Category: Transsexuals & Crossdressers Stories

A Job in the Theatre Ch. 15

by BothWorld©

Chapter 15 -- Doing Darrin

Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties.

"Nice. But I really think these will be better" Sarah said holding up a pink pair featuring ruffles across the back. Paula smiled. "Yes, I think you are right." The panties were part of a set that came with a glove tight corset trimmed in lace featuring two very thin straps with huge bows on the end to hold up her stockings.

Paula slipped the corset on and glanced at her cleavage in the mirror. Her breasts practically jumped out at you. Yes, that should do it she thought.

She slipped on a pair of black stockings and clipped them to the straps underneath the huge bows. Yes, very sexy she thought checking the mirror once again. Sliding on stockings never failed to excite her she thought seeing her erection throbbing back and forth below her corset. She gave it a nice little squeeze. That would have to hold her over until later.

She eased the cute little panties up her legs and deftly tucked her cock between her legs. She turned to see the neat little rows of ruffles going across the back and then back around. She looked at her bulging cleavage as she ran her hand down her perfectly smooth front. Yes, very sexy indeed.

Sarah came out of the closet with a beautiful silk dress. It was light and airy, very feminine. It featured a plunging neckline to show off her cleavage and had a wispy multilayered hemline that caught the eye.

"Now this is very tempting. We do want to tempt dear Darrin."

"Oh we are going to do more than tempt him. Poor Darrin won't know what hit him" Paula said with a smile.

Sarah handed her the dress. "And won't this be suggestive?" she said handing her a thick leather bracelet that screamed bondage. It was in stark contrast to the very feminine dress.

"Mm, I love it" Paula said slipping it on. It was very suggestive. Paula picked a pair of heels with straps that crisscrossed her ankles furthering the bondage illusion. It was a prefect blend of sweet with dangerous.

With a twist of her leg, the split in her dress flew open to reveal the huge eye grabbing bow on the end of her garter strap and her sexy stocking top. "That Darrin better watch out. I might just have to tie him up and have my way with him" Paula said gazing into the mirror.

Sarah decided on a lavender affair with an open and flowing feel to it. It was more conservative than Paula, but just as feminine and beautiful.

"Do you know Darrin?" Paula asked.

"No, I haven't met him" Sarah said taking a sip from her drink. Just then the door bell rang.

"Well, here goes nothing. How do I look?" Paula asked.

"You are smoking hot!" Sarah said.

"Is there any other way?" Paula answered with a smile as she headed to the front door. She took a deep breath and opened the door.

"Don't you look lovely tonight" Ted said walking in followed by his friend. "Paula, I would like you to meet Darrin."

Darrin was a little older than Paula had expected. He was not bad looking, but she was expecting someone younger. He was dressed impeccably wearing what had to be tailor made clothes. There was a subtle elegance about him that suggested extreme wealth.

"Hello Darrin" Paula said coyly. She could tell from the way he looked at her that he was very impressed. At least she had passed that test. "Can I fix you boys a drink?"

"Vodka rocks" Darrin said simply. Ted just shook his head yes. Paula went to fix drinks as Sarah entered the foyer.

"Hey Gorgeous" Ted said giving her a peck on the lips. "I would like you to meet my friend Darrin."

"Hello Darrin. Ted tells us you are in town for a few days" Sarah said catching his Rolex.

"Yes, just business."

"All work and no play is simply no way to be" Sarah said giving him a smile.

Paula returned with their drinks. "I will second that!" She handed Darrin his drink, "I'm sure you boys have something playful in mind for this evening. I know we do."

Darrin grinned giving Paula another once over.

"Now, now Paula. I thought maybe dinner at Elaine's?" Ted said.

"Sounds lovely" Sarah piped in.

"Anything you say" Paula said looking at Darrin. Her innuendo was clear. She slipped her arm through his and said, "Shall we?"

The walked outside to the limo where Roxy was waiting with the door. Her uniform consisted of a black coat, white shirt, thin black tie with black pants. Her hair was tucked up underneath her cap so you really couldn't tell its length. The black leather gloves were fitting, but on her looked slightly wicked.

It all looked rather traditional until you saw those black spiked heels. Then it turned rather sexual. Her uniform hid her body so well. Maybe that was by design, but Paula knew there were some curves underneath all that and she was dying to take a peek. She knew it was stupid, but she was feeling slightly jealous of Roxy.

Paula gave her a slight nod as she climbed into the cavernous rear of the car. As she did, her dress fell open at the split, her garter strap and bow came into view in a most obvious way. She just happened to catch the slightest recognition on Roxy's face.

They shared the customary small talk as they headed to Elaine's. Ted explained that Darrin was in town finishing up a deal they had put together. Paula listened glancing at Darrin who basically smiled and said nothing. She made sure the split in her dress revealed plenty of leg, and at times, the bow. She caught Darrin stealing glances, but did not let on.

They walked into Elaine's and were escorted to a plush booth with high curved walls. Sarah tried her hand at getting the conversation going. Paula decided she would start "entertaining." She slipped her hand down between them and laid it causally on Darrin's thigh.

After Sarah's attempts failed, Paula gave it a whirl. "Did you know that I am starring in a play that is being produced and directed by Sarah?" she asked Darrin.

"No, I didn't."

"Yes, it has been running for a few weeks now" Paula said looking at Darrin. He did have warm eyes she thought. "Sarah is a marvelous director" Paula continued. She moved her hand from his thigh directly to his crotch. She made sure no one else could see. Then she turned to Sarah, "You know I have never asked. How long have you been directing Sarah?"

Paula could feel Darrin growing hard underneath her hand. She loved making the boys horny. She toyed with Darrin's growing cock, running her fingernail along its length, giving it a gentle squeeze here and there until it was fully hard. It was then that she could fully appreciate just how thick Darrin's cock was.

"Well let's see. I guess it has been almost eight years now. Doesn't that sound right Ted?"

"Yes, I believe so" Ted said looking at Sarah.

Paula nonchalantly worked Darrin's zipper down underneath the table without being noticed. While listening to Sarah and Ted, she eased her hand inside his pants. Darrin remained quiet looking at Ted and Sarah along with Paula.

"Let's see...if I remember correctly your first production was AWOL" Ted continued.

"Yes, that was my first production, but my first direction was Seven Brides for Seven Men" Sarah said.

Paula worked Darrin's cock out through his zipper. She couldn't believe how thick his cock was. It had to be the thickest she had ever felt. She ran her fingertips over the end of his cock. Darrin played along perfectly. No one had the slightest idea of what was happening.

"I will never forget that show. So many things went wrong. I guess that is typical for a first time experience" Sarah continued.

Paula casually teased Darrin's cock. He was so hard!

"I remember Stacy Belle was one of the stars" Sarah continued, "She was beautiful, but what a pain she was. I always had to correct her, even on opening night."

Paula began stroking Darrin's thick cock in the most discrete way. She didn't want the others to know. Paula saw the waitress approaching the table and stopped.

"Good evening, welcome to Elaine's. What can I get you folks to drink?"

Paula gave Darrin a coy smile, "What are you having, Darrin?"

Darrin kept up the façade, "What would you suggest?"

Paula squeezed his thick cock firmly, "I think you should try a Fuzzy Orgasm" she said with a straight face.

Darrin turned to the waitress, "Yes, I will have one of those." She took the rest of their orders and left. Paula returned to the most delicate task of jacking Darrin off underneath the table. Sarah returned to speaking about the play. Ted was blissfully unaware of everything.

As everyone listened to Sarah, Paula brought Darrin to the edge of orgasm. She gave him credit. He maintained perfect decorum. She was getting ready to take him over the edge when the waitress returned with their drinks causing her to stop. Darrin was literally throbbing in her hand. In a strange way she was bonding with quiet Darrin.

Paula teased the head of his cock with her fingernail until the waitress left. As soon as she did, Paula squeezed Darrin's cock firmly and pumped him to orgasm. She was amazed at his self control. Even she was not aware of his orgasm until she felt warm cum drooling down her fingers.

"...and that brings us to Paula starring in my current play" Sarah said.

Dessert before dinner Paula pulled her hand out from underneath the table. She stared Darrin in the eye and said, "Yes, I play the Vixen" as she cat licked his cum from her fingers. Darrin was impressed. Ted was caught off guard, but pleased. Sarah was amused.

" I see" Darrin said with the slightest of grins.

They had a wonderful dinner albeit uneventful. Paula was surprised when Darrin asked her to dance afterwards. They danced two songs and Paula was impressed. They returned to the table to share an after dinner drink where Ted and Sarah were discussing something. Paula gave Sarah the nod and they were off to the ladies room.

"Well I can see you have Darrin in the palm of your hand" Sarah giggled. "Does Darrin have a nice cock?"

"Very nice. And thick! I can barely get my fingers around it" Paula smiled. "Listen, do me a favor. You and Ted stay here until I give you a call."

"A call? What are you going to do?" Sarah asked intrigued.

"I'm going to entertain Darrin" Paula said as they left the restroom.

They joined the boys and strolled out to the dance floor. About halfway through the dance, Paula took Darrin's hand and led him out of the restaurant.

Roxy saw them approach the car and jumped out to hold the door. "Where too ma'am?" she asked.

"No where. And we don't want to be disturbed" Paula said looking her in the eye.

"Yes ma'am" Roxy said with the slightest of smiles.

Fucking in the limo

Roxy closed the door behind them. Paula was sitting on the back seat and made Darrin sit on the facing seat.

"I hear you like girls like me? Is that right?" she asked staring at him. He gave her the slightest of smiles. Her hands went down to her skirt. Her fingers started casually inching it upwards. "Tell me Darrin...what is it you like about girls like me? Hmm?" Her stocking tops came into view followed by those huge bows.

Darrin was completely engrossed. The bulge reappeared in his pants. That thick cock was hard to hide once it got excited.

"Do you see something you like?" she teased, "Do you like my stockings Darrin?" He continued to stare stone faced. Paula inched her dress up so just a hint of pink panty showed. "Or maybe you prefer my cute little panties..."

His eyes widened followed by the slightest of grins. And there it was. Darrin was a fool for panties. Paula was so glad she went with the ruffles Sarah had suggested. Sarah always knew the right choice.

"Yes...that's it...I can see it in your eyes. You want to see my panties...don't you?" Paula spreads her legs wider. She could see excitement dancing in his eyes.

"Well Darrin...why don't you take a peek..." Paula said leaning back against the seat. She clasped her hands behind her head offering herself completely.

Darrin leaned forward and gently placed his hands on her thighs. The feel of her cool nylons raced through his body. He inched his hands up and toyed with her bows. They were so cute and sexy. He couldn't help but wonder how it felt to dress like that.

Paula could feel her heart racing. Feeling Darrin's huge hands toying with her bows was so exciting. She loved the way his eyes danced as he gazed upon her. She loved the power she had over men.

Slowly Darrin inched up, took the hem of her dress and pushed it up revealing her crotch completely. His eyes feasted upon the cute pink panties framed by the stocking straps with just a hint of corset. And right there in the middle of those panties was a nice firm bulge.

Ever since that first encounter so many years ago Darrin had been hooked. Girls like Paula caught his imagination then and had never let him go. And here he was once again.

"Mm, I see what you like. You say you like my cute little panties...but you are more interested in what's in them...aren't you?" Darrin glanced up at her quickly, but then lowered his eyes back to her bulge. "Such a nasty boy...a nasty boy with a secret... How would it be if people were to know just how much... you... love... much you love the feel of hard, hot flesh between your lips" Paula whispered sensuously. She was getting to him. " would that be... well they never have to know... your secret is safe with are so hungry for my cock...well...what are you waiting for nasty boy..."

Darrin eased his hands up to her panties, gently pulled then down exposing her hard throbbing cock. It was all Paula could do to sit back and let it happen. She wanted to reach out and cram his face down on her cock.

Darrin took his own sweet time. He ran his hands up and down her nylon clad legs slowly. Then he leaned in and took her cock between his lips.

"Yes...oh yes" Paula cried out feeling his warm, wet mouth consume her length.

Darrin lost all composure. He loved her small cock; he could take it all at once. And feeling that warm tube of hard flesh throbbed inside his mouth turned him into a cock hungry slut!

Paula was thrilled as Darrin unleashed his measurable skills. He was totally obsessed with her cock. His tongue was everywhere, his lips nibbled; his hands strolled up and down her legs. Paula was delicious with pleasure. She tried her best to keep her legs spread giving Darrin full access to the object of his desire. There wasn't a woman on earth who could suck cock the way he was.

Paula felt herself loosing control. It was the last thing she wanted. But Darrin was just too good. Darrin was driving her to orgasm with remarkable speed. Visions of his nice thick cock filled her head and she exploded in his mouth with a distinct force. "OHHHhhhh" she cried pumping her balls into his hungry mouth. Darrin had no problem keeping up with her.

Once she was empty, Darrin pulled off and sat back in his seat. For the first time that evening he had a full smile on his face. "How do I taste baby?" she asked through half closed eyes. She leaned forward and squeezed his nice hard cock. "Don't talk with your mouth full" she giggled. "Tell me later darling...because right now I want you to fuck me with this!" Paula pulled off her cute pink panties and turned over exposing herself to Darrin.

Roxy was standing guard outside the limo. A discrete smile crossed her face when it started rocking. Inside Paula had her ass tilted up filled with Darrin's thick cock. Each of his thrusts drove her face deeper into the plush leather seat.

She had always dreamed of fucking in a limo.

He fucked her good and hard before pumping his load into her. He eased his cock out and fell back against the jump seat. Paula remained with her face planted in the seat, luxuriating in the warm, glowing feeling emanating from her ass. There was nothing like a good solid fuck.

Finally she flipped over sitting in the seat. She gazed at Darrin who was totally satisfied. She saw her pink panties lying on the floor of the limo. She handed them to Darrin and said, "Put them on... nasty boy." It was a command.

Darrin looked at her, his weakness obvious. She understood it completely. She "suffered" from it herself. He eased them up his legs. He loved the feel of silk around his cock. He could feel the ruffles in the back tickling his ass.

Paula ran her fingers over his cock offering a smile of recognition. She then slipped his cotton briefs up her legs and pulled her dress over them. It had been another lifetime, literally, since she had worn those. Thankfully that lifetime had been replaced. She reached for the car phone to call Sarah.

Minutes later the door opened and Ted and Sarah joined them. The car reeked of sex. Paula and Darrin looked like the cats that ate the canary. Ted and Sarah weren't sure what to say, so they rode in silence back to Sarah's house.

Roxy opened the door and stood obediently waiting. Paula leaned forward and gave Darrin a kiss. "Thanks for a lovely evening. The dessert was wonderful."

"Well it certainly looks like that turned out nicely" Sarah said later inside the house. "I hope Darrin lived up to your expectations."

"I have always wanted to fuck in a limo" Paula said with a smile. "I can't wait for Ted to ask for another favor...This one was pretty yummy."

"I hope you saved a little something for me..." Sarah said taking Paula in her arms and kissing her. Sarah's hand started with Paula's breast. She toyed with her nipple through the delicate fabric of Paula's dress knowing how excited that would make her. But what she really wanted was cock. Her hand left her breast and traveled down to Paula's crotch. Yes Paula was hard, very hard. But something didn't feel right. Sarah broke their kiss and pulled Paula's dress up.

"Oh my god..." she exclaimed as everything became obvious. "You are so incorrigible."

The boys rode in silence. Having known Darrin for years, Ted was not expecting much conversation. But Darrin seemed to exhibit a certain satisfaction. If anyone could please him, it would be Paula. She showed every sign of being his best yet.

"I assume you had a good time this evening..." Ted mentioned causally looking out the window. The ocean looked so romantic at night.

"Beyond belief" he said thinking about his hard cock nestled within the cute pink panties. "That one is special."

High praise indeed Ted thought. He had never known Darrin to be so talkative.

Ted and Roxy Ted poured himself a drink from the bar in the middle console. He glanced out the rear window at a full moon hanging just over the ocean. He was thinking of Paula. What started as just another project had turned into something special. She had that quality that cannot be developed. You either have it or you don't. It was clear to him that she had it.

He allowed himself a special treat and pulled a cigar from the humidor. He brought it to flame and pushed a button causing the roof to slide back. It wasn't every day you closed a deal worth two hundred million dollars.

Roxy pulled the lumbering limo through the gates and down the winding drive to the front door. She stepped around to open the rear door. Ted immerged pausing to look once again at the moon. "Thanks Roxy" he said before strolling through the massive oak doors to his ocean side estate and up to his bedroom.

His bedroom was a rich mixture of red velvet and mahogany. He stepped into his closet and removed his clothes. He opened a drawer and removed a pair of silk briefs. Although a masculine cut, they were every bit as delicious as their feminine counterpart. He slipped on his smoking jacket and walked out to his favorite chair overlooking the ocean.

Category: Transsexuals & Crossdressers Stories