A New Job

A teen side hustle turned humiliation.

At the age of 18, it was time for me to find a job on the side to earn some money. I was approaching the final year of school and wanted to make sure that the summer before I go off to college was one to remember. I lived with just my mum as my dad left us when we were younger. She provided well for us, mom was always working overseas and earning good money. This meant that most of the time, I was living alone. I went online one evening and found a job that was local to me. The job title was - part time masseuse needed. The description gave me confidence. Training on the job and good pay, for me it was a no brainer.

I went along to the parlour after school the next day. I probably should have gotten changed out of my school uniform but I wanted to apply straight away. When I arrived there were two older women, in their 40’s. I had only gone in to apply but they apparently became fond of me quite quickly. There were a few things that were needed from me before they could offer me a job. So there was a small interview process. They didn’t seem to care about my age which was great. They had also asked me a few personal questions about my body etc. The women asked me to undress so they could see my body. I found this strange but I wanted the job so I began to undress.

I’m 5ft2, I have blonde hair, green eyes and a tanned body. My boobs are sized C and I have a fair sized butt. The women complimented my body and told me that I had the right body for the job. This probably should have been a sign that the job would be strange but I was naive and wanted the money. At the end of it, I was offered the job. They gave me a usb stick with all the information on and that I would start Friday evening.

I went home and opened the files. I can’t lie I was shocked to say the least. The information provided showed me that I would need to keep customers happy. When I say happy I mean sexually satisfying them after massages. Along with naked body to body massages. I was barely 18 and I couldn’t believe what I had signed myself up for, but all I could think of was that I was getting paid. Even if it was at the cost of my virginity…

It got to Friday and I was super nervous about my first shift. I had been watching the videos that had been attached to the file to learn what to do. To make matters worse, I had a meeting with the headmaster of the school. My grades weren’t up to scratch and apparently that warranted a meeting. The headmaster was called Mr Johnson. He was a tall old black man, that must of been in his late 50’s. He was a very intimidating man, that would shout at you if you acted up. I arrived at his office, where he opened the door and towered over me. He let me in and I sat down.

“Now Maddie, we need to have a chat about your grades,” Mr Johnson said to me with a stern look. “It’s not been up to the standard of this school.”

Without meaning to just as he finished talking, I accidentally let out a yawn. The tiredness was creeping in from staying up late. This didn’t go down well…

“Am I boring you Miss? Do you think this is some sort of joke?” Mr Johnson rose his voice with much anger.

“No sir, I didn’t mean to yawn.” It was too late for my plead, as he was now giving me a full on lecture.

“You know what happens to girls whose grades are not up to standard in this school? They get spanked with the cane,” Mr Johnson stood up in front of me, his crotch was directly in front of me as he looked down at me. For a moment I felt like he was really perving over me, I felt very uncomfortable. “Now, this is your last chance to get your grades up. This will also be the last time you disrespect me. If you were my daughter I would have pulled down your skirt and spanked you with my bare hands.”

This comment made me gulp. I couldn’t believe he said it to me. However, I chose to ignore it as there was too much on my mind at this moment in time. He opened the door and showed me out of his office. Mr Johnson then locked the door behind me. I made my way to the last class of the day and gormed out of the window, slowly anticipating the night ahead on my first shift. Just as I was about to leave, my teacher Mrs Taylor told me I needed to stay behind. Long story short I was going to be late for my first shift, as she demanded that I stayed for extra lessons to improve my grades. I had no way of contacting the parlour to say I was going to be late either as my phone had died. This day just kept getting worse.

The lesson had finally finished at around 6pm. I was 2 hours late for my first shift. I quickly made my way to the parlour, it was a hot day and I was sweating from speed walking/jogging. When I arrived, the two women had hugely disappointing looks on their faces.

“What time do you call this?” One of the women asked me looking mildly pissed off. I tried to explain the situation by going through everything that had happened at school. However, they didn’t seem to care.

“Listen Maddie, I know this is your first day but you can’t be showing up late okay? There’s one more customer for today who is arriving in a few minutes and you are going to be the one looking after them. We are going to leave you the keys, once you are finished make sure you lock up properly and we will see you tomorrow.” They handed me the keys and left, just like that. I was in total shock, leaving an 18 year old in charge on their first day? Crazy I thought.

I went into the room where we get changed into our uniforms. I set my bag down onto the floor and the next thing I knew, the shop door opened. “Fuck” I thought to myself. Didn’t even have enough time to go and get myself changed.

“One moment!” I shouted out so they knew I wouldn’t be long. I stood there and made sure I looked presentable. I was still a bit sweaty from the journey. I probably shouldn’t go out and introduce myself in my school uniform but it would have taken me 5 minutes to get changed. I felt like I had no choice, I walked out into the entrance room.

“Hi, my name is Ma…” I stopped mid sentence in complete and utter shock.

“Maddie? I didn’t know you worked here? What are you doing here?” An older man’s voice said.

“Um Mr Johnson…” it was my headmaster standing there right in front of me.

“I must say Madison, I’m hugely disappointed that you work here,” although he sounded angry you could see a smirk behind his eyes.

“Sir, I’m the only one in this evening. You will have to reschedule, I really am sorry. Please don’t let this affect my issues at school, I’m begging you.” All I could do was try and send him away. Judging by the massage options here, there was no way I would be doing any of them on my headmaster. How creepy that he comes here for pleasure?

“I’m afraid I have already paid for this session Madison,” unusually he kept calling me by my full name.

“Can I not just reschedule you for someone else to give you a massage?” I questioned innocently.

“I will have to make a complaint to the manager here if that’s the case…” Mr Johnson said deepening his voice. I was shocked at what was happening.

“No please don’t do that,” I tried to reason with him, it was my first day and I was already late. What would they do if they knew I refused a customer? Surely they would understand?

“Well then, you will have to do won’t you Madison. Maybe we can continue our chat from earlier?” Mr Johnson said.

“Umm o-okay, what are you booked in for today?” I said with panic in my voice, stuttering.

“I’m in for a nuru massage.” Mr Johnson walked past me into the room where Nuru Massages are performed. My heart was racing super fast, endless thoughts running through my mind. What the fuck is happening? I kept telling myself.

I followed my headmaster into the room. Unsure on where to begin. I just stood there feeling awkward and shy.

“What is this? Your first day?” Mr Johnson raised his voice like he did earlier.

I stood there for a moment to try and recollect my thoughts and remember the videos I had watched. It then came to me, I would have to help him undress. I felt sick to my stomach, it must of been a dream. I approached him shyly and lifted began removing his suit jacket. A strange musky smell waved over me. We were both silent. I then reached up and removed his tie, our eyes locked for a moment but I immediately looked away. Then came the shirt, I slowly unbuttoned his white shirt until I could see his grey chest hair on his black skin.

Now the part I was dreading. I removed his belt and unhooked his suit pants. I bent over as I pulled them down and it was horrifying. He was not wearing any boxers or briefs. A long thick vainly black cock fell out and nearly hit me in the face. I was sweating once again, it was huge. Much, much bigger than anything in the videos. I muttered “holy shit” under my breath. My headmaster was now naked in front of me. I once again stood there, trying not to look at him.

“Well Madison, I think it’ll be slightly uncomfortable for me if you left your clothes on. Don’t you think?” Mr Johnson said to me with the same stern face he had while telling me off earlier.

I nodded. I began removing my blazer and let it fall to the floor. You could easily see that I was sweating in my white shirt. I removed my own tie and began slowly unbuttoning my shirt. I begrudgingly removed it so that my headmaster could now see my white bra. I looked over at him and I could see his cock was growing even larger. I tried to turn my body slightly, feeling extremely uncomfortable. I then unhooked my skirt and began pulling it down. It was always a little bit difficult pulling my skirt down over my ass. I had a matching white thong on that was now on show. I tried covering myself up but it was pointless. I knew I had to keep going.

I started to remove my shoes and socks first of all before moving on to the more revealing stuff. I looked over at him and his cock was now pointing directly at me. Mr Johnson licked his lips as he watched his student undress. I unhooked my bra and let my breasts fall out but covered up my nipples immediately. My bra dropped to the floor. I then began sliding down my white thong, while also trying my best to cover up my hairless pussy. I was now completely naked, head to toe.

“Follow me,” I said quietly to Mr Johnson as I led him to the shower. We were both in the shower room, I turned on the tap and the water poured over us. I eventually had to remove my hands from covering myself up. I grabbed the soap gel and squirted it onto my hands. All I wanted to do was leave but I knew I had to do my job. I began rubbing the gel onto my headmasters back massaging it in. It was only 30 seconds before he turned to face me. His cock swung and hit the top of my stomach. I was still in total shock about what was happening. I looked up and he was staring down at me with intent. I began massaging the soap into his chest and stomach.

I tried my best to avoid touching his penis, so I rubbed down both of his legs. However, just as I was coming back up his leg Mr Johnson grabbed my hand and placed it onto his penis. I froze for a moment and didn’t know what to do. I just slowly moved my hand back and forth over his shaft. This didn’t last long as I quickly turned the shower off. It was time for the massage…

I told him to lay himself front down onto the bed. I grabbed the pot that was filled up with fresh nuru gel and sat behind him on the bed. I did all of this while remembering what I had watched before. I put the gel onto his back and used my hands at first. Rubbing his back with the gel and slightly over the top of his backside.

“Madison don’t make me show you how it’s done. You’re meant to use your body,” Mr Johnson rose his voice again.

He was right but I really didn’t want to do it. I gave in and sat myself on his lower back. I rubbed the gel all over the front of my body and laid my front down onto his back.

“Mmm,” Mr Johnson grunted.

It was revolting, I began rubbing my body up and down onto his back. My breasts squeezed down, being used as tools to soothe him. Once again this didn’t last that long, as Mr Johnson wanted to turn onto his back facing me. His cock was as hard as ever.

“Carry on now,” he said smirking at me.

My heart was racing super quickly again. I perched my leg over him but tried my best to avoid his cock. My pussy was now sitting on his abs as I moved myself up and down trying to not look at him. Here’s where things got worse. Mr Johnson unexpectedly grabbed onto my ass as I was sliding up and down.

“I think it’s time I punished you for your grades and disrespecting me,” Mr Johnson said as he slapped my ass. I froze again not knowing what to say. “Yes, I think it’s the right time to punish you.”

Mr Johnson removed me from him and told me to stand up. He propped himself up next to me and ordered me to bend over the bed. He was a scary man and I felt like I had no choice but to follow his order. I slowly knelt myself over the bed.

“Good girl, now I’m going to show you what happens to girls who disrespect me.” Mr Johnson picked up his belt and used it spank my bare ass with. I screeched out loud. He didn’t stop there, Mr Johnson struck me 5 more times. My butt was burning and in a lot of pain. I peaked behind to see him now stroking his cock. Mr Johnson then picked me up and put me onto the bed, positioning my body so I was bent over on my knees with my ass in the air. This made my bare asshole visible, I couldn’t begin to tell you how uncomfortable I felt.

The next thing I knew my headmaster had dropped onto his knees and buried his face into my ass. He was molesting my asshole and pussy with his old black tongue. I could feel his sharp beard rubbing against me. I tried to push him off but he locked my arms together and continued without another thought. I felt my pussy become wet, the strange sensation of a tongue pushing into my young pussy and swirling around my tight virgin asshole. He pushed a finger into my pussy while licking my pucker. I screamed out, it was the first thing to enter inside of me.

“God damn, that tastes so good,” Mr Johnson said in a deep voice before standing up onto his feet and he then told me to look him in the eyes.

“You’re going to have to suck this cock if you want forgiveness Madison,” he said while standing there stroking his huge cock.

“Please sir, don’t make me do this,” I cried out and continued to plead. He grabbed my hair and pulled my face in towards his cock. He pressed it against my lips. I had no choice but to open my mouth. He pushed his cock into my mouth, it tasted funny. I submitted to him and began sucking my headmasters cock. Fortunately I didn’t have a gag reflex so it was affecting me that much. That was until he began pushing into deep into my throat. I looked up at him and I could tell this turned him on even more so I quickly closed my eyes. My throat was being used by this huge back cock that belonged to my headmaster. The same one that I have had since I started school.

Mr Johnson was grunting as fluid fell down onto my breasts. He then pulled out and pushed me onto my back and immediately positioned himself over me. He placed his cock against my pussy.

“Please sir, don’t do this. I’m still a virgin!” I moaned out to him. All I saw as I looked at him was a widening grin. This egged him on even more.

He pushed his cock slowly into my pussy. It felt like it was being torn apart. I screamed at the top of my lungs, I grabbed onto the wet black sheet that laid over the bed. Mr Johnson was grunting loudly. It was only the tip in but he kept pushing more and more in. My eyes were rolled to the back of my head, everything became blurry. His cock was now moving back and forth. His hands were grabbing my breasts and then my nipples were being squeezed. I looked up to see my headmaster looking into my soul as he began fucking me.

“Uhhh, fuck, fuck, no, fuck,” I barely moaned out.

“I’ve been waiting to fuck you for a long time Madison, I’ve been watching you grow up. Watching your body fill out,” Mr Johnson said while continuing to grunt loudly.

“You sick creep,” I shouted out.

Mr Johnson began thrusting faster after I shouted that. I could barely take it. A tear rolled down my face. My legs were shaking like crazy. He eventually pulled out. My pussy was throbbing, I could feel liquid flowing out of me. Mr Johnson then flipped me onto my front again. He put me back into that same position, positioned his cock and re entered inside of me. This time it felt even more painful inside.

“Ughhh, that sweet, sweet ass. Just watching you run in sports Madison. I’ve always wanted that ass,” Mr Johnson moaned out as he began fucking me again. All I could think about is how much of a fucking perv he is. It all felt so wrong, I still couldn’t believe what was happening.

My face was buried into the bed. All I could feel was something huge buried deep inside of me, thrusting back and forth. Mr Johnson hand dipped his hand in the nuru gel and began rubbing it all over my ass. His thumb was then pressed up against my asshole while continuing to fuck my pussy. I tried to reach behind a push his hand away but once again I had no luck as he grabbed onto my hand a placed it behind my back. His thumb then pressed inside of my pucker, I tried to move but he had me locked in. I was only small so didn’t have much of a chance.

He was really forcing his thumb inside my asshole, I was being penetrated in both holes. I felt a strange sensation that I had never felt before. I was hoping it would be over soon, I couldn’t take his cock inside me anymore it was too big. However, he wasn’t finishing anytime soon by the looks of it. Mr Johnson had pulled out of me. I felt my body just collapse onto the bed for a moment.

Mr Johnson picked me up and made me sit on his cock. I was facing him, sitting on top of him like I was a cowgirl. He re entered inside of my pussy that was now stretched out. He was slowly thrusting inside and out of me. His lips perched onto my nipple, it felt like I was a doll.

“I want to hear you say fuck me daddy!” Mr Johnson moaned out.

“No fucking way,” I cried, hating every moment of it.

“Come on, say it or I’ll fuck your ass,” he aggressively said as he slapped my ass and began fucking me harder. I didn’t want anything in my ass, I felt defeated. I really didn’t want to call him daddy but I had no choice.

“F-f-uck me daddy,” I muttered under my breath

“Say it louder,” Mr Johnson shouted as he pushed his finger into my ass again.

“Fuck me daddy,” I screamed out.

“That’s right Maddie, uhhh. Ride it like you mean it and say it again.” Mr Johnson went still waiting for me to move on his cock that I could still barely take.

I began moving my hips slowly back and forth. His hand reached round to my asshole again. So I shouted “fuck me daddy, please fuck me.”

This had made Mr Johnson go fanatical. He grabbed onto me tight and stood up off of the bed while still inside of me. He began fucking me hard, moaning even louder.

“Oh Maddie, oh Maddie,” he shouted while pounding my teenaged pussy. “I’m gonna cum, I’m gonna cum.”

“Please don’t cum inside of me, please no,” I tried to reason but it was too late.

“Uhhhhhhhh fuck,” he moaned at the top of his old lungs. I could feel warm liquid pump inside of me. While he continued to thrust himself back and forth. Cum dripped outside of me over my pucker. My horrible headmaster had impregnated me with his cum. It was disgusting, I was in utter shock.

He walked me over towards the shower while still inside of me and pulled out. He made me get onto the floor. He aimed his cock right towards me. Suddenly a stream of his piss shot out of his cock, soaking me in old man’s urine. I felt disgusted and humiliated. Mr Johnson then pointed the shower head at me, it was freezing cold.

“There’s a good slut,” Mr Johnson said as he finally turned off the shower. He then handed me a towel and told me to dry myself off. While I was drying off, he got changed back into his suit. All I could think about was going home. I was about to get changed back into my school clothes.

“Is your mother home Madison?” Mr Johnson asked me. I shook my head, she had just gone away for a month.

“Well this just gets better doesn’t it? You won’t be needing these then.” Mr Johnson picked up my clothes and shoved them into his duffer bag.

“What are you doing?” I asked Mr Johnson, I was confused.

“Come with me, your punishment has just begun,” he said removing the towel from me and grabbing my arm.

We went outside the front of the parlour. I was still butt naked, I couldn’t feel more humiliated. He locked the door and made me get in his car.

“Where are we going?” I asked.

“Back to my house. You are my personal whore now!” He said grinning.