tagTransgender & CrossdressersThe Role Players Pt. 08 Ch. 02

The Role Players Pt. 08 Ch. 02

byhollygurl29©

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21.

This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy.

The main characters in this tale are as follows:

Eric/Holly a 23 year old male who fantasizes about crossdressing, precisely as a submissive maid.

Abagail/Abby a 22 year old female who works as one of the role players.

Andrea/Abby's mother a 41 year old female who owns the company who moves in next door to Eric.

If you choose to read this tale then I thank you in advance for doing so. When you have finished I hope you will leave a comment or a suggestion and I would ask that you please vote as well.

Holly


*****

April approached me cautiously as I sighed, closing my eyes as I tried to relax before saying, "So, did anyone tell you anything about tonight?"

"No Miss Holly, there has been great secrecy concerning this evening. There is a lock on the wardrobe door and I was told that eventually Miss Andrea would come down to unlock it. Until then, why don't we get started?"

Her idea of starting was to as always begin to soothe me with her gentle touch and her words which quickly pulled me under. It was only then that she placed a call to her friend and shortly later Andrea did indeed join her.

I'm not sure how much time had transpired when April brought me back but when she did I could have easily have panicked. Luckily, the lovely woman who had given me such confidence held one hand while Andrea held the other. The problem was that when I opened my eyes it was to total darkness. They both squeezed my hands to let me know I wasn't alone as the new CEO spoke.

"Both April and I are here with you Holly. You are safe, okay?"

I nodded, a bit unsure, as she went on to say, "This is all part of the scenario for tonight luv and once again, as we've talked about in the past, you're going to have to trust me. I'm going to tell you what I can and guide you up until the moment it all begins. I know you have questions but I'm afraid I can only tell you so much. I've made my own deal with the devil and I fear you'll have to pay the price."

I felt my heartbeat escalate as I sat there, the familiar tremble threatening to return. "April and I will be assisting you in dressing Holly but before we do let me share what I'm allowed. Mr. Lyon's as you know is a very prideful man. He feels you challenged him by testing his abilities in assisting Abby while in the process you helped put the company on a path which will guarantee its success. Now, through my own fault, he's challenging you."

"When we sat down to write this scenario, he, Abby and I were talking and I couldn't help but brag about how you did some of your finest work when you had only your mind and your body to rely upon. I compared you to a trapeze walker who worked without a net, no visible means of safety at your disposal. So, now he's decided to challenge you, just as he felt you did him."

"You will not know anything about the scene until the blindfold is removed at which time you will see words which will be seen simultaneously by the members who are in attendance. The conversation on the screen will be between you and an unknown individual who you will then meet shortly. Once the exchange between both of you comes to an end, you will walk out onto the stage, and from that moment on you will only have your wits and your physical attributes at your disposal. The only thing I can tell you is that I urge you to do precisely as I did in the text I sent you a few weeks ago. Follow the lead."

I started to open my mouth to speak only to hear, "I'm sorry Holly. I cannot answer any questions, I've already said too much."

So, as the time passed, I found myself being dressed like an invalid, two pairs of hands assisting me. I felt fabrics against my body and sensed this wasn't my traditional maid's uniform but other than that I was at a complete loss. I felt a rather cumbersome item being put around me, the weight against my shoulders as a pair of hands fastened a clasp near the neckline of the garment before both my handlers led me blindly out the door. From there we went into the elevator and up to one of the newly renovated floors where the play would take place.

When we seemed to be in position I felt one of the hands which had guided me give a gentle squeeze and then release me. Heels echoed, as Andrea I believe walked away, until I stood there with only one guide remaining. Her voice brought about a sense of calm, all part of not only the message she had shared with me many months ago, but also reminding me of her kind and gentle ways.

"Beautiful gurl, I know much is being asked of you. I too am restricted in what I can say but I am not limited in telling my friend how I feel. I have watched you become more than the flower who blossomed into such beauty which radiates from both inside and outside. You have grown into an amazing woman. One who has shown the world that by putting others first, even when it might mean possibly sacrificing our own needs, we bring out the best in ourselves and become a shining example to others."

I didn't want to cry, fighting the tears as she went on to say, "Miss Andrea told you tonight to follow the lead but I might suggest following your heart. In it you will find every answer to any riddle, puzzle or scenario in life you will ever come to, including tonights." With that she gently pulled the blindfold from my face and as I blinked, trying to recover my vision, I saw her smile as she motioned toward the monitor where we stood just offstage.

HOLLY...TRUTH OR DARE?

WHO...WHO IS THIS?

WHO I AM IS NOT IMPORTANT AT THIS TIME. WHAT IS OF GREAT IMPORTANCE IS THE FACT THAT I KNOW MORE ABOUT YOU THAN YOU POSSIBLY KNOW OF YOURSELF. I'VE WATCHED YOU CLOSELY, SEEN HOW YOU SIT IN THE DARKNESS. TOO SHY, TIMID OR EVEN POSSIBLY FRIGHTENED TO DARE REALIZE YOUR OWN DREAMS WHILE OTHERS DO THEIRS. TONIGHT YOU HAVE AN OPPORTUNITY, A SINGLE CHANCE, TO CHANGE ALL THAT. IT MIGHT BE FOR ONE NIGHT OR IT COULD EVEN POSSIBLY BE FOR A LIFETIME BUT THAT WILL BE YOUR DECISION TO MAKE. FOR NOW, EITHER ANSWER OR I LEAVE, AND YOU WILL ALWAYS WONDER WHAT MIGHT HAVE BEEN. YOU HAVE FIVE SECONDS. TRUTH OR DARE?

TRUTH.

VERY WELL, I REQUIRE ONLY THE ABSOLUTE TRUTH. I DO NOT WISH TO HEAR A STANDARD SUBMISSIVE RESPONSE, SOMETHING FOUND IN A BOOK OR PERHAPS RESEARCHED ON THE INTERNET. I WANT TO HEAR THE ANSWER THAT COMES FROM YOUR SOUL. YOU HAVE ONLY ONE CHANCE. TELL ME HOLLY, WHAT IS IT YOU ARE REALLY SEARCHING FOR? YOU HAVE ONE MINUTE.

At this moment my heart was racing, the hand which held mine felt my nervousness, as I read such powerful and intoxicating words. I tried to peer onto the set but it was as black as the cowl I was wearing, hiding what was underneath. I looked at April but her attention was on the screen, and soon enough, words again began to appear.

I'M LOOKING FOR A DOMINANT WOMAN, SOMEONE WHO WILL CAPTURE ME TOTALLY. MY MIND, MY BODY, MY SOUL AND MY HEART. I WANT TO GIVE UP COMPLETE CONTROL TO HER. I'M AFRAID THOUGH THAT SHE DOESN'T EXIST.

AN EXCELLENT ANSWER. WELL WORDED AND OBVIOUSLY A PASSIONATE RESPONSE. VERY WELL, SINCE YOU PLAYED THE GAME WITH ME HOLLY I WILL TRY AND DO THE SAME FOR YOU. TRUTH OR DARE, WHICH DO YOU REQUIRE OF ME?

TRUTH.

ASK YOUR QUESTION THEN.

WHAT IS IT PRECISELY YOU ARE LOOKING FOR?

THAT'S NOT A DIFFICULT QUESTION TO ANSWER. I'M LOOKING FOR A VERY SPECIAL, VERY UNIQUE SUBMISSIVE. SOMEONE WHO TRULY WISHES TO EMBRACE THEIR POSITION, TO GROW WITH MY GUIDANCE AND FIND THAT DREAMS DO INDEED COME TRUE. I WANT THIS PERSON TO BE THE STANDARD UPON BY WHICH OTHER SUBMISSIVES WILL BE JUDGED IN THE FUTURE. NOW, IT'S MY TURN. TRUTH OR DARE HOLLY?

DARE.

VERY WELL, I DARE YOU TO BE THAT SUBMISSIVE. I DARE YOU TO STEP OUT FROM THE SHADOWS AND FIND ME WAITING. I DARE YOU TO TEST NOT ONLY ME BUT ALSO YOURSELF BY GIVING ME THAT CONTROL YOU SPOKE OF. I DARE YOU TO STEP FORTH...RIGHT NOW HOLLY...IF YOU DARE.

I felt the hand at my throat undoing the clasp, as the heavy coat like garment was pulled from my shoulders, and I stepped out from behind the curtain. The darkness was complete; the only light a single spotlight showing a figure that was waiting, all the way across the stage. It was only when I drew closer did I see a pair of familiar eyes focused on me, though her appearance belied any I had ever seen of her before.

The garment she wore was best described as a series of Lycra strips of clothing which crisscrossed her entire body. They went across the more strategic areas, hiding her secrets, while still almost allowing her total femininity to be easily seen. The material was only wide enough to cover her nipples, even the edges of her sex between her legs were barely covered, the sight beyond decadent. Her arms were covered by long shiny black lace and lamé gloves while the heels she wore left her towering over me. I could never have worn the almost five inch platforms which featured four buckle leg straps and laced up leg design. She looked every inch the dominant female she was portraying.

When I finally stopped before her, I saw a pair of eyes which bore dramatic makeup, smoky gray eyeshadow highlighting the cool blue orbs which seemed to stare right through me. Her hair was normally blonde but with the gel she wore it had been slicked back, giving her a predator like look. Now, I wasn't really playing a part as much as I was living it as I saw a table next to her, a quill pen and two documents awaiting either a signature or perhaps refusal. My eyes slowly lowered, taking in the sight of the all-white and lace garments which I wore. It was as if we were dressed specifically to show the contrast between the two separate sides of the lifestyle.

I had never seen Abby not only look like this but to speak in the manner she did. I had thought that her interpretation of Harley Quinn allowed her true personality to show forth but as the evening progressed, I wondered if like I had Stephen, I had underestimated my partner as well.

"You've taken a single step, now it's time to see if your words ring true gurl. The contract on the left grants me complete control over you and whatever might happen this evening. Depending upon whether or not you sign it, and if you conquer the obstacles I put in your path tonight, then we will consider the one on your right. Know this though, if you sign it, then your life will never be the same."

It was an ominous statement, as was the figure that slowly stood from the stool she had been sitting on. I tried not to move, but I could feel her exotic pull as she allowed her long nails to trail gently over my face. They dipped slowly, tracing my breasts, before moving down to almost tantalizingly touch the silk and lace which fell just below my hips. I could only stand there and shutter as she finally stood behind me only to say softly, "Read the contract carefully Holly. I want there to be no misunderstandings between us tonight. It's time to make your decision. Someone else said it best. Will it be fight or flight?"

I wasn't aware that as I read it, so did those in attendance. I couldn't see them though I could hear a rustling, whispered comments exchange as I viewed what looked to be a standard dominant/submissive pact. The theatre had been renovated so that with the curtains partitioning off certain areas, the video cameras that were currently airing the evening live over the World Wide Web were unobtrusive, not even visible to the naked eye. At the moment however, I was lost in the moment. There seemed to be only two us, me and the incredible vision that waited patiently, the pen in her hand held out to me.

When my trembling fingers touched hers it seemed to give off a spark as I gasped while she never took her eyes off me. I took the writing instrument, scribbling my name across it. Handing it back to her, she did the same, before turning it face down before saying, "Present yourself to your Mistress Holly."

I took the traditional pose, kneeling so that my legs were spread roughly six inches apart, my hands with the palms flat against the top of my thighs while my eyes lowered in my submission. I waited patiently, knowing that this was only the beginning, and I couldn't help but wonder what was going to happen. I found out soon enough.

"Tonight you will undergo a series of six separate tests. They will begin with the most simple, until come the final one, you will be challenged and your limits will be tested both mentally and physically. If at any time I feel you hesitate to follow one of my commands, or you tell me no, then this night will end. You will have failed me but more importantly, you will have failed yourself. This is not just about you gurl, this concerns both of us."

I remained in position, knowing words weren't required of me at this moment. I felt her hand reach down as she said, "Rise Holly." I did, accepting her assistance as she walked across the stage and I followed obediently. When she stopped, she turned, seeing how my eyes remained lowered, accepting her dominance as I heard, "When this door opens, I require you to kiss the individual who enters, male or female, it does not matter. I do not require an ordinary kiss Holly. I want you to ask them for their permission, telling them you are under my consideration and if they agree, I want your kiss to show them and me the passion you have kept hidden away inside of you. If this were to be the last kiss you would share during your time on earth, then let it be this one."

We stood almost side by side, the silence in the room absolute, the seconds ticking by as we waited and I wondered. Finally a second spotlight came on, a door was opened and out walked...Felicity. She was dressed in what many would call the little black dress. A modest look, though her face showed a touch of uncertainty as she entered, especially seeing how I approached her, my voice soft as I spoke my first words.

"M'lady, I am under consideration of this Mistress and she has challenged me with asking you for a kiss. Will you honor my potential owner and I by allowing it, please Miss?"

The look changed from one of puzzlement to one of delight as she moved in closer, taking me in her arms and we kissed. It might have begun with a simple touching of lips but it grew in intensity as I obeyed the beautiful dominant's request. Our tongues danced as one. Her hands took liberties, sliding down until she cupped my bottom, pulling me in closer, our bodies literally grinding against each other. By the time it had finished, both of us stood there, our eyes locked on each other, and I saw the look of pure lust in those beautiful sky like blue orbs.

It took several seconds but she remembered her part as she turned to Abby only to say, "If her body can deliver the promise that her lips offer, then you would be blessed to have such a beautiful and passionate submissive, Mistress Abby." She favored me with a slight smile before stepping toward backstage, the darkness quickly swallowing her. I moved obediently next to where the blonde beauty stood before walking across the stage to a table that awaited. There was an open wine bottle and two glasses waiting as she came to a stop.

She motioned toward the table and I took that as a cue that I should fill both glasses. I presented one to her and received a nod as she said, "The woman sitting across from us will be your second obstacle. You will explain to her that your Mistress sends the libation for her taste buds and you for her pleasure, in any way she deems it necessary."

I turned, a spotlight showing a well-known figure to me and as I walked her way, I saw the smile playing on Renee's face. I knelt, my eyes lowered, the wineglass held high as I spoke softly. "M'lady, my Mistress sends this drink for your enjoyment and I pray my presentation honors both her and you. She also asks if I might be of service in providing you with any form of pleasure that you might desire of me. How may I please be of service to you?"

She accepted the wine, taking a sip as from where I knelt, I saw her reach down and pull the slit on the full length skirt she wore to one side. The vision of her glistening sex against the lace of the garter belt and stockings she wore spoke volumes. Her eyes danced with delight and I eagerly obeyed, no words needed be spoken. I captured her sex, my tongue running from the bottom of her slit to the top as I shivered at the soft moan which escaped her lips. I felt another's presence, knowing that my Mistress for the evening, had drawn near.

Dr. Craig knew how much I loved to feel her hands in my hair as she took another sip of the white wine before positioning me, my mouth, my lips capturing her clit which already beat in harmony with her rapidly escalating heartbeat. The sounds which came forth, the combination of my efforts and the effect I was having on her filled the room with her unique fragrance, only the prequel to what I knew when the time came would be an explosive climax.

I wasn't disappointed as I felt her entire body shake and I closed my eyes as the scream, a combination of joy and pleasure of the highest order, ran rampant through her very being. The orgasm exploded forth, covering my entire face, and now it was my heart which smiled. I remembered how this incredible woman played such an important role in my news life. She had helped me embrace the happiness I had found, while helping my other half to finally be free of the constant torment which had tortured him, as surely as any dungeon implement might.

I knelt, knowing it would take the lovely therapist a few moments to regain a semblance of composure and when I saw her outstretched hand, I rose quickly, extending my arm so that she might have a bit of added support. She smiled her thanks as I saw Abby favor her with one of her own only to hear, "I thank you for the delicious beverage but the vintage pales in comparison to the talents of this young lady. Her years may be few but her talents more than do justice to her age. She is a treasure."

Abby gave her an approving nod and I got a soft kiss on the cheek and like Felicity had done, she disappeared into the folds of one of the curtains. Two tasks completed, four remaining. I knew she had promised they would grow in intensity but up till now they had involved nothing but my pleasure. That...was about to change.

I followed the black clad figure as she returned to her table, the wine bottle nowhere to be seen, a small box awaiting. She picked it up, turning only to extend it to me, her voice warmly saying, "For many a submissive there exists a fine line between pleasure and pain. If a dominant is to have the type of control you say that you desire, then I need to show you that I can provide you or deny you one or both. First, I shall deny. Take this to the gentleman and tell him I desire you to be put into chastity to show your acceptance of my control. Do so now Holly."

Turning with the box, I saw a man standing with his back to me. It was only when I stopped, presenting myself to him, did he turn as I said, "Sir, my Mistress asks if you will be kind enough to place me into chastity, so that my pleasure is no longer mine to control but now belongs to her."

My head was bowed, but when he spoke I knew immediately who it was. "Slut, directive thirty nine. I obeyed, seeing the face of the man who I knew as Lawrence and walking out from the shadows was the brown haired beauty who had come to our aid only recently. Halle's eyes sparkled, as she walked up to her Owner as he put the box down which held the cage and the lock inside.

Holly, you will stand."

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byhollygurl29© 9 comments/ 2850 views/ 9 favorites

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