“Oh God! It hurts,” I cried out.
Her knuckles were pushing against my anal rim. She pushed harder and twisted her hand back and forth. Then suddenly she drove it in like she was throwing a right hook.
“N – o – o – o – o…,” I screamed, as her hand fully penetrated my ass.
I whipped my head back and forth and screamed even louder. But that was only the beginning. She pushed in even deeper. I could feel her forearm stretching my hole even bigger. Her fingers rubbed my inner sphincter and dug into my bowels.
“I bet you liked that,” she laughed, as she doubled up her fist and started hammering my insides. Back and forth she went, using me as a punching bag. The fist fucking continued for what seemed like forever before she took a rest.
Slowly she pulled her arm back, but it put her fingers in a perfect spot to massage my prostate. Moments later a pool of unspent cum flowed from my caged cock.
There was no escaping the continued torment. I couldn’t believe Margo left me with such a perverted sadist. What more could she do to me?
Finally, after fisting me a second time, she pulled her hand from my ass. I’m not sure she unclenched her fist either, because it hurt just as much coming out as it did going in.
My tears continued to flow, as she left the chamber one more time. I didn’t think I could take any more. Luckily I didn’t have to. Lilly returned and released me. I was locked in a cell in the back of the chamber for the rest of the night. There was no bed, but that didn’t matter. At least there was a rubber mat on the floor.
I had a very restless sleep for the remainder of the night. Sometime in the late morning I heard a key in my cell door. When I opened my eyes, Margo and Lilly stood there looking at me.
“Had enough fun for one night,” Lilly asked with a shit-eating grin on her face.
“Yes, Mistress.”
“Well, come on. You can clean up in that room over there and then head home.”
“Thank you, Mistress.”
I went in the bathroom and showered. God, my ass hurt. Between the whipping and the brutal rape, my ass would never be the same. After a few minutes I came out with a towel wrapped around me. They put a pink diaper on me and a pair of ruffled plastic pants. I got a funny feeling about this.
“Here, put this on,” Lilly said, handing me a short frilly girl’s nighty, but in an adult size.
I definitely didn’t argue, knowing what she would do to me if I did. I pulled it over my head and she buttoned it in the back. It was really short, showing off the fancy pants if I moved just right. She put a blond wig on my head with pony tail-like things on the sides tied with pink ribbons. That, as well as a pink adult sized binky and a doll for me to hold, completed my outfit.
“What about my strait jacket and stuff?”
“It’s already packed and in the car.”
We went upstairs into the store, where I was forced to stand and wait while they talked. I thought it was a little weird that people would look at me funny when they were in a porn shop to satisfy their fetishes.
“I’ll call you about Jerry’s party,” Lilly said, as we left.
On the way home, Margo pulled into a McDonalds. At least we didn’t go inside to eat. I’m sure she would have sat me in a child’s booster seat so everyone could see me. The drive thru was bad enough. She ordered herself a burger and fries. I got a Happy Meal. When we got to the pick-up window, they took their time, so most of workers could look at me, while we waited for our food.
“So, was she a little brutal on you last night?” Margo asked, as we ate in a park a few blocks away.
“Yea, she raped me really hard and then fist fucked me.”
“Well, I guess we can check that one off your list.
“I didn’t have that on my list.”
“I would have sworn I saw it,” she chuckled.
When we finished eating, she handed me the trash and told me to get out and put it in the garbage can.
“But someone might see me like this?”
“So.”
Finally I got out and walked towards the receptacle. It was nearly thirty feet away from the car.
“Hey, don’t forget your pretty, little dolly.”
I reached in and grabbed it before heading out into the open to deposit our trash.
Suddenly I heard her yell, “See you in about an hour.”
She sped away, leaving me standing in a public park, dressed like little child and holding a girl’s doll.
“An hour,” I whispered to myself.
Moments later she came around and stopped several feet away. I hurried towards the car, but she refused to let me in.
“Be standing right here when I get back, or I’ll leave you here until dark.”
Then she drove away, leaving me to my misery. Luckily there weren’t a lot of people around. I walked over to a bench a little ways away in the shade and sat down, hoping no one would notice me. Yea, who would ever notice a full grown man dressed up in pink baby doll pajamas holding a doll and sucking a binky?
A few minutes later a lone guy pulled up in a black Mercedes and parked where Margo had. He watched me for a minute or two before getting out and walking my way.
“Oh fuck,” I whispered to myself.
“So little girl, you want some candy?’ he said jokingly, as he sat down next to me. “What’s a sexy thing like you doing out here all by herself? I bet you’re looking for a little action, aren’t you, sweetie?”
“No, Sir. My Mistress dressed me like this and will be back to get me in about an hour.”
“Your Mistress… in an hour,” he chuckled. “Well, let me tell you something. That gives you plenty of time to do something for me. Now we aren’t going to wander around and look for my lost puppy. That just takes too much time. We’re getting directly to the point. We’re going over there in the bushes, and you’re going to get down on your knees and give me a good blow job, or I’ll call the cops and have you arrested for soliciting sex here in the park.”
“You can’t do that.”
“I can’t? Watch me,” he said, as he pulled out his cell phone. “What’s their number? Oh, I know… it’s 911.” He started to push the buttons.
“Okay, okay… please don’t call them. I’ll do what you want.”
We walked over in the bushes and followed a short path down to a small clearing. When he stopped, he undid his pants and pulled out his cock.
“Get on your knees and suck me off, and you’d better do a good job.”
“I’ll try, Sir, but I’ve never done this before.”
“Yea, right!”
His flaccid dick hung down over a set of fairly large balls, but I knew that it wouldn’t be soft very long. I knew when I got it hard, it would be considerably larger.
I leaned in and ran my tongue along its soft shaft. Immediately it started to grow. I kissed it and continued to lick, running my tongue up its ever hardening length.
Before long the mushroom shaped head of his cock was in my mouth. I sucked on it and flicked my tongue over the end. I tried to push my tongue into his piss hole, as I continued to lick. He seemed to like that, but finally he was ramming and jamming his hard dick deep in my throat. I tried to remember what I was told – breathe through your nose. As it pushed over the back of my tongue, it triggered my gag reflex, but I fought it back. I thought I’d puke a couple of times, but he was relentless.
“Tip you head back further, boi” he demanded, “and look up at me. I want to see your pretty blue eyes, faggot.”
I did and soon realized his entire cock was on my mouth. His dark pubes were rubbing on my nose, as his balls bounced against my chin as he face fucked me. Before long he pulled my head in tight and blew his entire load down my throat.
“Suck it all out, boi. Taste every drop of my precious juice.”
I did as he asked, but wondered what this boi stuff was.
“Not bad for a beginner,” he remarked, as he pulled out. “I come by here every
day at one thirty if you’re interested. I can give you loads of practice. You’ve got potential and with a little bit of training you could be a great cock sucker”
“We’ll see,” I responded, knowing it was never going to happen.
“Don’t ever say never.”
“Tell you what… give me the name of your Mistress and her number, and I’ll see if I can arrange a daily meeting to help you along your journey.”
“I can’t do that, Sir.”
“What was that number again? 911!”
“Okay, it’s Margo Roberts. Her cell number is 541-7737.”
He laughed, as he zipped up his pants and walked back up the trail. I could hear his car start up and leave. I couldn’t believe it. Things just keep going from bad to worse. If he calls her, she’ll probably go along with my sucking him off every day. She’d do that just to prove her power over me.
After a few minutes I headed up the path, but waited until I figured she should show up. Finally I walked out and stood next to the curb. Luckily she came along within a couple of minutes.
“How come your knees are dirty, slave?” she asked with an amusing grin.
“You wouldn’t believe it if I told you.”
“Try me.”
“I sat over there on that bench, and a guy pulled up in a big, black Mercedes. He wandered over and propositioned me. He said if I didn’t give him a blow job, he’d call the cops and have me arrested for solicitation. I figured I had no choice.”
She laughed. “You mean I could pimp you out and make some extra money?”
“Do you need any extra? You get your paycheck as well as mine.”
“You don’t get one anymore, remember?”
“Yea.”
“But, you’re right, I don’t need the money, but it would be fun making you do it.”
“That’s what I thought you’d say, when he asked for your name and number. He suggested that I could meet him every day for a blow job and training.”
“He actually asked for my name and number? You’re kidding, right?”
“No, and I had to give it to him, or he was going to call 911. Please don’t make me do it, Mistress.”
She just smiled, as she drove on home.
On Monday the contractors arrived and started working. They emptied the cellar where the dungeon was going and started sound proofing the entire room. I didn’t bother them. After all I had my own work to do.
That afternoon I was doing my housework, when the doorbell rang. I looked at the clock and realized it was 1:30. A feeling of panic rushed through me as I opened the door.
It was him.
“Margo said you would be here naked and waiting,” he laughed, as he looked down at my caged cock. “I guess you can’t show me how excited you are to see me, can you?”
He reached down and grabbed the stainless steel cage, twisting it around while looking at it.
“Can this thing come off?”
“No, Sir,”
“How long have you been in chastity?”
“Going on three months.”
“How long is she leaving you locked up?”
“Forever.”
“You like it?”
“I have no choice. I am her slave. She owns me.”
“Interesting?”
“Well, slave. You know why I’m here. Why don’t we go upstairs where we can get comfortable and have a little fun?”
“I guess I have no choice, do I?”
He just laughed.
Before long he was naked and standing beside the bed. I was on my knees with his cock deep in my throat. He made me suck on his balls before sucking him off. But, just like the last time, I was told to always look him in his eyes as I serviced his hard cock. It took several minutes before his cum blasted down my throat.
“Go get me a glass of wine, boi. We aren’t through yet.”
When I returned, he had me get him hard once more. He leaned me over the end of the bed and slid his cock up my ass. It hurt after last night with Lilly.
“By the looks of those puffy, red cunt lips, someone has been having a lot of fun with you.”
“Trust me…. It hasn’t been that much fun, Sir.”
He laughed, as he continued to fuck me. Finally when he was really close to blowing, I had to finish him with my mouth, again swallowing his precious spunk.
Finally he got dressed and started out the door. But he turned, “I’ll be back tomorrow, same time. Be ready, understand?”
“Yes, Sir,” I responded in despair.
“I want you kneeling by the door waiting for me with a smile on your face.”
“Yes, Sir.”
Things didn’t change very much for the rest of the week. He arrived every day and used me over and over for his pleasure. On Friday, he made a comment that made me cringe, “You’ll do. I’ll talk to Margo. See you again on Monday.”
My Mistress came home early, so she could meet with the contractors. They were making good headway on the dungeon. The concrete walls were covered with rocks that looked like a real castle’s dungeon. There was actually an ominous feeling about the whole place. With several pieces of medieval looking torture devices placed around the room and a small cell in the corner, I realized that things were getting even more serious. Margo was pleased. The men thought they would be done by the middle of next week.
After looking over the new equipment, she secured my head and arms in the pillory and left, locking the door behind her. It was totally dark, as I stood there unable to move. There, with my wrists locked on either side of my head, I waited. There was no escape as usual. Heavy hardwood timbers held me as the hours slowly passed. Later in the night she came home with one of her boyfriends and released me. My entire body was stiff from being held in that position for so long, but it didn’t matter to them. I was allowed to sleep in the spare bedroom while they made love next door. Margo didn’t even have me service her when they were done.
My Mistress let the twins use me again on Tuesday night. Obviously she told them about my experience with Lilly. While I tongue fucked Julie to some extraordinary new heights, Jackie whipped my ass. She viciously beat me with a new short three pronged quirt. The foot long fingers were made of twisted, braided leather that bit cruelly into my ass flesh. Later, as I serviced Jackie, I was fucked with a huge ribbed and bump covered strap-on. It felt like it was rubbing my already stretched and swollen ass lips raw.
But they were not done. I was tied over the foot of the bed with my legs stretched wide and my hands cuffed behind my back. Then I heard the distinct sound of a rubber glove. Instantly I panicked. I knew what was going to happen next.
“No, please don’t.”
Julie just laughed, as she started to grease up my hole.
Then I felt her fingers pushing and prying their way into me. I buried my head in the mattress and moaned in pain. She was relentless in her efforts to hurt me, pushing and twisting her knuckles against my hole. After a couple of minutes, her hand was inside me, going ever deeper. She closed up her fist and started in, fucking me as hard and as deep as she could. When I thought I could take no more, she yanked her hand out. I thought it was over, but she had other ideas, ramming her fist in and out of me several more times.
I remain tied there while they picked up their mess. When I thought they would release me, she pushed the strap-on she had used into my ass. With a piece of rope tied around my waist she took it down over the dildo between my legs and tied it to my cock cage, pulling it extra tight. It not only pulled my cock and balls painfully back between my legs, but it kept the dong from coming out.
“We’re going now,” she said. “Thanks for all the fun. Margo can untie you when she gets home. Enjoy yourself, and we’ll see you next week.”
“P – l – e – a – s – e,” I begged, but the lights went out, and the door was closed.
I lay there in absolute agony and heard their car drive away. I was helpless in the darkness and realize my life was in a con
tinual downward spiral, and there was no way of stopping it. It was like an airplane that stalls and heads towards the ground in ever tightening circles. You can’t pull it out. It will crash. I realized that I created this. For years I dreamed of being exactly what I am today – just a worthless slave, to be used and abused in the most depraved and painful ways possible. And the truth be known, when my immediate pain is gone, I’ll probably want it again and again and again. It’s a sickness I can’t shake. It’s like a drug. I can’t stop it.
As the hours passed, I seem to go in and out of consciousness. I wondered if I have started to find that secret room within my brain. Then something snapped me back to reality. My Mistress was home.
She turned on the light and laughed. “Were the girls a little rough on you tonight, slave?”
“A little, but it’s okay. I’ll survive.”
“Julie texted me and told me all the gruesome details. Do you want me to release you? We’re going to be a while.”
“Please… take that monster from my ass and untie my legs. You can leave me cuffed until later if you’d like.”
“There,” she said, as the ropes were removed. “I’ll let you know if I need you.”
“Thank you, Mistress.”
She left, and I lay on the bed, listening to them make passionate love. Her softened screams of joy and his moans of passion passed through the thin, hollow wall between the two rooms. My cock tried to get hard, but the cage was too small. As it fought its tight steel-barred confines, hoping to get erect and spit out its juice, I smiled. Being caged and cuckold had been a long time fantasy. I just never realized how much I would miss that pleasure. But that’s long behind me. They say that there’s no going back. Deep down, I really don’t know that I wanted to.
After several noisy orgasms, she came to me. “Bring me one more time,” she whispered. I rolled over on my back, and she put her pussy to my lips. It didn’t take long. I licked and sucked everything she had to offer after spending the night with him.
When she climbed off, I noticed that he was standing in the doorway watching. He was naked. His cock was partially erect. I wasn’t sure if it was from watching us, or he wanted something more.
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