Chapter Five
I’m not sure how long I sat unable to close my legs but if felt like days. Eventually the quivering from my orgasm stopped but I was still unable to prevent the tears flowing from my eyes. My vagina began to feel cold as my juices evaporated.
Though the logical part of my brain knew that the sooner Jim came into the room the sooner things would be over, when I heard footsteps approaching from the outer room my heart began pounding as though it were about to burst free from my chest. With every beat I could feel my breasts shake and the weights pulled a little more. The door opened and the most handsome man I have ever seen walked into the room. Six foot one inch with pecs and abs I could see through his skin-tight white t-shirt. Shoulders wide enough to block out the sun. Thick wavy dark brown hair and eyes as blue as the sky.
“Well what do we have here?” he asked. “What is your name?”
“My name is Please Rape My Pussy.”
“Nice name. It suits you. You see I will be rapping your pussy in few minutes. But first I want to ask you a few questions. Tell me, what happens when you refuse to obey an order here?”
“I am punished.”
“Correct. And what happens if you withhold information?”
“I am punished.”
“Correct again. Tell me, have you been punished yet?”
“Yes.”
“Why were you punished?”
Choking on my words, I answered, “First … I was punished because I did not tell the men my correct name. Next I was punished because I did not do a good job when I was told to describe my vagina. Last I was punished because when I strapped myself into this chair I was still able to move my vagina slightly.”
“Good. From what I have been told by my friends those are the correct answers. Did you enjoy being punished?”
“No, I didn’t.”
“Good. Tell me, if you need to be punished again, what do you think that punishment will be?”
“I think … my clitoris … I mean … I think you will pierce my clitoris if I need to be punished again …. But, I swear, you won’t need to punish me. I will be good. I will do anything you tell me to do. I promise. I will be your slave.”
“Good. Now, keeping that thought in mind I want you to listen very carefully to what I am about to say … I want to do something to you that you have never let any man do before. You have been waiting for the right man to do it with. It seems to be something that scares you while at the same time excites you.”
Jim continued speaking calmly, “Because I am trying to humiliate you and degrade you as much as possible I want you to tell me to do that something to you. Remember, we have been watching you for a very long time. You do not realize it but we have been into your apartment, and gone into your bedroom, while you were at work. We know very personal information about you. Tell me now to do that something or you will be punished. Be sure to say please.”
I realized with a shock what Jim was telling me. These men had been into my apartment. They had been into my bedroom. They had certainly seen the diary on my bedside table, the diary where I had recorded my most private feelings. I knew exactly what he wanted me to say. Though I knew it was going to happen, being forced to tell him to do it made is so much worse.
Sobbing more than ever I said, “Please … put your penis in my vagina. Do not use a condom. Please … Please cum … cum inside my vagina.”
“Good,” said Jim. “That is what I wanted to hear. I can see you have learned your lessons. So, it is true? You have never let a man cum in your cunt before?”
“No … I was … I wanted … it scares me.”
“Hmm … well I’m going to cum in you. You are completely vulnerable, correct?” Jim asked as he kicked of his shoes and undid his belt. “Can you move your pussy at all?”
“No, I can’t move …. My … my pussy is completely vulnerable.”
I shut my eyes as Jim began to remove his boxers. I intended to keep them shut for the duration of my rape but when I felt something brush against my opening I couldn’t stop myself and I looked down between my legs. The very tip of Jim’s penis was just touching my vagina. His friends had not been exaggerating about his size in the slightest. It was probably eight inches long.Even worse, it was a thick as my wrist.
“NO! Please don’t!” I screamed. “Don’t put it in! It is too big! Please, no! Ah … aaarrghhh! Oh, no please go slower! It’s hurting me!”
“Well … I’m only in about an inch,” said Jim calmly. “You know I am going to put it all the way in right? You know you can’t stop it from happening right?”
“Yes, I know it is going to go all the way in,” I cried. “But … it is hurting me! Please go slowly!”
“I’ll tell you what … I’m in a good mood. I’ll promise to go slow if you do something for me.”
“Anything! I’ll do anything you want!”
“Squeeze my cock with your cunt. I want you to contract the muscles in your pussy to squeeze me. Squeeze and hold for two seconds and release. Repeat again and again. Each time you release I’ll push in a tiny bit more. Once I am all the way in you will continue until I cum. But if you stop at any point I’ll ram it in all the way as hard as I can. Do you understand?”
“Yes! Yes … I … I’ll do it.”
“Well then, get started!”
I couldn’t believe what I was doing. I never thought that anybody would tell me to use these muscles like this. I squeezed and held and felt my vagina wrap tighter around Jim’s penis. When I released I felt his penis slide inside painfully by a sixteenth of an inch. With each push I felt myself being stretchedand violated even more. I didn’t dare stop though. I knew that if I did the shock from Jim’s sudden thrust would kill me. A fraction of an inch at a time and I might actually be able to handle it.
After what seemed like forever Jim said, “You’re doing very well. About one more inch. I’m getting closer to cumming too. How does that make you feel? Knowing your cunt will soon be full of my semen and you can’t do anything to stop it?”
Doing my best to speak without disrupting the rhythm of my squeezing I said, “It makes me … disgusted … I … I don’t really want… please don’t cum in my vagina. Please, please pull out!”
“Please Rape My Pussy …” said Jim.
“Yes?”
“It is too late.”
Suddenly, there was a warm sticky explosion deep inside my vagina. It was unlike anything I had ever experienced before. I felt Jim’s semen land on my cervix and fill me up.
“Nooooo!!!!” I wailed.
“Good job,” said Jim as he slowly removed his penis from my aching vagina. I could feel his semen dripping from my most private part.
“Was there … did you … how much cum is there in me?” I asked through my tears though I already knew the answer.
“Hmm …” said Jim. “That is the first time anybody has ever asked me that. Lots I think. I came really hard. You see, you really are very tight and that always feels better. Also, you did such a wonderful job squeezing that I think you pulled more out of me than usual.”
He stooped down and picked up his pants. As he put them back on he continued talking.    “Your rape is over. Well, your first rape is over at any rate. I really enjoyed it. Now you get a bit of a rest for doing such a good job.”
He removed a pocket watch from his pants and placed it on my stomach. “It is now eleven fifteen at night. My friends asked to tell you that you are needed tomorrow at noon exactly.”
“Am I going to be raped again?” I asked tearfully.
“I am not sure,” said Jim as buckled his pants. “It depends on what sort of mood the rest of the guys are in. You may simply be required to help with another rape. On the other hand, you may be in for a gang bang. The possibilities are endless really. Regardless, tonight you may do whatever you want within these rooms. We have even left a little food for you in the bedroom. Your only instruction for tonight is not to remove your new jewelry. In the morning a letter will be slipped under the door for you. You should read this letter carefully as it will describe for you exactly how you should prepare yourself.”
He stood up and removed a key from his pocket. He released my hands from the cuffs and walked out of the room as his semen continued to drip from my vagina.