Paradise Lost
Chapter 9
My worst Humiliation and Degradation
"Join me in Playroom 1 at ten Jonah."
Interesting room when I had a look round it. Torture room would have been a better name for it I reckoned.
Ollie came in dressed in skimpy shorts and trainers and immediately told me to get naked. He fondled my cock and balls while looking me straight in the eyes.
"Does a girl doing this feel better than I do."
Quite honestly the answer was no. Girls really didn't have a clue how to satisfy us guys apart from opening their legs so I had to admit that to him blushing all the while. His turn to look smug.
Bent over the whipping bench first I hoped he remembered I had made love to him last night. The bench was an interesting piece of kit. I had to put my knees into shaped pads which were then levered apart until I was well spread. My shins were resting on a padded tray with straps which were used to secure me. My thighs were then secured in the same way to vertical pads. I was then bent over a padded roll bar and laid along a flat table with my wrists secured at extreme stretch. The table was lowered from the roll bar end so that my body sloped towards the floor stretching my lower body and butt. I was now totally disabled and at the perfect height to be punished or fucked. I guessed I was going to be fucked because Ollie swung my shin supports out more so that he could get between my legs, but that wasn't his game plan.
"I am just going to try some of these chastisers before I put you in the sling for a good fist fucking. My friends will be here at eleven and then we are really going to work you over."
I didn't like the sound of this.
He pulled my cheeks apart first and stuck both thumbs in me, no lubricant so it hurt.
"Please Ollie, don't enter me dry, that is so painful and damaging."
He replied to that by spanking me once for every word he uttered.
"Don't call me Ollie and I can do what I like."
My first eleven.
He picked up Mike's favourite tool then, the rubber paddle. I got five of those with varying degrees of hardness, so varying levels of grunts and screams. Next came the cane, that was five screams, they felt like a knife had been drawn across my butt. He picked up a whip then and I clenched my eyes shut and prayed he would be careful. If he used the whip too hard he would definitely cut me, another five and oh God did they hurt.
Ollie released me then but when I stood up I was shaking all over.
"That was interesting Jonah, I could tell with each stroke how much it was hurting you. With a lot of practice I reckon I will be able to place the cane very accurately for position and for the power I need to hurt just the right amount and I have two weeks to practice on you. I won't use the whip again because I don't want to split you if we are going to be fucking you."
Mmm, Mr. Nasty was definitely back and I was going to be sore tonight even if they left me alone for the remainder of the day.
I had walked around the room for a few minutes trying to get the stiffness and pain level down while he talked but now he wanted me on what looked like a Doctor's examination table rigged with stirrups for internally examining women. We had almost an exact replica in the sick room at the fitness centre where Sam and I worked. The differences with this one were that I could see how it could be split in two and also adjusted for height at both ends. It also had restraints fitted in different locations including the stirrups.
When I was on it on my back Ollie walked to the side and made me adjust my position, I guessed in relation to the point where the table split. He slipped my ankles into the stirrups and secured them and then a fairly wide strap across my waist and another across my chest just below my nipples. I realised all the restraints were very soft and padded. He stood at the foot of the table then with a remote control and started adjusting the stirrups and the head and foot height. When the stirrups had me spread very wide he started to swivel them backwards until my knees were level with my nipples. The position was quite comfortable because the table was also well padded so my spinal column was not prodding into a hard surface. He then undid some catches and slid the bottom half of the table away so that my arse was hanging clear, obviously to make it easy to enter me while standing. I had free movement of my head and arms but I could barely move anything else. A little height adjustment and he was satisfied. He disappeared then but came back about ten minute later with his three tennis friends from yesterday.
"Wow Ollie, what are we going to do with the slut today?"
"Well I thought I would open him up as wide as I could and then see if I can fist fuck him to orgasm. You three can follow me. While one of us is working his arse another can do what they like to his cock and balls and we can get blowjobs and hand jobs from the top end. Mike says we can't hog him all day he must do pool duty after lunch so we only have a couple of hours."
"Well I want my cock taken care of in a warm orifice so while I wait for his arse to become available I'm going to let him suck me gently to orgasm before I empty my bladder in him."
"Great idea Col, I'll follow you, but he can play with me while I watch Ollie fist him.
The start then was a cock and set of balls to play with in each hand, a cock using my mouth as a sleeve to get high with and I could feel Ollie starting to finger me. Thank Christ he was using lubricant this time or I would have been in trouble. I could feel myself being stretched as he added fingers and then when he pushed quite hard testing to see if his fist would go. He pulled out then and told Colin to put a pillow under my head so that I could watch the final assault. The walls were all mirrored and curved so I could see my arse with no problem. Ollie put plenty of Crisco in my arse and on his fist and then I watched as he entered me. When his knuckles went over my sphincter I screamed and burst into tears, it was much worse than when Adam had done it.
"Oh God, that hurts, please pull out," that was a completely wasted comment. He did hold still for a little while though until I had calmed down.
All of a sudden the door flew open and one of the camera men came in. "Sorry I'm late, can you start that again."
Ollie just grinned, pulled his fist out, cleaned up the outside of my arse a bit and then with a nod went back in, another scream but not as bad as before. Can you imagine how I felt though as the other boys resumed their activity. I was being filmed wanking two boys, sucking another and being fist fucked by a fourth one.
The four boys then decided to make a competition out of it. "The one who goes in the deepest gets to fuck his arse all night if he wants to."
I didn't think I would ever stop crying as four boys took turns fisting me and pushing the limit each time they went in. I had a face full of cum where they were depositing their excitement and then while each of them fucked me after deciding Colin was the fisting champ they made me scoop up their cum and eat it. Colin had already emptied his bladder in me, Ollie did the same after he had fucked me and made me lick his cock clean. The last two decided they would fill me at both ends so I was being pissed in the mouth and the butt. I was a mess but I could still feel the humiliation of the next bit. They wheeled the table over a drain raised it vertically and told me to empty my bowels. I could see the camera man capturing everything.
I think the term to sum up me would be `distressed.' I still shrank into myself being treated like an animal even though it had been going on for nearly three months.
Back in the centre of the room and they were playing to the camera now, pulling my cheeks apart to show my distended anus more clearly and then taking one of my anal lips between forefinger and thumb and rubbing them together. My squeals of pain had them rolling up and the camera man reverted to a tri pod because he was laughing as well, two of them pulled my cheeks apart with a couple of fingers each and spit into my anus.
"Filthy slut, I don't think any of us will want to sleep with you tonight. Let's spank him for being a slut."
"Ok but we mustn't damage him anymore Mike said. Let's just wank over him again and make him scoop up the cum and I want to see how much spit I can get in his mouth, then we can spank him for a little while"
They fingered me, rubbed my anal lips, wanked over me and spit in my mouth for about another half an hour. They all got in another fuck and deposited some in each end before calling for my partner, Adam. They made Adam watch as each of them spanked me about ten times each before releasing me to him. He was so shocked at what he saw when he took over he was speechless.
I was still secured on the table, my distended anus could still be seen clearly, now dripping with more cum and I had dried cum all over me with great globs of spit around my face where they had missed my mouth. My arse cheeks also looked interesting with ten clear lines from the cane and the whip, and the remainder was bright red from the spanking. The camera man kept filming until I was free of all the restraints.
Dearest Adam, he cleaned me up in a warm shower, creamed my orifice and my cheeks, dressed me and took me back to the dorm. It was still too early for lunch so he undressed me carefully and tucked me into bed while he went for a couple of the high energy drinks we consumed like water. I was a mess when I woke up but coherent enough to tell Adam what had happened to me during the morning. He was shattered by the degradation I had suffered and hunted down Mike to tell him I would not be fit to work for the remainder of the day. No problem, I missed lunch, drank some more Gatorade and slept until dinner time.
Mike's idea that evening for dinnertime entertainment was to show the film of my abuse.
"This is what you can put up with if you have to. Jonah will take the prize with this session for the worst abuse so far I would guess."
I was so devastated that everyone had now witnessed my total degradation that I couldn't stop crying and the Doc. put me out for the night.
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