tagTransgender & CrossdressersA Job in the Theatre Ch. 20

A Job in the Theatre Ch. 20


Chapter 20 -- Gary becomes Gayla

"Be a dear and get that bag from the car," Paula winked.

"Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with that erection dominating his leather pants. You could see it a mile away. Gary could never go outside looking like that. Billy could care less.

Billy looked Gary in the eye, had that crooked little smile of his. Gary couldn't believe what he had just agreed to...willingly. He had just met this guy, didn't even know him.

And yet he had basically promised to do all kinds of things he shouldn't do, horribly embarrassing things, things over the edge. He had pledged to be his secret lover. It was all so wrong. He was so excited his hands shook.

Billy hadn't been too sure about any of this when Paula first mentioned it. It sounded so crazy. But she was right; a blowjob is a blowjob no matter who is delivering it. He certainly didn't have any problem with Paula sucking his cock. How was this any different? There was no question that Gary could suck a mean cock. Man could he suck cock. He tried to picture what Gary might look like once he was dressed. It would get a lot better once that happened. He looked at Gary's lips, pictured his cock lodged between them and grinned.

Billy went to the car and Paula looked at Gary. She could see he was a little freaked out. After all this was a pretty big step for him. "I knew you would like this. He is perfect for you. And he won't tell a soul. What a fabulous cock he has...don't you think?"

Whatever else was true, that certainly was. "This is all so crazy."

"It sure is. You are going to love it," Paula said with a smile that spoke volumes.

He realized that she was probably right.

Billy returned with the bag and handed it to Paula. "Make yourself at home big boy. You can do anything you like...except play with your cock. That's her job now." A large smile crossed Billy's face as they disappeared into the bathroom.

She locked the door behind them and propped the bag up on the ledge. It was filled with all kinds of clothes, makeup and an assortment of toys. Of course both of them knew their way around a makeup bag being actors. She pulled it out and handed it to Gary. He took it and put it on the sink. He looked at his face in the mirror. He would need a closer shave.

She was behind him pulling down his panties as he picked up his razor. "Now I want you to have fun with this. Just be the sexy little slut you always wished you had met. Once your makeup is on, you are the girl of your dreams. More importantly, you are the girl of his dreams. You can do anything that she would do, probably more...definitely more. Put all your boy thoughts away. Let your other side come out and play. Now it's her turn."

Gary shaved as close as he could while listening to her instructions. It was impossible to contain his excitement. Paula covered his legs with cream and started shaving them. She knew they couldn't take too long or Billy's excitement would wane. She was not about to let that happen.

Gary started putting on his face as she finished up his legs. Paula rose up and looked in the mirror. "Go feminine, but don't go overboard. You know how too much makeup can be a distraction. I have a dark wig for you to wear. So keep that in mind."

She picked up a wash cloth and turned on the cold water. She soaked it real good, squeezed out most of the water over the sink. "Okay stop," she said to Gary. He pulled the eyeliner away and looked at her. She took the cold washcloth and pressed it against his poor throbbing cock.

"Whoa!" he jerked feeling the cold wet cloth pressed against him. "What are you doing?" he squealed as his cock shriveled up.

"You'll see." His poor cock was totally limp within the minute. She reached into the bag and pulled something out. Gary had never seen anything like it before. He was trying to figure out what it was when Paula leaned down and pushed his limp penis through it and fastened the other part around the base of his penis, behind his balls. She slipped a tiny lock through the clasp that held the two parts together and locked it. Gary looked down to find his penis snuggly encapsulated within the clear plastic device. There was a slit at the end so he could pee. Other than that, his penis was rendered useless. He explored the device with his fingers, but could not feel his cock at all.

"Believe me baby, this is for your own enjoyment. You won't believe the orgasm you will have when this comes off," she said slyly. The look on her face sold him completely. He turned back to the mirror and continued with his eyeliner. This was all so wrong. He couldn't wait!

It didn't take Gary long to finish his face. Paula thought he did a wonderful job. She pulled the dark wig out and pulled it into place. The dark hair color was in complete contrast with his natural blonde hair. He looked so different. His critical eye knew just what to do. Gary adjusted it and brushed out the bangs perfectly even over his eyes.

Then it hit him. This was not for the stage. This was for his personal enjoyment. He felt that familiar tingle in his crotch. His cock began to swell, but couldn't. The device was preventing him from gaining an erection. He instinctively grabbed himself, but all he could feel was the device. The more he thought about it, the more his cock tried to grow. But it simply was not happening. He found the mixed emotions flooding his mind intriguing. He wondered just how long it would be before the device was removed. He turned to Paula and said, "I'm ready. What should I wear?"

"First things first girlfriend," she said pulling up an outrageous black lace bra. It was the same one Sarah used on her that first day so long ago. Paula showed him the silicone breasts inserted in the see-through cups with the slightly protruding nipples. Gary smiled as he slipped his arms through it and Paula fastened it behind him.

He reached down and cupped his new breasts. They felt totally real. He ran his finger over the nipples and felt his cock tug against the device. His mind was doing flip flops.

She pulled out the matching lace thong and held it up for him to see. His eyes danced across the garment. She reached down and fondled his caged cock. She gave him a big smile and pulled the delicate little thong up his freshly shaved legs. Once again his cock tugged unsuccessfully on the device as the wisp of material slipped up his crack.

She pulled out the cutest little black top with white stripped sleeves featuring a scoop neck. Paula pulled it over his head and into place. Gary adjusted his boobs. He looked down and saw the tiny nipple points poking through the material and smiled. That was followed by the shortest of short white skirts that barely covered his buttocks. She pulled out a big thick black leather belt and draped it loosely around his hips.

"Oh my!" he gushed. They were twins! She was the sweet and innocent twin wearing pink. He was the hot and smoldering twin wearing black. Gary loved it. He could feel his identity taking shape. That identity solidified as Paula pulled a pair of thigh high fishnets up his legs polished off by a wicked pair of stiletto heels that buckled around his ankles.

"Oh yeah," Paula said admiring her work. She turned Gary back towards the mirror. His jaw dropped. "I now pronounce you Gayla...the naughty, naughty Gayla."

"Gayla..." Gary said staring at himself in the mirror.

Paula unlocked the bathroom door, "Let's work it girl."

Gayla gave her a smile, threw back her shoulders thrusting her boobs out and strutted out of the bathroom. She could feel the tiny lock bouncing against her cage with every step she took.

Billy heard the door open and looked up. He saw Gayla strutting towards him. He couldn't believe his eyes. "Holy shit!" he said straightening up on the couch.

Gayla understood for the first time the power of womanhood as Billy's eyes scanned her from head to toe. Once again her cock tugged on the device, but to no avail. The look on Billy's face told her everything she needed to know.

"Wow! That is totally incredible," Billy said trying to reconcile what he knew with what he was seeing. "You are gorgeous...I mean hot...well actually sexy, really sexy." He barely noticed Paula standing next to her.

"Turn around baby," Paula suggested. Gayla turned halfway around when Paula stopped her. Gayla could feel Paula's hand tease up the back of her thigh disappearing underneath her extremely short skirt. "Bend over baby," Paula whispered in her ear. Gayla leaned forward as Paula lifted her skirt showing Billy the skinny strip of lace going up her buttocks.

"Wow...that is hot!" Billy said smiling ear to ear.

Gayla straightened back up and turned to face Billy. She could barely contain her smile. Billy was staring at her incredibly short skirt. He raised the front of it to take a peek underneath. Paula noticed that in doing so he was very careful not to touch her. She remembered that Billy had never touched her cock either. He had never shown any interest in cock. She needed to work on that.

"Now, now," she said batting Billy's hand away. She could see the inquisitive look on his face. "More about that later," she smiled. She looked at Gayla and said, "Why don't you sit with your handsome boyfriend?"

Gayla smiled and curled up on the couch snuggling in next to Billy. Now it was her turn to run her hand up and down that leather covered thigh before nestling it into his crotch. Billy's lump inflated before her very eyes. And she got to experience the troubles with an extremely short skirt as she caught Billy's eye darting down to her exposed crotch.

It was a very heady experience for her. Her cock constantly tugged against the device. Although she couldn't gain an erection, her libido was in full swing. She had never felt hornier in her life. Billy's cock had swelled to full erection and pressed insistently against her hand.

Paula sat down in a chair across from the couch. She wanted to keep her distance so the two get to know each other. She knew that Gayla would do just fine given her skills as an actor and her lust for cock. But she wondered about Billy. But it looked like he was so taken by her transformation that her worries might be misplaced. The lump in those leather pants told her he was getting over any reservations he might have had.

"You sure know how to make your boyfriend horny," Paula teased. "I can see that lump from over here."

Gayla looked at Paula nervously. She was right. This was her boyfriend so she could do whatever she wanted. And she wanted to play with that fabulous cock. She glanced at Billy for just a second before grabbing his zipper and inching it down. Gayla could feel Billy reacting to her touch. It just added to the eroticism in her mind. She pulled his cock free and lazily fondled it with her fingers.

She loved his cock. It was just the right size, perfectly shaped. She loved that she could make him hard by just brushing up against him. For just a second she daydreamed about the things she would do to it. She moaned unconsciously as her fingertip rounded the tip.

Watching the two of them was definitely having an impact on Paula. She crossed her legs once squeezing her erection. Gayla was so hot. She loved the way Gayla caressed Billy. Billy was really getting into it. She had to find a way to get Billy interested in cock. All he needed was a little nudge to get the ball rolling. She couldn't resist edging her hand down to her panties and rubbing herself sensuously.

"Do you like having a boyfriend?" Paula asked Gayla.

"Mmm" Gayla hummed.

"Doesn't he have a fabulous cock?" Paula said easing her hand into her panties. "Think of all the wonderful hours you will spend sucking that warm beautiful piece of flesh."

That sent Gayla over the edge. She leaned down and took Billy's length between her lips. She took great pains to paint his shaft with her salvia. She danced her tongue around the tip several times toying with his slit.

Paula couldn't help it. She pulled her cock from her panties and wrapped her fingers around it. She pulled on it slowly watching Gayla. "Do you like the way she sucks your cock?" she asked Billy.

"Yeah, yeah...absolutely. She is totally hot."

Paula reached into her purse and got something. Maybe this would provide the nudge she was looking for. She walked over to the couch. Gayla released Billy's cock and sat up straight. "Open up baby," Paula said to Billy. He gave her an uncertain look and opened his mouth. Paula showed the two blue pills to Gayla. "Do you know what this is?"

Gayla looked at the pills and shook her head no. Billy had no clue either.

"This is twelve hours of hard dick!" she smiled taking one of the pills. She popped the other down Billy's throat. "You can thank me later," she giggled. "Do you have any more vodka left? I think we are going to need another drink."

Gayla's mind was racing. Twelve hours of hard dick? So many thoughts went through her brain. She almost forgot to breath. "Yes, I think I do," she said realizing she had been asked a question. "Let me get them."

She got up and walked to the kitchen as Paula sank down on the couch next to Billy. Gayla looked over her shoulder and caught both of them staring at her ass. She could see both their cocks standing straight up. She ducked into the kitchen to fix the drinks thinking this was beyond anything she could have imagined.

Billy turned to Paula and whispered, "What's that thing on her cock?"

"It's a restraining device. It keeps her from gaining an erection."

Billy raised his eyebrows in amazement.

"The hornier she gets, the more she will have to take it out on you. See? And with that pill we took...we will be able to give her plenty."

Now he got it. This was just getting better all the time he thought.

Paula moved in closer and whispered in his ear, "We were talking in the bathroom. She has never been fucked in the ass." She reached over and squeezed his fabulous cock. "She told me she wanted you to be her first." It was a complete and total lie, but Billy didn't know that. And Gayla had no idea that Paula was planting ideas in her boyfriend's head.

Paula knew the best way to start their kinky little relationship was with a hot and heavy fuck session. She knew that Billy's cock was getting ready to turn into steel. He was going to be hornier than he had ever been in his life. She was going to make sure he turned Gayla into a whimpering, whipped little cock whore who was totally and hopelessly addicted to Billy's prick.

All she needed to do now was get Billy thinking about cock. Not his cock, but Gayla's cock. She had ever intention of emptying Gayla's balls directly into Billy's mouth. Once that little deed was accomplished, her part would be done. The rest of the relationship would be up to the two of them.

"I can definitely do that," Billy grinned.

"I know you can sugar," Paula said giving his cock one last squeeze. "She's going to love it."

Gayla returned with fresh drinks. The thing around her cock was never far from her thoughts. It seemed to heighten her senses, not dull them. Walking in heels was a constant reminder her girl side was here to play.

"Didn't she turn out well?" Paula said so pleased.

"She looks so hot," Billy said wrapping his hand around his cock. Man he was horny. This was so different from anything he had done before. Who could have thought he would be sitting on someone's couch, stroking his cock, getting ready to have the time of his life. Not only that, but the girl sitting next to him had this hard-on peeking out from under her skirt. How kinky was that?

Gayla handed them their drinks. She made hers a little stronger hoping it would calm her nerves. She brought it to her painted lips and just about drained it on the first pull.

It was time for Billy to try out his power. "Hey baby...ah, girlfriend," Billy corrected himself, "I'm feeling pretty horny. Why don't you come over here and lick my balls." Gayla blushed as Billy pulled his cock to one side. His balls were squeezed out of his zipper.

"Maybe we should remove those tight leather pants first," Gayla smiled.

"Yeah...good idea," Bill grinned. Man, she was actually going to do it. He was so glad he took Paula up on her idea.

Gayla stepped over and grabbed the pant legs and pulled. She could hardly believe she was stripping a guy's pants off. Her eyes were glued to his throbbing cock. Twelve hours! This was going to be good. She threw the pants to one side and made herself comfortable between his legs.

"Yeah, that's it baby. Do them one at a time...real slow," Billy said peering down. Gayla gave him a quick grin and ran her tongue in slow motion up over his ball sack. "Yeah, that felt good."

Gayla held his balls gently. There they were. Two big balls in her hand and she had just licked them. And she was going to lick them until he said stop. She felt her cock tug on the device. She leaned forward and began the tortuously slow process of caressing his balls.

"Mmm, yeah...I like watching you," Billy said almost drooling. "That is making me so horny."

Paula took the opportunity to remove her top, skirt and panties. All she was wearing was her half cup pushup bra and her long leather boots. Billy's eyes went straight to her breasts. He couldn't get over a guy getting boobs, but then again he really didn't think of her as a guy, not really. What he saw was a woman, a woman with some of the best looking boobs he had ever seen. Yeah her hard cock was right there, but he saw a woman.

He looked at his crotch and saw another woman licking his balls. And she was just as hot looking. Yeah, he knew better, but his cock told him it was okay.

"Man I'm horny," he said looking at Paula. "I love your breasts."

"Here baby...suck on them for me..." Paula said leaning over offering him a nipple.

"Yeah..." Billy said taking the nipple between his lips. His cock was so hard. It wouldn't stop throbbing. He could feel Paula's erection poking against his side. He knew exactly what she was feeling. Gayla looked up to watch Billy work that nipple while she licked his balls. She was glad Paula was helping her with Billy. She saw Paula's cock pressed up against his side. It didn't seem to bother him at all.

Billy pulled away to catch his breath. "Man, I am so fucking horny!" He looked down at Gayla, "OH fuck that is good! Kiss my cock. Come on, kiss it." He released the grip he had on his cock and it swung right out and hit Gayla in the face. She grabbed the base, held it in front of her lips, looked Billy in the eye. She started planting little kisses all over the head.

"Shit yeah!" he said watching. "Now...kiss hers." Gayla could tell Billy was really getting into it now. She loved the way he was taking control, giving orders.

"Hold it for her," Paula said to Billy. "Help your girlfriend baby."

Billy's eyes darted to Paula, found her smiling. Tentatively he reached over and held her cock. That wasn't so hard. He pulled on it getting the feel of it. It felt pretty good. He pointed it at Gayla, "Now...kiss it." She leaned over and kissed the head of Paula's cock. She crooked her tongue up Paula's slit capturing the pearly drop she found.

"Man...you are so into dick," Billy observed.

"Looks good doesn't it?" Paula suggested.

Who was she kidding Billy thought? It looked great...watching a hot woman licking a cock. Does it get any better than that?

"Hell yeah it does," Billy grinned. "Come here girlfriend...make love to my dick." The word 'girlfriend' rolled right off his tongue. Paula and Gayla both caught it. Billy tried to remove his hand, but Paula stopped him. Gayla swirled her tongue around the head of Billy's oozing cock. His taste took her to a new level.

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