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Introduction:

My first anal experience

I was ashamed and confused by what happened the night before. While I was definitely forced into sucking Paul off I can’t say that I didn’t enjoy it a little bit. My body betrayed me most. While I was sucking him off I had a rock hard erection and when I got home, discovered precum all over the inside of my underwear. All this, coupled with the threat of exposing my incident to my family, brought me back the following evening.

This time, as soon as I stepped in the door, Paul walked over, locked the door and led me to the back room. I had been expecting to be required to suck him off again. Unfortunately for me, Paul had other plans entirely. “You are going to learn how to be submissive” he said. It was then I noticed the desk.

Where the computer had been now sat a clear desk with two ropes tied to either end and two shorter ropes around the legs of the desk. “Strip down to your underwear and face the desk.” Obediently, I removed my clothing and faced the desk, shivering with anticipation as much as the cold. “Your nipples are hard” he said as he grabbed and forcefully twisted before using them to force me down face first into the desk. “Paul please. We need to stop this. I will pay you” I pleaded as he tied my first outstretched arm to a corner.
“We are way past that. And don’t act like you don’t enjoy this. I can see your hard cock from here” he stated, as he proceeded to tie my other outstretched arm and legs in a spread eagle position.

As he walked around behind me, fear about what was about to happen set in. “Please Paul, I will do anything. Just please can we stop this?”
I heard moving behind me as Paul walked closer and pushed his pelvis up against my boxers, his hard member already pressing against me. Without a word he reached forward and placed a blindfold over my eyes and, before I could began pleading again, a ball gag in my mouth.
“Now you are going to learn that I am your master and you will do what I say.”

Looking back on it, it truly opened me up to the lifestyle I have now and raised my horizons. Had it not been for Paul, I imagine I would still be having boring sex and not be the open minded individual I am today. I remember the event fondly today, however, at the time it was nothing but fear and pain.

Paul began by cutting my boxers off of me with scissors, ‘Stay still or you are going to get hurt.” Being unable to see or protest was one of the scariest events of my life. As I lay there bent across the table with my hands and legs bound, the uncertainty of what was about to happen made my body start to shake.
*SLAP*
My ass cheek jiggled and stung where his belt made contact. My muffled scream filled the room. “That is for being such a difficult whore.”
*SLAP*
“That is for not taking my dick in your mouth when I told you to the first time.”
*SLAP*
“That is for not showing me your dick the first time I asked.”
*SLAP*
“Or the second”
*SLAP*
“Or the third.”

By the time he was done my ass had welts on it that would make sitting difficult for weeks to come. I lay there defeated, tears running down my face, unable to protest or ask anyone for help.
“Now that your ass is tenderized, it is time to try out the meat.”
The sound of a rubber glove snapping onto his hand followed by lube being squeezed out of a tube sent a new wave of fear across me. “If you tense up, it is going to hurt even more” Paul told me as he inserted his pointed finger slowly in my ass.

I have since tried to recreate the feeling of being unwillingly bound and anally violated in role play without much success. The initial fear and humiliation of having someone you once trusted forcefully enter you against your will is a feeling that I have longed for every day since. This was not the case at the time, but we never appreciate things until after.

At the time, all I could do was try and ease the pain as he shoved the first finger in slowly, deliberately. I felt the tip of his finger enter first, slowly penetrating me to the first joint, then the second. Once he bottomed out he began pulling it back out slowly. Again and again and again he did this, so slowly it was almost a tease. I could feel my precum oozing out of my penis as he continued loosening me up for his pleasure.
“You are much looser than I would have thought” he said “I think you need more.”

With all ease and concern gone he thrust two fingers in my ass and began violently twisting back and forth. I screamed against my ball gag in pain. My asshole felt like it was going to tear in half. My body writhing in pain as he placed his other hand on the small of my back and held me down. No one could hear me. No one could help me.

After what seemed like hours he pulled his fingers out and pulled off the glove. I lay defeated, my ass still stinging from the welts now added with the soreness of my asshole. “A rest” he said.

I knew what was coming.
From the moment he began tying me down to the table I knew my night would end this way. The knowledge did nothing to lessen the pain or the humiliation I felt.

“Keep breathing and it won’t hurt as badly.”
As the tip of his rock hard cock bumped against my asshole I let out a muffled plea to stop. This was met with a ear splitting crack across my already raw ass cheeks. I knew it was hopeless, and so I did not try again.
“Breathe” he said as he began to apply pressure. All the work he had done with his fingers did not prepare me for the sheer size of his cock. Pressure, pressure, and more pressure. Just as I thought my ass was going to tear I felt the tip slide in. “There we go” he said with a moan.

Slowly and deliberately he began to slide in my ass, inch my inch. As I felt my ass stretch out over his rock hard dick my legs began to shake with a mixture of intense pain and pleasure. Tears filled my eyes as I was almost unable to bear the pain, but unwilling to do anything about it. For what seemed like hours he slid every inch of his dick into my ass until I felt his ball resting against mine.
“My little slut took the whole thing in one try.”
I moaned in acknowledgement.

Slowly, deliberately, he began to ease back out of my ass. A new wave of pain hit me that had been lessened while he was completely in me, filling me up.
In and out, in and out, his thrusts becoming more vigorous as my pain became more intense. At times he would thrust into me so hard I could feel him bottom out, smacking his balls up against mine as he pulled at my hips with his hands. Other times he would be slow and methodical, making me feel every inch of him as he pulled in and out, his hands caressing my balls and cock.

This went on for minutes, or hours. All that existed in those moments of hell was my ass and his cock. After initially fighting against my restraints, I now used them to brace myself and take his thrusts. My initial muffled shouts of pain slowly became moans. Although I was still in agony, my body was betraying me and enjoying it to some extent.

“Are you ready for my seed?” he asked. “MMMMM” I said, expecting him to put it in my mouth again.
With three giant thrusts he placed himself deeper than he ever had in my ass, mashing me into the desk and making me scream out in pain. As he moaned I could feel his cock pulsing, filling my ass with his hot, sticky load. Pulsing again and again he released what seemed like gallons of cum into me as he held my hips. After he had released his seed into me, he bent over and said into my ear “You are my slut now. No one else’s” and slid his cock out of my ass.

After he pulled out of me he left be tied to the desk as he cleaned himself up. As cum slowly oozed out of my ass and down my legs I heard him come up behind me and take a photograph with his camera. “Extra precaution and a momento of your first time” he told me, and then began to untie my ropes.

“You are still hard, we can’t have that” Paul said after he had untied my ropes and removed the mask and gag. “Get on your back and raise your legs above you head.
Defeated, I did as I was told, cum dripping down my legs. Paul then pulled my legs back further until my ass was off the ground and I was resting on my shoulders. As my erect cock stared me in the face directly above me, I understood what he was about to do.

“Open your mouth and stick out your tongue.”

It only took a few strokes to finish me off. I still remember the salty bitter taste of my own cum as it filled my mouth, the excess spilling over my lips and cheeks.
“Now swallow like a good whore.”I did as I was told, ashamed and humiliated.
He then took his finger and wiped up what remained on my face, having me suck it off his finger.

“Now get your clothes on and be here at the same time tomorrow.

I obeyed.

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