tagTransgender & CrossdressersThe Role Players Pt. 07

The Role Players Pt. 07


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.



Based on everything that had happened in the past two days, I'd found a level of happiness which surpassed any I might have imagined in the past. Life however has a way of reminding us that the only constant in it is change. When I awoke the next morning, I expected to find Abby beside me but instead the bed was empty and by the time I got up to the tenth floor, her mother and her were already in what I guess would be Abby's new office, hard at work.

I had mixed feelings, seeing the young woman so absorbed in whatever it was that Andrea was explaining to her. At the moment I gave them their space, hoping that when the time came, she would need my help, in one way or another. Looking back, I wonder now what I could have done differently that might have saved my lover the pain and frustration which was yet to come.

The pattern continued over the next few days, Abby spending most of her time in the office, the look on her face so different from the carefree and impetuous one I had grown accustomed to. I would go in occasionally, hoping to either distract her or to see if I might assist, but her concentration was solely focused on the company now. I had never been jealous of an inanimate object before but I learned such a thing is indeed possible. The evening hours would grow late, and even when she finally would come to bed, I knew her mind was elsewhere.

I'd never had a real relationship before so when I look back now I know I should have been the one who took control. But, when you've been a submissive individual all your life, it's not easy to believe you're capable of taking such action. So, I kept my silence, hoping that the crash course in business that Abby was immersed in would soon end, and that things might return to a semblance of order. It was foolish of me to have thought that way.

The one bright spot in all of this was Thursday's arrival and my next assignment. Unfortunately even it was dampened a bit by Abby announcing to all of us that she was removing herself from play. She told us while the transition from the parent to her child was taking place, she needed to focus on one thing only. The only exception to that rule was yet another command performance by our silent partner, scheduled for six days away. This time Batgirl wasn't to be needed. He had decided to play his own part, Harley meeting his version of the nefarious lunatic, The Joker.

As for me, I would see not one, but two familiar faces that Saturday evening. Samantha Collins had returned and the second of our engagements would now include Antonio. When I heard that, I felt the first real smile I had enjoyed that week come to my face. He was as always at his most charming, reading through the script, his eyes with a lovely gleam to them. Once again though, my enthusiasm waned as it hurt to see that unlike Andrea, Abby wasn't going to be as hands on as her mother had been. She was nowhere to be seen by the time we finished.



After the changes have been made to Holly, Ms. Collins continues to toy with her life, using the submissive gurl not only as her own maid but now in a rather degrading role within one of the companies that she owned.

That Saturday night when the curtain came up, I sat, taking dictation as Samantha concluded a business deal with Antoine. I had a feeling I knew where this was leading to but it was fun to at least have something to take my mind off the events of the week. I was more than happy to play along.

My normal bust line was anything but as I'd added considerable size thanks to the new forms which were as she had stated, 38D in size. My makeup was much more pronounced, fairly screaming harlot. I sported not only the beauty mark on my cheek she had requested but also a rather baroque design on my lower back. That vision would make its appearance in act two.

"So, do you have any questions or concerns about the contract Antoine?"

The handsome gentleman sitting across from the older woman who was portraying her position of CEO seemed to have his attention focused elsewhere. His eyes constantly having flickered between the powerful businesswoman and the young lady seated nearby. I was dressed in business attire, thought the skirt I wore was far too short and probably inappropriate for the office, but not for the real position I held.

"No, no questions, but I'm wondering if you might have something to, shall we say, sweeten the deal before I sign Ms. Collins?

It was stated rather obviously, his eyes and attention fully directed my way as I heard my owner say. "Why of course Antoine. Holly, why don't you show this gentleman how very much we desire his business."

I stood up, putting down my writing pad and pen, before calmly walking over to kneel directly in front of the extremely handsome client. His eyes remained fixed on mine as I looked up, while reaching to slide down the zipper on his pants, my innocent eyes showing my complete submission to him. His grew in intensity when I freed him and without a moments pause, allowed my tongue to snake out to capture a drop of pre-cum, before taking him deeply into my mouth.

Before, I had only had a chance to taste the outside of the troupes lady killer. Now, I had it all, and what I truly wanted was to please this man in so many ways. From the moment our paths had crossed until right now, my body had fairly screamed for him, and tonight I would give him freely whatever he demanded of me. It was the perfect evening to carry me away from the week that had just passed.

I made sure I didn't lose eye contact, wanting him to see my subservience, knowing that it would make him feel empowered and let me enjoy the position I knew I always had desired. His hands found my hair, his fingers running through it as he urged me on. Words weren't necessary, actions were now speaking much louder than them, as I put my hands behind my back. It forced him to take control, a bit of a wicked smile showing on his face.

I sensed out of the corner of my eyes, the woman who originally had been my first client, as she moved to stand over both of us. I broke the contact that I had with him in order to look up at her, seeing the look of pure triumph on her face, as her words rained down on me. "Holly is a very unique gurl Antoine. I've molded her into what she is today. A slut with an insatiable appetite for anyone I tell her to desire. She will obey me, and at the moment you, so...enjoy."

I guess that had been their secret phrase they had agreed on as his movements became more urgent, his hands in my hair now holding tight, forcing me to take him deeper and deeper as I moaned in my surrender. Once again I turned my attention his way, only to see his eyes now shining brightly, the look on his face one of lust as his smile turned into a look of pure decadence.

The dance went on and on until I felt him begin to shudder, quickly pulling free of me, as I gasped for air. A steady stream of cum, hitting my forehead, the first of many as he marked me as only a man can. I felt the hot, sticky substance begin to slowly travel down my face before making its way onto my blouse and even my skirt. By the time it was over, it was quite evident what I had done. It made it all too clear that when I would walk back through the imaginary office to the steno pool, all of those present would know what i was.

My task wasn't finished yet. I didn't need to be told as I felt the gentleman begin to relax, how I should react. I cleaned him thoroughly, not wanting to waste a single precious drop, as finally his clothing was back in order. Walking over to the desk, he quickly scribbled his name on the paper, handing it over to his new business partner, who favored him with a smile.

"Excellent. I think we should celebrate tonight Antoine. Holly will cook for both of us and when the meal is finished, I'm sure she can think of another way to show my companies appreciation for our joint venture. Holly, make sure this gentleman gets my address before he leaves us and then you should go home and start preparations. You are dismissed."

"Yes Ms. Collins."

I rose, walking over to where a rather small desk awaited. The lothario followed, and as I leaned over to write down the imaginary information, I felt his hand reach up under my extremely short skirt. For a second time I gasped as his hand took liberties, his body bent over mine, his words throaty in my ear. "You will scream your passion for me tonight mon petite. I will make you feel every inch the woman you are, and when I am done, you will cry for more."

Turning, I held out the paper with trembling fingers, only for him to pull me into an embrace. The kiss was more a demand, his mouth devouring my own and I couldn't help but stagger by the time it ended. I had to hold on to the table, fearful my legs would not support me, as I saw the rather wanton look in his eyes and the mischievous smile on his face as he left. The curtain fell and on unsteady limbs I made my way back to my dressing room, the transformation from business woman to maid, needing to take place.

It was roughly thirty minutes later that act two began. I walked into the dining room only to see the two others already in place, each of them at the heads of the respective table. I served the lady of the house first, then made my way to the gentleman, who seemed to be admiring my rather considerable...assets. His hand again reaching underneath my skirt, finding the lace he seemed to love to caress. I fought to keep quiet, not wanting to alert my owner as to what was happening. It was all an act I know, but still I had my part to play.

Finally, I returned to the kitchen, giving them time to eat, and I found my mind wandering. I wondered if Abby might be watching, hopefully enjoying. Instead, I had a feeling she was still toiling behind the desk and I felt the good mood I had been in begin to slowly subside. I felt like I was losing the one thing I had spent my entire life searching for and it just wasn't fair.

When the stage manager gave me the signal that it was time for me to return, I literally had to force myself to make my way back out into the room. My face was almost a blank, not trusting myself, nor my emotions, to not overwhelm me. If so, I would ruin the evening for the woman who luckily was speaking to the gentleman seated at the table. He saw me approach, sensing immediately, something was wrong.

He used his body to block Samantha's vision, his eyes looking directly into mine as I heard him say, "Dinner was delicious young lady, but I expect desert will be far superior." His kiss began like the first one we had shared, a simple meeting of the lips, before he allowed his hands to take me by the hips, pulling me in even closer. I heard his whisper as he nibbled gently on my earlobe say, "You are sad my dear. I beg you to forget everything and let me bring a smile to that lovely face."

I couldn't help it as his kiss now went to my neck before once again claiming my lips. I swooned into his arms as his tongue danced with mine until, as he had the other time, he broke it off. It left me quivering and he took the moment to seize full control. My dress was unzipped, pooling on the floor as he turned from gentleman to scoundrel, roughly pulling my panties down as he pushed me onto the table. My hands landed on it as he used his own spit as lubricant and seconds later I cried out in pure joy as he buried himself deep within me.

His hands pulled my hair, his body weighing me down, as my head was forced to look directly into my Mistress's eyes. Hers shone with delight as the man began to take what he wanted, demanding my body pleasure him and I obeyed his command. I moaned, my own desire running rampant as I felt the hard confines of the metal cage press against my flesh, refusing the erection which was screaming to be set free. Samantha had made sure that it would be included in my changes that she requested done to my body. I knew even as he was ravaging my body, Antoine could clearly see the ornate henna butterfly on my lower back. The words proclaiming Property of Mistress S.

When I felt his body begin to lag for the second time that evening, I couldn't help the smile that played on my lips, knowing finally I would have what I had wanted from the first time I had laid eyes upon my fellow Player. He cried out his passion as he filled me and I took all he had until slowly I felt him begin to withdraw. I whimpered as he finally freed me, my body still pressed down to the table, my eyes still showing my surrender to the woman whose name I bore.

By the time the evening had drawn to its conclusion, I waited in the common room only to see Antoine walking toward me, a frown showing on his face. I started to ask him what was wrong but I already had an inkling. "I will not lie Holly. I miss the subtle touches that Andrea brought to the position your current lover does. I asked her if she enjoyed the performance and it was obvious she had not seen or given it any consideration. When I told her that it might help if perhaps she were to show a bit more attention to her cast she reminded me that when she desired my opinion, she would give it to me."

He handed me my earnings, taking a moment for a hug, and a very sweet kiss before leaving. I started to walk directly to the office, to talk to Abby, to plead with her to stop this madness. Instead, I turned and made my way over to the elevator. I was suddenly exhausted, only wanting a shower and my bed, even if it would be lonely without the woman I had once thought to be there for me always.

When I finally lay down, I tossed and turned, hopefully waiting on Abby to walk through the door but finally I surrendered to my bodies demand for rest. When I awoke, I saw by the clock that it was three in the morning, but I still was alone. Slipping on my cover up, I walked down the hallway, only to hear the sound of someone crying softly. There was minimal lighting, only that from the kitchen, allowing me to see the figure who was sitting on the floor. Next to her, an almost empty wine bottle in hand, no glass to be seen.


She looked up and to my horror, she looked like she had battered and bruised, except this was from emotional pain not physical. Her eyes were bloodshot, her face stricken with a look of almost desperation, as her voice belayed the torment she was feeling. "I...I can't do this." I knelt down beside her and it broke my heart to see her this way. She stared right through me and at that moment I think I knew how Renee felt when she had found me in basically the same position weeks before. I waited patiently, giving her time, allowing her to continue when the time was right.

"I tried but I can't. Every time I think I might be taking one step forward, it's like a hand reaches out and drags me back two feet. There's so much to do and not enough time in the day to get it done. The problem is my mother always made it look so effortless and I took her and that for granted. Looking back, I used to think in order for this company to be successful all we had to do was perform, and everything else would take care of itself. I was an idiot."

I started to reach out to pull her into my arms, to console her, but something told me that right now wasn't the time. She took a final drink from the now empty bottle only to say, "My mother was a showgirl. My father left before I was born and she raised me all by herself in Las Vegas. I used to think there was nobody as pretty as my mom and that she should be the star of the show. Instead, she put all her time and effort into raising me and then in building this company. If it was only me here right now, I would simply walk away. But if I do, then I've failed her, and she never failed me."

"My mom deserves to be happy. She put her life on hold to give me a chance at doing the same. The sad things is earlier tonight, just for a brief moment, I hated her for asking me to do this. I hated Felicity for coming into our lives right when things were coming together for you and me. It didn't last long, maybe a few minutes, but I was so ashamed of myself. So I got a bottle out, and hoped I could drink away the pain, but it's not helping. Right now, I feel like the understudy in a play who steps into the spotlight only to realize, she can't remember any of her lines. I feel lost...Holly."

Now was the time. I pulled her into my arms and felt her let go. I rocked her gently, probably like the incredible woman she had talked about had, many a year ago. By the time she was finished, it took all I had to get her into bed and she was asleep before her head hit the pillow. Looking down at her, I wanted to curse and scream at the injustice of the world. How when one person finds happiness, it's always another who seems to take their sorrow. I made a decision at that moment that I was having no part of that.

As the morning hours and the coming light drew near, I was hard at work on my tablet. Jotting down notes, suggestions and ideas. By the time I felt it appropriate, I sent a quick text to Andrea, asking her to meet me in her kitchen. By the time I got there I had almost worked myself up into a rant only to walk inside and as if in unison we said, "Abby."

In the past we would have both laughed, but at this moment, it didn't seem to be the right thing to do. I sat down across from her as she took a sip of coffee before beginning to speak. "I've been greedy Holly. I've found something I haven't had for more years than I care to count and I've let it consume me. I justified my actions because it was my time. I'd worked hard and I deserved it. Now, I'm beginning to wonder. Abby is in over her head and if I tell her I'm taking it all back, I'm afraid it will devastate her. And, I can't help but worry what Felicity will think if my time with her is as limited as yours has been with my daughter. I fear I'm in a quandry."

Now, I saw yet another family resemblance. Andrea's face masking her daughters, the pain on it giving me pause to think. Taking a deep breath, I looked down at the electronic device in my hand before saying, "Andrea, in the past I've trusted both you and Abby time and time again and both of you have rewarded that by helping me in more ways than I can ever thank or repay you. Right now though, I have to ask you to do the same with me."

Her look never wavered, nor her voice. "I've always trusted you Holly. At the moment you hold the key to my daughter's heart, and if that isn't trust, then I don't know what is."

Those words gave me the confidence to say, "Stephen is scheduled to be here on Wednesday to play with Abby. Can you please contact him and ask if he can come in a day early, that you and I need to meet with him concerning a matter of great importance. If you have to, tell him it involves Abby. I have a funny feeling he'll make time if he knows that she's involved."

She didn't question me, didn't even pause for a moment, before pulling out her phone and dialing. I stepped out of the room to give her time to make the call as my mind ran rampant, thinking about what I'd just done. Sitting down on the couch, I added a few things to my ever growing list. By the time Andrea had finished her call, I was mentally working my way through my notes only to hear, "Stephen is already in town, or at least near it. He's staying in the penthouse at The Ritz-Carlton in Lake Tahoe. His administrative assistant is going to try and schedule some time for us possibly later today."

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byhollygurl29© 3 comments/ 3249 views/ 7 favorites

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