In a couple of days. At the beach."

"How long of a drive is that? Six hours? I'm not sure my old car will drive that far."

"You won't need to drive, I'll fly you there. I'll get you a beach-front hotel room, and you can ride everywhere with me, or take a taxi or Lyft on your own dime."

"What do I need to bring?"

"Whatever you would pack for going to the beach for six days. The crew and I will be shooting every day, but you'll 'perform' every other day. I'll provide wardrobe for the videos."

"Wardrobe? You mean I'll have clothes on?"

He laughed. "Good point. You will, at least at the start of each video."

I didn't say anything. He said, "Are you there?"

"Yes. I'll be honest, I'm not sure."

"Is there anything I can tell you to make your decision easier?"

"No, I don't think so. I just need to sleep on it."

This time he didn't say anything. I said, "Are you in your office tomorrow morning?"

"Yes."

"I'll let you know yea or nay then. If I decide to do it, I'll come by to sign the contract and pick up my ticket."

"Okay, good. I'll also need you to swing by the clinic and get fresh blood work done."

"All right. Talk to you tomorrow."

That evening I was wracked with doubt. I all but decided I didn't want to do any more videos. I was glad I had done the one. It was an adventure, an impulsive walk on the wild side. I might regret it later, but not too deeply -- as it stood, it was something I tried once and never repeated.

Doing more, though, was far more serious. I wouldn't exactly be committing to a life of debauchery and sleaze, but wasn't it a giant step in that direction? I didn't want to be marked for life as a 'porn girl'...

After a couple of hours of sleepless thought, though, I rationalized that Ryan's website was a tiny, independent enterprise. He didn't manufacture dvds that would feature my face -- and other body parts -- for years on x-rated video store shelves and websites. And he didn't have so many subscribers that I would be running into 'fans' for the rest of my life.

One more thing, though, an important one. I, um, I don't exactly know how to explain it, but every time I think about Ryan's site, I get crazy excited. It has an icon on it with a thumbnail image of my naked body. All anyone -- that's anyone -- has to do is join Ryan's site for a small fee, and they get full visual access to my body. My tits, my ass, my pussy, all of them bare, sometimes in a full-body shot with my face, sometimes ultra-close-up, just sitting there ready for someone to look at them. Sometimes I feel an odd psychic link, and the video pops into my mind like someone is watching it right now. My body tingles and my mind wanders. I can feel his eyes on my private bits. I can feel him playing it in slow motion, watching me take off my clothes. I can feel him ogling my body, freeze-framing close-ups of my private bits to stare at them as long as he wants to.

Then, at his leisure, he watches me take Ryan's dick into my mouth and stares at me sucking him, stroking him. He imagines it's his dick shooting streams of cum into my mouth. He pictures his dick slipping between my pussy lips and plunging deep into me. He pretends it's him fucking me, fucking me hard. He imagines it's his dick pressing against my asshole, looking impossibly huge, like it will never fit in there. He pictures what it feels like to press inward anyway, to push in, to force his sensitive tip in, to keep pushing, to eventually bury his entire length in my ass.

Lastly, he imagines my tongue licking his asshole.

The thought of having more videos available for viewing, of having more guys watching me and imagining my mouth, my pussy, and my ass pleasuring their dick, and of having my tongue stimulating their butt, got me deeply turned on. Add in Ryan's imagination and the likelihood that he would stretch my erotic boundaries even further, there was no way I could be objective in making this decision.

: : : : :

My hyper-active libido won out, and two evenings later, I found myself hundreds of miles away from my apartment, at a beach-side restaurant having dinner with Ryan, two other guys, and three girls. They were all attractive in a wholesome way, and seemed nice. None of them had the sleazy appearance or phony-baloney personality you'd expect from 'porn people.'

Ryan introduced us. I asked, "Are these the other actors?"

"Josh and Tanner aren't. Josh is the second cameraman, and Tanner does sound and lights. Alexa, Janelle, and Lindsay might be in later videos with you, depending on what we shoot."

We greeted each other.

"I'll be shooting tomorrow?"

He nodded.

"Who's in that shoot?"

"He's not here. It's best if you don't meet him until you're on-camera with him."

That sounded ominous. Alexa, Janelle, and Lindsay glanced at each other knowingly. No one offered to share with me what the secret was, and being pretty sure that they wouldn't tell me, I didn't ask. I'd be finding out soon enough.

: : : : :

The following morning, barely 9:00 a.m., I was on the sand near water's edge, wearing a tiny red bikini. Ryan brought identical suits in red, aqua, black, and white, and had me try them all on in my hotel room before we went outside. I thought at the time he did that so he, Josh, and Tanner could watch me get naked between colors. That didn't bother me; changing clothes was nothing compared to what they were going to be watching me do in a short while. I could have somewhat frustrated them by changing my top then changing my bottoms, but I played along and took both top and bottoms off before I put the next one on. If they get that big of a kick out of seeing me naked, let them see me naked. They agreed with each other the red one looked best on me, and they were right, it did.

Our hotel was third from the end of a long row of high-rises on the beach. They were all variations of the same theme, around twenty stories high, with floor-to-ceiling windows and balconies facing the ocean, and smaller windows facing the other way. They all had pools and burger bars at their base, with beer, daiquiris, and margaritas available, although the alcohol was under-emphasized to maintain a family-oriented look and feel.

Past the last of the hotels, the beach stretched out for a couple hundred yards to a single, isolated beach house. I hadn't noticed it before we started walking toward it, and none of the tourists seemed to have, either -- the beach between the last hotel and the house was completely empty.

That one lonely house was tucked into some dense beach vegetation, with what looked like miles of empty sand stretching down the shore past it. The house looked decades older than the hotels. I bet it used to be part of a long row of similar homes, and all the others had been sold to hotel developers and torn down.

Ryan, Tanner, Josh and I headed down the beach toward the house. Walking on soft, loose sand, it felt like it took forever to get there. I was buzzing with nervous energy, wondering what Ryan had in store for me. Since Ryan had phoned me a few days ago, I had worn a butt plug most of the time. He had suggested doing that for my first shoot, over a month ago, to loosen up my back door. He didn't mention it this time, but I assumed my ass getting fucked was on the agenda. Since Ryan wouldn't tell me what this video was going to involve, it was in my best interest to be as ready as possible for whatever might happen.

We stopped on the beach in front of the house, midway between it and the surf. Ryan readied his video camera, Tanner donned headphones and held a long thin stick which they called a shotgun microphone, and Josh set up a second camera.

Ryan explained what he wanted me to do. "It's simple. When we start, walk slowly about twenty-five feet that way," and he pointed away from the hotels. "We'll be walking with you. You're going to say a couple of things out loud so the viewers know what you're thinking. Say them loud and clear so the microphone can pick up your voice. First say something like, 'Okay, here is good, nice and private.' Then spread your towel out, and say, 'There's no one around, I think I'll take off my top.'"

"What then?"

"Take off your top, then just go with what happens. The only things you have to pretend are that Josh, Tanner and I aren't here, you're just a 'regular' girl on the beach who would be offended if a guy approached you expecting sex, and that your name is Louise, not Amber."

"It'll be clear what to do?"

He stifled a grin. "It'll be clear."

Ryan and Tanner took five steps back, Josh five in the other direction. Ryan said, "Roll," and a few seconds later Tanner said, "Speed," then Josh also said, "Speed." Tanner said, "Hold one arm out in front of you, hold the other one straight up in the air. Good. Now clap them together, like a gator snapping you between his jaws."

I did. I found out later that "Speed" meant their recorders were recording, and the clap was so they could be sure that pictures from both cameras and the sound were perfectly synchronized. No one told me anything else, so I waited a few seconds and strolled forward as he instructed. After a minute, I stopped and said, "Okay, this looks like a good spot, nice and private."

My mind shifted gears and I became Louise, a girl out on the beach by herself, looking for a place far away from the crowds so she could lose the tan-lines on her boobs. I looked around, and it wasn't even that I didn't let my eyes pause on Ryan, Tanner, or Josh; 'Louise' simply wasn't aware they were there.

I looked back toward the hotels and said, "There's nobody around, and I'm so far away no one can see whether I'm fully dressed or not. The sun is out, and the breeze coming off the water feels great. I'm taking off my top." I reached behind my back and pulled the lower string until the knot released. I left the upper knot tied and lifted the top over my head.

I immediately heard a chilling sound. I'd never heard it before in real life, but I'd heard it countless times on TV and movies. It's a unique sound that you won't mistake for any other if you ever hear it -- a gun clicking into the cocked and ready position.

"Yes, you will," a deep, raspy male voice barked at me. "Right now."

I snapped my head around toward the sound and covered my nipples with my arm. "Who are you?"

"Name's Cyrus, but that don't matter," he said. "What matters is, I'm the owner of this here private property. You're trespassin'."

I looked him over. He was an older guy, with long, unkempt salt and pepper hair and a matching beard. He was wearing typical clothes for a movie castaway, or maybe one of the Beverly Hillbillies -- what were once khaki slacks, now with raggedy cuffs, and an equally tattered button-down shirt. His face, arms, and bare feet were deeply tanned and wrinkled with age and excessive sun. His 'belt' was even an old piece of rope tied in a knot. Despite his scruffy outward appearance, he looked in really good shape.

"I didn't know," I said. "I'm sorry. My mistake, I'll leave."

"No, you won't," he said. "One of two things is goin' t' happen now. You're either gonna hand me that 'er top, or I'm callin' the po-lice to arrest you fer trespassin'."

"They won't arrest me," I protested. "The boundary isn't marked. They'll let me go with a warning."

"That 'er girl last month said that same thang. She's servin' 30 days raht now 'cause she didn't have no $10,000 to pay tha fine."

"$10,000? That's-"

He lost his patience and barked, "What's it gone be? I'm dialin'... Nine..."

"Okay!" I shouted at him. He grinned.

By this time, I was so deep into this scene that Ryan, Tanner, and Josh didn't exist. I was locked in a battle of wits and wills with the gruff old guy, and I had just lost round one. I handed him the top. He wadded it up and put it in his pocket.

He stared at the arm I was covering my nipples with. "Hands by yer side," he said.

I glared at him. "No."

He held up the phone, "...One..."

"Okay!" I said, lowering my arms. He stared at my boobs.

"Turn a slow circle fer me," he said.

I felt a thousand beams of light prickling my bare skin, concentrated on the swells of my breasts. My nipples were diamond-hard in the morning beach breeze.

He pointed at my bottoms. "Those too."

I inhaled, but before I could even say "No way," he held up his phone. "One button away, and it's 30 days fer you."

I had completely lost sight of this scenario being make-believe. I bored laser-focused beams of hatred into him, hooked my thumbs in the sides of my bottoms, and began to tug them down. When I had them mid-thigh, he said, "Stop. Straighten up." He really knew how to make a girl feel exposed and vulnerable. With my bottoms part-way down, I felt utterly defenseless, more bare and unprotected than if I was completely naked.

"Turn another circle fer me." This time it was ten thousand beams of light prickling my ass and my muff.

When I faced him again, he said, "Go ahead and step outta those, and hand 'em to me." He put them in his pocket with my top.

Now I was standing there, naked, ocean surf behind me, his house in front of me, a dozen hotels in a row in the distance to my right, empty sand to my left all the way to the horizon. A strange old man stood there ogling me, a pistol in his hand, although it was no longer pointed at me.

"Turn around," he said. "Bend over." I did. "Put yer hands on them butt cheeks." I guessed what was coming next. "Pull 'em apart." I knew it. "Farther."

I thought this was when he would begin touching me, having his way with me, but I was wrong.

"Straighten up, face me. Step toward me," he said. "Closer." That put me toe to toe with him. I could smell his breath, a mixture of pipe tobacco and, surprisingly, citrus -- I didn't expect anything that resembled fresh.