tagTransgender & CrossdressersThe Role Players Pt. 04

The Role Players Pt. 04


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 good part about the extra play was that the next day was Thursday and when I awoke I smiled knowing there would be yet another part to be played this week. By the time we were called into her mom's office both Abby and I were anxious to know if Andrea had taken my words from three days into consideration. Turns out, she had.

"Alright, this one is going to be a little complicated ladies. Why don't you read it and then I'll tell you my thoughts."



Mrs. Waters does not want her son marrying a woman named Taylor (Abby) who she sees as someone who is marrying him simply for his money. She concocts a plan in order to prevent the marriage. Taylor and her maid of honor Holly go out for one final night on the town prior to the ceremony. The two are picked up in a bar, drugged and then used by several men. She then blackmails Taylor into telling her suitor she has decided to call off the wedding or else the pictures of both her and her friend will be released to the public.

The grin on Abby's face was one of glee as she looked at her mother. "We've got to get the fraternity boys here for this one mom."

"It's alright being done dear, they will arrive on Saturday morning."

The young woman gave me a high five though I had no idea what she was talking about. "You're going to love them Holly. They're just like the beds in the three bear's story. Not too soft, not too hard but just right."

Andrea shook head at her daughter as she said, "Since this is going to be Holly's first time Abby, I'm going to need for you to work with her to make sure she knows what she is getting herself into. I'm sure you probably don't require any props but if you do, just let me know what it is that you need."

"Be aware dear this story is very personal for the client. This is what she wished she had done but instead her son did marry the woman and a year later she took him for every single cent he had. I have a feeling based on my discussions with her that she is going to be verbally abusive to you and Holly may catch a few of her barbs as well."

She turned her attention to me next. "Holly, the gentlemen that Abby are so excited about fulfilled a fantasy about a girl who was, shall we say, the center of attention at a College fraternity party." Abby tried to give me her most innocent look but it didn't take much for me to know who probably played that part. "They are all wonderful young men and I spoke to two of them personally and they would like to meet with you prior to the scene. I think that would be wise, okay?"

I nodded, already excited about the prospect and as Abby and I headed back to her room to share our thoughts. I came to an abrupt halt when she began taking items out of one of her dresser drawers. It was like one of those magicians who kept pulling scarves forth out of his hat but this time it was dildos. Big, small, thin, thick, studded, you name it, and she had them.

She picked up one, giving me her most wicked look as I said, "Abby, that thing is beyond huge!"

Laughing I heard, "This one is about average honey, trust me I know. Besides, it's about as big as you are if I remember correctly."

Damn her, as of course I blushed from head to toe but her only reply was to take the entire thing into her mouth, making it look as easy as it could be. Pulling it out she handed it to me saying, "Your turn."

Sighing, I picked up the monster but when it got only a couple of inches in I began to gag, coughing as I pulled it out only to hear, "Hey deep throat. We take baby steps first, okay?"

There were tears in my eyes as she nodded and she began to teach me how to do it right. Inch by inch we progressed as she also reminded me about not letting my teeth come into play and how it may say blow but in reality it means suck. A couple of hours later my jaw hurt but I had made quite a bit of progress. At least that what it showed by the marks Abby had drawn on the rubber cock as more and more had disappeared down my throat.

"Okay, I need to get in your pants now Holly." She laughed as I gave her a look before she walked over and once again opened her toy chest and pulled out what compared to the others seemed to be a rather small butt plug. "If you're going to lose your virginity Saturday night beautiful, we need to get you ready. I want this to be pleasurable for you and if you're not stretched out a bit it will be anything but. Get it, butt?"

I rolled my eyes as I removed the bottom portion of my clothes. Watching, she pulled out a container of lube and liberally covered the item before turning to me with that evil little smile of hers. I got up on the bed and seconds later I felt the cold gel and I shivered but without any issue at all it slid home and with the base pressed up against me it stayed in place.

"Well, it looks like you're a natural sister. We need to leave that there for a bit but before you go to bed tonight, we're going to go a little bigger. We'll take this step by step for the next two days and come Show Time you'll be ready for the real thing." I bit down gently on my bottom lip as I wondered if I had made the right decision. Either way, it was too late to back out now.

That night as she had promised we went a little larger, though it still didn't cause me any discomfort. The feeling of being full felt almost like I was enjoying a secret thrill. I must have smiled and Abby grinned as if she could read my mind.

The next morning, another change and as we did our walk through there were little sparks going off, the way my body was reacting to the strange invader a wicked secret shared by two. When Abby talked about what she saw happening tomorrow night I couldn't help but shiver though I'm not sure if it was from fear or excitement. Wardrobe was another matter. I wouldn't have the safety net of my maid's attire but something completely different and as I looked in the mirror I began to visualize what was going to actually happen.

I got ready a bit earlier than normal Saturday, knowing that we were going to meet our guests to go over things. I felt extra nervous, something Abby didn't miss as she took my hand, holding it only for her eyes to begin to sparkle as she literally ran over and hugged two gentlemen who had just walked in the door. I took a quick look, my eyes betraying me but it looked as if they were almost identical twins. I was right.

She pulled them over to where I nervously waiting. "Holly, this is Jason and his brother Jackson. Guys, this is our newest member Holly."

The smiles both gave me were nice and I wondered if I should shake hands but instead one of them pulled me into an embrace, his voice warm saying, "It's nice to meet you Holly. Abby has told us so much about you but she didn't say just how beautiful you are." I returned his smile, another hug from his brother and we all sat down.

Jason took the lead, taking my hand and holding it in his. "Holly, since this is your first time I wanted to make sure everyone knows their part so there are no unpleasant surprises, only good ones, okay?"

I happily nodded, feeling a bit more comfortable. "Alright, we're going to have some preset signs that tell us either to slow down or to speed up and it's going to be up to you Holly to tell us. I'm going to pair up with you at first when we pick you up at the bar. My brother will be with Abby and while you play your shy role, I'll be doing the same. My brother will be the more forward of the two of us."

His sibling gave me a smile as Abby grinned at him before his brother continued, "We'll buy you both drinks, I'll be going over to the bar where I'll slip something extra into them before bringing them to you. The effect will be a temporary loss of memory or inhibition, so you two will need to act the part. As I said Holly, all the cues will go through you so when we are returning from the dance floor you will stumble and that will be the sign that the drug is working."

Nodding again he went on. "When we take you outside for some fresh air, in reality we'll move to a different part of the sound stage where we will begin to play. My partner, my brother will be the first one to take you from behind and his line will be about how tight you are. That will give you a moment to allow your body to decide if it is ready for us to move forward. Your signal to me will be you mumbling, why you are doing this to me? If you don't say anything we will stop and when you are ready to proceed you will say your line."

He gave my hand a squeeze and I couldn't help but think how kind he was being. I wondered if perhaps he could pull this off, playing the role of a bad guy. I shouldn't have worried.

"Now, if you give us the go ahead I'll have Jackson grab you by the hair, pull your head back and I'll put my cock in your mouth. Remember, you've been drugged so let me do all the work and if I feel it's too much for you I will pull out and give you time to breath. I hear you're an expert at whimpering so when you're ready to go again just do that and we'll start over. I know what you've told Andrea and we'll be both verbally and physically rough with you but only after you've shown us you are ready for that."

After I got a soft kiss on the cheek, both of them left as Abby said, "You're in good hands Holly. Ready to have some fun?" Nodding a bit nervously, we went to the sixth floor and shortly afterwards the curtain went up.

Abby looked like she was almost dragging me into the club setting, my other free hand tugging at the extremely short black leather miniskirt I was wearing. "For god's sake Holly, lighten up. We're here to have a good time, alright?"

I shook my head as we sat down at a table, trying desperately to stop the skirt from riding up any higher, the flesh above my stockings coming into view. "I can't believe you made me dress like this in public. You owe me big time." The skirt was a match for the black leather bustier I wore with more than ample cleavage, a complete contrast to the shy, innocent individual I was portraying.

The blonde laughed, playing with her hair. She wore a red leather dress with strategic openings showing even more flesh than I was. The other part of her ensemble a pair of fuck me pumps with heels which had left her towering over me. I saw movement out of the corner of my eye as I heard the handsome young man say, "Hello there. May my brother and I buy you lovely ladies a drink?"

Before I could answer Abby turned on her charm saying, "Sure, double Captain Neat," as she rolled her eyes, "and a diet soda for my friend here. She's a party pooper."

I blushed, lowering my eyes as he laughed. "Jason, why don't you get those drinks and I'll introduce us to these two beautiful women." He moved off to the bar as Jackson pulled up a chair next to Abby. "My name is Jackson and as you heard that's my brother Jason. So what brings you two here?"

Abby frowned, showing off her rather large diamond ring on her left finger before saying, "I'm getting hitched in a week so this is the last time I'll ever have any fun. I'm hoping I'll get lucky tonight. Oh, and Holly here really needs to get laid or at least give some guy a blow job, she's in a kind of dry spell."


We were interrupted by Jason returning with our drinks as his brother laughed. "Well, I think we can arrange for that. You two are hot."

Abby grinned, then tossed back her drink in a single gulp as she grabbed Jackson's hand and pulled him out onto the dance floor. When I looked it wasn't so much dancing, it looked more like a lap dance the way the blue eyed girl was bumping and grinding against him, the smile never leaving his face.

I took a drink of my soda only to hear a soft voice say, "Hi, I'm Jason."

Giving him a shy smile I replied, "Hello, I'm Holly."

His eyes were kind but he didn't talk a lot as the music played and I continued to sip from my beverage. It dawned on me how he was portraying the same role I was. When a slow song came on I saw him trying to work up the courage to ask, "Holly, will you dance with me, please?"

I almost laughed as he gave me his puppy dog eyes and I nodded. Seconds later we were dancing slowly, that wonderful feeling of being in the arms of a man returning. His voice was barely a whisper in my ear. "You're doing great Holly. I just want to make sure you're ready for what's going to happen. Mrs. Waters is going to say some pretty mean things to you and Abby. My brother and I will be doing the same thing so I don't want you to be caught off guard."

I looked up at him, biting down on my bottom lip as I nodded before leaning my head against his chest. I felt the butterflies in the pit of my stomach as I knew the song was about to end and this was about to really happen. Taking my hand, leading me back toward the other couple I stumbled and almost fell except for his two strong arms not allowing that to happen. "Holly, are you alright?"

Blinking, I tried to focus on his face as I slurred, "I...I feel...funny."

We'd almost gotten back to the table when I saw Abby with her head on Jackson's shoulder, her eyes closed. "Hey bro, let's get these ladies some fresh air."

That was the sign and when the curtain came down we all moved quickly over to the next stage. Jason almost had to half carry me along as we entered through a doorway only to see six more men and one older woman, her face a mask of triumph on it. First Abby was handed off to two of the strangers and then Jackson joined his brother, taking my other arm leading me over to where a rather wicked looking bench waited.

"Look at them both, dressed like common whores. I knew it all along. I can't believe how foolish my son is if he thinks a woman like that could ever fit in with my family."

The words were spoken with pure venom in them as I heard Abby's moan, her clothing being removed as the two put her into place, a similar contraption as the one awaiting me. I felt Jackson's arms supporting me as Jason walked into view, a wicked grin on his face as he undid my skirt and it fell to the floor. I still had on my thigh highs and the lacy underwear but his eyes grew wide seeing what was inside them.

His voice sounded unsure as he called out, "Mrs. Waters, I think you need to see this."

The matriarch of the clan walked over, took a look at me and her smile became absolutely devilishly. "Well, well...it looks like little Holly here has a secret, don't you dear?" My head simply lolled, blinking, trying to focus only to hear, "Well, what are you two waiting for? The bitch still has two holes, fuck her senseless."

Seconds later I found myself on my knees, my hands pulled high above me, my legs wide apart thanks to the spreader bar as I felt a knife slip between my flesh and the lacy garment which quickly was discarded. Jackson's voice was filled with delight while saying, "Look here brother, this one's just begging for it." I felt his hand take hold of the knob of the extremely large plug and with an audible pop he pulled it out, leaving my rosebud open and eagerly waiting.

My mind was running a hundred miles an hour and at the moment I was as lost in the fantasy as the woman who had ordered it. Finally, when I felt the head of his cock press up against my opening, I waited for the pain. Instead I felt the tip of him go completely in me, the only feeling not discomfort but one that said I'd been waiting for this all my life. "God bro, this bitch is tight!"

I wanted to scream for him not to stop but I remembered, letting my voice come out sounding as if I was in a daze. "Why are you doing this to me?" I felt Jackson pull my hair and as I cried out, my eyes flew open and Jason's hard, erect cock slid into my mouth.

"I guess it's just your lucky day girlie, what can I say?"

Both men began to slowly have their way with me but that was not what I wanted. I remembered him telling me how the drug would lower my inhibitions so I decided to play that part now. Rocking back and forth, I urged them to take more and I saw a look of surprise first on Jason's face and then his smile as he nodded to his brother and they both understood what I wanted.

Everything before this had been artificial. I now had two living objects filing me and it sent me into a frenzy. I slobbered all over the cock in my mouth, tasting it, savoring the tang, the texture while the man behind me began to plunge deep. I felt the final inch of him ram home and I couldn't help the wonderful moan that escaped my lips. The woman's voice was almost gleeful in saying, "Just look at her. Trailer trash always show their true colors when they give into their basest instincts. Just like that harlot that was going to marry my son, this one does her best work on her knees."

She could call me whatever she wanted, I was in heaven. I saw the look in Jason's eyes, the primal hunger and I welcomed it, wanted it, as I took him deep into my mouth. His body began to move at a more frantic pace as did his brother. They used me and I willingly complied, finding their rhythm until suddenly I felt Jackson's body shudder. It was my reward coming and I wanted it more than anything.

Jason pulled free of my mouth and I whimpered as I lost my treat, only to close my eyes in anticipation. As the man behind me was spilling his seed into me, the one in front painted my face with long streaks of hot, sticky cum as it splattered into my hair and on my face. Both men had marked me as their own and like many of my firsts, it had been amazing. But, there was still more to come.

As I hung there I heard an unfamiliar voice whisper in my ear, "Are you alright Holly?"

I gave him a quick nod as he pulled my hair, forcing my head up. "Ready for round two sweetheart?" I opened my mouth obediently as his laugher rang out as I heard, "This ones turning into quite the little cum slut Lee. Come on, give her what she wants."

My mouth was filled first, my bottom second and once again I rode the waves of pleasure which rippled through my body. Both men weren't tentative at all, they simply demanded I give them what they wanted and I was in no position to disobey. I had never known it until now but it was just as I had always wanted it to be.

This time the man standing in front of me came first and when the first spurt of his seed hit the back of my throat, I moaned loud enough to send his partner over the edge and my body welcomed them both. When they had finally finished, I was freed but only long enough to be drug over to where Abby was being strapped into a machine, a second device directly next to hers.

As Jason and Jackson again took my arms they positioned me onto the table, shackling both my wrists and ankles down as my eyes tried to clear as they saw two familiar friends. On one end was a purple phallus while on the other was a matching cock. They positioned both of them, one in my mouth and the other just inside the entrance behind me.

The blonde captive moaned around the intruder in her mouth as what would have been her mother in law looked on in triumph. "There now, I have everything I need. My son will be saved the pain and embarrassment of finding out he had married a tramp like you. You and your sissy friend deserve each other and since I know you can't get enough, either one of you, these machines never grow tired. I can guarantee however, you two will."

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