Big Black Transvestite Mistress

Before i begin my story of how i ended up submitting to an enormous black transvestite woman. My name is Chris, I am 27 years old and i am a well paid, freelance computer programmer and web designer.

Physically, i am nothing special. I am 5 feet 9 with a slim body which i like to keep in shape with cardio at the gym. I also have a shaved head (not through choice unfortunately) with a short groomed goatee to compensate.

It was early one afternoon on a Friday and i was working hard on a new website proposal for a big client, but i found myself unable to concentrate. I was so incredibly horny and i knew that i wasn't going to get anything productive done until i had some release. This was a regular thing with me lately, it had been far too long since i last had sex.

I leaned back in my chair, raising my arms above my head to stretch and letting out a big groan. I decided to load up some free porn websites and find something good to rub one out over.

I had quite a diverse range of sexual interests and fetishes but I was currently into watching dominant black women having their way with helpless white guys.

I found these women so incredibly sexy, especially women with over exaggerated cartoon like features such as enormous backsides, big thick bulging thighs and huge fleshy tits. I was getting so horny thinking about it as i scrolled through the videos trying to find something. I found a video i hadn't noticed before and quickly clicked on it without reading the descriptions.

The video started with a beautiful black woman on the phone ordering herself a taxi. This woman was so striking, big and tall with huge full breasts spilling out of her floral summer dress. As her taxi arrived she got in the back and began to flirt with the driver. It was quite cheesy stuff in all honesty but i actually quite like it when porn has a little pre amble and build up.

As the video continued, I absentmindedly replied to a text message i just got through on my phone. As i looked back up at the screen the taxi driver was now in the back seat with with this beautiful black goddess and he was sucking on her big black dick.

My mouth dropped open as i continued to watch. I wasn't interested in this kind of porn so i went to close the video, but i found myself unable to close the browser as i stared intently at the absurd scene in front of me.

The taxi driver had such a look of wanton lust in his eyes as he sucked her massive penis, bobbing his head up and down in a slow motion as he appeared to really savour the taste. Every time he moved his head back up, he left a coat of saliva down her shaft which made her black cock appear impossibly shiny.

I shook my head as i reminded myself that i wasn't into trans women but found myself entranced by this black dominant goddess and this willing submissive white guy on my screen. She had now pulled her huge tits out of her dress and was toying with her nipples as she called him playful names like "cocksucker", which only seemed to spur him on as he devoured her thick cock even more.

Eventually the video ended with this beautiful woman holding his head in place, while she deposited her load deep into his throat. As her milk started to spill out the side of his mouth, he looked up at her and said "thank you".

I couldn't believe the absurdity of it, i have never had a girl thank me for letting her suck my dick, i mean iv'e probably said thank you to them but never the other way round. Yet somehow in my mind i found myself wishing it was me in that taxi drivers position, on my knees with a black shemale's dick in my mouth and thanking her for the privilege.

Without realising it i had my hands were in my shorts and i was slowly stroking my cock. I pumped away furiously and before i knew it i tensed up and came as hard and quick as i could ever remember.

Ironically i had just blown my load at the same time as the beautiful shemale on my screen as she was now wiping her spit and cum covered cock across the taxi drivers face in a final act of humiliation. I quickly closed the web browser and cleaned myself up and set about finishing my work.

Despite the looming deadline for my work and the fact that i had shot the biggest and hardest load that i can remember, i soon found my self still unable to focus. I was rock hard again in no time as my mind kept quickly wandering back to that beautiful woman's big black cock.

Why was i thinking about it?, i had no interest in men or cock. I had once gotten a blowjob from a bloke when i was drunk and although it was pretty damned good, i never, ever think about sucking someone else's dick myself.

I closed my work down for the day and decided to see if there was any shemale's nearby. I browsed on dating sites, swinging sites and everything in between but found no one that matched what i was looking for, it was mainly a load of hairy guys in dresses.

As i kept on searching i eventually i stumbled across a transsexual escort website. I had never paid for any kind of sexual service before but i thought this would probably be the best way of meeting one. As i scrolled through some profiles i browsed through all manner of different trans women. There was transsexuals and transvestites, lady boys and fem boys, dominatrixes and subs. Some of these women were passive, active or switch and some had big tits or no tits. It was an absolute mine field to chose from, but i knew exactly what i was looking for when suddenly a profile caught my eye and to make it even better, it said that she was on tour and staying in the city centre close to where i lived.

My pulse was racing as i clicked on her profile, "Maddison, big fat black tranny 4 U", the heading of her profile read. As i looked further through her profile, the more i was in awe of her. She had her make up very heavily done, with thick red lipstick on her lush plump lips and eye shadow with long thick eye lashes. She had clearly put a lot of effort into looking as feminine as possible.

She also had thick, long blonde hair which definitely looked like a wig. She described herself as a transvestite, which was a shame as i love big tits but i still found myself attracted to this ebony amazonian.

As i scrolled through more of her pictures i found myself looking at a full body shot from behind and my word she was incredibly tall, easily well over 6 and a half feet tall in her heels. Her skin looked so clean and smooth and her legs were long and thick like tree trunks as i traced them up to her ass.

Her ass was so big and thick, like two massive wrecking balls framed in a beautiful high waist thong. She described herself as fat and while she was definitely a big woman, in no way would i of said she was fat or anything. Her curves looked very soft yet also firm and solid at the same time, she had a little belly but it looked well in proportion with the rest of her.

Then i saw it, a picture of her cock and it was absolutely massive!. I gulped and swallowed hard as i saw her long thick black cock hanging between her legs, she was circumcised as the thick red bulbous tip was very prominent even though she wasn't fully erect. I found myself furiously stroking my raging hard on through my pants as i began to read about the services she provided.

I continued to read a little more about her services and was immediately drawn to her domination service. The domination section on her profile listed a rage of interests and fetishes she offered such as bondage, oral, face sitting and humiliation.

I stopped reading as i imagined being humiliated in a variety of ways by this big black mistress, and my cock was now aching at the prospect. Without even thinking twice i entered her number and dialled as the phone rang a few times before someone finally picked up.

"Hello" answered a smoky, feminine voice.

"Um Hi, is this Maddison" i replied a little shakily.

"Yes it is baby, what can i do for you?" she questioned in a very obvious seductive tone.

"I was hoping i could arrange to meet you tonight for an hour, if your available that is".

"Sure baby, im available from 8 this evening if thats any good".

"Yeah sure that would be fine, i erm" I struggled to get my words out, wanting to tell her that i wanted to be her bitch.

"What kind of booking are you looking for sweetie" she asked as she clearly sensed i wanted to to ask something.

"Well, i kind of want to be dominated" i said tamely and a little embarrassed.

"Oh you want to see mistress Maddison do you?" she asked with a naughty edge to her question.

"Yes" i replied quietly.

"Yes what?" she fired at me sharply, in a big shift from her previous seductive tone.

"Yes....mistress?" i replied quizzically. There was a long pause before she finally broke her silence.

"I think i am going to have a lot of fun breaking in a new pet. Keep your phone handy and I will text you the address details and some further instructions" she stated before abruptly hanging up.

"Fuck" i said out loud wondering what on earth i was getting myself into. Was i really going to go and meet this big black transvestite and pay her to do what ever she wanted with me?.

I spent the rest of the day really on edge and considered cancelling but i also found myself checking my phone every 5 minutes hoping she would message me, what was i doing!.

As it got to 7pm i decided to have a nice cold shower and try and calm down my nerves and the raging erection i had been sporting all day. I thew on a black pair of jeans and a grey t-shirt when i heard my phone ping, the message was from Maddison.

"Room 212 at the county hotel. The door will be open, close it behind you and leave the money on the table and then take off your clothes and get on your knees xxx" her message read.

My heart raced, was i really going to go through with this?. I started typing a reply to cancel my booking as my phone quickly pinged again, this time it was a video file.

Maddison had sent me a video of her big, glorious cock, and then all of a sudden a man got between her legs and took her black monster in his mouth.

"Oh yeah, you like sucking your mistresses cock don't you" she said to him, a statement rather than a question.

"Yes mistress" he replied before greedily sucking her cock back into his mouth. The poor guy struggled to get even half oh her length down his throat before he slowly started to bob his head up and down.

"Tell mistress how much you love sucking her dick, you pathetic little fucker" she said as she was clearly enjoying the humiliation she was dishing out.

He made a slurping sound as he reluctantly removed his mouth from her rock hard cock. This was the first time i had seen it fully hard and my god it was a monster, easily 9 inches and thick.

"I love sucking your dick mistress Maddison" the bloke responded, his cheeks red with embarrassment but not taking his eyes off her big black sceptre.

Maddison then gave him a few firm slaps around the cheeks before taking grabbing the back of his hair and pulling his head down, impaling his throat on her cock. His eyes almost bugged out of his head as it filled his throat before he started to gag and his eyes filled with water.

The short video clip ended and i found that i had held my breath the entire time and my hands shaking slightly as my cock was now back at full mast and ready to explode. My phone pinged again, this time with another message.

"Reckon you can do any better? hahaha" her new message read.

My cock was raging, no way was i cancelling now. I had to see this out, so I quickly grabbed my keys and jumped in my car before racing to the hotel.

The 15 minute trip to the hotel car park was honestly a blur, i could have been speeding or hit something and i would have been none the wiser. I honestly had no recollection as my mind was completely fogged over by what i was about to do.

I walked the short trip from the hotel car park to the lobby and slipped into an empty elevator. I was so nervous that i felt that every set of eyes could see what i was here to do.

I hit the button for the second floor, taking a massive deep breath as the doors opened onto the floor and noticed that room 212 was down at the very end of the corridor, so i quietly tip toed towards my fate.

As i approached, the door was slightly ajar like she said it would. I took a deep breath and my hands trembled as i opened the door.

The inside of the hotel room was very basic, the curtains were drawn and the room was dimly lit with one lamp in the far corner. The smell was musty and had the obvious odour of sweat and sex.

As i scanned my eyes around the room, there was a generously sized double bed with two night stands either side. To the right just as i walked in, was a door that i assumed lead to the bathroom. I walked in further and saw a small table opposite the bed with a mirror attached to the wall but no sign of my tormentor.

Remembering my instructions, i took out my wallet and thumbed through my notes leaving the £120 tribute on the table. I found that there was a note on the table with a soft, satin blindfold next to it as i cast my eyes over the hastily scribbled instructions it contained.

"Take off your clothes and once you are naked, get on your knees and put this on" read the note.

I nervously removed all my clothes and placed them neatly folded on the table. I took one last long look in the mirror before putting the blindfold over my eyes and slowly sinking to my knees in darkness.

It felt like a long time but in reality was probably less than a minute before i heard a door open, slowly followed by the sound of heavy footsteps heading towards me. My heart felt like it was beating out of my chest as my hard on was so prominent that it almost ached.

I felt a strong, firm hand on my shoulders that traced around my back to my other shoulder, dragging long nails gently across my skin.

"You will do nicely" came the voice, in a sultry and seductive tone.

"And look at this, your cock is already saluting me, how cute" she mused, my erection not really giving me much room for denial at this point.

"Yes" i replied meekly.

"Yes what?, you little fucking slut" she said with a sudden sharpness as she grabbed my chin in one hand.

"Yes, i'm sorry mistress" I feebly replied.

"Much better. If you fail your simple instructions again then i will punish you, do you understand?" she asked.

"Yes Mistress, i understand" i felt her hands either side of my head as she whipped off the blindfold and i instinctively looked up.

"Did i fucking say you could look up?" she asked harshly with a slight smirk on her face that showed the relish that she had when men were on their knees in front of her.

"No mistress, i'm sorry mistress. May i please look up?" i pleaded.

"Much better, now you may look up at me" she proclaimed.

As my eyes adjusted, i got my first view of my dark skinned tormentor and fuck me was she beautiful. The pictures did not do her size justice at all, she was enormous and impossibly tall. Maddison was wearing the same blonde wig and heavy make up she had in her pictures and as i looked her over, she was almost entirely naked apart from a small black bra and the smallest high waist g-string that i had ever seen.

"So tell me my little slave, do you like what you see?" she asked me.

"Yes mistress, you are beautiful" i said, trembling with a mix of fear and excitement.

She was also wearing 4 inch heels so that she was easily standing at 6 feet 5, absolutely towering over me. She turned her back to me like she was showing off on a cat walk and thats when i saw her giant ass close up for the first time.

Each one of her ass cheeks were easily twice the size of my head and between them they hungrily devoured the g-string she had on. Her legs were thick, smooth and toned with thighs that looked like they could crush a watermelon.

As she completed her 360 degree turn, i saw the enormous anaconda she had stuffed in her g-string. Even fully soft it was bulging against the thin material, ready to get out and devour its prey.

"Tell me slut, what do you like about your mistress" she demanded, firmly.

"I love your ass mistress, its amazing" as i said it she smirked again.

"Well my little ass slave, i think il give you a personal introduction. Stand up!" she demanded. i struggled nervously to my feet as she handed me a small bottle.

"Your going to be my dirty little oil boy. I want you to rub oil all over my body, do not miss a spot and make sure you are over generous applying it to my arse" she instructed.

I popped the cap and squeezed the babyoil into my hand to warm it up and began slowly working it in as she stood towering over me. Her skin was so smooth yet impossibly firm at the same time, i felt her eyes burning into me as she watched me explore her body.

As i got to her ass i emptied another handful of oil into my hand and slowly began to massage the massive cheeks. Her ass was so soft and fleshy in my hands, it jiggled and moved as i worked as much baby oil into every recess as i could.

"If you ever need a new job, i'd definitely consider you as my little oil bitch" she stated as i felt a weird sense of pride at her statement.

She suddenly leaned forward and started to passionately kiss me, her lips smashing against mine and her tongue invading my mouth at will. I was powerless to stop the onslaught this amazonian was inflicting on me as she simultaneously trapped my throbbing cock in her crushing thighs while her mouth assaulted mine.

I couldn't move and she knew it, she had me locked in place, my cock held in a vice like grip between her thighs and her hardening bulge digging against my stomach. She suddenly wrapped her big arms around me as she started aggressively mauling my ass, digging her nails in while her mouth continued its assault on mine.

All of a sudden let released me from her passionate embrace. I must have looked shell-shocked as she simply laughed at me and pushed both of her hands into my chest as i fell backwards on to the bed.

"Lay there, don't move and do not touch yourself unless i say so. Do you understand me?" she instructed firmly.

"Yes mistress, i understand" i said swallowing hard, as i saw her walk around to where my head was positioned at the end of the bed.

As i looked up, i saw her massive black arse hover ominously above my head as she backed up so she was stood directly above me with my head between her legs when all of a sudden my world went dark.

Without warning, mistress Maddison had just sat firmly and full weight on my face. Everything was dark and warm as i felt the immense pressure from above as my head was pulverised into the mattress. Her well oiled arse slid effortlessly down on to my face, engulfing my entire head with little effort.

"I could tell you were a little ass loving slut the minute i saw you" she stated as i felt her adjust her weight slightly so that my nose was now fully embedded deep in her ass crack.

"I want you to take a deep breath through your nose and tell me how beautiful it smells" she demanded in soft tone.

I tried to inhale through my nose as best as i could and the smell was intoxicating. My nose pressed hard against the thin material of her her thong embedded against her hole. Her scent was strong but not over bearing, musky with secondary smell from the baby oil i had lavishly applied.

"You smell amazing, mistress" i mumbled out from under her, barely able to get my words out. If she adjusted her weight back slightly then she would cover it entirely.

"You are such a pathetic loser aren't you?. I bet you love sniffing big asses in your spare time you dirty little pervert" she mocked.

Before i could reply she slid slightly further back, her well oiled crevice offering no friction against my pummelled face. Her sweet asshole was now covering my mouth and i found my self completely sealed and airtight. As i tried to speak i merely made vibrating sounds against the fleshy prison i now found myself in.