© Copyright 2014 - Edruber - Used by permission
Storycodes: M+/m; D/s; captive; prison; fem; latex; catsuit; hood; toys; insert; bond; stocks; bdsm; bullride; anal; oral; climax; cons/reluct; X
I was sound asleep when something or someone was moving me around but, waking up like this I was sure I was home and wondered who and what was bothering me. As I was fighting off the intruder I received a hard stinging wack of a belt on my ass and I woke up real fast coming to realize of where I was and what was happening. He undid the belt on the leather shorts, pulled it down, pulled the plug out of my ass and slowly pushed a larger one in. This time it took a lot less time for the pain to go away and the pleasurable throbbing to start.
I fell asleep again until the sound of the big metal door opening woke me up. The officer came in and while unlocking my belt and removing the shorts and the plug, he told me that I would be working 3 days out of seven a day on a day off and Sundays off. I would be fed a very special diet that will be very nutritious but clear and easy to clean out with one or two enemas. I had not been given anything to eat since yesterday. I was taken to the crazy contraption but this time I was strapped in face and belly up.
A ring gag was shoved in my mouth forcing my mouth open and then a lubricated tube was shoved down my throat down to my stomach. A clear plastic bag ½ filled with a cloudy white liquid was attached to the tube, and a valve was opened and I was allowed to watch my breakfast going down directly to my stomach. When all the liquid was inside me, they removed everything and unbuckled me from the contraption. I was taken back to the room and told to relax until the afternoon, so, I sat back and decided to watch t.v.and to my dismay the only programs on this t.v. where pornos of men fucking men, large penises, blow jobs and sex in rubber. I was surprised that while watching them I got a painful hard on but, as per their orders I was not allowed to masturbate and in fear of loosing my teeth, I obeyed.
At about 2.30 p.m. the officer came in with a bunch of rubber clothing and boots. It was the same outfit as yesterday with head hood and all but no plug and the zipper at the crack of my ass was opened leaving it open and vulnerable for the first rape I would be experiencing. I was walked over to a hallway to an elevator, up about five floors and in a short hallway with a double mahogany door at the end. As we walked through the door the large room was dimly lit with hidden ceiling and floor lighting, the floor was beautiful shiny black marble and the walls beautiful mahogany wood.
There where several pieces of specialized furniture like, a double bed with a rubber mattress it had an elevation in the center where ones ass would also be elevated for easier assess and pleasure. At the head of the bed there was a circular cut out and a very comfortable stuffed reclining lounger that fit just under and at the right height for the person being fucked be able to give a blow job thus satisfying two at one time.
On another area there was a very well upholstered plush leather table, this was like a drawing table at just the right height and angle for one to bend over it and be taken from behind and in the front of this contraption there was a stuffed chair adjustable to move in at the perfect place for oral pleasure. There was a padded bench with straps hanging from it and to one side a wooden cabinet with glass doors full of belts, whips, paddles, dildos and a lot more that I did not recognized.
The officer simply told me to do my best, obey and remember my teeth. He left closing the door behind him. As I walked around slowly, the door opened behind me, closed and I could hardly hear any movements. I was afraid of turning around and did not know what to do until I felt a hand on my right ass cheek just softly touching at first but soon thereafter started to squeeze and grabbing both of my cheeks and squeezing them and pulling them apart.
He walked me over to the stuffed angled table and made me bend over it then, while he was opening and taking out the condom from it’s foil, he took my hand and guidedit to his enormous harder then a rock penis. This was the first time that I held another man’s penis in my hand and since the room was semi dark and I had not looked at the man or the penis, it was an event of high sexual awareness. As I caressed the penis up and down, he pushed my hand off it and I could feel and hear him placing the rubber condom on it.
He placed my hands and arms at the side of the contraption and shoved a lubricated finger into me, rolled around inside a little, then got into the position behind me and aimed the head at the entrance of my asshole and a cold shiver came over me this was it! the pressure was starting to get that enormous human appendage inside of me. The apprehension, the sexual high, the conflict of pleasure and shame, the fear, was all together in one emotion, one minute.
It was the most incredible moment of my life and it started. I was trembling and perspiring. As the pressure started I was sure this was not going to happen, it was just too large to fit, no way my hole could open that much. But to my surprise and pain, suddenly the head penetrated past my sphincter and the pain was almost unbearable if I could have moved away from it I would have but, I was pinned and had to endure. He must have noticed my predicament and stopped all movement for a few minutes until the pain got a little more bearable. That’s the only time he spoke He said, "Is it better now?"
I responded yes sir, he started very slowly pushing in until I felt his body touching my ass cheeks telling me that the thing was completely inside. Now the pain was almost gone and I started to experience small constant inside mini orgasms which was the greatest pleasure I had ever had. I had never had this much pleasure in sex with a woman by a long shot. My body was trembling and I was in a trance while this guy just kept moving in and out a couple of inches at the time.
I had not noticed that more men had come in the room until I felt someone grab my right hand and guide it to his dick and at this moment another guy which I was able to see because he sat in the stuffed lounger in front of me then lifted my head and guided his condom covered penis into my mouth.
I had never done this but with so much pleasure being dealt me by the dick working my ass, I felt pleasure in giving the rod of ecstasy in my mouth the best possible work out my tongueue and mouth could provide. I rolled my tongue around the head for a while then pushed it all the way to the back of my throat and when I started to gag I moved my head up and down on it so as to slowly and gradually get use to deep throating him. The guy next to me poked me to move his penis because with all the ecstatic things happening to me, I completely forgot his tool in my hand.
Another one grabbed my other hand and guided to his tool. It was becoming difficult to concentrate on so much sexual abundance at the same time. The guy in my ass started to bang into me with ferocity he seemed to have gotten even larger he was moaning very loudly until suddenly he just kept pumping at a slower pace and harder.
He finally stopped all movement and just laid on top of me breathing hard, but his penis was not deflating. I guess the excitement caused by the guy in my ass got the guy in my mouth to also explode. He grabbed my head with both hands and started to pump all the way to the back of my throat and I could feel the twitches of him coming. The two guys got out of me and went over to the bar in the back of the room. Now the next guy was the first to talk to me and he said, "Take all of the rubber outfit off except the hood".
Once I was Naked I was shivering because I had sweated a lot inside the rubber and now the room was cold. The guy handed me a towel and I toweled myself dry. He then moved me over the bed, placed me in the position of vulnerability over the hump and my face and neck hanging over the circular cut out in the head of the bed. Now I was waiting for someone to fill the vacuum I was feeling in my ass. He came behind me on the bed opened my legs apart more, then I felt the head pressuring to get in, this time it went in easier and did not hurt, just started giving the same pleasure as before with the mini orgasms inside.
The other guy sat down in the chair in front of me and the double fucking started all over again. It took the second team at least 40 minutes to come because, whenever they started cumming they would stop and calm down so as to prolong the act. I was under the impression that once they would cum the job would be over for today but, I was made aware of the conditions of the contract when one of the guys made a comment to the others that they had only used up 3 hours so far and they had 4 more hours to go.
Well as great as this had been I was already exhausted. The first two came back and took me off the bed and tied me belly down on the padded bench. I could not see in that position but heard the door of the cabinet open and the guy said as he was choosing his tool of pleasure, "His ass need’s a good heating up, it will make it a lot better fuck".
The other guy answered by saying, "Lets be truthful this is the best fuck we ever had so far, well worth the price".
I felt the first slap from the leather paddle with tears coming from my eyes, he alternated the cheeks and after a while it stopped hurting so much because my cheeks where becoming numbed. After he was satisfied that my ass was at the right temperature the first two started the fucking all over again where I was tied on the padded bench. When they finished their time was up and they left me for the other team for the last double fuck. Before they left they untied me and left me to get back inside the rubber outfit for the walk back to my room and a well deserved shower.
The next time I was in the room the first two guys coming in were the Warden and his assistant. BIG SURPRISE!!! Dan and One of the older men at Dan’s house. The older guy was the warden and Dan was the assistant. They sure went to town on me for 3 or 4 hours. Dan was very large, about the same size as the first guy maybe a bit larger. I was bent over the angled table he got all the way inside of me, but then while inside he stood me up put his arms under mine in a full Nelson stance, then lifted me off the floor and started moving me in the way that I was banging into him back and forth being impaled on his large penis. The Warden just stood in front, playing with his engorged dick, which was not as long as Don’s but was thicker, probably more then a couple inches in diameter.
Being the big athletic type, Don had an incredible stamina.
He was banging me in that manner for at least 15 minutes already, moaning and grunting obviously enjoying it. Meanwhile I had leaked pre come a lot inside my rubber suit with the first guy, but with Dan I finally ejaculated the largest amount ever. Of course after ejaculation my sexual libido had diminished almost completely and Don’s continuing banging, became somewhat painful and tiresome. Now I had to fake and moan as if enjoying it. He finally bent me back over the angled table and pumped ecstatically for about a minute and then stopped and just laid on top of me for a while, then pulled out of me and luckily they both went over to the bar for drinks while I had the chance to recuperate enough to be able to take the larger diameter of the Warden.
About 20 minutes later, the warden went to the cabinet and took out the nipple discs, strapped them on me and turned the button on, driving me in a frenzy needing to be fucked again. Well, fucked again I was, and as he pushed it into me I felt the pain of a virgin again but he was not as considered as the first guy, he just started banging away with all he had. Of course after a few minutes the pain subsided and the inside mini orgasms, turned into large orgasms my body was trembling uncontrollably and it was lucky that I bent over the table because my knees where unstable at this point. Lucky for me when he got larger and started to come, so did I together with him.
He laid on top of me resting for a while, then pulled his large dick out of me with a pop, and to my surprise, stood me up, turned me around and kissed me and just held me tight against him with both hands grabbing my ass. Before they left Dan asked me if my room was O.K., then told me that next week they would transport me to his house for the weekend for some fun and barbeque by the pool.
In the next week, I started settling in on the new life I was forced into. I had thought that being exposed to constant sex this way, eventually the pleasure and the internal orgasms would diminish but, I was amazed that it turned out to be quite the contrary, it just kept getting better and more intense every individual penetration and every day. I overheard guards talking that they where paying as much as $ 1,500.00 dollars each to be in with 3 others in the room for 7 hours.
There where some very rich cons in here and paid the price for what they wanted. I also noticed that the ones that where gay, preferred to get me naked and the others wanted me in full rubber with my genitals hidden out of the way inside the rubber outfit. The day came when I was given my original regular clothing back, and was told to get ready to leave in an hour.
When we arrived at Don’s house, I noticed that a room was added by the pool and after being escorted into it I saw that it was his sex pen or, his dungeon. All the contraptions from the jail where duplicated here and there was an addition to them. The base of it looked like one of those mechanical horses from cowboy bars. The saddle however was in the shape of a “U” with the front seating part a little higher then the back and the back had seat belts built to it in the front part of the “U” there where handles half way up and leather cuffs attached to it. There where some more leather belts hanging from it which I did not figure out what they where fore. It had a remote control laying on top. I was left in this room with the door closed, as per orders naked.
When they brought me in as we past the pool there where 3 men sitting around in rubber swimming shorts drinking wine. Dan came in after about a half hour and told me they wanted to have some sex first and afterwards we would all go for a swim and enjoy some steaks. He went out talked to the men for a few minutes, then returned and told me they voted for rubber so the guard will come in and help me dress up in the appropriate rubber outfit.
The outfit I was dressed in was head to feet, with an opening at the ass crack, lucky for me the devilish nipple plates where already built in this outfit and there was hidden button by the collar to activate it. A 2 inch leather belt was placed around my waist and it had d rings at the sides. After the head hood was pushed on my head leaving just holes for my mouth, nose, and eyes, I was bent over the tilted upholstered table to wait for the parade to come in.
After a while they came in except the warden. As usual I felt hands squeezing and caressing my ass, my back, a couple of times fingers pushed in to me and then Dan called everyone’s attention and showed them the new hot rider as he called it and said that he was going to take the first ride to show everyone how it worked. At this point he went over to the cabinet and took out a plastic bottle, then came over to where I was bent over and smeared the oil all over my rear and part of my lower front. He then walked over to the ride and smeared some of the oil in the front seat area only. He guided me to the contraption and told me to get on it but in the front part only and not get any oil in the rear seating area.
After I mounted it he cuffed my wrists to the cuffs in the front handle then he mount it behind me and slowly pushed his long large dick deep inside me. Now I was able to just slide down into it at this point, he buckled his seat belt around himself, then took the straps that were laying on the side and clipped them to the d rings on the sides of my belt and d rings on the sides of his back rest. It was becoming clear that as the horse moved, I would be sliding back and forth, up and down on to his dick and of course the side adjustable belts where to make sure I did not fall away from the dick, it only allowed about 2 inches of space between us.
He punched the remote and the horse started at a trot at first throwing me severely almost up and down on the monster dick he change buttons and we galloped which put us at a forward and back easy fucking mode. If he changed to a slower gallop the fucking motion was shorter and faster and then an all around in and out was the rodeo bucking motion. I was so internally well trained by now that I could have continuous orgasms to a point of convolution with out having to ejaculate. I could now last all day and all night in pure ecstasy.
That came in very handy on this incredible machine because, Dan lasted about 20 minutes and afterwards the other two lasted at least ten minutes each, and by the time they finished, Dan hopped on it again for seconds. The advantage I had over all of them was that I just kept on orgasming like the Eveready battery. The longer, the better. The pre come drippings where the way I relieved my gland ever so slowly with out loosing my libido. Dan finished in 10 minutes and got off leaving me on the horse, while they all left the room for the showers.
After sitting up there at least 15 minutes by myself with my ass feeling empty and throbbing, the guard came in, undressed me from the rubber outfit except for the head hood. He told me to shower put some powder on my body and bend over the table. I did as ordered and heard the door opening then hands caressing me and grabbing me by the shoulders, lifting me to a standing position, and turning me around at which time I saw that it was the warden in front of me, holding me tight grabbing my ass, and kissing me.
He walked me over to the cabinet, got the oil out and spread all over my ass cheeks, then walked me over to the horse and helped me mount it. We went at it for at least an hour and half, with resting periods in between. After he left the room, the guard came back in, took me to the shower and afterwards helped me into the rubber outfit again. I was allowed to join the barbeque party dressed that way and not given any food because of my special diet. I was given a glass of wine, and during the rest of the afternoon and evening I was told to sit on the guests laps as they massaged and played with my ass and tits. I was driven back to the jail around 2 in the morning, and the daily routine was restarted.
I must have made a fortune for the Warden in the 3 and half years that I was there. When I was finally let go I had no record because I never was convicted of anything. They gave me $65.000.00 dollars I was allowed to move into Dan's house. And now I earn a commission of half of the bids by going in to the prison twice a week, at this point I was too far gone to do anything else.
I hope you enjoyed the story and if you wish to tell me how much, you can contact me directly at [email protected].
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