tagTransgender & CrossdressersThe Role Players Pt. 03

The Role Players Pt. 03

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


*****

When I finally slipped behind the curtain, a sense of weariness took over, like I had just finished a marathon race. I would have fallen except for the lovely woman who pulled me into an embrace, my eyes opening wide as Mistress Jade's voice cheerfully said, "There you are Holly." My face must have shown my confusion as she laughed, "My dear, when I am character I can't show the world this side of me. I hope I didn't hurt you love4?"

"I...I'm well thank you Mistress Jade."

She shook her head, giving me a look of disapproval. "If we're not on stage Holly, I'm just Jade, okay?"

She gave me another hug, her hand in mine as she walked me over to a table resplendent with food and drink. Handing me one glass, picking up another as we sat down, her smile a warm one as I heard, "So, tell me all about Holly."

It was like talking to an old friend, the woman sensing I needed to step away from the character I had been portraying and as I told her about what had happened over the past two weeks, her smile grew even wider. "Andrea told me she had found a budding star and based on what I saw this evening dear, she is underestimating you."

This time the blush was real, not practiced as she laughed with me, not at me, her hand giving mine a quick squeeze.

"Alright everyone, let's see what we have here. I've tallied up the results."

It was Andrea who walked in, two gentleman carrying our books behind her as she took a flute of champagne. Taking a sip she nodded in the direction of the lady who was sitting beside me before saying, "As always Mistress Jade, you rule the day my dear with the most requests."

Like a child might, the dominant applauded herself and I saw Abby roll her eyes as her mother continued. "Second place goes to Abby and I'm happy to say our newest member finished in third. Congratulations Holly."

Another squeeze of my hand as I favored her with a weary smile. "Everyone has a rather impressive count of requests and based on my first look, I believe this grand opening will surpass even our Las Vegas gala. You should all be very proud of yourselves."

Hugs followed all around, the members promising they would return the next Thursday to go over our assignments which would begin the following weekend and by the time everyone had gone their separate ways it was far beyond the witching hour.

I felt Andrea step up behind me, a key being put in the lock on my uniform as she said, "Girls, if you will go upstairs and change. I would like a word with both of you before you turn in for the evening. I will meet you shortly in the living room."

I gave Abby an inquisitive look but she just shrugged, picking up her baseball bat and we both headed to the elevator. I hated getting out of my dress, the feeling of leaving the submissive maid behind making me feel empty. Finally, I donned a robe, going into the living room to find Abby already there. I was just about to ask her a question when her mother walked in the room, sitting down, a weary sigh escaping her lips.

Both of us watched her as she seemingly struggled for a moment before speaking. "I have never lied to our troupe but I did so tonight I'm afraid."

Abby moved over to where her parent sat, hugging her while saying softly, "I'm sure if you did it was for a good reason mom. What's wrong?"

She gave her daughter a bit of a smile before turning to me. "Abby will attest to this Holly. Mistress Jade has a rather nasty side to her if she doesn't get her way. She has always been the queen if you will and she has spoken to me in the past about leaving if someone ever were to come along who might surpass her. Two of our players did so tonight but when I walked in and saw Jade with you Holly, I fear she would have scratched your eyes out if I told her the truth."

I was trying to justify the way the brown eyed woman had treated me to the picture Andrea was painting but one quick look at Abby convinced me her mother was telling the truth. "Like I said mom, you had a good reason. So, who beat her?"

Shaking her head at her daughter I heard, "Well Harley and Holly made quite a scene from what I was told and when the evening was over one had 51 numbers while the other had 50."

I thought Abby was going to explode, her face turning jubilant as she flew across the room and I couldn't help but laugh as she attacked me. "I TOLD YOU SO! I WAS SO RIGHT AND YOU WERE SO WRONG!" The look on the elder woman's face was one of delight, taking in the sight as finally I squirmed free.

"Miss Andrea, is 51 and 50 good?"

Both of them started laughing, the look on my face now almost petulant as I was outside the loop if you will only to hear, "When we opened the Las Vegas club Holly, the highest number of requests were for Jade and the number was 24, less than half of the requests we had for both you girls tonight. Yes, those numbers are incredible, just as the two of you are."

I blushed, Abby beamed as Andrea went on. "My daughter knows how this works so I think she will be as surprised as I was. Normally the requests we have are for singular performers but at this opening more than half of the scenarios include two or more of the players in the same scene. Both you and my daughter were requested by 25 of the same individuals and that is unprecedented. It seems the two of you are a team."

It wasn't a tackle, this time it was a hug and a big kiss as her eyes shone and I heard, "You hear that sweet cheeks? We're a team!"

Her mom could only smile as she witnessed her daughter's enthusiasm. "What also seems to be the case is how many of our members want to see our sweet, shy, innocent maid either corrupted or led into a life of debauchery. You seem to have brought out either the best or depending upon your point of view, the worst in our members Holly. This opens up an entirely different avenue of scenarios for many of the other role players as well."

That night as I lay in my bed I couldn't sleep. I couldn't help but feel like when I awoke I would find myself homeless, out on the streets after all of this had been only a dream. Looking up at the ceiling, I pondered what my first part would entail. Thursday could not come fast enough.

When it finally arrived, all of the players congregated in the living room and after smiles and hugs had been exchanged we were given our assignments. Both Abby and I patiently waited as it seemed we would be last, not wanting it to seem like Andrea was playing favorites.

"Holly since this is your first time I wanted to pair you up with one of our more seasoned actors. It worked out perfectly when we had a couple, Renee and Thomas, request you and Abby for a scenario. They wish to cheat on each other in the same house at the same time and they require two maids to do so. Renee requested Holly and Thomas desires you Abby."

"Mom, is this the couple who said they would double the quote if they could be Holly's first?"

The look her mother gave her daughter was as cold as a winter's night but Abby looked the picture of innocence, knowing full well it was a jab at Jade. I looked over and saw a look on the dominant's face that was in stark contrast to the last time we had been in the same room.

"That's correct Abby but money isn't important at the moment. What really matters is the client's needs and how you and Holly would not only meet their expectations but will exceed them. Here are your copies of the scenario. Go over them and if you have any questions, see me immediately.

By the time we had left the room Abby was grinning from ear to ear as I shook my head at her saying, "You're going to get us in trouble with Jade. Please stop Abby."

She only shrugged saying, "Joke 'em if they can't take a fuck honey. Jade's been acting like we're all beneath her for quite some time, serves her right."

Rolling my eyes we went to her room and sat down to read the scene, eager to see where this Saturday night might lead.

ROLE PLAYERS

SCENARIO

Renee and Thomas are married but their love life has grown stale, boring. One night one of them cheats on the other with one of the maids and when the other finds out, they in turn return the favor at the same time.

It wasn't a lot to go on but Abby seemed to take it in stride. She pulled out her tablet and began taking notes, suggesting ideas to me and so I tried to do the same. By the time the evening had come to a close, we had a plan in place.

Friday night we did a walk thru, seeing how our movements might lead to chance encounters with the other participants and I couldn't help but laugh. It almost seemed like an old Marx Brothers film with people passing in the night. Sex though, not laughter, the soundtrack to what would transpire.

The next evening both Abby and I shared a dressing room, her former makeup artist assisting us both as we prepared. There was a knock on the door and to my surprise two people walked in. It didn't seem odd one of them being Abby's mother but the second was Antoine who favored me with a smile that once again left my heart beating a bit faster.

Andrea spoke saying, "I just wanted to say good luck to both of you. I know you'll make this a special evening for both of them." I could tell there was something else on her mind, the way she was looking at me. "The gentleman who you will call Mr. Thomas did have a special request though. He wanted to steal, his words not mine, a kiss from you Holly and I told him I'm not sure if you would agree or not."

I didn't really have time to speak as I felt a hand take mine, turning to see Antoine smiling, his eyes quickly capturing my attention. His voice was like silk saying, "I would think for any man the chance to kiss such a vision would be a rare pleasure indeed. Would you not agree my beautiful maid?"

I guess he really wasn't looking for an answer as his hand moved behind my neck and he pulled me in for a kiss. As his tongue played over my lips, I was happy to give him entrance and he became even a bit more demanding. I greedily let my hands roam over his chest, my mind with thoughts running wild with the most decadent of thoughts, completely lost in the moment.

It was Abby's voice that broke the spell, "Oh for the love of god, get a room you two!"

I stepped back only to see Antoine's eyes dancing in delight as he turned to Andrea. "I think our Holly is more than capable of granting the gentleman a kiss, aren't you my dear." This time it was a full body blush as Abby's mom looked at me and I nodded my head in agreement.

When it was time for the proverbial curtain to rise Abby gave me a quick hug and we were off. The blonde maid making her way through the door, leading to where the others awaited. It was to be a first for me in many ways and it took all I had not to grin at just how happy I felt precisely at that moment.

The first maid walked into a setting, a den like atmosphere, with the same two people that had approached me exactly a week ago sitting on the same couch. The problem was one of them was at one end, while the other was as far apart as he could get. Both of them looked almost miserable, playing their own roles as the dissatisfied married couple as I heard Abby say, "Mr. Thomas, would you care for a drink Sir?"

The gentleman gave her a smile, something that did not go unnoticed by his wife as he said, "I'd love a scotch on the rocks Abby. Let me give you a hand young lady." She gave him almost a wicked smile, turning as her hips swayed provocatively, giving him quite a view. I was positioned just around the corner out of sight and by the time the two of them disappeared it was time for me to make my own appearance.

"Good evening Miss Renee, would you require a white wine M'lady?"

I got a smile as beautiful as the woman was, her voice warmly saying, "You're such a dear Holly. Yes, please."

I turned, making my way back toward the kitchen only to stop at the sounds I heard. Quietly I opened the door just a fraction, my eyes growing wide to see the gentleman kissing my counterpart, his hand under her short skirt, taking liberties. Turning quickly I made my way back to where the woman sat, my face filled with concern as I bit down gently at my bottom lip.

"Holly, is something wrong?"

I started to speak but the words simply would not come out. Finally I let forth a sigh, holding my hand out as I helped her gently to her feet. She had a look of confusion on her face as I held a single finger up, signaling to be silent, as we walked over and once again I opened the door just a bit.

Things had taken a turn for the worse, or perhaps the better deciding upon who was who. This time the picture my eyes took in was that of Abby on her knees with Thomas's manhood filling her mouth. His eyes were closed, his smile wide as he took advantage of the poor girl. I turned, seeing a look of rage on the face of the woman witnessing her husband's infidelity. Seconds later I was almost pulled off my feet as she led me back into the den.

Her voice was livid, her eyes sending off sparks. "That bastard, doing this while I'm just a few feet away. Well two can play at this game Mister."

My eyes grew wide as she unzipped her pencil skirt, the garment sliding gently to the ground. Stepping out of it, I saw only a garter belt with stockings attached as she took me by the hand, pulling me down on top of her as she lay back on the couch. Her hand finally releasing me but only long enough to pull my head down so I was positioned between her legs, one of which was now splayed out over the back of the sofa.

I needed no more encouragement. Her eyes showed her need and utilizing the knowledge that Abby and her mother had taught me I eagerly began. A flick of the tongue here, a long slide up her slit following as her eyes closed, the smile beginning to return to her face. A quick thought as to how each individual woman had their own unique scent and taste. It was quickly becoming my favorite delicacy. I began giving the older green eyed beauty precisely what she desired. Revenge on her cheating spouse.

It didn't take long, her hips beginning to buck, threatening to throw me from my perch. During our research Abby had told me of some women who literally would have their orgasm spray forth from their body, squirting is what she called it and I had no idea I was about to get my initiation to such. When her back arched and she screamed her pleasure, my face took the brunt of it, soaking me as I blinked to clear the moisture from my eyelashes.

Looking down at her, watching her caught in the throes of her own release I marveled at just how lovely she truly was and I knew I had to have more. I once again captured her with my mouth, another cry escaping her lips as the wave of her first orgasm was still hitting her and a second was demanding to follow, not far behind. I was rewarded only a minute or two later and this time it felt like a deluge, the dam opening as we both spilled to the floor, her body writhing in ecstasy.

When she finally opened her eyes, blinking at me I saw how they had clouded over, heavy with lust. I felt proud to have given her such as she almost stumbled to her feet, finally standing up staggering as I picked up her skirt and she put her hands on my shoulders as I helped her replace the garment. It was only then we heard a sound that echoed throughout the dwelling, the sound of another's orgasm as I could only picture the maid on her knees mouth being rapidly filled with the gentleman's seed.

That seemed to bring the woman Renee back to her senses as she said shakily, "Perhaps I might have that glass of wine now my dear?"

"Of course Miss Renee, I'll be right back."

Walking back into the kitchen I opened the door all the way only to stop at the decadent sight before me. Abby was still on the ground, licking her lips like a cat might in trying to capture the last few drops of delicious cream it had just enjoyed. Meanwhile the adulterer was zipping up his pants as he saw me, his smile becoming wider.

"I, I'm sorry...I didn't mean to, that is I...," as my words trailed off and he walked over, almost pinning me against the counter, his body close to mine.

I had to fight to remember how I was supposed to be the shy, quiet innocent character as I let my eyes lower only to feel my chin being lifted. His eyes were still as heavy with desire as the woman who I had just left behind and he almost growled as his lips found mine in a crushing kiss. A part of me wanted him to take me right there on the kitchen floor but I had to settle for his hand under my skirt, playing with my bum. Finally he stepped back and as I gasped I heard him say huskily, "Soon my dear. Very soon."

Seconds later he was gone and I stumbled over to where Abby was standing, the smile on her face one of complete satisfaction. She giggled, taking a towel and wetting the end as she cleaned my face. I wondered if Thomas had tasted Renee on my lips, the thought sending shivers down my spine. When she had finally finished I gave Abby a smile of my own before letting my tongue flick out and capture an errant drop of the gentleman's cum she had missed. Opening my mouth to show her, she kissed me and we shared our common bond.

About a minute later I returned to the den to find the couple happily chatting as I gave her the glass of wine before saying, "Dinner is ready Mr. Thomas and Miss Renee. If you will please follow me to the dining room."

We had cooks on staff for our events so it was easy for Abby and me to serve them a gourmet meal. It was fun seeing the wicked glances that the two sent our ways. The woman Renee licking her lips as I would look to refill her glass while her husband took an opportunity when Abby bent over to remove his plate, his hand reaching underneath her extremely short skirt.

When the two of them had adjourned back to the den, Abby and I watched from around the corner, listening intently. The woman stifled a yawn before saying, "It's been a very long day Thomas. I'm going to retire early. Would you care to join me dear?"

"No, I think I'll have a nightcap, perhaps watch television for a bit. I should be up in a couple of hours. Sweet dreams my love."

It took all we had not to laugh as we returned to the kitchen. Both of us knowing the two were lying to one another and sure enough a minute later Renee walked up to me and in a conspiratorial tone whispered, "Give me five minutes and then come to my bedroom Holly."

I counted off the minutes, giving Abby a wink as I made my way down the hallway. The door was open and as I walked inside she had discarded her blouse and skirt, standing there in only her garter belt, stockings and heels. Her mouth captured mine, the kiss as demanding as her husband's had been and I happily gave her what she wanted. Finally she stopped, walking around to stand behind me, the zipper being pulled down as my uniform fell gracefully to the ground.

Everything I wore was precisely the same as I had the night the two of us first met, but she had not gotten a glimpse at the corset and certainly not of the boy shorts and the secret it held within. Her eyes grew wide, her grin a lascivious one as she stopped in front of me, dropping to her knees as she reached inside the lacy garment and freed me.

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byhollygurl29© 6 comments/ 5882 views/ 8 favorites

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