As the cocksucker carried himself up the steps to the apartment he knew this day was going to be different. He hated that he was already referring to himself a "cocksucker". It made him feel less than a man, but I guess that was the whole idea. After today he would have a whole new label to describe himself. He felt scared.
Having spent the past several days and the whole morning preparing himself for what was behind the door of apartment 8b. He waited for the door to open.
"Come in your early cocksucker, that's okay I like your eagerness". His new master said.
I had always Called him sir, but lately he preferred master. His given name was John, but his friends called him Jack. I didn't rate as a friend even though I probably spent more time, especially between his legs, than those that had the privilege of knowing him outside of his apartment.
"Don't get to comfortable, that's not why your here today" he said with a slight callousness in his voice. " I have to finish up some work. Put some pillows down near the sliding window, I'll be with you shortly".
" may I use the restroom master". I replied
" sure but don't mess it up. I just cleaned in there" he replied
I made my way down the hall passing his bedroom. I hadn't been allowed in their yet, but was hoping today would be different. I noticed the bed was made.
In the bathroom I pulled down my pants and reached back to remove an anal didoe I had been sitting on in the car in the way over. It was several miles to apartment 8b through city streets so the black plug had shifted and pushed several times causing my pens into leak onto my underwear. I removed it and put some additional lube from my pocket onto my anus. You see today I was going to lose my anal virginity. It was a long time coming. I had already been sucking cock and swallowing countless loads of cum for about 7 years. It just felt like the right time. I just wasn't getting type of thrill from oral domination I used to get. It was definitely time to move forward.
I sat by the window on a pillow naked now waiting for direction. I was completely sober and not intoxicated. Jack wanted me to fully experience what was about to happen. He came into the room about 15 minutes later. I was a mess thinking about what I was there for. I even contemplated running for my life, but that would have consequences and I didn't want to even think about that.
"I'm not going to ask you if your ready. You being here naked near my balcony window tells me that, and beside the time for decisions is over. I make the decisions concerning you now. Isn't that right cocksucker?" Jack was looking me square in the face.
"Yes sir, but wouldn't the bed be more comfortable for both do us". I replied hoping I didn't upset him.
He just shook his head. Cocksucker, cocksucker, I think
it's better and most definitely more humiliating if you take your first cock up your cute asshole where all the world, especially my nosy neighbors across the way. Anyway I'm filming the entire experience and the light is better here don't you think" at that he fully opened the blinds. The sunlight was bright and blinding.
" yes sir, how do you want me". I nervously replied.
" on your back like a women, because in 10 minutes you will no longer be fully a man anymore" he laughed as he undressed.
Jack was already hard and he kneeled down on a large pillow. He adjusted one of two cameras to show just my anus the other to show my face and body reaction.
"Lift your legs and spread them wide".
I did as he asked as he moved between my spread legs
" now reach down here and place my cock at your stretched opening. I see you've lubed already, and I hope you used that home enema kitt I sent you"
" yes sir I'm clean. It was
he'll doing hiding that with my wife around"
I reached down like he asked and placed the tip against my new pussy as he like to call it.
" now I want you to concentrate and relax, this may hurt a bit, but that really doesn't matter now because it's going to happen one way or the other cocksucker"
" y-yes s-sir I replied". I felt like I was in an an alternate universe.
That thought ended abruptly as jack roughly pushed forward using his right hand to fix the shaft in place.
"Omg that hurts" I cried " please stop and I involuntarily tried to push him off me
Big mistake as he took his back of his left hand and firmly smacked my face.
I started to cry, as much from the cock entering my body for the first time, and the pain and shock from the smack that got my attention. I began to do a sissy whimper. He always enjoyed hearing my submissive sissy noises.
" he the firmly smacked my buttock and told me " this is going to
happen and is happening so just accept it"
"I bit my lip and mumbled out a "yes sir" as he drove another inch forward. I started crying and shaking my head back and forth not believing I was voluntarily allowing this to happen to me. Didn't this just happen only to faggot stand prisoners?
Jack stopped and allowed my anus to stop spasming on his shaft. We stayed that way for over a minute. Him hovering over me, smiling at his latest conquest. Glad to have convinced me that I needed this to feel like a complete cocksucker.
He drove forward and finally settled balls deep in my ass. Our thighs touching. It hurt quite a bit, but there was a strange satisfaction spreading throughout me for being able to endure this assault.
We stayed that wispy for a full minute and just before he withdrew a couple of inches, he leaned forward between my spread legs and whispered " the first of many, the first of many cocksucker"
I looked up at his smiling conquest filled face and slowly pushed back to meet his thrust. We began fucking as I ignored the pain. It was soon replaced with a warm feeling of satisfaction that I had passed this test and would now be something else other than a man.
We continued to fuck p, him turning me over on my stomach and really hammering his lust away at his new pussy.
He whispered again " you have lots of work to do to make this hole as well trained as your mouth"
I just nodded and kept saying " yes sir, yes sir". Each time I said it I felt my manhood slowly fall away.
He finished and reached his peak while fucking me on my side, we were bareback. I knew it was a risk, but I truly felt that I should feel his cum leaking from my stretched hole. He agreed beforehand. We stayed that way for awhile his softening cock finally slipping from my abused hole.
I'm going to take a shower cocksucker, clean up my place and don't leave until I'm done. I think I'm through with you today"
I hardly heard him as I tried to close my wide open pussy hole. I did feel the cum start to drip out. I had placed some Kleenex nearby and reached back and wiped. I didn't want to be punished for dripping on his pillows or floor. I did taste a little of his cum.
I got up and started to get dressed even though he didn't tell me expressly to do that.
He got out of the shower and I crawled over and while looking up licked and nuzzled his nut sack. He reached down and smiled pulling my head tighter into his crotch.
" be here tomorrow at 1. We can begin you advanced training then, this was just a test of your dedication. You passed cocksucker. I'm proud of you".
I didn't say anything, but got up after giving his cockhead a parting French kiss. I left apartment 8b a new person. Not quite the man I was just an hour or so ago, but not yet a women.
By Steven889