tagTransgender & CrossdressersThe Role Players Pt. 02

The Role Players Pt. 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.

Abigail/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 awoke the next day it was to a beautiful sight. Abby sat perched on the side of my bed, her eyes sparkling as I heard, "Are you going to sleep the day away girlfriend?" I managed a bit of a smile as she stood, holding out a matching black lace cover up for me to don as she took my hand and pulled me down the hallway to where her mother sat on the couch, coffee cup in hand.

"Ah there you are young lady, did you sleep well Holly?"

My voice was soft, "Yes Miss Andrea, thank you for asking."

I got the full smile for that one. "That's good to hear. Would you like some coffee perhaps?"

I shook my head as Abby took my hand and we sat down together across from her mother. "Holly, my mom and I were wondering if you enjoyed last night?"

This time my smile was genuine, my voice the same. "It was one of the best nights of my life and I can't thank both of you enough for what you did for me. I will always be grateful for your kindness."

Abby grinned saying, "Well I wasn't very kind to you last night sweetie. Did you have a favorite part by chance?"

I didn't really have to give it any thought. "Every second of it. From the first moment on, you made it seem so real and it let me live out what I've only ever fantasized about it. I wouldn't change a thing, honest."

Sitting across from us I heard, "Well then, was there any part of it you didn't enjoy Holly?"

Once again, it hit me and I felt my emotions beginning to overwhelm me. I forced myself to keep a brave face as I replied, "When it was over, I didn't...I mean, that wasn't...enjoyable." Standing up from the couch I looked at the beautiful woman sitting there as I gave her my best smile, forcing my voice to remain even. "But all good things come to an end, at least that's what I've heard. Thank you so much for all of this. I can never repay you. I'll go get changed and find my way out."

I wanted to run before I started crying but instead I heard a voice say, "Holly, may I ask you a question?"

I turned only to see Andrea holding her coffee cup out to me. "Will you refill this for me please? Add just a dollop of cream, the pitcher is next to the coffeemaker dear."

Walking over, taking the offered mug from her I went into the kitchen, fixed a refill and brought it back out to where the older woman sat. I offered it to her only to hear, "I'm not sure about you but I've always been under the impression that a submissive did not leave a room until they were dismissed. Were you dismissed...Holly?"

I felt my face turn red. "No Miss Andrea, I'm sorry."

She finally took the mug from my hand as I stood there waiting. "Well then since you have not been dismissed I suggest you put that lovely little butt of yours back on the couch, is that clear young lady?"

I bit down gently on my bottom lip before replying, "Yes Miss Andrea."

Turning I walked over to see Abby grinning, her voice not loud but easily heard in saying, "She's so bossy sometimes, isn't she?" With that she began giggling and I couldn't help but smile.

Her mother rolled her eyes at us. "Why do I think the two of you are going to be a problem for me?"

Abby tried an innocent look but somehow I don't think Andrea bought it. "Alright, this is how we are going to proceed. It's just three ladies talking with one another, one saying a bit more than the other two," as she gave us a bit of a glare. "I know you'll have questions Holly but please hold them until I tell you, okay?"

I nodded, a bit of a puzzled look on my face. Little did I know just how confusing all this would prove to be moving forward.

"When we played last night Holly, both Abby and I agreed that you were absolutely wonderful. My daughter tried every trick in the book to trip you up and you responded to every single cue with the proper response. Your comment to her about losing a few pounds was an added bonus and it showed how quickly you think on your feet. It was most impressive and quite frankly, I rarely see my daughter speechless. That was quite remarkable."

I couldn't help it, I did what I always did when I received a compliment, and I blushed. Meanwhile I saw Abby out of the corner of my eye say, "Lose a couple of pounds my ass." She stuck her tongue out at me and we both laughed.

"Getting back to the subject at hand ladies." We turned our attention back to the woman sitting across from us to hear, "I think we have a solution for your problem as far as your unemployment and housing are concerned Holly. We would like you to join us doing exactly what you did last night."

I felt my heart begin to pound, my mouth opening to say something only to remember what she said and I quickly closed it. "A quick learner my dear, that will serve you well. Now, I am not suggesting we are hiring you to be our maid. No, we are hiring you to be a submissive maid, to join us as one of the players in our troupe."

Visions began dancing in my head, as I felt Abby's hand take mine, giving me a reassuring smile as her mother continued. "What we are offering you Holly is a chance to live out your fantasy while helping others enjoy theirs. You will receive a base salary and when you actually play your role, you will get a percentage of whatever the quote is for that particular scenario. I know you said you were barely getting by at the book store but I promise you if you join us, you will do far more than that."

I took all this in, feeling like the world was tipping on its axis and I was spinning out of control. Now it was Abby's turn to speak, drawing my attention and saying, "Sweetheart, I've never seen anyone react in quite the manner you did last night. I told Mom you're a natural and I can think of so many different scenes that our members would enjoy playing with you. I had a ball last night being the mean girl and I promise you given the chance, you'll have people lining up to fill your dance card."

Sitting there, I was at a complete loss, the look on my face making that obvious as I heard, "Alright Holly, I know you have one question that has come to mind, the most important one of them all. If you want I can already tell you what it is. Come over here young lady."

I got up, walking slowly over as Andrea opened her arms and to my surprise pulled me into them. My head fell on her shoulder, the move both gentle and supportive. Her voice was soft, the words again drawing me in. "You're going to say, why me? I'm no one special. Why on earth would anyone want to pay me, want to play with me? That's the question, isn't it dear?"

My head simply fell of its own accord but she was having none of it. Her hand lifted my chin, her eyes warm and inviting while speaking. "Just as you were falling asleep last night you thanked me for making you feel special, do you remember that?"

I nodded, not trusting my voice as she went on. "You showed many talents last night young lady. You acted and reacted better than anyone I've ever met for a first timer. There is one thing though that you are truly horrible at and that is you have absolutely no confidence...in yourself."

There would be no respite, she wouldn't allow me to lower my eyes. "I believe Abby and I could compliment you time and time again and it simply would wash over you like the waves do the shore. You are already special Holly, you just need to see that for yourself and I'd like to prove it to you tonight, if you will allow it."

Once again, my face must have shown my puzzlement as she laughed saying, "Do you also remember you telling us earlier this morning that you could never repay us for our kindness?" I nodded as she called me on it. "Well, as a matter of fact, you can repay us. We did you a good deed and you're going to return the favor this evening, aren't you?"

I still had absolutely no idea what was going on but I nodded yes as she gave me a quick kiss on the forehead. "Very well Holly, you're dismissed now. Go change and I will expect you back here tonight promptly at seven o'clock. Leave all your items on the bed and I will take care of them for you. Here is the key for your chastity device, remove it as well. Abby will see Eric out when he's ready to leave. "

When I returned to my room, undressing, I looked down almost wishfully at the cage I was still wearing. In the past I would have thought that after a night like the evening before that it would frustrate me beyond belief at the fact I couldn't find my own pleasure. Instead as I removed it, I felt a loss, the control at the hands of another outweighing my own desires.

It was about fifteen minutes later that I returned to find Abby alone, her hand taking mine as we went to the elevator and finally exited out onto the first floor. I had a million questions to ask but the young lady beside me wasn't in the mood for them. "I'm telling you right now Eric, don't ask because in reality, I don't know. This is all my Mother's doing."

Sighing, we went out into the heat to next door where I used my key only to turn and see the young lady already making her way back home. As her door shut, mine did the same and for the rest of the day I simply sat and tried to come to grips with what I had been offered and why I should or shouldn't accept. Finally, I fell asleep in the chair and when I opened my eyes it was already past six and I hurried to take a shower and get dressed making it back to Role Players five before the hour.

I knocked, the door opening and as I went inside Abby said simply, "Tenth floor, third bedroom on the right." Then she turned, making her way back into the darkness and when I called out to her, she ignored me and seconds later was gone.

Taking the elevator to the top floor I exited to silence, not a soul in sight. Moving down the hallway, I passed the bedroom I had been in the previous evening, the bed now made up and awaiting its next occupant. The third door was open, the room masculine in tone versus the pink of last night and as I peered in I saw a laptop on the desk, already open. There was a picture in a frame of a stunning woman who looked to be approximately Andrea's age but with short black hair and green eyes. On the picture, a post it note in a feminine script with the words written PRESS ENTER ON THE COMPUTER.

I sat down at the desk, did as the note had instructed and a white screen came up with the words ROLE PLAYERS and below that SCENARIO as I began to read.

A cougar is a sexual predator, a woman in her thirties or forties who seeks sexual intimacy with a younger man. Your name is Chris and recently a wealthy widow named Samantha Collins has seduced you and has made you her consort. She has lavished you with gifts, taken you to many of the finer restaurants and various philanthropic functions she funds. Your picture alongside her has been featured in many magazines. The problem arises in the fact that you have been steadfast in continuing to work at the office job that supported you prior to meeting her. She fears one day you will simply leave her for another, someone more attractive and certainly younger.

What your lover doesn't know is that you have a secret. You have kept the small studio apartment that you lived in prior to this and in that dwelling is meager furniture which holds a myriad of items. The drawers full of various lingerie. In the closet, hidden behind all of your old clothing, a garment bag holding the one thing that has brought you the greatest happiness in all your years, more valuable than anything the older woman has ever bought you.

It's Friday night and Miss Collins has told you that she will be gone the entire weekend on business and this has given you a chance to return to your former home, to enjoy that which you have gone without for so very long. The very room you are seated in right now is your apartment, your secret place.

WHEN YOU HAVE FINISHED READING THIS, PRESS CONTROL M.

I had already started trembling, my fingers fumbling on the keyboard and it took me three tries until the screen went dark only to be replaced by an instant messenger popup and my eyes opened wide as I read what was typed there.

I KNOW YOUR DIRTY LITTLE SECRET.

There was no name, nothing to indicate who it was. Only the icon awaiting my response as I typed in tentatively...WHO IS THIS?

THAT'S NOT IMPORTANT FOR NOW. WHAT IS IMPORTANT IS THAT YOU LISTEN VERY CLOSELY TO ME OR I WILL DESTROY YOU AND SAMANTHA COLLINS. NOW, ARE YOU LISTENING?

I didn't even realize I whimpered, the words so commanding as I typed in YES.

GOOD, NOW I KNOW WHY YOU ARE THERE. I'VE ACCESSED YOUR COMPUTER AND I FOUND ALL THE IP ADRESSES, ALL THE WEBPAGES AND EVEN BETTER THE STORIES YOU'VE WRITTEN CHRIS. OR SHOULD I SAY...HOLLY?

It was like someone had reached through the screen and slapped me, the blow more mental than physical but as I was reeling more words appeared.

YOU HAVE QUITE AN ARRAY OF CLOTHING THERE HOLLY, WHY DON'T YOU PICK OUT SOMETHING PRETTY TO WEAR FOR ME.

I stood up as if in a daze, opening one of the drawers only to find it empty. I opened a second, only to find it the same and as I began to panic there was nothing to be found. Finally, I opened the closet door and it too provided me with the same look. Everything was gone.

Sitting back down, to my horror the camera came on, the picture of me in dismay as another message appeared.

YOU LOOK SO DISRAUGHT HOLLY, IS SOMETHING WRONG?

I tried to turn the camera off but to no avail, a bead of sweat appearing on my forehead.

I HAVE CONTROL OF THE COMPUTER. I SUGGEST ALL YOU DO NOW IS READ AND OBEY.

I felt so helpless, trying to come to grips with what was occurring but the onslaught continued. Pictures of men dressed as maids, others of Miss Collins, the woman in the frame interspersed through them.

JUST THINK HOLLY, SAMANTHA COLLINS WILL BE THE LAUGHING STOCK OF THE TOWN WHEN IT TURNS OUT HER HANDSOME YOUNG MAN SHE IS KEEPING IN REALITY IS A SISSY FRENCH MAID. SHE WILL BE CRUSHED AND IN THE PROCESS YOU WILL FIND YOURSELF THROWN OUT INTO THE STREET AND JOBLESS. ESPECIALLY AFTER I POST ALL OF THIS, EVERY WORD, EVERY SINGLE KEYSTROKE TO THE WORLD ON THE INTERNET. YOUR LIFE WILL BE OVER.

I couldn't stop them, the tears now beginning to trail down my cheeks.

I WILL GIVE YOU ONE CHANCE AND ONE ONLY TO SAVE YOURSELF AND YOUR PRECIOUS OWNER. YOU WILL GO DOWN TO THE NINTH FLOOR, YOU WILL FIND EVERYTHING AWAITING YOU THERE. YOU WILL DON EACH ITEM AND THEN YOU WILL PUT THE BALL GAG IN PLACE. THEN YOU WILL SIT DOWN IN THE CHAIR WHICH HAS FOUR RESTRAINTS, ONE FOR EACH ANKLE AND WRIST. YOU WILL ATTACH THREE OF THEM TIGHTLY, LEAVING ONE ARM FREE WHICH YOU WILL USE TO PUT THE BLACK HOOD OVER YOUR HEAD. IF YOU MOVE FROM THAT SPOT, IF YOU DEVIATE FROM THIS PLAN EVEN A SINGLE INCH, THERE WILL BE NOTHING TO STOP ME FROM ACTING. YOU HAVE UNTIL 7:30 PM SO I SUGGEST YOU HURRY.

I looked at the icon on the computer seeing it flash 7:19 and with a cry I launched myself off the chair. Sprinting to the elevator, I frantically pushed the button. By the time it arrived on the designated floor, I saw the chair, along with all the clothing I had worn just the previous evening. By the time I was seated in the chair precisely as I had been commanded, my body was shivering all over, my mind in full blown panic mood. The hood leaving me with only one sense remaining, that of hearing.

To be frank, I'm not sure how much time passed from that moment until I heard a set of heels clicking across the concrete floor. I sat as motionless as I could, only to feel the final restraint pulled tightly and then cinched in place. Only then did someone pull the hood from my face and I looked up to see the woman whose picture I had seen on the desktop.

My eyes must have shown my absolute confusion as she gave me what could only be described as an extremely wicked smile. The picture had not done her justice, her beauty classic and her bearing was almost regal. She exuded confidence in herself and in the situation as it radiated from her. I could only sit there and listen as I heard, "Well, well...what have we here?"

In my current state, a reply wasn't possible and she didn't look to be expecting one either. "I always was afraid I would lose you to another woman Chris, I just didn't think it was the woman who was inside of you all along."

My head hung down at those words but not for long. "Look at me boy, I want to see your eyes and how you react when you finally come to grips with what is happening here."

Slowly I obeyed, her smile as cold as the room suddenly felt. "I am very meticulous dear with my wardrobe as you know and one day recently something seemed out of place when I went to my lingerie drawer. Things had been moved and in one case, an item was missing. I'll give you one guess where I found that item."

My face turned crimson as she went on, "Your room proved to be most interesting dear boy. The computer I bought you was password protected but of course since I had purchased it I made sure my IT people left me a backdoor in which I could gain access at any time. Would you like to guess what I found?"

It was like a noose around my neck growing tighter and tighter. "I thought I might catch you in an affair, sexting some young whore only to my surprise to find the whore...is you. Those stories you wrote Chris, I'm sorry I mean Holly, all those depraved things you talked about others doing to you. You've been a very bad, bad girl."

I couldn't hold my head up now if I wanted to, I felt like I had been beaten without a single blow falling but she was nowhere near done. "You think I'm a foolish old woman who would not investigate your prior address. That I didn't know about that little hideaway you still owned? It was child's play to have one of my security people break in and bring me all those things you treasure even more than you did me."

She stepped closer, her voice now an inch away my ear as I heard, "So, in the end you didn't leave me for another woman boy. I left you for another woman, the one I'm going to make out of you. Miss Andrews, I need you."

Another set of heels walked across the floor, to my dismay the woman who I knew as Andrea stood there with an IPAD in her hand, the look she gave me one of disgust as she listened to the woman say, "This will not do at all. I want a complete change, from head to toe. Have her hair colored, cut and styled in what can't be mistaken for anything but a woman's coif."

"I want permanent makeup done. Eyebrows, eyeliner, eyelash extensions, lip liner and full lip color along with a beauty mark on her right cheek area. Multiple ear piercings and full body electrolysis, not a single hair remaining on her with the exception of her head. Botox, her lips need to be fuller and proper fingernails as well."

A soft whimper came forth, not lost on either of the women as the one called Samantha lifted my chin up, my body shaking violently as I heard, "Full breast augmentation, I think 38D should do this tramp nicely. I'm not sure though about one thing. I'm either going to have her chemically castrated or possibly sexual reassignment surgery done. Oh well, I'll make my mind up soon enough."

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