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My Darkest Fantasy

Category: Gay Male
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I was about to turn thirty when this started. I had just split up with my girlfriend of six months pretty acrimoniously as I had found out that she was cheating on me. Unhappy with life I plunged into despair until I came across a BDSM site on the internet that took my interest . I had always been turned on and intrigued by the lifestyle and was in no doubt that I was submissive by nature as I was always getting used and taken advantage of.

Deep down I enjoyed that, I had a weird enjoyment of being embarrassed and even humiliated that I could never really understand. Until now that is. Reading the site and hearing what others did made me understand me a bit more and realise some things about myself.

I wrote to several Mistresses (or Dommes) online with no success and virtually no replies and it was then, just as I was losing hope of finding an answer here that I decided to write to a male dominant. I was not gay, nor had harboured any thoughts in that direction previously but his advert intrigued me. For a start he lived in a town only thirty minutes away from me, secondly he especially wanted straight men to answer him and finally he promised humiliation for any who dared write to him, and as I knelt naked reading his page and profile on my computer, the dark side of my personality craved humiliation and self abuse. So I wrote and applied to Master Max. Even now, knowing what has happened to me since, I do not know if that was either the best or worst thing I had done in my life – one thing is for sure it certainly irrevocably changed it.

His first reply back to me was not encouraging, short and sweet he demanded details about me, my life and a picture and stated not to bother even replying unless I was totally prepared to obey absolutely everything he told me to do. I hesitated before replying to him, unsure if I was doing the right thing but again a stiffening cock at the thought of what I was doing convinced me to give him all he wanted to know and the next night my phone rang.

“Is that John?”


“Good. This is your Master Max speaking”

And so he came further into my life. Even in that first phone call he informed me of how it would be his intention to humiliate me and degrade me, I think he wanted to give me a chance to back out of what I was embarking on. But I just gave myself over to his will. Ready to commit myself fully to this. He seemed pleased and before he had rung off I had told him more private details about myself and promised to send him more over the next week. Our first meeting would be at my house the next Saturday, where he promised me I would experience a day like no other that I had lived in my life up to then. All this must seem stupid and reckless and dangerous on my part, giving so much to someone I had never met before, in truth it was but I did not care, I had given up on myself by now as a person and whatever would come would come. And boy did it come!

All that week the Master got more and more information from me and by the time Saturday afternoon came around I was almost sick with worry and anticipation. At three o’clock exactly my doorbell rang and I quickly moved to answer it. As instructed I was completely naked when I opened the door and came face to face with the man I had given myself over to.

I knew he was forty eight but I was surprised how well put together he appeared to be, very muscular and an intimidating height. I stood just inside the door staring into his deep, dark, hypnotic eyes.

“Get down on your knees Bitch!” he spat at me “And never again look into my eyes, a pathetic specimen like yourself does not deserve to gaze upon me.”

He stood on the doorstep watching as I obediently dropped to my knees before him, conscious that if one of my neighbours or a passer-by were to look over they would see me like this in my own home, worrying, but it gave me a real thrill. He left me there for a minute before ordering me to crawl on hands and knees into my living room. There he pulled the blinds fully open, again ensuring that if anyone chose to spy through my window they would witness what was happening to me.

“So you’re the bitch that wants to me dominated and humiliated are you? I really was expecting better. Still we’ll have make do. You can start by cleaning my shoes with your tongue, I seemed to have stepped in all sorts on my way here.”

He towered over me as I crawled over to him and obediently dipped my head to his shoes and tentatively began to run my tongue over his black shoes.

“For fucks sake slave! That’s pathetic, get your tongue going harder” he bellowed at me and I cringed at the thought of my open front door.

I licked away for at least ten minutes and by that time my tongue was sore and felt dirty, and I felt like the lowest form on earth. My Master looked down at my cowed form and reached into a holdall he had come in with and threw a magazine onto the carpet in front of me. I could hardly fail to see the front cover and discover it was a hardcore gay porno magazine.

“Open it to page 37” he barked at me.

I fumbled my way through the pages until I got to page 37 – it was a two page picture of a young guy on his knees taking a cum facial from a standing older man. I knew I wasn’t gay but couldn’t deny the picture was erotic as I concentrated on it.

“Ha! Look at you (he prodded my hardening cock with his shoe tip) you’re turned on by that aren’t you? Aren’t you?”

My eyes lowered I could only answer “Yes Master” sheepishly.

“You wish that was you there taking that man’s cum, tasting it, feeling it splash over your worthless face, come on admit it.”

I knelt there and admitted it to him much to his pleasure and noted the rising at his crotch – it was not small. He laughed at my gaze and ordered me to grip my own cock and jerk off while I looked at the picture imagining I was the guy taking the facial. I was quickly fully erect at 6″ and in a world of my own tugging away at my penis, nearing a ball bursting climax.

“Stop!” the Master bellowed and somehow I managed to obey his command.

“You will not cum, this not about you and you getting enjoyment now crawl your way to your bedroom, quickly!”

So I crawled out into the hall, again praying no one was looking in and crawled up my stairs and into my bedroom, the Master always just behind me. When we were both in the room he ordered me up onto my knees so my head was level with his belt, my back to the door and told me to unzip his trousers and to release his hardening cock. This was the acid test for my submission and as a part of my mind ordered me to back out now I found my hands reaching out and unzipping him and bringing out a very thick, large circumcised penis whose eye I was staring right into.

“You want to taste it don’t you? You want to please me? Well go ahead, you may suck me.”

I did, taking this hot, sweaty slab of throbbing man meat into the warmth of my mouth and I began to lick it as he thrust it further into me until I nearly gagged, his pubic hair tickling my nostrils. He placed his hands on my head and continued to fuck my mouth for five minutes and I soon found I was lost in the moment and groaning with pleasure as I gave my first ever blow job to a man.

The haze I was in was abruptly interrupted when I heard feminine giggles from behind me. I managed to move me head and eyes enough to see who was there and with horror in my eyes I saw that standing there with amusement and amazement all over their faces were my ex-girlfriend, Julie and her two friends Lisa and Louise (who I knew both had never liked me).

Julie was an extremely attractive young woman of 27, make no mistake about that. She had an incredible figure, with curves in all the right places and dressed to show them off at every occasion. She had shoulder length light brown hair, always in the latest style and amazing green eyes. In short she was a beautiful girl and anybody would have thought me fortunate to be dating her. However, as a person she was not nearly so nice. I had initially been attracted by her looks and soon found out that they were the best things about her. In speech and thought she was vulgar and nasty. She thought nothing of bitching about people and slandering them behind their back. I tried to change her but there was no chance of that happening and although I enjoyed having sex with her, when I dumped her it was mostly a relief. She had been sleeping with this other guy for a couple of weeks and when I heard about it from a friend and confronted her she didn’t deny it, thinking I was the one in the wrong. I also knew that she hated the fact I had dumped her, she never got dumped!

Her small band of friends were a lot like Julie, very pretty but also pretty nasty and Lisa and Louise were the worst of a bad bunch. Lisa was a short stunning blonde with a huge cleavage while Louise a slim raven haired beauty that specialised in looks that could kill. Both (indeed all Julie’s friends) had never had much time for me and I knew they had bitched about me when I went out with her. Of course when we split Julie wasted little time joining that particular chorus.

So as I looked up and saw them standing in a line inside my bedroom watching me in this position my heart sunk. Master Max chuckled and said,” Thought I’d invite some old friends of yours along to see how you were doing.”

Just then the Master’s cock started to pulse and spasm and as I knelt there stunned by the appearance of my ex-girlfriend and her mates, he pulled it from my mouth and instantly launched a huge volley of cum over my face. It splashed into my eyes, my nose, my hair and into my gaping mouth, running down my chin. The white sticky strands clinging to my face like glue. I could hear his deep guttural chuckling as he fed his diminishing member back into my mouth, telling me to lick it clean.

To my horror I realised that Lisa had come forward and was busily pointing something at me, she came closer and I saw it was a picture phone. She was taking pictures of me on my knees, covered in cum and sucking an older man’s cock. Shame and humiliation coursed through me as I carried out my Masters commands.

“I always knew you were a sick freak”, bitched Julie, her voice a mixture of disgust and humour.

“Yeah,” added Louise,” Remember I said he must be a faggot to dump you. Well look, he is.”

“You should fuck his ass Mister, bet he’d like that” said Julie a definite challenge to this man who had contacted her that week and arranged for her to be here to witness this.

Master slipped his cock from my mouth and as he zipped himself up he smiled at Julie and replied “No, you should fuck his ass”, and bent down to lift a huge strap on dildo from his bag and hold it out to her.

Julie looked at the Master incredulously and replied, “No way.”

Inwardly I sighed with relief, relief that was swiftly lost when that little bimbo Lisa blurted out” I’ll fucking do it” and grabbed the sex toy from his outstretched hand.

I had actually met Lisa the same night I met Julie and thought that she had fancied me but I wasn’t interested and, I think, she had always had it in for me since then. I knelt there with a distraught look on my face as she hiked up the tiny skirt she was wearing and stepped into the harness, pulled it up and tightened it around her waist. From all appearances it wasn’t the first time she had strapped on one of these.

The dildo itself was made of solid, black plastic and was about 6 inches long, though from my eye level perspective of it , it looked a whole lot bigger.

“Now slave,” spoke the Master as Lisa strapped herself in,” you will turn around and beg the young lady to fuck you, you will plead that she take you roughly and while she is doing that I will present my arsehole to you and I want you to lick it. Understand?” 

“Y-Y-Yes” was about all I could say and all I got for that was a slap to my face.

“You will answer properly Slave. Understand?”

Shaking I replied “Yes Master” and turned bowed down to the smirking Lisa and begged her to do as the Master had said.

“Well turn around faggot boy and you’ll get what you want” was her response.

By now the Master had undone his trousers and lowered them presenting his hairy arsehole to me. Pathetically I reached forward with my head, extended my tongue and began to lick the rim of his arsehole. He pushed back onto my face, forcing my tongue deeper and I then felt Lisa’s hands on my hips and the dry plastic of the tip of the dildo press on my ass cheeks. Her hands pulled my cheeks apart and without further ado she rammed the dildo into my exposed backside.

It hurt like hell and I could do nothing save for try to concentrate on licking my Master as I was roughly ass fucked. Lisa seemed determined to make me squeal and when I managed not to react to her first insertion she became harder and harder in her thrusts until I could not help opening my mouth and howling. I was lost in my own pain and humiliation when I heard Julie speak again.

“Oh my god look at his dick he’s getting turned on by this”.

And it was true I had a raging erection.

Lisa continued to pump hard and enthusiastically into me, at turns slapping my backside and calling me all the demeaning names she could think of as she thrust harder and harder. By now my tongue was buried in the Master and I licked him out with all the enthusiasm I could muster, and yes there was no doubt , despite myself I was turned on. I wasn’t the only one though as I noticed the Master was fully hard again, Lisa was definitely getting off on fucking me and from the encouraging noises they were making Julie and Louise were too.

I felt a hand (Julie’s) circle the base of my cock and begin to jerk it off while Louise held a large beer glass from my kitchen under it. In seconds my cock started twitching and I shot a full load of sperm into the glass, Julie’s soft hand milking me expertly.

The Master looked over his shoulder and saw what was occurring and told Louise to bring him the glass and he also shot a load of cum into the glass to mix with mine. She set the glass to one side as Lisa continued while the Master seemed satisfied with my rim-job stood up, pulled up his trousers and watched Lisa bring herself off while continuing to penetrate me. Finally she finished and pulled the dildo from me, quickly unstrapping it. She stood back to straighten her clothes as I stayed on hands and knees trying to come to terms with what had happened that afternoon.

Julie walked over to the discarded strap-on and carefully picked it up, she moved to my face and said” I want to see you lick this clean you bastard.”

I looked to my Master but knew his reply and I was right as he nodded to me so I opened my lips and Julie fed the length of dirtied plastic into my gagging mouth. The three girls gathered round to goad and mock me as I sunk even lower before them, while the Master took the glass and headed to my bathroom.

The taste in my mouth was foul and I hated myself as I greedily sucked the dildo but again the humiliation was turning me on. Just then Master returned with the glass only now it was filled to brimming and the unmistakable stench of urine came to my nostrils. He handed me the large glass and I looked in disgust at it. The two lots of cum floating in a thick head on top of a full glass of his yellow piss.

This was too much. I could not do this and pleaded with my eyes to all four of them but was met with looks that all wanted the same thing – to see me drink this awful concoction while they watched me. My masochistic and self destructive instinct took over me and I felt that it wasn’t my hand that gripped the handle of the glass and lift it to my mouth. Master nodded and I began to let the fluid into my mouth.

“Don’t swallow it slave! Hold it and swirl it in your mouth” I did as he ordered and when he instructed it I let some cum and piss run from my mouth and down my chin onto my torso. All the time the girls took photographs on their camera phones. It tasted horrible but on command I swallowed it and drank the full glass, drips escaping my lips. What a pathetic sight I must have made.

Before I had quite finished the glass the Master took it from me and proceeded to empty the last of it over my head so that I knelt there before them all with cum and piss dripping from me onto my bedroom carpet. The girls got more pictures of me before leaving. Julie was last to leave and she glanced back from the doorway to see me looking up at her feebly. This seemed to set her off and she stormed back over to me and kicked me hard in my balls, making me flop onto the wet floor in pain.

“To think I even wasted one minute on a pathetic shit like you!” and with that she stormed out.

The Master left soon after leaving me lying pathetically on the floor, naked and humiliated. He left a note on the sideboard before he went.

“There’s instructions on that to where you should be and how dressed next Saturday morning. I expect complete obedience.”


I stood on a cold and wet Saturday morning freezing waiting for the Master to appear. I had no choice really, what had happened to me the week before was terrible and I hated myself for it but he had access to those pictures and witnesses to what I had done and also I had no choice because despite it all I had never been so turned on and excited in all my life. I thought about it daily and the prospect of what may occur the next Saturday.

The note had told me to be at a small car park on the edge of town at 9:30 and to only be wearing a long trench coat. Nothing else , and that if I wore any other clothes he would have me strip there and then. So there I stood shivering, having waited twenty minutes already when he came around the corner.

He walked up to me and began to unbutton my coat, I worriedly looked around – there were a few early morning shoppers at the far side of the car park. He undid the last button and swept the two sides of the coat apart to stare at my nakedness.

“Good. Well done Slave,” and he reached down and gave my cock a slow stroke, “Now do it up and follow me.”

I did as instructed and he led me over to the old style public toilets that bordered the car park. He took me in and we entered the last cubicle on the left. The place stank of stale urine and there was a constant drip from over to the left.

“Take off your coat, now give it to me, now get on your knees. That’s it, slide your legs back around the toilet bowl.”

I obeyed his every command and once I was positioned as he wanted her took a length of rope from his pocket and tied it around one of my ankles, he flung the rope over behind the cistern and tied it to my other ankle, this wasn’t looking good for me. He took two further pieces of rope from his pocket and tied them around my wrists and tied the ends to the grating at the top of either side of the cubicle. My arms were stretched up and behind me forcing my face forwards.

“You’re going to have a real interesting day slave” and with that he left the cubicle , attaching a Velcro strap to the door so that it wouldn’t open easily but a firm push would open the door. I knelt there in comparative silence , nervously awaiting what would happen to me.

Some time passed and I heard the noise of footsteps in the toilets, they came slowly along the building towards my cubicle and I gulped when I saw the door move inwards. With the way my body was tied I could do nothing else but look into the eyes of the man who entered and register surprise and dismay to see that it was Malcolm, a guy who worked under me at work a year ago and who I had to sack for misconduct.

There was a wicked smile on his face as her unzipped his trousers and whipped out a medium sized cock that was rapidly hardening.

“I’m gonna really enjoy this ” he snarled at me as he forced my lips apart and inserted his cock into it.

I had never liked Malcolm since he had started working at the sales office I worked in, one month after he started I was promoted and made sure he wouldn’t get away with his slacking as he had done in his first month. He was about 22 and thought he knew it all and could get away with it. I hate to say it but I got a secret pleasure telling him he was sacked and now here I was tied up of my own free will and taking Malcolm’s cock into my willing mouth. It wasn’t long before I was getting turned on by my humiliating situation and he laughed seeing me get hard at being forced to give him a blow job.

“I never had you for a cock sucking faggot, asshole ” he commented as he thrust his thin dick right into my throat forcing me to deep throat him, “Man, I couldn’t believe it when this Max told me you’d be here like this – man.”

He came pretty quickly, holding my head firmly as he shot his spunk into my throat and making me swallow his full load. When he withdrew he seemed suddenly conscious of his surroundings and couldn’t get away quickly enough , though he paused long enough to spit fully on my face before he left.

I knelt there for more than half an hour the sour taste of Malcolm’s cum in my throat and his spittle drying on my face when I heard footsteps enter the facility and braced myself for my next potential encounter. The door was slowly poked open and into my view came a long, dark nightstick, to my fright I saw it was being held by a tall, muscular ,coloured policeman!

All sorts of things went through my mind, how I could talk my way out of this situation, I had been attacked or.. Anything to prevent being busted. Then he prodded the nightstick into my mouth and I realised he wasn’t here to arrest me but to be serviced by me. I sighed a sigh of relief and then I laid eyes on his cock – it was huge! As his stick probed my mouth he unzipped his trousers and a massive black cock sprang to attention in front of me, it was so big I doubted it would fit in my mouth. He seemed to be testing that out by using his nightstick to stretch either side of my gaping mouth and then he fit that hog of a cock into my mouth, slipping his weapon out as his penis entered.

I gagged immediately and panicked and struggled for breathe, he had to instruct me to “Breathe through your nose Bitch!”. I tried but it was a struggle , he must have been 14 inches long and had a huge girth, my tongue doing little other than licking the underside of his dick as he pushed gently in and out. I hate to think what damage he could have done if he had been as rough as Malcolm had been with me.

When he came after a good twenty minutes of me taking his meat, and by then I was enjoying it, he pulled out and pulled back his foreskin and aimed his pulsing penis at my steady face and unleashed a torrent of cum over my features, my face was literally coated in his sticky cum when he unzipped and without saying anything further left me to kneel as some of his cum dripped off my gasping face.

Three more men came in the next two hours, all well spaced and through my haze of cock I realised that no-one else was using the toilet, it was either very quiet or Max had set this up really well. Who was this man? The men seemed to take their lead from the cop and all of them made sure to give me a facial with their cum as they came leaving me an increasing mess with each blow job.

It was about three in the afternoon by the time the next ‘visitor’ arrived. By this point I was really uncomfortable, my knees were sore from kneeling in the cold and wet all day and my arms were tired from being pulled in the direction they were in. I was stiff all over and just wanted the day to be over. Then suddenly the door swung inwards and someone came in, my view wasn’t as clear as before as my eyes had been a target for the previous guys and a crust had formed around them blurring things slightly. However, looking up at him I thought I recognised him and when he spoke it came rushing back to me.

“Hey Nancy Boy, remember me.”

How could I forget, at school only one person had called me that, Graham Spink, the class bully who had taken an immediate dislike to me and spent the best part of four years making my life a hell. He was bigger and meaner than me and had realised that I wasn’t the type to fight back so he took advantage physically and verbally, calling me all sorts of names, especially ‘Nancy Boy’. All those horrible memories came back to me and here I was tied up, on my knees, caked in other men’s cum, confronted by the chief tormentor of my teenage years. This would be terrible I knew. I had hated him then and consoled myself with the knowledge he would grow up to be a waster while I would be a success.

He slapped my cum-covered face pretty hard as he inspected my predicament and took out his cock. He had no intention of shoving it into my mouth, as he took delight in telling me, “he wasn’t a faggot cocksucker like me”. What he did do though was handle his prick so it pointed at me and unleashed a fast spray of yellow, acrid urine all over my exposed face. It splashed off my head, into my eyes, up my nose until it settled on my mouth.

“Come on open up Nancy Boy” he goaded me.

To my shame and humiliation I found my mouth opening up and I took the full force of the spray into my mouth, swallowing some of the vile liquid while the rest swirled around in my mouth before dribbling down my chin to the stone floor. It seemed to go on forever but when at last he finished, the cubicle stank even more than before and my entire body seemed to be soaked with his piss. He zipped up, smirked at me then shook his head at how pathetic I was and left.

I had three more men to suck off that afternoon, I did it almost mechanically, my spirit crushed by then and when at 5:30 Master Max cam to release me I flopped pathetically onto the stone floor. He had one final humiliation for me though and he ordered me to crawl on hands and knees, naked into the main area of the toilets and up to the tiled floor before the urinal trough. This was overflowing and stank. He explained to me how that morning he had jammed it up and that each of my visitors had been encouraged to take a piss in it before leaving.

He took out a video camera and told me matter-of-factly that I would have to drink it dry before he would allow me to leave and that he would film me doing so. Anything for this day to end, I thought and reached a new low as I lowered my head to the trough and began to lap at the disgusting mixture. He stood over me egging me on and even at one stage put his boot on the back of my head and plunged it into the piss, threatening to drown me in it. He released me laughing even more and when I managed to get the level lower he handed me a straw which he told me to use to make sure I emptied the trough. It took me the best part of an hour to do but I finished it eventually.

“Well done Slave, you are really showing your obedience to me and I must say I am enjoying humiliating you. When you arrive home tonight you will find instructions that I expect you to carry out to the letter, failure to do so will see a copy of this tape sent to your parents. Understand?”

I could only nod and trudge into the night to see what my next fate would be.

I got back home and tiredly lifted the note and package the Master had left on my kitchen table ( how had he gained entry? ). The note read as follows :

“Well done so far Slave, you have pleased me with your actions and I know how much you will have enjoyed your humiliations. In the box are garments that I expect you to wear to your work every day next week under your normal clothes. I will check on this happening at some stage so do not fail me. However, tonight I want you to shave all of your bodily hair off. Make sure you are thorough, I especially do not want any hair left around your crotch or ass and legs.”

I opened the package and carefully lifted out a frilly bra, frilly panties, garter belt and stockings all in a very feminine pink colour. I was no cross dresser and had no desire to wear women’s underwear and the thought of being forced to run the risk of someone at my work discovering I was wearing them both repulsed and excited me. I went to have a long, hot bath that night to wash away the crust that covered me from the day and to contemplate what I was becoming. I then set about shaving myself which took some time.

Of course I wore the clothing each day that week to my work under my clothes, making sure I wore a dark shirt each day for fear someone may see the bra’s outline. I have to admit that I was turned on, not by what I was wearing but by the thought of being caught and what could lead from that. Then when I returned from my lunch break on Thursday I entered my office to find the Master sitting in my seat, dressed in bikers leathers, his boots cockily perched on my desk. 

I entered and shut the door behind me and immediately sunk to my knees before him.

“Nice office you have here slave. Nice secretary too, what’s her name?”

My secretary was indeed a pretty little thing, not long out of school Louise was nevertheless extremely competent at her job , the only drawback to her seemed to be that she was a gossip in the office. 

“Miss Goodhead, Sir.”

“Well I am ordering you to ask her to come in here right now.”

Feeling extremely uncomfortable about where this might end up I nevertheless obeyed and through the intercom asked her to come into my office and to close the door behind her. She came through swiftly and as she closed the door both the Master and I appraised her. She was 18, tall, had a nice figure, very big boobs and beautiful long, blonde hair. She was wearing a sheer white blouse and a short dark skirt with black stockings. She had a puzzled look on her face as she looked at the older man who so confidently occupied my seat.

“Those are lovely stockings you are wearing Miss Goodhead, do you often wear them to work?” he asked her. She stood there frozen unable to work out how she should answer. He ploughed on not waiting anyway.

“Of course you’re not the only one who like to wear stocking to work is she slave (his use of the word before her stung me and I grimaced as Louise listened )? Why don’t you show her she is not alone – take off your shirt and trousers now.”

They both stared at me each, for different reasons, waiting to see if I would do what he commanded. Lowering my eyes I reached up with my right hand and began to tug at my tie. The master smiled as I continued to undo it, letting it drop to the floor then I unbuttoned my blue shirt and let it fall allowing both to view my hairless chest covered by the frilly pink bra. My face burned red with shame when I heard my secretaries little gasp of surprise when she saw the bra, what had I done? There was no turning back though and automatically I kicked off my shoes and socks before the Master stopped me.

He got up from my desk and locking his eyes with those of the transfixed Louise he strode over in front of me. He gripped the buckle of my belt and forcefully undid it before unzipping me and pulling my trousers off. I stepped out of them at my ankles and stood before them clad in my bra and panties and stockings.

“Look into Miss Goodhead’s eyes slave, tell me what you see there, tell me what you think she must think of you now.”

I looked across at her and saw a mixture of surprise, amusement, disgust but mainly an enjoyment of the humiliation I was undergoing. I told him all that.

“Hmm, Miss Goodhead, I’ll bet you never thought you’re boss enjoyed wearing women’s underwear did you? No, well there’s a lot you don’t know about him, he’s a kinky little bitch who’ll do whatever he’s told. Try him, give him a command he’ll obey.”

She smiled uneasily at what was going on, unsure how to react but you could also see that she was in some way aroused by the situation and when she spoke that young voice had a real edge to it that I had never noticed before.

“Take your panties off.”

I paused only to be struck by the Master and told to hurry up and obey her. I peeled the pink panties from around my crotch and pulled them off, revealing my freshly shaven pubic area and my semi-erect penis. She came closer to me, as if to inspect and dismiss my tiny cock, then spoke again.

“I never had you as one of them, just goes to show you can’t trust the quiet ones. I bet you like sucking cock don’t you? (I nodded) Yes, and I’ll bet you like being buggered don’t you Mr. White?”

To that I never responded but the Master did by ordering me to lay over my desk and telling Louise that he would show her exactly what I liked. I gripped the edge of the desk and grimaced as I heard his zipped being lowered. He was going to fuck me in the ass here, in my office while my secretary looked on. And she did look on now, no thought of hiding her arousal, she felt her boobs and I saw a hand reach into her skirt as I felt the Master’s fat cock head touch my ass cheeks and braced myself for the assault to come. He was not gentle with me, I believe he was trying to make me shout out or squeal , knowing that although my office was closed and there were no windows that surely others would hear my moans if I made them too loudly so he pistoned his cock into my arsehole as hard and as fast as he could as I hung onto the far side of the desk and stifled the screams and shouts I needed to let out. I felt him climax inside me then withdraw and do up his trousers. He swiftly made to leave the office pausing only to say ” Miss Goodhead, you can do one of two things, one, tell everybody what you saw here or two keep the knowledge to yourself and have a boss that is unbelievably indebted to you, you might say under your control. I leave it to you what you do. Slave (addressing me), I will call round for you at eight tonight for the next part of your journey.” 

I got into his car that night with some amount of trepidation, I had the feeling that the Master had lined up the ultimate humiliation for me and that after tonight I would never be the same again. Still I went with him and I felt excited about what may happen as well as my ever present worry.

We booked into a dirty, seedy hotel in a run down area of town and I carried his suitcase up to the room while the duty manager gave the two of us a leering look as if he knew what two men would be up to in one of his rooms. Once in the room he had me strip naked and ordered me to wear the clothes in his suitcase. Not that there was much, just a wispy, short lacy teddy and that I pulled on.

“I have a guest coming up in ten minutes, when he arrives I will move to the bathroom and watch the pair of you. He has been instructed not to turn on the lights, you will not speak to him or communicate with him. You will merely kneel before him and accept his cock into your willing mouth and give him the blow job of his life. He had better be satisfied or I will make things far worse for. When he comes in your mouth you will begin to masturbate yourself and put a finger up his arsehole while keeping his semen in your mouth. Understand?”

I had accepted my desired role by now and merely nodded my ascent. Seconds later there came a knock at the door. The Master retreated to the small bathroom while I shut out the lights. The room was engulfed by light when the man entered but plunged to pitch dark when he swiftly shut the door. He stood by the bed and I moved over to him, sunk to my knees and eased his trousers down, slowly playing with his hardening cock.

He seemed to be a tall well built man, very hairy with what felt like pretty big cock. I slowly ran my tongue over it and began to explore under his foreskin with my lip. It was a bizarre thing, the two of us in complete silence and darkness as I orally pleasured him. Soon I had his full length in my mouth and was sucking like a pro. His pubic hair tickled at my nostrils as his full length rammed into my mouth and I concentrated on pleasuring him. All too soon I could feel him tense up and begin to moan (which sounded like a shout in the silence), then I felt a rush of warm, stickly liquid in my mouth and remembering the Master’s instructions I reached my left hand up and probed his butthole with my index finger and began to tug on my rock hard erection.

Then the bathroom door flew open and the lights came on, the Master snapped of picture and snatched up a video camera he had been filming with and laughed and ran from the room. Stunned I looked up into the man whose limp cock still touched my lips and whose cum dripped from my mouth and whose arsehole I was fingering. I nearly howled in anguish to see I was looking into the eyes of my older brother James.

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