Entering and Breaking

"Mister, you really need to relax because you are going to take this penis down your throat, understand?" He looked down at me and I was looking at him as commanded.

"Yeh hir." I was weak and he was right, I was his bitch.

With that small amount of submission he was back working my throat. He was training me. The cock would press into my throat and then pull out. I gagged and coughed and drooled all over the thick member a number of times and I was trying hard to relax but who the fuck can relax when they are getting raped by a monster and a bowling pin. Despite my obvious agony he kept jamming the thing into my mouth. He wasn't going deeper, just continually holding it back there longer. Unbelievably, I was beginning to lose the urge to gag and was timing the penetrations with large gulps of air.

The pressure against my anus was unrelenting. How long was this going to go on? My sphincter gave a little more but the pin was not in yet.

"How's he doing over there Ma'am?"

"I don't think he's going to be able to take this. I'm going to hurt him."

He laughed. "Oh, trust me Ma'am, he will be able to take it just keep that pressure on."

"Yes sir." She meekly replied.

Hanging on to my hair with one hand he continued to fuck my mouth and reached underneath me a grabbed my nipple hard and twisted it. He kept teasing me this way and to my astonishment my poor caged cock began to strain painfully against it's confines. It was all too much and I felt like I was going to pass out from the shear agony of the evening. The cock in my mouth was now attempting further exploration of my throat and I struggled to keep my gag down. With every new thrust, the fleshy meat in my mouth was going deeper but he didn't hold it there long. That was helping with my gag reflex. A little at a time.

The bowling pin pressed further into my reluctant yet accepting ass. I felt more of it stretch me further and I wanted to scream but all I could do was cry. The man switched hands and tweaked hard on my other nipple. The dick pressed into my throat. If my mouth were able to function like a mouth you would have heard my scream OH MY GOD at the top of my lungs. My ass had taken the last of the girth and the pin slid easily into my ass. And I fucking came! I fucking came despite the restraints on my dick and the betraying orgasm was harder and longer than any I had ever had. What the fuck?! I was shuddering in painful ecstasy, completely ashamed and humiliated.

"Wow! Ma'am, I did your husband just ejaculate on the floor?" He withdrew himself and rested while I caught my breath.

"Oh my god, he did...he took it and came." Was that amazement or disappointment? What a bitch.

"I told you your husband was a sissy. It looked like quite the orgasm. Imagine that, his little penis caged and all. A man who can ejaculate through penetration, well, that's no man at all. More of a woman, but not quite. A sissy. Don't you agree Ma'am?"

"Yes sir." I think she did.

"Why don't you let that bowling pin hang there and scoop up that sperm and feed it to him." He withdrew his dick from my opening.

"Yes sir." At last she sounded reluctant.

Gently, she released the pin and there it hung, gravity pulling it down putting pressure on my insides. She was doing it. She was going to feed me my own cum. She was now standing in front of me. I was commanded to look at her in the eyes. It was so hard to hold that gaze. What was she thinking? I couldn't read her now, I felt like I didn't even know her. She stuck her fingers in my mouth and I was told to lick her fingers, to clean them thoroughly. I did and my own cum was on my taste buds. I lapped at her fingers as she wiggled them around so I could get all of the cum she had saved from the floor. My cum. When she withdrew she was told to return to her position and begin fucking me with the bowling pin but to not take it out until she was told. Back in position, the cock in my mouth now thrust frantically at my throat.

"Guhg...gg.ggurg...gug..g..gulg...guh..guh..."

The sound of my throat being fucked must have been music to the sadist's ear. My ass was being stretched and unstretched by my wife's own doing. The smaller shaft of the pin didn't feel like anything compared to the huge head it had and what went in must come out. I was dreading it. In my mouth, the cock had slowed and I was once again being prepped for the inevitable deepthroat he meant for me to perform. He was patient and methodical and I could tell he had trained many. My sore throat was becoming more accepting of the cock. Further it reached and he complimented every new depth I attained. I took a deep breath as the dick came at me once again and this time he pressed hard into me. My throat was opening for him and he was nearly there. It wasn't his goal this time though. In my throat he gave six or seven little thrust, he was literally throat fucking me. His pleasure was audibly confirmed with low grunting and growling. He pulled out and I gasped for air and only gagged a little. Another deep breath and he was at it again. His hardness reached my throat and kept coming. A huge cock was lodged in my throat and I was squirming in desperation. Then his balls hit my chin. I could no longer see him but I know he was looking at me with a grin and a hint of pride.

"Now that's nice. Ma'am come around here again and watch your pathetic sissy husband take this penis all the way down his throat." He pulled out entirely and let me breath and choke.

My wife once again left the pin hanging and came around. I was looking at her but she was watching the dick re-enter my mouth. Her eyes grew wide as my nose filled with pubic hair and his clean shaven balls once again rested on my chin.

"It feels so good. Maybe better than a vagina or virgin ass. Ma'am, do you think you could take a penis like mine all the way into your throat?"

"No sir." She wouldn't look at me. That bitch wouldn't look at me. It was true. She would rarely even give a blowjob to me. I wanted him to make her take his dick so bad.

"Well, I imagine that this sissy here always wanted a deepthroat she just didn't know she was going to be the one to give it."

I was completely out of air and just as I thought I may faint he took the cock from my throat and allowed me some air. My wife was instructed to continue her assault on my anus and to withdraw the pin when she was instructed. My mouth once again became a dick receptacle and he was fucking me once again with all out abandon. I gurgled on my own spit as the raping proceeded. Once again I sensed he was building to a climax and as he grunted the cock pushed into the back of my throat one final time."

"Pull out, pull it out!" He was yelling at my wife and my ass stretched just as painfully as before trying to clutch on tightly, not wanting to give up the object.

"FUCK YEA! FUCK YEA! EAT MY SPERM SISSY!"

He was laughing as his cock bulged and spewed a fat load of cum into my throat. I could feel it's warmth as it coated my esophagus. He was pulling out as another load hit my throat. As he came, the bowling pin stretched me open wide and I shuddered through yet another orgasm. I was cumming hard just as the man in front of me unloaded a stream of cum on my face. I yelled as the pin popped out of me and more cum fell on the floor below me. Holy shit he had so much cum. Two more loads were dumped on my face. He was dripping with sweat as he held onto my hair..

"Look at what a little sissy sperm dump you've become. And you came again!" He was smiling as he rose to his feet. "Ma'am, take a picture of your sissy husband's face."

My wife left the room and came back quickly with her phone. I looked at her and she snapped multiple pictures of my destroyed face. When she finished she was instructed to send them to him and he gave her his phone number. She complied and was then told to remove the gag from my mouth and to clean the cum on my face and feed it too me. She did as she was expected to do. The gag was removed and my poor jaw ached. I was speechless and broken as I sucked the cum from her fingers and swallowed every bit of the cum that she fed me. When she finished he let go of my head and I once again collapsed to the couch but not for long. He pulled on my arm binding and roughly swung me around. He pushed me to my knees and holding onto my arms pushed my face close to the floor.

"A good sissy cleans up after herself, right sissy?"

"Yes sir." I croaked through my sore throat and began licking up my cum from the hardwood. How could I have cum so much and two times?

When I finished eating my own cum I raised my broken body and looked up into the lens of a video camera. The rapist held it in his hands now and was filming me.

"Can you state your name and what you are?"

I didn't even hesitate, this had to be close to the end. "My name is John Morris and I am a sissy Sir."

"Where do you live Mr. Morris?"

"I live at 435 Sunny Drive Sir."

"How many times did you orgasm tonight?"

Jesus. "I orgasmed twice sir."

"You came two times even in your pathetic caged penis? Why?"

"Yes Sir, because I am a sissy." I lowered my head. He chuckled to himself and turned off the camera.

My wife was instructed to release me from my arm restraints. She struggled with them for awhile and I could hear my captor gathering his things and dressing himself. It was over and I was raped into submission but alive. I finally felt the my arms becoming free. My shoulders ached and I had no feeling in them and they collapsed beside me. I rolled onto my side into a fetal position on the floor and began sobbing uncontrollably. My ass was full of cum and pain. My jaw and throat were so sore and my mouth tasted of semen. How could I have let this happen to me? My wife sat next to me but did nothing to comfort me. I hated her so much right then but I couldn't move and I could not stop sobbing. I stared blankly at the bowling pin lying on the floor.

"Well, you have been great test subjects I must say and we are all getting out of this ordeal knowing a little bit more about ourselves."

His words flowed into my ears as he stood towering over us completely dressed and packed. He was leaving. "As promised, I am going to leave you a stipend. One thousand dollars right here in this envelope." A heavy envelope was tossed onto the countertop. He picked up the gag and arm binders off the floor. "Now, I'm taking these but you can keep the chastity cage. Consider it a gift from me. She obviously has no problem having an orgasm in that thing so I see no need to take it off. I do expect some of your participation money to buy a new gag and some more appropriate female clothing for this sissy. Ma'am?"

My wife looked up and he motioned for her to stand up and come closer. She moved in close and he was handing her something.

"I am going to make you your sissy's Keyholder. As a keyholder, you will wear it around your neck at all times and never allow the sissy to have it in her possession. I am expecting you Ma'am to send me a picture of that caged penis within two minutes of me asking for it. If she is not with you she will have to send it to you and then you will send it to me. If you fail to do this within the allotted time I will make this video available to anyone you know. Understand?"

"Yes Sir." She seemed calm and compliant while she took the key. It was on a silver chain and she put it around her neck. The brass key hung on her chest dipping into her cleavage. He stepped closer to her and they never lost eye contact.

"You will remove the cage tomorrow and let the sissy shave herself properly. All good sissies should be completely hairless, their whole bodies. Immediately after showering and shaving you will send me a picture before you put the cage back on and another right after. At no time should you think of taking it off unless you have been instructed by me or there will be consequences, understand? I would hate to see this video get emailed to all of your family, friends and co-workers. Do you know what I am saying?"

He took another step closer and she looked up at him. "Yes Sir."

His hand reached out between her legs and a smile broke out on his face. She never flinched and i saw her body quiver. She stared at him and moaned. He worked his hand between her legs and soon she was panting like a dog.

"Ohhhhhh...my...GAAHHHD!" She was cumming into his hand. She reached out and held onto him screaming in ecstasy. He pulled her in close with his other arm and while she finished her orgasm he pressed his lips against hers and kissed her deep. She moaned deep and returned the rough kiss. He pulled away and I could see his teeth held her tongue and pulled it from her mouth. When he let go, she collapsed against the counter and then fell to her knees. He put his pussy soaked fingers in her mouth and she sucked her own juices from them. He walked away without another word and left the house. I closed my eyes and laid there shivering for a long time. I had no idea, even then, how much my life had changed and was going to change.

Somewhere, in a far room, my wife's phone text tone chimed.