"What??"
"Charles is really into the butt. He likes to alternate between my holes while I'm tied up, and I never know where he's going to finally drop his load. I'm telling you, if he thinks you do something similar, we're in. You'll have him instantly on your side and we can move forward with the rest of the plan probably as early as next week."
Dave wasn't saying anything, his mouth was just hanging open and he was staring at me. In his hand he held the keys to my cage which he was still holding after letting himself in from downstairs. I stuck my other arm out and gently pulled them out of his hand. He still made no move. I think he was in shock.
I slid the key into the lock and opened up the cage door and then crawled out. I ended up on the balls of my feet in front of Dave. The big trucker was just looking down at me. I was pretty sure he agreed with what I was saying, but just didn't know how to react. We'd had sex months before in the back of his truck, so I knew he found me attractive. I think his issue was that now that we had become sort of friends and given my current circumstance, he probably thought he was taking advantage of me or something. As big and strong as he was, Dave was a sweet pussycat, and he would probably never take advantage of a girl in distress. It made him a lot more endearing, actually. So different than pretty much every guy I deal with on a daily basis.
Of course, he might also know about Dani and I and think of this as a betrayal towards her, but I know she'd understand. She knows I'm still fucking guys daily while this plan takes shape, she'd be fine with Dave and I doing it for the cause.
With Dave's eyes still wide and looking down at me, I slowly reached up along his pant leg until I reached the button. He didn't stop me, but I could feel him tense up. I gave him a reassuring smile, tilting my head down a bit in order to make it seem playful. I wanted to lighten his mood, move his mind off of his worries and into the gutter a bit. I rubbed my hand along the front of his pants and then flipped open the button with a single practiced twist.
I decided to take the fact that he hadn't moved to stop me as a sign that he was okay with this, so I continued. Under his pants I could feel that he was already semi hard, likely because I was, as always, completely naked. I slowly pulled the zipper of his jeans down and then used both hands to tug on the fabric, bringing it down past his hips and to his knees.
The bulge in his underwear began to grow slightly, but still not as much as I would expect which meant he was still nervous about this encounter, unsure about it. I traced my fingers lightly along the outline of his cock and felt him shiver and then clear his throat.
"Anna," he began, his normal booming voice taking on a quieter tone.
"Shhh," I said, cutting him off. "Trust me, Dave, this is the best way. Why not just enjoy it? I plan to..." As I said that I slipped my hand underneath his briefs and grabbed his warm shaft. As soon as my fingers closed around his spongy soft flesh I felt it harden against my palm. I stroked him up and down a few times under his clothes but it was too restrictive, so I finally reached up and pulled them down to where his pants were bunched at his knees.
Dave's cock stood firmly in front of me. It wasn't huge, but definitely a good size and one that I could get a lot of pleasure out of. His big balls hung below and I used my free hand to massage those gently, letting them roll back and forth as I resumed my slow strokes along his shaft. He had closed his eyes now and was clearly starting to enjoy my manipulations.
Moving up to my knees, I got to eye level with his cock. I held it up against his belly and turned my head, sticking out my tongue and giving his sac a big long lick. I heard him gasp in surprise from above, but he still made no move to stop me.
I let my tongue roll along his wrinkled balls, bathing them in my warm saliva and noting with satisfaction that his cock continued to grow and harden in my hand until I was pretty sure it couldn't get any bigger. At that point, I licked along the length of him until I reached the head of his cock and then opened my mouth, taking it in.
Dave was grunting softly now, and his hands had finally moved to the top of my head, gently guiding my mouth along his dick. I rolled my tongue around him a few times but I had no intention of letting him waste his load in my mouth. After a couple of minutes I pulled gently off of him. I reached down and pulled his pants and underwear off completely and then stood up to help him remove his shirt. Dave was now an active participant, so it made things a lot easier. I once again admired the muscles that ran along his chest and arms. He was once in very good shape, and only his growing belly betrayed the fact that he had recently let himself go a little bit.
Once he was naked, I pushed the big man down onto the floor of the room and lay him on his back. Unlike most of the guys that fucked me in here, I was in control this time and I wanted to make sure that I got a little satisfaction. I straddled his body until I was standing over his head, his big eyes were staring right up at my moist slit. Without a word I dropped down and sat on his face, trusting he wouldn't object. His tongue reached out immediately to meet my pussy and his hands came up to wrap around my thighs. I tilted my head back in pleasure, closing my eyes to concentrate on the feeling below me.
Dave wasn't the most skillful with his mouth but he was good enough. It didn't take me a lot to cum, and after a few minutes I was feeling like I was ready to go. I pushed down from his face and slid along his body until I felt the head of his cock push against my lower lips. I smiled once at Dave and gave him a little kiss as I shoved backward, impaling myself on him. We both let out a groan into each other's mouth as our bodies connected.
Dave wrapped his huge arms around me and pulled me tightly down onto his hardness, pushing in as deep as he could and I helped it along as much as possible, trying to pull him into me just as urgently. Since I was on top, I controlled the pace, sliding up and down his body slowly, not wanting him to cum as quickly as he did last time. He still had one more hole of mine he had to pierce. I continued to ride him, running my tits along his hairy chest each time I slid along his body since he wasn't able to touch them with his hands. Each time I felt his hips start to thrust forward against me faster I would slow down in an effort to prolong him, but I knew it wasn't going to last much longer.
"Let go for a sec," I said. Dave relaxed his grip around my back and I slid off and onto my knees, presenting my ass to him. "Time for a switch."
I looked back over my shoulder as Dave pulled himself up behind me. He moved into position at my ass and his hard cock pressed against my pussy. I was so wet that as soon as his dick made contact it just slid in and he pushed forward immediately, sinking in as deep as he could go. I let him thrust a couple of times and then when he pulled back I moved forward slightly so that he popped out. I reached behind me with one hand and grabbed one of my ass cheeks, spreading it open in front of him and wiggling it. He knew what I wanted him to do.
Dave hesitated for a moment. I didn't look back at him because I was afraid he would try to argue with me again, so I wasn't sure exactly what he was doing, but finally I felt his cock head touch my puckered asshole.
Before he could change his mind, I pressed back firmly and felt his head break the seal of my ass, stretching it out. At this point, I've had so much anal sex that it didn't take much to get him past my ring and his dick was lubed enough from my pussy that he went in without any pain. He wasn't big enough that I needed any extra lube. Within a few strokes, I felt his hips touch mine and I knew he was in as deep as he could go.
I leaned forward, putting one arm down in front of me and resting my head on it as I snuck my other hand underneath my body to touch my engorged clit. As soon as I did I felt a jolt of electricity shoot through me, inflaming my extremities with tingly pleasure. I was so close that I was likely going to cum before him.
"Cum in my ass," I said. Charles would enjoy seeing that.
Dave was getting into the idea now, because as soon as I said that I felt him speed up. He wasn't going to take much longer himself, but I was already beating him. My fingers flew
quickly along my nub and I let out a loud moan as I felt my pussy contract as an orgasm started to overtake me. The contraction must have also affected my ass, because I felt Dave stiffen up as I began to cum and he let out a groan as well.
With one last powerful push forward, his groan turned into a roar and his cock exploded in my already convulsing ass. I squeezed my ass muscles around his dick, trying to milk out as much cum from him as I could while my own orgasm continued to rip through me. Dave leaned forward against me and his hands slipped around my body, finally grabbing hold of my small breasts and kneading the flesh as his dick continued to spasm.
The warmth from his cum and my climax filled me, spreading out all the way to my fingers and toes. We both continued to breath heavily for a few minutes as his hands idly rolled my nipple around under his palm. When his cock finally started to deflate, he rolled off of me and I collapsed down myself, turning onto my back.
"You're still going to have to tie me up," I said when I could finally breath well enough to talk.
Dave just grunted, either too tired after having cum or just plain tired of arguing with me.
We lay there for a little while longer and then he finally got up and dressed again. We spoke for a little while about our plan for next week, and then I directed him into tying me up similar to last week. When he left, I reminded him to tell Charles I was still bound.
As I expected, Charles came up quickly after Dave had left and was positively giddy at finding me in his favorite position with cum leaking out of my ass. He couldn't undo his own pants fast enough and soon I had another load leaking out of my pussy.
"I knew this guy was becoming a regular," he said as he was cutting me loose. "He's a man after my own heart."
"He's an asshole," I said.
Charles just smiled cruelly at me. "You just make sure to do whatever it is he wants and keep him happy. He's going to make us both some good money."
I bit my tongue to keep from making a comment about whether I'd ever see any of that money. Now wasn't the time to goad him into punishing me. I just said nothing and he left. I slept well that night, knowing that our plan was in action and Charles had taken the bait. I couldn't wait for Dave's next visit. It was time to make our move.
Week 43
This week couldn't come fast enough for me, and it was painful to wait as the days ticked by and my door would open only to have some new slimeball looking to get his rocks off on or in some part of my body instead of seeing Dave or Dani again.
I was hoping for a light week but instead I ended up having to eat out the ass of some disgustingly obese friend of Charles, who then asked me to put on a strap on and fuck him with it. Actually, that last part I kind of enjoyed, especially because he didn't object as I slammed it into him as hard as I could. I think it actually made that fat bastard cum even faster, to be honest. And when I was done, he even thanked me and then left. At least I didn't have to let him fuck me, although Charles made me clean up the stain he left on the floor.
By the middle of the week, I heard the door open and I could hear two sets of feet. The first face I saw was Charles, which was disappointing, but then a moment later Dave's big form came around the corner. He was clad in his typical jeans and heavy shirt, covered by his normal long jacket. It seemed a bit bulkier this time. I had to struggle not to let my face betray how happy I was to see him. To see them both, actually.
"Get up," said Charles, giving the cage door a little kick. I had been lying down as I did most of the time, as there was very little for me to do in this cage. I sat up and looked at the two men, feigning surprise.
"What's going on?" I asked.
Charles was bending down and unlocking my door. "Our friend Dave here has asked if I wanted to join him today. He's looking for some double stuff action and I'm happy to oblige. Anything for a good customer, right?" He shot me a glare that I knew meant he was warning me not to object. He wanted to keep his new regular happy and paying, and I'm sure being invited to join in was just an added bonus in his eyes. I bet the asshole was charging Dave extra for this, too. Only thing better than fucking me for free, as he usually did, would be to fuck me and have Dave pay him extra to do it.
I sat up and immediately felt queasy, which sometimes happens to me when I move positions too quickly lately. The door was already open and I was taking deep breaths to keep from feeling too sick. I figured part of it was nerves as well, since I had a good idea about what was going to happen and I could almost taste my freedom.
At any rate, it took me longer than normal to crawl out of the cage and consequently Charles gave me a shove as I emerged in frustration, although I suspect he was also trying to look tough and impressive to Dave.
Unfortunately for Charles, Dave was not at all happy about his aggression towards me and he immediately grabbed Charles by the back of the neck with one big hand.
"What the fuck? Let go!" Charles protested, trying to turn his head to look at the trucker but unable to because of the firm grip.
"That's no way to treat a lady," said Dave, and he forcefully pulled Charles forward headfirst into the bars of the cage. There was a loud clang as his skull hit the metal and then he collapsed to the ground in a heap as Dave released his grip. I stood there in shock, looking at the motionless body of my boss for a few moments. I had expected this, or something similar anyway, but now that it happened, and so quickly, I was having trouble processing it.
"I brought you some clothes." I shook my head, Dave's deep voice breaking me from my trance. I looked over to him and he was pulling them from the pockets of his jacket.
"I couldn't fit that much in here but it's at least something to cover yourself with when you come down," he said.
My face broke into the biggest smile I'd had in a while. Clothes! It had been months since I got to wear something. I gratefully took the thin t-shirt, underwear, leggings and socks and started to pull them on. "They're perfect," I said. At this point, I would have been happy to put on a big paper bag.
Dave busied himself with Charles as I got dressed. As we had planned, he started to pull the clothes off of the truck stop owner. By the time I was fully dressed, Charles was completely naked and still lying face down on the ground. His tall frame was curled slightly on the ground in the position Dave had moved him to get his clothes off. I had rarely seen him completely naked. Most of the time our encounters were with him behind me and me bound in some way, but even still he often only undid his fly to fuck me.
His body was mostly hairless, but fairly muscular. Dave was a bigger guy by far, but Charles may have been able to put up a bit of a fight if he hadn't been knocked out my surprise. Clearly Dave had thought that through.
I helped my friend push Charles through the bars and into the cage after I went in to retrieve my journals. We then closed and locked them just as Charles was starting to come around.
His hand went immediately to his head where there was a big red welt and a pretty prominent bump. He just rubbed it for a moment, sitting dazed on the thinly carpeted floor of the cage until he noticed he was naked.
"What the... where are my... what the hell?" He looked around and saw where he was and then out at us. "Open this fucking door," he shouted at us.
I just shook my head, afraid for a moment at his anger after so many months of being under his control. Dave put a reassuring hand on my shoulder and it gave me strength. Reminded me that I was not alone for the first time in almost a year.
"Where's my money?" I asked simply. That was all I really wanted. "Give me my money and we'll let you out of there. And then I'm leaving and you can suck the rest of the truckers off yourself for all I care. I'm done here."
Charles' face started to turn red as he glared at me, awash in hot fury. "You fucking bitch. Let me out of here now or you'll never get a dime of that money."
I nodded. "I have a feeling I was never going to see a dime of it anyway. You can sit in here and rot for a while. See how it feels. We'll check on you later to see
if you've changed your mind." I turned away from the cage and grabbed tightly onto Dave's hand for support. I was literally shaking in fear and excitement. Even though I knew I was safe from his anger, it was still terrifying to face it after being so powerless towards him for so long.
"You fucking whore!" Charles was yelling now. "Open this fucking cage, you cunt!"
I ignored him and continued walking towards the door to the stairs. "Dave! Whatever she promised you, she can't produce it. But I can. Let me out of here and I'll double what she's promised you and you can fuck this slut for free whenever you want."
I kept walking but I felt Dave pause. I looked up at him and there was anger in his face. He started to turn back but I squeezed his hand. "Don't," I said. "Let's just go."
He looked down at me and nodded. We opened the door as Charles continued to yell obscenities and let it slam shut behind us, immediately silencing him. His soundproofing job was well done, at least.
We hurried downstairs and exited quickly from the truck stop, practically running to Dave's truck. He opened the cab door and lifted me in easily, then climbed in himself. I was greeted immediately by Dani, her long red hair cascading down her gorgeous face and a tender smile that caused me to burst into tears the moment I saw it.
Dirty Diaries: A Darkly Erotic Novel Page 15