tagTransgender & CrossdressersThe Role Players Pt. 06

The Role Players Pt. 06


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.



The next morning both Abby and I were already in the office when her mother walked in. She looked absolutely radiant, the smile on her face quickly reminding me of the night before. "Mother, you look...refreshed."

Andrea's eyes sparkled as she gave her daughter a hug, her voice soft in the young woman's ear saying, "Thank you for the most amazing birthday I've ever had." Abby returned the hug as I tried to make a discrete exit only to hear, "Oh no you don't young lady. You sit right down, we have something to discuss."

I sat back down, wondering if this was about last night only to see the woman now sitting behind the desk to take out a folder. Her demeanor took on a serious look as she began to speak. "I'm glad you're both here. I've been struggling with this request and I'm hoping the two of you might help me to figure out just how me might proceed or if we should just tell the client no, I'm sorry we can't help you."

I looked at Abby but she seemed as unsure as I was about what this might all be about. Finally, Andrea handed it to me and as I opened it and began to read, I felt like I was looking at words that could have been written about me only a few short months ago. Yes, there were a few differences of course, but on the whole, my heart went out to someone I had yet to meet. I finally had to stop, worrying my emotions were about to overcome me. I motioned to Abby, her mother nodded and I handed the documents to her.

I took a deep breath before speaking. "To me this is not a scenario. This is a human being who is hurting and I will not profit over someone else's pain Andrea. If we do this then we need to do it in a far different way from the norm. If so, then count me in."

The smile I received told me I had made the right decision and by the time Abby finished, I see she too was moved by what she had read. "Holly's right Mom, but I think we have to be very, very careful here. She's already been hurt and we don't want to add to that. We need a plan."

Andrea nodded saying, "I agree completely with both of you. I've never done this before but I think it might be a good idea to meet with this young woman's mother, the woman who came to us with the request. Perhaps she can share her thoughts and together we can see about taking a bad situation and turning it into good."

It was later that afternoon that Abby and I returned to the office, Andrea was in conversation with a woman who looked to be somewhere in her forties. Though she still retained a bit of her beauty from her youth, the look on her face made her appear older than she was.

"Ladies, this is Margaret. Margaret, this is my daughter Abby and her friend, Holly."

It surprised me when the woman got up and gave me a hug, her voice showing her struggle while saying, "Renee said if anyone could help my daughter it would be you Holly. She spoke so highly of you that I just had to try."

I gave her my bravest smile as we sat down and she began to talk. "Felicity has been sheltered all her life because of her...being different. My husband and I had her tutored privately in our home but now that she has turned 21, she's been wanting to explore more of the world. We've tried to be supportive but when she came home about a month ago from an evening out, she was devastated, heartbroken if you will."

Reaching over, letting my hand take hers I gave her a smile and a nod as the words became more difficult. "It turned out she had gone to a club, met a young man and after one thing led to another they found themselves becoming a bit more intimate. That's when he found out that Felicity was born...", her voice breaking as she seemed to be unable to finish.

My voice was soft in saying, "Felicity has the breasts of a woman but the genitals of a male, correct?" She nodded, her head hanging down and for a moment I thought it might be because of shame but I think it was more because she believed she had failed her daughter in her upbringing.

"Felicity to us is a treasure, a special girl who brought us such joy and all we wanted was for her to be happy. The young man who she met did not cause her physical harm but the pain he unleashed on her with his words were cruelty of the worst kind. Since then she has become withdrawn, thinking the entire world will view her as some kind of..."

The tears now ran down, the woman sobbing as both Andrea and Abby stepped forth to console the woman, her heart breaking for her child. I gave them time, letting her get herself back under control as I looked at Andrea, a silent exchange between the two of us, as she gave me her approval. She knew in advance what I was about to propose.

"Margaret, what we normally do here I do not believe will help Felicity in anyway." I saw the look on her face, the hope she had beginning to harbor slowly fading. I wasn't done. "So, what I believe we need to do is to have Felicity join us here so that she can meet me, Abby, Andrea and perhaps one or two more of us. This way she can see that there are people in this world who will not judge her, but will embrace her for being the treasure you speak of."

The tears threatened to return but I moved forward. "I think what Felicity needs from us, is for the vast majority, the truth. Perhaps if she sees how I found my way here through the help of my friends, perhaps she will let us do the same for her. Now, a little fantasy tied in with the reality I think might be beneficial, but it will all depend upon her. We want her to be comfortable, to learn to embrace her differences and celebrate the special woman she is."

Once again I let my hand find hers, squeezing it tightly and she looked up as I said, "I promise you Margaret, all of us here will do everything in our power to replace Felicity's bad memory with a good one."

That Saturday evening wasn't like any of the one's I'd experienced at Role Players in the past. The five of us agreeing that the happiness of one individual was the sole reason we were all assembled together. We'd made arrangements in advance to have Antoine greet Felicity at the front door and he had escorted her over to a table in the club setting we had decided to utilize. I could tell he was trying to be his normally charming self but she wasn't make it easy on him. Finally, he gave her his best smile before walking away.

The club was normally a loud, vibrant scene but there were only two occupants here at this time. One of them now sitting rather nervously, directly in from of me, as I approached.


The young woman who looked up was wearing a flannel shirt, a pair of baggy pants and from what I could tell no makeup. Her black hair was limp, straight and her eyes which looked to be a light blue reflected the pain I know she was feeling inside. She looked as if she wanted to hide her appearance from the world and once again I felt my heart ache for her. I got a nod as I gave her my best smile, sitting down, and saying, "Hi, I'm Holly."

I saw the look of confusion on her face, knowing the way I was dressed at the moment was anything but that, belying my name. I'd never thought of Eric being useful in a scenario but tonight, I thought he was needed here. I wanted to prove a point and this was the best way to do that, or so I thought. "I know, I don't look very much like a Holly, do I?"

Her voice was beyond soft, almost a whisper saying, "No, you don't."

"Well, sometimes looks can be deceiving. It wasn't long ago I was lucky to meet the two women who own this building and they helped me find what I'd been looking for. All my life I felt like I was a puzzle but with pieces missing and they helped to me finally complete it. Tell me, do you know the difference between being a submissive and a dominant Felicity?"

She nodded her ascent as I continued, "Holly began as a submissive french maid, a fantasy which I'd kept hidden away inside of me for quite some time. When she finally came out, I learned that life can be an adventure to be lived. She showed me that and while I may not be a real woman in the words of many people, when I'm Holly, I'm the perfect one for me. No, I don't have breasts or a vagina, but what I do have is a heart which beats both stronger and happier in not only my service, but in my day to day life."

I could see the last line hit home, realizing we both shared at least one thing in common. I saw a figure approaching out of the corner of my eye, Abby walking toward us as she stopped in front of the table we were seated at. Her smile was beautiful, her words sweet, while saying, "Hi Holly, is this Felicity?"

It was almost for me like looking in a mirror. Felicity who had been making a bit of eye contact with me quickly lowered hers as Abby sat down across from her. She looked at me and I gave her a nod as she began to speak. "Felicity, I'm Abby. I helped Holly here when she was trying to find herself. I'd like to help you too, if you would like that."

I could tell how the young lady was struggling within, knowing how the heart can tell us one thing but the mind will always remind us of the past. I let my hand reach down and take hers and I felt her tremble. Leaning in I spoke softly while saying, "Felicity, I will make the same promise that Abby made to me when I first came here. This is your safe place. No one here will say or do anything that will make you feel that you don't belong. You've been hurt enough and now, you need to let that pain go. Someone told me it just takes a first step and though it's a hard one, I know now looking back, that it put me on the most amazing journey of my life. If you want to take that step, we'll take it with you, I promise."

I saw the single tear fall as Felicity's body began to shudder. Abby got up, moving around to where she stood behind her and leaned in to hug the young woman and with that she surrendered to her emotions. I continued to hold her hand as tears fell like raindrops. My friend offering soft words of encouragement to the young woman, holding on to her and not letting go.

Finally, when the tears had stopped and we had given her a few moments to calm Abby said softly, "Would you like to meet Holly, Felicity? It will take a bit of time but I promise it is well worth the wait, okay?"

This time when the dark haired young lady looked up at Abby her eyes showed a bit of gratitude as she nodded. Abby gave her one more hug as she extended her hand and I released my own. We walked backstage, the familiar door with my name on it a bit ajar. I saw Dawn, a beautiful smile on her face, already waiting.

"Felicity, this is Dawn. She is a dear friend and she helps Holly come to life."

The rather diminutive woman walked up, not asking, simply doing what she thought was best. She gave Felicity a soft kiss on the cheek before in a lilting voice saying, "It is a pleasure to meet you young lady. You have wonderful bone structure. Has anyone ever told you that?"

She seemed surprised and then to my delight, she giggled. The tension seemingly broken by such an innocuous comment as Dawn said, "There is the smile that should fill this face. It makes you even more lovely Miss Felicity."

A blush rose to her cheeks as I took off my shirt before sitting down in the chair. I missed the quick glance between Abby and her former makeup artist as Dawn began to gently touch my hair, her words as always soothing and within seconds I sat there, my eyes closed, my body limp.

Abby took Felicity's hand and pulled her close so that they could look down on what seemed to be my slumbering figure. "Felicity, when Holly came to us she was a lot like you. She was scared, so nervous about taking a chance on finding her happiness. Dawn is a practitioner of what I call self-help hypnosis. She plants a seed, as she did in Holly, which reminds her that it's okay to be whom you are. It doesn't change you or make you do things you normally wouldn't do. Instead, it simply helps you to embrace yourself, precisely as Holly has done. What Dawn just did was to remind Holly that it's okay to like who you are, to love yourself. Holly is unique, special...just like you."

For a second Felicity's head began to lower but Dawn's fingertips brought it back up. Her eyes were kind, her voice reassuring. "Holly felt the same way you do Miss Felicity. Now, she realizes she is an amazing woman and I hope soon you will as well. Just give us a chance and let us prove it to you. Just like she said, it's a big first step but it will begin a journey filled with joy, not sorrow."

Felicity nodded, though still a bit uncertain as Dawn returned to my side and began to work her magic. When I heard the familiar words I returned, my eyes opening as I saw the dark haired woman's orbs opening widely to see such a dramatic change. I gave her a smile before stepping forth and we continued the process. Finally, I stood before the young woman, my eyes shyly looking down while saying, "Hello Miss Felicity. I'm Holly, it's nice to meet you."

"You...you're beautiful."

I couldn't help it. I hugged her warmly, my body pressed up against her as I whispered softly in her ear, "As are you young lady. Please let my friends and I do for you as they have for me. Let them show you that Felicity will find there are people out there who will welcome her with open arms and minds that are the same. She doesn't need to hide in the shadows anymore, just as I once did. Let her find her own light."

She shivered in my arms but I wasn't sure if it was a good thing or possibly bad. Still, it warmed my heart to hear her say softly, "I would like to try, please?"

Giving her my brightest smile, I walked over and handed her off to my two friends. "I promise, you're in good hands with these two. I will see you in a bit beautiful." I gave her another hug and a quick kiss on the cheek before I made my way out through the door. My destination was Andrea's office and I had a feeling she would not be alone. I was right.

Margaret gave me a look when I walked in, her voice kind in saying, "You look even lovelier than I remember from opening night Holly." Walking up, I gave her a hug before sitting down next to her.

"Your daughter reminds me of myself not that long ago Margaret. My friends and I are trying to help her to embrace the same thing I fought against. In her mind, she's a square peg that doesn't fit into a round hole. Instead, we need to show her that she's a special piece, a unique individual who still can find her place in the world."

Margaret's eyes grew misty as I smiled. "Right now Dawn and Abby are with her, instilling a bit of self-confidence and working to draw out the beauty she hides behind those hideous clothes." Even her mother had to laugh a bit as I saw a bit of color return to her face. "I'm not sure that while she is here that seeing you will be to her advantage. We have her in what I feel will be a safe place and while I am more than sure she knows how much you love her, I want to make sure she finishes with us before returning to you. I do have a feeling though that when she does, you'll notice a change. Hopefully, a very good one. Is that okay?"

The young woman's mother nodded, her eyes turning to her hostess while saying, "Where did you find such a wonderful and wise young lady Andrea?"

The blonde beauty stepped out from behind her desk, reaching down to take my hand, as I gave her my own happily. "I'd like to think that Holly found us. She may not have known precisely what she was looking for, just like Felicity, but now she shines even brighter than I could ever imagine. She is one of the very few individuals I have ever met whose beauty arises not only from her appearance but also from within."

I blushed as Andrea reached up to brush black a lock of my hair that had fallen. A few minutes later Margaret took our leave and as she returned to behind her desk, I told the owner of the club what had happened up until now and the suggestion I had for moving forward. "Felicity shows all the signs of a classic submissive. What I'm not sure of is whether it's coming from her desires or from her own self-image. I don't want to make a mistake here. She's already fragile enough and I don't want to take a chance at upsetting the balance I hope Abby and Dawn are helping her find."

The look on the dominant's face was a pensive one as she said, "Abby has always been right about you Holly. She trusts her feelings. What are yours telling you about Felicity?"

That caught me a bit by surprise but it didn't take long for me to answer. "I believe she's truly a submissive. Perhaps if a dominant shows her a bit of attention, she can blossom like you helped me to."

There was that beautiful smile as she returned to her work and I went back up to my room, waiting to hear from Abby. Sitting there, I couldn't help but remember how I went through precisely what Felicity at that moment was experiencing. I hoped and prayed that the young woman whose heart closely resembled my own was finding her own place in the world, just as I had. Looking back now, I need not have worried.

To my surprise, it wasn't a phone call, but the real thing that walked in the door. Her blue eyes had a distinctive gleam in them as she announced, "You need to come downstairs with me, now." I guess I didn't move quickly enough for her as she grabbed my arm and literally pulled me off the couch. I tried asking a question or two but she just ignored me, moving quickly until we stood a few feet away from the dressing room.

When she turned around, I could see the excitement on her face. I could even hear it in her voice when she said, "Dawn worked her magic with Felicity and when she was more at ease she asked her what she envisioned when she looked in the mirror? When she answered I wanted to cry but I helped her become what she truly wanted and you're not going to believe what you see."

As she finally let me step through the door, I saw the young lady with the woman who had assisted Abby, smiling like a proud parent. My heart fell to the pit of my stomach as I saw Felicity looking in the mirror, her smile as Dawn had said, making her look not only beautiful but positively radiant. I walked slowly over to where she stood as she noticed my reflection in the mirror. I saw a more than familiar shy smile on not one but now two maids faces.

She was dressed as I was, from head to toe, but her beauty in my eyes far outweighed my own. I know we are our own worst critics but I wasn't saying it to be a bad thing. It simply looked to me as if she had stepped off the page of a magazine. One showing the perfect French maid with her dark hair now framing her face and in perfect contrast to the black and white uniform she wore. I let my hands go around her, giving her a hug, as my eyes sparkled. "Hello sister, you are an absolute vision Felicity. Just as I knew you would be."

She turned, her eyes misting a bit as she hugged me back and said, "I wanted to look like just like you. I couldn't have done this without you and you've made me so happy Holly. Thank you so much."

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byhollygurl29© 5 comments/ 3849 views/ 4 favorites

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