(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.
“On yer knees.” He waited until I had settled. “You know how ta untie a knot?”
“Yes.”
“Do it.”
While I worked to untie his rope belt, he unbuttoned his shirt. When I got the knot untied, he said, “I think you know what ta do now.” I pulled his pants down. He stepped out of them and pulled off his shirt. He wasn’t wearing underwear.
“Holy shit!” I blurted. I couldn’t help myself… I’ve never seen such a big cock. Jeez lapeez! Now I remembered I was making a video, and that I had pretty much already agreed to take this thing into my mouth, my pussy, and -gulp- my ass. I didn’t think it was going to fit into any of those. Seriously, no way! Not even for thousands of dollars.
All that was when it was only beginning to get hard. He said, “Open,” and put the tip, already turning an angry purple color as it began to swell, on my bottom lip. He placed his hand under my chin, and pulled it up until my mouth encircled his entire girth.
“Bup weeb oup ip be opeb,” I tried to say around a mouthful of man meat.
“What?” he said. He pulled his dick out.
“But we’re out in the open.” I gestured toward the hotels. “Anyone can see us.”
“Ah’m out here nekkid all tha time. Like you said a minit ago, no one can tell if we have anything on or not.” He pronounced can ‘cain,’ anything ‘inny-thin,’ and on ‘ohn.’
“But it’s going to be pretty obvious you’re getting your dick sucked. You don’t think that will offend anyone?”
“Hmmm, yew might be raht.” He pointed his gun at his house. “Okay, up there.” He grinned a lopsided grin. “If yew run, I’ll trah for a flesh wound in the laig.” He grinned bigger. “But ah cain’t promise mah aim is that good.”
His house was mostly hidden under a canopy of lush tropical plants — their shade probably reduced the sweltering summer heat. There was a visible gap near the front corner, surrounding what seemed to be a screen door. He broke character and said in a deep, rich speaking voice, “We’ll have to wait a minute or two for Ryan, Tanner, and Josh to set up the next shot. It shouldn’t take too long.” I nodded.
He stuck out his hand, and we shook. “I’m Tom, nice to meet you Amber.” I nodded, the most I could manage in my surprise. “You’re doing fantastic. Ryan said you were a natural. I can already tell this video is going to be a great one.”
We heard the guys say “Roll,” “Speed,” and “Speed” from behind the veil of vegetation. One of them did a single clap, and Ryan added, “Ready.”
Cyrus and I stepped up to the gap in the vegetation, he pulled open the screen door, and we entered a surprisingly large screened-in porch. He sat on a rustic bench seat with bright, floral weatherproof cushions, placed an arm in each direction across the back, and slid his butt forward until it was only half on the seat. He spread his knees, placed his feet further apart than his shoulders, and gestured at the ground between them for me to kneel there.
His balls were what you’d expect in summer heat — loose and hanging low. His cock, now completely soft after a few minutes with no excitement, draped over them and hung an inch or two lower. It was easily six or seven inches long, and almost two inches across. And that was flaccid.
He saw me staring at it and said, back in his raspy ‘Cyrus’ voice, “Yew ain’t never see’d a pecker this big, have ye?”
I shook my head. He pointed at it and said, “Tahm to git busy.”
I took it into my mouth. Before it hardened much, I could get almost half of it in, but that didn’t last long. I began stroking, and it grew, and grew, and grew. Its girth stretched my jaw uncomfortably, and even with both hands gripping it, it got so long I couldn’t go deep enough for my lips to reach my hand.
I bobbed my head over it for what seemed like an hour, but he didn’t seem close to cumming. He may have sensed how tired my mouth was getting, or he may have just wanted more of his dick stimulated, but he said, “Yeh can lick farther down ohn it if ya want to.”
I gripped the tip and squeezed it, and licked from where it joined his balls to where it was wet from my sucking. Holy moly this was a lot of dick!
“Use yer lips, too,” he directed. I slid an open-mouth kiss up and down the saliva I already left. On my third or fourth trip up and down he moaned, the first sign other than getting hard he liked what I was doing.
“Suck mah balls while yer down there,” he said. They were smooth, he must shave them. I sucked on one, then the other, then the first one again, then he was ready for more dick sucking and pulled me up by the hair. I remembered the cameras and on the trip up licked the underside one long stroke from the base to the tip. It felt like it was about three feet long; I was still astounded at the size of it. I hoped he knew that there was no way it was going to fit in either of my other holes.
I sucked the head and what few inches of shaft I could get into my mouth, and stroked the rest of it with both fists, in time with my mouth. I got a pretty good rhythm going, not exactly fast, but quite quick for this much size. Every couple of minutes my mouth would tire and I would take a short break from sucking, stroking the tip with one fist, two or three times faster than I stroked with my mouth, and taking care of the rest of the shaft with the other fist.
It was during one of these rests that he said, “Back to mah balls.” Okay, down I went. I licked one ball, sucked it, then the other. I was on my way back to the first one when he pushed on the top of my head and said, “Lower.” Oh, okay, here we go — it’s going to be a $4,000 shoot.
He spread his legs further and lifted his nut sack out of the way. I started licking his taint and was quite relieved to find none of the gamey, sour taste I feared. The prevailing aroma was a pleasant, citrusy body wash, mixed with a bit of fresh sweat. I sensed both Ryan and Josh bringing their cameras in for a close look.
Cyrus lifted his knees up to his ribs, then pushed me straight down onto his brown star. This was only the second time I ever did this, but like the first, his grooming was fastidious enough that his asshole was nothing more than some skin with a different texture.
I began by sticking out my tongue as far as it would go and flicking it lightly across his anus, giving the cameras a clear view that my tongue actually touched his asshole. I licked up and down, I licked side to side, I licked in a circle.
One of the cameras came up close and personal, barely a few inches away from my tongue caressing his asshole. I found out when I watched the finished video that the other camera went around behind me to look up between my legs, across my empty pussy and my tummy, past my tits dangling and swaying in the open air, to my chin, firmly in place between his butt cheeks.
I stiffened my tongue and mini-fucked his asshole. He liked that, moaning softly. He laced his fingers in my hair, on top of my head so his arm wouldn’t interfere with the main camera shot. I alternated the mini-fucking with open-mouth kissing and licking his ass and around it.
I stayed on his ass, going back and forth between tongue and lips, for quite a long time, at least it seemed long to me. I don’t think he would have ever tired of that, but it gave him no means to cum, and he seemed ready to get off. He pulled on my hair to bring me back up to his dick.
I took his monster back in both hands, like the world’s largest video game joystick, and licked around the huge tip before taking it back in my mouth.
He was ready to cum, and he wasted no time making that clear. He pushed and pulled on my head, establishing a rhythm that was much faster than before. The good news was, at that pace I couldn’t go nearly as deep, which was fine with me. Just the tip and an inch or two of his shaft filled my mouth more than full. When I reached a tempo he liked, he removed his hands, leaving me stroking him on my own.
Even though he was ready, it still took him a while, and my mouth got seriously tired again. I didn’t take a fist break, though. I wanted him to cum as soon as possible, before it occurred to him to try to go deeper and get more of his pole into my mouth. I sucked extra hard, and just when I was going to have to give in and take a break, I felt his cock quiver at its base, then down its length, and he exploded into my mouth. I remembered the cameras, held his tip on my lower lip, and opened my mouth as far as it would go, letting the cameras see him squirt against the back of my throat.
I was grateful that he only came a regular amount, not in proportion to his size. When he was through, I showed the pool of gooch puddled on my tongue to one camera, then I turned to the other and showed it. I made an exaggerated show of closing my mouth and swallowing, and showed each camera my empty mouth.
I took his tip back into my mouth, sucked it in and out, and made a show of slurping up any stray cum. I finished sucking and smacked my lips. Ryan said, “Cut” to Josh and Tanner, and “Hold your position for a moment” to Tom and me. I stayed on my knees as he put his camera down and got his cell phone out of his pocket. He used the camera function to take a few stills of Tom and me showing where he sat, where I knelt, and other cues to our exact position.
“Fifteen-minute break,” Ryan said. Tom helped me to my feet, and Ryan led me into the house. The air-conditioned house, I was happy to notice.
The inside wasn’t the hovel I expected. It had hardwood floors that were well cared for, and was furnished with simple but elegant pieces of teak Danish modern. A few tasteful photos of landscapes graced the walls. I found out later it was actually Ryan’s house.
Tom set me down on the sofa, and Josh handed me a bottle of cold, cold water. I don’t think I ever tasted anything so good.
Fifteen minutes went by in a flash. It was long enough for me to get seriously worried about what was going to happen next. I had no doubt that next on the agenda was Tom fucking me, and I had no idea how my poor pussy was going to stretch enough to take his cock without tearing. I couldn’t even begin to think about what would come after that, him trying to force it into my ass.
We went back out onto the porch, and even though it was barely 10:00 a.m., after the air-conditioned house, the heat and humidity were stifling. Cyrus sat back on the bench, and I knelt between his knees again. Ryan and Josh spent a minute looking at the photos on Ryan’s phone, micro-arranging us so we were a perfect match to our earlier positions.
When they were done, they picked up their cameras, Tanner hoisted his mic, they each pushed a few buttons, recited the “Roll” and “Speed” litany, and this time Tom did the gator clap.
Cyrus took my hand and pulled me to a standing position. He cupped his hand under my pussy and rather roughly stroked my slit. “Now let’s see how much of mah pecker your sweet coochie ken take.”
I brushed his hand away and said, “I don’t think so. You’ve had your fun, I am out of here.”
He looked surprised, then held up his cell phone. “Oh, look, that ‘er ‘9’ and ‘1’ are still there, all ah haff t’do is press anuther ‘1’ an’ it’s 30 days fer you.”
He stared at me, locking his eyes onto mine, grinning like a coyote leering at a stray chihuahua. Ryan had a shot of Cyrus over my shoulder, and Josh had a shot of me over Cyrus’s shoulder, two naked warriors locked in a wordless battle. I stared back at him for a long moment, then rolled my eyes and said, “Whatever…” He grinned, opened the door into the house, and gestured me inside.
He set me down on the sofa, pushed me back into a reclining position, and lifted my ankles up toward the ceiling. I shut my eyes. It was going to take some concentrated effort to relax enough to let his tree trunk into my pussy, and although it doesn’t make sense now, somehow at the time it seemed like shutting off all light might make that task easier. I braced myself, trying not to let the dread I felt show.
He surprised me, though. What he pressed against my cleft wasn’t the tip of his cock, lining up to split me in two like Vlad the Impaler. It was his face, his tongue and lips. What? He wasted no time getting busy.
Oh my, he quickly showed he was a master down there, he really understood female anatomy. He knew exactly which bits liked active, aggressive tongue, and which ones preferred soft, mellow lips. I couldn’t fully melt into relaxed enjoyment of his skills; in the back of my mind I knew that he was softening me up to receive his dick there, but damn! he was talented. I mean, damn!
As smart as he was about what to do, he was a master of when to do it. Rather than racing to get me to cum as soon as possible, like the typical inexperienced college guy I was used to, he took his time, letting me thoroughly enjoy the moment. He licked the length of my slit. He sucked the soft tissue around my clit. He circled the hard little nub and flicked his tongue over it. Because I knew that soon he would be forcing his monster into me, I was as tense as I had ever been while having a mouth on my muff, but even with that, I could see that if he kept this up, it wouldn’t be long until I would be cumming my head off.
As he tongued my slit, licking up and down, he pointed his tongue and slipped it between my inner lips, a little deeper each time he traced from bottom to top. He lengthened his strokes, not only going over my clit on the top but also going a little lower at the bottom and licking my taint. It felt amazing. That little patch of skin is so sensitive, and it is so rarely given any attention. His tongue was so soft and luxuriant, my skin crawled with delight. I was definitely less tense than I was a minute ago.
A couple of strokes later, he went even lower, and licked over my asshole. It was just a slip, an accident, but I loved it, even if it was just once. I had intentionally done that very thing to two different guys, including him just a few minutes ago, but no one had ever done it to me, even accidentally. For that brief moment I got to experience why Ryan was willing to pay me a lot of extra money to do it; it was amazing how great it felt.
He returned to my pussy, I assumed to stay there and recover from his tongue slip, but on his next stroke he went all the way down again, and the stroke after that too. One more pass across my pussy, and then he went down to my asshole and stayed there. I moaned, long and loud, and lifted my knees higher, to give him greater access.
“Lahk that, do ye?” he said. I nodded, too consumed with the moment to realize he’d never be able to see it from where he was between my butt cheeks. Josh caught it on camera, and Ryan included that short shot in the final edit. Most people who watch the video will only see how deeply I’m enjoying myself, but when we watched the final video Tom had Ryan pause and replay it. He pointed out that he had no chance of seeing me nod, and all of us — Ryan, Josh, Tom, Tanner, a few others, and I — shared a good laugh.
Cyrus dived back in, rippling the soft width of his tongue across my ass, lighting up thousands of sensitive, never-before-stimulated nerves back there. He pointed his tongue, circled my asshole and drew dozens of letter x’s across it. I thought that was it, nothing was going to feel better than that, then he stiffened his tongue and began mini-fucking me with it. Unbelievable — it was better.
He introduced a finger, pushing it barely one knuckle deep. Several guys had tried their fingers in my ass before, but somehow Cyrus’s felt completely different. Maybe it was the saliva smoothing the finger’s entry, natural lubrication overcoming any harsh, raspy friction. Maybe it was all those thousands of nerves being newly awakened by his tongue, feeling pleasure for the first time. I think it was both. Whatever the difference was, he worked the finger in deeper, down to the second knuckle. He began pulsing it in and out, creating a whole new set of heavenly sensations. He eventually worked his finger all the way in, sliding it slower as it went deeper. All I can say is, I never knew that anything from that particular part of my body could feel so good.
The rational part of my brain tried to tell my ass there was a world of hurt coming, but it ignored that message and savored how good it felt right then. Cyrus was arousing nerves that rarely got any attention, never any good attention. They were thrilled at being noticed now, and they obviously were going to ignore any warning that might mean there was a downside to their current pleasure.
He returned his mouth to my pussy and resumed delighting it with his tongue. He not only left his finger in my butt, he sucked the next finger over into his mouth, coated it with a thick layer of spit, and slid both fingers in. They entered smoothly, sliding in and out easily on the natural lube he had given them. They stretched me out more, and to my great surprise didn’t hurt. I couldn’t believe how wonderful the combination of my pussy being licked and my ass being finger-fucked felt. Who knew it could feel so good? Well, apparently, Cyrus did.
He pulled his fingers out and lifted his mouth away. My clit reached out to re-connect, but his lips and tongue were too far away. I was sure this was when he was going to force his fence post into me, and I tried not to noticeably tense up. I was happy to be wrong. He returned his tongue to my ass, lavishing it with a gentle, exhilarating tongue massage.
All too soon, he returned his mouth to my pussy, and re-inserted two fingers into my ass. They felt different, slicker. It wasn’t until I saw the final video that I found out why — they weren’t just wet with saliva, they had lube on them, lots of it. He pressed them in further and further, until they were in as deep as they would go, and slowly slid them out. He pressed them in again, still slowly, just not quite as slow. Next time in was a bit faster. The wonderful things he was doing to my slit and clit distracted me somewhat from what he was doing in my ass, but before long he was finger-fucking me there at a steady pace. Every few strokes he turned his wrist to a different angle, stretching me in all directions, coating more of my insides with lube.
He pulled his fingers out, and licked downward from my slit back to my ass. It had only been a minute or so, and I thought I remembered how amazing, how electrifying, how thrilling it felt to be tongued there, but I was wrong. It was more tantalizing, more captivating, more enticing than I ever could have imagined. I hoped he would never stop.
Eventually, of course, he did stop. He coldly, cruelly licked upward, across my taint again, and back to my slit. My clit welcomed his tongue back; everywhere else wanted him back down lower.
He pushed fingers back into my butt. The intrusion was larger, so it must have been three fingers this time, and they slid in and out easily, so they must have been heavily coated in lube. He worked them in and out, in and out, in and out again. He set a steady pace, pushing them all the way to his palm, and all the way out to the very tips. He completely stopped after a short minute or so. He was receiving so little resistance in my ass he must have deemed me relaxed enough to proceed with fucking my pussy.
He lifted himself up, and my mind came to a halt. This was it, the moment I dreaded: he was going to press his monster dick into my pussy. Then a lightning bolt of realization hit me — shit, I didn’t have to worry about my pussy. He wasn’t going to stretch it, tear it, break it, ruin it, or make it even slightly uncomfortable. That was a huge relief, but one with a giant ‘gotcha’ attached, which chilled me to my core. The reason he wouldn’t hurt my pussy was he wasn’t going to fuck me there; he was headed straight into my ass. Ack! I tried not to panic. I failed.
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.
: : : : :
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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