Big Black Transvestite Mistress Ch. 02

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Back again to serve my mistress...and her friend!
10.1k words
4.76
16.6k
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Part 2 of the 3 part series

Updated 06/11/2023
Created 04/09/2022
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Cocksman85
Cocksman85
126 Followers

As i opened my eyes from the deep sleep i was in, i groaned out loud as my body ached everywhere. Just a little reminder, the previous day i had gotten so horny after accidentally watching some shemale porn that i began rapid downward spiral that ended in me paying a big black transvestite to dominate me. I still couldn't believe what i did yesterday, even more so that i couldn't believe how much i loved it!.

I stretched as i lay in bed churning over last night in my mind, my cock started to stir as i did. My face ached from from her sitting her big ass on my face, my knees were sore from kneeling and crawling on that coarse hotel carpet and my ass was a different story altogether.

My ass was still throbbing, and it still felt like it was on fire but my god was it worth it. Last night with Maddison had literally changed my sexual outlook on life and ever since i got home i couldn't stop thinking about her.

But her cock!, that magnificent veiny monster was the reason i could barely walk and had to sleep on my side all night after she had rearranged my insides. I was still tired as i had spent all night tossing and turning as i replayed the events in my mind over and over again. I knew she was joking about me being her slave as it was a job to her at the end of the day, but i found myself longing to see her again.

I woke up and made myself some breakfast before i had a nice hot shower, enjoying the soothing effect the hot water had on my aches and pains. I eventually sat down in front of my computer to crack on with my work as yesterdays 'activities' had put me behind schedule.

As the day slowly passed, i found myself struggling to find focus for any period of time as i tried to complete the website proposal that i was working on. I was constan constantly aroused as i kept thinking about being smothered by Maddison or imagining her fucking my brains out again. What was wrong with me?.

I needed some sexual release so i could focus soI opened my web browser to put some porn on that i could masturbate over (with a slight feeling of deja vu). I looked at my usual big tits and big ass searches and found an old favourite which had a nice curvy blonde woman with 38DD's getting fucked senseless in. I watched the scene unfold but i just wasn't feeling it, what was happening to me?.

Frustrated, I brought up Madisons escort profile and started to slowly stroke myself over her pictures as my cock swelled back into life. Looking at this enormous black tranny and imagining what i wanted her to do to me was the only thing getting me hot and bothered, why was the thought of being with this big black tranny the only thing getting me hard?. I continued to masturbate to her pictures, and soon felt myself nearing a shuddering orgasm when suddenly my phone vibrated next to me.

I frustratedly pulled up my pants and decided to read the message and i was shocked to see that it was from the woman who was currently haunting my sexual thoughts, Maddison!.

'Hello again slave, what are you doing at the moment?' the message from Maddison read.

My heart started to race, maybe she was serious about me being her slave after all. The thought filled me with dread and excitement in equal measure before i decided to be honest with my reply.

'Hi mistress, Im currently at home and just about to release myself' i clicked send and waited i minute before suddenly my phone started to ring, it was Maddison. I gulped and took a big breath to compose myself before answering.

"Hello, mistress" i answered, nervously.

"Is my little slave boy horny?" she asked teasingly.

"I'm so horny mistress, i keep thinking about you. Ive tried looking at my usual porn and it just isn't working" i told her truthfully.

"Oh baby, i'm afraid you will only be able to cum when when my big black cock is inside you from now on" she informed me with no hint of sarcasm.

"What do you mean mistress?" i said, a little taken aback by he comments.

"Baby you came while i was still inside you last night, that changes you i'm afraid. You're no longer straight, you are my little sissy cock whore" she stated matter of factly again.

"I'm still straight, mistress" i proclaimed but still referring to her as 'mistress'. I heard her laugh in response and my face started glowing red in frustration.

"Then what are you masturbating over right now?" she said almost knowingly as if she could see my computer screen. My anger seemed to dissipate, being replaced with embarrassment as i looked at her giant cock on my computer screen. I might as well be truthful, no need to deny it.

"I'm looking at your profile pictures mistress" i said with more embarrassment as i heard her laugh at me down the phone.

"You are such pathetic little sissy cock slut. Tell you what slave i am very horny myself so i want you to get over here now" she demanded, laughing as she spoke.

"But mistress, i" i started to respond, before she quickly cut me off.

"No need to pay any more either, since i've decided to take you on as my slave.

"Thank you" i said, confused.

Get over here now, same room as before and don't keep me waiting" she instructed before hanging straight up.

I was a little taken back by the conversation that had transpired. I definitely wasn't gay or anything but i couldn't deny that all i was thinking about was her magnificent cock. This also felt different, last night i had paid for a service and now this was all becoming very real. I shook these worries from my head as i quickly grabbed my car keys before once again racing down to the hotel, not wanting to disappoint her.

I arrived in the car park nearly 30 minutes later, traffic was a nightmare so it took longer than last night to get there. I started to feel a tightness in my stomach as i wondered what on earth she had in store for me this time. I walked at a brisk pace along the tiled floor of the hotel lobby to the elevator again, not looking up once.

I hoped that no one would recognise me from my twitchy behaviour on my visit yesterday. I tried to act as calm and collected as i could as i waited for the elevator to arrive. As the elevator door opened i walked in and pressed for the second floor and just as the door was closing i head someone shout.

"Hold the door please" a mans voice called out.

I used my foot to stop the door closing as two men and two women quickly scurried in. One of the women reached past me to press the button for the second floor before seeing that i had already pressed it.

"Ah you're going to the same floor as us" she mused, as i nodded lightly back at her.

"Are you here for the awards dinner later on as well?" one of the other men asked politely.

"No, i'm here to see.....a friend" i replied, nervously tripping over my words. I'm not sure that telling them i was here to get dominated by my big black transvestite mistress would have been wise.

"Have a nice evening" the other man said to me as the doors opened to the second floor.

The two couples left first as i loitered out behind them before dropping to one knee, pretending to tie my shoe lace as i watched them disappear down the hall and into their room, the colour drained from me as i saw that the room they had all entered was next door to Maddison's. As i heard and saw the door close i stood up and quietly made my way past towards room 212.

I reached Maddison's room and went to push the door open but unlike last night, the door was closed. I took a deep breath and knocked lightly as i waited a few seconds before the door opened.

"Come in" said Maddison's husky, sensual voice as she was hiding behind the door.

I walked in to the room, surveying the familiar surroundings. There was a big, open suitcase against the wall next to dressing table that wasn't there last night. The contents were strewn around it, skimpy thongs and countless other pieces of lingerie were showing. As i inspected it closer i saw several large dildos, butt plugs and ball gags along with various other fetish gear.

I continued to look around the room, the bed was unmade like someone had just woken up and the smell in the room was almost overwhelming. The strong, overwhelming smell of sweat and sex lingered in the air.

"Took your time, didn't you?" she asked me curtly.

"Im sorry mistress, the traffic was..." i started to reply before my voice trailed off as i turned around to catch my first look at Maddison. My jaw almost hit the floor as i watched her slowly stalking her way towards me.

Her ensemble left absolutely nothing to the imagination, this time she was wearing black knee high boots and as i traced my eyes upwards she was wearing a tiny red sling bikini. The over the shoulder straps barely covered her soft fleshy chest with her swollen nipples poking through the material and as i followed the thin straps back down to where they met in the middle at her crotch, my eyes nearly popped out of my head.

Her huge black member was stuffed inside the tiny covering as best she could, stretching it to breaking point as it spilled out of the top and sides while her huge, heavy balls were hanging freely below as there was no material left to keep them. The image before me was completely obscene and unreal as i found myself unable to take my eyes off her.

"I look fucking hot don't i?" she asked.

"Oh mistress, you look absolutely incredible" i stuttered back.

"Take off your clothes" she ordered, firmly.

I quickly removed my clothes and discarded them on the floor next to the open suitcase and got on my knees before my goddess without being asked.

"Good boy, i didn't even need to remind you" she praised, as i nodded politely in response.

"You are a quick learner slave." she told me.

"I just want to please you mistress" i responded.

"Would you do absolutely anything to please me?" she enquired, stopping inches away from me as my eyes drew a straight line to the massive cock and balls that was spilling out from her bikini.

"Yes mistress, anything". i said, probably not comprehending the scope of the word in that moment.

"Oh you are just the most obedient little slut now aren't you?" she chuckled.

"I try to mistress" i started before she cut me off.

"Last night i phoned up one of my girl friends to tell her about my new slave" she informed me before continuing.

"She absolutely loves submissive guys too, almost as much as i do. I told her about your impressive dick taking ability and she has decided that she wants to meet you so i have decided to whore you out" she stated.

"I don't know what to say mistress" i said stuttering, completely shocked.

"Now, are you going to be a good little whore?" she said as she walked past where i was kneeling and bent down to pick something out of the suitcase.

I got my first look of her magnificent large arse as she was bent down. The back of the sling bikini was wedged so deep between her cheeks that you almost couldn't see it. Her glorious ass cheeks jiggled as she stood back up and turned back towards me with something in each of her hands.

"I guess i can try mistress" i responded, still in disbelief.

"You will do better than try" she said sternly to me as she slid a familiar satin blindfold over my eyes.

My world was dark as i felt her move behind me as she suddenly grabbed my wrists and wrenched them behind my back. I suddenly felt cold steel around my wrists followed by a clicking sound as she secured my arms behind my back with what i surmised were handcuffs.

"But mistress" i started to protest before my mouth was stretched wide and filled with a thick object and i felt some straps around my head as she secured them at the back.

I was blind, unable to use my arms and unable to say anything as the ball gag was not secured tightly in place. I started to panic a little as i realised that i was completely at this woman's mercy, yet my cock was the hardest it had ever been.

"look how hard that pathetic cock is" she mocked.

I felt her breath on my face as i realised she must be crouching down in front of me as i felt her strong hand wrap around my cock as she began to slowly rub my cock back and forth as i let out a soft moan behind the gag.

"You will please my friend and do whatever we ask of you, ok?" she asked as i nodded eagerly in reply.

"Is he ready?" a new, deep yet sensual voice called out in the distance.

"Yes he's all ready babe" Maddison replied to the stranger.

I began to panic as there was now a third person in the room. The reality of my situation dawned on me as i realised there was now nothing i could do as Maddison released my cock from her hand and i felt her move backwards away from me. I was completely at the mercy of these two women.

"He looks gorgeous Maddy" the new voice added.

"Oh babe, i told you i wasn't lying. He is gorgeous and he will do what ever you want" Maddison replied.

I tried to say something but couldn't talk due to the ball gag, all that came out was a muffled sound as saliva started to drip from the corners of my mouth.

"I think he is trying to say something Maddy" the stranger said, her voice was deeper than Maddison's but still quite sexy.

"I bet he is wondering what you look like" Maddison replied to her friend.

I heard footsteps approach and a hand suddenly rested on my head, tapping their fingers in a steady rhythm.

"Is that right? you want to know what i look like?" the mystery voice asked me and all i could do was nod quickly in reply.

I felt someone move behind me as suddenly the blindfold was removed. It took me a few seconds for my eyes to adjust in this dimly lit hotel room but as i looked up i got my first look at the mystery woman.

She was transgender, which i had already guessed given her unique voice. She also wore a blonde wig and had ridiculous amounts of make on with bright red lipstick coating her plump lips. She was absolutely huge, not as tall as Maddison but still just over 6 feet tall and she was much, much thicker. Her body bulged out and made the purple mini dress she was wearing look like a second skin as it clung to her massive stomach and wide hips.

She also had a nice pair or chubby boobs as i checked out the obvious cleavage on display in her ludicrous mini dress. As my eyes continued down her thick, voluptuous body they stopped where her dress ended at the top of her thighs. Her legs were just as enormous and thick, like pale white tree trunks. She was wearing high heeled shoes to add to her towering stature.

"This is my friend Eve, she has travelled here this morning especially to meet you" Maddison's voice said from behind me.

Maddison grabbed my by the arm and pulled me to feet so i was now stood almost sandwiched between these two massive behemoths, the tiny filling in this massive tranny sandwich. They both moved closer, i felt something rest in my hands that were secured firmly behind my back. Maddison had made sure that her enormous, hardening bulge rested in my tied up hands as she started kissing my neck roughly, making sure i could feel her cock grow as she did.

Eve was stood in front, so close to me that my rock hard cock was poking against her pale white thigh, smearing a little pre cum that glistened on her pale leg. She leaned forward and started sucking and biting down on my nipples. I started to squirm as these two massive women attacked me with their mouths.

Maddison's hand was now roughly playing with my arse as she rubbed her index finger against my still sore hole as i started to flinch. Eve had removed her mouth from my nipples and was now crouched down in front of me so my cock was pointing directly at her face.

Without warning Eve lurched forward and almost inhaled my hard cock to the back of her throat. The feeling was incredible as she sucked my 6 inch cock better than anyone had ever sucked it before.

The vacuum like suction made my eyes roll and I started to moan knowing it wouldn't be long before i exploded in her mouth.

She was now sucking and slurping the full length of my cock, back and forth as she cradled my full balls with one hand and was rubbing her own crotch with the other. I was moaning loudly into the gag as i felt Maddison's index finger pop inside my rectum. She was making a beckoning motion, rubbing firmly against my prostate as Eve furiously continued to devour my cock.

Just as i felt myself nearing the point of no return, they both stopped suddenly and

backed away from me. I stood between them almost trembling as my wet cock started twitching uncontrollably having been brought to the edge of orgasm only to be denied.

"Now, now slave, you didn't think that we brought you over to please you did you?" Maddison said mockingly as i groaned in frustration through the gag.

The gag was starting make my face ache with my mouth stretched wide and the leather straps chaffing at the side of my mouth.

"I'l take this off because we are going to need your mouth now i'm afraid" Maddison casually informed me as she undid the gag and discarded it back into the open suitcase beside us.

"Thank you mistress" i replied as i stretched and moved my aching jaw.

"He's all yours" Maddison said to her friend as she moved in front of me allowing me to see her for the first time since i had the blindfold off.

Her enormous black cock was now free from the confines of her tiny sling bikini and was pointing angrily at me.

"Thanks Maddy" Eve replied licking her lips like i was a nice juicy steak she was about to tuck in to.

Eve slowly slid the straps of her purple mini dress down her shoulder as she started to slowly wiggle her body to manoeuvre the skin tight garment down her thick body. As she dress was pulled further and further down she revealed more of her thick, voluptuous frame. She did indeed have natural boobs, as they the flopped out in front of me. Her boobs were a decent B cup like i guessed and they looked nice and soft with plump, erect nipples.

As the dress was moved down to her waist, her full torso was now on display. She had a large round stomach and thick wide womanly hips to match, a true BBW in every sense. The dress had now started to fall down her enormous thick legs, her thick thighs were smashed together as she stood and she was wearing a mesh, purple high waist thong that came up over and covered the bottom of her belly and showed off her legs and waist beautifully.

As i stared at the mesh front of her thong, i managed to get my first look at her cock. It was poking out against the material and although it was difficult to judge her size it was probably around around or 6 or 7 meaty inches.

With her dress now off she stepped out of it fully naked apart from her thong and high heels. Maddison was still stood next to her friend and still wearing her ridiculously tiny bikini while slowly stroking her own 9 inch anaconda.

Eve stepped forward towards me hooking her thong to one side and giving me a clear, unobstructed view of her cock for the first time. It was circumcised like Maddison's but no where near as long, hers was indeed about 6 or 7 inches but my god it was thick.

She pointed her thick, chunky member at my face as i instinctively opened my mouth to accommodate her. Her cock stretched my mouth as wide as that ball gag had done earlier if not more so as i felt it fill me. Her cock was nearly as thick as my forearm and my eyes started to water as she forced her entire length in my mouth.

"Oh Maddy, you weren't lying, this whore can handle cock alright" Eve commentated to her friend.

"I told you babe, he will do anything you want" Maddison responded as she was now aggressively masturbating to the sight of her friend getting her dick sucked by her slave.

I tried to focus on the task at hand but was finding it difficult with my arms restrained. I had no control over the thick, pulsating monster i was completely at her mercy. Eve suddenly grabbed my head and started to slide her cock back out of my mouth before violently forcing it back in. I started to gag and heave, fearing that i would vomit if she continued. I tried to relax my throat and breath calmly through my nose as Eve picked up pace with her aggressive skull fucking.

Cocksman85
Cocksman85
126 Followers