He heard the footsteps approaching the door. He knew he could turn back, but he knew he wasn’t going to. He wanted the money. He loved leaving that house with money in his pocket, and he wasn’t sure if it mattered if he ended up humiliated or with a permanently gaping asshole. Surely five thousand dollars was more than enough to pay a doctor to fix a stretched hole…
The door opened. The makeup girl, who was also the set fluffer, stepped aside, letting Luke into the house. The blinds were all closed and there was a bare mattress in the middle of the floor. “You’re late,” she said.
“I thought he said eleven,” said Luke.
“We film at eleven. You need to get into makeup and wardrobe—that will probably take an hour. Come on—quickly now. We need to pick out a costume.” She brought Luke to a room he’d never seen before. It appeared to be someone’s bedroom, but the bed was buried in lingerie. The makeup girl rushed over to the bed and started digging around until she found a red lacy one piece. Luke’s gut turned at the thought of putting it on his body. “This should be perfect,” she said. She turned it around and looked at the bottom. “It’s even got a hole. That should make things easier.” She tossed it at Luke and then she said, “Go on—get changed.”
Luke was slow to take off his shirt and pants. As his underwear hit the floor, the makeup girl sighed loudly. “What is it?” Luke asked. His voice was quiet and shaken.
“You didn’t shave. You can’t go on camera like that. C’mon—go to the bathroom. We need to get you shaved up.”
Luke found the idea of shaving to be uncomfortable, but the reality turned out to be far more uncomfortable than he thought, because it was the makeup girl who went ahead and did the shaving for him. “Don’t move,” she said as she held up his ball sack. “I don’t want to nick you.” She ran the razor over his ball sack while he looked up at the ceiling and tried to imagine that five thousand dollar payout.
It only took ten minutes to remove all of Luke’s body hair, but it felt like much longer. Getting dressed took another ten minutes. The lace teddy was easy to get on, but the stockings weren’t quite as simple. They had lots of little straps that connected to the lingerie, and the little clips were tedious to connect. Then came the makeup. The makeup girl worked quickly, brushing on different products while checking the time constantly. “Shit,” she kept muttering, every time her gaze went down to her wristwatch.
“Sorry for being late,” Luke said a number of times, but she never seemed to accept his apology.
“Wait here,” she said before zipping off to another room. She came back with a long blonde wig. She quickly slapped it onto Luke’s head and then she started to style it. Luke had no mirror to look at. He could just hope that the transformation was dramatic enough that no one would recognize him.
“Is she ready yet or what?” Luke heard the producer yell from the other room.
“Two seconds!” the makeup artist yelled back. And that’s when Luke realized that he was ‘she’ in this scenario. For the next hour, Luke was going to be a woman, just like Elle, minus the fake tits. He was going to be expected to play the role of ‘female’, no matter what the porn producer threw his way.
She made a few quick adjustments to Luke’s wig, and then she brushed a few more quick products onto Luke’s face. “That will have to do,” she said with another sigh, and Luke couldn’t help but think that he looked ridiculous. He probably looked like an ugly man in drag. The producer would take one look at him and then tell him to get out, without a dime in his pocket. And Luke wondered if that would be more or less humiliating than the alternative: staring in a cross-dressing porno.
CHAPTER VI
When Luke walked out, he was happy to see the familiar face of Elle. She was standing next to the mattress, and her face lit up when she saw Luke stepping into the room, wobbling dangerously on tall heels. “Oh my God, look at you!” she said with cheeks that were suddenly red.
Standing next to Elle was an unfamiliar woman with thick eyeliner and dark hair. She was dressed up in tight black lingerie. She didn’t smile at the sight of Luke, but she didn’t seem to be put-off.
“Okay, we’re behind schedule so we need to get moving. You—what are we calling you?” the producer said, pointing at Luke.
“Me?” he said.
The producer shook his head and sighed. “Please tell me you can do a female voice,” he said.
Luke cleared his throat. “I’m sorry,” he said, using the voice he spent the whole night practising.
“What are we calling you? What’s your sissy name? C’mon, we don’t have all day here. I’ve got another shoot starting in two hours and I still have to flip the set.”
Luke picked the first name that came to his mind. “Tiffany,” he said, though he had no idea where the name came from.
“Okay—Tiffany, you’re going to start right where you are. When I say action, you walk into the room and ask the girls why there’s a mattress on the floor. Then they’ll tell you that they were playing truth and dare, and now it’s your turn. You pick dare, and you can figure out the rest, I’m sure. Okay, are we ready? Lights are hot—can we get the cameras rolling?”
Luke’s heart was pounding. He still hadn’t seen himself in the mirror. He still had no idea if he looked like a girl or like a goblin. He felt stupid but relieved that Elle was in the scene with him. And the girl next to Elle—was she a real girl or was she a tranny too? Or maybe she was another cross-dresser—though her tits looked real. She had a pretty face, though her lack of smile was somewhat intimidating.
“Action!” the producer yelled as he stepped back against the wall. Luke took a deep breath and he stepped forward.
“Hey. What’s going on? What’s with the mattress?” he asked in his feminine voice.
“Hey Tiffany. We were just playing a game of truth or dare,” Elle said. “Do you want to play with us?” She was using a cheesy porno voice, which brought a slight smile to Luke’s face. She knew how to relieve the tension. Her presence alone was enough to relieve the tension.
“I’d love to play,” Luke said. He felt a cool draft teasing up his bare legs as he took another step forward. “Whose turn is it?”
“It’s your turn,” said the girl with the black hair. Her voice was sexy, with a bit of a rasp to it.
“What’s it going to be, Tiff? Truth or dare?” Elle asked. Elle was wearing a familiar outfit: the tiny white dress that made her small body look so cute.
“How’s about… Dare?” Luke said. His legs were trembling slightly—but even a slight amount of trembling made balancing in those heels a difficult task. He looked over and saw a picture frame on the wall. In the frame’s glass, he could slightly make out his own reflection. He could see his long hair and the dark eyeliner around his eyes—but he wasn’t able to look for long enough to get a good mental image before Elle said, “I dare you to eat out Jodie’s pussy.”
Jodie, the girl with the dark hair, made a fake gasp and covered her mouth with her hand. “Elle—are you serious?” she said.
“I’m waiting,” Elle said, putting her hands on her hips.
Luke was happy to get down on his knees, taking his weight off of those wobbly heels. Jodie stepped forward in her little black outfit—close enough that Luke was able to reach forward and slip a finger under her black panties. He gently pulled the panties aside to reveal Jodie’s pussy—but instead of a pussy, Luke got a big, long cock. It flopped out in front of him.
“Oh my God, Jodie! That’s not a pussy! You didn’t tell me you were a trap!” Elle said.
Luke didn’t need to fake a reaction. His shocked reaction was real. He couldn’t believe how convincing Jodie was—even though Elle was just as convincing, so there should have been no surprise.
“Well, Tiff? Are you going to eat me out or what?” asked Jodie.
Luke’s heart skipped a beat. He closed his eyes for a moment and reminded himself that he’d already sucked a cock before, and it wasn’t scary the first tim
e. He could do it again—especially for five grand. So he gently lifted up the cock and brought it to his lips. It was big—bigger than his own and bigger than Elle’s. He opened his mouth carefully and allowed the dick inside. Then he started to suck. And it really wasn’t so bad. Jodie was wearing a nice perfume that was a bit sweet and a bit oaky. Her skin was soft and warm, just like a woman’s. And she nestled her fingers into Luke’s wig in a comforting sort of way. It wasn’t long before Luke could feel that cock in his mouth growing.
“Okay, it’s my turn,” Elle said. “I pick dare.”
“I dare you to stick your big cock in Tiffany’s mouth with me,” Jodie said.
“Oh, Jodie. You’re so naughty.” Elle stepped forward, pressing her body tight against Jodie’s. Then she hiked up her skirt and fished her cock out from her white panties. She held it up and brought it up to Luke’s already-full lips. Luke opened his mouth as wide as he could, and Elle quickly shoved her length inside. Now, Luke had two cocks in his mouth, and both of them were growing fast, stretching out his lips the way his asshole had been stretched out just a couple of days before.
“Wow, she’s really good at sucking cock, isn’t she?” Elle said.
“I bet these aren’t the first cocks she’s ever sucked. I always knew she was a whore,” said Jodie.
“Should we treat her like a little whore?” Elle asked.
“I get the pussy first,” Jodie said, pulling her cock out from Luke’s mouth, finally allowing Luke to have a breath of air, even though it was a breath of air with another cock still on his tongue. She ran around him with a little skip, and then she plopped down behind him, making the mattress shake. Luke kept sucking Elle’s cock.
Luke felt Jodie’s feminine fingers toying at the backside of his lingerie. “Oh my God, Elle—she’s a boy! Look at this cock!” She grabbed Luke’s cock with a firm fist. “She’s even hard already. Can you believe that?” Luke’s heart fluttered into his gut. He hadn’t realized until that moment that he was hard. And what made him hard? Was it the sight of the two trannies in their lingerie? Or was it the feeling of two thick cocks sliding in and out of his mouth? Either way, it wasn’t looking good for his masculinity.
“I guess I’ll just fuck her little asshole then,” Jodie said, slapping her hard cock first against Luke’s left butt cheek and then his right, and then right between the two. He felt a strange wet sensation dripping down his butt crack. He couldn’t look back to see what was happening. For a moment, he thought she was peeing on him. Then, Jodie said, “I’m going to use this whole bottle of lube, because she’s so tight.” A slight wave of relief washed over Luke, though the cold sweat was still tickling the back of his neck.
Elle pulled out from Luke’s mouth, letting him breathe properly. She walked around to join Jodie around back. Jodie now had her tip pressed against Luke’s butthole. “I think she’s too tight. I don’t think I can get in. What do you think?” asked Jodie.
“You just need to push. Here, let me show you.” She reached and grabbed Jodie’s cock with a firm grip. She started to mash that cock against Luke’s hole. And then a moment later, he felt the penetration. He nearly screamed as his asshole stretched wide to accommodate her thick girth. He looked forward and saw the camera in front of him, looking at his face to get his reaction. He tried not to look too uncomfortable, but he couldn’t stop squirming and groaning. Assholes weren’t meant to accommodate rods as big as Jodie’s.
“Oh my God, she’s so tight!” Jodie said as she pushed in deeper and deeper.
It hurt a little bit, but it wasn’t the pain that was making Luke squirm—it was the pleasure. It was almost too intense to handle. He tried biting his tongue, but that didn’t make it go away. He tried digging his nails into the mattress, but that didn’t make the euphoria stop. He even tried biting the mattress, even though he had no idea how many girls and boys had been fucked on the thing. But still, that intense buzzing wouldn’t leave his genital region. “Fuck!” he groaned as Jodie’s pelvis finally reached his butt. She was completely inside of him. Her tip was nearly touching his sternum. He tried clenching but her cock was too hard. There may as well have been a metal pipe inside of his rectum.
He felt a hand rubbing his back, as if trying to console him. He looked back and saw Elle looking into his eyes with a bright smile. There was a peaceful moment of silence, but it came to a swift end when Jodie suddenly pulled back and then rammed her cock in hard and deep. Now she was fucking him. “Oh fuck, it feels so good!” she said, holding his hips firmly. Elle turned back towards the action. She got down low, with her face hovering over Luke’s ass. Then she stuck out her tongue and started licking Jodie’s shaft every time it was exposed.
And now, Luke was harder than ever before. His cock was bobbing stiff between his legs. That euphoria kept growing, getting stronger and stronger, making his whole body tremble as he pushed back the urge to scream. But he couldn’t hold that urge back forever. Finally, he belted out a loud war cry.
“She’s coming! Get the camera down there!” yelled the producer.
Luke was confused. Who was coming? He could feel Jodie’s cock inside of him and he could tell that she wasn’t coming. Elle was just watching, not even touching her cock, so she couldn’t have been coming. But that only left him…
He looked down and saw that his cock was erupting, spraying that mattress with blast after blast of his hot load. As soon as Elle noticed, she stuck a hand under his body to catch the fresh load. She got enough to fill the palm of her hand. Then she brought it up to Luke’s lips and said, “I dare you to suck it all up, you little slut.” She was grinning.
And Luke’s mind was spinning too quickly to decline the dare. He leaned forward and slurped his own cum into his mouth.
“Swallow all of it,” she said. So Luke swallowed it. The camera was once again pointed right at his face. Unlike the last two shoots he did, this time, he was the star of the show. The camera was almost always on him, and the many thousands of viewers would be watching him when they tuned in to watch the video. And still, he had no idea if he was properly disguised or if he just looked like himself with a bit of lipstick and eyeliner.
“Shit,” Jodie groaned, her voice slipping just a little bit. She pulled out and then she came around, taking Elle’s place next to Luke’s face. She pointed her swollen tip right at his lips and then she said, “Open wide.” He opened his mouth just in time for a series of warm, gooey blasts. Some of it trickled out the side of his mouth, but Jodie made sure to wipe the escaping cum back into his mouth. She even pushed his jaw closed and said, “Swallow it, slut.” So Luke swallowed her load as well.
And then he felt his empty backside filling up. He looked back and saw that Elle was now inside of him, pumping his ass, getting her own cock ready to fill his slutty mouth with warm tranny cum. She fucked him hard and fast, and it still felt good, though a bit sore from being stretched and pounded for what felt like an hour. Elle didn’t take long. It was only a minute before she pulled out and rushed over to Luke’s face. She opened his mouth with her beautiful fingers and then she rested the tip of her cock on his bottom lip and began to unload. She produced more cum than Jodie—and he swallowed every last drop.
The two trannies stood up. “That was a fun game,” said Elle, a moment before the producer yelled, “Cut!”
Jodie left quickly to get herself changed and showered. Elle stayed in the living room to help Luke to his feet. “How was that? You okay?” she asked with her gentle smile. It was hard to believe that a precious girl with a smile like hers could end up in pornography. Then again, it was hard to believe that Luke could end up being fucked by trannies in popular pornography videos. Sometimes life is unexpected.
“I’m good,” Luke said, carefully standing up as he wobbled in his heels.
“You’ll get used to the heels,” she said, as if she knew Luke was going to be doing more shoots like this one.
Luke managed to force a smile.
“Want
to shower with me again?” she asked.
“Okay.”
As soon as Jodie was out of the shower, Luke and Elle hopped in. He felt much more comfortable next to her as her cock swayed gently in the warm water. He really was getting used to this strange new lifestyle, though he didn’t want it to become his lifestyle. Sure: the money was good and the work was easy, but at some point, Luke was going to have to value his dignity. He couldn’t keep doing these videos. With each video that he did, he was increasing the risk of being seen by friends and (God forbid) family members. Luke knew there was a price for everything, but was there really a price for all of his dignity?
“You should come with me some time to Lovers’ Lane. It’s this lingerie store downtown. It’s where I get all of my outfits. They just got these adorable leopard print one-pieces in. We should do a shoot with them. Maybe we can get a guy to take turns fucking us while we’re on all fours.”
Luke’s stomach turned. His heart was pounding slowly, but powerfully, making him lightheaded. “Maybe,” he said.
“What’s wrong?” she asked.
“Nothing. It’s just—this can’t be what you wanted to do with your life.”
She stared at him with wide eyes that quickly became offended. “What do you mean?” she asked.
“Well, didn’t you want to be a doctor or a fire-fighter when you were a kid? Surely you didn’t want to be doing weird fetish porn shoots. Right?” He felt like an asshole, but he question was genuine. He couldn’t understand why she was doing this to herself. He couldn’t help but wonder if the only reason she transitioned was to make more money. And by now, she probably had nearly half a million dollars. She was making so much money for each shoot, and it seemed like she was doing new shoots every day.
She rolled her eyes. “People are so obsessed with careers. How many people in the world are actually working their dream careers? Maybe one percent? And I think that’s being generous.” She stepped out from the shower and snapped a towel off the rack. She quickly wrapped it around her body. “And if you hate it so much, no one’s making you do it.” She picked up her clothes off the floor. “I thought I was doing you a favour.”
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