tagTransgender & CrossdressersThe Role Players Pt. 08 Ch. 01

The Role Players Pt. 08 Ch. 01


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.



It was late that night before I made my way back down to my new surroundings. The rooms were mostly dark, a single light burning, but when I entered the bedroom I saw Abby stretched out on the bed. She was still in the same clothing she had worn to the meeting. Her hair was a mess, most of her makeup was now on her pillowcase, the blouse and skirt she wore were badly wrinkled and I don't think I'd ever seen anyone look more beautiful in my entire life.

I lay down beside her as she made a rather sleepy noise before gently rolling into my arms and I held on tight. For a brief second I saw her eyes open, struggling with her body so in need of rest, but she managed it long enough to give me a smile and to say those three little words. "Hey there beautiful." It was only a second or two later that she succumbed again to her slumber but it didn't matter. She was back.

It wasn't twelve hours, it was more like fourteen and when she awoke, she did so looking around like she was a bit lost, her mind still not quite awake. I'd been up for a short while, long enough to fix some of her magic elixir and I walked in with a steaming mug of coffee, sitting down beside her. "Morning sleepyhead," as she smiled, gratefully taking the mug from my hand and I enjoyed just being close to her, words not really being necessary.

By the time she had really woke up, she moved slowly into the bathroom, as I heard the shower running and gave her some privacy. It was almost an hour later that she walked out into the main room of the house where she found me sitting down on the floor, a warm smile on my face to see how she had exchanged her business clothing for her normal attire. I didn't have to worry about her struggling behind that desk and it felt like a giant weight had been lifted off my shoulders and I'm sure off hers.

She'd refilled her mug, taking a sip as I said, "So, have you given any thought to tomorrow night's meeting with the Joker?"

The look she gave me was mischievous at best, her words sounding more and more like the young woman I knew and loved. "Oh yeah. I need to talk to Mom so she can tell our majority partner I have two stipulations. First, if he wants to play, he's got to pay. I want her to double the quote. Second, I want to have complete control over the scenario. He may have won last night, but I promise, he's going to pay for it."

I bit down gently on my bottom lip, trying to think of how to say what I had in mind. "I know he was an ass Abby, but a lot of what he said made sense, I guess."

She sighed, nodding as she replied, "I know Holly. I guess I should be thanking him but at the moment all I want to do is wipe that smug look off his face. It's going to take some time and I need to find out how my mom feels about all of this. I hate to admit it but he was right, I made my decision based on my emotions but it seemed like the right thing to do. Either way, he called us show ponies and if he ever does that again, I'm going to get a riding crop and make that bastard gallop for me." We both laughed, the sound so pleasing to hear.

I had something else to talk to her about, but as it turned out, she was already ahead of me. "So, have you decided how you're going to decorate your new place yet?"

Shaking my head I answered her, hoping I could make her understand exactly how I felt. "No, I'm not going to decorate my new place." She looked at me with a confused look on her face as I continued softly, "I want us to decorate our new place Abby. I don't want to live down here all by myself. I don't want to go upstairs to see you. I want you here with me from now on, please?"

I saw her fighting not to smile, her face turning reminiscent of the look the last time I had seen Harley as she struggled to think. "I don't know. First, you snore. Second, you're not really my size so I can't borrow any of your new clothes and third, we're gonna need a bigger closet." Finally, she giggled and I joined in as my heart did something I didn't think was possible. It grew even happier.

By the time we had decided on a plan of action for doing some serious shopping, we had made our way down to the office floor. Andrea, Lydia and Stephen had their heads together but they all turned their attention our way as we walked hand in hand into the room. Stephen gave us a both a bit of a smile but Abby brushed him off as I had to fight not to smile back.

"Mom, can I talk to you for a minute, in private please?"

The two of them stepped out of the office and I was left with the new dynamic duo in the room. Stephen shook his head as I said to him, "Don't look at me. You're going to be the one who has to step into the lion's den tomorrow with her. Batgirl has had her wings clipped, she knows better than to mess with Harley right now. You do know you're in for it, right?"

Lydia laughed as Stephen rolled his eyes. "I believe I can more than hold my own with a woman who idolizes my character Holly. I should think you would have a bit more faith in my acting ability after yesterday's performance."

Walking over to Lydia, I whispered in her ear, telling her what Abby had shared with me. The look on her face was one of a shared secret and now it was her turn to say to her employer, "Holly's right, you really are in for it."

The billionaire threw up his hand, his face trying to look angry but failing while saying, "I pay you good money young lady to be my executive assistant, not to play a part in what is obviously a conspiracy against me." I had no idea how those words would prove to be so prophetic further down the line.

That afternoon Abby and I entered the building's address on the business card that Margaret had given me. Our eyes opening as wide as saucers seeing a space almost as large as our warehouse but filled with every imaginable item needed to furnish a home. I wasn't even aware of such a place, and even more so, how she had already made arrangements to have a personal shopper assist me.

The young woman who walked out from the office was the same age as both of us, her smile as pretty as she was. "Hi, I'm Meredith. Mrs. Collins has asked me to help you Holly with your selections." I introduced her to Abby and a few minutes later we were seated on a couch as she said, "I like to learn a bit about the people I'm helping. So, tell me about Holly and Abby."

I hadn't expected this but as we shared a bit about ourselves it showed me that she was taking the time to see what it is not only that we liked or disliked but establishing a rapport which seemed to be genuine. It was quite a difference from the norm but one that made the experience more enjoyable. By the time we had finished, she had a good idea of what to show us, the space being so large that it would easily be overwhelming to try and not get lost in it.

The first thing I noticed was there was no price tag on any of the items which made me a bit hesitant, something not lost on our hostess. "Holly, it's already been taken care of in advance. You and Abby just pick out what you want and that's all you have to worry about. Samantha already told me you might be a bit shy about making a purchase and that if so I was to furnish your space on my own. I have very expensive tastes I promise."

I must have looked a bit shocked as she laughed and Abby grinned and we began. It was a couple of hours later that we had found everything I was willing to pick out and I had a feeling based on Meredith's face there would be a few surprises coming as well. We didn't shake hands, we shared hugs as both of us made our way back to the warehouse.

The first person I saw when we entered was a very familiar face. Halle ran over, giving us both a hug as she said, "Wow, this Lyon's guy doesn't fool around. I've never ridden in a private plane before, I could get used to that."

I grinned at her saying, "Well, he's available and as beautiful as you are, how could he turn you down?" She laughed, twirling showing off her more than ample assets and our troupe grew by another.

Abby went to find her mom while I returned to the ninth floor, looking at the wide open space and trying to imagine the transformation which would take place of the coming days. I was walking around almost an hours later, picturing where this and that might go when Abby walked in, her face bearing a frown. I didn't even have time to ask, only to hear, "He agreed to everything. I went from $20,000 to $40,000 and mom said he didn't even bat an eyelash. Knowing him, he's probably got that much stuck behind the cushions in his couch."

I tried to stifle a grin, knowing full well he would pay a king's ransom just to be next to her. She sighed saying, "I guess I'm going to have to get my revenge while we're playing. Want to hear what I'm thinking about for the scene?" I nodded eagerly and by the time she had finished, I saw the look on her face was the same one I had seen on Harley's when she triumphantly stood over me.

"Wow, I'll say it backwards, wow." She grinned as we both made our way back to the office so Abby could get a burgundy folder and officially type out the scenario. The look on her face was almost gleeful and when she passed by her future victim, he looked a bit puzzled as she laughed hysterically. Like I had said, he was so in for it.

The next day we both went our separate ways, Abby to get prepared for her role that evening while I had a plot of my own to carry out. All this talk about this evening's scene had sparked a thought I had hidden away. They always said revenge was a dish best served cold but I wanted to heat things up a bit between both of us so I found my way down to wardrobe and located the items I would be needing.

Early that evening, I saw Lydia and as she walked towards me she asked, "So are you going to watch Harley and her boyfriend battle it out tonight Holly?"

I shook my head no saying, "Nope, I never was much for a those gory, bloody movies and I figure this one is going to make those look like Bambi."

She giggled and I did the same. "So tell me Lydia, have you ever seen one of our performances before?"

I added another one to my list as she blushed a bit, giving me a smile in the process. "I was with Stephen the night Harley took down Batgirl. It was quite...arousing."

Okay, now it was my turn for my face to turn red as she grinned. There was a bit of an underhanded reason I had asked and I shared it with her, a second secret she know knew as her eyes lit up. She pulled out her phone, put my number in it and then with a wave, walked away. I made my way into the office where Andrea was seated on one of the couches, wineglass in hand as I said, "Did Abby share the scene she wrote for tonight Andrea?"

The beautiful blonde rolled her eyes as she nodded yes. "I made my daughter promise me that Harley would not kill her boyfriend. She handled it better than I thought she would but I still think he's in for it." I was beginning to sense a theme.

That night, I was getting dressed and thinking about what was transpiring on one of our many stages down below. Abby had shared with me her unique vision of tonight's scene. How Harley was to bust the Joker out of Arkham Asylum but he was unaware she had been seduced by the woman known as Poison Ivy. She had used one of her potions to turn Harley against her boyfriend and while the villainesses mind was already warped, now she had not one, but two personalities inside of her. She would switch from one to the other without a seconds notice and I couldn't help but grin. One Harley psycho was something, two was...unimaginable.

By the time my phone went off I was more than ready. Everything was in place as I answered saying, "So, how did it go?"

Lydia sounded a bit flushed, her voice a bit more animated as she said, "Well, he doesn't seem to be bleeding but he is limping quite a bit. I do know this. He doesn't need his makeup anymore, the grin on his face now seems to be a permanent one." I laughed as she told me Abby should be heading my way shortly and I got in position.

It was a couple of minutes later that I heard the sound of the elevator door opening. Abby was still in full costume when she tiptoed quietly in, seeing the form under the covers, the clever job I had done to make it appear I was asleep. She walked right past where I was hiding behind the door as I pushed her in the back, a shriek escaping her lips as she hit the bed and I pounced on top of her. I quickly grabbed her wrists, putting a pair of bat cuffs on them, as I flipped her over.

Her eyes were wide, as she saw Batgirl had returned for her revenge. "You bitch, you left me for those guards to do whatever they wanted with me. Now, you're going to pay for that."

She slipped back into her role without a moment's pause saying, "Oh, hiya Babs, long time no see. No hard feelings, right?"

I grinned down at her behind my mask saying, "Oh, I'm going to give you something hard to feel but that comes later."

Pulling down her extremely thread worn shorts and panties I stopped, seeing she wasn't wearing any. My smile grew even wider. "My, oh my. Someone's been a very, very bad girl Harley."

She tried to give me her most innocent look. "What you gonna do Batsy? Spank me?"

I flipped her over as my hand began to do precisely that to her lovely heart shaped bottom. BAM! POW! SLAP! She screamed in fright before beginning to moan as I let my fingers play between the legs, finding exactly what I thought I would.

I returned her to her previous position, seeing the wanton look in her eyes, as I dove between her legs and enjoyed my feast. It was obvious someone had gotten lucky as I tasted two distinct flavors, the most delectable of treats as she was helpless to stop me. I drove her body wild, as she thrashed on the bed, and I was spurred on by her cries of delight. As she had when we had last played, every orgasm brought forth her manic laughter, until finally Batgirl had won.

By the time it was over, I held her in my arms, the only remaining part of her costume were her pig tails she wore and the smile on her face as I gently kissed her on the forehead. It didn't take long until I heard the soft sound of her regular breathing and I knew she was asleep. It was the end of many wonderful days that would follow for the next two weeks but soon enough it was time to get back down to business.

The entire troupe, cast and crew, were on one of the newly renovated sets early Friday evening when Andrea, Stephen and Lydia made their appearance. It was Andrea who spoke to us saying, "I hope everyone enjoyed their time away but we have a very important performance for tomorrow night to discuss. We will have approximately one hundred members of the club in attendance and many more watching via the internet feed which Mr. Lyon's has arranged."

He gave us all a nod as she went on to say, "We will meet tomorrow precisely at noon to go over the scenario and then do a walk thru so that everyone in attendance will know their proper position and their roles. Please be here on time and ready to work."

With that one of the new curtains rose and there stood Felicity, a smile on her face like none I had ever seen before. Those in attendance were more than happy to dig into the wonderful food she had been kind enough to prepare for us. I smiled as I saw Andrea give her a kiss, the young woman's eyes shining up at hers. It was obvious their relationship had gone far beyond the normal dominant/submissive phase. They were in love.

As the night wore on, quite a few of us found our way up to the tenth floor, the wine flowing freely. We all tried to get Andrea to tell us something, give us a clue as to what would happen tomorrow night, but she remained tight lipped about it. I didn't notice how my wineglass was constantly being refilled but by the time the evening drew to a close, I had to fight to keep my eyes open. Abby and her mother helped me downstairs into our now beautifully furnished home and I was out before the light was turned off.

When I woke up the next morning, my head was pounding, as I was paying for my overindulgence. I saw the mattress beside me was empty but what was even worse was that the clock showed it was 11:55. I jumped out of king sized bed, looking around frantically as I tried to find my discarded clothing. I literally ran bare foot to the elevator only to realize I had left my new keycard for it on the dresser table. Security had been ramped up since Jade's firing and now we needed the card in order to access the lift.

I swiped the card only to see the light not turn to its normal color of green but instead flashed red. I tried it again, same result. One more time as I cried out in frustration before jabbing the button on the console.


"Hi, it's Holly on the ninth floor. My keycards not working."

There was a brief pause before I heard, "That's funny, we haven't had any complaints concerning the elevator this morning. Are you sure it's not operator error?"

I stood there trying to control my frustration while saying, "I tried it three times. Do you want me to try it three more times?"

"Yes, please."

I wanted to reach through the speaker and grab whoever it was by the throat but instead I swiped the card three more times, each time with the same result.

"Okay, I've tried it three more times but it still won't work. What are you going to do about it?"

"We should probably call Mr. Lyon's. He told us to contact him first if anything went wrong with the equipment. Let me see if I can find him."

I felt my temper rising as I replied, "Why, I think that would be a splendid idea. Why don't you call Mr. Lyons's so you can tell him one of his prize show ponies IS STUCK IN THE STABLE!"

I laid my head up against the coolness of the doors which were obviously not opening. It was almost fifteen minutes later that I heard a familiar voice say, "Hello there Holly. Is there a problem?"

"Why yes Mr. Lyon's, there is. Your new security system will not allow me to access the elevator so even as we speak I'm missing a very important meeting. Would you care to tell me why my keycard is not functioning properly?"

I waited not so patiently, counting down from ten, trying to control my anger only to hear, "That's funny, we haven't had any complaints concerning the elevator this morning. Perhaps it's operator error?"

I didn't even make it to five. What followed was a minute of an expletive filled tirade into the speaker, my voice growing more hysterical by the moment. I first told him what I thought about his operator error, then I told him where he could put and then stick his operator error, follow by how he could twist and turn his operator error in a way that was probably anatomically impossible but I think you get my drift.

By the time I had run out of words and breath, there was about ten seconds of silence until I heard. "I'm not aware if anyone might have said this to you in the past Holly. I firmly believe you have some rather serious anger issues."

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