tagTranssexuals & CrossdressersA Job in the Theatre Ch. 17

A Job in the Theatre Ch. 17


Chapter 17 – Poker night with the boys

"Ted has invited me to his poker game" Paula let slip.

"Oh really? Now that sounds interesting" Sarah said.

"It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the right thing. I want to blow their socks off. I want the poor darlings to be so distracted by me that they can't possibly play cards. Do we have anything like that in wardrobe?"

Sarah smiled. "I'm sure we do. Let's take a look."

They headed to the corridors behind the stage where all the costumes where kept. There was rack after rack of clothes from every time period known to man. They quickly dispensed with most of it focusing on their target. It had to be something highly suggestive, very sexual and fit within the definition of 'domestic help'. It didn't take long for them to find just the thing.

"Oh Sarah...its perfect!"

"Try it on. It may need some alteration to maximize the full effect."

With a quick glance in each direction, Paula shed her dress and stepped into the French Maid uniform. The black silk uniform featured a low square cut bust line trimmed in white lace that pulled together at the waist and flared out into a very short hemline. There was a white apron sown around the front that tied into a big bow in back. The sleeves were short and puffy trimmed in white lace as well. It was simply adorable.

"Mm, not bad" Sarah said appraising the fit. "I will have it taken in a bit at the waist. You have a lovely figure and this should accent it to the fullest. And once you put on the petticoats, that hemline will become very sexy indeed. What do you think?"

Paula stared in the mirror. With the right accessories it could definitely work. "I like it."

Two nights later Paula was getting dressed for Ted's. She felt like a gladiator getting ready for battle, a very different kind of battle to be sure. Thoughts had danced through her head as to what she might do, what they might do. She found it all very exciting.

She fastened the garter belt around her waist and aligned the little rose to be perfectly in front. Then she selected a pair of black stockings with the seams running up the back. That seam had always been so suggestive to her in the past. It was just perfect for this evening. That was followed by the cutest little satin panties featuring black and white ruffles. She quickly tucked her cock between her legs before it became unmanageable.

She picked up the fluffy chiffon petticoat and stepped into it. She had never worn a petticoat before. She pulled it up and adjusted it around her waist. It was very short and the lace ends teased her thighs in a most decadent manner. That was followed by a lace shelf bra that pushed her boobs straight out without covering her nipples.

She slipped into the silk uniform and saw how the petticoat made the dress puff out almost like a ballerina. The lace ends of the petticoat could easily be seen just underneath. The uniform fit her like a glove. She adjusted the neckline around her breasts and teased her nipples with her fingers to make them poke through the material.

She stared at the mirror quite pleased with her reflection. She turned her back to it and bent over at the waist. She glanced over her shoulder and could easily see her satin ruffled panties peeking out from underneath. Perfect!

All that was left were the finishing touches. She donned white lace cuff around her wrists and the cutest little white lace tuff in her hair. All she needed now was her heels. And those were four inch stilettos that buckled around her ankles in a most suggestive way.

A final look in the mirror said it all. She blew herself a kiss. She looked terribly cute and very, very sexy. She slipped on an overcoat and headed for the car. Once inside the Ferrari she put the top up and slipped on a pair of sunglasses.

Ted opened the front door somewhat startled by the overcoat and sunglasses. "Hmm. So you decided to come as a spy?"

"No silly" she said walking through the front door. Once she was inside, she turned and shed the overcoat. "I thought a French Maid driving a Ferrari would draw too much attention."

"Holy Jesus!" Ted exclaimed. His eyes feasted upon her making her cock grow hard.

"I assume that means you approve?" she asked turning slowly around.

"I definitely approve" Ted said smiling.

"Good! Now where can a girl get a drink around here? I need a stiff one."

The guys started showing up an hour later. And having had a few drinks, Paula was ready for them. The game room featured a full length bar across one wall that was flanked by a card table to one side and a pool table in the middle of the room. There were two leather couches sprawled against the opposite wall. The room was a dream come true for any sporting man.

The guys gathered at the bar where Ted made them drinks. They greeted each other, told a few jokes and shared some small talk about business waiting for everyone to arrive. Once they were all their, they gravitated to the card table.

Ted pulled out a fresh deck of cards and began to shuffle. "Looks like you could use another Tom" he said.

"I believe you are right. Tell me, do you have any cigars?"

"You know better than that" Ted smiled. He pressed a button and Paula made her entrance. Tom caught something out of the corner of his eye and turned to see Paula in all her glory. The others noticed his interest and turned to see what it was. One by one they gawked out the stunning, sexy maid standing before them.

"Tom will have a whiskey and water. And could you bring a box of Cubans?" Ted said in a tone reserved for the help.

"Of course, sir" Paula said before giving a slight curtsey. She turned and headed for the bar. Every eye in the place followed her.

And she could feel every one of them too. She was glad for the drinks she shared with Ted before they arrived. She mixed the whiskey and water and placed it on her tray. She reached underneath the bar and pulled out a box of cigars and put that next to the drink. She glanced in the mirror behind the bar and saw that all the men were staring at her. They were clearly impressed. She took a deep breath and headed back to the card table.

She stepped to Tom's side, grabbed his drink and put it on the table making sure he got an eyeful of cleavage. She then grabbed the box of cigars and placed it on the table.

While staying bent over, she turned to Tom and asked, "May I offer you a light?"

The look in her eye was just enough for Tom to get ideas. "Why yes...that would be lovely" he said with a smile. Paula proceeded to retrieve a cigar from the box. She took particular interest in the shape of the cigar by running her finger along its length. She gently tucked the cigar between Tom's lips and produced a lighter. His eyes never left hers. Once the cigar was lit, she gave him a very suggestive smile and disappeared.

The boys rolled their eyes at each other as she left the room. Ted was very pleased. As soon as Paula was gone, Tom leaned forward and beamed, "She lit more than my cigar!"

"You are telling me" said Peter, "I don't smoke, but I think tonight I might give it a try" as they all chuckled.

They played a hand of cards, but everyone was thinking about Paula.

"I believe I will try a cigar" Peter said. He could have reached for a cigar, they were right there. Instead, he turned to Ted. Ted smiled and pushed the button.

Paula performed her cigar magic three more times. Somewhat placated, the boys settled in for some cards. The room filled with smoke and the machismo that naturally comes with a boy's night out. Paula watched from around the corner and silently appeared whenever someone's drink became more than half empty. And she was mixing them strong. She wasn't sure if that was for them or for her. Somewhere in the back of her mind she knew it would be better if everyone was pretty lit before she moved to stage two of her act.

Ted surveyed the crowd and decided the time was right. He looked in Paula's direction and gave her the prearranged nod.

Without further adieu, Paula strolled into the room and stopped at the nearest edge of the table. She slowly descended to the floor. Every head at the table turned in her direction trying to figure out just what the hell she was doing. Ted allowed himself a grin.

Paula crawled underneath the table and made her way between Peter's legs causing him to jump. He immediately looked at Ted for some explanation while feeling his zipper being lowered. Ted gave him a reassuring smile.

Peter remained confused until he felt Paula's fingers wrap around his hardening cock.

Without a single comment, Ted dealt the next hand. Eyes were darting from one to another. Peter felt a pair of warm lips consume his cock. He did his best to stifle a moan.

Slowly but surely everyone began to accept what was obviously happening to Peter. Especially Peter.

They played the hand or at least pretended too. Delicate sounds, familiar sounds, were emanating from underneath the table. Peter did his best to remain expressionless as he received a world class blowjob while sitting amongst his friends who clearly understood what was happening.

Paula ran her tongue along Peter's cock. It was a beautiful cock. The case of nerves she was experiencing before were now dissipating with the feel of a nice, warm cock. She licked and nibbled feeling it get harder and harder. Then Paula slipped it into her mouth. It was not as big as Ted's that was for sure. But it was still above average from her experiences. Oh how she loved cocks!

Ted dealt another hand. Eyes darted to Peter's face as if to validate his pleasure. Yes, it was there. The thought that his cock was embedded in the maid's mouth at that very moment made it so much the hotter for everyone at the table. The sounds were having their affect on everyone. And Peter could feel those eyes upon him even though he did not acknowledge them.

Ted had barely dealt the next hand when Peter closed his eyes tightly and clinched his fists. That sexy maid was draining his cock right down her throat. There was not a soft cock in the house as Peter returned from his orgasm.

With deliberate ease Paula tucked his cock back into his underwear and zipped him back up. She was much more at ease now having tasted Peter's warm, thick sperm. She looked at each man's lap underneath the table and saw one bulge after another.

The room was on pins and needles as everyone wondered what would happen next. Ted played a perfect poker face not giving a single clue. He dealt the next hand as if nothing was happening, nothing at all.

In the deafening silence everyone heard Sam's zipper as it descended. Everyone grinned as it became obvious that everyone was in for a great night.

Paula moved from Sam to Ben, Ben to Tom, Tom to Jake, Jake to Ted. She simply loved sucking cock. And she had never drunk so much sperm before in her life.

Her job now done, she crawled out from the table by Ted's chair. Ted gave her a hand up, pulled her towards him and gave her a kiss. "You were fantastic!" Paula quickly glanced at each of the guys before looking back at Ted and smiled. They were all happy. "Why don't you go with Roxy? She will help you freshen up."

Paula glanced back towards the doorway to find Roxy standing there. She was wearing a cute little crop top that tied behind her neck with tight little matching mini skirt. It was the first time Paula had seen Roxy out of uniform and she was impressed. Her cute little outfit did nothing to hide her muscled physique and everything to accentuate her feminine charms. Paula had every reason to be jealous.

Roxy had seen that look before. She knew exactly what Paula was thinking. Roxy had worked hard for her body and was well aware of the affect it had on others. She held Paula's stare without the slightest hesitation.

Paula broke the stalemate with an uncomfortable smile. How long had Roxy been standing there? Was she watching her under the table? Look at that body! Paula watched the look on Roxy's face change to a smoldering, hungry look as she walked around the table towards her.

Paula had seen that look before. She stepped next to Roxy who then took her arm and folded it underneath her own. Paula could feel her cock stiffening in her panties. Without breaking eye contact with Paula, Roxy said, "Goodnight boys" and she led Paula down the hallway.

It was then that Paula realized her evening was just beginning.

"The pool and hot tub are down to the right and the guest wing is down to the left" Roxy said. Paula listened, but was amazed by her muscles. There were so many things she wanted to ask. Curiosity got the better of her.

"Can I ask you a question?"

"Of course you can."

"What is your arrangement with Ted?"

"I work for Ted. I live here so that I can be available 24/7. That is our arrangement." She stopped dead in her tracks, "And this door goes to my bedroom."

Paula felt a thrill go through her like never before. There was something about Roxy that she couldn't put her finger on. It was some sort of sureness, a quiet strength.

Roxy opened the door to her bedroom and Paula stepped inside. It featured a strange mix of décor between masculine and feminine. There were hints, if not direct signs, that Roxy might be into bondage. The bed was large and sturdy dominating the room. The mirrors that surrounded it were pretty much in your face.

"I understand that you like big cocks" Roxy said. Paula turned towards Roxy just in time to see her mini skirt drop to the floor.

"Oh my god!" Paula said mesmerized.

You could hear a pin drop in the game room. The boys had moved to the couches and were watching a flat screen panel that hung from the wall.

Paula was lying on Roxy's bed with her ass sticking straight up, her legs spread as wide as they would go. Roxy's muscles glistened with sweat as she held Paula's hips still while driving that monster cock into her. Paula's moans of ecstasy filled the game room.

"She is definitely your best yet" Peter said.

"She really loves that cock" said Tom, "and good looking too. I don't know how you do it Ted."


The show that night was perfect. Everything seemed to click in place. The audience gave them a standing ovation. It was the vindication she had sought as a male, but never received. That made it especially sweet now.

Gary walked her back to her dressing room and then went to his own. She sat before her mirror and removed her stage makeup. Everything seemed to be going her way. Her sex life was unbelievable. She had Gary in the palm of her hand and Billy wasn't far behind. She lived in a fabulous house with a gorgeous lady who just happened to have a fantastic cock. She had a boyfriend who was also a marvelous benefactor. Could it be any better?

She slipped into a pleaded scoopnecked silk cami and a cute little leather mini skirt that was so tiny it was almost not there. She laughed remembering how impossible this outfit would have been not that long ago. She touched up her makeup, brushed her hair and headed for the parking lot.

It was hard to imagine how much her life had changed. She never dreamed things would turn out like they did. She could feel her hard nipples poking through the silk cami. She loved having breasts. She opened the door to the Ferrari and cranked it up. She hit the switch and waited for the top to descend. The cabin filled with a disco song from the seventies. She jazzed the volume up and pulled out on the road.

She wasn't sure where she was going, but she was too excited to go home. The radio seemed to be playing every song for her. She danced behind the wheel not caring who saw her. And that seemed to be every man on the road.

Through no fault of its own, the car seemed to find its way to her old neighborhood. She passed by her old apartment building and glanced three stories up remembering what a pain in the ass it was climbing those stairs. That was a thing of the past she smiled. She went another couple of blocks and came across the bar that had been her second home.

On a whim she pulled the car into the parking lot. She shut off the engine certain this parking lot had never seen a Ferrari convertible. She checked herself in the rearview mirror and stepped from the car.

She strolled in the door of the bar looking like she owned the place. And in so many ways, she did. She waltzed right over to a table in the middle of the club knowing every guy in the place was checking her out. The waitress came by and took her order.

Paula casually scanned the crowd, but didn't recognize anyone see knew. She doubted they would have recognized her anyway. After all, there had been a few changes since the last time she was in. She smiled to herself and seductively crossed her legs. She had practically lived in this place. If she had a dime for every dollar she had spent here she could have paid for the Ferrari herself.

The waitress returned with her drink and she reached for her purse.

"No charge" the waitress smiled. "The guy at the end of the bar already paid."

The End

Thanks for all the wonderful commments throughout this series. I'm glad so many of you enjoyed it!

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