Free Spirited (09)…My first job (New Years Day 1999)
Introduction:
It was 1998, I was 16 years old living in a dump of place with hookers, junkies and street kids; it seemed a hopeless situation. An opportunity arose for me to work and leave this place.
“Remember if you fail; you will be my bitch forever”
Those were the parting words from Tex; I was not sure what they meant, but it made me feel uneasy to say the least. Now I was more determined than ever to leave; and become independent at the brothel. My one and only regret about leaving was having to say goodbye to Stacey. I was hugging her with moist eyes when the car arrived for me.
A burly driver was my tour guide as he drove me through the back streets in a town called St: Kilda. We arrived at what was once a warehouse; but recent renovation now made it look like a restaurant.
“Take your clothes off and wait here” were my orders as soon as I entered reception.
It had a very impressive interior; the long red curtains draping the windows matched the warm plush purple carpet. The creative decor made my clothes seem like a bunch of rags. There was a girl attending the old styled reception desk trying not to blatantly watch me as I undressed.
Soon I was standing there holding my clothes trying to cover up a little of my nakedness. Then when the receptionist took them from my hand I was fully exposed, feeling embarrassed and very nervous. It seemed an eternity before she returned and gave me some information and instructions.
“I am going to blind fold you for security reasons; then take you to a room to talk to someone”.
I was led down a flight of stairs; before taking a short walk into the room where my blindfold was removed. When my eyes adjusted to the light I discovered I was in a large basement with cubicles similar to a restaurant, but beds had replaced the tables. The couple who I had met at Tex’s place were there to greet me.
“Hello again” the women said.
In my naked shame and embarrassment all I could manage was a nod.
“This area is set out for all our trainee girls; your bed is over there”.
As I looked around the room I saw a bottled drink dispenser directly under a large light; there were no windows.
The man then addressed me “Turn around and you will see there are some gentlemen standing behind you”. There were four “bouncer” muscled men; I nodded my recognition to him.
“These people are going to prepare you in readiness for your first work on New Years Eve.
They will be training you daily for the next 2 weeks; then all being well they will become both your bodyguard and cashier”.
He looked at me waiting for an answer; I nodded a yes.
The woman then resumed “Here is your letter of consent saying you agree with all the terms; read it and sign it”.
I was spoken to again as soon as I started to read.
“If you do not agree and do not sign we will return you to Tex and leave it at that. However if you do sign there will be some amount of pain before you will be ready for work; we must make that clear”.
In the terms the main issues concerned breast enlargements, hygiene and daily sex with my minders without complaint. I noticed that all enhancements would be deducted from my pay at a future date. I summed up the pros and cons and signed the papers; not that I really had an alternative.
“Good I am now your Boss; any grievances are to be brought to me and only me. Gentlemen you can begin the training now” she left and I was led to my bed.
One of my trainers gave me a drink of water which I sipped as all four of them disrobed before my eyes. I was already dripping wet after all the talk, anticipation, excitement and fear.
They first forced me to kneel before the bed with my tits resting on it. My legs were kicked apart exposing my sex to allow the four guys to do as they pleased with me. Immediately I felt rough callused fingers testing the wetness of my pussy; “Look how wet she is already” I heard him say to the others.
“Today we will be training you in the art of taking excessive amounts of anal; try not to struggle and it will be less painful”.
It was impossible not to be tense; I had done anal before with Tex and teenagers, but these men were like gorillas. Then two fingers were pushed inside my wet pussy to obtain juicy lube to rub into my awaiting ass-hole. He then smeared a cold feeling substance in and around my ass-holes entrance; before starting to finger fuck it.
It caused me to moan a little “Good girl don’t fight it.” he said twisting his finger inside my hole. I shuddered and moaned as I was enjoying it; laughter came from the others when they heard me. Three fingers were being pumped into my ass; and I was grinding my hips attempting to get them in deeper. He smeared more and more cream inside my ass-hole walls. Then he pulled his messy fingers out and cleaned them in my wet cunt; before standing up.
Someone then slowly inserted a dildo inside my ass until it bottomed out; I grimaced happy with the fact my hole was breached. I moaned softly as it was pumped inside me; the gentle yet forceful thrusts had me grinding back and forth.
“That’s it fuck the dildo as if it was a cock.”
After a few minutes of that pleasure he slapped my ass and rolled a condom on; before putting lube on it.
“Ok slut it’s time for a real cock now”.
His cock slid past the first of two banks of resistance in my ass, when it breached the second I gasped in relief. His cock was much bigger and thicker than the dildo; I struggled to breathe though I did let out a small giggle. He sighed as he rested his cock inside me waiting for my muscles to relax.
When they did he patted my ass-cheeks and began sliding in rhythm; out, back in, out causing me to moan and eventually rub my pussy.
“Stop doing that and enjoy the ride” they told me as one.
He braced my ass and started to pound it with short quick thrusts; the pain I felt initially was replaced by pleasure. When the pounding became intense my moans became extreme; which encouraged him to go deeper without showing me any mercy. Soon he was ball deep and his grunting became louder than my moaning. My gasps of appreciation were mixed with smiles as I felt his cock swell inside the walls of my ass.
He then pulled it out and ripped the condom off. “Clean it good” he said as he pushed his cum soaked cock in my mouth.
They handed me another glass of water saying; “You did very well, but that was only the beginning”.
As I was touching my tender gaping hole someone quickly turned me over; and a different cock was inside my ass. Slowly he built up until the pounding began again; I think I surprised them when I grinded back matching each thrust. What a wonderful feeling it was; an erotic tingling spread all over my entire body.
The fucking of my ass became more savage; which forced my arms to grip the mattress with each violent surge of his hard cock. He must have loved it himself; because without any warning his condom was quickly full of cum deep inside my ass. After removing it he emptied the contents on to my lower back. My ass was slapped as I slumped back on the bed trying to catch my breath.
It was only a very brief respite as another fresh cock was soon inside my tingly sore ass. I became very well acquainted with each of their cocks before that very first lesson ended. They dressed and handed me yet another glass of water; “We will continue your training this evening” they smiled.
I collapsed on the bed not daring to move; when suddenly I was summoned for lunch by one of my minders. He gave me a white robe and escorted me to the showers; before going upstairs to the kitchen. After lunch I was shown the entertainment room which had a television. There were other girls hanging around who I met briefly; before I was escorted back to bed for some rest. Due to feeling so groggy I slept heavily until being summoned by a minder for tea.
After tea I was watching the Simpsons when they told me to be back at my cubicle in half an hour for further training. Rather gingerly I walked back to my sleeping area; closely followed by one of my minders. I could not understand why my head was in two minds; one half wanted to fuck; while the other wanted to sleep.
The horny side came out on top; I became so randy waiting for the minders to arrive that I had to pleasure myself; my hand was still rubbing my clit when they appeared.
“Okay; I see you couldn’t wait for us” they laughed out.
I quickly discarded my robe before placing a pillow under my chest; it was something to hug during the ass fucking.
“Well you are an eager one” said Robert who would eventually become my minder. He was chuckling to himself as he positioned my legs into what I discovered to be the perfect position. He put lube on two fingers and entered them inside my tight ass-hole; I was happy to have the pillow to hug.
I then watched them undress again; a cock was thrust towards me; and I was told to put a condom on it. After smearing lots of lube on my hand I started jerking the condom cock off; feeling it grow in my hand. When it was solid he took up his position at my rear and plunged it straight inside my ass. I screamed out in pain before I was swiftly told to shut the fuck up by the youngest looking minder. I was being fucked good and hard; and it felt really painful up my sore ass.
As soon as one blew his load another cock would replace it; it became a session of continuous rough ass fucking. All the time I was being pounded; the young guy was looking at me as if I was a worthless piece of shit. Robert who had the biggest cock fucked me a little more tenderly; perhaps he was giving me a little respite. During his fucking my pain disappeared and I became extremely horny.
They all went to the water drinking machine and began chatting; the young one returned on his own however. Instantly he thrust his hard on inside me; it felt different because the cunt was bare backing me. He was fucking me with hate; spitefully rough causing me to bite down on my lip in pain. It was not until he blew his load inside me that the others scolded him for not wearing a rubber.
While they argued I gingerly felt the gaping chasm that was once my tight little hole; I rubbed some cum around the entrance in an attempt to sooth the pain. They came back over to me; and unlike the morning they all fucked me again in a second training lesson. What their earlier argument had proved I do not know; because only Robert wore a condom. He told me to ask to be tested because of their foolish behaviour; he then took the three naughty boys aside to have a chat with them.
As I was drinking the water Robert gave me I realised they were not finished with me. One guy pulled me onto my back by my limp leg and placed a pillow under my lower back. They then all fucked me with a condom on. Now I was looking in to their faces as they fucked my well worn ass. I so badly wanted to play with my sloppy pussy when one of them began fingering me; I orgasmed immediately. Robert did not fuck me, but he slowly slid his hand inside my gaping hole.
“Oh fuck, God” I yelled out and grimaced.
He started fist fucking my ass; cum was oozing out over his lube covered wrist; I felt so stuffed and stiff. He allowed me to rub my pussy; good God I had never been this full; I cum with such great intensity.
“A the end of each anal session you will be fisted to make your ass muscles stretch out”.
I basically collapsed with exhaustion; and never woke until the next morning; when I was roused for more training.
More soon….
