ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.
The next few days went by without much issue. I scheduled in some plug time in the evenings, being careful to set a timer so I would know when I met my quota. It was so easy to get lost in the videos he had in the drive although they did make the plug time feel that much easier. I still remembered why he had given me a bigger plug in the first place and I decided to try and avoid being blindsided like that in the future. I spent all my plug time on my hands and knees with my butt high in the air. I worked my muscles, constantly holding onto the plug, ensuring that even if I became relaxed I could hold it in place. By the time my next evening with him came around, I wasn’t having much trouble getting it inside me and even less getting it out. More importantly I was able to control the two.
The next evening with him, however did not go as expected. It was Halloween weekend, and he decided that in his words, as a treat, we would be changing the formula. The outfit he had picked out for me was a skanky Raggedy Anne costume, complete with red knitted wig and blue hat. The dress was quite short and left a good portion of my ass cheeks visible. My caged cock dangled just below the hemline as well and he did not provide underwear for this costume. There was also red and white striped stockings and white platform dress shoes to complete the look. He had printed off a picture of a girl wearing a similar costume as a makeup guide and I followed it with surprising accuracy. Big rosy blush marks on my cheeks along with mascara to accentuate my already long eyelashes. A beautiful shade of pink for my lips to complete the look, and finally, the plug went in.
I came out of the bathroom and found him as usual in the living room. The computer was set up in its usual place except there was something on the floor covered in a sheet just behind where I usually would be kneeling. I looked at him curiously and he spoke up right away.
“I have a little surprise today,” he began, “First, let’s have a drink or two, as a treat.”
He handed me a cooler and I took it warily. It was sealed so I didn’t worry about it being drugged but something still felt off. I took it, skeptically, and began drinking. He sat next to me on the couch and we watched a sitcom and I found myself drinking faster just to pass the time. By the time I was on my fourth beverage I was feeling a buzz and began to get giggly despite the sitcom being a bore. He was making jokes and even though I despised the man, I was genuinely laughing. This caused some inner conflict that slowly faded the more tipsy I got.
“Okay time for the evening’s festivities.” the man said, standing up.
I hopped to my feet, almost falling on the platform shoes. He ordered me to kneel down on all fours as per usual. I did so with more energy than I might have with no alcohol in my system. Although I would look back on this and cringe, I stuck my butt as high as I could in the air and wiggled it around.
“I wore my plug over here, see?” I said loudly in an attempt to win some brownie points.
I felt a slap on my ass and jumped.
“Good girl. Go ahead and hit play.”
I clicked the pause button on the laptop and a video began.
I began watching and the usual stuff began happening, words, pictures, clips, etc. What was different this time, was there didn’t seem to be any girls in the video at all. I mean, there were, but not real girls, just crossdressers and traps. I watched and in my boozy state I zoned out fairly quickly. Eventually I felt something pulling at the plug and it almost slipping. I clenched, allowing my ass to suck it back in and used my muscles to hold it tight. The tugging sensation continued however and after a short game of tug o war I turned my head to find him behind me. I lowered my headphones to find out what was going on.
“Wow, look at you, I can tell someone has been practicing. Now let it come out, we are going to try something else.”
I was buzzed and relaxed but I knew that I probably wouldn’t want to try ‘something else’, as he phrased it.
“I think that was a good size, don’t you? It wasn’t falling out…” I reasoned.
“I’m not putting in a different plug right now, don’t worry.” he reassured me.
I noticed he was only wearing a bathrobe now and could see his cock hanging down as he crouched to pull the plug out. My eyes went wide and I tried to turn but his fingers were still gripping the plug inside me.
“Calm down.” he said.
“We had a deal!” I said, fear bubbling up, “You can’t fuck me! That was the deal.”
“And it still is. I’m not going to fuck you unless you want me to.” he responded calmly enough. “But the deal was, anything goes, aside from that. So please, put your headphones back on and watch the video. I’ll stay beside you so you don’t have to worry.”
He moved up to my side and began tugging on the plug again. This time I relaxed and let it slip out. He put it down next to my face which was low near the laptop. He began reaching and fiddling with something hopa escort behind me, at which point his leaning caused his groin to push against the side of my face. I felt warmth on my cheek and turned to find it was the head of his cock. As I moved my face away there was a strand of precum connecting his cock and my cheek and I wiped it quickly away. Just as I was moving past the unwanted contact I felt something dull pressing against my hole. It pushed harder and I decided to forgo the fight and accept whatever it was inside me. It moved about two inches into me and as I waited for the skinny part of the plug to anchor into me, it never came. Instead he seemed to stand up and walk back to the couch, sitting down.
The plug was a little uncomfortable although it didn’t feel much bigger than the thickest part of the one I came in with. I didn’t understand how it wasn’t falling out without being anchored but I dropped it and focused on the video again. He stopped me twice more in the following half hour and gave me shots of vodka, which I accepted without a fight, from my kneeling position. I was starting to feel drunk but was not about to complain about free booze as it was helping me get through the humiliation I was being subjected to. The video seemed longer than usual but had a rhythm and theme to it. The first part focused on dressing up nice and make up, the second was sucking and blowjobs, and the third, which had just began was about getting fucked.
On the screen there was a skinny crossdresser wearing the same outfit as me setting up a camera. She then got down on all fours in front of it and a man walked behind her. As he entered her I could practically feel myself being entered as well. It only took a second to realize I was. The plug was moving inside me. I looked to the right and he was still sitting on the couch. He was holding a remote and he looked at me before pressing a button on it. It was at this point that I realized that it was not a plug inside me after all but a dildo. I looked behind me and saw that the object covered by the sheet was in fact a fucking machine, and it was currently fucking me.
I looked back at him and pulled one earphone up when he gave me a look and said.
“Watch the video.”
I went back to it and felt the machine slowly push the dildo all the way into me before pulling back out. I focused on the video to distract myself when I noticed there was something familiar about the video. It didn’t take long to figure out what it was exactly. The outfit looked the same because it probably was the same. So was the living room on the background, and the man behind her pumping away. I looked back at him and he was smiling.
“Like my little home movie?” he asked.
“She was a good whore.” he sighed.
The dildo inched in and out as the trap on screen tried to keep her composure. The biker grabbed her skinny biceps and pulled her back giving me a view of the cock pummeling her hole. Her mouth opened wide and her brow furrowed and her caged cock began spraying cum out on the ground in front of her and she squealed rhythmically as it happened.
I felt a pulse of energy as the dildo entered me again and again. I wasn’t in control and with each progressive pump, that thought overtook my senses and pleasure began to build. The more I tried to fight it the more apparent it became I was going to cum from this. I looked down and away from the screen in a desperate attempt to stave off the inevitable.
“Head up, you don’t want to miss the big finish.” he said.
He must not have known that I was currently fighting in the throws of pleasure because when I looked up a look of revelation came over his face and he grinned. I was trying hard not to show what I was feeling but that seemed to show it even more. I looked back at the screen and saw him push the girly boy facedown again, into his own cum and then thrust slowly and powerfully into him. I saw the spasming of his dick on the out thrusts and heard the grunting accompanying it. He held it half way in before pulling out slowly.
I felt seconds away from cumming myself but just as I was about to lose it the dildo pulled out all the way. This is when I noticed I had been rocking myself backwards to meet the thrusting of the machine as I continued for a few beats after the dildo was removed.
On screen the man stroked the girly boy’s hair as she licked up her cum from the floor. When he was satisfied she had cleaned it well, he helped her to her feet and she began to pull her panties back on. As she bent to pull them over her knees a trickle of cum came out of her butt and ran down her leg. Once her panties were secured she received a slap on the ass and then walked unsteadily to the front door and exited the house, still in costume. The man walked to the camera and the video cut out. I looked at the time and saw I still had one hour and a half left.
As he helped me to my feet, I felt something run down my thigh and had a panicked thought that I would become the girl in the video. I realized it was only lube and calmed down as he led me to his kitchen. He pulled a chair out for me and I saw it had a 6 horasan escort inch suction dildo stuck to it. I sat on it carefully and he pushed my chair in, then taking a seat opposite me.
“So I thought it might be time to take another look at the arrangement we have.”
“I only have two weeks left right?” I asked, nervously.
“Correct. But, I have an offer for you that would be a great opportunity. Would you like to hear it?” he asked.
“Well, I really only want to do two more weeks of this.” I said, knowing full well his offer would come with some sort of tempting reward or veiled threat.
“I think you should hear the offer.” he said and I realized hearing him out wouldn’t be optional.
“Okay.” I relented.
“Okay?” he asked and I quickly corrected myself.
“Okay, daddy”
“Good. The offer is this. Instead of two more 3 hour shifts at 100 a piece. You agree to 5 more full day shifts, at 1000 a piece. That’s $5,000 more than you would have made.”
“Uhhh…” I was confused.
“More would be expected of you of course.”
There it was. I knew he’d try to fuck me. I knew that this would be the new expectation going forward for that kind of money.
“As in?” I asked. for clarification.
He smiled calmly and stared at me, leaving a long moment of quiet.
“As in you would agree to have pictures and or video taken of you. They would not be posted anywhere someone you know could find them. You would also agree to slight and reversible changes to your physical appearance. Such as temporary tattoos, tanning, hair colouring, and so on. You would also have to drink and take soft drugs as requested, nothing addicting or long lasting.”
I wanted to say no immediately after hearing videos and pictures would be permitted but I also had 5000 reasons to hear him out.
“And what about the no sex rule?” I asked hesitantly.
“For $5,000 you will have to do some things you don’t want to do. But you will not be expected to suck cock or be fucked by a cock. Unless of course you agree to it later on.”
“Things I don’t want to do?” I needed clarification.
“Yes. I assume everything you have done so far lands in that category. Save for the last task. It seemed like you genuinely enjoyed that one.”
I needed to think about it. I was certain that taking this offer quickly might prove a mistake.
“Can I get back to you tomorrow.”
“No. You will have to tell me now, yes or no. If it’s a yes we can even begin tonight if you can stay later. I’ll make this a bonus night and you walk away with an extra $1000.”
I thought for a moment and quickly told myself if I was going to humiliate myself for this asshole I might as well make some money doing it.
“Yes”, I said, too enthusiastically, “I mean okay, I’m game.”
“No take backs now? I said the pictures and videos wouldn’t be posted anywhere they would impact you negatively but that exception will change if the contract isn’t fulfilled. Understand?”
“Yes” I said. I had come this far, what was 5 days for an extra 6,000.
“Okay, back to the living room.”
He led me back and I took a seat on the couch. I was given a vodka cran and he went about setting up his camcorder on a tripod. The red light was flashing as he came and sat next to me, his cock semi hard and poking up.
“Down on your knees, take it in your hand.” he said looking at me and then back down at it.
“Wait, we agreed-” I began but was cut off.
“We agreed no cock in your mouth or ass unless you change your mind. That’s it. Think about that before you speak up next time.”
Well, I guess this was the catch I thought to myself.
I slunk down between his legs and reached my hand out tentatively making contact with my fingers. It was warm and soft and as my hand applied more pressure and I gripped it, I felt the rigidity grow.
“Use spit, get it nice and wet all over.” he instructed.
I spat into my hand and gripped it again, spreading the spit around up and down but it only went so far.
“Spit right on it. Get it sloppy.” He guided again.
I spat directly on it this time and carried my hand over the head. I repeated this a few times until his shaft was shiny wet and pubes were matted at the base of his cock. His head seemed to be producing pre-cum that mingled with my spit with every up stroke I gave it. His balls were soaked with the dripping saliva and he must have seen me staring.
“Rub your face into them while you jerk me.”
I gave him a look of disgust and he matched it with a look that could only be described as saying ‘I dare you not to’. I inched closer until the wet sack was pancaked across most of my face. The musky aroma overwhelmed my sense and I focused on jacking him to distract myself. A hand met the back of my head and moved my face in circles on his balls, making contact from my chin to my forehead. It was in this moment that I began to regret altering our deal.
This continued for a while until he yanked my head back. He had me stay in position and got up. As he left my limited view I realized the smell of his balls was still very pervasive. His içerenköy escort escort musk had attached itself to my face as of he had marked his territory. As I pondered my new perfume, a panicked thought came to mind. Was my makeup okay still? Why did I care? Were his ‘training’ videos rubbing off on me as well as his balls? I heard a lot of movement behind me and then felt the blunt tip of the dildo behind me again. He pulled it forward until the head popped inside me and then returned to his seated position on the couch and once again gripped my head.
I returned to jerking him as he rubbed my face into his wet balls and taint. He started up the machine shortly after. The jelly cock did its work on me but this time I was aware of the potential urge to meet the thrusts of the machine. I told myself I wouldn’t allow that to happen again.
“I knew you’d take the deal. The guy in the video took the deal too. Such a good slut too. Lived next door and would sneak in and out through the side door dressed so his parents wouldn’t catch him. Sucked my cock in his mother’s wedding dress once. Little slut would do anything for me.”
“Whaf hamppen?” I asked, unable to articulate the question due to the risk of a ball invading my mouth.
“Said no to the last contract I offered. Lucky little slut. A couple weeks later she begged to take the deal. Wanted the money and the cock again. So I took her back, but only for a trial session, no rules. She agreed.”
“And?” I asked, never more curious.
“I had him skip out on a family movie night. Sister was home from college and everything. I set up as usual, had him wear her highschool cheerleading outfit. I was sitting right here and he was riding me facing the camera. Right before he was about to cum I had him begging me to fill his ass up. Had him begging me to let him cum. When I did, his ass couldn’t take it, cum was pouring down the sides of my cock and he sprayed his own body and face. It was a mess. That bitch did some disgusting things for me and thanked me for it. After it was all said and done, I sent him on his way home. What he must have found out shortly after was that I had casted the last sixty seconds or so to his family’s TV. He walked into his house right as they were probably running out of their basement rec room. Teaches him for trying to sneak in still dressed up.”
The pumping of the cock and the story he told seemed to have a strong effect on me and I felt that familiar pleasure build. I didn’t get it. I hated this man and the story he told only made me hate him more. If that was true, why was the pressure in my cage growing as his balls rubbed in my face.
“I never saw him after that. Maybe once or twice in passing but his eyes never met mine and his family moved a month later. Likely as a result of our little showing. If there’s something you should know about me its that I expect people to stick to their word. Whether it be a yes or no.”
The thrusting had gotten intense enough that it caused me to open my mouth in a silent moan. One testicle invaded my mouth and practically filled it up. His hand gripped my head tighter preventing me from spitting it out and I tried to use my tongue to push it out. I began to make a protesting sound but he cut me off.
“The agreement was you wouldn’t have to suck cock. Never said a stray ball wouldn’t end up in your mouth. Keep that tongue work up though.”
It didn’t occur to me that he would enjoy my tongue pushing on his sack. I continued the motion, now out of obligation rather than reflex.
“You’re backing into it again. There’s hope for you yet.” he remarked.
Shit. He was right. I was rocking back and forth on my knees to meet the thrusts of the dildo. Unfortunately him drawing attention to it did little in the way of discouraging it and I continued rocking, albeit in more shallow strokes. The pleasure was steadily building and I hoped this would end soon.
My mouth was now overflowing with saliva and I swallowed just to clear up some room. The action caused a second testicle to enter my mouth. I twirled my tongue around, massaging them as I worked his slimy cock with my fist. The dildo continued to invade my hole and I realized I was going to cum soon if it continued. I looked up past his cock and our eyes met. He held up the remote and clicked a button. The dildo began vibrating as it pumped and my ass was engulfed in pleasure. My eyes fluttered before I got myself under control again and he chuckled.
“Tell me when you are close.” He said and I knew cumming wasn’t going to be optional.
It didn’t matter because at this point I wanted to cum. I felt like I had earned it, despite being disgusted in what I was doing. It wasn’t long before I looked up urgently and made a sound around his balls. He sat up more until his cock was pointing straight up and slightly out. I pumped him hard and felt the dildo inside me suddenly vibrate harder and take deeper faster strokes. That was it. My cock erupted and cum began filling and dribbling from the cage. I had never experienced anything so powerful before in my life. My whole body tensing up, I let out an involuntary high pitched groan. At the same time he pulled my face back and cum began shooting and pouring out of his and the hot semen splattered on my face. His balls popped out of my mouth and before I could close it a gob of cum fell inside. The flavour overwhelmed me immediately and even in the heat of my climax the taste was pervasive.
